全 文 ：·966· 中草焉ChineseTraditionalandHerbalDrugs第37卷第7期2006年7月
化学成分
CaffeoylquinicacidderivativesfromB
antihistaminereleasectivites
WANGJue2，WANGNai—li¨，YAoXin—shen91，KITANGAKASusumu2
(1．DepartmentofNaturalProductsChemistry，ShenyangP armaceuticalUniversity，Shenyang110016，China；2．Depart—
mentofPharmacognosy，CollegeofPharmacy，NihonUn versity，7-7—1Narashinodai，Funabashi，Chiba274—8555，Jap n)
Abstract：ObjectiveBasedontheactivitiesofantihistaminereleasetostudythecompoundsfrom
Bidensparvi—floraandfindbiologicala tivecompounds．MethodsThec emicalconstituentsfromB．
parviflorawe eisolatedbysilicagelandSphadexLH—-20columnchromatographiesandpur fiedbyprepar—-
ativeHPLC．Thechemicalstructureshadbeenidentifiedbyphysiochemicalpropertiesandspectroscopic
methods．ResultsSixcaffeoylquinicacidderivativeswereidentifiedas3，5一di—O—caffeoylquinicacid(I)，
3，4一di—O—caffeoylquinicacid(I)，4，5一di—O—caffeoylquinicacid(Ⅲ)，4一O—caffeoylquinicacid(Ⅳ)，5一O—
caffeoylquinicac d(V)，4一[3一(3，4-dihydroxy—phenyl)-acryloyloxy]-z，3-dihydroxy一2一methyl—butyric
acid(VI)．ConclusionCompou dsI一ⅥarefirstobtainedfromB．parvifloraandVliSnewone．Some
ofthecompoundsexhibittheactivitiesinantiallergicassays．Moreover，thestructure—actiVityrelat on—
shipsofthesecompoundshavebeenalsodiscussedinthispaper．
Keywords：BidensparvifloraWilld．；caffeoylquinica id；anti-histaminerelease
小花鬼针草中咖啡酰奎宁酸类成分及其抑制组胺释放活性
王珏2，王乃利¨，姚新生1，北中退2
(1．沈阳药科大学天然药化教研室，辽宁沈阳 110016；2．日本大学药学部生药学研究室，千叶船桥274—8555日本)
摘 要：目的研究小花鬼针草Bidensparviflora全株的化学成分，并通过抑制组胺释放活性方法寻找生物活性
化合物。方法采用硅胶、SephadexLH一20和ODS柱色谱分离化合物，运用1DNMR，2DNMR等波谱法鉴定了化
学结构，通过组胺抑制实验探讨抗炎活性。结果 分离鉴定6种咖啡酰奎宁酸类化合物及其甲醇，分别是3，5一二氧
咖啡酰奎宁酸(3，5一di—O—caffeoylquinicacid，I)、3，4-二氧咖啡酰奎宁酸(3，4一di—O—caffeoylquinicacid，I)、4，5-二
氧咖啡酰奎宁酸(4，5一di—O—caffeoylquinicacid，il)、4-氧一咖啡酰奎宁酸(4—0一caffeoylquinicacid，Ⅳ)、5-氧一咖啡酰
奎宁酸(5一O—caffeoylquinicacid，V)、4-[3一(3，4-二羟基苯基)一丙烯酰氧基]一2，3一二羟基一2一甲基一丁酸{4一[3一(3，4一
dihydroxy—phenyl)一acryloyloxy]一2，3-dihydroxy一2一methyl—butyricacid，VI)。结论所有化合物均为首次从该植物
中分得，化合物Ⅵ为新化合物。这些化合物显示一定的抑制组织胺释放活性。
关键词：小花鬼针草；咖啡酰奎宁酸；组胺抑制活性
中圈分类号：R284．1 文献标识码：A 文章编号：0253—2670(2006)07—0966—05
InourscreeningofbioactivityonCompositae
plants，the60％EtOHextractsofBidensparvi—
floraWilld．havebeenshowntohavehigherac-
tivitiesagainsthistaminerel asefromratmast
cellsinducedbyCompound48／80．Forthepurpose
ofhindingbiologicalactivecompounds，thechemi—
calconstituentsofthisplanthavebeenfurtherstu—
died．Duringourpreviousstudies，fivepolyacety—
leneglucosides[1。，threesucroscoumaroylesters，
andoneneolignan，whichwerethoughttocon—
tributetotheinhibitionofhistaminerel ase，have
beenreported[引．Inthispaperthesixcaffeoyl
quinicacidderivativeswereidentifiedas3，5一di—O—
caffeoylquinicac d(I)，3，4一di—O—caffeoylquinic
acid(I)，4，5一di—o—caffeoylquinicacid(I)，4一O—
caffeoylquinicac d(IV)，5一O—caffeoylquinicacid
收稿日期：2005—12—12
*通讯作者王乃利Tel：(0755)26957860E—mail：wangnl@sz．tsinghua．edu．cn
万方数据
中草焉ChineseTraditionalandHerbalDrugs第37卷第7期2006年7,El·967·
(V)，4一E3一(3，4-dihydroxy—phenyl)一acryloyloxy]一
2．3-dihydroxy一2一methyl—butyricacid(Ⅵ)which
werefirstisolatedfromthewholeplantofB．
parvifloFa．Theirstructureswereesbablishedon
thebasisofspectrald ta(UV，FAB—MS，1H—
NMR，13C—NMR，andNOE)．Thefurtherbiologi—
caltestassessedtheirantiallergicactivitiesondif—
ferentmodels．includinginhibitiononnitricoxide
(No)productioninLPSandIFN一7activated
murinemacrophages(RAW264．7)，histaminere—
leasefromratmastcellstimulatedbyantigen-anti—
bodyreactionandreductionof2，2-diphenyl—p
picrylhydrazyl(DPPH)radical．
1 Apparatusndmaterials
Plantmaterials：ThewholplantofB．parvi-
florawascollecteda Da—Hei—ShanCountryof
LiaoningProvinceinChina，inJuly，1999andwas
identifiedbyProf．WeichunWu(Departmentof
MedicinalPl nts，ShenyangPharmaceuticalUni—
versity，China)．Avoucherspecimenisdeposited
intheDepartmentofNaturalProductsChemistry
ofShenyangPlarmaceuticalUniversity．
2 Extractionandisolation
Theair—driedwholeplant(5．5kg)wasex—
tractedwicewith60％ethan01(teneach)under
refluxfor1h．Theextractwasdissolvedandparti—
tionedwithhexane，ethylacetate，and，z—butanol，
respectively，thenthebuta olphaseunderreduced
pressurebelow40℃，yieldedbutanolextract(176
g)．Thecrudefractionsweretestedforanti—his—
taminereleasectivity．The。r／-butanolextractw s
subjectedtosilicagelcolumnchromatography
(Si02，500g，elutedwithCHCl3andMeOHinin—
creasingpolaritytoobtain12frs．Thefr．7(2．45
g)wasppliedtoaSphadexLH-20columneluted
with50％MeOHtoobtainfrs．3—6andwaspurl—
fledbypreparativeHPLC(Sunshupark，PE—
GASILODS，25％Me0H)togivecompounds24
mgofI，45mgofI，16mgofⅢ，18mgof1V，
20mgofV，and13mgofV1．Theextractionand
isolationofB．parviflorawerefini—shedin1999at
CollegeofPharmacy，NihonUniversity．
3 Antiallergicassays
3．1 ReductionofDPPHradical：Reductionof
radicalw sdeterminedaccordingtoCavin．etal[引．
Themixturecontained0．3mLof1．0mmol／L
DPPHredicalso ution，2．4mLof99％ethanol，
and0．3mLofsamplesolution．Thesolutionwas
rapidlymixedandthescavengingcapacitywas
measuredelectrophotometricallybymonitoring，
thedecreaseinabsorbanceat517nmwasdeter—
minedafter10minandthescavengingactivitywas
calculatedspercentageofthradicalreduction．
Quercetin3一O—glucosidewasusedasfl reference
compound．
3．2 Inhibitoryactivityonhistaminerel ase：All
isolatedcompoundswerea sayedusingtheHPLC—
fluorometrythodaspreviouslydescribedwith
modifications[4．引．MaleWistarr ts(JapanSLC．
Shizuoka)weighting180—200gwereexsanguinat—
edandipinjectedwith10mLofTyrodesolution．
Theabdominalregionwasgentlymassagedfor3
minandthentheperitonealexudatewascollected．
Theperitonealcavityfluidcontainingmastcells
wassuspendedin phosphate—bufferedsaline
(PBS)，thenlayeredonBSA(d=1．068)inatest
tubeatroomtemperaturefor20min．Aftercen—
trifugation300Xgand4℃for10min，thelay—
ercontainingmastceilswaspipettedout．Thecells
werewashedthreetimeswith3mLofPBS(pH
7．0)andsuspendedinthemedium．Cellviability
wasdeterminedusingtrypanblue．Mastcells
(1．0×106cells／mL)werepre—incubatedwi htest
samples(10ttL)at37℃for10min，followedby
additionofhistaminerel asers，eitherCompound
48／80(5tLg／mL)oranti—DNP—IgE(5t比g／mL)and
phosphatidylserine(100tlg／mL)．Themixtures
wereincubatedgainfor10min，thequantityof
histaminerel asedwasexpressedinpeakheight
andinhibitorype centagew scalculated．
3．3 InhibitoryeffectonNOproductionbyacti—
vatedmacrophages[6。：Thecellswerseededat
1．2×106cells／mLontoa35mmPetrid shandin—
cubatedat37℃for2 h．Then，testcompounds
wereaddedtotheculturesimultaneouslywithboth
100ng／mLLPSand10U／mLINF-7，andtheceils
wereincubated37℃usuallyfor8h．Afterin—
cubation。thecellsw rechilledonice，scraped
万方数据
·968· 中草菊ChineseTraditionalandHerbalDrugs第37卷第7期2006年7月
fromthedishwithaeellscraper。collectedina mi—
crofugetubeandthenimmediatelycentrifugedat
7000r／minat4C．A7000弘Lvolumeofthesu—
pernatantw splacedina newmicro—fugetube
storedat4Cbeforeassayingfornitrite(N02一)．
ThecellswerewashedtwicewithPBSwithoutdi—
valentcationsbyrepeatedcentrifugationat7000
r／min．Thefinaleellp etwasextractedwith40
‘C ofalysisbuffer，comprising1％Tr tonX一100，
0．1mmol／LDETA，and1％Aprotinin(Sigma)in
20mmol／LHEPESNaOHbuffer，pH7．5，at4。C
for30min．Thecell ysatewascentrifugedat
10000r／minat4。Cfor1min，and30肚Lofthe
resultantsupernatantwasplacedina newmi—
crofugetube．Thefinalcellextractwastoredat
一80Cuntiluse．
4 Resultsandiscussion
Thextractionandseparationwerecarriedout
asdescribednthexperimentals ction．
CompoundI：yellowoil，[a]分一287．6。
(c一0．50，MeOH)，UVA牌Hnm(19￡)：332
(4．656)，286sh，245(4．383)．IR嗡KB。r(cm一1)：
3386，1689，1600，1521，1446，1274，1170，
1 116．FAB—MSm／z：531[M+H]+，163(100)；
HR—FAB—MSfound531．33467， calcdfor
C26H2，012(EM+H]+531．48017)．From1H—NMR
spectra(Table1)，quinicacidmoietywasobserved
between艿4—5．5．Ofthedoubledoubletsignals，
thesignalthatappearedatthelowestfrequencyre—
gionwasassignedtoH一4(艿3．97)，whichwas
bondedtothesp3carbonthatwasalsoconnectedto
ahydroxylgroup．Theot rtwosignalsppeared
atananalogousfrequencyregionbecauseH一3and
H一5hadifferentstereochemicalconfiguration(ax
oreq)givenbythechiralityofI，theywereable
tobedistingushedbyt ircouplingpatterns．The
broadsignaldueto1，2-axialcouplingwasas—
signedtoH一30(占5．43)andtheothersignalwith—
outaxialcouplingwasassignedtoH一5(艿5．39)·
Thelocationofcaffeoylsubstitutionon hequinic
acidmoietywasdeducedfromtheHMBC(Table1
and2)，thusindicatingesterificationatC一3andC一
5c7引．Meanwhile．thefu lassignmentsofallsig—
nalsinthe”C—NMRspectrumwereperformedby
2DNMRspectroscopyandcompound1 wascon—
firmedas3，5-O—dicaffeoylquinicacids．
CompoundⅡ：yellowoil，[a]分一297．1。
(c=0．50，MeOH)，UV糊Hnm(19e)：334
(4．629)，286sh，245(4．353)．1^T．y。KB。r(cm一1)：
3386，1692，1600，1521，1446，170，1116．
FAB-MSm／z：531[M+H]+，163(100)；HR—
FAB—MSfound531．33306，calcdforC26H27012
([M+H]+531．48017)．TheprotonsH一3andH一4
wereshifteddownfieldataboutd5．63and5．12，
respectively，thusindicatinge terificationatC一3
andC一4．CompoundⅡwasidentifieds3，4一di—O—
caffeylquinicac dby1H—NMRand13C—NMRdata
(Table1and2)．
CompoundⅢ：yellowoil，[0c]分一252．9。
(c一0．52，MeOH)，UV糌Hnm(19e)：332
(4．650)，286sh，245(4．378)．IR蜷。B。r(cm-1)：
3386，1692，1600，1521，1446，1274，l170，
1 096．FAB—MSm／z：531[M+H]+，163(100)；
HR—FAB—MSfound531．35607，calcdforC26H27012
(EM+H]+531．48017)．From1H—NMRspectra
(Table1)，twocaffeoylresiduesesterifiedatposi—
tionC．．4andC．．5ofquinicacidwerededuced．The
protonsH．．4andH．．5wereshifteddownfieldat
about艿5．04and5．61，respectively，thusindica —
ingesterifieationatC一4a dC一5．Furtherevidence
for4。5一di—O—caffeoylquinicacid[8]wasprovidedby
its13C—NMRspectra(Table2)．
CompoundN：yellowoil，[a]分一318。
(c一0．15，MeOH)，UV煳Hnm(19e)：328
(4．56)，265(3．95)，218(4．46)．IR蜷塞(cm-1)：
3 376，1686，l624，1526，1450，1289，1260，
1169．FAB—MSm／z：355EM+H]+，HR—FAB—
MSfound355．18681，calcdforC16H1909
355．31022([M+H3+)．From1H—NMRspectra
(Table1)，onecaffeoylresidueesterifiedatposi—
tionC一4ofquinicacidwasdeduced．TheprotonH一
4washifteddownfieldatabout艿5．12，thusindi—
catingesterificationatC一4．Furtherevidencefor4-
O—caffeoylquinicacidwasprovidedbyits”C—NMR
spectra(Table2)．
万方数据
中草菊 ChineseTraditionalandHerbalDrugs第37卷第7期2006年7月·969·
a—assignedby1H—HCOSY，HMQC，andHMBCspectrab-500MHz，TMSasinternalstandard，(inMeOHd4)
Table2”C—NMRDataofdicaffeoyIquinic3376，1685，1619，1526，1450，1289，1260，
acidderivatives 1 l69．FAB—MSm／z：355[M+H]+，HR—FAB—
a—assignedby1H1HCOSY，HMQC，andHMBCspectra．
b一500MHz，TMSasinternalstandard，(inMeOH—d4)
CompoundV：yellowoil，[0【]分一228。
(c一0．25，MeOH)，UVA艘H(nm)(19￡)：326
(4．36)，264(3．75)，218(4．46)．IR艘(cm。1)：
MSfound355．27678，calcdforCl6Hl909
355．31022(rM+H]+)．From1H—NMRspectra
(Table1)，onecaffeoylresidueesterifiedatposi—
tionC一3ofquinicacidwasdeduced．TheprotonH一
3washifteddownfieldatabout艿5．55，thusindi—
catingesterificationatC一5．Furtherevidencefor5一
O—caffeoylquinicacidwasprovidedbyits13C—NMR
spectra(Table2)．
CompoundVI：yellowoil，[0t]分一569。
(c一0．12，MeOH)，UVA篡璺Hnm(19e)：327
(4．05)，266(3．47)，204(3．95)．IRv艘(cm-1)：
3404，2956，1734，1697，163l，1602，1522，
1 450．EI—MS,n／z：326[M]+；HR—FAB—MS
found312．26015，calcdforC14H1708([M]+)
312．2679．1H—NMR(CD。0D，TMS)艿：4．03
(1H，d，J一6．1Hz，H一3)，4．43(1H，t，J一6．1
Hz，H一4ex)，4．14(1H，t，J一6．1Hz H一4ax)．
StructureiSse ninFig．1．
oH rY加H
Hooc、、／＼／—＼。，，t≮v7J、L、夕上、、oH
H，C。’I
。0H 0
Fig．1StructureofcompoundⅥ
The13C—NMRandDEPTspectraof VI dis—
playedfivecarbonsignalswhichomprisedofone
万方数据
·970· 中草115ChineseTraditionalandHerbalDrugs第37卷第7期2006年7月
carboxyliccarbonorester(3c178．4)，anoxygen-
bearingmethane(8c74．5)，anoxygen—bearing
quaternaryc bon(艿c76．8)，onexymethylene
(炙66．1)，andonemethylgroup(3c23．2)．From
1H—NMRandCOSYexperiments，H一4(霸4．43)，
H一4(“4．14)andH一3(晶4．03)showedan
AMX—system，whichsuggestedt atC一3(3c74．5)
wasconnectedtoC一4(潞66．1)．ThecarbonsC一1
(艿c178．4)，C一3(艿c74．6)，andC一5(艿c23．2)
werealllinkedtoC一2(8c76．8)，andH一3(“
4．03)，H一5(艿H1．45)aswellasbetweenC一5(炙
23．2)andH一3(3H4．03)intheHMBCexperiment
reconfirmedtheelucidationofⅥ．Thus．com—
poundⅥwasestablisheda 4-E3一(3，4-dihydroxy—
phenyl)一acryloyloxy]一2，3一dihydroxy一2一methyl—
butyricacid．
Theabovecompounds，themethylsignalsob—
servedat艿3．80in1H—NMRand艿53．1in
13C—NMRspectra，wereun quivocallyassociated
withanesterratherthananaromaticether，other—
wisebothsignalswouldbeshifteddownfieldE9|．
Underthebioassay—guidedisolation，sixcom—
poundsfromB．parviflorawereextractedandpu—
rifled，whosebi assayactivitiesar howni
Table3．
Table3 Antiallergieactivitiesofcaffeoylquinic
acidderivatives
。DPPH—reductions ave gingof2，2-diphenyl一肛picrylhydrazyladical
inhibitoryactivity；△His—histaminereleaseinhibitoryactivity；4NO—nitricox—
ide：Indomethacin8一amed cinetodiminishnflammationforhistaminerel ase
inhibitoryactivity；Q6quercetin3-O-glucoside，amedicinetodiminishinflam—
mationforDPPHinhibitoryactivity
Theser sultssuggestthedicaffeoylsubs—
titutionofquinicacidderivativeswhichever3，4一
or3，5一or4，3一substituteenhancetheiractivities
comparedtomono—caffeoylquinicacidderivativesin
bothofthehistamineandDPPHmodels．How—
ever，incontrasttheexist nceotquinineringin
thesecompoundswasecisivetoretaintheirn—
hibitoryeffectonNOproduction．Themethylas—
terofthecarboxylgroupinquinicderivatives
wouldimprovetheabilityofDPPH，inhibitionof
histaminerel ase，andNOproductionofthese
compounds．
Insummary，thecaffeoylquinicac deriva—
tiveshavegreatprospectsinfurtherd velopment
ofantioxidantand iinflammatorydrugs，andto
removerelativediseases．
Acknowledgements：Thisworkwasfinancially
supportedinartbyaGrant-inA dforScientific
Research(No．40102553)fromtheMinistryof
Education，Science，Sports，andCultu efJapan，
byaSpecialResearchGrant-inA dforthedeve—
lopmentofcharacteristiceducationandHigh—Tech
ResearchCenterf omtheJapaneseMinistryof
EducationandSciencetoNihonU iversityandb
theJapan—ChinaMedicalAssociation．
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万方数据
小花鬼针草中咖啡酰奎宁酸类成分及其抑制组胺释放活性
作者： 王珏， 王乃利， 姚新生， 北中進， WANG Jue， WANG Nai-li， YAO Xin-sheng，
KITANGAKA Susumu
作者单位： 王珏,北中進,WANG Jue,KITANGAKA Susumu(日本大学药学部生药学研究室,千叶,船桥,274-
8555,日本)， 王乃利,姚新生,WANG Nai-li,YAO Xin-sheng(沈阳药科大学天然药化教研室
,辽宁,沈阳,110016)
刊名： 中草药
英文刊名： CHINESE TRADITIONAL AND HERBAL DRUGS
年，卷(期)： 2006,37(7)
被引用次数： 4次
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