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2010
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905(C6),1579(C7),1101(C8),1488(C
8a),1443(C2′),1039(C3′),563(OCH3)。
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2
cK
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H]+,1HNMR(CDCl3,600MHz)δ:404(3H,s,
OCH3),639(1H,d,J=96Hz,H3),678(1H,s,
H5),713(1H,d,J=20Hz,H3′),770(1H,d,
J=20Hz,H2′),776(1H,d,J=96Hz,H4)。
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6
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(sphondin)
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[5]。
G¥
3
cK
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Na]+,1HNMR(CDCl3,600MHz)δ:170,172
(each3H,s,2(CH3),500(2H,d,J=73Hz,H
1″),560(1H,m,H2″),635(1H,d,J=94Hz,
H3),680(1H,d,J=22Hz,H3′),735(1H,s,
H5),768(1H,d,J=22Hz,H2′),775(1H,d,
J=94Hz,H4);13CNMR(CDCl3,150MHz)δ:
1605(C2),1147(C3),1443(C4),1165(C
4a),1131(C5),1259(C6),1486(C7),
1317(C8),1438(C8a),1466(C2′),1067
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258(CH3),180(CH3)。ë^`B®ÓbFV
Î
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[67]。
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4
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H]+,1HNMR(CDCl3,600MHz)δ:430(3H,s,
OCH3),636(1H,d,J=97Hz,H3),682(1H,
d,J=22Hz,H3′),734(1H,s,H5),768(1H,
d,J=22Hz,H2′),775(1H,d,J=97Hz,H
4);13CNMR(CDCl3,150MHz)δ:1604(C2),
1145(C3),1443(C4),1165(C4a),1128
(C5),1261(C6),1477(C7),1329(C8),
1430(C8a),1466(C2′),1067(C3′),614
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Na]+,1HNMR(CDCl3,600MHz)δ:170,174
(each3H,s,2(CH3),417(3H,s,OCH3),484
(2H,d,J=70Hz,H1″),560(1H,m,H2″),627
(1H,d,J=98Hz,H3),698(1H,d,J=22Hz,
H3′),762(1H,d,J=22Hz,H2′),810(1H,d,
J=98Hz,H4);13CNMR(CDCl3,150MHz)δ:
1605(C2),1128(C3),1394(C4),1076(C
4a),1445(C5),1146(C6),1508(C7),
1269(C8),1438(C8a),1451(C2′),1050
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·95·
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n
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Vol.35,Issue 1
January,2010
[8]。
G¥
6
cK
。ESIMSm/z327[M+
Na]+,1HNMR(CDCl3,600MHz)δ:132,136
(each3H,s,2×CH3),390(1H,dd,J=78,24,
H2″),475,443(each1H,dd,J=102;24Hz,J
=102,78Hz,H1″),639(1H,d,J=95Hz,H
3),685(1H,d,J=22Hz,H3′),742(1H,s,H
5),772(1H,d,J=22Hz,H2′),779(1H,d,J=
95Hz,H4);13CNMR (CDCl3,150MHz)δ:
1602(C2),1148(C3),1443(C4),1165(C
4a),1138(C5),1260(C6),1480(C7),
1316(C8),1433(C8a),1468(C2′),1069
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251(CH3),266(CH3)。ë^`B®Ó hera
clenol
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G¥
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13CH3),136(3H,s,13CH3),183(3H,s,H
14″),398(1H,m,H12),437,438(each1H,m,
H11″),458(1H,m,H12″),443(1H,dd,J=
102,78Hz,H11b),473(1H,dd,J=102,24
Hz,H11a),500,516(each1H,s,H15″b,15″a),
629(1H,d,J=96Hz,H3″),631(1H,d,J=96
Hz,H3),674(1H,d,J=24Hz,H3″′),674
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(1H,d,J=24Hz,H2′),768(1H,d,J=96Hz,
H4″),769(1H,d,J=96Hz,H4);13CNMR
(CDCl3,150MHz)δ:1603(C2,C2″),1602
(C2,C2″),1147(C3),1147(C3″),1447
(C4,C4″),1441(C4,C4″),1130(C5,C
5″),1136(C5,C5″),1260(C6,C6″),1259
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7″),1320(C8),1320(C8″),1431(C9,C9″),
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8
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279(C2),791(C3),387(C4),556(C5),
186(C6),330(C7),395(C8),478(C9),
371(C10),234(C11),1223(C12),1446
(C13),418(C14),285(C15),235(C16),
465(C17),419(C18),462(C19),307(C
20),334(C21),318(C22),286(C23),163
(C24),153(C25),172(C26),259(C27),
1797(C28),330(C29),236(C30),533
(COOCH3)。{ë^`B®v 4>94
J~
(methyloleanolate)[10]
G¥
9
÷ÛK
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[M+Na]+,1HNMR(DMSOd6,600MHz)δ:373
(3H,s,OCH3),632(1H,d,J=159Hz,αCH=),
676(1H,d,J=81Hz,H5),705(1H,dd,J=
81,20Hz,H6),724(1H,d,J=20Hz,H2),
744(1H,d,J=159Hz,βCH=)。ë^`B®
Ó:æ4J~
(methylcafeate)
Fú{Ô[
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G¥
10
Û@)
ESIMSm/z181[M+
H]+,1HNMR(DMSOd6,600MHz)δ:629(1H,
d,J=162Hz,Hα),673(1H,d,J=78Hz,H
3),682(1H,dd,J=18,78Hz,H4),694(1H,
d,J=18Hz,H6),721(1H,d,J=162Hz,H
β),908(1H,s,OH),931(1H,s,OH)。ë^`
B®Ó|;4
(grevilicacid)
Fú{
[12]。
G¥
11
÷ÛK
ESIMSm/z178[M+
H]+,1HNMR(DMSOd6,600MHz)δ:125(3H,
d,J=70Hz,CH3),160(1H,m),233(1H,m),
307(1H,m),325(2H,m),882(1H,s,H6),
858(1H,s,H2);13CNMR(DMSOd6,150MHz)
δ:1478(C2),1451(C3),1554(C4),1232
(C5),1492(C6),334(C7),322(C8),368
(C9),1674(C10),201(CH3)。ë^`B®
Ó
boschniakinicacid
Fú{
[13]。
G¥
12
cK
ESIMSm/z489[M+
Na]+,1HNMR(DMSOd6,600MHz)δ:121,123
(each3H,s,2(CH3),387(1H,m,H2″),439
(1H,m,H1″b),460(1H,dd,J=98,16Hz,H1″
a),642(1H,d,J=94Hz,H3),709(1H,d,J=
20Hz,H3′),766(1H,s,H5),811(1H,d,J=
20Hz,H2′),813(1H,d,J=94Hz,H4),440
(1H,d,J=77Hz,H1″′),290(1H,m,H2″′),
315(1H,m,H3″′),302(1H,m,H4″′),310
(1H,m,H5″′),360(1H,m,H6″′a),337(1H,
·06·
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Vol.35,Issue 1
January,2010
m,H6″′b);13CNMR(DMSOd6,150MHz)δ:
1603(C2),1146(C3),1458(C4),1169(C
4a),1141(C5),1263(C6),1476(C7),
1320(C8),1431(C8a),1482(C2′),1075
(C3′),771(C1″),772(C2″),786(C3″),
242(CH3),220(CH3),Glc:972(C1),741
(C2),756(C3),707(C4),756(C5),616
(C6)。
ë^`B®Ó
tertOβDglucopyranosyl
(R)heraclenol
Fú{
[14]
。
G¥
13
X)
ESIMSm/z417[M+
Na]+,1HNMR(DMSOd6,600MHz)δ:415(3H,
s,OCH3),632(1H,d,J=99Hz,H3),734(1H,
d,J=22Hz,H3′),804(1H,d,J=22Hz,H
2′),817(1H,d,J=99Hz,H4),Glc:535(1H,
d,J=69Hz,H1″),313~351(5H,m,H2″~H
6″)。
ë^`B®Ó
5methoxy8OβDglucopyr
anosyloxypsoralen
Fú{Ô[
[15]。
G¥
14
cK
ESIMSm/z447[M+
Na]+,1HNMR(DMSOd6,600MHz)δ:147(6H,
s,2′CH3),454(1H,d,J=63Hz,H2),525
(1H,d,J=66Hz,H3),768(1H,s,H4),801
(1H,d,J=95Hz,H5),626(1H,d,J=95Hz,
H6),692(1H,s,H9),453(1H,d,J=77Hz,
H1″),286(1H,m,H2″),314(1H,m,H3″),
304(1H,m,H4″),306(1H,m,H5″),334,338
(each1H,m,H6″),13CNMR(DMSOd6,150MHz)
δ:922(C2),779(C3),1290(C3a),1260
(C4),1122(C4a),1453(C5),1122(C6),
1608(C7),1565(C8a),977(C9),1628(C
9a),702(C1′),232,250(CH3),Glc:977
(C1),738(C2),770(C3),702(C4),773
(C5),612(C6)。
ë^`B®Ó
1′OβDglu
copyranosyl3hydroxynodakenetin
Fú{
[16]。
G¥
15
cK
ESIMSm/z469[M+
Na]+,1HNMR(DMSOd6,600MHz)δ:282(2H,
m,H7),363(1H,m,H8a),390(1H,dd,J=
82,160Hz,H8b),432(1H,d,J=77Hz,H
1″),439(1H,d,J=79Hz,H1′),716(1H,m,
H4),724(4H,d,J=47Hz,H2,3,5,6);13C
NMR(DMSOd6,150MHz)δ:1393(C1),1294
(C2),1286(C3),1264(C4),1280(C5),
1294(C6),360(C7),701(C8),Glc:1045
(C1),827(C2),771(C3),703(C4),766
(C5),614(C6),Glc:1018(C1′),753(C
2′),776(C3′),704(C4′),766(C5′),615
(C6′)。
ë^`B®Ó¯vf
OβD!
(1→2)OβD!ï(phenylethylOβ
Dglucopyranosyl(1→2)βDglucopyranoside)F
ú{Ô
[17]。
[
]
[1]
$%&.S7K/01
&,3
[M]
S5
:
P
0yí
,1991:463
[2]
mE
,
#ì
,
cF
,
ä
S&ýÁ¾b÷
GCMS
¤³
[J]
¤³/=`
,2008,27(
øa
):70
[3] PanWG,JiangSP,LuoP,etalIsolation,purificationand
structureidentificationofantioxidantcompoundfromtherootsof
IncarvileayounghusbandiSpragueanditslifespanprolonging
efectinDrosophilamelanogaster[J]NatProdRes,2008,22
(8):719
[4]
G
,
iH
,
I$
,
ä
05;¡ç!Σ¤
[J]
$%
$,23
,1993,18(12):736
[5]
J
,
ð3(
,
õê
,
ä
Õ_{®G£¤/0
[J]´
>$-.`
,2003,26(26):14
[6] HarkarS,RazdanTK,WaightES.Steroids,chromoneand
coumarinsfromAngelicaoficinalis[J]Phytochemistry,1984,
23(2):419
[7] ElgamalMHA,ElewaNH,ElkhrisyEAM,etal13Cchemi
calshiftandcarbonprotoncouplingconstantsofsomefurocouma
rinsandfurochromones[J]Phytochemistry,1979,18:139
[8]
v
,
¡Gé
,
æd
,
ä
´cKG£¤/0
[J]
$ö
,
,2005,36(8):1132
[9] NiuXM,LiSH,JiangB,etalConstituentsfromtherootsof
HeracleumrapulaFranch[J]JAsianNatProdRes,2002,4
(1):33
[10]
©cë
,
oPá
¤³GRû
[M]
78
:
Gqªy
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,1999
[11]
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[12]
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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,etalFuranocoumarin
glucosidesfromtheseedofApiumgraveolens[J]Phytochemis
try,1988,27(4):1181
[16]
!0
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·16·
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Cu
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n
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Vol.35,Issue 1
January,2010
ChemicalconstituentsofIncarvileayounghusbandi
FUYu1,BAIYang2,DAWAZhuoma2,BAIBingru1,DINGLisheng1
(1ChengduInstituteofBiology,ChineseAcademyofSciences,Chengdu610041,China;
2TibetAutonomousRegionInstituteforFoodandDrugControl,Lhasa850000,China)
[Abstract] Objective:TostudythechemicalconstituentsofIncarvileayounghusbandiMethod:Thechemicalconstituents
wereisolatedbyvariouscolumnchromatographicmethodsandstructuralyidentifiedbyNMRandMSevidenceResult:Fifteencom
poundswereobtainedandidentifiedasisobergapten(1),sphondin(2),imperatorin(3),xanthotoxin(4),phelopterin(5),hera
clenol(6),rivulobirinA(7),methyloleanolate(8),methylcafeate(9),grevilicacid(10),boschniakinicacid(11),tertOβ
Dglucopyranosyl(R)heraclenol (12), 5methoxy8OβDglucopyranosyloxypsoralen (13), 1′OβDglucopyranosyl3
hydroxynodakenetin(14)andphenylethylOβDglucopyranosyl(1→2)βDglucopyranoside(15)Conclusion:Alofthesecom
poundswereisolatedfromthisplantforthefirsttimeandmostofthemarefurocoumarins
[Keywords] Incarvileayounghusbandi;chemicalconstituent;furocoumarin
doi:10.4268/cjcmm20100112
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、
öN
、
VäVNä5
。
¹
º
:
:7
、
JF
、
Wýd
(
M:NR
)。
NRm9Ê
。
»`¼q
:
#Æ,
。
`½O¾
:
o
,
ò6
。
¡rfX
,
Y:G
,
m
,
¿À
。
â%ÇÀ
、
:÷®À
、
Z[
、
þÀ?°ä
。
û]
,
!
10~15g。
·26·
u
35
Cu
1
w
2010
n
1
o
Vol.35,Issue 1
January,2010