金鱼藻实验

金鱼藻的化学成分

路小利1,2,乔英2,张宪民2,马柏林1,邱明华2

(1西北农林科技大学生命科学学院,陕西杨陵712100;2中国科学院昆明植物研究所植物化学与

西部植物资源持续利用国家重点实验室,云南昆明650204)

摘要:从金鱼藻(CeratophyllumdemersumL.)全草的乙醇提取物中分离鉴定了其中7个,分别为:苜蓿素-

7-O-β-D-葡萄糖苷(1),naringenin-7-O-β-D-葡萄糖苷(2,七叶内酯(3),β-谷甾醇(4,7α-羟基-β-谷甾

醇(5),7α-甲氧基-β-谷甾醇(6),十六碳脂肪酸(7)。化合物(3)为首次从金鱼藻中分离得到。

关键词:金鱼藻;苜蓿素-7-O-β-D-葡萄糖苷;Naringenin-7-O-β-D-葡萄糖苷;七叶内酯

中图分类号:Q946文献标识码:A文章编号:0253-2700(2007)02-263-02

ChemicalConstituentsfromCeratophyllum

demersum(Ceratophyllaceae)

LUXiao-Li1,2,QIAOYing2,ZHANGXian-Min2,MABo-Lin1,QIUMing-Hua2*

(1CollegeofLifeScienceofNorthwestSci-TechUniversityofAgriculturalandForestry,Yangling712100,China;

2TheStateKeyLaboratoryofPhytochemistryandPlantResourcesinWestChina,KunmingInstitute

ofBotany,ChineAcademyofSciences,Kunming650204,China)

Abstract:Inthispaper,wereprentvencompounds[tricin-7-O-β-D-glucoside(1),naringenin-7-O-β-D-glucoside

(2),esculetin(3),β-sitosterol(4),7α-hydroxyl-β-sitosterol(5),7α-methoxyl-β-sitosterol(6)andpalmiticacid(7)].

arethemwith

ultsshowthatthetypesofmaincondary

anaresimilar.

Keywords:Ceratophyllumdemersum;Tricin-7-O-β-D-glucoside;Naringenin-7-O-β-D-glucoside;Esculetin

CeratophyllumdemersumL.(Ceratophyllaceae),

isakindofperennialhydrophilyplantandwidelydis-

y

itwasudasgoldfishfeed,aswellasfolkmedicine

forthetreatmentsofinternalinjuryandhaematemesis

(Wuetal.2003).Foreignscholarshavealreadyiso-

latedtwocompoundsofflavonoidandvenkindsof

Phytosterol(Bankovaetal.1995);however,the

chemicalconstituentsofCeratophyllumdemersumL.

osystem-

aticallystudyonchemicalconstituentsoftheplantsand

provideaccessorialevidencetodeterminethesystemati-

aper,the

chemicalstructuresofvencompoundsfromabove

mentionedplantwouldbereported.

Experimental

GeneralMeltingpointsweremeasuredonaWC-1micro

meltingpointsapparatusandareuncorrected.1HNMR,13C

NMRand2D-NMRspectrawererecordedonaBrukerAM-400

MHzandaDRX-500spectrometerwithTMSasinternalstan-

-MS:Autospec-3000spectrometer(inz);Silica

gel(200-300mesh)wasproducedbyQingdaoMarineChemical

-18(40-60μ,Merck).SephadexLH-20(Amer-

shamPharmaciaBiotechAB).

collectedinLijiang,YunnanProvince,2005.

云南植物研究2007,29(2):263～264

ActaBotanicaYunnanica

Foundationitem:XiBuZhiGuangProgramofChineAcademyofSciencesforfinancialsupport.

Correspondingauthor,Tel:+86-871-5223327;Fax:+86-871-5223255;E-mail:mhchiu@

Receiveddate:2006-07-11;Accepteddate:2006-08-10接受发表

作者简介:路小利(1982-)女,在读硕士研究生,主要从事植物化学研究。

*

*

**

**

**

(1)

(2)(3)

(4)

(5)(6)(7)

(3)

ChemicalConstituentsfromCeratophyllum

demersum(Ceratophyllaceae)

Abstract:

Keywords:

(1)

(2)

(3)

(4)(5)

(6)

(7)

General

PlantMaterial

m/z

xian(Kunming

InstituteofBotany,theChineAcademyofSciences),anda

voucherspecimenwasdepositedattheLaboratoryofPhytochem-

istry,KunmingInstituteofBotany.

ExtractionandIsolationDriedchippedCeratophyllum

demersumL.(5kg)ractwas

filtered,concentratedinvacuotoasuitablevolume,suspended

inwater,andthensuccessivelypartitionedwithPetroleumEther,

CHCl

3

,andEtOAc,hreeextractswerere-

spectivelyconcentratedinvacuotoaffordresiduesofPetroleum

Ether(62g),residuesofCHCl

3

(25g)andresiduesofEtOAc

(11g).

TheEtOAcportionwassubjectedrepeatedlytosilicagel

chromatographyandstepwilyelutedwithCHCl3-Me2CO(from

CHCl

3

toCHCl

3

-Me

2

CO1∶1)toyieldtricin-7-O-β-D-glucoside

(1)(10mg),Naringenin-7-O-β-D-glucoside(2)(7mg)and

esculetin(3)(7mg),respectively.

TheCHCl3portionwassubjectedrepeatedlytosilicagel

chromatographyandstepwilyelutedwithCHCl3-Me2CO(from

CHCl

3

toCHCl

3

-Me

2

CO1∶1)toyieldβ-sitosterol(4)(10mg),

7α-hydroxyl-β-sitosterol(5(9mg),7α-methoxyl-β-sitosterol

(6)(7mg),palmiticacid(7)(12mg),respectively.

StructuralIdentification

Tricin-7-O-β-D-glucoside(1),C23H24O12,yellowpow-

260.5-261℃(MeOH).1HNMR(400MHz,DM-

SO):6.44(1H,s,H-3),6.95(1H,s,H-6),7.04

(1H,s,H-8),7.34(2H,s,H-2′,6′),3.87(6H,s,

OMe),4.69(1H,d,H-1″),3.72-3.15(6H,m,H-

2″,3″,4″,5″,6″).13CNMR(125MHz,DMSO):164.3

(C-2),103.8(C-3),182.1(C-4),161.1(C-5),99.6

(C-6),163.1(C-7),95.4(C-8),105.5(C-9),157.0

(C-10),120.3(C-1′),104.6(C-2′,6′),148.3(C-

3′,5′),140.2(C-4′),100.2(C-1″),73.2(C-2″),

76.5(C-3″),69.8(C-4″),77.4(C-5″),60.8(C-6″),

56.5(3′,5′-OMe).(.1978).

Naringenin-7-O-β-D-glucoside(2),C

21

H

22

O

10

,mp225℃.

1HNMR(400MHz,CD3OD):2.72(1H,H-3,d,J=12.3

Hz),3.13(1H,H-3,d,J=12.3Hz),3.15-3.50(4H,

m,H-2″,3″,4″,5″),3.62(1H,H-6″,d,J=11.9

Hz),3.70(1H,H-6″,d,J=11.9Hz),5.40(1H,H-

2,brs),6.18(1H,H-8,s),6.20(1H,H-6,s),

4.96(1H,H-1″,d,J=4.3Hz),6.80(2H,H-3′and

H-5′,d,J=7.5Hz),7.31(2H,H-2′andH-4′d,J

=7.5Hz);13CNMR(125MHz,CD

3

OD):80.6(C-2),

42.4(C-3),198.5(C-4),167.0(C-5),98.1(C-6),

164.6(C-7),96.9(C-8),164.0(C-9),116.4(C-

10),130.9(C-1′),129.1(C-2′,6′),116.4(C-3′,

5′),159.1(C-4′),101.3(C-1″),74.7(C-2″),78.3

(C-3″),71.2(C-4″),77.9(C-5″),62.4(C-6″).

Esculetin(3),C

9

H

6

O

4

,yellowcrystal,mp285-286℃

(EtOH).1HNMR(400MHz,DMSO):6.11(1H,d,J=

9.5Hz,H-3),7.77(d,J=9.5Hz,H-4),6.99(1H,

s,H-5),6.76(1H,s,H-8).13CNMR(125MHz,DM-

SO):161.5(C-2),112.5(C-3),144.7(C-4),112.9(C

-5),143.9(C-6),151.4(C-7),103.4(C-8),149.8(C

-9),111.8(C-10).(.1975).

Sevenknowncompoundswhichwereisolatedfrom

tedinLijangCounty

ofYunnanprovince,werecomparedthemwiththe

t-

ultsshownthatthe

compoundsofmaincondarymetabolitefromCerato-

tedindifferentplaceof

Yunnanwereverysimilar.

References:

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giosperms[M].Beijing:SciencePress,87—89

SuoZL,eneticReviewofceratophyllaceae[J].ActaBot

Boreal-OccidentSin,25(5):1058—1063

BankovaV,IvanovaP,arymetabolitesof

Ceratophyllumdemersum[J].Hydrobiologia,316(1):59—61

CussansNJ,HuckerbyTN,-13NMRspectroscopyofhet-

erocycliccompound-IV[J].Tetrahedron,31:2719—2726

PettitGR,NumataA,CraggGM,ionandstructuresof

schleicherastatins1-7andschleicheols1and2fromtheteakforest

medicinaltreeSchleicheraoleosa[J].JNatProd,63:75—77

RamachanderG,BapatlaKR,EmeleJF,ferencesinplas-

mahalf-lifeofdextrorphaninratsadministereddextromethorphan

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isolatedfromtherootsofspatholobus[J].PlantaMed,54(1):

34—36

462云南植物研究29卷

ExtractionandIsolation

StructuralIdentification

(1)(2)

(3)

(4)

(5)

(6)

(7)

(1

(2)

(3)

Discussion

316

31

63

67

References: