DimericSesquiterpenoids
Shang-GaoLiaoandJian-MinYue
Contents
1Introduction..
2ClassificationandDistribution ...............................................................3
2.1DisesquiterpenoidDSs.................................................................4
2.1.1BisabolaneDisesquiterpenoids......................
2.1.2GermacraneDisesquiterpenoids ..............................................5
2.1.3Guaiane,Pseudoguaiane,andXanthaneDisesquiterpenoids ...............6
2.1.4EremophilaneDisesquiterpenoids ............................................10
2.1.5CadinaneDisesquiterpenoids .................................................13
2.1.6EudesmaneDisesquiterpenoids ..............................................14
2.1.7LindenaneDisesquiterpenoids ...............................................15
2.1.8Cuparane,Cyclolaurane,andHerbertaneDisesquiterpenoids
2.1.9MiscellaneousDisesquiterpenoids. ..........................................19
2.1.10CompoundDisesquiterpenoids...............................................23
2.2Pseudo-disesquiterpenoids.............................................................26
2.2.1DimericAza-sesquiterpenoids......
2.2.2MiscellaneousPseudo-disesquiterpenoids....................................27
3.3NuclearMagneticResonanceSpectroscopy..
S.-G.Liao
SchoolofPharmacy,GuizhouMedicalUniversity,ZhangjiangHi-TechPark,Shanghai 201203,People’sRepublicofChina
EngineeringResearchCenterfortheDevelopmentandApplicationofEthnicMedicine andTCM(MinistryofEducation),SchoolofPharmacy,GuizhouMedicalUniversity, Guizhou550004,People’sRepublicofChina
e-mail: lshangg@163.com
J.-M.Yue(*)
SchoolofPharmacy,GuizhouMedicalUniversity,ZhangjiangHi-TechPark,Shanghai 201203,People’sRepublicofChina
e-mail: jmyue@simm.ac.cn
© SpringerInternationalPublishingSwitzerland2016
A.D.Kinghorn,H.Falk,S.Gibbons,J.Kobayashi(eds.), ProgressintheChemistry ofOrganicNaturalProducts,Vol.101,DOI10.1007/978-3-319-22692-7_1
3.5CDandECDCalculations.............................................................38
3.6ChemicalMethods.....................................................................39
3.7StructuralElucidationofSerratustoneA..............................................41
4BiologicalActivity...........................................................................45
4.1CytotoxicandAntitumorActivity .....................................................45
4.2Anti-inflammatoryActivity............................................................59
4.3ImmunosuppressiveActivity... .......................................................66
4.4PotassiumChannelBlockingandCardiovascularActivity ...........................67
4.5Antimalarial,Antiprotozoal,Antibacterial,Antifungal,andAntiviralActivity .....69
4.6NeurotrophicActivity ..................................................................72
4.7MiscellaneousActivities...............................................................73
5Synthesis.. ....................................................................................74
5.1Biogenesis..............................................................................75
5.1.1[4+2]Diels–AlderReactions .................................................75
5.1.2[2+2]Cycloadditionand[6+6]Cycloaddition. .............................82
5.1.3RadicalReactions..............................................................83
5.1.4AldolReactions................................................................84
5.1.5Esterification,Etherification,andAcetal-FormationReactions.. ............85
5.1.6DimerizationThroughaLinker ...............................................85
5.1.7Michael-TypeReactions.......................................................86
5.2ChemicalSynthesis..... ...............................................................87
5.2.1Diels–AlderCycloaddition ....................................................87
5.2.2OxidativeCoupling............................................................93
5.2.3DimerizationwithLinkers. ....................................................95
5.2.4MiscellaneousDimerizationMethods... ......................................96
6Conclusions ...................................................................................98
1Introduction
Itiswidelyacceptedthatalargenumberofproteinsresponsibleforcellular functionexistasdimers(hetero-orhomo-)orneedtobeactivatedbydimerization beforemediatingcertainsignalingpathways[1, 2].Simultaneouslytargetingboth monomericmoietiesofthedimericproteinshasshownpotentialinthedevelopment ofvarioustherapeuticagents[3–5].Asnaturalorsyntheticdimericmolecules mightbeabletoactonbothmoietiesofadimericprotein,dimericsesquiterpenoids (DSs),whicharegeneratedbiogeneticallyfromcouplingoftwosesquiterpenoid molecules(eitheridenticalordifferent),areinessencepotentialbiologicallyactive moleculesandhaveattractedgreatattentioninrecentyearsfortheirparticular structuresandbiologicalactivities.Withacompositionofatleast30carbons,and theirgenerationfromsesquiterpenoidsofavarietyofstructuraltypes,andin showingvariationsoftheconnectingpatternsofthetwoidentical(forhomo-DS) ordifferent(forhetero-DS)sesquiterpenoidunits,thismakestheelucidationofDS structuresandtheirsyntheticconstructionquitechallenging.Moreover,thebiologicaleffectsoftheDSs,particularlytheirpotentialanti-inflammatory,antimalarial,
antitumor,antiviral,immunosuppressive,neurotropic,andpotassiumchannel blockingactivities,haverenderedthesemoleculespromisingcandidatesforfurther drugdevelopment.AgeneraltrendobservedisthatsomeDSsaremorepotentthan theirmonomericprecursorsformanybiologicalactivities.
TworecentreviewshavebeenwrittenbyZhanetal.[6]andLianandYu[7], coveringtheisolation,structuraldetermination,biologicalactivities,biogenesis, andsynthesisofnaturalDSsuptoJune2010.
Inthiscontribution,ageneralviewoftheclassificationanddistributionofDSs (includingthosereportedrecently)willbeprovided.Strategiesforthestructural elucidationofDSsandtheiranalogueswillbepresented.Chemicaleffortstoward theconstructionofDSs,particularlystrategiesfortheconvergenceofthetwo sesquiterpenoidunits,willbereviewed.Moreover,thebiologicalactivitiesof DSswillbediscussedundereachtypeofactivityforthepurposesofproviding informationregardingthestructuralfeaturesrequiredbytheirtargetproteins.
2ClassificationandDistribution
Basedoncouplingpatternsandstructuralfeaturesofthetwoconstitutional sesquiterpenoidunits,DSscanbeclassifiedintodisesquiterpenoids(typeA)and pseudo-disesquiterpenoids(typeB)[6].IntypeA,twosesquiterpenoidunitsare connecteddirectlybyatleastoneC–Cbond.Incontrast,intypeB,thetwounitsare changedtotwoaza-sesquiterpenoidmoieties,orareconnectedbyanestergroup,an O-/S-etherlinkage,oneortwoamidegroups,oranitrogen/ureagroup.Dimerosesquiterpenoids[6],whichoriginatefromcouplingoftwomerosesquiterpenoids thatarebiogeneticallyformedfromdirectcarbon-carbonconnectionofa sesquiterpenoidandanonsesquiterpenoid,arenotincludedamongtheDSgroup. Takingintoconsiderationthestructuraltypesofmonomericsesquiterpenoids, disesquiterpenoids(typeA)canalsobeclassifiedintobisabolane,germacrane, guaiane,eremophilane,cadinane,eudesmane,lindenane,miscellaneoussesquiterpene,andcompounddisesquiterpenoids.Compounddisesquiterpenoidsreferto thoseDSsthatareformedbycouplingoftwosesquiterpenoidunitsofdifferent structuraltypes.Pseudo-disesquiterpenoids(typeB)mayalsohavesimilarconstitutions,butwillnotbediscussedinthisrespect.Itshouldbenotedthatsincenon-carboncarbon-connectedpseudo-disesquiterpenoidsaremorepronetometabolismtothe constitutionalmonomersortheirderivativesbeforereachingthetargetproteins,DSs oftypeAanddimericaza-sesquiterpenoidsseemtobeofgreateroverallimportance.
2.1DisesquiterpenoidDSs
2.1.1BisabolaneDisesquiterpenoids
DimericsesquiterpenoidsofthistypearegenerallypresentineitherthePlantae (plant)orAnimalia(sponge)kingdoms(Table 1).Thegenera Perezia, Coreocarpus, and Baccharis fromtheAsteraceaeandthegenus Meiogyne fromtheAnnonaceaein theplantkingdom,aswellas Axinyssa (Halichondriidae)and Lipastrotethya (Dictyonellidae)intheanimalkingdomarereportedtoproducebisabolanedisesquiterpenoids.However,onebisabolanedisesquiterpenoid,disydonolC(1),hasbeen reportedtooccurinamarine-derivedfungus(Aspergillus sp.)(Fig. 1)[13]
Table1 BisabolaneDSs
CompoundOriginFamilyKingdomRef.
Bacchopetiolone
60 ,6-Bis-2-(1,5-dimethyl-1,4benzoquinone
60 ,6-Bis-2-(1,5-dimethyl-4-hexenyl-6isovaleroxy)-3-hydroxy-5-methyl-1,4benzoquinone
cis-DimerA
cis-DimerA
cis-DimerB
cis-DimerB
DicurcuphenolsA–E
Diperezone/biperezone
Diperezone/biperezone
DisydonolC(1)
1-epi-MeiogyninA
MeiogyninA
trans-DimerC
trans-DimerC
trans-DimerD
Baccharis petiolata
Coreocarpus arizonicus
Coreocarpus arizonicus
Axinyssa variabilis
Lipastrotethya ana
Axinyssa variabilis
Lipastrotethya ana
Didiscus aceratus
Coreocarpus arizonicus
Perezia alamani var. oolepis
AsteraceaePlant[8]
AsteraceaePlant[9]
AsteraceaePlant[9]
HalichondriidaeAnimal (sponge) [10]
DictyonellidaeAnimal[10]
HalichondriidaeAnimal[10]
DictyonellidaeAnimal[10]
HeteroxyidaeAnimal (sponge) [11]
AsteraceaePlant[9]
AsteraceaePlant[12]
Aspergillus sp.TrichocomaceaeFungi[13]
Meiogyne cylindrocarpa
Meiogyne cylindrocarpa
Lipastrotethya ana
Axinyssa variabilis
Axinyssa variabilis
AnnonaceaePlant[14]
AnnonaceaePlant[14]
DictyonellidaeAnimal[10]
HalichondriidaeAnimal[15]
HalichondriidaeAnimal[15]
2 (dicurcuphenol B)
3 (dicurcuphenol C)
Fig.1 Structuresofbisabolane,disydonolC(1),anddicurcuphenolsB(2)andC(3)
2.1.2GermacraneDisesquiterpenoids
Dimericsesquiterpenoidsofthistypeareveryrare.Uptothepresent,onlyafew speciesinthefamiliesAristolochiaceae,Asteraceae,andZingiberaceaehavebeen reportedtoaccumulatethesecompounds.Germacranedisesquiterpenoidsarerigidlyconfinedtotheplantkingdom(Table 2,Fig. 2).
6S.-G.LiaoandJ.-M.Yue
Table2 GermacraneDSs
CompoundOriginFamilyRef.
Artebarrolide
Difurocumenone
Elegain
HelivypolideG
Artemisiabarrelieri
Curcumazedoaria
Gonospermumelegans
Helianthusannuus
Mikagoyanolide(4) Mikaniagoyazensis
Mikagoyanolide(4) Tanacetopsismucronata
Versicolactone
Fig.2 Structuresof germacraneand mikagoyanolide(4)
Aristolochiaversicolor
Asteraceae[16]
Zingiberaceae[17]
Asteraceae[18]
Asteraceae[19]
Asteraceae[20]
Asteraceae[21]
Aristolochiaceae[22]
2.1.3Guaiane,Pseudoguaiane,andXanthaneDisesquiterpenoids
Dimericsesquiterpenoidsoftheseclassesmaycontaintwoguaiane,pseudoguaiane, secoguaiane,orxanthaneunits(Fig. 3),andareoneofthelargestaggregategroupsof DSs.Asteraceae,whichproducesaconsiderablenumberofguaianesesquiterpenoids, isalsothemajorfamilyproducingguaianedisesquiterpenoids(Table 3). Artemisia is amongthemostimportantgeneraofthisfamily,fromamedicinalperspective. Severalspeciesinthisgenushavebeenreportedtobeguaianedisesquiterpenoid sources.Inaddition, Daphneoleoides oftheThymelaeaceae[33], Salvianubicola of theLamiaceae, Joannesiaprinceps oftheEuphorbiaceae[41],andtwospecies(i.e. Xylopiaaromatica [58]and Xylopiavielana [71])oftheAnnonaceaefamilywerealso reportedtocontainDSs.ItisnoteworthythatDSsofthesetypesarelimitedtothe plantkingdom.
germacrane
Fig.3 Structuresof guaiane,pseudoguaiane, xanthane,diguaiaperfolin (5),pungiolideA(6),and 7
xanthane pseudoguaiane
Table3 Guaiane,pseudoguaiane,andxanthaneDSs
CompoundOriginFamilyRefs.
Absinthin Artemisia absinthium
Absinthin Artemisia caruifolia
Absintholide Artemisia caruifolia
Absintholide Artemisia absinthium
Asteraceae[23, 24]
Asteraceae[25]
Asteraceae[25]
Asteraceae[26]
Achicollinolide Achilleacollina Asteraceae[27]
AchillininsB–Ca Achillea millefolium
AinsliadimerA Ainsliaea macrocephala
AinsliadimerB Ainsliaea fulvioides
Anabsin Artemisia absinthium
Anabsin Artemisia caruifolia
Asteraceae[28]
Asteraceae[29]
Asteraceae[30]
Asteraceae[31]
Asteraceae[25] (continued)
Table3 (continued)
CompoundOriginFamilyRefs.
Anabsinthin Artemisia absinthium Asteraceae[31]
Anabsinthin Artemisia anomala Asteraceae[32]
Anabsinthin Artemisia caruifolia Asteraceae[25]
Anabsinthin Daphneoleoides Thymelaeaceae[33]
ArtabsinolideB Artemisia caruifolia Asteraceae[25]
ArtanomadimersA F Artemisia anomala Asteraceae[34]
ArtanomalideD Artemisia anomala Asteraceae[32]
ArtanomaloideA Artemisia anomala Asteraceae[32, 35]
Artelein Artemisia leucodes Asteraceae[36]
Artenolide Artemisia absinthium Asteraceae[37]
Artesieversin Artemisia sieversiana Asteraceae[38]
ArtselenoideA Artemisia selengensis Asteraceae[39, 40]
ArtselenoideA Artemisia sylvatica Asteraceae[40]
Assufulvenal Joannesia princeps Euphorbiaceae[41]
BienninC Hymenoxys biennis Asteraceae[42]
2,120 -Bis-hamazulenyl Ajaniafruticulosa Asteraceae[43]
Bisnubenolide Salvianubicola Lamiaceae[44]
Bisnubidiol Salvianubicola Lamiaceae[45]
Bistataxacin Salvianubicola Lamiaceae[46]
CaruifolinsB–D Artemisia caruifolia Asteraceae[25]
ChrysanolideC Chrysanthemum indicum Asteraceae[47]
Decathieleanolide Decachaeta thieleana
Asteraceae[48]
10-DesoxygochnatiolideA Gochnatia polymorpha Asteraceae[49]
10-DesoxygochnatiolideA Gochnatia polymorpha ssp. floccosa
Asteraceae[49]
10-Desoxy-10β -H-gochnatiolideA Gochnatia hypoleuca Asteraceae[49]
DichrocepholidesD–E Dichrocephala integrifolia Asteraceae[50] (continued)
Table3 (continued)
CompoundOriginFamilyRefs.
Diguaiaperfolin(5) Eupatorium perfoliatum
Dihydroornativolide
8β ,80 β -Dihydroxy-10-desoxy-10β -HgochnatiolideA
DistansolidesA–B
Geigeriaornativa
Gochnatia hypoleuca
Asteraceae[51]
Asteraceae[52]
Asteraceae[49]
Achilleadistans Asteraceae[53] 10,11-Epiabsinthin
100 ,11,110 -epi-Absinthin
100 ,110 -epi-Absinthin
11-epi-Absinthin
110 -Epimaritimolide
Gnapholide
GochnatiolideA
GochnatiolideA
GochnatiolideB
Handelin(YejuhuaLactone/Chrysanthelide)
Helisplendidilactone
2α-Hydroxy-10-desoxy-1,10-dehydrogochnatiolideA
2α-Hydroxy-10-desoxy-1,10-dehydro11α,13,110 α,130 -tetrahydrogochnatiolideA
8β -Hydroxy-10-desoxy-10β -H-gochnatiolide A
Artemisia caruifolia
Artemisia sieversiana
Artemisia sieversiana
Artemisia sieversiana
Ambrosia maritima
Pulicaria gnaphalodes
Gochnatia polymorpha
Gochnatia paniculata
Gochnatia paniculata
Handelia trichophylla
Helichrysum splendidum
Gochnatia polymorpha
Gochnatia polymorpha
Gochnatia hypoleuca
8-Hydroxy-10-desoxygochnatiolideA Gochnatia polymorpha
8-Hydroxy-10-desoxygochnatiolideA Gochnatia polymorpha ssp. floccosa
80 β -Hydroxy-10-desoxy-10β -HgochnatiolideA
(11α,12β ,13α,21β )-7-Hydroxy-16-oxo-17isopropylidene-lα,5,5,9β ,14α,20hexamethyl-6-oxaheptacyclo[l0.9. 1.02.10.04.7.012.24.013.19]docosa-2(l0),3,l9triene
Gochnatia hypoleuca
Xylopiaaromatica
Asteraceae[25]
Asteraceae[38]
Asteraceae[38]
Asteraceae[38]
Asteraceae[35]
Asteraceae[54]
Asteraceae[49]
Asteraceae[55]
Asteraceae[55]
Asteraceae[56]
Asteraceae[57]
Asteraceae[49]
Asteraceae[49]
Asteraceae[49]
Asteraceae[49]
Asteraceae[49]
Asteraceae[49]
Annonaceae[58] (continued)
Table3 (continued)
CompoundOriginFamilyRefs.
8α-Hydroxyxeranthemolide
Anthemis austriaca
Isoabsinthin Artemisia absinthium
LineariifolianoidsEb
LineariifolianoidsF–G
Asteraceae[59]
Asteraceae[60]
Inulalineariifolia Asteraceae[61]
Inulalineariifolia Asteraceae[61]
Maritimolide Ambrosia maritima Asteraceae[35]
MexicaninF
Microlenin
Microleninacetate
Helenium mexicanum
Helenium microcephalum
Helenium microcephalum
MillifolidesA–Bc Achillea millefolium
Asteraceae[62]
Asteraceae[63, 64]
Asteraceae[65]
Asteraceae[66]
8-O-Acetylarteminolide Artemisia anomala Asteraceae[32]
Ornativolide Geigeriaornativa Asteraceae[52]
(5S,6R,7R,8R,11R)-2-Oxo-8tigloyloxyguaia-1(10),3-dien-6,12-olide14-carboxylicacid
PungiolideCd
Eupatorium perfoliatum
Asteraceae[67]
Xanthium strumarium Asteraceae[68]
PungiolidesA B Xanthiumpungens Asteraceae[69]
PungiolidesD–Ed Xanthium sibiricum Asteraceae[70]
Seemarin Daphneoleoides Thymelaeaceae [33]
VielaninA–C Xylopiavielana Annonaceae[71]
VielaninsD–E Xylopiavielana Annonaceae[72]
Xeranthemolide Anthemis austriaca Asteraceae[59]
Unnamed(7) Chrysanthemum indicum Asteraceae[73]
a1,10-Secoguaiaolide-guaiaolide bGuaiane-pseudoguaiane c1,10-Secoguaianolide-1,10-secoguaianolide dXanthane-xanthane
2.1.4EremophilaneDisesquiterpenoids
Eremophilanedisesquiterpenoidsgenerallyoccurintheplantkingdom(Table 4)as dimericfuranoeremophilanesordimericeremophilenolides(Fig. 4)[6].Mostofthe eremophilaneDSsfoundtodatehavebeenisolatedfromspeciesintheAsteraceae, with Ligularia beingthemostprevalentgenusinthisregard.
DimericSesquiterpenoids11
Table4 EremophilaneDSs
CompoundOriginFamilyRef.
AdenostinA
Cacalia adenostyloides
AdenostinA Ligularia virgaurea
AdenostinB Cacalia adenostyloides
14-Angeloyloxy-12-(cacalohastin-14-yl) cacalohastine
Bi-3β -angeloyloxy-8β -hydroeremophil-7 (11)-en-12,8α(14b,6a)-diolide
Bieremoligularolide
Biliguhodgsonolide
Biligulaplenolide
Senecio canescens
Ligularia lapathifolia
Ligularia muliensis
Ligularia hodgsonii
Ligularia platyglossa
α,α0 -Bis-3β-angeloyloxyfuranoeremophilane Farfugium japonicum
9β ,90 α-Bis-1,8-dihydroligularenolidea Bedfordia salicina
9β ,90 β -Bis-1,8-dihydroligularenolidea Bedfordia salicina
12-(Dehydrocacalohastin-14-yl)cacalohastin (8)
12-(Dehydrocacalohastin-14-yl)cacalohastin (8)
(1S*,5S*,10aR*)-1-[(80 S*,8a0 R*)-80 ,8a0 -
Dimethyl-40 -oxo-10 ,40 ,60 ,70 ,80 ,8a0hexahydronaphthalen-20 -yl]-4-hydroxy1,4,5,10α-tetramethyl1,2,3,4,5,6,7,9,10,10a-decahydroanthracen9-one
(4aR,4aR,5S,5S,9aR,9aR)4,4,4a,4a,5,5,6,6,7,7,8,8-Dodecahydro3,3,4a,4a,5,5-hexamethyl-2H,2H-9a,9abinaphtho[2,3-b]furan-2,2-dionea
8β -[Eremophila-30 ,70 (110 )-dien120 ,80 α;150 ,60 α-diolide]-eremophil-3,7(11)dien-12,8α;15,6α-diolide
8β -[Eremophila-30 ,70 (110 )-diene120 ,80 α;140 ,60 α-diolide]eremophila-3,7(11)diene-12,8α;14,6α-diolide
Fischelactone
Asteraceae[74]
Asteraceae[75]
Asteraceae[74]
Asteraceae[76]
Asteraceae[77]
Asteraceae[78]
Asteraceae[79]
Asteraceae[80]
Asteraceae[81]
Asteraceae[82]
Asteraceae[82]
Senecio canescens
Seneciocrispus
Eremophila mitchelli
Asteraceae[78]
Asteraceae[83]
Scrophulariaceae[84]
Senecio tsoongianus
Ligularia atroviolacea
Ligularia atroviolacea
Asteraceae[85]
Asteraceae[86]
Asteraceae[87]
Ligulariafischeri Asteraceae[88]
FischelactoneB(9) Ligulariafischeri Asteraceae[89]
(5S )-5,6,7,7a,7b,12b-Hexahydro3,4,5,11,12b-pentamethyl-10-[(3E )-pent-3en-1-yl]-furo[300 ,200 :60 ,70 ]naphtho[10 ,80 : 4,5,6]pyrano[3,2-b]benzofuran-9-ol
(4aR,5S,9aS )-4a,5,6,7,8,9a-Hexahydro3,4a,5-trimethyl-9a-[(4aR,5S,9aR)-
Ligularia virgaurea
Senecio tsoongianus
Asteraceae[90]
Asteraceae[85] (continued)
Table4 (continued)
CompoundOriginFamilyRef.
4,4a,5,6,7,8-hexahydro-3,4a,5-trimethyl-2oxonaphtho[2,3-b]furan-9a(2H )-yl]naphtho[2,3-b]furan-2(4H )-one(10)
LigulamulieninsA–B
LigularinA
LigulolideB
LigulolideD
2-{[(5S )-5,6,7,8-Tetrahydro-9-hydroxy-3,5dimethylnaphtho[2,3-b]furan-4-yl]methyl}3,5-dimethyl-6-[(3E )-pent-3-en-1-yl]-1benzofuran-4,7-dione
Ligularia muliensis
Ligularia virgaurea ssp. oligocephala
Ligularia virgaurea ssp. oligocephala
Ligularia virgaurea ssp. oligocephala
Ligularia virgaurea
Tetrahydromitchelladione Eremophila mitchelli
VirgaurinA Ligularia virgaurea
VirgaurinA Ligularia virgaurea
VirgaurinB Ligularia virgaurea
VirgaurinC Ligularia virgaurea
VirgaurolsA–B Ligularia virgaurea
→6)-Furanoeremophilane
Fig.4 Structuresof eremophilaneandits disesquiterpenoids 8, fischelactoneB(9),and 10
Asteraceae[91]
Asteraceae[92]
Asteraceae[93]
Asteraceae[92]
Asteraceae[90]
Scrophulariaceae[84, 94]
Asteraceae[75, 90, 95]
Asteraceae[90, 96]
Asteraceae[75, 97, 98]
Asteraceae[75, 98]
Asteraceae[95]
2.1.5CadinaneDisesquiterpenoids
Dimericsesquiterpenoidsofthisclassareveryrare(Table 5).Speciesofthegenus Gossypium inthefamilyMalvaceaeseemtobeagoodsourceofcadinanedisesquiterpenoids(Fig. 5).Inaddition, Curcumaparviflora fromtheZingiberaceaefamily alsohasbeenreportedtoproduceanumberofcadinanedisesquiterpenoids [110, 112, 113].
Table5 CadinaneDSs
CompoundOriginFamilyRefs.
Aquatidial
Bicalamenene
(5S,50 R,8S,80 S)-5,50 -diisopropyl-3,30 ,8,80tetramethyl-5,50 ,6,60 ,7,70 ,8,80 -octahydro[1,20 -binaphthalene]-10 ,2-diol
8-Bis(7-hydroxycalamenene)
8-Bis(7-hydroxycalamenene)
(+)-7,70 -Bis[(5R,7R,9R,10S )-2-oxocadinan-3,6 (11)-dien-12,7-olide]
Dicadalenol
6,60 -Dimethoxygossypol
6,60 -Dimethoxygossypol
Gossypol(11)
Gossypol(11)
60 -Methoxygossypol
60 -Methoxygossypol
Pachira aquatica
Dysoxylum alliaceum
Ocotea corymbosa
Heritiera ornithocephala
Siparuna macrotepala
Eupatorium adenophorum
Heterotheca inuloides
Gossypium barbadense
Gossypium hirsutum
Gossypium barbadense
Gossypium hirsutum
Gossypium barbadense
Gossypium hirsutum
ParvifloreneA Curcuma parviflora
ParvifloreneJ Curcuma parviflora
ParviflorenesB–F Curcuma parviflora
ParviflorenesG–I Curcuma parviflora
Malvaceae[99]
Meliaceae[100, 101]
Lauraceae[102]
Malvaceae[103]
Monimiaceae[104]
Asteraceae[105]
Asteraceae[106]
Malvaceae[107]
Malvaceae[107]
Malvaceae[108]
Malvaceae[108, 109]
Malvaceae[107]
Malvaceae[107]
Zingiberaceae[110]
Zingiberaceae[111]
Zingiberaceae[111, 112]
Zingiberaceae[111, 113]
Fig.5 Structuresof cadinaneandits disesquiterpenoidsgossypol (11)andparvifloreneG(12)
2.1.6EudesmaneDisesquiterpenoids
Eudesmanedisesquiterpenoidsaregenerallypresenteitherasdimersoftwo eudesmaneunits(e.g. 13 and 14)orasthoseofbothaneudesmaneanda secoeudesmanesesquiterpenoidcomponent(e.g., 15)(Fig. 6).Currently,only eleveneudesmaneDSshavebeenreported(Table 6).Again,theAsteraceaeisthe mainplantfamilythatproducesthistypeofDSs.
Fig.6 Structuresof eudesmaneandits disesquiterpenoids bialantolactone(13), 14, andfoveolideB(15)
Table6 EudesmaneDSs
CompoundOriginFamilyRef.
Bialantolactone(13)
Biatractylolide
Biatractylolide
Biepiasterolide
Biepiasterolide
Inulahelenium Asteraceae[114]
Atractylodes macrocephala
Trattinickia rhoifolia
Atractylodes macrocephala
Trattinickia rhoifolia
Asteraceae[115]
Asteraceae[116]
Asteraceae[117]
Asteraceae[118]
Bilindestenolide Lindera strychnifolia Lauraceae[119]
3aa,30 ,40 ,5,6.7,8,8a,9,9a-Decahydro-5β -8αβ -50(4aβ -methyl-8-methyliden-2β -naphthyl)spiro[naphtha[2,3-b]furan-3,20 -20 H-pyran]-2(3H )-one
4a,50 -Ethenyl-4β -methyl-3β -[(1-methylethenyl) cyclohex-1β -yl]-3a,30 ,40 ,5,6,7,8,8a.9,9a-decahydro5β ,8αβ -dimethylspiro[naphtha[2,3-b]furan-3,20 -20 Hpyran]-2(3H )-one(14)
50 ,4a-Ethenyl-4β -methyl-3β -[(1-methylethenyl) cyclohex-1β -yl]-3a,30 ,4,40 ,4a,5,6.7,8,8a,9,9adodecahydro-8aβ -methyl-15-methylidenspiro[naphtha[2,3-b]furan-3,20 -20 H-pyran]-2(3H )-one
Helenium autumnale Asteraceae[120]
Helenium autumnale Asteraceae[120]
Helenium autumnale Asteraceae[120]
FoveolideB(15) Ficusfoveolata Moraceae[121]
Fruticolide Ferreyranthus fruticosus Asteraceae[122]
Hydroxy-bis-dihydroencelin Montanoa speciosa Asteraceae[123]
MuscicolidesA–B Frullania muscicola Frullaniaceae[124]
2.1.7LindenaneDisesquiterpenoids
LindenanedisesquiterpenoidsareoneofthelargestclassesofDSs.However,upto thepresent,theseDSshavebeenfoundonlyintheplantkingdomandareconfined tothefamilyChloranthaceae(seeTable 7 inthecurrentchapterandTable2ofthe reviewbyZhanetal.[6]). Chloranthus and Sarcandra aretheonlytwogenerathat havebeenreportedtoproducethistypeofDS(Fig. 7,Plate 1).
Table7 LindenaneDSsisolatedinrecentyears(2010–2013)
CompoundOriginFamilyRef.
ChloramultilideA Chloranthusserratus Chloranthaceae[125]
ChloramultilideC Chloranthuselatior Chloranthaceae[126]
ChloramultilideC Chloranthusmultistachys Chloranthaceae[127]
ChloramultilideD Chloranthusmultistachys Chloranthaceae[127]
ChloramultiolG(16) Chloranthusmultistachys Chloranthaceae[128]
ChloramultiolsA–F Chloranthusmultistachys Chloranthaceae[127] (continued)
Table7 (continued)
CompoundOriginFamilyRef.
CycloshizukaolA Chloranthusfortunei Chloranthaceae[129]
CycloshizukaolA Chloranthusmultistachys Chloranthaceae[127]
HenriolA Chloranthusserratus Chloranthaceae[125]
HenriolD Chloranthusfortunei Chloranthaceae[129]
MultistalidesA–B
SarcandrolidesA–E
SarcandrolidesF–J
Chloranthusmultistachys Chloranthaceae[130]
Sarcandraglabra Chloranthaceae[131]
Sarcandraglabra Chloranthaceae[132]
SarcanolidesA–B Sarcandrahainanensis Chloranthaceae[133]
ShizukaolB Chloranthusspicatus Chloranthaceae[134]
ShizukaolB Chloranthusfortunei Chloranthaceae[129]
ShizukaolB Chloranthusjaponicus Chloranthaceae[135]
ShizukaolC Chloranthusspicatus Chloranthaceae[134]
ShizukaolC Chloranthusmultistachys Chloranthaceae[127]
ShizukaolC Chloranthusfortunei Chloranthaceae[129]
ShizukaolD Chloranthusfortunei Chloranthaceae[129]
ShizukaolD Chloranthusmultistachys Chloranthaceae[127]
ShizukaolH Chloranthusspicatus Chloranthaceae[134]
ShizukaolsB,D Chloranthusserratus Chloranthaceae[125]
ShizukaolsE,G,M,O Chloranthusfortunei Chloranthaceae[129]
SpicachlorantinB Chloranthusmultistachys Chloranthaceae[127]
SpicachlorantinsA,C Chloranthusserratus Chloranthaceae[125]
SpicachlorantinsG–J Chloranthusspicatus Chloranthaceae[136]
Unnamed(17–18) Chloranthusserratus Chloranthaceae[125]
Fig.7 Structuresoflindenaneanditsdisesquiterpenoids 16 and 17,andthe8,9-seco-lindenane disesquiterpenoidchloramultiolG(18)
Plate1 Lindenane disesquiterpenoids
2.1.8Cuparane,Cyclolaurane,andHerbertaneDisesquiterpenoids
Thecuparane,cyclolaurane,andherbertaneskeletonsarerelatedstructurally.Since thesetypesofmonomericsesquiterpenoidsarenotcommon,theirdimerizationhas beenreportedonlyoccasionallyinseveralspeciesofthefamiliesHerbertiaceae, Lejeuneaceae,Mastigophoraceae,Rhodomelaceae,andScrophulariaceae(Table 8, Fig. 8).
Table8 Cuparane,cyclolaurane,andherbertaneDSs
Compound
Structural typeOriginFamilyRefs.
AquaticenolHerbertane (Isocuparane) Lejeuneaaquatica Lejeuneaceae[137]
Aquaticol(19)Cuparane Veronica anagallisaquatica
LaurebiphenylCyclolaurane Laurencianidifica
Scrophulariaceae[138, 139]
Rhodomelaceae[140]
Mastigophorenes A–B Herbertane (Isocuparane) Herbertus sakuraii Herbertaceae[141]
Mastigophorenes A–B Herbertane (Isocuparane) Mastigophora diclados
Mastigophorenes C–D Herbertane (Isocuparane) Mastigophora diclados
Unnamed(20)Cyclolaurane Laurencia microcladia
Unnamed(21)Cyclolaurane Laurencia microcladia
Mastigophoraceae[142, 143]
Mastigophoraceae[143, 144]
Rhodomelaceae[145]
Rhodomelaceae[146]
Fig.8 Structuresofcuparane,cyclolaurane,andherbertane,andtheircorrespondingdisesquiterpenoidsaquaticol(19), 20, 21,andmastigophoreneA(22)
2.1.9MiscellaneousDisesquiterpenoids
Exceptforthestructuralclassesmentionedabove,DSsofothertypescanalsobe foundinanumberoffungi,protozoa,andotherplants(Table 9).Representative DSsandtheircorrespondingsesquiterpenesofeachclassareshowninFigs. 9, 10, 11,and 12.
Table9 MiscellaneousDSs
CompoundStructuraltypeOriginFamilyRefs.
Alertenone(24)Quadrane Alertigorgia sp Agaricaceaea [147]
AurisinsA,KAristolane Neonothopanusnambi, PW1andPW2 Marasmiaceaea [148]
BisacutifolonesA–CPinguisane Porellaacutifolia subsp. tosana Hepaticaeb [149]
Bis-cineradienone (25) Cinerane Cinerariafruticulorum Asteraceae b [150]
Bitaylorione(27)1,10-Secoaromadendrane Myliataylorii Jungermanniaceaeb [151]
Bovistol(31)Illudane Bovista sp 96042Agaricaceae (basidiomycete)a [152]
CinnamacrinC(29)Drimane Cinnamosmamacrocarpa Canellaceaeb [153]
DistentosideDinorpterosin Dennstaedtiadistenta Dennstaedtiaceaeb [154]
MethylmonachosorinB Dinorpterosin Dennstaedtiadistenta Dennstaedtiaceaeb [154]
14-O-Methyl monachosorinA (Monomethyl monachosorinA)
14-O-Methyl monachosorinA (Monomethyl monachosorinA)
Dinorpterosin Dennstaedtiadistenta Dennstaedtiaceaeb [147]
Dinorpterosin Monachosorumhenryi/ Monachosorum flagellare/Monachosorummaximowiczii
Pteridaceaeb [147]
140 -O-MethylmonachosorinA Dinorpterosin Monachosorumflagellare Pteridaceaeb [147]
MonachosorinsA–CDinorpterosin Monachosorumarakii Pteridaceaeb [155, 156]
MonachosorinsA–CDinorpterosin Dennstaedtiadistenta Dennstaedtiaceaeb [155]
MonachosorinsA–CDinorpterosin Monachosorumhenryi/ Monachosorumflagellare/ Monachosorum maximowiczii Pteridaceaeb [155]
MyltaylorionesA–B1,10-Secoaromadendrane Myliataylorii Jungermanniaceaeb [151]
OfficinalicacidDrimane Fomesofficinalis Fomitopsidaceaea [157, 158]
VannusalsA–BHemivannusane Euplotesvannus Euplotidaec [159]
Unnamed(32–33)Norilludalane Stereumostrea
BCC22955 Stereaceaea [160]
aFungi
bPlant cProtozoa
Fig.9 Structuresof pterosin,quadrane, cinerane,andpinguisane, andtheircorresponding disesquiterpenoids 23–26
Fig.10 Structuresof aromadendrane,aristolane, anddrimane,andtheir corresponding disesquiterpenoids 27–29
Fig.11 Structuresofhemivanusane,illudane,cinerane,andilludalane,andtheircorresponding disesquiterpenoids 32 and 33
Fig.12 Sesquiterpenoidstructuraltypesandtheirrepresentativecompounddisesquiterpenoids 34–38
2.1.10CompoundDisesquiterpenoids
Earlierinvestigationsshowedthattheco-occurrenceofdifferentstructuraltypesof sesquiterpenoidsmightalsoleadtotheirdimerization(Table 10 andFigs. 12 and 13). Eudesmane–guaianeor1,10-secoeudesmane–guaianearethemosttypicalcoupling patternsthusfardetected,althoughgermacrane-guaiane,eudesmane-bisabolane, elemane–eudesmane,myliane-1,10-secoaromadendrane,andxanthane–guaianecouplingsmayalsooccurinvariousspeciesofthefamilyAsteraceae.Aguaianearomadendranecouplinghasbeenreportedin Chiloscyphussubporosus fromthe Lophocoleaceaefamily[172].
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If a civil officer should, under the pending amendment, attempt to quell a riot by calling on the bystanders, if they have arms, he is punishable for that. If a marshal, the marshal of the district in which the election occurs, the marshal nominated to the Senate and confirmed by the Senate—I do not mean a deputy marshal—should see an affray or a riot at the polls on election day and call upon the bystanders to quell it, if this bill becomes a law, and one of those bystanders has a revolver in his pocket, or another one takes a stick or a cudgel in his hand, the marshal may be fined $5,000 and punished by five years’ imprisonment.
Such are the devices to belittle national authority and national law, to turn the idea of the sovereignty of the nation into a laughing-stock and a by-word.
Under what pretexts is this uprooting and overturning to be? Any officer who transgresses the law, be he civil or military, may be punished in the courts of the State or in the courts of the nation under existing law. Is the election act unconstitutional? The courts for ten years have been open to that question. The law has been pounded with all the hammers of the lawyers, but it has stood the test; no court has pronounced it unconstitutional, although many men have been prosecuted and convicted under it. Judge Woodruff and Judge Blatchford have vindicated its constitutionality. But, as I said before, the constitutional argument has been abandoned. The supreme political court, practically now above Congresses or even constitutions, the democratic caucus, has decided that the law is constitutional. The record of the judgment is in the legislative bill.
We are told it costs money to enforce the law. Yes, it costs money to enforce all laws; it costs money to prosecute smugglers, counterfeiters, murderers, mail robbers and others. We have been informed that it has cost $200,000 to execute the election act. It cost more than $5,000,000,000 in money alone, to preserve our institutions and our laws, in one war, and the nation which bled and the nation which paid is not likely to give up its institutions and the birthright of its citizens for $200,000. [Applause in the galleries.]
The presiding officer, (Mr. C , in the chair.) The Senator will suspend a moment. The chair will announce to the galleries that there shall be no more applause; if so, the galleries will be cleared immediately.
Mr. C . Mr. President, that interruption reminds me, the present occupant of the chair having been deeply interested in the bill, that the appropriations made and squandered for local and unlawful improvements in the last river and harbor bill alone, would pay for executing the election law as long as grass grows or water runs. The interest on the money wrongfully squandered in that one bill, would execute it twice over perpetually. The cost of this needless extra session, brought about as a partisan contrivance, would execute the election law for a great while. A better way to save the cost, than to repeal the law, is to obey it. Let White Leagues and rifle clubs disband; let your night-riders dismount; let your tissue ballot-box stuffers desist; let repeaters, false-counters, and ruffians no longer be employed to carry elections, and then the cost of executing the law will disappear from the public ledger.
Again we are told that forty-five million people are in danger from an army nominally of twenty-five thousand men scattered over a continent, most of them beyond the frontiers of civilized abode. Military power has become an affrighting specter. Soldiers at the polls are displeasing to a political party. What party? That party whose Administration ordered soldiers, who obeyed, to shoot down and kill unoffending citizens here in the streets of Washington on election day; that party which has arrested and dispersed Legislatures at the point of the bayonet; that party which has employed troops to carry elections to decide that a State should be slave and should not be free; that party which has corraled courts of justice with national bayonets, and hunted panting fugitive slaves, in peaceful communities, with artillery and dragoons; that party which would have to-day no majority in either House of Congress except for elections dominated and decided by violence and fraud; that party under whose sway, in several States, not only the right to vote, but the right to be, is now trampled under foot.
Such is the source of an insulting summons to the Executive to become particeps criminis in prostrating wholesome laws, and this is the condition on which the money of the people, paid by the people, shall be permitted to be used for the purposes for which the people paid it.
Has the present national Administration been officiously robust in checking the encroachments and turbulence of democrats, either by
the use of troops or otherwise? I ask this question because the next election is to occur during the term of the present Administration.
What is the need of revolutionary measures now? What is all this uproar and commotion, this daring venture of partisan experiment, for? Why not make your issue against these laws, and carry your issue to the people? If you can elect a President and a Congress of your thinking, you will have it all your own way.
Why now should there be an attempt to block the wheels of government on the eve of an election at which this whole question is triable before the principals and masters of us all? The answer is inevitable. But one truthful explanation can be made of this daring enterprise. It is a political, a partisan manœuvre. It is a strike for party advantage. With a fair election and an honest count, the democratic party cannot carry the country. These laws, if executed, insure some approach to a fair election. Therefore they stand in the way, and therefore they are to be broken down.
I reflect upon no man’s motives, but I believe that the sentiment which finds expression in the transaction now proceeding in the two houses of Congress, has its origin in the idea I have stated. I believe that the managers and charioteers of the democratic party think that with a fair election and a fair count they cannot carry the State of New York. They know that with free course, such as existed in 1868, to the ballot-box and count, no matter what majority may be given in that State where the green grass grows, the great cities will overbalance and swamp it. They know that with the ability to give eighty, ninety, one hundred thousand majority in the county of New York and the county of Kings, half of it fraudulently added, it is idle for the three million people living above the Highlands of the Hudson to vote.
This is a struggle for power. It is a fight for empire. It is a contrivance to clutch the National Government. That we believe; that I believe.
The nation has tasted, and drunk to the dregs, the sway of the democratic party, organized and dominated by the same influences which dominate it again and still. You want to restore that dominion. We mean to resist you at every step and by every lawful means that opportunity places in our hands. We believe that it is good for the country, good for every man North and South who loves the country
now, that the Government should remain in the hands of those who were never against it. We believe that it is not wise or safe to give over our nationality to the dominion of the forces which formerly and now again rule the democratic party. We do not mean to connive at further conquests, and we tell you that if you gain further political power, you must gain it by fair means, and not by foul. We believe that these laws are wholesome. We believe that they are necessary barriers against wrongs, necessary defenses for rights; and so believing, we will keep and defend them even to the uttermost of lawful honest effort.
The other day, it was Tuesday I think, it pleased the honorable Senator from Illinois [Mr. Davis] to deliver to the Senate an address, I had rather said an opinion, able and carefully prepared. That honorable Senator knows well the regard not only, but the sincere respect in which I hold him, and he will not misunderstand the freedom with which I shall refer to some of his utterances.
Whatever else his sayings fail to prove, they did I think, prove their author, after Mrs. Winslow, the most copious and inexhaustible fountain of soothing syrup. The honorable Senator seemed like one slumbering in a storm and dreaming of a calm. He said there was no uproar anywhere—one would infer you could hear a pin drop—from centre to circumference. Rights, he said, are secure. I have his language here. If I do not seem to give the substance aright I will stop and read it. Rights secure North and South; peace and tranquillity everywhere. The law obeyed and no need of special provisions or anxiety. It was in this strain that the Senator discoursed.
Are rights secure, when fresh-done barbarities show that local government in one portion of our land is no better than despotism tempered by assassination? Rights secure, when such things can be, as stand proved and recorded by committees of the Senate! Rights secure, when the old and the young fly in terror from their homes, and from the graves of their murdered dead! Rights secure, when thousands brave cold, hunger, death, seeking among strangers in a far country a humanity which will remember that—
“Before man made them citizens, Great nature made them men!”
Read the memorial signed by Judge Dillon, by the democratic mayor of Saint Louis, by Mr. Henderson, once a member of the Senate, and by other men known to the nation, detailing what has been done in recent weeks on the Southern Mississippi. Read the affidavits accompanying this memorial. Has any one a copy of the memorial here? I have seen the memorial. I have seen the signatures. I hope the honorable Senator from Illinois will read it, and read the affidavits which accompany it. When he does, he will read one of the most sickening recitals of modern times. He will look upon one of the bloodiest and blackest pictures in the book of recent years. Yet the Senator says, all is quiet. “There is not such faith, no not in Israel.” Verily “order reigns in Warsaw.”
Solitudinem faciunt, pacem appellant.
Mr. President, the republican party every where wants peace and prosperity—peace and prosperity in the South, as much and as sincerely as elsewhere. Disguising the truth, will not bring peace and prosperity. Soft phrases will not bring peace. “Fair words butter no parsnips.” We hear a great deal of loose, flabby talk about “fanning dying embers,” “rekindling smoldering fires,” and so on. Whenever the plain truth is spoken, these unctious monitions, with a Peter Parley benevolence, fall copiously upon us. This lullaby and hush has been in my belief a mistake from the beginning. It has misled the South and misled the North. In Andrew Johnson’s time a convention was worked up at Philadelphia, and men were brought from the North and South, for ecstasy and gush. A man from Massachusetts and a man from South Carolina locked arms and walked into the convention arm in arm, and sensation and credulity palpitated, and clapped their hands, and thought an universal solvent had been found. Serenades were held at which “Dixie” was played. Later on, anniversaries of battles fought in the war of Independence, were made occasions by men from the North and men from the South for emotional, dramatic, hugging ceremonies. General Sherman, I remember, attended one of them, and I remember also, that with the bluntness of a soldier, and the wisdom and hard sense of a statesman, he plainly cautioned all concerned not to be carried away, and not to be fooled. But many have been fooled, and being fooled,
have helped to swell the democratic majorities which now display themselves before the public eye.
Of all such effusive demonstrations I have this to say: honest, serious convictions are not ecstatic or emotional. Grave affairs and lasting purposes do not express or vent themselves in honeyed phrase or sickly sentimentality, rhapsody, or profuse professions.
This is as true of political as of religious duties. The Divine Master tells us, “Not every one that saith unto me, Lord, Lord, shall enter into the kingdom of heaven; but he that doeth the will of my Father which is in heaven.”
Facts are stubborn things, but the better way to deal with them is to look them squarely in the face.
The republican party and the Northern people preach no crusade against the South. I will say nothing of the past beyond a single fact. When the war was over, no man who fought against his flag was punished even by imprisonment. No estate was confiscated. Every man was left free to enjoy life, liberty, and the pursuit of happiness. After the Southern States were restored to their relations in the Union, no man was ever disfranchised by national authority—not one. If this statement is denied, I invite any Senator to correct me. I repeat it. After the Southern State governments were rebuilded, and the States were restored to their relations in the Union, by national authority, not one man for one moment was ever denied the right to vote, or hindered in the right. From the time that Mississippi was restored, there never has been an hour when Jefferson Davis might not vote as freely as the honorable Senator in his State of Illinois. The North, burdened with taxes, draped in mourning, dotted over with new-made graves tenanted by her bravest and her best, sought to inflict no penalty upon those who had stricken her with the greatest, and, as she believed, the guiltiest rebellion that ever crimsoned the annals of the human race.
As an example of generosity and magnanimity, the conduct of the nation in victory was the grandest the world has ever seen. The same spirit prevails now. Yet our ears are larumed with the charge that the republicans of the North seek to revive and intensify the wounds and pangs and passions of the war, and that the southern democrats seek to bury them in oblivion of kind forgetfulness.
We can test the truth of these assertions right before our eyes. Let us test them. Twenty-seven States adhered to the Union in the dark hour. Those States send to Congress two hundred and sixty-nine Senators and Representatives. Of these two hundred and sixty-nine Senators and Representatives, fifty-four, and only fifty-four, were soldiers in the armies of the Union. The eleven States which were disloyal send ninety-three Senators and Representatives to Congress. Of these, eighty-five were soldiers in the armies of the rebellion, and at least three more held high civil station in the rebellion, making in all eighty-eight out of ninety-three.
Let me state the same fact, dividing the Houses. There are but four Senators here who fought in the Union Army. They all sit here now; and there are but four. Twenty Senators sit here who fought in the army of the rebellion, and three more Senators sit here who held high civil command in the confederacy.
In the House, there are fifty Union soldiers from twenty-seven States, and sixty-five confederate soldiers from eleven States.
Who, I ask you, Senators, tried by this record, is keeping up party divisions on the issues and hatreds of the war?
The South is solid. Throughout all its borders it has no seat here save two in which a republican sits. The Senator from Mississippi [M . B ] and the Senator from Louisiana [Mr. K ] are still spared; and whisper says that an enterprise is afoot to deprive one of these Senators of his seat. The South is emphatically solid. Can you wonder that the North soon becomes solid too? Do you not see that the doings witnessed now in Congress fill the North with alarm, and distrust of the patriotism and good faith of men from the South? Forty-two democrats have seats on this floor; forty-three if you add the honorable Senator from Illinois, [M . D .] He does not belong to the democratic party, although I must say, after reading his speech the other day, that a democrat who asks anything more of him is an insatiate monster. [Laughter.] If we count the Senator from Illinois, there are forty-three democrats in this Chamber. Twenty-three is a clear majority of all, and twenty-three happens to be exactly the number of Senators from the South who were leaders in the late rebellion.
Do you anticipate my object in stating these numbers? For fear you do not, let me explain. Forty-two Senators rule the Senate; twenty-
three Senators rule the caucus. A majority rules the Senate; a caucus rules the majority; and the twenty-three southern Senators rule the caucus. The same thing, in the same way, governed by the same elements, is true in the House.
This present assault upon the purity and fairness of elections, upon the Constitution, upon the executive department, and upon the rights of the people; not the rights of a king, not on such rights as we heard the distinguished presiding officer, who I am glad now to discover in his seat, dilate upon of a morning some weeks ago; not the divine right of kings, but the inborn rights of the people—the present assault upon them, could never have been inaugurated without the action of the twenty-three southern Senators here, and the southern Representatives there, [pointing to the House.]
The people of the North know this and see it. They see the lead and control of the democratic party again where it was before the war, in the hands of the South. “By their fruits ye shall know them.” The honorable Senator from Alabama [Mr. M ], educated no doubt by experience in political appearances, and spectacular effects, said the other day that he preferred the democrats from the North should go first in this debate. I admired his sagacity. It was the skill of an experienced tactician to deploy the northern levies as the sappers and miners; it was very becoming certainly. It was not from cruelty, or to make them food for powder, that he set them in the forefront of the battle; he thought it would appear better for the northern auxiliaries to go first and tunnel the citadel. Good, excellent, as far as it went; but it did not go very far in misleading anybody; putting the tail foremost and the head in the sand, only displayed the species and habits of the bird. [Laughter.]
We heard the other day that “the logic of events” had filled the southern seats here with men banded together by a common history and a common purpose. The Senator who made that sage observation perhaps builded better than he knew. The same logic of events, let me tell democratic Senators, and the communities behind them, is destined to bring from the North more united delegations.
I read in a newspaper that it was proposed the other day in another place, to restore to the Army of the United States men who, educated at the nation’s cost and presented with the nation’s sword, drew the sword against the nation’s life. In the pending bill is a
provision for the retirement of officers now in the Army, with advanced rank and exaggerated pay. This may be harmless, it may be kind. One swallow proves not spring, but along with other things, suspicion will see in it an attempt to coax officers now in the Army to dismount, to empty their saddles, in order that others may get on.
So hue and cry is raised because courts, on motion, for cause shown in open court, have a right to purge juries in certain cases. No man in all the South, under thirty-five years of age, can be affected by this provision, because every such man was too young when the armies of the rebellion were recruited to be subject to the provision complained of. As to the rest, the discretion is a wholesome one. But, even if it were not, let me say in all kindness to southern Senators, it was not wise to make it a part of this proceeding, and raise this uproar in regard to it.
Even the purpose, in part already executed, to remove the old and faithful officers of the Senate, even Union soldiers, that their places may be snatched by others—to overturn an order of the Senate which has existed for a quarter of a century, in order to grasp all the petty places here, seems to me unwise. It is not wise, if you want to disarm suspicion that you mean aggrandizing, gormandizing, unreasonable things.
Viewing all these doings in the light of party advantage—advantage to the party to which I belong, I could not deplore them; far from it; but wishing the repose of the country, and the real, lasting, ultimate welfare of the South, and wishing it from the bottom of my heart, I believe they are flagrantly unwise, hurtfully injudicious.
What the South needs is to heal, build, mend, plant, sow. In short, to go to work. Invite labor; cherish it; do not drive it out. Quit proscription, both for opinion’s sake, and for color’s sake. Reform it altogether. I know there are difficulties in the way. I know there is natural repugnance in the way; but drop passion, drop sentiment which signifies naught, and let the material prosperity and civilization of your land advance. Do not give so much energy, so much restless, sleepless activity, to an attempt so soon to get possession once more, and dominate and rule the country. There is room enough at the national board, and it is not needed, it is not decorous, plainly speaking, that the South should be the MacGregor
at the table, and that the head of the table should be wherever he sits. For a good many reasons, it is not worth while to insist upon it.
Mr. President, one of Rome’s famous legends stands in these words: “Let what each man thinks of the Republic be written on his brow.” I have spoken in the spirit of this injunction. Meaning offence to no man, and holding ill-will to no man, because he comes from the South, or because he differs with me in political opinion, I have spoken frankly, but with malice toward none.
This session, and the bill pending, are acts in a partisan and political enterprise. This debate, begun after a caucus had defined and clenched the position of every man in the majority, has not been waged to convince anybody here. It has resounded to fire the democratic heart, to sound a blast to the cohorts of party, to beat the long-roll, and set the squadrons in the field. That is its object, as plainly to be seen as the ultimate object of the attempted overthrow of laws.
Political speeches having been thus ordained, I have discussed political themes, and with ill-will to no portion of the country but good will toward every portion of it, I have with candor spoken somewhat of my thoughts of the duties and dangers of the hour. [Applause on the floor and in the galleries.]
Speech of Hon. John M. Broomall, of Pennsylvania,
On the Civil Rights Bill. House of Representatives, March 8, 1866.
Mr. Speaker, it is alleged that this species of legislation will widen the breach existing between the two sections of the country, will offend our southern brethren. Do not gentlemen know that those who are most earnestly asking this legislation are our southern brethren themselves.
They are imploring us to protect them against the conquered enemies of the country, who notwithstanding their surrender, have managed, through their skill or our weakness, to seize nearly all the conquered territory.
This is not the first instance in the world’s history in which all that had been gained by hard fighting was lost by bad diplomacy.
But they, whose feelings are entitled to so much consideration in the estimation of those who urge this argument, are not our southern brethren, but the southern brethren of our political opponents; the conquered rebels, pardoned and unpardoned; traitors priding themselves upon their treason.
These people are fastidious. The ordinary terms of the English language must be perverted to suit their tastes. Though they surrendered in open and public war, they are not to be treated as prisoners. Though beaten in the last ditch of the last fortification, they are not to be called a conquered people. The decision of the forum of their own choosing is to be explained away into meaningless formality for their benefit. Though guilty of treason, murder, arson, and all the crimes in the calendar, they are “our southern brethren.” The entire decalogue must be suspended lest it should offend these polished candidates for the contempt and execration of posterity.
Out of deference to the feelings of these sensitive gentlemen, an executive construction must be given to the word “loyalty,” so that it shall embrace men who only are not hanged because they have been pardoned, and who only did not destroy the Government because they could not. Out of deference to the feelings of these sensitive gentlemen, too, a distinguished public functionary, once the champion of the rights of man, a leader in the cause of human progress, a statesman whose keen foreknowledge could point out the “irrepressible conflict between slavery and freedom,” cannot now see that treason and loyalty are uncompromising antagonisms.
It is charged against us that the wheels of Government are stopped by our refusal to admit the representatives of these southern communities. When we complain that Europe is underselling us in our markets, and demand protection for the American laborer, we are told to “admit the southern Senators and Representatives.” When we complain that excessive importations are impoverishing the country, and rapidly bringing on financial ruin, we are told to “admit the southern Senators and Representatives.” When we complain that an inflated currency is making the rich richer, and the poor poorer, keeping the prices of even the necessaries of life beyond the reach of widows and orphans who are living upon fixed incomes, the stereotyped answer comes, “Admit the southern Senators and Representatives.” When we demand a tax upon cotton to defray the enormous outlay made in dethroning that usurping “king of the world,” still the answer comes, and the executive parrots everywhere repeat it, “Admit the southern Senators and Representatives.”
The mind of the man who can see in that prescription a remedy for all political and social diseases must be curiously constituted. Would these Senators and Representatives vote a tax upon cotton? Would they protect American industry by increasing duties? Would they prevent excessive importations? To believe this requires as unquestioning a faith as to believe in the sudden conversion of whole communities from treason to loyalty.
We are blocking the wheels of Government! Why, the Government has managed to get along for four years, not only without the aid of the Southern Senators and Representatives, but against their efforts to destroy it; and in the mean time has crushed a rebellion that would have destroyed any other Government under heaven. Surely
the nation can do without the services of these men, at least during the time required to examine their claims and to protect by appropriate legislation our Southern brethren. None but a Democrat would think of consulting the wolf about what safeguard should be thrown around the flock.
Those who advocate the admission of the Senators and Representatives from the States lately reclaimed from the rebellion, as a means of protecting the loyal men in those States and as a substitute for the system of legislation of which this bill is part, well know that the majority in both Houses of Congress ardently desire the full recognition of those States, and only ask that the rights and interests of the truly loyal men in those States shall be first satisfactorily secured.
Much useless controversy has been had about the legal status of those States. There is no difference between the two parties of the country on that point. The actual point of difference is this: the Democrats affiliate with their old political friends in the South, the late rebels, the friends and followers of Breckinridge, Lee, and Davis. The Union majority, on the other hand, naturally affiliate with the loyal men in the South, the men who have always supported the Government against Breckinridge, Lee, and Davis. Each party wants the South reconstructed in the hands of its own “southern brethren.”
In short, the northern party corresponding with the loyal men of the South ask that the legitimate results of Grant’s victory shall be carried out, while the northern party corresponding with the rebels of the South ask that things should be considered as if Lee had been the conqueror, or at least as if there had been a drawn battle, without victory on either side.
This brings the rights of those in whose behalf the opponents of the bill under consideration are acting directly in question, and in order to limit down the field of controversy as far as possible, let us inquire how far all parties agree upon the legal status of the communities lately in rebellion. Now, the meanest of all controversies is that which comes from dialectics. Where the disputants attach different meanings to the same word their time is worse than thrown away. I have always looked upon the question whether the States are in or out of the Union as only worthy of the schoolmen of the middle ages, who could write volumes upon a mere
verbal quibble. The disputants would agree if they were compelled to use the word “State” in the same sense. I will endeavor to avoid this trifling.
All parties agree that at the close of the rebellion the people of North Carolina, for example, had been “deprived of all civil government.” The President, in his proclamation of May 29, 1865, tells the people of North Carolina this in so many words, and he tells the people of the other rebel States the same thing in his several proclamations to them. This includes the Conservatives and Democrats, who, however they may disagree, at last agree in this, that the President shall do their thinking.
The Republicans subscribe to this doctrine, though they differ in their modes of expressing it. Some say that those States have ceased to possess any of the rights and powers of government as States of the Union. Others say, with the late lamented President, that “those States are out of practical relations with the Government.”
Others hold that the State organizations are out of the Union. And still others that the rebels are conquered, and therefore that their organizations are at the will of the conqueror.
The President has hit upon a mode of expression which embraces concisely all these ideas. He says that the people of those States were, by the progress of the rebellion and by its termination, “deprived of all civil government.”
One step further. All parties agree that the people of these States, being thus disorganized for all State purposes, are still at the election of the government, citizens of the United States, and as such, as far as they have not been disqualified by treason, ought to be allowed to form their own State governments, subject to the requirements of the Constitution of the United States.
Still one step further. All parties agree that this cannot be done by mere unauthorized congregations of the people, but that the time, place and manner must be prescribed by some department of the Government, according to the argument of Mr. Webster and the spirit of the decision of the Supreme Court in Luther vs. Borden, 7 Howard, page 1.
Yet another step in the series of propositions. All parties agree that as Congress was not in session at the close of the rebellion, the
President, as Commander-in-Chief, was bound to take possession of the conquered country and establish such government as was necessary.
Thus far all is harmonious; but now the divergence begins. At the commencement of the present session of Congress three-fourths of both Houses held that when the people of the States are “deprived of all civil government,” and when, therefore, it becomes necessary to prescribe the time, place, and manner in and by which they shall organize themselves again into States while the President may take temporary measures, yet only the law-making power of the Government is competent to the full accomplishment of the task. In other words, that only Congress can enable citizens of the United States to create States. I have said that at the commencement of the session three-fourths of both houses held this opinion. The proportion is smaller now, and by a judicious use of executive patronage it may become still smaller; but the truth of the proposition will not be affected if every Representative and Senator should be manipulated into denying it.
On the other hand, the remaining fourth, composed of the supple Democracy and its accessions, maintain that this State-creating power is vested in the President alone, and that he has already exercised it.
The holy horror with which our opponents affect to contemplate the doctrine of destruction of States is that much political hypocrisy. Every man who asks the recognition of the existing local governments in the South thereby commits himself to that doctrine. The only possible claim that can be set up in favor of the existing governments is based upon the theory that the old ones have been destroyed. The present organizations sprang up at the bidding of the President after the conquest among a people who, he said, had been “deprived of all civil government.”
If the President’s “experiment” had resulted in organizing the southern communities in loyal hands, the majority in Congress would have found no difficulty in indorsing it and giving it the necessary efficiency by legislative enactment.
In this case, too, the President never would have denied the power of Congress in the premises. He never would have set up the theory that the citizens of the United States, through their representatives,
are not to be consulted when those who have once broken faith with them ask to have the compact renewed.
Our opponents have no love for the President. They called him a usurper and a tyrant in Tennessee. They ridiculed him as a negro “Moses.” They tried to kill him, and failing that, they accused him of being privy to the murder of his predecessor. But when his “experiment” at reconstruction was found to result in favor of their friends, the rebels, then they hung themselves about his neck like so many mill-stones, and tried to damn him to eternal infamy by indorsing his policy. Will they succeed? Will he shake them off, or go down with them?
But let us suffer these discordant elements to settle their own terms of combinations as best they may. The final result cannot be doubtful.
If ten righteous men were needed to save Sodom, even Andrew Johnson will find it impossible to save the Democratic party.
Our path of duty is plain before us. Let us pass this bill and such others as may be necessary to secure protection to the loyal men of the South. If our political opponents thwart our purposes in this, let us go to the country upon that issue.
I am by no means an advocate of extensive punishment, either in the way of hanging or confiscation, though some of both might be salutary. I do not ask that full retribution be enforced against those who have so grievously sinned. I am willing to make forgiveness the rule and punishment the exception; yet I have my ultimatum. I might excuse the pardon of the traitors Lee and Davis, even after the hanging of Wirz, who but obeyed their orders, orders which he would have been shot for disobeying. I might excuse the sparing of the master after killing the dog whose bite but carried with it the venom engendered in the master’s soul. I might look calmly upon a constituency ground down by taxation, and tell the complainants that they have neither remedy nor hope of vengeance upon the authors of their wrongs. I might agree to turn unpityingly from the mother whose son fell in the Wilderness, and the widow whose husband was starved at Andersonville, and tell them that in the nature of things retributive justice is denied them, and that the murderers of their kindred may yet sit in the councils of their country; yet even I have my ultimatum. I might consent that the
glorious deeds of the last five years should be blotted from the country’s history; that the trophies won on a hundred battle-fields, the sublime visible evidence of the heroic devotion of America’s citizen soldiery, should be burned on the altar of reconciliation. I might consent that the cemetery at Gettysburg should be razed to the ground; that its soil should be submitted to the plow, and that the lamentation of the bereaved should give place to the lowing of cattle. But there is a point beyond which I shall neither be forced nor persuaded. I will never consent that the government shall desert its allies in the South and surrender their rights and interests to the enemy, and in this I will make no distinction of caste or color either among friends or foes.
The people of the South were not all traitors. Among them were knees that never bowed to the Baal of secession, lips that never kissed his image. Among the fastness of the mountains, in the rural districts, far from the contagion of political centres, the fires of patriotism still burned, sometimes in the higher walks of life, oftener in obscure hamlets, and still oftener under skins as black as the hearts of those who claimed to own them.
These people devoted all they had to their country. The homes of some have been confiscated, and they are now fugitives from the scenes that gladdened their childhood. Some were cast into dungeons for refusing to fire upon their country’s flag, and still others bear the marks of stripes inflicted for giving bread and water to the weary soldier of the Republic, and aiding the fugitive to escape the penalty of the disloyalty to treason. If the God of nations listened to the prayers that ascended from so many altars during those eventful years, it was to the prayers of these people.
Sir, we talked of patriotism in our happy northern homes, and claimed credit for the part we acted; but if the history of these people shall ever be written, it will make us blush that we ever professed to love our country.
The government now stands guard over the lives and fortunes of these people. They are imploring us not to yield them up without condition to those into whose hands recent events have committed the destinies of the unfortunate South. A nation which could thus withdraw its protection from such allies, at such a time, without their
full and free consent, could neither hope for the approval of mankind nor the blessing of heaven.
Speech,
of Hon. Charles A. Eldridge, of Wisconsin.
Against the Civil Rights Bill, in the House of Representatives, March 2, 1866.
Mr. Speaker: I thought yesterday that I would discuss this measure at some length; but I find myself this morning very unwell; and I shall therefore make only a few remarks, suggesting some objections to the bill.
I look upon the bill before us, Mr. Speaker, as one of the series of measures rising out of a feeling of distrust and hatred on the part of certain individuals, not only in this House, but throughout the country, toward these persons who formerly held slaves. I had hoped that long before this time the people of this country would have come to the conclusion that the subject of slavery and the questions connected with it had already sufficiently agitated this country. I had hoped that now, when the war is over, when peace has been restored, when in every State of the Union the institution of slavery has been freely given up, its abolition acquiesced in, and the Constitution of the United States amended in accordance with that idea, this subject would cease to haunt us as it is made to do in the various measures which are constantly being here introduced.
This bill is, it appears to me, one of the most insidious and dangerous of the various measures which have been directed against the interest of the people of this country. It is another of the measures designed to take away the essential rights of the State. I know that when I speak of States and State rights, I enter upon unpopular subjects. But, sir, whatever other gentlemen may think, I hold that the rights of the States are the rights of the Union, that the rights of the States and the liberty of the States are essential to the liberty of the individual citizen. * * *
