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Chemical constituents from the leaves of Alchornea trewioides(2). Flavonoids and phenylethanoid glycosides

红背山麻杆叶的化学成分研究(Ⅱ)——黄酮和苯乙醇苷类化合物



全 文 :广 西 植 物 Guihaia Mar.2014,34(2):143-147           http://journal.gxzw.gxib.cn 
DOI:10.3969/j.issn.1000G3142.2014.02.001
黄永林,刘金磊,陈月圆,等.红背山麻杆叶的化学成分研究(Ⅱ)———黄酮和苯乙醇苷类化合物[J].广西植物,2014,34(2):143-147
HuangYL,LiuJL,ChenYY,etal.ChemicalconstituentsfromtheleavesofAlchorneatrewioides(2).Flavonoidsandphenylethanoidglycosides[J].
Guihaia,2014,34(2):143-147
ChemicalconstituentsfromtheleavesofAlchornea
trewioides(2).Flavonoidsandphenylethanoidglycosides
HUANGYongGLin,LIUJinGLei,CHENYueGYuan,
YANGZiGMing,YANXiaoGJie,LIDianGPeng∗
(GuangxiKeyLaboratoryofFunctionalPhytochemicalsResearchandUtilization,
GuangxiInstituteofBotany,Guilin541006,China)
Abstract:The80%acetoneextractsofthefreshleavesofAlchorneatrewioideswassuccessivelyseparatedbySephaG
dexLHG20,MCIgelCHP20P,ODS,andToyopearlButylG650Ccolumnchromatographytoyieldsevenflavonoids
andthreephenylethanoidglycosides.Theirstructureswereelucidatedbyspectroscopicanalysesas:quercetin(1),
quercetinG3Grhamnoside(2),quercetinG3GOGβGDGglucopyranoside(3),rutin(4),apigeninG6GCGβGDGglucopyranoside(5),
apigeninG8GCGβGDGglucopyranoside(6),luteolinG7GOGaGLGrhamnopyranosyl(1→6)GβGDGglucopyranoside(7),2GphenyleG
thylβGDGglucopyranoside(8),icarisideD1(9),and2GphenylethylDGrutinoside(10).Compounds1-3,5-6,8-10
wereisolatedfromtheAlchorneaforthefirsttime.
Keywords:Alchorneatrewioides;chemicalconstituents;flavonoid;phenylethanoidglycoside
CLCnumber:Q946.8  Documentcode:A  ArticleID:1000G3142(2014)02G0143G05
红背山麻杆叶的化学成分研究(Ⅱ)
———黄酮和苯乙醇苷类化合物
黄永林,刘金磊,陈月圆,杨子明,颜小捷,李典鹏∗
(广西植物功能物质研究与利用重点实验室,广西植物研究所,广西 桂林541006)
摘 要:采用80%丙酮提取物的水萃取部位,利用凝胶、MCI、反相碳18、及ToyopearlButylG650C柱色谱进
行分离纯化得到7个黄酮和3个苯乙醇苷类化合物.根据化合物的波谱数据分析鉴定为槲皮素(1)、槲皮苷
(2)、异懈皮苷(3)、芦丁(4)、异牡荆素(5)、牡荆素(6)、木犀草素G7GOGαGLG鼠李糖(1→6)GβGDG葡萄糖苷(7)、2G
phenethylβGDGglucoside(8)、icarisideD1(9)、2G苯乙基GDG芸香甙(10).其中化合物1-3、5-6、8-10为首次
从本属植物中分离得到.
关键词:红背山麻杆;化学成分;黄酮;苯乙醇苷
  ThegenusAlchorneabelongstothefamilyEuG
phorbiaceaeandcontainsapproximately70species.
Over6specieshavebeenrecordedinChina(Editorial
CommitteeinFloraofChina,1996),manyofwhich
havebeenusedfortreatinginflammationoftheprosG
tategland,hematuria,shigela,inflammation,lumboG
收稿日期:2013G10G15  修回日期:2013G12G12
基金项目:广西自然科学基金(2011GXNSFD018038);广西科技合作与交流计划项目(桂科合1298014G10);广西植物研究所基本业务费(桂植业
13002);广西植物功能物质研究与利用重点实验室开放基金(ZRJJ2013G7).
作者简介:黄永林(1974G),男,广西桂林人,博士,研究员,主要从事天然产物物质基础、生物活性及开发利用研究,(EGmail)hyl@gxib.cn.
∗通讯作者:李典鹏,博士,研究员,从事中药、天然药物和植物化学研究,(EGmail)ldp@gxib.cn.
cruralpainand manyotherdiseases(Jiangsu New
MedicalColege,1977).TheA.trewioidesbelongsto
thefamilyAlchornea,itwasusedastraditionalmediG
cinestoaleviatediseaseanddiscomfort.Previously,
flavonoidglycosides,phenolicacidsandantioxidantacG
tivityhavebeenreportedfromthespecies(Lu,2012;
Qin,2012;Lu,2011;Huang,2014).TofurtherreG
searchforthematerialbasisofpharmacologicalefects
fromthespeciesA.trewioides,sevenflavonoidsand
threephenylethanoidglycosideswereisolatedfromthe
80%acetoneextractsofthefreshleavesofAlchornea
trewioides.Compounds1-3,5-6,8-10wereisolaG
tedfromtheAlchorneaforthefirsttime.
1 Materialsandmethods
1HGand13CGNMRspectraweremeasuredinCD3
ODoracetoneGd6at27℃usingaBrukerAvance500
spectrometer(500MHzfor1Hand125MHzfor13C)
(BrukerBiospinAG,Faelanden,Switzerland)oraJEG
OLJNMGAL400spectrometer(400MHzfor1Hand
100MHzfor13C)(JEOLLtd.,Tokyo,Japan).CouG
plingconstantswereexpressedin Hzandchemical
shiftsaregivenonaδ(ppm)scale.ColumnchromatogG
raphywasperformedusingMCIgelCHP20P(75G150
μm;MitsubishiChemical,Tokyo,Japan),Sephadex
LHG20(25-100mm;GEHealthcareBioGScienceAB,
Uppsala,Sweden),ChromatorexODS(100G200mesh,
FujiSilysiaChemicalLtd.,kasugai,Japan),andToyoG
pearlButylG650C(TOSOH Co.,Tokyo,Japan)colG
umns.TLCwasperformedonprecoatedKieselgel60
F254plates(0.2mmthick;Merck,Darmstadt,GermaG
ny)withCHCl3GMeOHGH2O(9∶1∶0.1,8∶2∶0.2,
or7∶3∶0.5,v/v)andtolueneGethylformateGformic
acid(1∶7∶1,v/v)asthesolvent,andspotsweredeG
tectedbyUVilumination(254nm)andbyspraying
witha2%ethanolicFeCl3and10%sulfuricacidreaG
gent,folowedbyheating.
TheleavesofA.trewioides werecolectedat
GuangxiInstituteofBotany,Guangxi,China,inAugust
2011,andidentifiedbyProf.WeiFanan.Thevoucher
specimen(20110920N)wasdepositedintheGuangxi
keylaboratoryoffunctionalphytochemicalsresearch
andutilization,GuangxiInstituteofBotany.
2 Extractionandseparation
ThefreshleavesofA.trewioides(5.35kg)were
cutintosmalpiecesandextractedwithacetoneGH2O
(8∶2,v/v)bymacerationatroomtemperature.After
filtration,theplantdebrisremainingonthefilterpaper
wasextractedwiththesamesolventafurthertwo
times.ThefiltratewascombinedandconcentratedunG
derreducedpressuretogiveanaqueoussolutionwith
darkgreenprecipitates.Theprecipitantwasmainly
composedofchlorophylsandwaxes,andremovedby
filtration.Theextract(610g)waspartitionedbetween
H2O(3L)andEt2O(1L)3times.Theaqueouslayer
wasfractionatedbySephadexLHG20columnchromaG
tography(10cmi.d.×40cm)withwatercontaininginG
creasingproportionsofMeOH(0-100%,10%stepG
wiseelution,each2L)andfinalywith60%acetone,to
yield9fractions(Fr.1-9).Fraction1(18.7g)was
separatedbyacombinationofcolumnchromatography
overMCIgelCHP20P(8cmi.d.×40cm)with0-
100% MeOH(10%stepwiseelution,each1L),ToyoG
pearl650C(2cmi.d.×30cm)with0-100% MeOH
(10%stepwiseelution,each300mL),andChromatorG
exODS(2cmi.d.×30cm)with0-100% MeOH
(10%stepwiseelution,each300mL),toaford8(285
mg),9(23mg),10(91mg).Fraction5(35.6g)was
separatedbyacombinationofcolumnchromatography
overMCIgelCHP20P(8cmi.d.×40cm)with0-
100% MeOH(10%stepwiseelution,each1L),and
SephadexLHG20(2cmi.d.×30cm)with0-100%
MeOH(10%stepwiseelution,each300mL),toaford
1(275mg).Fraction6(36.0g)wasfurtherfractionated
byMCIgelCHP20Pcolumnchromatography(8cmi.
d.×40cm)with0-100% MeOH(10%stepwiseeluG
tion,each1L)togiveninefractions:frs.6G1(6.30g),
2(1.02g),3(1.36g),4(2.45g),5(6.28g),6(6.10g),
7(4.12g),8(2.56g),9(1.25g).Fraction6G3(1.36g)
wassuccessivelyappliedtoaSephadexLHG20column
chromatography(3cmi.d.×30cm)with0-100%
MeOH(10%stepwiseelution,each200mL)toyield
2(20mg).Fraction6G8wassubjectedtoaSephadex
441 广 西 植 物                  34卷
Fig.1 Chemicalstructuresofcompounds1-10
LHG20columnchromatography(3cmi.d.×30cm)
with0-100% MeOH(10%stepwiseelution,each200
mL)toyield4(25mg),and5(36mg).Fraction6G9
wasfurtherfractionatedbySephadexLHG20column
chromatography(6cmi.d.×40cm)with10-100%
MeOH(10%stepwiseelution,each200mL),andthe
subfractionswerepurifiedbyToyopearlButylG650C(1
cmi.d.×30cm)with0-100% MeOH(10%stepG
wiseelution,each100mL)togetcompound3(6mg),
6(10mg),and7(648mg).
3 Resultsandanalysis
Quercetin(1)  Yelow amorphouspowder,
C15H10O7.1HGNMR(500MHz,CD3OD)δ:6.16(1H,
d,J=2.2Hz,HG6),6.36(1H,d,J=2.2Hz,HG8),
6.87(1H,d,J=8.5Hz,HG5′),7.61(1H,dd,J=2.2,
8.5Hz,HG6′),7.72(1H,d,J=2.2Hz,HG2′);13CG
NMR(125MHz,CD3OD)δ:94.4(CG8),99.2(CG6),
104.5(CG10),116.0(CG2′),116.2(CG5′),121.7(CG6′),
124.1(CG1′),137.2(CG3),146.2(CG3′),147.3(CG2),
148.7(CG4′),158.2(CG5),162.5(CG9),165.5(CG7),
177.3(CG4)(Xiao,etal.,2006;Markhametal.,1976).
QuercetinG3Grhamnoside(2)  Yelow amorG
phouspowder,C21H20O11.1HGNMR(400MHz,CD3
OD)δ:0.93(3H,d,J=5.9Hz,HG6″),3.34(1H,t,J=
5.8Hz,HG4″),3.40(1H,m,HG5″),3.73(1H,dd,J=
3.2,9.3Hz,HG3″),4.21(1H,brs,HG2″),5.34(1H,br
s,HG1″),6.18(1H,d,J=2.0Hz,HG6),6.36(1H,J=
2.0Hz,HG8),6.90(1H,d,J=8.3Hz,HG5′),7.30
(1H,dd,J=1.9,8.3Hz,HG6′),7.33(1H,J=1.9Hz,
HG2′);13CGNMR(100MHz,CD3OD)δ:17.8(CG6″),
71.9(CG2″),72.1(CG5″),72.2(CG3″),73.3(CG4″),94.7
(CG8),99.8(CG6),103.5(CG1″),105.9(CG10),116.4(CG
5′),116.9(CG2′),122.9(CG6′),123.1(CG1′),136.2(CG
3),146.5(CG4′),149.8(CG3′),158.7(CG2),159.5(CG9),
163.3(CG5),165.9(CG7),179.7(CG4)(Fossenetal.,
1999).
QuercetinG3GOGβGDGglucopyranoside (3)  
Yelowamorphouspowder,C21H20O12.1HGNMR(500
MHz,CD3OD)δ:3.21G3.83(6H,m,HG2‴,3‴,4‴,5‴,
6ax‴,6eq‴),5.10(1H,d,J=7.5Hz,HG1‴),6.18(1H,
d,J=2.0Hz,HG6),6.36(1H,d,J=2.0Hz,HG8),
6.88(1H,d,J=8.5Hz,HG5′),7.61(1H,dd,J=2.5,
8.5Hz,HG6′),7.68(1H,d,J=2.5Hz,HG2′);13CG
NMR(125MHz,CD3OD)δ:62.5(CG6‴),71.0(CG4‴),
75.6(CG2‴),78.2(CG3‴),78.4(CG5‴),95.2(CG8),98.2
(CG6),101.2(CG1‴),105.3(CG10),116.1(CG2′),116.3
(CG5′),123.2(CG1′),123.3(CG6′),135.9(CG3),146.2
(CG3′),150.1(CG4′),159.0(CG2),159.2(CG9),163.1(CG
5),166.4(CG7),179.4(CG4)(Liuetal.,2010).
Rutin(4) Yelowamorphouspowder,C27H30
O16.1HGNMR(500MHz,CD3OD)δ:1.15(3H,d,J=
5.8Hz,HG6‴),3.27G3.54(10H,m,HG2″,3″,4″,5″,
6ax″,6eq″,2‴,3‴,4‴,5‴),5.18(1H,brs,HG1‴),5.13
(1H,d,J=8.0Hz,HG1″),6.22(1H,brs,HG6),6.41
(1H,brs,HG8),6.89(1H,d,J=8.5Hz,HG5′),7.65
(1H,dd,J=2.0,8.5Hz,HG6′),7.68(1H,d,J=2.0
Hz,HG2′);13CGNMR(125MHz,CD3OD)δ:16.5(CG
6‴),67.2(CG6″),68.3(CG5‴),70.0(CG3‴),70.7(CG2‴),
70.9(CG4″),72.6(CG4‴),74.3(CG2″),75.8(CG5″),76.8
(CG3″),93.5(CG8),98.6(CG6),101.0(CG1‴),103.3(CG
1″),104.3(CG10),114.7(CG5′),116.3(CG2′),121.8(CG
6′),122.2(CG1′),134.2(CG3),144.4(CG3′),148.4(CG
5412期     黄永林等:红背山麻杆叶的化学成分研究(Ⅱ)———黄酮和苯乙醇苷类化合物
4′),157.1(CG9),157.9(CG2),161.7(CG5),164.6(CG7),
178.0(CG4)(Sangetal.,2001).
ApigeninG6GCGβGDGglucopyranoside(5) Yelow
amorphouspowder,C21H20O10.1HGNMR(500MHz,
CD3OD)δ:3.45G3.52(3H,m,HG3″,4″,5″),3.78(1H,
dd,J=6.5,12.0Hz,HG6ax″),3.92(1H,d,J=12.0
Hz,HG6eq″),4.21(1H,t,J=9.8Hz,HG2″),4.61(1H,
d,J=9.8Hz,HG1″),6.42(1H,s,HG8),6.49(1H,s,HG
3),6.89(2H,d,J=8.0Hz,HG3′,5′),7.42(2H,d,J=
8.0Hz,HG2′,6′);13CGNMR(125MHz,CD3OD)δ:61.5
(CG6″),70.4(CG2″),71.3(CG4″),73.9(CG1″),78.7(CG
3″),81.2(CG5″),93.9(CG8),102.4(CG3),103.8(CG10),
107.7(CG6),115.6(CG3′,5′),121.6(CG1′),128.0(CG2′,
6′),157.2(CG9),160.5(CG5),161.3(CG4′),163.4(CG7),
164.6(CG2),182.5(CG4)(Talitaetal.,2012;Maatooqet
al.,1997).
ApigeninG8GCGβGDGglucopyranoside(6) Yelow
amorphouspowder,C21H20O10.1HGNMR(500MHz,
CD3OD)δ:3.46G3.52(3H,m,HG3″,4″,5″),3.78(1H,
dd,J=6.5,12.0Hz,HG6ax″),3.92(1H,d,J=12.0
Hz,HG6eq″),4.21(1H,t,J=9.8Hz,HG2″),4.61(1H,
d,J=9.8Hz,HG1″),6.21(1H,s,HG6),6.45(1H,s,HG
3),6.90(2H,d,J=8.0Hz,HG3′,5′),7.98(2H,d,J=
8.0Hz,HG2′,6′);13CGNMR(125MHz,CD3OD)δ:61.3
(CG6″),70.6(CG2″),70.9(CG4″),73.4(CG1″),78.7(CG
3″),81.8(CG5″),98.2(CG6),102.5(CG3),104.1(CG8),
104.6(CG10),115.8(CG3′,5′),121.1(CG1′),128.9(CG
2′,6′),156.0(CG5),160.4(CG9),161.1(CG4′),162.7(CG
7),164.0(CG2),181.1(CG4)(Talitaetal.,2012).
LuteolinG7GOGαGLGrhamnopyranosyl(1→6)GβG
DGglucopyranoside(7) Yelowamorphouspowder,
C27H30O15.1HGNMR(500MHz,acetoneGd6)δ:1.20
(3H,d,J=6.5Hz,HG6‴),3.43G3.48(10H,m,HG2″,
3″,4″,5″,6ax″,6eq″,2‴,3‴,4‴,5‴),4.80(1H,brs,HG
1‴),5.16(1H,d,J=7.5Hz,HG1″),6.53(1H,brs,HG
6),6.68(1H,brs,HG8),6.87(1H,brs,HG3),7.04
(1H,d,J=8.5Hz,HG5′),7.47(1H,dd,J=2.0,8.5
Hz,HG6′),7.50(1H,d,J=2.0Hz,HG2′);13CGNMR
(125MHz,acetoneGd6)δ:17.1(CG6‴),66.2(CG6″),68.5
(CG5‴),69.8(CG4″),70.6(CG3‴),71.2(CG2‴),72.5(CG
4‴),73.3(CG2″),75.7(CG5″),76.3(CG3″),95.2(CG8),
100.0(CG6),100.4(CG1‴),100.6(CG1″),103.3(CG3),
105.8(CG10),113.3(CG5′),116.0(CG2′),119.5(CG6′),
122.2(CG1′),145.6(CG3′),149.7(CG4′),157.4(CG9),
161.3(CG5),163.3(CG7),165.3(CG2),182.5(CG4)
(Petrovicetal.,1999).
2GPhenylethylβGDGglucopyranoside(8)  AG
morphouspowder,C14H20O6.1HGNMR(400 MHz,
CD3OD)δ:2.93(2H,t,J=7.8Hz,H2Gβ),3.20(1H,
dd,J=7.8,8.5Hz,HG2′),3.29G3.42(3H,m,HG3′,4′,
5′),3.67(1H,dd,J=5.1,11.7Hz,HG6ax′),3.72(1H,
m,HGαax),3.87(1H,dd,J=3.2,11.7Hz,HG6eq′),
4.09(1H,m,HGαeq),4.31(1H,d,J=7.8Hz,HG1′),
7.18(1H,s,HG4),7.25(4H,m,HG2,3,5,6);13CGNMR
(100MHz,CD3OD)δ:37.2(CGβ),62.7(CG6′),71.3(CG
α),71.7(CG4′),75.0(CG2′),77.8(CG5′),78.0(CG3′),
104.6(CG1′),127.2(CG4),129.3(CG3,5),129.9(CG2,
6),140.0(CG1)(Miyaseetal.,1988;Kaoruetal.,
1988).
IcarisideD1(9) Colorlesssyrup,C19H28O10.
1HGNMR(400MHz,CD3OD)δ:2.93(2H,t,J=6.9
Hz,H2Gβ),3.17(1H,dd,J=7.8,9.0Hz,HG2′),3.29G
3.37(3H,m,HG3′,4′,5′),3.32G3.36(2H,m,HG5ax″,
5eq″),3.59(1H,dd,J=6.1,11.2Hz,HG6ax′),3.74
(1H,d,J=9.8Hz,HG4ax″),3.75(1H,m,HGαax),
3.89(1H,d,J=2.4Hz,HG2″),3.89(1H,d,J=9.8
Hz,HG4eq″),3.97(1H,dd,J=2.2,11.2Hz,HG6eq′),
4.04(1H,m,HGαeq),4.28(1H,d,J=7.8Hz,HG1′),
5.00(1H,d,J=2.4Hz,HG1″),7.16(1H,s,HG4),7.25
(4H,m,HG2,3,5,6);13CGNMR(100MHz,CD3OD)δ:
37.2(CGβ),65.6(CG5″),68.7(CG6′),71.7(CGα),71.8(CG
4′),75.0(CG2′),75.1(CG4″),76.9(CG5′),78.0(CG3′),
78.1(CG2″),80.5(CG3″),104.4(CG1′),111.0(CG1″),
127.2(CG4),129.3(CG3,5),130.0(CG2,6),140.0(CG1)
(Miyaseetal.,1987).
2GPhenylethylDGrutinoside(10)  Colorless
syrup,C20H30O10.1HGNMR(400MHz,CD3OD)δ:
1.20(3H,d,J=6.5Hz,HG6″),2.92(2H,t,J=7.0
Hz,H2Gβ),3.19(1H,dd,J=7.6,8.5Hz,HG2′),3.28
(1H,t,J=9.2Hz,HG4″),3.30G3.41(3H,m,HG3′,4′,
5′),3.61(1H,dd,J=5.5,11.2Hz,HG6ax′),3.67G3.69
(2H,m,HG3″,5″),3.72(1H,m,HGαax),3.82(1H,dd,
J=1.7,3.1Hz,HG2″),3.89(1H,dd,J=2.2,11.2Hz,
HG6eq′),4.04(1H,m,HGαeq),4.29(1H,d,J=7.6Hz,
HG1′),4.73(1H,d,J=1.7Hz,HG1″),7.17(1H,s,HG
4),7.25(4H,m,HG2,3,5,6);13CGNMR(100MHz,
641 广 西 植 物                  34卷
CD3OD)δ:18.0(CG6″),37.2(CGβ),68.1(CG6′),69.8(CG
5″),71.6(CGα),71.8(CG4′),72.1(CG2″),72.3(CG3″),
74.0(CG4″),75.0(CG2′),76.7(CG5′),78.0(CG3′),102.2
(CG1″),104.4(CG1′),127.2(CG4),129.3(CG3,5),130.0
(CG2,6),140.0(CG1)(Kaoruetal.,1988,Haseetal.,
1995).
Acknowledgements Theauthorsaregratefulto
Mr.NING DeGSheng(GuangxiKey Laboratoryof
FunctionalPhytochemicalsResearchandUtilization)
forNMRmeasurements.
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