爱华网J.Nat.Prod.2000,63,1373-13761373
StilbeneGlycosideSulfatesfromPolygonumcuspidatum
KaiXiao,LijiangXuan,YamingXu,*andDongluBai
ShanghaiInstituteofMateriaMedica,ChineseAcademyofSciences,294TaiyuanRoad,Shanghai200031,People’sRepublicofChinaReceivedFebruary18,2000
Tennaturallyoccurringstilbeneglycosidesulfates(1-10)wereisolatedfromanaqueousextractoftherootofPolygonumcuspidatum.Theirstructureswereestablishedbasedonchemicalevidenceandspectroscopictechniques,including2DNMRmethods.
ThedriedrootsofPolygonumcuspidatumSieb.etZucc.(Polygonaceae)havebeenwidelyusedinChinesefolkmedicineforthetreatmentofsuppurativedermatitis,gonorrhea,favusathlete’sfoot,andhyperlipemia.Manychemicalcomponentshavebeenreportedfromthehydro-phobicfractionofthisplant,includinganthroquinones,1-4stilbenes,5-7flavonoids,8andotherphenols.3
Stilbeneshavearousedconsiderableinterestfortheirbioactivities.Resveratrolandpiceidhavebeenreportedtohavelipid-loweringactivity9andtoinhibitlipidperoxida-tion,10arachidonatemetabolism,11,12andproteintyrosinekinase(PTK56lck).7Resveratrolalsopossessesantibacterialandantifungaleffects6aswellastumorchemopreventiveactivities,13andpiceidimprovesmicrocirculation.14
InastudyofanaqueousacetoneextractoftherootsofP.cuspidatum,10naturallyoccurringstilbeneglycosidesulfates(1-10)wereisolatedandidentified.Therehasbeennopreviousphytochemicalworkreportedontheaqueoussolublecomponentsfromthisplant,andtherehasbeennoreportintheliteratureonstilbenoidsulfates.
andtheir1Hand13CNMRdatawereunambiguouslyassignedby2DNMRanalysis.
Compound1wasisolatedasanamorphouspowder.ItexhibitedFABMSionsatm/z493,508,515,531,and547,indicatingamolecularweightof492or508,compatiblewithamolecularformulaofC20H21O11NaSorC20H21O11-KS.Thisconclusionwasconsistentwithatomicabsorptiondata.ApositiveMolishtestindicatedthat1mightbeaglycoside.TheIRspectrumindicatedthepresenceofhydroxyl(3405cm-1),double-bond(1606cm-1),aromatic(1589and1513cm-1),and-OSO3-(1254and1064cm-1)groups.15,16ThepresenceofSwasconfirmedbyelementalanalysis,whilethepresenceofK+wasdeterminedfromatomicabsorptionanalysis.TheUVspectrumsuggestedthat1possessedastilbeneskeleton.171Hand13CNMRdataconfirmedthat1wasatrans-resveratrolglycoside.7,18Hydrolysisof1affordedD-glucose(determinedbyGCanalysis);theanionSO42-,whichwasconfirmedbyprecipitationwithBaCl2;andresveratrol,whichwasidentifiedbycomparisonofIRandNMRdatawithlitera-ture.7The1Hand13CNMRdataindicatedthatthesugarwas
