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Chemical constituents of Incarvillea younghusbandii

藏波罗花的化学成分研究



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(5),heraclenol(6),rivulobirinA(7),
9—4J~
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:æ4J~
(9),
|;4
(10),boschniakinicacid(11),
tertOβDglucopyranosyl(R)heraclenol(12),5methoxy8OβDglucopyranosyloxypsoralen(13),1′OβDglucopyranosyl3
hydroxynodakenetin(14)
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IncarvileayounghusbandiSprague
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14(8
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15(28mg)。
3 
´µ4
G¥‰
1 
cK•
。ESIMSm/z217[M+
H]+,1HNMR(CDCl3,600MHz)δ:396(3H,s,
OCH3),629(1H,d,J=97Hz,H3),688(1H,s,
·85·
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35
Cu

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n

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Vol.35,Issue 1
January,2010
  
f
1 
G¥‰
1~7
Y
11~15
ƒ´µ
H6),701(1H,d,J=22Hz,H3′),756(1H,d,
J=22Hz,H2′),816(1H,d,J=97Hz,H4);
13CNMR(CDCl3,150MHz)δ:1609(C2),1122
(C3),1398(C4),1058(C4a),1542(C5),
905(C6),1579(C7),1101(C8),1488(C
8a),1443(C2′),1039(C3′),563(OCH3)。
#®ë^`B®

›]Fú
[4]
4‘G¥‰>
k4R5=~
(isobergapten)。
G¥‰
2 
cK•
。ESIMSm/z217[M+
H]+,1HNMR(CDCl3,600MHz)δ:404(3H,s,
OCH3),639(1H,d,J=96Hz,H3),678(1H,s,
H5),713(1H,d,J=20Hz,H3′),770(1H,d,
J=20Hz,H2′),776(1H,d,J=96Hz,H4)。
ë^`B®Ó
6
J=¨Å{Î
(sphondin)
ƒFú
{‹
[5]。
G¥‰
3 
cK•
。ESIMSm/z293[M+
Na]+,1HNMR(CDCl3,600MHz)δ:170,172
(each3H,s,2(CH3),500(2H,d,J=73Hz,H
1″),560(1H,m,H2″),635(1H,d,J=94Hz,
H3),680(1H,d,J=22Hz,H3′),735(1H,s,
H5),768(1H,d,J=22Hz,H2′),775(1H,d,
J=94Hz,H4);13CNMR(CDCl3,150MHz)δ:
1605(C2),1147(C3),1443(C4),1165(C
4a),1131(C5),1259(C6),1486(C7),
1317(C8),1438(C8a),1466(C2′),1067
(C3′),701(C1″),1198(C2″),1392(C3″),
258(CH3),180(CH3)。ë^`B®ÓbFV
Î
(imperatorin)
ƒFú{‹
[67]。
G¥‰
4 
cK•
。ESIMSm/z217[M+
H]+,1HNMR(CDCl3,600MHz)δ:430(3H,s,
OCH3),636(1H,d,J=97Hz,H3),682(1H,
d,J=22Hz,H3′),734(1H,s,H5),768(1H,
d,J=22Hz,H2′),775(1H,d,J=97Hz,H
4);13CNMR(CDCl3,150MHz)δ:1604(C2),
1145(C3),1443(C4),1165(C4a),1128
(C5),1261(C6),1477(C7),1329(C8),
1430(C8a),1466(C2′),1067(C3′),614
(OCH3)。ë^`B®ÓÁ6Þ=~(xanthotox
in)
ƒFú{‹
[67]。
G¥‰
5 
cK•
。ESIMSm/z323[M+
Na]+,1HNMR(CDCl3,600MHz)δ:170,174
(each3H,s,2(CH3),417(3H,s,OCH3),484
(2H,d,J=70Hz,H1″),560(1H,m,H2″),627
(1H,d,J=98Hz,H3),698(1H,d,J=22Hz,
H3′),762(1H,d,J=22Hz,H2′),810(1H,d,
J=98Hz,H4);13CNMR(CDCl3,150MHz)δ:
1605(C2),1128(C3),1394(C4),1076(C
4a),1445(C5),1146(C6),1508(C7),
1269(C8),1438(C8a),1451(C2′),1050
(C3′),704(C1″),1199(C2″),1394(C3″),
258(CH3),180(CH3),608(OCH3)。ë^
`B®Ó78Ê=~
(phelopterin)
ƒFú{
·95·
u
35
Cu

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2010
n

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Vol.35,Issue 1
January,2010
‹[8]。
G¥‰
6 
cK•
。ESIMSm/z327[M+
Na]+,1HNMR(CDCl3,600MHz)δ:132,136
(each3H,s,2×CH3),390(1H,dd,J=78,24,
H2″),475,443(each1H,dd,J=102;24Hz,J
=102,78Hz,H1″),639(1H,d,J=95Hz,H
3),685(1H,d,J=22Hz,H3′),742(1H,s,H
5),772(1H,d,J=22Hz,H2′),779(1H,d,J=
95Hz,H4);13CNMR (CDCl3,150MHz)δ:
1602(C2),1148(C3),1443(C4),1165(C
4a),1138(C5),1260(C6),1480(C7),
1316(C8),1433(C8a),1468(C2′),1069
(C3′),757(C1″),761(C2″),715(C3″),
251(CH3),266(CH3)。ë^`B®Ó hera
clenol
Fú{‹
[6]。
G¥‰
7 
cK•
。ESIMSm/z595[M+
Na]+,1HNMR(CDCl3,600MHz)δ:130(3H,s,
13CH3),136(3H,s,13CH3),183(3H,s,H
14″),398(1H,m,H12),437,438(each1H,m,
H11″),458(1H,m,H12″),443(1H,dd,J=
102,78Hz,H11b),473(1H,dd,J=102,24
Hz,H11a),500,516(each1H,s,H15″b,15″a),
629(1H,d,J=96Hz,H3″),631(1H,d,J=96
Hz,H3),674(1H,d,J=24Hz,H3″′),674
(1H,d,J=24Hz,H3′),727(1H,s,H5),727
(1H,s,H5″),762(1H,d,J=24Hz,H2″′),767
(1H,d,J=24Hz,H2′),768(1H,d,J=96Hz,
H4″),769(1H,d,J=96Hz,H4);13CNMR
(CDCl3,150MHz)δ:1603(C2,C2″),1602
(C2,C2″),1147(C3),1147(C3″),1447
(C4,C4″),1441(C4,C4″),1130(C5,C
5″),1136(C5,C5″),1260(C6,C6″),1259
(C6,C6″),1477(C7,C7″),1481(C7,C
7″),1320(C8),1320(C8″),1431(C9,C9″),
1434(C9,C9″),1164(C10),1164(C10″),
1467(C2′),1467(C2″′),1066(C3′),1066
(C3″′),752(C11),760(C11″),766(C12),
751(C12″),1451(C13″),781(C13),187
(C14″),1130(C15″),217(13CH3),228(13
CH3)。ë^`B®Ó rivulobirinAƒFú{
[9]
µ¥

G¥‰
8 
cK•
。ESIMSm/z471[M+
H]+,13CNMR(CDCl3,150MHz)δ:388(C1),
279(C2),791(C3),387(C4),556(C5),
186(C6),330(C7),395(C8),478(C9),
371(C10),234(C11),1223(C12),1446
(C13),418(C14),285(C15),235(C16),
465(C17),419(C18),462(C19),307(C
20),334(C21),318(C22),286(C23),163
(C24),153(C25),172(C26),259(C27),
1797(C28),330(C29),236(C30),533
(COOCH3)。{ë^`B®v 4>9—4
J~
(methyloleanolate)[10]
G¥‰
9 
÷ۍK•
。ESIMSm/z217
[M+Na]+,1HNMR(DMSOd6,600MHz)δ:373
(3H,s,OCH3),632(1H,d,J=159Hz,αCH=),
676(1H,d,J=81Hz,H5),705(1H,dd,J=
81,20Hz,H6),724(1H,d,J=20Hz,H2),
744(1H,d,J=159Hz,βCH=)。ë^`B®
Ó:æ4J~
(methylcafeate)
ƒFú{Ô[
[11]。
G¥‰
10 
ۍ@)
ESIMSm/z181[M+
H]+,1HNMR(DMSOd6,600MHz)δ:629(1H,
d,J=162Hz,Hα),673(1H,d,J=78Hz,H
3),682(1H,dd,J=18,78Hz,H4),694(1H,
d,J=18Hz,H6),721(1H,d,J=162Hz,H
β),908(1H,s,OH),931(1H,s,OH)。ë^`
B®Ó|;4
(grevilicacid)
ƒFú{‹
[12]。
G¥‰
11 
÷ۍK•
ESIMSm/z178[M+
H]+,1HNMR(DMSOd6,600MHz)δ:125(3H,
d,J=70Hz,CH3),160(1H,m),233(1H,m),
307(1H,m),325(2H,m),882(1H,s,H6),
858(1H,s,H2);13CNMR(DMSOd6,150MHz)
δ:1478(C2),1451(C3),1554(C4),1232
(C5),1492(C6),334(C7),322(C8),368
(C9),1674(C10),201(CH3)。ë^`B®
Ó
boschniakinicacid
ƒFú{‹
[13]。
G¥‰
12 
cK•
ESIMSm/z489[M+
Na]+,1HNMR(DMSOd6,600MHz)δ:121,123
(each3H,s,2(CH3),387(1H,m,H2″),439
(1H,m,H1″b),460(1H,dd,J=98,16Hz,H1″
a),642(1H,d,J=94Hz,H3),709(1H,d,J=
20Hz,H3′),766(1H,s,H5),811(1H,d,J=
20Hz,H2′),813(1H,d,J=94Hz,H4),440
(1H,d,J=77Hz,H1″′),290(1H,m,H2″′),
315(1H,m,H3″′),302(1H,m,H4″′),310
(1H,m,H5″′),360(1H,m,H6″′a),337(1H,
·06·
u
35
Cu

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2010
n

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Vol.35,Issue 1
January,2010
m,H6″′b);13CNMR(DMSOd6,150MHz)δ:
1603(C2),1146(C3),1458(C4),1169(C
4a),1141(C5),1263(C6),1476(C7),
1320(C8),1431(C8a),1482(C2′),1075
(C3′),771(C1″),772(C2″),786(C3″),
242(CH3),220(CH3),Glc:972(C1),741
(C2),756(C3),707(C4),756(C5),616
(C6)。
ë^`B®Ó
tertOβDglucopyranosyl
(R)heraclenol
ƒFú{
[14]


G¥‰
13 
X)•
ESIMSm/z417[M+
Na]+,1HNMR(DMSOd6,600MHz)δ:415(3H,
s,OCH3),632(1H,d,J=99Hz,H3),734(1H,
d,J=22Hz,H3′),804(1H,d,J=22Hz,H
2′),817(1H,d,J=99Hz,H4),Glc:535(1H,
d,J=69Hz,H1″),313~351(5H,m,H2″~H
6″)。
ë^`B®Ó
5methoxy8OβDglucopyr
anosyloxypsoralen
Fú{Ô[
[15]。
G¥‰
14 
cK•
ESIMSm/z447[M+
Na]+,1HNMR(DMSOd6,600MHz)δ:147(6H,
s,2′CH3),454(1H,d,J=63Hz,H2),525
(1H,d,J=66Hz,H3),768(1H,s,H4),801
(1H,d,J=95Hz,H5),626(1H,d,J=95Hz,
H6),692(1H,s,H9),453(1H,d,J=77Hz,
H1″),286(1H,m,H2″),314(1H,m,H3″),
304(1H,m,H4″),306(1H,m,H5″),334,338
(each1H,m,H6″),13CNMR(DMSOd6,150MHz)
δ:922(C2),779(C3),1290(C3a),1260
(C4),1122(C4a),1453(C5),1122(C6),
1608(C7),1565(C8a),977(C9),1628(C
9a),702(C1′),232,250(CH3),Glc:977
(C1),738(C2),770(C3),702(C4),773
(C5),612(C6)。
ë^`B®Ó
1′OβDglu
copyranosyl3hydroxynodakenetin
ƒFú{‹
[16]。
G¥‰
15 
cK•
ESIMSm/z469[M+
Na]+,1HNMR(DMSOd6,600MHz)δ:282(2H,
m,H7),363(1H,m,H8a),390(1H,dd,J=
82,160Hz,H8b),432(1H,d,J=77Hz,H
1″),439(1H,d,J=79Hz,H1′),716(1H,m,
H4),724(4H,d,J=47Hz,H2,3,5,6);13C
NMR(DMSOd6,150MHz)δ:1393(C1),1294
(C2),1286(C3),1264(C4),1280(C5),
1294(C6),360(C7),701(C8),Glc:1045
(C1),827(C2),771(C3),703(C4),766
(C5),614(C6),Glc:1018(C1′),753(C
2′),776(C3′),704(C4′),766(C5′),615
(C6′)。
ë^`B®Ó¯vf
OβD!”•
–
(1→2)OβD!”•–ï(phenylethylOβ
Dglucopyranosyl(1→2)βDglucopyranoside)ƒF
ú{Ô‹
[17]。

—˜™š

[1] 
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&,3
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S5

‚P
š0yí
,1991:463
[2] 
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GCMS
¤³
[J]
¤³/=`
,2008,27(
øa
):70
[3] PanWG,JiangSP,LuoP,etalIsolation,purificationand
structureidentificationofantioxidantcompoundfromtherootsof
IncarvileayounghusbandiSpragueanditslifespanprolonging
efectinDrosophilamelanogaster[J]NatProdRes,2008,22
(8):719
[4] 
GœŸ

iH

I$ˆ

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05;¡ƒç!Σ¤
[J]
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$,23
,1993,18(12):736
[5] 
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Õ_{®ƒG£¤/0
[J]´
>$-.`
,2003,26(26):14
[6] HarkarS,RazdanTK,WaightES.Steroids,chromoneand
coumarinsfromAngelicaoficinalis[J]Phytochemistry,1984,
23(2):419
[7] ElgamalMHA,ElewaNH,ElkhrisyEAM,etal13Cchemi
calshiftandcarbonprotoncouplingconstantsofsomefurocouma
rinsandfurochromones[J]Phytochemistry,1979,18:139
[8] 
v

¡Gé

æ˜d

ä

´cKG£¤/0
[J]

,
,2005,36(8):1132
[9] NiuXM,LiSH,JiangB,etalConstituentsfromtherootsof
HeracleumrapulaFranch[J]JAsianNatProdRes,2002,4
(1):33
[10] 
©cë

oPá

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,1999
[11] 
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P>°þáùýG£¤/0
[J]
$%,23
,2005,40(12):893
[13] NicolasR,ChristopheH,FrancisM.Neattotalsynthesisofsix
monoterpenicalkaloidsoftheactinidineseries[J]Tetrahedron,
2007,63:3702
[14] ThastrupO,LemmichJ.FurocoumaringlucosidesofAngelica
archangelicasubspecieslitoralis[J]Phytochemistry,1983,22
(9):2035
[15] AhluwaliaVK,BoydDR,JainKA,etalFuranocoumarin
glucosidesfromtheseedofApiumgraveolens[J]Phytochemis
try,1988,27(4):1181
[16] 
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·16·
u
35
Cu

w
2010
n

o
                             
Vol.35,Issue 1
January,2010
ChemicalconstituentsofIncarvileayounghusbandi
FUYu1,BAIYang2,DAWAZhuoma2,BAIBingru1,DINGLisheng1
(1ChengduInstituteofBiology,ChineseAcademyofSciences,Chengdu610041,China;
2TibetAutonomousRegionInstituteforFoodandDrugControl,Lhasa850000,China)
[Abstract] Objective:TostudythechemicalconstituentsofIncarvileayounghusbandiMethod:Thechemicalconstituents
wereisolatedbyvariouscolumnchromatographicmethodsandstructuralyidentifiedbyNMRandMSevidenceResult:Fifteencom
poundswereobtainedandidentifiedasisobergapten(1),sphondin(2),imperatorin(3),xanthotoxin(4),phelopterin(5),hera
clenol(6),rivulobirinA(7),methyloleanolate(8),methylcafeate(9),grevilicacid(10),boschniakinicacid(11),tertOβ
Dglucopyranosyl(R)heraclenol (12), 5methoxy8OβDglucopyranosyloxypsoralen (13), 1′OβDglucopyranosyl3
hydroxynodakenetin(14)andphenylethylOβDglucopyranosyl(1→2)βDglucopyranoside(15)Conclusion:Alofthesecom
poundswereisolatedfromthisplantforthefirsttimeandmostofthemarefurocoumarins
[Keywords] Incarvileayounghusbandi;chemicalconstituent;furocoumarin
doi:10.4268/cjcmm20100112

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Vol.35,Issue 1
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