1H-indole-3-carboxylic acid [CAS 771-50-6; InChIKey KMAKOBLIOCQGJP-UHFFFAOYSA-N; Reaxys, Subs

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O OH

9 substances in Re2016-03-08 21h:00m:09s (EST) axys

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Reaxys ID 129435 View in Reaxys

1/9 CAS Registry Number: 771-50-6 Chemical Name: 1H-indole-3-carboxylic acid; indole-3-carboxylic acid Linear Structure Formula: C6H4C2HNH(COOH) Molecular Formula: C9H7NO2 Molecular Weight: 161.16 Type of Substance: heterocyclic InChI Key: KMAKOBLIOCQGJP-UHFFFAOYSA-N Note:

O OH

NH

Substance Label (43) Label References 6a

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4

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8

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3

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5f

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6b

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2

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8r

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Freire, Ernesto; Hayashi, Yoshio; European Journal of Medicinal Chemistry; vol. 68; (2013); p. 372 - 384, View in Reaxys 1; ICA

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1a

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8.1

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RCO2H to 11

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5

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3, R=H

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2d

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IAA

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21

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1d

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I3acid

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23

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10a

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16

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1b

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ICA

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starting to 7b

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Patent-Specific Data (13) Location in Patent References Page/Page column

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Patent; ALEVERE MEDICAL CORPORATION; DUNCAN, Diane; KAMERZELL, Tim; PALMER, Mark, A.; WO2014/143125; (2014); (A1) English, View in Reaxys Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; US2009/258876; (2009); (A1) English, View in Reaxys Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; EP2108649; (2009); (A1) English, View in Reaxys Patent; KOREA RESERACH INSTITUTE OF CHEMICAL TECHNOLOGY; WO2009/125923; (2009); (A2) English, View in Reaxys Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/11131; (2008); (A2) English, View in Reaxys Patent; Bissantz, Caterina; Grundschober, Christophe; Ratni, Hasane; Rogers-Evans, Mark; Schnider, Patrick; US2007/27173; (2007); (A1) English, View in Reaxys Patent; ASTELLAS PHARMA INC.; WO2007/26920; (2007); (A2) English, View in Reaxys Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1698611; (2006); (A1) English, View in Reaxys Patent; SUVEN LIFE SCIENCES LIMITED; WO2004/48330; (2004); (A1) English, View in Reaxys Patent; Zeneca Ltd.; US6365751; (2002); (B1) English, View in Reaxys Patent; Aventis Pharma Deutschland GmbH; US6337344; (2002); (B1) English, View in Reaxys Related Structure (1) References Sundberg,R.J. et al.; Journal of Organic Chemistry; vol. 37; (1972); p. 719 - 724, View in Reaxys Derivative (1) Derivative C13H17NO2Si

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Melting Point [°C]

215 - 217

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Melting Point [°C]

232 - 234

Zhang, Qi; Guo, Wen-Juan; Fu, Chang-Liang; Ma, Shuang; Zhu, Mei-Qin; Chemistry of Natural Compounds; vol.

49; nb. 1; (2013); p. 117 - 118; Khim. Prir. Soedin.; nb. 0023-1150; p. 2, View in Reaxys 3 of 31

Melting Point [°C]

168

Patent; Council of Scientific and Industrial Research; US2005/70435; (2005); (A1) English, View in Reaxys 4 of 31

Melting Point [°C]

208 - 210

Solvent (Melting Point)

acetone; H2O

Zaletova, Janka; Dzurilla, Milan; Kutschy, Peter; Pazdera, Pavel; Kovacik, Vladimir; Aldoelfi, Juraj; Bekesova, Slavka; Collection of Czechoslovak Chemical Communications; vol. 69; nb. 2; (2004); p. 453 - 460, View in Reaxys 5 of 31

Melting Point [°C]

219 - 220

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Melting Point [°C]

212 - 214

Arai; Masuda; Kiriyama; et al.; Chemical and Pharmaceutical Bulletin; vol. 29; nb. 4; (1981); p. 961 - 969, View in Reaxys 7 of 31

Melting Point [°C]

210 - 211

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Melting Point [°C]

222

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Mackie et al.; Journal of Fluorine Chemistry; vol. 10; (1977); p. 437,442, View in Reaxys 9 of 31

Melting Point [°C]

219 - 222

Bergmann et al.; Journal of Heterocyclic Chemistry; vol. 14; (1977); p. 1122,1131, View in Reaxys 10 of 31

Melting Point [°C]

211 - 212

Papayan et al.; Armyanskii Khimicheskii Zhurnal; vol. 29; (1976); p. 1062; Chem.Abstr.; vol. 87; nb. 39217w; (1977), View in Reaxys 11 of 31

Melting Point [°C]

220

Solvent (Melting Point)

ethanol

Patent; Awramenko et al.; SU444769; (1975); Ref. Zh., Khim.; vol. 14; nb. 0154p; (1976), View in Reaxys 12 of 31

Melting Point [°C]

210 - 212

Kariya et al.; Journal of Medicinal Chemistry; vol. 15; (1972); p. 659,660, View in Reaxys 13 of 31

Melting Point [°C]

237 - 240

Aldridge,D.C. et al.; Journal of the Chemical Society [Section] C: Organic; (1971); p. 1623 - 1627, View in Reaxys 14 of 31

Melting Point [°C]

234 - 236

Katner; Organic Preparations and Procedures; vol. 2; (1970); p. 297,299,301, View in Reaxys 15 of 31

Melting Point [°C]

216

Bravo et al.; Gazzetta Chimica Italiana; vol. 100; (1970); p. 652,656, View in Reaxys 16 of 31

Melting Point [°C]

219

Gilbert,E.E.; Journal of Heterocyclic Chemistry; vol. 6; (1969); p. 483 - 490, View in Reaxys 17 of 31

Melting Point [°C]

225 - 229

Yagil; Journal of Physical Chemistry; vol. 71; (1967); p. 1034,1039, View in Reaxys 18 of 31

Melting Point [°C]

245 - 246

Solvent (Melting Point)

aq. ethanol

Kasparek; Heacock; Canadian Journal of Chemistry; vol. 45; (1967); p. 771, View in Reaxys 19 of 31

Melting Point [°C]

235 - 239

Abrash; Niemann; Biochemistry; vol. 4; (1965); p. 99,100, 103, View in Reaxys 20 of 31

Melting Point [°C]

217 - 218

Patent; Ruetgersw. Teerverwert.; DE1193946; (1965); Chem.Abstr.; vol. 63; nb. 13218g; (1965), View in Reaxys 21 of 31

Melting Point [°C]

218 - 220

Solvent (Melting Point)

aq. ethanol

Elkin; Miller; Journal of Pharmaceutical Sciences; vol. 52; (1963); p. 79, View in Reaxys 22 of 31

Melting Point [°C]

218

Patent; Roussel - UCLAF; GB933566; (1963); Chem.Abstr.; vol. 60; nb. 2899d; (1964), View in Reaxys 23 of 31

Melting Point [°C]

241

Buechi et al.; Archiv der Pharmazie (Weinheim, Germany); vol. 295; (1962); p. 209,212, View in Reaxys; Buechi et al.; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 295; (1962); p. 209,213, View in Reaxys 24 of 31

Melting Point [°C]

220

Solvent (Melting Point)

acetone; H2O

Hart; Potts; Journal of Organic Chemistry; vol. 27; (1962); p. 2940, View in Reaxys 25 of 31

Melting Point [°C]

217 - 220

Solvent (Melting Point)

benzene; acetone

Prochazka; Sanda; Collection of Czechoslovak Chemical Communications; vol. 25; (1960); p. 270,279, View in Reaxys

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26 of 31

Melting Point [°C]

247

Solvent (Melting Point)

acetone; benzene

Comment (Melting Point) Decomp.at:240 degreeC.vorgeheiztes Bad. Shaw et al.; Journal of Organic Chemistry; vol. 23; (1958); p. 1171,1176, View in Reaxys 27 of 31

Melting Point [°C]

222 - 223

Solvent (Melting Point)

aq. ethanol

Comment (Melting Point) Decomp.geschlossene Kapillare.

Fawcett et al.; Proceedings of the Royal Society of London, Series B: Biological Sciences; vol. 148; (1958); p. 543,547, View in Reaxys 28 of 31

Melting Point [°C]

222

Solvent (Melting Point)

aq. acetone

Millich; Becker; Journal of Organic Chemistry; vol. 23; (1958); p. 1096,1097, View in Reaxys 29 of 31

Melting Point [°C]

218 - 220

Majima; Kotake; Chemische Berichte; vol. 55; (1922); p. 3870; Chemische Berichte; vol. 63; (1930); p. 2239, View in Reaxys 30 of 31

Solvent (Melting Point)

ethyl acetate; light petroleum

Ellinger; Chemische Berichte; vol. 39; (1906); p. 2520, View in Reaxys; Zatti; Ferratini; Chemische Berichte; vol. 23; (1890); p. 2296; Gazzetta Chimica Italiana; vol. 20; (1890); p. 707, View in Reaxys 31 of 31

Melting Point [°C]

218

Solvent (Melting Point)

aq. acetone

Comment (Melting Point) Decomp.im zugeschmolzenen Roehrchen.

Ellinger; Chemische Berichte; vol. 39; (1906); p. 2520, View in Reaxys; Zatti; Ferratini; Chemische Berichte; vol. 23; (1890); p. 2296; Gazzetta Chimica Italiana; vol. 20; (1890); p. 707, View in Reaxys Sublimation (1) Comment (Sublimation)

References

sublimiert bei ca.

200grad

Prochazka; Sanda; Collection of Czechoslovak Chemical Communications; vol. 25; (1960); p. 270,279, View in Reaxys

Density (2) 1 of 2

Density [g·cm-3]

1.448

Measurement Tempera- -173.16 ture [°C] Type (Density)

crystallographic

Location

supporting information

Liu, Wei; Li, Hou-Jin; Xu, Meng-Yang; Ju, Ying-Chen; Wang, Lai-You; Xu, Jun; Yang, De-Po; Lan, Wen-Jian; Organic Letters; vol. 17; nb. 21; (2015); p. 5156 - 5159, View in Reaxys 2 of 2

Density [g·cm-3]

1.411

Measurement Tempera- 19.84 ture [°C] Type (Density)

crystallographic

Luo, Yang-Hui; Sun, Bai-Wang; CrystEngComm; vol. 15; nb. 37; (2013); p. 7490 - 7497, View in Reaxys Adsorption (MCS) (1) 1 of 1

Description (Adsorption (MCS))

Adsorption isotherm

Solvent (Adsorption (MCS))

H2O

Temperature (Adsorption (MCS)) [°C]

24.9

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Partner (Adsorption (MCS))

mercury

Benedetti, Luca; Fontanesi, Claudio; Camurri, Giulio; Battistuzzi Gavioli, Giovanna; Collection of Czechoslovak Chemical Communications; vol. 56; nb. 4; (1991); p. 750 - 759, View in Reaxys Boundary Surface Phenomena (MCS) (1) 1 of 1

Description (Boundary Surface Phenomena (MCS))

Surface tension

Temperature (Boundary Surface Phenomena (MCS)) [°C]

20 - 23

Yusawa; Journal of Biochemistry (Tokyo, Japan); vol. 22; (1935); p. 49,67, View in Reaxys Chromatographic Data (5) Chromatographic Location data

References

HPLC (High performance liquid chromatography)

Gang, Chen; Shen, Ming-Xi; Xin, Wu; Fan, Xue-Mei; Ma, Hong-Mei; Wu, Hong-Hua; Pei, Yue-Hu; Chemistry of Natural Compounds; vol. 49; nb. 2; (2013); p. 291 - 293; Khim.

Prir. Soedin.; vol. 49; nb. 2; (2013); p. 248 - 249,2, View in Reaxys; Pedras, M. Soledade C.; Abdoli, Abbas; Bioorganic and Medicinal Chemistry; vol. 21; nb. 15; (2013); p. 4541 4549, View in Reaxys; Tang, Jian-Jun; Xia, Hou-Lin; Cheng, Yong-Xian; Luo, Qi; Di, Lei; Lu, Qing; Hou, Bo; Zuo, Zhi-Li; Zhang, Li; Ma, Xiu-Jing; Journal of Asian Natural Products Research; vol. 17; nb. 1; (2015); p. 20 - 26, View in Reaxys

GC (Gas chromatography)

Yu, Xinyu; Luo, Jia; Chen, Lijun; Zhang, Chengxiang; Zhang, Rutan; Hu, Qi; Qiao, Shanlei; Li, Lei; RSC Advances; vol. 5; nb. 85; (2015); p. 69800 - 69812, View in Reaxys

UPLC (Ultra performance liquid chromatography)

Strehmel, Nadine; Böttcher, Christoph; Schmidt, Stephan; Scheel, Dierk; Phytochemistry; vol. 108; (2014); p. 35 - 46, View in Reaxys

TLC (Thin layer chromatography)

Pu, Xiang; Li, Guangzhou; Yang, Tao; Li, Guoyou; Yi, Jinhai; Zhang, Guolin; Luo, Yinggang; Natural Product Research; vol. 27; nb. 7; (2013); p. 603 - 608, View in Reaxys

HPLC (High performance liquid chromatography)

supporting information

Fei, Peng; Wang, Chuan-Xi; Yang, Xie; Jiang, Hong-Lei; Chen, Lu-Jie; Uribe, Paulina; Bull, Alan T.; Goodfellow, Michael; Hong, Jiang; Lian, Yun-Yang; Natural Product Research; vol. 27; nb. 15; (2013); p. 1366 - 1371, View in Reaxys

Conformation (1) Object of Investi- References gation Conformation

Brandt, W.; Gruendler, W.; Zeitschrift fuer Physikalische Chemie (Leipzig); vol. 264; nb. 6; (1983); p. 1121 1129, View in Reaxys

Crystal Phase (2) Description (Crys- Location tal Phase) Crystal growth

supporting information

References Liu, Wei; Li, Hou-Jin; Xu, Meng-Yang; Ju, Ying-Chen; Wang, Lai-You; Xu, Jun; Yang, De-Po; Lan, Wen-Jian; Organic Letters; vol. 17; nb. 21; (2015); p. 5156 - 5159, View in Reaxys

Structure of the solid

Luo, Yang-Hui; Sun, Bai-Wang; CrystEngComm; vol. 15; nb. 37; (2013); p. 7490 - 7497, View in Reaxys

Crystal Property Description (7) Colour & Other Location Properties

References

white yellow yellow

Yoo, Woo-Jin; Nguyen, Thanh V. Q.; Guiteras Capdevila, Montse; Kobayashi, Shu; Heterocycles; vol. 90; nb. 2; (2015); p. 1196 - 1204, View in Reaxys supporting information

Ouyang, Xuan-Hui; Song, Ren-Jie; Wang, Cheng-Yong; Yang, Yuan; Li, Jin-Heng; Chemical Communications; vol. 51; nb. 77; (2015); p. 14497 - 14500, View in Reaxys Yan, Xu; Xue-Ping, Sun; Xiu-Guo, Zhang; Wan-Ping, Tong; Chemistry of Natural Compounds; vol. 51; nb. 4; (2015); p. 800 - 802; Khim. Prir. Soedin.; nb. 4; (2015); p. 683 684,2, View in Reaxys; Sun, Jian Fan; Wu, Yi; Yang, Bin; Liu, Yonghong; Chemistry of

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Natural Compounds; vol. 51; nb. 5; (2015); p. 975 - 977; Khim. Prir. Soedin.; nb. 5; (2015); p. 836 - 837,2, View in Reaxys green

Zhang, Qi; Guo, Wen-Juan; Fu, Chang-Liang; Ma, Shuang; Zhu, Mei-Qin; Chemistry of Natural Compounds; vol. 49; nb. 1; (2013); p. 117 - 118; Khim. Prir. Soedin.; nb. 0023-1150; p. 2, View in Reaxys

brown

supporting information

Fei, Peng; Wang, Chuan-Xi; Yang, Xie; Jiang, Hong-Lei; Chen, Lu-Jie; Uribe, Paulina; Bull, Alan T.; Goodfellow, Michael; Hong, Jiang; Lian, Yun-Yang; Natural Product Research; vol. 27; nb. 15; (2013); p. 1366 - 1371, View in Reaxys

white

supporting information

Yoo, Woo-Jin; Capdevila, Montse Guiteras; Du, Xiangwei; Kobayashi, Shu; Organic Letters; vol. 14; nb. 20; (2012); p. 5326 - 5329,4, View in Reaxys

yellow

Xiao, Hai-Tao; Liu, Bin; Hao, Xiao-Yan; Yang, Xiao-Sheng; Sun, Qian-Yun; Chemistry of Natural Compounds; vol. 45; nb. 4; (2009); p. 539 - 541, View in Reaxys; Wang, Yu; Haemaelaeinen, Antti; Tois, Jan; Franzen, Robert; Tetrahedron Asymmetry; vol. 21; nb.

19; (2010); p. 2376 - 2384, View in Reaxys

Crystal System (2) Crystal System Location Monoclinic

supporting information

Monoclinic

References Liu, Wei; Li, Hou-Jin; Xu, Meng-Yang; Ju, Ying-Chen; Wang, Lai-You; Xu, Jun; Yang, De-Po; Lan, Wen-Jian; Organic Letters; vol. 17; nb. 21; (2015); p. 5156 - 5159, View in Reaxys Luo, Yang-Hui; Sun, Bai-Wang; CrystEngComm; vol. 15; nb. 37; (2013); p. 7490 - 7497, View in Reaxys

Decomposition (1) 1 of 1

Decomposition [°C]

194 - 196

Wang, Yu; Haemaelaeinen, Antti; Tois, Jan; Franzen, Robert; Tetrahedron Asymmetry; vol. 21; nb. 19; (2010); p.

2376 - 2384, View in Reaxys Dissociation Energy (1) Dissociation Ener- Bond Type gy [Jmol-1] 1.37494E+06

N-H

References Notario; Abboud; Cativiela; Garcia; Herreros; Homan; Mayoral; Salvatella; Journal of the American Chemical Society; vol. 120; nb. 50; (1998); p. 13224 - 13229, View in Reaxys

Dissociation Exponent (10) 1 of 10

Dissociation Exponent (pK)

4.1

Dissociation Group

COOH

Temperature (Dissociation Exponent) [°C]

25

Solvent (Dissociation Exponent)

H2O; various solvent(s)

Method (Dissociation Exponent)

spectrophotometric

Type (Dissociation Exponent)

a1/apparent

Linares, R. M.; Gonzalez, A.; Ayala, J. H.; Afonso, A. M.; Gonzalez, Venerando; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 51; nb. 10; (1995); p. 1691 - 1702, View in Reaxys 2 of 10

Dissociation Exponent (pK)

4.21

Dissociation Group

COOH

Temperature (Dissociation Exponent) [°C]

25

Solvent (Dissociation Exponent)

H2O; various solvent(s)

Method (Dissociation Exponent)

spectrophotometric

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Type (Dissociation Exponent)

a1/apparent

Linares, R. M.; Gonzalez, A.; Ayala, J. H.; Afonso, A. M.; Gonzalez, Venerando; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 51; nb. 10; (1995); p. 1691 - 1702, View in Reaxys 3 of 10

Dissociation Exponent (pK)

5.29

Temperature (Dissociation Exponent) [°C]

20

Solvent (Dissociation Exponent)

H2O

Method (Dissociation Exponent)

spectrophotometric

Type (Dissociation Exponent)

a1/apparent

Cativiela, Carlos; Dejardin, Jean-Louis; Elguero, Jose; Garcia, Jose I.; Gonzalez, Emmanuel; Mayoral, Jose A.; Collection of Czechoslovak Chemical Communications; vol. 55; nb. 1; (1990); p. 72 - 79, View in Reaxys 4 of 10

Dissociation Exponent (pK)

7

Temperature (Dissociation Exponent) [°C]

20

Solvent (Dissociation Exponent)

ethanol; H2O

Type (Dissociation Exponent)

a1/apparent

Comment (Dissociation Exponent)

Ratio of solvents: 50:50

Cativiela, Carlos; Dejardin, Jean-Louis; Elguero, Jose; Garcia, Jose I.; Gonzalez, Emmanuel; Mayoral, Jose A.; Collection of Czechoslovak Chemical Communications; vol. 55; nb. 1; (1990); p. 72 - 79, View in Reaxys 5 of 10

Comment (Dissociation Exponent)

(pk')pK(a) (25percentig. wss. A.) : 5.8

Kasparek; Heacock; Canadian Journal of Chemistry; vol. 45; (1967); p. 771, View in Reaxys 6 of 10

Comment (Dissociation Exponent)

(pk')pK(a) (50percentig. wss. A.) : 7.05

Kasparek; Heacock; Canadian Journal of Chemistry; vol. 45; (1967); p. 771, View in Reaxys 7 of 10

Comment (Dissociation Exponent)

(pk')Messung der pK-Werte

Yagil; Tetrahedron; vol. 23; nb. 6; (1967); p. 2855 - 2861, View in Reaxys 8 of 10

Comment (Dissociation Exponent)

(pk')pK: 7+-0.05 in 50percentig. A.

Melzer; Journal of Organic Chemistry; vol. 27; (1962); p. 496,498, View in Reaxys 9 of 10

Comment (Dissociation Exponent)

(pk')pK: 8.92+-0.05 in 95percentig. A.

Melzer; Journal of Organic Chemistry; vol. 27; (1962); p. 496,498, View in Reaxys 10 of 10

Dissociation Exponent (pK)

5.25

Temperature (Dissociation Exponent) [°C]

25

Solvent (Dissociation Exponent)

H2O

Type (Dissociation Exponent)

apparent

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Angeli; Gazzetta Chimica Italiana; vol. 22 II; (1892); p. 17, View in Reaxys Further Information (4) Description (Fur- References ther Information) Further information

Jamieson; Hutzinger; Phytochemistry (Elsevier); vol. 9; (1970); p. 2029,2033, View in Reaxys

Further information

Teitei; Dalton; Australian Journal of Chemistry; vol. 22; (1969); p. 997,1007, View in Reaxys

Further information

Kost et al.; J. Gen. Chem. USSR (Engl. Transl.); vol. 38; (1968); p. 1809,1762, View in Reaxys

Further information

Yagil; Journal of Physical Chemistry; vol. 71; (1967); p. 1034,1039, View in Reaxys

Interatomic Distances and Angles (1) Description Location Comment (Interatomic Distances and Angles) Interatomic dissupporting infortances and angles mation

Single Crystal Xray Diffraction

References

Liu, Wei; Li, Hou-Jin; Xu, Meng-Yang; Ju, Ying-Chen; Wang, LaiYou; Xu, Jun; Yang, De-Po; Lan, Wen-Jian; Organic Letters; vol. 17; nb. 21; (2015); p. 5156 - 5159, View in Reaxys

Ionization Potential (1) References Redchenko et al.; Theoretical and Experimental Chemistry; vol. 14; (1978); p. 653; ; p. 841, View in Reaxys Liquid/Liquid Systems (MCS) (6) 1 of 6

Description (Liquid/Liquid Systems (MCS))

Distribution between solvent 1 + 2

Partner (Liquid/Liquid Systems (MCS))

n-BuOH, water

Martin, George C.; Scott, I. M.; Neill, S. J.; Horgan, R.; Phytochemistry (Elsevier); vol. 21; nb. 5; (1982); p. 1079 1082, View in Reaxys 2 of 6

Description (Liquid/Liquid Systems (MCS))

Distribution between solvent 1 + 2

Partner (Liquid/Liquid Systems (MCS))

ether, water

Martin, George C.; Scott, I. M.; Neill, S. J.; Horgan, R.; Phytochemistry (Elsevier); vol. 21; nb. 5; (1982); p. 1079 1082, View in Reaxys 3 of 6

Description (Liquid/Liquid Systems (MCS))

Distribution between solvent 1 + 2

Partner (Liquid/Liquid Systems (MCS))

EtOAc, water

Martin, George C.; Scott, I. M.; Neill, S. J.; Horgan, R.; Phytochemistry (Elsevier); vol. 21; nb. 5; (1982); p. 1079 1082, View in Reaxys 4 of 6

Description (Liquid/Liquid Systems (MCS))

Distribution between solvent 1 + 2

Partner (Liquid/Liquid Systems (MCS))

CH2Cl2, water

Martin, George C.; Scott, I. M.; Neill, S. J.; Horgan, R.; Phytochemistry (Elsevier); vol. 21; nb. 5; (1982); p. 1079 1082, View in Reaxys 5 of 6

Description (Liquid/Liquid Systems (MCS))

Distribution between solvent 1 + 2

Partner (Liquid/Liquid Systems (MCS))

petrol, water

Martin, George C.; Scott, I. M.; Neill, S. J.; Horgan, R.; Phytochemistry (Elsevier); vol. 21; nb. 5; (1982); p. 1079 1082, View in Reaxys

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6 of 6

Description (Liquid/Liquid Systems (MCS))

Distribution between solvent 1 + 2

Partner (Liquid/Liquid Systems (MCS))

toluene, water

Martin, George C.; Scott, I. M.; Neill, S. J.; Horgan, R.; Phytochemistry (Elsevier); vol. 21; nb. 5; (1982); p. 1079 1082, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.20 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

12

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

20

Guella; Mancini; N'Diaye; Pietra; Helvetica Chimica Acta; vol. 77; nb. 7; (1994); p. 1999 - 2006, View in Reaxys Space Group (2) Space Group 14

Location

Comment (Space Group)

supporting information

a = 4.4189 Å; b = Liu, Wei; Li, Hou-Jin; Xu, Meng-Yang; Ju, Ying-Chen; Wang, Lai10.4812 Å; c = You; Xu, Jun; Yang, De-Po; Lan, Wen-Jian; Organic Letters; vol. 17; 16.03096 Å; β = nb. 21; (2015); p. 5156 - 5159, View in Reaxys 95.3299 °; Z = 4; T = 100 K; Method = Single crystal Xray diffraction; atomic positions available

14

References

a = 4.4701 Å; b = Luo, Yang-Hui; Sun, Bai-Wang; CrystEngComm; vol. 15; nb. 37; 10.61 Å; c = (2013); p. 7490 - 7497, View in Reaxys 16.061 Å; β = 94.93 °; Z = 4; T = 293 K; Method = Single crystal Xray diffraction

NMR Spectroscopy (36) 1 of 36

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H

NMR (400 MHz, DMSO-d6) δ 7.13-7.21 (2H, m), 7.47 (1H, dd, J=1.5, 7.0 Hz), 8.00-8.02 (2H, m), 11.8 (1H, s), 11.9 (1H, br)

Nemoto, Koji; Tanaka, Shinya; Konno, Megumi; Onozawa, Satoru; Chiba, Masafumi; Tanaka, Yuuki; Sasaki, Yosuke; Okubo, Ryo; Hattori, Tetsutaro; Tetrahedron; vol. 72; nb. 5; (2016); p. 734 - 745, View in Reaxys 2 of 36

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

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Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Original Text (NMR Spectroscopy)

13C

Signals [ppm]

107.4; 112.2; 120.6; 121; 122.1; 126; 132.3; 136.4; 165.9

NMR (100 MHz, DMSO-d6) δ 107.4, 112.2, 120.6, 121.0, 122.1, 126.0, 132.3, 136.4, 165.9

Nemoto, Koji; Tanaka, Shinya; Konno, Megumi; Onozawa, Satoru; Chiba, Masafumi; Tanaka, Yuuki; Sasaki, Yosuke; Okubo, Ryo; Hattori, Tetsutaro; Tetrahedron; vol. 72; nb. 5; (2016); p. 734 - 745, View in Reaxys 3 of 36

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Yoo, Woo-Jin; Capdevila, Montse Guiteras; Du, Xiangwei; Kobayashi, Shu; Organic Letters; vol. 14; nb. 20; (2012); p. 5326 - 5329,4, View in Reaxys; Fei, Peng; Wang, Chuan-Xi; Yang, Xie; Jiang, Hong-Lei; Chen, Lu-Jie; Uribe, Paulina; Bull, Alan T.; Goodfellow, Michael; Hong, Jiang; Lian, Yun-Yang; Natural Product Research; vol. 27; nb. 15; (2013); p. 1366 - 1371, View in Reaxys; Liu, Wei; Li, Hou-Jin; Xu, Meng-Yang; Ju, Ying-Chen; Wang, Lai-You; Xu, Jun; Yang, De-Po; Lan, Wen-Jian; Organic Letters; vol. 17; nb. 21; (2015); p. 5156 - 5159, View in Reaxys 4 of 36

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Yoo, Woo-Jin; Capdevila, Montse Guiteras; Du, Xiangwei; Kobayashi, Shu; Organic Letters; vol. 14; nb. 20; (2012); p. 5326 - 5329,4, View in Reaxys; Fei, Peng; Wang, Chuan-Xi; Yang, Xie; Jiang, Hong-Lei; Chen, Lu-Jie; Uribe, Paulina; Bull, Alan T.; Goodfellow, Michael; Hong, Jiang; Lian, Yun-Yang; Natural Product Research; vol. 27; nb. 15; (2013); p. 1366 - 1371, View in Reaxys; Liu, Wei; Li, Hou-Jin; Xu, Meng-Yang; Ju, Ying-Chen; Wang, Lai-You; Xu, Jun; Yang, De-Po; Lan, Wen-Jian; Organic Letters; vol. 17; nb. 21; (2015); p. 5156 - 5159, View in Reaxys 5 of 36

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Luo, Yang-Hui; Sun, Bai-Wang; CrystEngComm; vol. 15; nb. 37; (2013); p. 7490 - 7497, View in Reaxys; Yoo, WooJin; Nguyen, Thanh V. Q.; Guiteras Capdevila, Montse; Kobayashi, Shu; Heterocycles; vol. 90; nb. 2; (2015); p.

1196 - 1204, View in Reaxys 6 of 36

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H

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Coupling Nuclei

1H

Solvents (NMR Spectro- [(2)H6]acetone scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Ouyang, Xuan-Hui; Song, Ren-Jie; Wang, Cheng-Yong; Yang, Yuan; Li, Jin-Heng; Chemical Communications; vol. 51; nb. 77; (2015); p. 14497 - 14500, View in Reaxys 7 of 36

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- [(2)H6]acetone scopy) Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Ouyang, Xuan-Hui; Song, Ren-Jie; Wang, Cheng-Yong; Yang, Yuan; Li, Jin-Heng; Chemical Communications; vol. 51; nb. 77; (2015); p. 14497 - 14500, View in Reaxys 8 of 36

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

600

Yan, Xu; Xue-Ping, Sun; Xiu-Guo, Zhang; Wan-Ping, Tong; Chemistry of Natural Compounds; vol. 51; nb. 4; (2015); p. 800 - 802; Khim. Prir. Soedin.; nb. 4; (2015); p. 683 - 684,2, View in Reaxys 9 of 36

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

150

Yan, Xu; Xue-Ping, Sun; Xiu-Guo, Zhang; Wan-Ping, Tong; Chemistry of Natural Compounds; vol. 51; nb. 4; (2015); p. 800 - 802; Khim. Prir. Soedin.; nb. 4; (2015); p. 683 - 684,2, View in Reaxys 10 of 36

Description (NMR Spec- COSY (Correlation Spectroscopy); Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H; 1H

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Location

supporting information

Liu, Wei; Li, Hou-Jin; Xu, Meng-Yang; Ju, Ying-Chen; Wang, Lai-You; Xu, Jun; Yang, De-Po; Lan, Wen-Jian; Organic Letters; vol. 17; nb. 21; (2015); p. 5156 - 5159, View in Reaxys 11 of 36

Description (NMR Spec- HMBC (Heteronuclear Multiple Bond Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H; 13C

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Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Location

supporting information

Liu, Wei; Li, Hou-Jin; Xu, Meng-Yang; Ju, Ying-Chen; Wang, Lai-You; Xu, Jun; Yang, De-Po; Lan, Wen-Jian; Organic Letters; vol. 17; nb. 21; (2015); p. 5156 - 5159, View in Reaxys 12 of 36

Description (NMR Spec- HMQC (Heteronuclear Multiple Quantum Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H; 13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Location

supporting information

Liu, Wei; Li, Hou-Jin; Xu, Meng-Yang; Ju, Ying-Chen; Wang, Lai-You; Xu, Jun; Yang, De-Po; Lan, Wen-Jian; Organic Letters; vol. 17; nb. 21; (2015); p. 5156 - 5159, View in Reaxys 13 of 36

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- d(4)-methanol scopy) Frequency (NMR Spectroscopy) [MHz]

500

Sun, Jian Fan; Wu, Yi; Yang, Bin; Liu, Yonghong; Chemistry of Natural Compounds; vol. 51; nb. 5; (2015); p. 975 - 977; Khim. Prir. Soedin.; nb. 5; (2015); p. 836 - 837,2, View in Reaxys 14 of 36

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- d(4)-methanol scopy) Frequency (NMR Spectroscopy) [MHz]

125

Sun, Jian Fan; Wu, Yi; Yang, Bin; Liu, Yonghong; Chemistry of Natural Compounds; vol. 51; nb. 5; (2015); p. 975 - 977; Khim. Prir. Soedin.; nb. 5; (2015); p. 836 - 837,2, View in Reaxys 15 of 36

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- deuteromethanol scopy) Frequency (NMR Spectroscopy) [MHz]

600

Location

supporting information

Tian, Shouzheng; Yang, Yabin; Liu, Kai; Xiong, Zijun; Xu, Lihua; Zhao, Lixing; Natural Product Research; vol.

28; nb. 5; (2014); p. 344 - 346, View in Reaxys 16 of 36

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- deuteromethanol scopy)

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Frequency (NMR Spectroscopy) [MHz]

150

Location

supporting information

Tian, Shouzheng; Yang, Yabin; Liu, Kai; Xiong, Zijun; Xu, Lihua; Zhao, Lixing; Natural Product Research; vol.

28; nb. 5; (2014); p. 344 - 346, View in Reaxys 17 of 36

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Miles, Kelsey C.; Le, Chi; Stambuli, James P.; Chemistry--A European Journal; vol. 20; nb. 36; (2014); p. 11336 11339,4, View in Reaxys 18 of 36

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Vandersteen, Adelle A.; Mundle, Scott O.C.; Kluger, Ronald; Journal of Organic Chemistry; vol. 77; nb. 15; (2012); p. 6505 - 6509, View in Reaxys 19 of 36

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Wang, Yu; Haemaelaeinen, Antti; Tois, Jan; Franzen, Robert; Tetrahedron Asymmetry; vol. 21; nb. 19; (2010); p.

2376 - 2384, View in Reaxys 20 of 36

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

75

Wang, Yu; Haemaelaeinen, Antti; Tois, Jan; Franzen, Robert; Tetrahedron Asymmetry; vol. 21; nb. 19; (2010); p.

2376 - 2384, View in Reaxys 21 of 36

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

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Solvents (NMR Spectro- [(2)H6]acetone scopy) Frequency (NMR Spectroscopy) [MHz]

400

Xiao, Hai-Tao; Liu, Bin; Hao, Xiao-Yan; Yang, Xiao-Sheng; Sun, Qian-Yun; Chemistry of Natural Compounds; vol. 45; nb. 4; (2009); p. 539 - 541, View in Reaxys 22 of 36

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- [(2)H6]acetone scopy) Frequency (NMR Spectroscopy) [MHz]

100

Xiao, Hai-Tao; Liu, Bin; Hao, Xiao-Yan; Yang, Xiao-Sheng; Sun, Qian-Yun; Chemistry of Natural Compounds; vol. 45; nb. 4; (2009); p. 539 - 541, View in Reaxys 23 of 36

Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Original Text (NMR Spectroscopy)

The 1H-NMR of purified eight IAA samples was found to be same as that of 1H-NMR of standard IAA (FIG. 4). The first peak from right is of acid, of value 9.0 δ bs (-OH), lateral peaks are of protons having values 7.8 δ d 1H (C8H), 7.5 δ d 1H (C5H), 7.31δ d 1H (C2H) and 7.07 δ m 2H (C6 C&7H). Middle big peak is of DMSO having value of 3.04 δ S (d6) and moisture. The next peak is of carbon and hydrogen, having value of 2.59 δ S 2H (-CH2-) and last peak is of internal standard, tetra-methyl-silnate (TMS) of value 0.08.

Comment (NMR Spectroscopy)

Signals given

Patent; Council of Scientific and Industrial Research; US2005/70435; (2005); (A1) English, View in Reaxys 24 of 36

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Schallenberg, Juergen; Meyer, Eckart; Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie; vol. 38; nb. 1; (1983); p. 108 - 112, View in Reaxys; Tan, Jianwen; Bednarek, Pawel; Liu, Jikai; Schneider, Bernd; Svatos, Ales; Hahlbrock, Klaus; Phytochemistry; vol. 65; nb. 6; (2004); p. 691 - 699, View in Reaxys 25 of 36

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Tan, Jianwen; Bednarek, Pawel; Liu, Jikai; Schneider, Bernd; Svatos, Ales; Hahlbrock, Klaus; Phytochemistry; vol. 65; nb. 6; (2004); p. 691 - 699, View in Reaxys 26 of 36

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Hoshino, Tsutomu; Yamamoto, Masahiro; Uchiyama, Takeo; Bioscience, Biotechnology, and Biochemistry; vol.

57; nb. 9; (1993); p. 1609 - 1610, View in Reaxys; Guella; Mancini; N'Diaye; Pietra; Helvetica Chimica Acta; vol. 77;

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nb. 7; (1994); p. 1999 - 2006, View in Reaxys; Yoshida, Toyokazu; Fujita, Kohei; Nagasawa, Toru; Bioscience, Biotechnology and Biochemistry; vol. 66; nb. 11; (2002); p. 2388 - 2394, View in Reaxys 27 of 36

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Hoshino, Tsutomu; Yamamoto, Masahiro; Uchiyama, Takeo; Bioscience, Biotechnology, and Biochemistry; vol.

57; nb. 9; (1993); p. 1609 - 1610, View in Reaxys; Guella; Mancini; N'Diaye; Pietra; Helvetica Chimica Acta; vol. 77; nb. 7; (1994); p. 1999 - 2006, View in Reaxys; Yoshida, Toyokazu; Fujita, Kohei; Nagasawa, Toru; Bioscience, Biotechnology and Biochemistry; vol. 66; nb. 11; (2002); p. 2388 - 2394, View in Reaxys 28 of 36

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

1H

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Yoshida, Toyokazu; Fujita, Kohei; Nagasawa, Toru; Bioscience, Biotechnology and Biochemistry; vol. 66; nb. 11; (2002); p. 2388 - 2394, View in Reaxys 29 of 36

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Temperature (NMR Spectroscopy) [°C]

30

Sakurai; Kohno; Nishio; Yamamoto; Okuda; Kawano; Nakanishi; Journal of Antibiotics; vol. 54; nb. 8; (2001); p.

628 - 634, View in Reaxys 30 of 36

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- dimethylsulfoxide-d6; various solvent(s) scopy) Vijayakumar; Roy, Kirity; Chatterjee, Sugata; Deshmukh; Ganguli; Fehlhaber; Kogler; Journal of Organic Chemistry; vol. 61; nb. 19; (1996); p. 6591 - 6593, View in Reaxys 31 of 36

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6; various solvent(s) scopy) Vijayakumar; Roy, Kirity; Chatterjee, Sugata; Deshmukh; Ganguli; Fehlhaber; Kogler; Journal of Organic Chemistry; vol. 61; nb. 19; (1996); p. 6591 - 6593, View in Reaxys 32 of 36

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Comment (NMR Spectroscopy)

1H-1H. Solvent(s): further solvent(s)

Vijayakumar; Roy, Kirity; Chatterjee, Sugata; Deshmukh; Ganguli; Fehlhaber; Kogler; Journal of Organic Chemistry; vol. 61; nb. 19; (1996); p. 6591 - 6593, View in Reaxys 33 of 36

Description (NMR Spec- Spin-spin coupling constants troscopy)

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Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Comment (NMR Spectroscopy)

1H-1H

Hoshino, Tsutomu; Yamamoto, Masahiro; Uchiyama, Takeo; Bioscience, Biotechnology, and Biochemistry; vol.

57; nb. 9; (1993); p. 1609 - 1610, View in Reaxys; Guella; Mancini; N'Diaye; Pietra; Helvetica Chimica Acta; vol. 77; nb. 7; (1994); p. 1999 - 2006, View in Reaxys 34 of 36

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

1H

Solvents (NMR Spectro- acetone-d6 scopy) Chiji, Hideyuki; Arakawa, Yoshihito; Ueda, Shinji; Kuroda, Mutsumi; Izawa, Masao; Phytochemistry (Elsevier); vol. 25; nb. 1; (1986); p. 281 - 282, View in Reaxys 35 of 36

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3; tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]

27

Burton, Gerardo; Ghini, Alberto A.; Gros, Eduardo G.; Magnetic Resonance in Chemistry; vol. 24; (1986); p. 829 - 831, View in Reaxys 36 of 36

Description (NMR Spec- NMR troscopy) Jardine; Brown; Canadian Journal of Chemistry; vol. 41; (1963); p. 2067,2069, View in Reaxys; Mackie et al.; Journal of Fluorine Chemistry; vol. 10; (1977); p. 437,442, View in Reaxys

IR Spectroscopy (9) 1 of 9

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Luo, Yang-Hui; Sun, Bai-Wang; CrystEngComm; vol. 15; nb. 37; (2013); p. 7490 - 7497, View in Reaxys; Sun, Jian Fan; Wu, Yi; Yang, Bin; Liu, Yonghong; Chemistry of Natural Compounds; vol. 51; nb. 5; (2015); p. 975 - 977; Khim.

Prir. Soedin.; nb. 5; (2015); p. 836 - 837,2, View in Reaxys 2 of 9

Description (IR Spectroscopy)

Bands; Spectrum

Mandal, Gopa; Bhattacharya, Sudeshna; Chowdhury, Joydeep; Ganguly, Tapan; Journal of Molecular Structure; vol. 964; nb. 1-3; (2010); p. 9 - 17, View in Reaxys 3 of 9

Original Text (IR Spectroscopy)

The IR spectrum of pure IAA showed OH frequency at 3384.9 cm-1 and CO frequency at 1698.4 cm-1 (FIG. 3). IR spectrum of standard IAA also showed same results

Patent; Council of Scientific and Industrial Research; US2005/70435; (2005); (A1) English, View in Reaxys 4 of 9

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Yoshida, Toyokazu; Fujita, Kohei; Nagasawa, Toru; Bioscience, Biotechnology and Biochemistry; vol. 66; nb. 11; (2002); p. 2388 - 2394, View in Reaxys 5 of 9

Description (IR Spectroscopy)

Bands

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Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1640 cm**(-1)

Chiji, Hideyuki; Arakawa, Yoshihito; Ueda, Shinji; Kuroda, Mutsumi; Izawa, Masao; Phytochemistry (Elsevier); vol. 25; nb. 1; (1986); p. 281 - 282, View in Reaxys 6 of 9

Description (IR Spectroscopy)

IR

Golubey; Suvorov; Khimiya Geterotsiklicheskikh Soedinenii, Sbornik; (1967); p. 21,22-24; Chem.Abstr.; vol. 70; nb.

77700f; (1969), View in Reaxys 7 of 9

Description (IR Spectroscopy)

Bands

Porter; Thimann; Phytochemistry (Elsevier); vol. 4; (1965); p. 229,235, View in Reaxys 8 of 9

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

3510 - 720 cm**(-1)

Fawcett et al.; Proceedings of the Royal Society of London, Series B: Biological Sciences; vol. 148; (1958); p. 543,547, View in Reaxys 9 of 9

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3390 - 1240 cm**(-1)

Millich; Becker; Journal of Organic Chemistry; vol. 23; (1958); p. 1096,1097, View in Reaxys Mass Spectrometry (16) Description (Mass Location Spectrometry)

Comment (Mass Spectrometry)

References

electrospray ioni- supporting inforsation (ESI); spec- mation trum

Fei, Peng; Wang, Chuan-Xi; Yang, Xie; Jiang, Hong-Lei; Chen, LuJie; Uribe, Paulina; Bull, Alan T.; Goodfellow, Michael; Hong, Jiang; Lian, Yun-Yang; Natural Product Research; vol. 27; nb. 15; (2013); p. 1366 - 1371, View in Reaxys; Tian, Shouzheng; Yang, Yabin; Liu, Kai; Xiong, Zijun; Xu, Lihua; Zhao, Lixing; Natural Product Research; vol. 28; nb. 5; (2014); p. 344 - 346, View in Reaxys; Liu, Wei; Li, Hou-Jin; Xu, Meng-Yang; Ju, Ying-Chen; Wang, Lai-You; Xu, Jun; Yang, De-Po; Lan, Wen-Jian; Organic Letters; vol. 17; nb.

21; (2015); p. 5156 - 5159, View in Reaxys

tandem mass spectrometry; spectrum

Yu, Xinyu; Luo, Jia; Chen, Lijun; Zhang, Chengxiang; Zhang, Rutan; Hu, Qi; Qiao, Shanlei; Li, Lei; RSC Advances; vol. 5; nb. 85; (2015); p. 69800 - 69812, View in Reaxys

electrospray ionisation (ESI); spectrum

Yan, Xu; Xue-Ping, Sun; Xiu-Guo, Zhang; Wan-Ping, Tong; Chemistry of Natural Compounds; vol. 51; nb. 4; (2015); p. 800 - 802; Khim.

Prir. Soedin.; nb. 4; (2015); p. 683 - 684,2, View in Reaxys; Sun, Jian Fan; Wu, Yi; Yang, Bin; Liu, Yonghong; Chemistry of Natural Compounds; vol. 51; nb. 5; (2015); p. 975 - 977; Khim. Prir. Soedin.; nb. 5; (2015); p. 836 - 837,2, View in Reaxys

electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum

Strehmel, Nadine; Böttcher, Christoph; Schmidt, Stephan; Scheel, Dierk; Phytochemistry; vol. 108; (2014); p. 35 - 46, View in Reaxys

CID (collision-induced dissociation); spectrum

Strehmel, Nadine; Böttcher, Christoph; Schmidt, Stephan; Scheel, Dierk; Phytochemistry; vol. 108; (2014); p. 35 - 46, View in Reaxys

electron impact (EI); spectrum

Chiji, Hideyuki; Arakawa, Yoshihito; Ueda, Shinji; Kuroda, Mutsumi; Izawa, Masao; Phytochemistry (Elsevier); vol. 25; nb. 1; (1986); p.

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281 - 282, View in Reaxys; Zhang, Qi; Guo, Wen-Juan; Fu, ChangLiang; Ma, Shuang; Zhu, Mei-Qin; Chemistry of Natural Compounds; vol. 49; nb. 1; (2013); p. 117 - 118; Khim. Prir. Soedin.; nb. 0023-1150; p. 2, View in Reaxys HRMS (High resolution mass spectrometry); ESI (Electrospray ionisation); Negative ion spectroscopy; TOFMS (Time of flight mass spectrum); Spectrum

Upreti, Mani; Somayajula, Kasi V.; Milanowski, Dennis J.; Kowalenko, Peter; Mocek, Ulla; Miguel, Rafael San; Prakash, Indra; Food Chemistry; vol. 131; nb. 2; (2012); p. 413 - 421, View in Reaxys

ESI (Electrospray ionisation); TOFMS (Time of flight mass spectrum); Tandem mass spectrometry; Spectrum

Upreti, Mani; Somayajula, Kasi V.; Milanowski, Dennis J.; Kowalenko, Peter; Mocek, Ulla; Miguel, Rafael San; Prakash, Indra; Food Chemistry; vol. 131; nb. 2; (2012); p. 413 - 421, View in Reaxys

ESI (Electrospray ionisation); Negative ion spectroscopy; Spectrum

Upreti, Mani; Somayajula, Kasi V.; Milanowski, Dennis J.; Kowalenko, Peter; Mocek, Ulla; Miguel, Rafael San; Prakash, Indra; Food Chemistry; vol. 131; nb. 2; (2012); p. 413 - 421, View in Reaxys

LCMS (Liquid chromatography mass spectrometry); ESI (Electrospray ionisation); Spectrum

Upreti, Mani; Somayajula, Kasi V.; Milanowski, Dennis J.; Kowalenko, Peter; Mocek, Ulla; Miguel, Rafael San; Prakash, Indra; Food Chemistry; vol. 131; nb. 2; (2012); p. 413 - 421, View in Reaxys

HRMS (High resolution mass spectrometry); ESI (Electrospray ionisation); Spectrum

Shilpi, Jamil A.; Gray, Alexander I.; Seidel, Veronique; Fitoterapia; vol. 81; nb. 6; (2010); p. 536 - 539, View in Reaxys

EI (Electron impact); Spectrum

Xiao, Hai-Tao; Liu, Bin; Hao, Xiao-Yan; Yang, Xiao-Sheng; Sun, Qian-Yun; Chemistry of Natural Compounds; vol. 45; nb. 4; (2009); p.

539 - 541, View in Reaxys; Nakabayashi, Ryo; Kusano, Miyako; Kobayashi, Makoto; Tohge, Takayuki; Yonekura-Sakakibara, Keiko; Kogure, Noriyuki; Yamazaki, Mami; Kitajima, Mariko; Saito, Kazuki; Takayama, Hiromitsu; Phytochemistry; vol. 70; nb. 8; (2009); p.

1017 - 1029, View in Reaxys

spectrum; electron impact (EI)

Tan, Jianwen; Bednarek, Pawel; Liu, Jikai; Schneider, Bernd; Svatos, Ales; Hahlbrock, Klaus; Phytochemistry; vol. 65; nb. 6; (2004); p. 691 - 699, View in Reaxys

spectrum

FAB (fast atom bombardment)

spectrum

Guella; Mancini; N'Diaye; Pietra; Helvetica Chimica Acta; vol. 77; nb.

7; (1994); p. 1999 - 2006, View in Reaxys Schallenberg, Juergen; Meyer, Eckart; Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie; vol. 38; nb. 1; (1983); p. 108 - 112, View in Reaxys Powers; Journal of Organic Chemistry; vol. 33; nb. 5; (1968); p. 2044, View in Reaxys; Jamieson; Hutzinger; Phytochemistry (Elsevier); vol. 9; (1970); p. 2029,2033, View in Reaxys

UV/VIS Spectroscopy (19) 1 of 19

Description (UV/VIS Spectroscopy)

Spectrum

Absorption Maxima (UV/ 278 VIS) [nm] Cao, Hongnan; Hall, James; Hille, Russ; Biochemistry; vol. 53; nb. 3; (2014); p. 533 - 541, View in Reaxys 2 of 19

Description (UV/VIS Spectroscopy)

Spectrum

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Location

supporting information

Vandersteen, Adelle A.; Mundle, Scott O.C.; Kluger, Ronald; Journal of Organic Chemistry; vol. 77; nb. 15; (2012); p. 6505 - 6509, View in Reaxys 3 of 19

Solvent (UV/VIS Spectroscopy)

ethanol

Absorption Maxima (UV/ 214; 281 VIS) [nm] Nakabayashi, Ryo; Kusano, Miyako; Kobayashi, Makoto; Tohge, Takayuki; Yonekura-Sakakibara, Keiko; Kogure, Noriyuki; Yamazaki, Mami; Kitajima, Mariko; Saito, Kazuki; Takayama, Hiromitsu; Phytochemistry; vol. 70; nb. 8; (2009); p. 1017 - 1029, View in Reaxys 4 of 19

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

H2O

Absorption Maxima (UV/ 232; 274 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

17220; 3590

Linares, R. M.; Gonzalez, A.; Ayala, J. H.; Afonso, A. M.; Gonzalez, Venerando; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 51; nb. 10; (1995); p. 1691 - 1702, View in Reaxys 5 of 19

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

H2O

Absorption Maxima (UV/ 233; 278 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

18100; 3680

Linares, R. M.; Gonzalez, A.; Ayala, J. H.; Afonso, A. M.; Gonzalez, Venerando; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 51; nb. 10; (1995); p. 1691 - 1702, View in Reaxys 6 of 19

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

H2O

Absorption Maxima (UV/ 239; 278 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

14720; 4300

Linares, R. M.; Gonzalez, A.; Ayala, J. H.; Afonso, A. M.; Gonzalez, Venerando; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 51; nb. 10; (1995); p. 1691 - 1702, View in Reaxys 7 of 19

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

H2O

Absorption Maxima (UV/ 240; 280 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

16460; 4300

Linares, R. M.; Gonzalez, A.; Ayala, J. H.; Afonso, A. M.; Gonzalez, Venerando; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 51; nb. 10; (1995); p. 1691 - 1702, View in Reaxys 8 of 19

Description (UV/VIS Spectroscopy)

Absorption maxima

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Solvent (UV/VIS Spectroscopy)

methanol; aq. KOH

Comment (UV/VIS Spectroscopy)

Remark: 25.0 deg C

Absorption Maxima (UV/ 277; 303.8; 253.8 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

8710; 7762; 22909

Balon, M.; Munoz, M. A.; Carmona, C.; Hidalgo, J.; Gonzalez, D.; Journal of Chemical Research, Miniprint; nb. 5; (1990); p. 1001 - 1014, View in Reaxys 9 of 19

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

cyclohexane

Absorption Maxima (UV/ 226; 271; 277; 283 VIS) [nm] Krishnamurthy, Mannam; Dogra, Sneh K.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 26; nb. 7; (1987); p. 587 - 591, View in Reaxys 10 of 19

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

H2O

Absorption Maxima (UV/ 212; 278; 285 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

25704; 8912; 8710

Krishnamurthy, Mannam; Dogra, Sneh K.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 26; nb. 7; (1987); p. 587 - 591, View in Reaxys 11 of 19

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

acetonitrile

Absorption Maxima (UV/ 213; 279; 285 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

20417; 7943; 7079

Krishnamurthy, Mannam; Dogra, Sneh K.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 26; nb. 7; (1987); p. 587 - 591, View in Reaxys 12 of 19

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

ethanol

Absorption Maxima (UV/ 214; 279; 285 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

17783; 8318; 7762

Krishnamurthy, Mannam; Dogra, Sneh K.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 26; nb. 7; (1987); p. 587 - 591, View in Reaxys 13 of 19

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

methanol

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Absorption Maxima (UV/ 214; 279; 285 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

17378; 8128; 7762

Krishnamurthy, Mannam; Dogra, Sneh K.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 26; nb. 7; (1987); p. 587 - 591, View in Reaxys 14 of 19

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

diethyl ether

Absorption Maxima (UV/ 224; 272; 277; 284 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

14125; 7943; 8511; 7244

Krishnamurthy, Mannam; Dogra, Sneh K.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 26; nb. 7; (1987); p. 587 - 591, View in Reaxys 15 of 19

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

ethanol

Absorption Maxima (UV/ 212; 280 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

12882; 4169

Chiji, Hideyuki; Arakawa, Yoshihito; Ueda, Shinji; Kuroda, Mutsumi; Izawa, Masao; Phytochemistry (Elsevier); vol. 25; nb. 1; (1986); p. 281 - 282, View in Reaxys 16 of 19

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 280; 286 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

10233; 9550

Schallenberg, Juergen; Meyer, Eckart; Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie; vol. 38; nb. 1; (1983); p. 108 - 112, View in Reaxys 17 of 19

Description (UV/VIS Spectroscopy)

Absorption maxima

Sun; Song; Photochemistry and Photobiology; vol. 25; (1977); p. 3,5, View in Reaxys 18 of 19

Description (UV/VIS Spectroscopy)

UV/VIS

Abe et al.; Agricultural and Biological Chemistry; vol. 36; (1972); p. 2259, View in Reaxys; Dibbern; Rochelmeyer; Arzneimittel Forschung; vol. 13; (1963); p. 7,12,15, View in Reaxys; Joschek; Grossweiner; Journal of the American Chemical Society; vol. 88; (1966); p. 3261,3262, View in Reaxys 19 of 19

Description (UV/VIS Spectroscopy)

Spectrum

Ward; Biochemical Journal; vol. 17; (1923); p. 900, View in Reaxys; Song; Kurtin; Journal of the American Chemical Society; vol. 91; (1969); p. 4892,4893, 4895, 4897, View in Reaxys Luminescence Spectroscopy (3) Description (Lumi- References nescence Spectroscopy) Luminescence quantum yield

Krishnamurthy, Mannam; Dogra, Sneh K.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 26; nb. 7; (1987); p. 587 - 591, View in Reaxys

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Emission spectrum in the infrared region

Song; Kurtin; Journal of the American Chemical Society; vol. 91; (1969); p. 4892,4893, 4895, 4897, View in Reaxys

Luminescence lifetime

Song; Kurtin; Journal of the American Chemical Society; vol. 91; (1969); p. 4892,4893, 4895, 4897, View in Reaxys

Fluorescence Spectroscopy (12) Description (Fluo- Solvent (Fluoresrescence Spectro- cence Spectroscopy) scopy)

Comment (FluoReferences rescence Spectroscopy)

Spectrum

H2O

250 - 500 nm

Linares, R. M.; Gonzalez, A.; Ayala, J. H.; Afonso, A. M.; Gonzalez, Venerando; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 51; nb. 10; (1995); p. 1691 - 1702, View in Reaxys

Spectrum

H2O; various solvent(s)

250 - 500 nm

Linares, R. M.; Gonzalez, A.; Ayala, J. H.; Afonso, A. M.; Gonzalez, Venerando; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 51; nb. 10; (1995); p. 1691 - 1702, View in Reaxys

Maxima

H2O

340 nm; 342 nm; 365 nm; 460 nm

Linares, R. M.; Gonzalez, A.; Ayala, J. H.; Afonso, A. M.; Gonzalez, Venerando; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 51; nb. 10; (1995); p. 1691 - 1702, View in Reaxys

Maxima

H2O; various solvent(s)

340 nm; 349 nm; 370 nm; 450 nm

Linares, R. M.; Gonzalez, A.; Ayala, J. H.; Afonso, A. M.; Gonzalez, Venerando; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 51; nb. 10; (1995); p. 1691 - 1702, View in Reaxys

Maxima

H2O; various solvent(s)

340 nm; 357 nm; 365 nm; 438 nm

Linares, R. M.; Gonzalez, A.; Ayala, J. H.; Afonso, A. M.; Gonzalez, Venerando; Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy; vol. 51; nb. 10; (1995); p. 1691 - 1702, View in Reaxys

Maxima

cyclohexane

308 nm

Krishnamurthy, Mannam; Dogra, Sneh K.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 26; nb. 7; (1987); p. 587 - 591, View in Reaxys

Maxima

diethyl ether

318 nm

Krishnamurthy, Mannam; Dogra, Sneh K.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 26; nb. 7; (1987); p. 587 - 591, View in Reaxys

Maxima

acetonitrile

321 nm

Krishnamurthy, Mannam; Dogra, Sneh K.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 26; nb. 7; (1987); p. 587 - 591, View in Reaxys

Maxima

methanol

329 nm

Krishnamurthy, Mannam; Dogra, Sneh K.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 26; nb. 7; (1987); p. 587 - 591, View in Reaxys

Maxima

ethanol

332 nm

Krishnamurthy, Mannam; Dogra, Sneh K.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 26; nb. 7; (1987); p. 587 - 591, View in Reaxys

Maxima

H2O

346 nm

Krishnamurthy, Mannam; Dogra, Sneh K.; Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical; vol. 26; nb. 7; (1987); p. 587 - 591, View in Reaxys

Fluorescence

Sun; Song; Photochemistry and Photobiology; vol. 25; (1977); p. 3,5, View in Reaxys

Other Spectroscopic Methods (1) Description (Other References Spectroscopic Methods) Photoelectron spectrum

Redchenko et al.; Theoretical and Experimental Chemistry; vol. 14; (1978); p. 653; ; p. 841, View in Reaxys

Pharmacological Data (80) 1 of 80

Comment (Pharmacological Data)

Bioactivities present

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Yue, Jia-Rui; Feng, De-Qiang; Xu, You-Kai; Natural Product Research; vol. 29; nb. 13; (2015); p. 1228 - 1234, View in Reaxys 3 of 80

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Le, Jiamei; Lu, Wenquan; Xiong, Xiaojuan; Wu, Zhijun; Chen, Wansheng; Molecules; vol. 20; nb. 10; (2015); p.

18496 - 18510, View in Reaxys 4 of 80

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Tian, Shouzheng; Yang, Yabin; Liu, Kai; Xiong, Zijun; Xu, Lihua; Zhao, Lixing; Natural Product Research; vol.

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Comment (Pharmacological Data)

physiological behaviour discussed

Behrens, Maik; Frank, Oliver; Rawel, Harshadrai; Ahuja, Gaurav; Potting, Christoph; Hofmann, Thomas; Meyerhof, Wolfgang; Korsching, Sigrun; Journal of Biological Chemistry; vol. 289; nb. 28; (2014); p. 19778 - 19788, View in Reaxys 6 of 80

Comment (Pharmacological Data)

physiological behaviour discussed

Patent; NANYANG TECHNOLOGICAL UNIVERSITY; NATIONAL UNIVERSITY OF SINGAPORE; GIVSKOV, Michael; YANG, Liang; TAN, Yang Yi, Sean; WO2014/142748; (2014); (A1) English, View in Reaxys

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7 of 80

Comment (Pharmacological Data)

physiological behaviour discussed

Patent; ALEVERE MEDICAL CORPORATION; DUNCAN, Diane; KAMERZELL, Tim; PALMER, Mark, A.; WO2014/143125; (2014); (A1) English, View in Reaxys 8 of 80

Comment (Pharmacological Data)

physiological behaviour discussed

Perez-Chacon, Gema; De Los Rios, Cristobal; Zapata, Juan M.; Pharmacological Research; vol. 89; (2014); p. 46 - 56, View in Reaxys 9 of 80

Effect (Pharmacological Data)

receptor; activation of

Species or Test-System (Pharmacological Data)

HEK293TGα16gust44 cells of human; genetically modified/infected with: human taste 2 receptor 39

Concentration (Pharmacological Data)

<= 1 mmol/l

Method (Pharmacological Data)

name of assay/method: spectrofluorometric assay using calcium-sensitive dye Fluo-4-AM

Further Details (Pharma- HEK293TGα16gust44: HEK293T embryonic kidney cells stably expressing the chimeric Gcological Data) protein α-subunit Gα16-Gust44; Results

no effect (related to human taste 2 receptor 39)

Kohl, Susann; Behrens, Maik; Dunkel, Andreas; Hofmann, Thomas; Meyerhof, Wolfgang; Journal of Agricultural and Food Chemistry; vol. 61; nb. 1; (2013); p. 53 - 60, View in Reaxys 10 of 80

Effect (Pharmacological Data)

receptor; activation of

Species or Test-System (Pharmacological Data)

HEK293TGα16gust44 cells of human; genetically modified/infected with: human taste 2 receptor 4

Concentration (Pharmacological Data)

<= 1 mmol/l

Method (Pharmacological Data)

name of assay/method: spectrofluorometric assay using calcium-sensitive dye Fluo-4-AM

Further Details (Pharma- HEK293TGα16gust44: HEK293T embryonic kidney cells stably expressing the chimeric Gcological Data) protein α-subunit Gα16-Gust44; Results

no effect (related to human taste 2 receptor 4)

Kohl, Susann; Behrens, Maik; Dunkel, Andreas; Hofmann, Thomas; Meyerhof, Wolfgang; Journal of Agricultural and Food Chemistry; vol. 61; nb. 1; (2013); p. 53 - 60, View in Reaxys 11 of 80

Effect (Pharmacological Data)

antimycobacterial

Species or Test-System (Pharmacological Data)

Mycobacterium tuberculosis H37Rv

Further Details (Pharma- minimal inhibitory concentration (MIC) cological Data) Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

>621 μmol/l

Wu, Ming-Der; Cheng, Ming-Jen; Chen, Ih-Sheng; Su, Yung-Shun; Hsieh, Sung-Yuan; Chang, Hsun-Shuo; Chang, Chun-Wei; Yuan, Gwo-Fang; Chemistry and Biodiversity; vol. 10; nb. 3; (2013); p. 493 - 505, View in Reaxys 12 of 80

Comment (Pharmacological Data)

physiological behaviour discussed

Pedras, M. Soledade C.; Abdoli, Abbas; Bioorganic and Medicinal Chemistry; vol. 21; nb. 15; (2013); p. 4541 - 4549, View in Reaxys 13 of 80

Comment (Pharmacological Data)

physiological behaviour discussed

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Fei, Peng; Wang, Chuan-Xi; Yang, Xie; Jiang, Hong-Lei; Chen, Lu-Jie; Uribe, Paulina; Bull, Alan T.; Goodfellow, Michael; Hong, Jiang; Lian, Yun-Yang; Natural Product Research; vol. 27; nb. 15; (2013); p. 1366 - 1371, View in Reaxys 14 of 80

Comment (Pharmacological Data)

physiological behaviour discussed

Tan, Sean Yang-Yi; Chua, Song-Lin; Chen, Yicai; Rice, Scott A.; Kjelleberg, Staffan; Nielsen, Thomas E.; Yang, Liang; Givskov, Michael; Antimicrobial Agents and Chemotherapy; vol. 57; nb. 11; (2013); p. 5629 - 5641, View in Reaxys 15 of 80

Effect (Pharmacological Data)

cytotoxic

Species or Test-System (Pharmacological Data)

3T3-L1 adipocyte

Concentration (Pharmacological Data)

<= 30 μmol/l

Kind of Dosing (Pharma- title comp. dissolved in DMSO cological Data) Further Details (Pharma- 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay cological Data) Results

no effect

Yahagi, Tadahiro; Daikonya, Akihiro; Kitanaka, Susumu; Chemical and Pharmaceutical Bulletin; vol. 60; nb. 1; (2012); p. 129 - 136, View in Reaxys 16 of 80

Effect (Pharmacological Data)

glucose uptake; inhibition of

Species or Test-System (Pharmacological Data)

3T3-L1 adipocyte

Kind of Dosing (Pharma- title comp. dissolved in DMSO cological Data) Further Details (Pharma- liquid scintillation counting using [1-(3H)]-2-deoxy-D-glucose cological Data) Type (Pharmacological Data)

inhibition rate

Value of Type (Pharmacological Data)

11.8 percent

Yahagi, Tadahiro; Daikonya, Akihiro; Kitanaka, Susumu; Chemical and Pharmaceutical Bulletin; vol. 60; nb. 1; (2012); p. 129 - 136, View in Reaxys 17 of 80

Effect (Pharmacological Data)

triglyceride accumulation; inhibition of

Species or Test-System (Pharmacological Data)

3T3-L1 adipocyte

Concentration (Pharmacological Data)

30 μmol/l

Kind of Dosing (Pharma- title comp. dissolved in DMSO cological Data) Type (Pharmacological Data)

inhibition rate

Value of Type (Pharmacological Data)

25.2 percent

Yahagi, Tadahiro; Daikonya, Akihiro; Kitanaka, Susumu; Chemical and Pharmaceutical Bulletin; vol. 60; nb. 1; (2012); p. 129 - 136, View in Reaxys 18 of 80

Effect (Pharmacological Data)

ald gene expression; increase of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

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Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concentration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = 1.709603089 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 19 of 80

Effect (Pharmacological Data)

atpF gene expression; decrease of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concen-

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tration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = -0.83061618 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 20 of 80

Effect (Pharmacological Data)

atpH gene expression; decrease of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concentration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random

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2016-03-08 21:02:53

hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = -0.72807496 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 21 of 80

Effect (Pharmacological Data)

cyaD2 gene expression; increase of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concentration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = 1.011985231 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 22 of 80

Effect (Pharmacological Data)

degP4 gene expression; increase of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

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Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concentration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = 1.148294032 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 23 of 80

Effect (Pharmacological Data)

flaA gene expression; decrease of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concen-

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tration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = -0.71144865 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 24 of 80

Effect (Pharmacological Data)

flgG gene expression; decrease of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concentration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random

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2016-03-08 21:02:53

hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = -0.75006865 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 25 of 80

Effect (Pharmacological Data)

groEL1 gene expression; decrease of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concentration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = -0.83494684 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 26 of 80

Effect (Pharmacological Data)

groES1 gene expression; decrease of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

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2016-03-08 21:02:53

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concentration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = -1.49142677 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 27 of 80

Effect (Pharmacological Data)

hspC2 gene expression; increase of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concen-

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43/75

2016-03-08 21:02:53

tration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = 1.111188207 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 28 of 80

Effect (Pharmacological Data)

htpG gene expression; increase of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concentration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random

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44/75

2016-03-08 21:02:53

hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = 0.7619012 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 29 of 80

Effect (Pharmacological Data)

ibpA gene expression; increase of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concentration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = 1.473713787 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 30 of 80

Effect (Pharmacological Data)

nex18 gene expression; increase of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

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2016-03-08 21:02:53

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concentration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = 0.993757572 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 31 of 80

Effect (Pharmacological Data)

pilA1 gene expression; decrease of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concen-

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46/75

2016-03-08 21:02:53

tration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = -0.72744163 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 32 of 80

Effect (Pharmacological Data)

rplC gene expression; decrease of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concentration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random

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2016-03-08 21:02:53

hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = -0.75579918 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 33 of 80

Effect (Pharmacological Data)

rpsA gene expression; decrease of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concentration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = -0.776312 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 34 of 80

Effect (Pharmacological Data)

rpsO gene expression; decrease of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

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2016-03-08 21:02:53

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concentration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = -0.72195502 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 35 of 80

Effect (Pharmacological Data)

smc00514 gene expression; increase of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concen-

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49/75

2016-03-08 21:02:53

tration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = 0.872057618 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 36 of 80

Effect (Pharmacological Data)

smc00537 gene expression; increase of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concentration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random

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50/75

2016-03-08 21:02:53

hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = 0.958342276 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 37 of 80

Effect (Pharmacological Data)

smc01534 gene expression; increase of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concentration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = 0.927685887 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 38 of 80

Effect (Pharmacological Data)

smc01793 gene expression; decrease of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

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2016-03-08 21:02:53

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concentration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = -0.76252145 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 39 of 80

Effect (Pharmacological Data)

smc02603 gene expression; increase of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concen-

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52/75

2016-03-08 21:02:53

tration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = 1.484428133 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 40 of 80

Effect (Pharmacological Data)

smc03168 gene expression; increase of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concentration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random

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2016-03-08 21:02:53

hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = 1.005018738 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 41 of 80

Effect (Pharmacological Data)

smc03253 gene expression; increase of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concentration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = 1.14006745 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 42 of 80

Effect (Pharmacological Data)

smc03829 gene expression; increase of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

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2016-03-08 21:02:53

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concentration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = 0.906503799 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 43 of 80

Effect (Pharmacological Data)

smc04140 gene expression; increase of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concen-

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55/75

2016-03-08 21:02:53

tration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = 1.126173329 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 44 of 80

Effect (Pharmacological Data)

tufB gene expression; decrease of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concentration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

56/75

2016-03-08 21:02:53

hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = -0.87682266 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 45 of 80

Effect (Pharmacological Data)

virB9 gene expression; increase of

Species or Test-System (Pharmacological Data)

S. meliloti 1021

Method (Pharmacological Data)

MATERIALS AND METHODS Bacterial Growth Conditions [0036] The S. meliloti wild type 1021 strain and the IAA-overproducing RD64 strain containing the p-iaaMtms2 construct were previously described (12, 21). Standard mannitol minimal medium for rhizobium (RMM) (19) was modified to contain 1percent (w/v) mannitol as carbon source, 1percent (w/v) ammonium chloride, 10 mM morpholine propanesulfonic acid (MOPS; pH 7.0) to buffer and P (KH2PO4) added to a final concentration of 1 mM (P-starvation) and 13 mM (P-sufficient).

Antibiotics were included as required (5). P-Depletion [0037] For P starvation experiments, cells of 1021 wild-type and RD64 strains were grown at 30° C. to mid exponential phase (OD600=0.6) in RMM broth containing 1percent (w/v) mannitol as carbon source and 13 mM P, washed with RMM containing 0 P, resuspended in the same medium and then divided into three cultures. No P (-P), 1.0 mM P (P-starved cells) or 13 mM P (+P cells also named P-sufficient cells) was added into the three cultures, respectively. The P-starved and Psufficient 1021 wild type cells were treated for 3.0 hours with 0.5 mM IAA. To test the specificity of IAA-effects, other four selected compounds [indole (Ind), tryptophan (Trp), indole-3carboxylic acid (ICA) and 2,4-dichlorophenoxyacetic acid (2,4-D)], whose acidity covers a range that goes from the acid (pH 2.9) to the weak acid (pH 6.1), were dissolved in 50percent (w/v) ethanol and added to P-starved and P-sufficient 1021 wild type cells to a final concentration of 0.5 mM. The newly introduced IAA biosynthetic pathway use Trp to produce IAA, thus opening the question of whether the RD64 cells are Trp starved. Indeed, as the authors introduced in the bacteria two new genes that convert Trp into IAA, the two genes might be very efficient so that as soon as a molecule of Trp is around they convert it into IAA and there is no Trp to be included into the protein synthesis. To rule out that this bacteria could be partially starved for Trp, RD64 cells were also treated with 0.5 mM Trp and used for microarrays and RT-PCR analyses. Finally, to avoid solvent interference, control cells were treated with similar amount of ethanol solution. After 3 hours of each treatment, cell batches were collected, freezed and stored at -80° C. for use in experiments. [0038] For phosphate solubilization experiments 5percent Moroccan phosphate rock (PR) (Sigma-Aldrich, cat. No. 32) was used as P source. When 5percent PR is used as P source to allow bacterial growth this is described as a P-limiting condition. At least five independent experiments were always performed. Microarray Analysis [0039] Previously described methods were used to compare the gene expression patterns of 1021 untreated cells (control) with those of RD64, 1021+IAA, 1021+Ind, 1021+Trp, 1021+ICA and 1021+2,4-D cells grown under P-sufficient (13 mM) conditions as reported in Imperlini et al. (21). RT-PCR Analysis [0040] Total RNA from Psufficient and P-starved cells was isolated as previously described (5). cDNA were synthesized with the StrataScript.(TM). reverse transcription reagents (Stratagene) and random hexamers as primers. Quantitative PCR was performed with the Power SYBR PCR Master Mix (Applied Biosystems). Reactions were run on the iCycler iQ (Bio-Rad). The thermo cycling condition were: 15 min at 95° C., 40 cycles of denaturation at 95° C. for 20 s, annealing (20 s) and extension (35 s) at 72° C. Specific primer pairs, designed using the Primer3 software, are shown.

Results

log2 of the ratio of intensities of each spots in the two channels (no units) = 0.940431647 at 0.5 mM

Location

Page/Page column 3; 4; 6

Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; US2012/40828; (2012); (A1) English, View in Reaxys 46 of 80

Effect (Pharmacological Data)

antibodies raised to Immunogens I and II; binding to

Species or Test-System (Pharmacological Data)

antibodies raised to Immunogens I and II

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Kind of Dosing (Pharma- title compound prepared in Tris buffered saline containing Tween 20 (TBST) solution cological Data) Method (Pharmacological Data)

Immunoassays using antibodies of the invention to test for potential cross-reactants (Table 3) and to screen the urine and serum of twenty patients for cross-reactive molecules, did not reveal any cross-reactants which could invalidate the measurements taken using the antibodies, methods, kits and products of the invention.

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

750000 ng/l

Results

cross-reactivity (percent) = <0.28

Location

Page/Page column 12

Patent; Randox Laboratories Ltd.; EP2487155; (2012); (A1) English, View in Reaxys 47 of 80

Effect (Pharmacological Data)

cytotoxic

Species or Test-System (Pharmacological Data)

cancer K-562 cells of human

Further Details (Pharma- MTT method cological Data) Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 100 μg/ml

Yan, Jian; Sun, Li-Rong; Zhou, Zhong-Yu; Chen, Yu-Chan; Zhang, Wei-Min; Dai, Hao-Fu; Tan, Jian-Wen; Phytochemistry; vol. 80; (2012); p. 37 - 41, View in Reaxys 48 of 80

Effect (Pharmacological Data)

cytotoxic

Species or Test-System (Pharmacological Data)

cancer NCI-H460 cells of human

Further Details (Pharma- MTT method cological Data) Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 100 μg/ml

Yan, Jian; Sun, Li-Rong; Zhou, Zhong-Yu; Chen, Yu-Chan; Zhang, Wei-Min; Dai, Hao-Fu; Tan, Jian-Wen; Phytochemistry; vol. 80; (2012); p. 37 - 41, View in Reaxys 49 of 80

Effect (Pharmacological Data)

cytotoxic

Species or Test-System (Pharmacological Data)

cancer SF-268 cells of human

Further Details (Pharma- MTT method cological Data) Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 100 μg/ml

Yan, Jian; Sun, Li-Rong; Zhou, Zhong-Yu; Chen, Yu-Chan; Zhang, Wei-Min; Dai, Hao-Fu; Tan, Jian-Wen; Phytochemistry; vol. 80; (2012); p. 37 - 41, View in Reaxys 50 of 80

Effect (Pharmacological Data)

cytotoxic

Species or Test-System (Pharmacological Data)

cancer SGC-7901 cells of human

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Further Details (Pharma- MTT method cological Data) Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 100 μg/ml

Yan, Jian; Sun, Li-Rong; Zhou, Zhong-Yu; Chen, Yu-Chan; Zhang, Wei-Min; Dai, Hao-Fu; Tan, Jian-Wen; Phytochemistry; vol. 80; (2012); p. 37 - 41, View in Reaxys 51 of 80

Effect (Pharmacological Data)

cytotoxic

Species or Test-System (Pharmacological Data)

cancer SMMC-7721 cells of human

Further Details (Pharma- MTT method cological Data) Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 100 μg/ml

Yan, Jian; Sun, Li-Rong; Zhou, Zhong-Yu; Chen, Yu-Chan; Zhang, Wei-Min; Dai, Hao-Fu; Tan, Jian-Wen; Phytochemistry; vol. 80; (2012); p. 37 - 41, View in Reaxys 52 of 80

Effect (Pharmacological Data)

growth; inhibition of

Species or Test-System (Pharmacological Data)

Botrytis cinerea UAMH 1784

Concentration (Pharmacological Data)

0.1 - 0.5 mmol/l

Kind of Dosing (Pharma- title comp. dissolved in DMSO cological Data) Further Details (Pharma- mycelial radial growth assay cological Data) Type (Pharmacological Data)

inhibition rate

Value of Type (Pharmacological Data)

6 - 31 percent

Pedras, M. Soledade C.; Hossain, Sajjad; Snitynsky, Ryan B.; Phytochemistry; vol. 72; nb. 2-3; (2011); p. 199 206, View in Reaxys 53 of 80

Effect (Pharmacological Data)

growth; inhibition of

Species or Test-System (Pharmacological Data)

Botrytis cinerea UAMH 1809

Concentration (Pharmacological Data)

0.1 - 0.5 mmol/l

Kind of Dosing (Pharma- title comp. dissolved in DMSO cological Data) Further Details (Pharma- mycelial radial growth assay cological Data) Type (Pharmacological Data)

inhibition rate

Value of Type (Pharmacological Data)

7 - 27 percent

Pedras, M. Soledade C.; Hossain, Sajjad; Snitynsky, Ryan B.; Phytochemistry; vol. 72; nb. 2-3; (2011); p. 199 206, View in Reaxys

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54 of 80

Effect (Pharmacological Data)

growth; inhibition of

Species or Test-System (Pharmacological Data)

Alternaria brassicicola

Concentration (Pharmacological Data)

0.1 - 0.5 mmol/l

Further Details (Pharma- mycelial radial growth assay cological Data) Type (Pharmacological Data)

inhibition rate

Value of Type (Pharmacological Data)

6 - 22 percent

Pedras, M. Soledade C.; Hossain, Sajjad; Phytochemistry; vol. 72; nb. 18; (2011); p. 2308 - 2316, View in Reaxys 55 of 80

Effect (Pharmacological Data)

growth; inhibition of

Species or Test-System (Pharmacological Data)

Rhizoctonia solani

Concentration (Pharmacological Data)

0.2 - 0.5 mmol/l

Further Details (Pharma- mycelial radial growth assay cological Data) Type (Pharmacological Data)

inhibition rate

Value of Type (Pharmacological Data)

5 - 9 percent

Pedras, M. Soledade C.; Hossain, Sajjad; Phytochemistry; vol. 72; nb. 18; (2011); p. 2308 - 2316, View in Reaxys 56 of 80

Effect (Pharmacological Data)

growth; inhibition of

Species or Test-System (Pharmacological Data)

Sclerotinia sclerotiorum

Concentration (Pharmacological Data)

0.1 - 0.5 mmol/l

Further Details (Pharma- mycelial radial growth assay cological Data) Type (Pharmacological Data)

inhibition rate

Value of Type (Pharmacological Data)

4 - 34 percent

Pedras, M. Soledade C.; Hossain, Sajjad; Phytochemistry; vol. 72; nb. 18; (2011); p. 2308 - 2316, View in Reaxys 57 of 80

Comment (Pharmacological Data)

physiological behaviour discussed

Wua, Yixuan; Zhang, Zhen-Xue; Hu, Hui; Li, Dongmei; Qiu, Guofu; Hua, Xianming; He, Xiangjiu; Fitoterapia; vol. 82; nb. 2; (2011); p. 288 - 292, View in Reaxys 58 of 80

Effect (Pharmacological Data)

DNA; examination of

Species or Test-System (Pharmacological Data)

leukemic U937 cells of human

Concentration (Pharmacological Data)

0.5 - 5 mmol/l

Method (Pharmacological Data)

cells treated with various conc. of title comp. for 24 h; DNA extracted and separated by agarose gel electrophoresis; gel stained with ethidium bromide and imaged with FluorImager

Results

title comp. induced DNA fragmentation only at 5 mM; fig.

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Inagaki, Shyuichiro; Morimura, Shigeru; Gondo, Kazunobu; Tang, Yueqin; Akutagawa, Hiroshi; Kida, Kenji; Bioscience, Biotechnology and Biochemistry; vol. 71; nb. 2; (2007); p. 371 - 379, View in Reaxys 59 of 80

Effect (Pharmacological Data)

D-amino acid oxidase (DAO) activity; inhibition of

Species or Test-System (Pharmacological Data)

kidney D-amino acid oxidase (DAO) of porcine

Method (Pharmacological Data)

D-AMINO ACID OXIDASE RELATED ASSAYSInhibition of porcine kidney DAOPorcine kidney D-amino acid oxidase (catalog No. A-5222 from Sigma) and D-serine (catalog No. S-4250 from Sigma) was be used to test the DAO inhibitory activity of test compounds. The breakdown of D-serine by DAO produces hydrogen peroxidase, which can be measured using, for example, the Amplex.(R). Red Hydrogen Peroxide Assay Kit (Catalog No. A-22188, Molecular Probes, Inc.; Eugene, OR). A working solution was prepared by mixing: sodium phosphate buffer (8.7 ml, 0.025M, pH 7.4), D-serine solution (1.0 ml, 100 mM in water), horseradish peroxidase (0.2 ml, 10 U/ml in buffer), and Amplex Red solution (0.1 ml, 1 mg dye in 200 ul in DMSO (50 μM in DMSO)). A working enzyme solution is prepared by diluting a D-amino acid oxidase stock solution (65 U/ml) one hundred fold. The working solution (100 μl) was transferred to wells of a Microfluor microtiter plate and a solution of the inhibitor in DMSO is added. The EPO working solution (100 μl) was transferred to wells of a Microfluor B microtiter plate (2 μl Ix reaction buffer or H2O2) and a solution (1 μl) of the inhibitor in DMSO is added. The working enzyme (5 μl) was added to each well and the rate of reaction (hydrogen peroxide released) was determined by measuring the oxidation of Amplex Red by spectrophotometry, using a plate reader (excitation wavelength 544 nm, emission wavelength, 590 nM) after a reaction time of 5 minutes. Controls were carried out using DMSO in the absence of inhibitor. A known DAO inhibitor, indole-2-carboxylic acid, was used as a control in this assay. Figure 6 presents the results of the analysis of certain compounds in the DAO assay.

Results

percent inhibition at 10 μM = <1

Location

Page/Page column 88; 188-189; 68/75

Patent; MICROBIA, INC.; WO2007/22501; (2007); (A2) English, View in Reaxys 60 of 80

Effect (Pharmacological Data)

cytotoxicity

Species or Test-System (Pharmacological Data)

human central nervous system carcinoma SF-268 cells

Method (Pharmacological Data)

MTT assay

Comment (Pharmacological Data)

No effect

Wu, Pei-Lin; Hsu, Yu-Lin; Jao, Chen-Wei; Journal of Natural Products; vol. 69; nb. 10; (2006); p. 1467 - 1470, View in Reaxys 61 of 80

Effect (Pharmacological Data)

cytotoxicity

Species or Test-System (Pharmacological Data)

human lung carcinoma NCI-H460 cells

Method (Pharmacological Data)

MTT assay

Comment (Pharmacological Data)

No effect

Wu, Pei-Lin; Hsu, Yu-Lin; Jao, Chen-Wei; Journal of Natural Products; vol. 69; nb. 10; (2006); p. 1467 - 1470, View in Reaxys 62 of 80

Effect (Pharmacological Data)

cytotoxicity

Species or Test-System (Pharmacological Data)

human breast carcinoma MCF-7 cells

Method (Pharmacological Data)

MTT assay

Comment (Pharmacological Data)

No effect

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Wu, Pei-Lin; Hsu, Yu-Lin; Jao, Chen-Wei; Journal of Natural Products; vol. 69; nb. 10; (2006); p. 1467 - 1470, View in Reaxys 63 of 80

Effect (Pharmacological Data)

growth; promoting of

Species or Test-System (Pharmacological Data)

wheat

Method (Pharmacological Data)

Effect of IAA Production by Acinetobacter spp. on Growth of Wheat Plant: The effect of IAA production on growth of wheat plant was tested by pot experiments. All eight Acinetobacter strains were grown separately in following four media i) LB, ii) LBT: containing 1 mg/ml of tryptophan iii) AMM, iv) AMMT: containing 1 mg/ml of tryptophan. LB and AMM were used as a control media and LBT and AMMT were used for IAA production. Eight Acinetobacter genospecies were inoculated in all 4 media and incubated at 120 rpm at 28° C. up to 48 h.

The wheat seeds were surface sterilized by 2percent HgCl2 (Subba Rao, 1988) and washed with sterile distilled water for 6 to 7 time to remove HgCl2 completely. After washing, seeds were added in above-mentioned culture and kept on shaker at 120 rpm for 2 h at 28° C. After 2 h, wheat seeds were aseptically collected and inoculated in pots containing sterile soil.

Wheat seeds mixed with uninoculated media as well as with distilled water were treated as control. The pots were kept in sunlight and raised under close supervision. The growth of plants was observed everyday for 21 days. After 21 days plants were carefully uprooted and root and shoot lengths were measured. Same experiment was done simultaneously using large size pots up to 4 months for complete life cycle of wheat plant.

Results

color of leaves was dark-green compared with pale-green in control; width of shoots was double compared with control; inflorescence and fruiting stages were observed 10 days earlier than in control; results are given in FIG.5

Location

Page/Page column 6-7

Comment (Pharmacological Data)

potential area of application: agro

Patent; Council of Scientific and Industrial Research; US2005/70435; (2005); (A1) English, View in Reaxys 64 of 80

Effect (Pharmacological Data)

cytotoxicity

Species or Test-System (Pharmacological Data)

H9 cells

Further Details (Pharma- AZT used as reference comp. (IC50: 500 μg/ml); IC50: conc. that inhibits uninfected cell cological Data) growth by 50 percent Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

16.40 mg/l

Wu, Pei-Lin; Lin, Fu-Wen; Wu, Tian-Shung; Kuoh, Chang-Sheng; Lee, Kuo-Hsiung; Lee, Shiow-Ju; Chemical and Pharmaceutical Bulletin; vol. 52; nb. 3; (2004); p. 345 - 349, View in Reaxys 65 of 80

Effect (Pharmacological Data)

antiviral, anti HIV

Species or Test-System (Pharmacological Data)

H9 cells

Method (Pharmacological Data)

effect on HIV replication in cells assessed

Further Details (Pharma- AZT used as reference comp. (EC50: 0.0007 μg/ml); EC50: conc. that inhibits viral replicacological Data) tion by 50 percent Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

2.41 mg/l

Wu, Pei-Lin; Lin, Fu-Wen; Wu, Tian-Shung; Kuoh, Chang-Sheng; Lee, Kuo-Hsiung; Lee, Shiow-Ju; Chemical and Pharmaceutical Bulletin; vol. 52; nb. 3; (2004); p. 345 - 349, View in Reaxys 66 of 80

Effect (Pharmacological Data)

cytotoxicity

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Species or Test-System (Pharmacological Data)

NUGC-3 human gastric carcinoma cells

Concentration (Pharmacological Data)

20 mg/l

Comment (Pharmacological Data)

No effect

Wu, Pei-Lin; Lin, Fu-Wen; Wu, Tian-Shung; Kuoh, Chang-Sheng; Lee, Kuo-Hsiung; Lee, Shiow-Ju; Chemical and Pharmaceutical Bulletin; vol. 52; nb. 3; (2004); p. 345 - 349, View in Reaxys 67 of 80

Effect (Pharmacological Data)

cytotoxicity

Species or Test-System (Pharmacological Data)

HONE-1 human nasopharyngeal carcinoma cells

Concentration (Pharmacological Data)

20 mg/l

Comment (Pharmacological Data)

No effect

Wu, Pei-Lin; Lin, Fu-Wen; Wu, Tian-Shung; Kuoh, Chang-Sheng; Lee, Kuo-Hsiung; Lee, Shiow-Ju; Chemical and Pharmaceutical Bulletin; vol. 52; nb. 3; (2004); p. 345 - 349, View in Reaxys 68 of 80

Effect (Pharmacological Data)

cytotoxicity

Species or Test-System (Pharmacological Data)

A549 human lung carcinoma cells

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

4.6 mg/l

Wu, Pei-Lin; Lin, Fu-Wen; Wu, Tian-Shung; Kuoh, Chang-Sheng; Lee, Kuo-Hsiung; Lee, Shiow-Ju; Chemical and Pharmaceutical Bulletin; vol. 52; nb. 3; (2004); p. 345 - 349, View in Reaxys 69 of 80

Effect (Pharmacological Data)

cytotoxicity

Species or Test-System (Pharmacological Data)

MCF-7 human breast carcinoma cells

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

12.9 mg/l

Wu, Pei-Lin; Lin, Fu-Wen; Wu, Tian-Shung; Kuoh, Chang-Sheng; Lee, Kuo-Hsiung; Lee, Shiow-Ju; Chemical and Pharmaceutical Bulletin; vol. 52; nb. 3; (2004); p. 345 - 349, View in Reaxys 70 of 80

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

human intestinal epithelial Caco-2 cells

Concentration (Pharmacological Data)

2 mmol/l

Method (Pharmacological Data)

in vitro; cells grown on Transwell polycarbonate filters for 20-22 days; filter preincubated for 10-15 min at 37 deg C; solution of title comp. added to AP side; BL solution sampled at 40min intervals; title comp. measured by fluorescence after HPLC

Further Details (Pharma- AP-to-BL absorption experiment; AP, apical; BL, basolateral; degradation of title comp. becological Data) fore and during permeation investigated Comment (Pharmacological Data)

No effect

Ano, Rieko; Kimura, Yukitaka; Urakami, Machiko; Shima, Motohiro; Matsuno, Ryuichi; Ueno, Tamio; Akamatsu, Miki; Bioorganic and Medicinal Chemistry; vol. 12; nb. 1; (2004); p. 249 - 255, View in Reaxys

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71 of 80

Effect (Pharmacological Data)

transport

Species or Test-System (Pharmacological Data)

human intestinal epithelial Caco-2 cells

Concentration (Pharmacological Data)

2 mmol/l

Method (Pharmacological Data)

in vitro; BL-to-AP absorption experiment; cells grown on Transwell polycarbonate filters for 20-22 days; title comp. dissolved in BL solution; AP solution sampled at 40-min intervals; title comp. measured by fluorescence after HPLC

Further Details (Pharma- cells from American Type Culture Collection; measurement repeated at least four times; AP, cological Data) apical; BL, basolateral Results

apparent permeability coefficient, Papp (x10-6, cm/s), for title comp. across Caco-2 cells in BL-to-AP direction: 14.5

Ano, Rieko; Kimura, Yukitaka; Urakami, Machiko; Shima, Motohiro; Matsuno, Ryuichi; Ueno, Tamio; Akamatsu, Miki; Bioorganic and Medicinal Chemistry; vol. 12; nb. 1; (2004); p. 249 - 255, View in Reaxys 72 of 80

Effect (Pharmacological Data)

transport

Species or Test-System (Pharmacological Data)

human intestinal epithelial Caco-2 cells

Concentration (Pharmacological Data)

2 mmol/l

Method (Pharmacological Data)

in vitro; cells grown on Transwell polycarbonate filters for 20-22 days; filter preincubated for 10-15 min at 37 deg C; solution of title comp. added to AP side; BL solution sampled at 40min intervals; title comp. measured by fluorescence after HPLC

Further Details (Pharma- AP-to-BL absorption experiment; cells from American Type Culture Collection; measurecological Data) ment repeated at least four times; AP, apical; BL, basolateral Results

apparent permeability coefficient, Papp (x10-6, cm/s), for title comp. across Caco-2 cells in AP-to-BL direction: 27.5; active transport mechanism

Ano, Rieko; Kimura, Yukitaka; Urakami, Machiko; Shima, Motohiro; Matsuno, Ryuichi; Ueno, Tamio; Akamatsu, Miki; Bioorganic and Medicinal Chemistry; vol. 12; nb. 1; (2004); p. 249 - 255, View in Reaxys 73 of 80

Effect (Pharmacological Data)

enzyme; induction of

Species or Test-System (Pharmacological Data)

Arthrobacter nicotianae FI1612

Method (Pharmacological Data)

resting-cells of Arthrobacter nicotianae FI1612 was incubated in potassium phosphate buffer (pH 7.0) and dithiothreitol with title comp. and indole-3-carboxylate at 30 deg C for 10 min; centrifugation; HPLC

Results

total activity of indole-3-carboxylate decarboxylase 23.8 nmol/ml min

Yoshida, Toyokazu; Fujita, Kohei; Nagasawa, Toru; Bioscience, Biotechnology and Biochemistry; vol. 66; nb. 11; (2002); p. 2388 - 2394, View in Reaxys 74 of 80

Effect (Pharmacological Data)

enzyme; induction of

Species or Test-System (Pharmacological Data)

phenylalanine ammonia-lyase

Kim, Seong Hwan; Kronstad, James W.; Ellis, Brian E.; Phytochemistry; vol. 58; nb. 6; (2001); p. 849 - 857, View in Reaxys 75 of 80

Effect (Pharmacological Data)

protein; activation of

Species or Test-System (Pharmacological Data)

Wistar rat cell membranes

Sex

male

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Method (Pharmacological Data)

epididymal adipocyte or spleen membrane preparations incubated with various conc. of title comp. and 0.2 nmol/l <35S>GTPγS for 90 min at 25 deg C; filtered; bound radioactivity counted

Further Details (Pharma- GTPγS: guanosine 5'-(γ-thio)triphosphate (GTPγS binding reflects G protein activation) cological Data) Comment (Pharmacological Data)

No effect

Lorenzen, Anna; Stannek, Christina; Lang, Heidrun; Andrianov, Viktor; Kalvinsh, Ivars; Schwabe, Ulrich; Molecular Pharmacology; vol. 59; nb. 2; (2001); p. 349 - 357, View in Reaxys 76 of 80

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

Phoma lingam avirulent isolate Unity

Concentration (Pharmacological Data)

0.0002 mol/l

Method (Pharmacological Data)

in vitro; inoculated with fungal spores (2E9 per flask); minimal medium; incubation 5 days; metabolites isolated by preparative TLC

Comment (Pharmacological Data)

No effect

Pedras, M. Soledade C.; Okanga, Francis I.; Canadian Journal of Chemistry; vol. 78; nb. 3; (2000); p. 338 - 346, View in Reaxys 77 of 80

Effect (Pharmacological Data)

fungistatic

Species or Test-System (Pharmacological Data)

Phoma lingam avirulent isolate Unity

Concentration (Pharmacological Data)

0.0001 - 0.0005 mol/l

Method (Pharmacological Data)

in vitro; mycelial radial growth bioassay; incubation time 72 h

Results

percent inhibition/dose (M): 1/1E-4, and 1/5E-4

Pedras, M. Soledade C.; Okanga, Francis I.; Canadian Journal of Chemistry; vol. 78; nb. 3; (2000); p. 338 - 346, View in Reaxys 78 of 80

Comment (Pharmacological Data)

effect on cell growth of callus cultures of Oenothera laciniata

Taniguchi, Shoko; Nakamura, Nobuhiko; Nose, Midori; Takeda, Shiho; Yabu-Uchi, Ryoko; Ito, Hideyuki; Yoshida, Takashi; Yazaki, Kazufumi; Phytochemistry; vol. 48; nb. 6; (1998); p. 981 - 985, View in Reaxys 79 of 80

Comment (Pharmacological Data)

antifouling activity

Kon-Ya, Kazumi; Shimidzu, Nobuyoshi; Miki, Wataru; Endo, Mamoru; Bioscience, Biotechnology, and Biochemistry; vol. 58; nb. 12; (1994); p. 2178 - 2181, View in Reaxys 80 of 80

Comment (Pharmacological Data)

inhibitor of β-(9-cytokinin)alanine synthase; Ki 1100 μM

Parker, Charles W.; Entsch, Barrie; Letham, David S.; Phytochemistry (Elsevier); vol. 25; nb. 2; (1986); p. 303 310, View in Reaxys Ecotoxicology (2) 1 of 2

Effect (Ecotoxicology)

fungal growth; effect on

Species or Test-System (Ecotoxicology)

Leptosphaeria maculans (Desm.) Ces. et de Not. L2/M2

Concentration (Ecotoxicology)

0.1 - 0.5 mmol/l

Method (Ecotoxicology)

single-spore isolates Laird 2 and Mayfair 2; mycelial radial growth bioassay; test fungi incubated with title comp. for 5 d

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Comment (Ecotoxicology)

No effect

Pedras, M. Soledade C.; Gadagi, Ravi S.; Jha, Mukund; Sarma-Mamillapalle, Vijay K.; Phytochemistry; vol. 68; nb. 11; (2007); p. 1572 - 1578, View in Reaxys 2 of 2

Effect (Ecotoxicology)

microorganisms

Species or Test-System (Ecotoxicology)

Pseudomonas sp. LD2

Method (Ecotoxicology)

isolate LD2; carbazole-degrading bacerium isolated by enrichment from creosote-contaminated soil from a site in Edmonton, AB, Canada; nitrogen-free mineral medium; 28 deg C; in the dark

Further Details (Ecotoxi- turbidity (OD600) cology) Results

good growth

Gieg, Lisa M.; Otter, Albin; Fedorak, Phillip M.; Environmental Science and Technology; vol. 30; nb. 2; (1996); p.

575 - 585, View in Reaxys Use (26) Use Pattern

References

increases serum Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys insulin-like growth factor 1 (IGF-1) level Disease states as- Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys sociated with reduced insulin-like growth factor 1 (IGF-1) serum level Serious fatigue

Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys

Exhausting symp- Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys toms Burn-out syndrome

Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys

Chronic fatigue syndrome (CFS)

Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys

Depression

Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys

Alzheimer disease

Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys

Irritated bowel syndrome

Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys

Osteoporosis

Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys

Type 2 diabetes

Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys

Anti-aging

Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys

Immune therapy

Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys

Recovery after ex- Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys ercise Myalgia

Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys

Muscle aches

Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys

Sore throat

Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys

Severe tiredness

Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys

Swollen lymph no- Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys des in the neck

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Swollen lymph no- Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys des in the armpits Pain without redness

Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys

Swelling in a num- Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys ber of joints Intense patterns of headaches

Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys

Changing patterns of headaches

Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys

unrefreshing sleep

Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys

weariness

Patent; Gillessen, Hubert Jean-Marie Francois; US2008/194553; (2008); (A1) English, View in Reaxys

Isolation from Natural Product (56) Isolation from Nat- Location ural Product

Comment (Isolation from Natural Product)

References

gorgonian Paraplexaura sp; collected in Zhanjiang, Naozhou Island, South China Sea, China, July 2011

Liu, Fen; Li, Shuo; Ju, Zhi-Ran; Liu, Ting-Ting; Liang, Rui-Yu; Liao, Xiao-Jian; Xu, Shi-Hai; Journal of Asian Natural Products Research; vol. 17; nb. 8; (2015); p. 851 - 855, View in Reaxys

stems and roots of Clerodendrum philippinum var. simplex; collected at Xishuangbanna tropical botanical garden, Chinese academy of sciences, Yunnan Province, July, 2011

Yue, Jia-Rui; Feng, De-Qiang; Xu, You-Kai; Natural Product Research; vol. 29; nb. 13; (2015); p. 1228 - 1234, View in Reaxys

Scapharca subcrenata; collected in South China Sea

Yan, Xu; Xue-Ping, Sun; Xiu-Guo, Zhang; Wan-Ping, Tong; Chemistry of Natural Compounds; vol. 51; nb. 4; (2015); p. 800 - 802; Khim.

Prir. Soedin.; nb. 4; (2015); p. 683 - 684,2, View in Reaxys

whole bodies of Polyrhachis dives, Chinese black ant; collected in Wenshan, Yunnan Province, China, September 2012

Tang, Jian-Jun; Xia, Hou-Lin; Cheng, Yong-Xian; Luo, Qi; Di, Lei; Lu, Qing; Hou, Bo; Zuo, Zhi-Li; Zhang, Li; Ma, Xiu-Jing; Journal of Asian Natural Products Research; vol. 17; nb. 1; (2015); p. 20 - 26, View in Reaxys

air-dried aerial parts of Bidens frondosa; collected from Jiujiang, Jiangxi Province during July 2013

Le, Jiamei; Lu, Wenquan; Xiong, Xiaojuan; Wu, Zhijun; Chen, Wansheng; Molecules; vol. 20; nb. 10; (2015); p. 18496 - 18510, View in Reaxys

marine-derived fungus Pseudallescheria ellipsoidea F42−3 from the soft coral Lobophytum crassum; collected in Hainan Sanya National Coral Reef Reserve, China.

Liu, Wei; Li, Hou-Jin; Xu, Meng-Yang; Ju, Ying-Chen; Wang, LaiYou; Xu, Jun; Yang, De-Po; Lan, Wen-Jian; Organic Letters; vol. 17; nb. 21; (2015); p. 5156 - 5159, View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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aerial parts of Pouzolzia zeylanica (L.) Benn. var. microphylla (Wedd.)W.T.Wan g; collected in Guangzhou, Guangdong province, China, July 2011

Chen, Zhuo-Han; Zhang, Hui; Tao, Shu-Hong; Luo, Zhao; Zhong, Chu-Qian; Guo, Li-Bing; Journal of Asian Natural Products Research; vol. 17; nb. 10; (2015); p. 959 - 966, View in Reaxys

sponge Halichondria sp.; collected in Meishan Island, Hainan Province, China, July 2008

Sun, Jian Fan; Wu, Yi; Yang, Bin; Liu, Yonghong; Chemistry of Natural Compounds; vol. 51; nb. 5; (2015); p. 975 - 977; Khim. Prir. Soedin.; nb. 5; (2015); p. 836 - 837,2, View in Reaxys

leaves of Perilla supporting inforfrutescens Britton mation var. acuta Kudo; collected from Namwon in Jeollanam-do, Korea

Woo, Kyeong Wan; Han, Ji Young; Suh, Won Se; Lee, Jei Hyun; Lee, Kang Ro; Bulletin of the Korean Chemical Society; vol. 35; nb. 7; (2014); p. 2151 - 2154, View in Reaxys

whole bodies of supporting inforAspongopus chi- mation nensis; purchased from Hunan Corporation of Chinese Materia Medica (Changsha) of China

Shi, Yan-Ni; Tu, Zheng-Chao; Wang, Xin-Long; Yan, Yong-Ming; Fang, Ping; Zuo, Zhi-Li; Hou, Bo; Yang, Tong-Hua; Cheng, YongXian; Bioorganic and Medicinal Chemistry Letters; vol. 24; nb. 22; (2014); p. 5164 - 5169, View in Reaxys

Annulohypoxylon ilanense BCRC 34015; isolated from the wood of medicinal plant Cinnamomum sp. collected from Tatung, Chi-lanshan, I-lan County, Taiwan

Wu, Ming-Der; Cheng, Ming-Jen; Chen, Ih-Sheng; Su, Yung-Shun; Hsieh, Sung-Yuan; Chang, Hsun-Shuo; Chang, Chun-Wei; Yuan, Gwo-Fang; Chemistry and Biodiversity; vol. 10; nb. 3; (2013); p. 493 - 505, View in Reaxys

flowers of Albizia julibrissin Durazz; collected from Hubei, China

Yahagi, Tadahiro; Daikonya, Akihiro; Kitanaka, Susumu; Chemical and Pharmaceutical Bulletin; vol. 60; nb. 1; (2012); p. 129 - 136, View in Reaxys

aerial parts of Portulaca oleracea; collected in the suburb area of Guangzhou, Guangdong Province, P.R. China

Yan, Jian; Sun, Li-Rong; Zhou, Zhong-Yu; Chen, Yu-Chan; Zhang, Wei-Min; Dai, Hao-Fu; Tan, Jian-Wen; Phytochemistry; vol. 80; (2012); p. 37 - 41, View in Reaxys

whole plant of Saussurea deltoidea; collected from the city of Kunming, Yunnan province, People's Republic of China

Xu, Jun-Ju; Huang, Huo-Qiang; Zeng, Guang-Zhi; Tan, Ning-Hua; Fitoterapia; vol. 83; nb. 6; (2012); p. 1125 - 1130, View in Reaxys

fungal strain Wallemia sebi PXP-89; working strain isolated from the surface of the leaves of the mangrove plant, Excoecaria agal-

Peng, Xiao-Ping; Wang, Yi; Liu, Pei-Pei; Hong, Kui; Chen, Hao; Yin, Xia; Zhu, Wei-Ming; Archives of Pharmacal Research; vol. 34; nb. 6; (2011); p. 907 - 912, View in Reaxys

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locha (Euphorbiaceae) collected in Wenchang, Hainan province of China Radix isatidis (Ban-Lan-Gen in Chinese), roots of Isatis indigotica; purchased from Wuhan Longtai (Wuhan, China)

Wua, Yixuan; Zhang, Zhen-Xue; Hu, Hui; Li, Dongmei; Qiu, Guofu; Hua, Xianming; He, Xiangjiu; Fitoterapia; vol. 82; nb. 2; (2011); p.

288 - 292, View in Reaxys

mycelium of Botryosphaeria rhodina; collected in Cairo, Egypt

Abdou, Randa; Scherlach, Kirstin; Dahse, Hans-Martin; Sattler, Isabel; Hertweck, Christian; Phytochemistry; vol. 71; nb. 1; (2010); p. 110 - 116, View in Reaxys

Streptomyces sp.

HK10552 isolated from leaves of Aegiceras corniculatum; plant collected near Xiamen City, Fujian Province, China

Wang, Fangfang; Xu, Minjuan; Li, Qingshan; Sattler, Isable; Lin, Wenhan; Molecules; vol. 15; nb. 4; (2010); p. 2782 - 2790, View in Reaxys

stem bark of Trewia nudiflora L.; collected in Rajshahi, Bangladesh

Shilpi, Jamil A.; Gray, Alexander I.; Seidel, Veronique; Fitoterapia; vol. 81; nb. 6; (2010); p. 536 - 539, View in Reaxys

aerial parts of Saussurea deltoidea (DC.) C. B. Clarke; collected in Dafang, Guizhou province, China

Xiao, Hai-Tao; Liu, Bin; Hao, Xiao-Yan; Yang, Xiao-Sheng; Sun, Qian-Yun; Chemistry of Natural Compounds; vol. 45; nb. 4; (2009); p.

539 - 541, View in Reaxys

whole plant of Houttuynia cordata Thunb. (Saururaceae) collected in Taiwan in July 2004

Chou, Shu-Chen; Su, Chung-Ren; Ku, Yuh-Chi; Wu, Tian-Shung; Chemical and Pharmaceutical Bulletin; vol. 57; nb. 11; (2009); p. 1227 - 1230, View in Reaxys

Streptomyces sp. isolate Mei37; collected in Jade Bay, North Sea, Germany

Hawas, Usama W.; Shaaban, Mohamed; Shaaban, Khaled A.; Speitling, Michael; Maier, Armin; Kelter, Gerhard; Fiebig, Heinz H.; Meiners, Marinus; Helmke, Elisabeth; Laatsch, Hartmut; Journal of Natural Products; vol. 72; nb. 12; (2009); p. 2120 - 2124, View in Reaxys

whole plant of Arabidopsis thaliana ecotype Columbia-0; collected at Miura Peninsula, Kanagawa, Japan, 2005, December

Nakabayashi, Ryo; Kusano, Miyako; Kobayashi, Makoto; Tohge, Takayuki; Yonekura-Sakakibara, Keiko; Kogure, Noriyuki; Yamazaki, Mami; Kitajima, Mariko; Saito, Kazuki; Takayama, Hiromitsu; Phytochemistry; vol. 70; nb. 8; (2009); p. 1017 - 1029, View in Reaxys

Xanthium strumarium L. (Asteraceae), seeds

Lee, Chia-Lin; Huang, Po-Ching; Hsieh, Pei-Wen; Hwang, TsongLong; Hou, Yu-Yi; Chang, Fang-Rong; Wu, Yang-Chang; Planta Medica; vol. 74; nb. 10; (2008); p. 1276 - 1279, View in Reaxys

culture broth of Penicillium herquei isolate GA3

Ding, Ling; Fotso, Serge; Li, Fuchao; Qin, Song; Laatsch, Hartmut; Journal of Natural Products; vol. 71; nb. 6; (2008); p. 1068 - 1069, View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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leaves of Cucumis sativus L. (Cucurbitaceae) (Takaoka, Miyazaki, Japan, September and October 2004)

Kai, Hisahiro; Baba, Masaki; Okuyama, Toru; Chemical and Pharmaceutical Bulletin; vol. 55; nb. 1; (2007); p. 133 - 136, View in Reaxys

Tarenna attenuata (Rubiaceae), whole plant (Xishuangbanna, Yunnan Province, People's Republic of China)

Yang, Xian-Wen; Wang, Jun-Song; Wang, Yue-Hu; Xiao, Hai-Tao; Hu, Xu-Jia; Mu, Shu-Zhen; Yan-Lin, Ma.; Lin, Hua; He, Hong-Ping; Li, Ng; Hao, Xiao-Jiang; Planta Medica; vol. 73; nb. 5; (2007); p. 496 - 498, View in Reaxys

herbs of Aster indicus L. collected in municipal botanical garden in Taipei, Taiwan

Lin, Chwan-Fwu; Shen, Chien-Chang; Chen, Chien-Chih; Sheu, Shuenn-Jyi; Huang, Yu-Ling; Phytochemistry; vol. 68; nb. 19; (2007); p. 2450 - 2454, View in Reaxys

culture broth of Streptomyces sp.

B8000, derived from the sediment of the Laguna de Terminos at the Gulf of Mexico

Poumale, Herve M. P.; Ngadjui, Bonaventure T.; Helmke, Elisabeth; Laatsch, Hartmut; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 61; nb. 11; (2006); p. 1450 - 1454, View in Reaxys

marine sponge Haliclona oculata (Demospongiae) collected off the inner coral reef at a depth of 15 m, near the coastline of southern Sanya, Hainan Island, People's Republic of China

Yu, Shanjiang; Deng, Zhiwei; Proksch, Peter; Lin, Wenhan; Journal of Natural Products; vol. 69; nb. 9; (2006); p. 1330 - 1334, View in Reaxys

dried plants of Cephalanceropsis gracilis (Orchidaceae) collected from Pingtung Hsien, Taiwan

Wu, Pei-Lin; Hsu, Yu-Lin; Jao, Chen-Wei; Journal of Natural Products; vol. 69; nb. 10; (2006); p. 1467 - 1470, View in Reaxys

Acinetobacter haemolyticus A19 (NCIM 5155)

extraction by ethyl Patent; Council of Scientific and Industrial Research; acetate; evapora- US2005/70435; (2005); (A1) English, View in Reaxys tion of solvent; preparative TLC

Acinetobacter genospecies 3 A28 (NCIM 5159)

extraction by ethyl Patent; Council of Scientific and Industrial Research; acetate; evapora- US2005/70435; (2005); (A1) English, View in Reaxys tion of solvent; preparative TLC

Acinetobacter genospecies 3 A15 (NCIM 5151)

extraction by ethyl Patent; Council of Scientific and Industrial Research; acetate; evapora- US2005/70435; (2005); (A1) English, View in Reaxys tion of solvent; preparative TLC

Acinetobacter baumannii A13 (NCIM 5158)

extraction by ethyl Patent; Council of Scientific and Industrial Research; acetate; evapora- US2005/70435; (2005); (A1) English, View in Reaxys tion of solvent; preparative TLC

Acinetobacter baumannii A16 (NCIM 5156)

extraction by ethyl Patent; Council of Scientific and Industrial Research; acetate; evapora- US2005/70435; (2005); (A1) English, View in Reaxys tion of solvent; preparative TLC

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Acinetobacter baumannii A18 (NCIM 5157)

extraction by ethyl Patent; Council of Scientific and Industrial Research; acetate; evapora- US2005/70435; (2005); (A1) English, View in Reaxys tion of solvent; preparative TLC

Acinetobacter baumannii A30 (NCIM 5154)

extraction by ethyl Patent; Council of Scientific and Industrial Research; acetate; evapora- US2005/70435; (2005); (A1) English, View in Reaxys tion of solvent; preparative TLC

Acinetobacter junii A6 (NCIM 5153)

extraction by ethyl Patent; Council of Scientific and Industrial Research; acetate; evapora- US2005/70435; (2005); (A1) English, View in Reaxys tion of solvent; preparative TLC

the air-dried rhizomes of Begonia nantoensis Lai and Chung (Begoniaceae) collected from Nanto Hsien, Taiwan, Republic of China, in February 2002

Wu, Pei-Lin; Lin, Fu-Wen; Wu, Tian-Shung; Kuoh, Chang-Sheng; Lee, Kuo-Hsiung; Lee, Shiow-Ju; Chemical and Pharmaceutical Bulletin; vol. 52; nb. 3; (2004); p. 345 - 349, View in Reaxys

fresh aerial parts of Taraxacum formosanum

Leu, Yann-Lii; Shi, Li-Shian; Damu, Amooru Gangaiah; Chemical and Pharmaceutical Bulletin; vol. 51; nb. 5; (2003); p. 599 - 601, View in Reaxys

culture of Vibrio parahaemolyticus isolate Bio249, North Sea bacterium

Veluri, Ravikanth; Oka, Imelda; Wagner-Doebler, Irene; Laatsch, Hartmut; Journal of Natural Products; vol. 66; nb. 11; (2003); p. 1520 - 1523, View in Reaxys

liquid culture of Coniothyrium minitans LRS2130, mycoparasitic fungus

Machida, Koichi; Trifonov, Latchezar S.; Ayer, William A.; Lu, Zheng-Xiang; Laroche, Andre; Huang, Hung Chang; Cheng, Kuo Joan; Zantige, Jennifer L.; Phytochemistry; vol. 58; nb. 1; (2001); p.

173 - 177, View in Reaxys

leaves of Bauhinia tarapotensis Benth. (Leguminosae)

Braca; De Tommasi; Di Bari; Pizza; Politi; Morelli; Journal of Natural Products; vol. 64; nb. 7; (2001); p. 892 - 895, View in Reaxys

leaves of Aristolochia heterophylla Hemsl. (Aristolochiaceae)

Chan, Yu-Yi; Leu, Yann-Lii; Wu, Tian-Shung; Chemical and Pharmaceutical Bulletin; vol. 47; nb. 6; (1999); p. 887 - 889, View in Reaxys

Paenibacillus polymyxa with or without tryptophan addition

Lebuhn, Michael; Heulin, Thierry; Hartmann, Anton; FEMS Microbiology Ecology; vol. 22; nb. 4; (1997); p. 325 - 334, View in Reaxys

a Senegalese Delesseriacean seaweed, (collected at low tide near Almadies, north of Dakar), likely a species of Haraldiophyllum (Rhodophyta, Ceramiales, Delesseriaceae).

Guella; Mancini; N'Diaye; Pietra; Helvetica Chimica Acta; vol. 77; nb.

7; (1994); p. 1999 - 2006, View in Reaxys

Prionitis lanceolata (Harv.) Harvey

Bernart, Matthew; Gerwick, William H.; Phytochemistry (Elsevier); vol. 29; nb. 12; (1990); p. 3697 - 3698, View in Reaxys

the seed balls of sugar beet

Chiji, Hideyuki; Arakawa, Yoshihito; Ueda, Shinji; Kuroda, Mutsumi; Izawa, Masao; Phytochemistry (Elsevier); vol. 25; nb. 1; (1986); p.

281 - 282, View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Streptoverticillium olivoreticuli

Sakai, Shin-ichiro; Aimi, Norio; Yamaguchi, Keiichi; Hitotsuyanagi, Yukio; Watanabe, Chitoshi; et al.; Chemical & Pharmaceutical Bulletin; vol. 32; nb. 1; (1984); p. 354 - 357, View in Reaxys

Pinus sylvestris

Sandberg, Goeran; Jensen, Einar; Crozier, Alan; Phytochemistry (Elsevier); vol. 23; nb. 1; (1984); p. 99 - 102, View in Reaxys

Winter Nelis' pear receptacles

Martin, George C.; Scott, I. M.; Neill, S. J.; Horgan, R.; Phytochemistry (Elsevier); vol. 21; nb. 5; (1982); p. 1079 - 1082, View in Reaxys

Meeresalgen

Abe et al.; Agricultural and Biological Chemistry; vol. 36; (1972); p.

2259, View in Reaxys

isol. aus Lasiodiplodia theobromae-Kulturen

Aldridge,D.C. et al.; Journal of the Chemical Society [Section] C: Organic; (1971); p. 1623 - 1627, View in Reaxys

Tryptamin, Rattenleber-homogenate (in vitro)

Iskric; Kveder; Croatica Chemica Acta; vol. 37; (1965); p. 233, View in Reaxys

Isolierung aus Wirsingkohl

Prochazka; Sanda; Collection of Czechoslovak Chemical Communications; vol. 25; (1960); p. 270,279, View in Reaxys

Reaxys ID 7671060 View in Reaxys

2/9 Chemical Name: 3-indolecarboxylic acid sodium salt; sodium 3indole carboxylate; sodium indole-3-carboxylate Linear Structure Formula: Na(1+)*O2CC8H6N(1-)=NaO2CC8H6N Molecular Formula: C9H6NO2*Na Molecular Weight: 183.142 Type of Substance: heterocyclic InChI Key: XTNBVKGEHGUUEO-UHFFFAOYSA-M Note:

O– O Na + NH

Association (MCS) (2) 1 of 2

Description (Association UV/VIS spectrum of the complex (MCS)) Solvent (Association (MCS))

methanol

Partner (Association (MCS))

1,3,5-Trinitrobenzene

Sepulcri, Patricia; Goumont, Regis; Halle, Jean-Claude; Buncel, Erwin; Terrier, Francois; Chemical Communications; nb. 8; (1997); p. 789 - 790, View in Reaxys 2 of 2

Description (Association NMR spectrum of the complex (MCS)) Solvent (Association (MCS))

tetradeuteriomethanol

Partner (Association (MCS))

1,3,5-Trinitrobenzene

Sepulcri, Patricia; Goumont, Regis; Halle, Jean-Claude; Buncel, Erwin; Terrier, Francois; Chemical Communications; nb. 8; (1997); p. 789 - 790, View in Reaxys

Reaxys ID 3816952 View in Reaxys

3/9

O

Chemical Name: indole-3-carboxylic acid ; S-benzyl-thiuroniumsalt; Indol-3-carbonsaeure; S-Benzyl-thiouronium-Salz Linear Structure Formula: C9H7NO2*C8H10N2S Molecular Formula: C8H10N2S*C9H7NO2 Molecular Weight: 327.407

OH HN S NH

H 2N

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Type of Substance: heterocyclic InChI Key: LSWTUGOVIZKOOB-UHFFFAOYSA-N Note: Melting Point (1) 1 of 1

Melting Point [°C]

157.5

Solvent (Melting Point)

H2O

Comment (Melting Point) Decomp.

Bowden; Marion; Canadian Journal of Chemistry; vol. 29; (1951); p. 1037,1041, View in Reaxys

Reaxys ID 9122752 View in Reaxys

4/9 Chemical Name: [2-14C]-indole-3-carboxylic acid Linear Structure Formula: C8 (14)CH7NO2 Molecular Formula: C9H7NO2 Molecular Weight: 163.149 Type of Substance: heterocyclic InChI Key: KMAKOBLIOCQGJP-RHRFEJLCSA-N Note:

O OH

14CH

NH

Substance Label (1) Label References 11

Pedras, M.Soledade C; Nycholat, Corwin M; Montaut, Sabine; Xu, Yiming; Khan, Abdul Q; Phytochemistry; vol. 59; nb. 6; (2002); p. 611 - 625, View in Reaxys

Reaxys ID 17802262 View in Reaxys

5/9 Chemical Name: 3-indolecarboxylic acid tri(o-fluorobenzyl)tin ester Linear Structure Formula: 3FC6H4CH2 (1-)*Sn(4+)*O CC H N(1-)=(FC H CH )3SnO CC H N 2 8 6 6 4 2 2 8 6 Molecular Formula: 3C7H6F*C9H6NO2*Sn Molecular Weight: 606.231 Type of Substance: Coordination compound InChI Key: PGGFTUVECXDPBB-UHFFFAOYSA-M Note:

–H

C 32 F

O HN

Sn4+

O–

Melting Point (1) 1 of 1

Melting Point [°C]

92 - 93

Solvent (Melting Point)

acetone; hexane

Yin, Handong D.; Wang, Chuanhua; Ma, Chunlin; Wang, Daqi; Journal of Organometallic Chemistry; vol. 689; nb.

1; (2004); p. 246 - 251 ; (from Gmelin), View in Reaxys Conformation (1) Object of Investi- References gation Conformation

Yin, Handong D.; Wang, Chuanhua; Ma, Chunlin; Wang, Daqi; Journal of Organometallic Chemistry; vol.

689; nb. 1; (2004); p. 246 - 251 ; (from Gmelin), View in Reaxys

Crystal Property Description (1) Colour & Other References Properties colorless

Yin, Handong D.; Wang, Chuanhua; Ma, Chunlin; Wang, Daqi; Journal of Organometallic Chemistry; vol.

689; nb. 1; (2004); p. 246 - 251 ; (from Gmelin), View in Reaxys

Solubility (MCS) (1) 1 of 1

Comment (Solubility (MCS))

sol. in many org. solvents (CCl4, CHCl3, benzene, acetone); insol. in hexane, petroleum ether, water

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Yin, Handong D.; Wang, Chuanhua; Ma, Chunlin; Wang, Daqi; Journal of Organometallic Chemistry; vol. 689; nb.

1; (2004); p. 246 - 251 ; (from Gmelin), View in Reaxys NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

1H

Coupling Nuclei

119Sn

Solvents (NMR Spectro- chloroform-d1 scopy) Comment (NMR Spectroscopy)

Signals given

Yin, Handong D.; Wang, Chuanhua; Ma, Chunlin; Wang, Daqi; Journal of Organometallic Chemistry; vol. 689; nb.

1; (2004); p. 246 - 251 ; (from Gmelin), View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Comment (IR Spectroscopy)

458 cm**-1 - 3432 cm**-1

Yin, Handong D.; Wang, Chuanhua; Ma, Chunlin; Wang, Daqi; Journal of Organometallic Chemistry; vol. 689; nb.

1; (2004); p. 246 - 251 ; (from Gmelin), View in Reaxys

Reaxys ID 18577067 View in Reaxys

6/9 Chemical Name: [4',5',6',7'(2)H4]indole-3-carboxylic acid Linear Structure Formula: C9H3 (2)H4NO2 Molecular Formula: C9H7NO2 Molecular Weight: 165.128 InChI Key: KMAKOBLIOCQGJP-RHQRLBAQSA-N Note:

O 2H

OH

2H

2H

NH 2H

Substance Label (1) Label References 20a

Pedras, M. Soledade C.; Okinyo, Denis P. O.; Organic and Biomolecular Chemistry; vol. 6; nb. 1; (2008); p.

51 - 54, View in Reaxys

Reaxys ID 22324476 View in Reaxys O OH

NH

7/9

H 2N

Chemical Name: 4-carbamoylpiperidinium indole-3-carboxylate Linear Structure Formula: C6H12N2O*C9H7NO2 Molecular Formula: C6H12N2O*C9H7NO2 Molecular Weight: 289.334 InChI Key: IYYFSULREOXGBV-UHFFFAOYSA-N Note:

O

N H

Melting Point (1) 1 of 1

Melting Point [°C]

151

Smith, Graham; Wermuth, Urs D.; Journal of Chemical Crystallography; vol. 41; nb. 12; (2011); p. 1850 - 1854, View in Reaxys Crystal Property Description (1) Colour & Other References Properties colourless

Smith, Graham; Wermuth, Urs D.; Journal of Chemical Crystallography; vol. 41; nb. 12; (2011); p. 1850 1854, View in Reaxys

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Reaxys ID 22324479 View in Reaxys

8/9 Chemical Name: 4-carbamoylpiperidinium indole-3-carboxylate hemihydrate Linear Structure Formula: C6H12N2O*C9H7NO2*0.5H2O Molecular Formula: C6H12N2O*C9H7NO2*0H2O Molecular Weight: 298.342 InChI Key: GCVSTTKMBNVRGH-UHFFFAOYSA-N Note:

O OH 0.5 O H 2O

H 2N NH

N H

Crystal Phase (1) Description (Crys- References tal Phase) Dimensions of the Smith, Graham; Wermuth, Urs D.; Journal of Chemical Crystallography; vol. 41; nb. 12; (2011); p. 1850 unit cell 1854, View in Reaxys Crystal System (1) Comment (Crystal References System) Crystal system given

Smith, Graham; Wermuth, Urs D.; Journal of Chemical Crystallography; vol. 41; nb. 12; (2011); p. 1850 1854, View in Reaxys

Interatomic Distances and Angles (1) Description References Interatomic disSmith, Graham; Wermuth, Urs D.; Journal of Chemical Crystallography; vol. 41; nb. 12; (2011); p. 1850 tances and angles 1854, View in Reaxys Space Group (1) Comment (Space Group)

References

Space group(s) given

Smith, Graham; Wermuth, Urs D.; Journal of Chemical Crystallography; vol. 41; nb. 12; (2011); p. 1850 1854, View in Reaxys

Reaxys ID 28074403 View in Reaxys O

9/9 Linear Structure Formula: K(1+)*C9H6NO2 (1-) Molecular Formula: C9H6NO2*K Molecular Weight: 199.25 InChI Key: BKJPHBKTFZIOJA-UHFFFAOYSA-M Note:

O– K+ NH

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