[生物医药论文精品a]线纹香茶菜中木脂素的分离与结构鉴定_人人...

来自 : www.renrendoc.com/p-99480...ht 发布时间：2021-03-25

ISOLATIONANDSTRUCTUREIDENTIFICATIONOFLIGNANSFROMRABDOSIALOPHANTHOIDESBUCHHAMEXDDONHARAFENGWEISHENG1,ZANGXINYU1,ZHENGXIAOKE2,WANGYANZHI1,LIHONGWEI1ANDLIZHEN11SCHOOLOFPHARMACY2BASICMEDICALCOLLEGE,HENANUNIVERSITYOFTRADITIONALCHINESEMEDICINE,1JINSHUIROAD,ZHENGZHOU450008,CHINAABSTRACTTOSTUDYTHECHEMICALCONSTITUENTSOFRABDOSIALOPHANTHOIDESBUCHHAMEXDDONHARAVARIOUSCOLUMNSINCLUDINGDIAIONHP20,TOYOPEARLHW40C,SEPHADEXLH20,SILICAGELWEREEMPLOYEDFORTHEISOLATIONANDPURIFICATIONOFCOMPOUNDSFROMRABDOSIALOPHANTHOIDESBUCHHAMEXDDONHARATHESTRUCTURESOFTHECOMPOUNDSWEREELUCIDATEDBYTHEIRPHYSIOCHEMICALCHARACTERISTICSANDSPECTRALDATATWONEWDIHYDROBENZOFURANLIGNANOSIDES,LOPHANTHOSIDEB1ANDAENANTIOMEROFUMBROSIDE2,ALONGWITHSEVENKNOWNLIGNANS39,WEREISOLATEDFROMRABDOSIALOPHANTHOIDESBUCHHAMEXDDONHARACOMPOUND16WASSOLATEDFROMTHISSPECIESFORTHEFIRSTTIME,ALLTHECOMPOUNDSWEREISOLATEDFROMTHISPLANTFORTHEFIRSTTIMEKEYWORDSRABDOSIALOPHANTHOIDESCHEMICALCONSITITUENTSLIGNANS线纹香茶菜中木脂素的分离与结构鉴定A1A0A21A4A5A3A61A4A8A7A92A4A11A10A121A4A14A13A151A4A14A161A18A17A19A20A21A22,1A24A21A222A25A23A20A21A22,A26A27A28A29A30A31A321A33450008A34A35A36A37A38A39A40A41A42A43A44A45A46A47A48A49A50A51A52A53DIAIONHP20A50TOYOPEARLHW40CA50SEPHADEXLH20A50SILICAGELA54A55A56A57A58A59A60A61A49A62,A63A64A65A66A46A67A68A69A70A57A71A64A72A73A46A74A75A76A77A78A49A62A79A80A81A82A83A45A84A85A81A86A87A88A89A90A91A92,LOPHANTHOSIDEB1A93A94A95UMBROSIDEA96A97A98A992,A100A101A102A95A103A104A96A105A106A107A108A109A110A111A112A113A114A109A110A11116A115A116A117A118A119A120A121A111A114A122A123A124A125A126A96A109A110A111A127A115A116A117A118A128A129A130A131A132A114A122A123A112A133A134A135A134A135A134A135A136A136A136A137A138A139A140A141A142A143A144A145A146A142A147A148A149ISODONRABDOSIAISACOSMOPOLITANANDIMPORTANTGENUSOFTHELABIATAELAMIACEAEFAMILYABOUT150SPECIESOFUNDERSHRUBS,SUBUNDERSHRUBSORPERENNIALHERBSAREFOUNDTHROUGHOUTTHEWORLDMAINLYINTROPICALANDSUBTROPICALASIATHEUSEOFISODONSPECIESINCHINESEPOPULARFOLKMEDICINEHASALONGTRADITIONMOSTHERBSOFTHISSPECIESHAVEBEENFOUNDTOHAVEOBVIOUSBIOLOGICALACTIVITIESWITHLOWTOXICITYRABDOSIALOPHANTHOIDESBUCHHAMEXDDONHARAHASBEENUSINGFORTHETREATMENTOFACUTEICTERICHEPATITIS,ACUTECHOLECYSTITI,SPHAGITIS,GYNAECOPATHIA1,ANDSOONHOWEVER,FEWOFTHEPHYTOCHEMICALSTUDIESOFTHEPLANT,ESPECIALLYLIGNANS,HAVEBEENREPORTEDPREVIOUSLYTHEFIRSTINVESTIGATIONONISODONSPECIESCANCORRESPONDINGAUTHORTEL8637165680011,FAX8637165680011,EMAILFWSHHACTCMEDUCNOOHOH3COOCH3OHOHOOHOH3COOCH3OHOCH3OCH3HOHOHOOHHOOHOOHOHOOHOOHMEOOCOOMEOHOMEOH123456783\'9\'97\'8\'OHOOOHHOOHHOOMEOOHOHOOR1MEOR3OOR2OHOOHOOHOCH3OCH3HOHOHOOHHOBETRACEBACKTO1900SDURINGTHESEYEARS,HUNDREDSOFDITERPENOIDSHAVEBEENFOUND,ANDANUMBEROFTHOSEISOLATEDDITERPENOIDSHAVEBEENFOUNDTOHAVEPOTENTANTITUMOURACTIVITIES2HOWEVER,DIHYDROBENZOFURANLIGNANSANDTHEIRGLYCOSIDES,WHICHALSOACTASANIMPORTANTBIOLOGICALACTIVITIESGROUP,HAVENEVERBEENFOUNDINISODONSPECIESBEFOREINTHISPAPER,WEREPORTTHATTWONEWDIHYDROBENZOFURANLIGNANOSIDES,LOPHANTHOSIDEB1ANDAENANTIOMEROFUMBROSIDE2,ALONGWITHFOURKNOWNLIGNANS39,THEYWEREALLISOLATEDFROM50AQUEOUSACETONEEXTRACTOFRABDOSIALOPHANTHOIDESBUCHHAMEXDDONHARATHECHEMICALSTRUCTURESOF19WEREFULLYELUCIDATEDBYEXTENSIVESPECTROSCOPICMETHODSINCLUDING1HAND13CNMR,1H,1HCOSY,HMBC,HSQC,ANDNOESYEXPERIMENTSANDHRESIMS12789RESULTSANDDISCUSSIONCOMPOUND1WASOBTAINEDASAWHITE,AMORPHOUSPOWDER,WITHTHEMOLECULARFORMULAR1R2R33HHGLU4HHH5MEGLUH6MEGLUHC34H40O15,ASDEDUCEDFROMTHEMNAPEAKATM/Z7112260BYHRESIMSIRSPECTRUMEXHIBITEDABSORPTIONOFOHGROUPS3423CM1,CARBONYL1697CM1,ANDAROMATICRINGS1612,1516CM1,THEUVSPECTRUMSHOWEDABSORPTIONMAXIMUMAT280NM,INDICATINGTHEPRESENCEOFAROMATICRINGTHE1HNMRAND13CNMRSPECTRAOF1TABLE1CLEARLYSHOWEDTHEPRESENCEOFDIHYDROBENZOFURANSKELETON,WITHONEGLUCOSEMOIETYΔH441D,J78HZ,1H,330M,1H,358M,1H,342M,2H,439M,1H,476M,1HΔC1040C1“,751C2“,756C3“,720C4“,780C5“,653C6“,,ONEMETHOXYLΔH376S,3HΔC564MEOANDTHESIGNALSOFASYRINGOYLMOIETYΔH729S,2H,374S,6HΔC1210C1“\'1082C2“\'6“\'1492C3“\'5“\'1425C4“\'1681CO5672MEOTHEDIHYDROBENZOFURANSKELETONWASIDENTIFIEDBYCOMPARISONOFITSNMRSPECTRALDATAWITHTHOSEREPORTED3THESKELETALSTRUCTRUEWASESTABLISHEDBYTHEHMBCCORRELATIONSBETWEENHC6“ΔH439,476MANDCOΔC1681,ANDBETWEENHC1“ΔH441D,J78HZANDC9ΔC727,ANDBETWEENHCMEOΔH376SANDC3ΔC1492ITWASCONCLUDEDTHATTHESYRINGOYLMOIETYCOULDBELOCATEDATC6“OFTHEGLUCOSEGROUP,ANDTHEOGLUCOPYRANOSYLCOULDBELOCATEDATC9ANDTHEMETHOXYLATC3,RESPECTIVELYINADDITION,THEABSOLUTECONFIGURATIONOFC7ΔC894ANDC8ΔC541WASFURTHERPROVEDBYMEANSOFITSDIFFERENTCHEMICALSHIFTSIN13CNMRACCORDINGTOTHEREPORT3,4C7Δ880895ANDC8Δ535550WAS7R,8SC7Δ865875ANDC8Δ565575WAS7S,8R,ANDATRANSCONFIGURATIONBETWEENC7ANDC8WASDETERMINEDFROMTHECOUPLINGCONSTANTJ60HZ5THESEDATASUGGESTEDTHATTHEABSOLUTECONFIGURATIONOFC7ANDC8INCOMPOUND1WASRANDS,RESPECTIVELYONTHEBASISOFSPECTRALEVIDENCE,THESTRUCTUREOFCOMPOUND1WASELUCIDATEDAS7R,8S4,3\',9\'TRIHYDROXYL3METHOXYL7,8DIHYDROBENZOFURAN1\'PROPYLNEOLIGNAN9O6OSYRINGOYLΒDGLUCOPYRANOSIDECOMPOUND2WASOBTAINEDASAWHITE,AMORPHOUSPOWDER,WITHTHEMOLECULARFORMULAC25H32O11,ASDEDUCEDFROMTHEMNAPEAKATM/Z5311841BYHRESIMSIRSPECTRUMEXHIBITEDABSORPTIONOFOHGROUPS34003500CM1ANDAROMATICRINGS1608,1510CM1,THEUVSPECTRUMSHOWEDABSORPTIONMAXIMUMAT214,233AND282NM,INDICATINGTHEPRESENCEOFAROMATICRINGTHE1HNMRAND13CNMRSPECTRAOF2TABLE1EXHIBITEDTHECHARACTERISTICPATTERNOFADIHYDROBENZOFURANSKELETON,WITHONEGLUCOSEMOIETYΔH501D,J75HZ,1H,332M,1H,334M,1H,340M,1H,329M,1H,365M,1H,376M,1HΔC1027C1“,748C2“,776C3“,713C4“,780C5“,622C6“,,ANDONEMETHOXYLΔH376S,3HΔC564MEOTHESKELETALSTRUCTRUEWASESTABLISHEDBYTHEHMBCCORRELATIONSBETWEENHC1“ΔH501D,J75HZANDC3\'ΔC1424,ANDBETWEENHCMEOΔH380SANDC3ΔC1491ITWASCONCLUDEDTHATTHEOGLUCOPYRANOSYLCOULDBELOCATEDATC3\'ANDTHEMETHOXYLATC3THESTRUCTUREOF2ISCLOSELYRELATEDTOTHATOFUMBROSIDE6,EXCEPTFORTHE1HNMRAND13CNMRDATEOFC7ANDC8THEABSOLUTECONFIGURATIONOFC7ΔC894ANDC8ΔC549WASPROVEDBYMEANSOFITSDIFFERENTCHEMICALSHIFTSIN13CNMRACCORDINGTOTHEREPORT3,4C7Δ880895ANDC8Δ535550WAS7R,8SC7Δ865875ANDC8Δ565575WAS7S,8R,ANDATRANSCONFIGURATIONBETWEENC7ANDC8WASDETERMINEDFROMTHECOUPLINGCONSTANTJ60HZ5THECDSPECTRAEXHIBITEDPOSITIVECOTTONEFFECTAT221NM∆Ε214OFCOMPOUND2APOSITIVECOTTONEFFECTAT223NM∆Ε119WASREPORTEDWITH2R,3S2,3DIHYDROY24\'HYDROXY3\'METHOXYPHENYL3HYDROXYMETHYL7METHOXY5BENZOFURANPROPANOL4\'OΒDGLUCOPYRANOSID7THESEDATASUGGESTEDTHATTHEABSOLUTECONFIGURATIONOFC7ANDC8INCOMPOUND2WASRANDS,RESPECTIVELYONTHEBASISOFSPECTRALEVIDENCE,THESTRUCTUREOFCOMPOUND2WASELUCIDATEDAS7R,8S4,9,9\'TRIHYDROXYL3METHOXYL7,8DIHYDROBENZOFURAN1\'PROPYLNEOLIGNAN3\'OΒDGLUCOPYRANOSIDE,AENANTIOMEROFUMBROSIDETABLE1HAND13CNMRDATAOF1AND2AT400AND100MHZ,RESP,INCD3ODΔINPPM,JINHZARBITRARYATOMNUMBERINGPOSITION12ΔHΔCΔHΔC1135013422694D,J181107685D,J1711083149214914147214765669D,J801160666D,J8111626680DD,J80,181196674DD,J81,1712007554D,J58894550D,J628948359M541341DD,J121,635499399M727376M6483OME376S564380S5641\'136813712\'656BRS1168681BRS11793\'141914244\'148914735\'129113056\'656BRS1171670BRS11957\'251T,J80326260T,J803278\'177M357180M3559\'353T,J68623352T,J686241\'\'441D,J751040501D,J7510272\'\'330M751332M7483\'\'358M756334M7764\'\'342M720340M7135\'\'342M780329M7806\'\'476M439M653365M376M6221“\'12102“\',6“\'729S10823“\',5“\'14924“\'1425MEO374S567CO1681COMPOUND39WEREELUCIDATEDAS7S,8R4,9,9\'TRIHYDROXYL3\'METHOXYL7,8DIHYDROBENZOFURAN1\'PROPYLNEOLIGNAN3OΒDGLUCOPYRANOSIDE3,7S,8R3\',4,9,9\'TETRAHYDROXYL3METHOXYL7,8DIHYDROBENZOFURAN1\'PROPYLNEOLIGNAN4,7S,8R4,9′DIHYDROXYL3,3′DIMETHOXYL7,8DIHYDROBENZOFURAN1′PROPYLNEOLIGNAN9OΒDGLUCOPYRANOSIDE5,7S,8R4,9,9\'TRIHYDROXYL3\',3′DIMETHOXYL7,8DIHYDROBENZOFURAN1\'PROPYLNEOLIGNAN6,SYRINGARESINOL4OΒDGLUCOPYRANOSIDE7,4,4′,8TRIHYDROXYL3,3′DIMETHOXYLBISEPOXYLIGNAN8HYDROXYPINORESINOL8,PINORESINOL4OΒDGLUCOPYRANOSIDE9,RESPECTIVELY,WITHTHEHELPOFSPECTROSCOPICTECHNIQUESTHEIR1HAND13CNMRDATAWEREINAGREEMENTWITHTHEONESREPORTEDINTHELITERATUREEXPERIMENTALSECTIONMELTINGPOINTSWEREDETERMINEDONAKOFLERMICROMELTINGPOINTAPPARATUSUNCORRECTEDOPTICALROTATIONSWEREMEASUREDWITHAPERKINELMER341POLARIMETERCDSPECTRAWERERECORDEDONAJASCOJ715SPECTROPOLARIMETERUVSPECTRAWEREMEASUREDWITHASHIMADZUUVVIS2201SPECTROPHOTOMETERIRSPECTRAWEREMEASUREDWITHASHIMADZUFTIR8201PCSPECTROMETERTHE1HAND13CNMRSPECTRAWEREOBTAINEDONABRUKERDPX400SPECTROMETER400OR300MHZFOR1HNMRAND100MHZFOR13CNMRWITHTMSASINTERNALSTANDARDHRESIMSWERERECORDEDONANAPEXIISPECTROMETERCOLUMNCHROMATOGRAPHYWASPERFORMEDONDIAIONHP20MITSUBISHICHEMICALCORP,JAPAN,SILICAGEL160200MESH,QINGDAOHAIYANGCHEMICALCO,LTD,CHINA,TOYOPEARLHW40CTOSOHCORP,JAPANTLCWASCONDUCTEDONSELFMADESILICAGELGQINGDAOHAIYANGCHEMICALCO,LTD,CHINAPLATESTHECHEMICALREAGENTSWEREPURCHASEDFROMBEIJINGCHEMICALPLANTANDTIANJINNO3REAGENTPLANTEMULSINANDHESPERIDINASEWEREPURCHASEDFROMSIGMACHEMCO,ANDRANDSΑTRIFLUOROMETHYLPHENYLACETICACIDSMTPAWEREFROMNACALAITESQUECO,LTDPLANTMATERIALDRIEDRABDOSIALOPHANTHOIDESWERECOLLECTEDFROMJIYUANCOUNTY,HENANPROVINCEINCHINA,ANDIDENTIFIEDBYPROFDONGCHENGMINGOFHENANUNIVERSITYOFTRADITIONALCHINESEMEDICINEAVOUCHERSPECIMENNO20060609ISDEPOSITEDINTHEHERBARIUMOFHENANUNIVERSITYOFTCM,ZHENGZHOU,PEOPLE’SREPUBLICOFCHINAEXTRACTIONANDISOLATIONDRIEDPLANTS90KGOFRLOPHANTHOIDESWEREEXTRACTEDBY50AQUEOUSACETONETWICEATROOMTEMPERATURE,ANDCONCENTRATEDUNDERREDUCEDPRESSUREBELLOW40THEWATERSOLUTABLE℃PARTWASCHROMATOGRAPHEDOVERDIAIONHP20WITHH2OCONTAININGINCREASINGAMOUNTOFMEOH,THE20MEOHELUATE106GWASCHROMATOGRAPHEDONTOYOPEARLHW40COARSEGRADEDEVELOPINGWITH10MEOH50MEOHTHE20MEOHELUTE29GWASRECHROMATOGRAPHEDONTOYOPEARLHW40ANDONSILICAGELTOYIELDCOMPOUND160MGANDCOMPOUND215MGTHE30MEOHELUATE119GWASCHROMATOGRAPHEDONTOYOPEARLHW40COARSEGRADEDEVELOPINGWITH10MEOH50MEOHTHE10MEOHELUTE16GWASRECHROMATOGRAPHEDONTOYOPEARLHW40ANDONSILICAGELTOYIELDCOMPOUND350MGAND425MGTHE40MEOHELUATE93GWASCHROMATOGRAPHEDONTOYOPEARLHW40COARSEGRADEDEVELOPINGWITH10MEOH50MEOHTHE10MEOHELUTE20GWASRECHROMATOGRAPHEDONTOYOPEARLHW40ANDONSILICAGELTOYIELDCOMPOUND520MG,COMPOUND620MG,730MG,815MGAND925MGIDENTIFICATION7S,8R3\',9,9\'TRIHYDROXYL3METHOXYL7,8DIHYDROBENZOFURAN1\'PROPYLNEOLIGNAN4OΒDGLUCOPYRANOSIDE3WHITEPOWDER,1HNMRCD3OD,400MHZ486D,J80,1H552D,J60,1H656S,1H658S,1H694DD,J84,16,1H705D,J16,1H713D,J84,1H13CNMRCD3OD,100MHZ3271C8′3581C7′5500C85665C3′OME6247C9′6520C98817C711106C211634C2′11666C511794C6′11931C612946C1′13689C5′13862C114194C3′146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