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Two (2)

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Two (2)two,two2,TWO,Two 2,TWO2,2two,Two

    Two

ChineseChemicalLettersVo1.16,No.5,PP625626,2005

    ;http://www.imm.ac.cn/journal/cc1.html

    ;TwoNewent.KaurenoidsfromCacaliapilgeriana

    ;ErWeiLI,KunGAO*,ZhongJianJIA,XinZHAO

    ;CollegeofChemistryandChemicalEngineering,NationalLaboratoryof ;AppliedOrganicChemistry,LanzhouUniversity,Lanzhou730000 ;Abstract:Twonewentkaurenoids,19acetylent3B

    ;3Bhydroxykaur15en17al(2)wereisolatedfrom

    ;elucidatedbyspectroscopicmethods.

    ;625

    ;17-dihydroxykau15ene(1),19acetylent

    ;Cacaliapilgeriana.Theirstructureswere

    ;Keywords:Cacaliapilgeriana,Compositae,entkaurenoids

    ;Phytochemically.thegenusCacaliawascharacterizedbycontainingsesquiterpenes, ;onlyNasrreportedaseriesofkaurenoidditerpenesfromCctcaliabulbra.Inthis ;paperwedescribethestructuralelucidationoftwonewentkaurenoidsisolatedfromthe

    ;methanolextractoftherootsofCacaliapilgerianafDiels)Ling. ;Compound1wasobtainedascolorlesscrystalfromacetone,mp.157158?,10j

    ;

    ;55(c3.4,CH10H1.ThemolecularformulaC22H3404wasyieldedbasedontheEIMS

    ;atm/z362(M1+).whichwasalsoconfirmedbyHRESIMSatm/z345.2425

    ;MH20+H+(calcd.345.2424)and327.2299IM2H20+H+(calcd.327.2319).TheH

    ;NMRspectrumof1showedthesignalsforthreetertiarymethyls(61.O3,1.13and2.07, ;s.each3H),twooxygenatedmethylenes(64.12and4.33,d,each1H,J:l1.2Hz;64.55 ;s,2H,anoxygenatedmethine(63.28,dd,1H,J=l1.2,5.2Hz)andanolefinicmethine ;(65_48,s,1H).Furthermore,the”CNMRandDEPTspectrashowed22signalsfor

    ;3xCH3,9xCH2(twoofwhichwereoxygenated),5xCH(onewasoxygenated),5xC(one ;wascarbony1).TheNMRspectraldataof1weresimilartothoseofent313,

    ;19dihydroxykaur16eneanditsdiacetatedderivative.thedifierenceswereonlyhat

    ;theolefinicbondin1waslocatedatC15(16),andahydroxylmethylgroupatC17.

    ;Thiswasconfn-rnedbythecorrelationofH15withC17.andH17withC15inthe

    ;HMBCspectrum.TheacetylgrouplocatedatC19whichwasdeducedbythepresence

    ;oftheHMBCcrosspeakofH19withCHC0(6f171.18).ThechemicalshiftofH3

    ;(63.28,dd,J:l1.2,5.2Hz)showedthehydroxylgroupwas1orientation..Thus,

    ;compound1wasdeterminedas19acetylent.313.17-dihydroxykaur-15ene.

    ;Compound2,colorlessgum,0【一82(c0.1,CHzOH),hasthemolecularformula

    ;c22H32O4deducedfromitsHREsIMsatm/z361.2369M+H+(calcd.361.2373).1ts

    ;NMRspectraldatawereverysimilartothoseof1exceptforthepresenceofa_CHOin ;Email:jiazj@lzu.edu.cn;miaozm@lzu.edu.cn

;

    ;626ErWeiLIelaf

    ;2(C17:6H,9.72,s,1H;6c,189.35)insteadoftheCH2OHin1(C17:6H,4.55,S,2H;

    ;6c,75.02).Therefore,compound2waselucidatedas19acetylent3phydroxykaur-

    ;15en17a1. ;Ho

    ;Table1HNMR(400MHz),”CNMR(100MHz)andDEPTdataof1,2(CDC13,TMS,6ppm)

    ;2l6rDEPT26rDEPT

    ;1

    ;2

    ;3

    ;4

    ;5

    ;6

    ;7

    ;8

    ;9

    ;lO

    ;l1

    ;l2

    ;l3

    ;l4

    ;15

    ;l6

    ;l7

    ;18

    ;l9

    ;20

    ;oAc

    ;3.28(dd,112,5.2)327(dd,112,60)

    ;2.64”n1

    ;548(s)

    ;4.55(s)

    ;1.13(s)

    ;412fd.

    ;1.03(s)

    ;2.07(s)

    ;304”n1

    ;6.55(s)

    ;972rs1

    ;1.14fs,

    ;11.2),433(d,11.2)4.11(d,11.7),432(d,117)

    ;1.06(s)

    ;207fs)

    ;39.15 ;25.30 ;79.17 ;4227 ;55.49 ;194_4 ;4345 ;48.95 ;48.06 ;3899 ;1878 ;27.18 ;41.58 ;3877 ;l4035 ;l41.31 ;75.02 ;22.39 ;6534 ;l78l ;l71.18 ;21.10 ;3838 ;25.06 ;79.04 ;42-23 ;5543 ;1918 ;4275 ;46.84 ;4664 ;388l ;18.62 ;27.2l ;40.80 ;37.90 ;l39.99 ;l4883 ;l8935 ;22.49 ;65-20 ;l784 ;l7l05 ;21.10

;Acknowledgments

    ;ThisworkwassupportedbytheNNSFC(No.29972017andNo.20021001QTProgram)

    ;References

    ;1.S.M.Zhang,GL.Zhao,R.Li,GO.Lin,Phytochenistry,1998,48(3),519. ;2.M.J.Mao,Z.J.Jia,PlantaMedica,2002,68(1).55.

    ;3.M.J.Mao,Z.D.Yang,Z.J.Jia,PlantaMedica,2003,69(8),745. ;4.A.E.E.Nasr,K.Genjiro,T.Tsunematsu,Phytochenistrv197514(7)1660. ;5.P.Franco,S.Giuseppe.R.H.James,Phytochenistry,1980,19(6),1237. ;6.J.C.Stephen,GPaul,H.B.Michael,R.L.John,Phytochemistrv,1995,39(1),11 ;Received21May,2004

    ;HCH一二.CHC:HHCHCdccccc

    ;HCHCHCHHCCdcccc

    ;

    ;

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