Phytochemical investigation of sapindus emarginatus ijrpp

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International Journal of Research in Pharmacology and Pharmacotherapeutics (Research article)

PHYTOCHEMICAL INVESTIGATION OF SAPINDUS EMARGINATUS *1 A.Krishnaveni, 2Santh Rani Thaakur *1Institute of Pharmaceutical Technology, Sri Padmavathi Mahila Viswavidyalayam(Women’s University), Tirupati, A.P.,, India.

2 Dr.Santh Rani Thaakur, Professor, Institute of Pharmaceutical Technology, Sri Padmavathi Mahila Viswavidyalayam (Women’s University), Tirupati, A.P, India. _____________________________________ _________________________________________________________________ _______________________________ ABSTRACT The hydro alocoholic extract of Sapindus apindus emarginatus

was subjected to column chromatography leading to the th

separation of oleanolic acid and beta amyrin were identified and characterized by physical and spectroscopic methods.

Keywords: Sapindus apindus emarginatus, sapindaceae, oleanolic acid, beta amyrin ______________________________________________________________ _________________________________________________________________________________________ _______________________

Introduction Sapindus emarginatus is a medium sized to the large, deciduous tree found in Andhra Pradesh and Karnataka. It is native of south India, grown on the coast and in open forest at low elevations and in the plains of North India. The fruits preparations are used to treat ear ache, snake bite, ante-partum partum and post partum treatment to induce and restore the normal condition of the uterus after child birth. Roots are used as an expectorant, demulcent [1, 2] and used in hemicranias, hysteria and epilepsy [3]. Leaves are used to treat painful joints, gout and rheumatism [4]. The phytochemical literature of Sapindus emarginatus reported the presence of cyanolipids from the seed oil six saponins from the pericarp[5,6] identified acetylated triterpene saponins such as heragenin 33-o_________________________________ * Corresponding author: A.Krishnaveni, Sri Padmavathy Mahila Viswavidyalayam Viswavidyalayam, Tirupathy, A.P. India E-mail address: akrishnaveni72@rediffmail.com

2-acetyl beta D- xylopyranosylxylopyranosyl (1 3) alpha Lrhamnopyranosyl -(1,2) (1,2) arabinopyranoside, 23 OO acetyl-hederagenin 3- O (4-O O-acetyl-beta -D xylopyranosyl-(1 3), alpha-L-rjhamnopyranosyl rjhamnopyranosyl -(1 2), alpha -Larabinopyranoside andoleanolic acid 3-o3 (4- acetyl-beta -D-xylopyranosyl xylopyranosyl (1 3)-alpha 3) rhamnosyl -(1, (1, 2) arabinopyranoside[7] The plant , exhibited anti fertility effect, anti-inflammatory anti hypotensive, anthelmintic, anticonceptive, antimigraine, anti hyperalgesia effect, dopaminergic and serotonergic effect, antibacterial and antifungal effect, antihyperglycemic and anti-diabetic, anti antihyperlipidemic, anti-ulcer ulcer activity[8-22].

An attempt was carried out to investigate the phytochemical constituents of Sapindus emarginatus. emargi

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MATERIALS AND METHODS: Plant materials The leaves of Sapindus emarginatus were collected from the foot hills of Tirumala, Tirupati, Andhra Pradesh, India. All the plants were authenticated by Dr. Madhava Chetty, Professor, Dept of Botany, S.V. University, Tirupati. Voucher specimens were preserved in the Institute of Pharmaceutical Technology, Sri Padmavati Mahila Visvavidyalayam, Tirupati, Andhra Pradesh, India.

Apparatus required UV-Spectra (Systronics), IR Spectra (Perkin Elmer) spectra was recorded. 1H NMR spectra was obtained (AVIII Bruker, 500 MHz), 13C NMR (AVIII Bruker, 500 MHz) spectra was recorded using the solvents CDCl3 and MeoD. Electro Spray Ionization mass spectra was recorded using HP 1100 MSD.

aliphatic side chain. The 1 H NMR spectrum of the isolated compound showed the presence of protons at various positions at δ 1.7, δ 2.73, δ 3.13 and δ 5.

22 and 0.637 indicated the presence of allelic group, benzylic group, alkyl chloride and hydroxide (R-OH) and primary R-CH3 respectively. The 13C NMR Spectrum showed the characteristic signals of aromatic carbon relevant to δ 191.39, δ163.86, δ 1332.53, δ 128.85, and δ 116.32 indicated the presence of (steroidal) carbon. The mass spectrum showed the fragments and fragmentation at 443 (M+) m/z 416, 399, 379, 366, 340, 295, 281, 242, 222, 206, 180,147,123, 101, 85 and 73 indicated the presence of C2H3, oxygen atom, HF, methylene group, C2H2, CH2CH2OH, CH2, C3H3, HF2, oxygen atom, C2H2, CH2F, C=C, methyl group and carbon group respectively. The molecular formulae was C29 H48 O3.

The data were compared and upon close proximity with the earlier literature, the compound SE-1 was identified as oleanolic acid [23].

Processing of the material The collected plant material was dried in shade, coarsely powdered and subjected to extraction and stored in air tight container for further use.

Extraction and isolation Dried plant material were ground to coarse powder was defatted with petroleum ether(60-80°C,4 hours) using soxhlet extractor, further with extracted hydroalcohol (70%v/v) until the exhaustion of the material. The extract was evaporated under reduced pressure, and the residue was subjected to column chromatography. The column was prepared in ethyl acetate and left overnight; the column contents were eluted with gradient elution starting with pet ether: toluene followed by chloroform, ethyl acetate, methanol and water (90:10, 70:30, 50:50, 30:70 and 10:90). Chloroform (20:80) and ethyl acetate: Methanol (50:50) eluted the compound SE - 1 and SE - 2 was separated and characterized by physical, chemical and spectral studies.

Spectral analysis of SE-1 Dull white, needle shaped crystals, and insoluble in water. UV λ max: 202 and 236 nm. FT-IR: V mcm1 :3433, 3005, 2925, 2855, 2674, 1712, 1457, 1413, 1377, 1247, 1117, 1094, 939, 723, 605,480 indicated the presence of the additional mono substituted

Spectral analysis of SE-2 Pale, yellow and soluble in water. UV λ max: 214 nm.FT-IR: V cm-1: 3410, 2963, 1609, 1417, 1167,799, 1052. The 1H NMR spectrum showed the characteristic protons relevant to 7 methyl group at δ 0.989 (J=1.00) , δ 1.023(J=1.00), δ 1.1227(J=1.00), δ 1.252(J=1.00), δ 1.306(J=1.00), δ 1.356(J=1.00), δ1.457(J=1.00), δ1.508(J=1.00), δ1.535(J=1.00), δ1.556(J=1.00). Various positions of protons at δ 2.882 (J=2.36), δ 3.268(J=2.36), δ 3292(J=2.36), δ 3.333(J=2.36), δ 3.481(J=2.36), δ3.537(J=2.36), δ 3.585(J=2.36), δ 3.605(J=2.36), δ 3.678(J=2.36), δ 3.717(J=2.36), δ3.749(J=1.32), δ 778(J=1.32), δ 3.819(J=1.32), δ 3.845J=1.32), δ 3.881JJ=1.32), δ3.911(J=1.32) and δ 3.944(J=1.32), δ 3.954((J=1.32). δ 3.980(J=1.32), δ 4.067(J=1.32), δ 4.078(J=1.32), δ 4.102(J=1.32). δ4.112 (J=1.32), δ 4.212(J=1.32), δ 4.235(J=1.32), δ 4.274(J=1.32), δ 4.357(J=1.32), δ4.387(J=1.32), δ 4.456 (J=1.32) δ 4.512(J=1.32), δ 4.540(J=1.32), δ4.758(J=1.32), δ 4.787(J=1.32), δ 4.815(J=1.32) indicated the presence of aromatic (steroidal) proton. The 13C NMR spectrum showed the characteristic signals of carbon relevant to the position at 1, 3, 5, 7, 10, 11, 12, 13, 15, 17, 18, 19, 21, 22, 23, 28, 29, 30 at δ 38.78, 77.79,50.08, 23.08, 39.84, 25.34, 140.94,33.82,121.69,50.08, 56.74, 51.02, 37.31, 31.89,31.80,42.33, 29.74,19.09: 29.74,19.58, 23.08

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95 A.Krishnaveni et al / Int. J. of Res. in Pharmacology and Pharmacotherapeutics Vol-1(2) 2012 [93-96]

indicated the presence of aromatic carbon. The mass spectrum showed the fragments and fragmentation at 679.5 (M+), m/z 680, 663, 618, 600, 454, 453, 397, 395, 340, 302, 279, 258,236,186,150,138,135, and 122 indicated the presence of HF, OH group, CH2=CHCHCH2, H2O, phthaleic anhydride, one, hydrogen, CH 2=CHCHCH2CH3, two hydrogen atoms, CH3 CHOH, C3H2, HF+ hydrogens H= HF, H 2 H F, CH3Cl, two molecules of water, one carbon, three hydrogens and CH atom respectively. The data was compared and upon close proximity with the earlier literature, the compound SE-2 was identified as beta amyrin [24].

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Conclusion These compounds SE-1 and SE-2 were being reported for the first time from the leaf of Sapindus emarginatus. Further research is in progress towards its pharmaocological action.

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