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Vol41,No.5 March,2016
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isoestin7OβDglucopyr
anosyl2′OαLarabinopyranoside(1)、isoetin7OβDglucopyranosyl2′OβDxyloypyranoside(2)、isoetin7OβDglucopyranosyl
2′OαDglucopyranoside(3)、isoetin5′OβDglucopyranoside(4)、isoetin2′OβDxyloypyranoside(5)、isoetin4′OβDOβD
glucopyranoside(6)、isoetin7OβDglucopyranoside(7)、isoestin2′OαLarabinopyranoside(8)、ÀTì7OβDûügÄ
(9)、isoetin(10)
ÀTì
(11)。
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FlavonoidsfromPicrisdavurica
CHENQiao1,GUONa1,XUNan1,BAOGuihua2,Namujila2
(1Schoolofpharmacy,LiaoningUniversityofTraditionalChineseMedicine,Dalian116600,China;
2Schoolofpharmacy,InnerMongoliaUniversityfortheNationality,Tongliao028000,China)
[Abstract] ElevencompoundswerepurifiedfromtheantiinflammatoryextractofPicrisdavuricabycolumnchromatographonHP20
macroporousresin,MCI,sephadexLH20andODSTheirstructuresweredeterminedbythespectradataofNMRandMSasisoestin
7OβDglucopyranosyl2′OαLarabinopyranoside(1),isoetin7OβDglucopyranosyl2′OβDxyloypyranoside(2),isoetin7O
βDglucopyranosyl2′OαDglucopyranoside(3),isoetin5′OβDglucopyranoside(4),isoetin2′OβDxyloypyranoside(5),
isoetin4′OβDOβDglucopyranoside(6),isoetin7OβDglucopyranoside(7),isoestin2′OαLarabinopyranoside(8),luteo
lin7OβDglucopyranosie(9),isoetin(10)andluteolin(11)AlcompoundswereisolatedfromthisplantforthefirsttimeAmong
them,compounds18wereisolatedfromthegenusPicrisforthefirsttime
[Keywords] Picrisdavurica;chemicalconstituents;flavoneglucoside;isoetin
doi:10.4268/cjcmm20160517
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(276mg),9(119mg),10(155mg),11(232
mg)。
3
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1
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d»
U%βfÂ
。
ESIMSm/z597[M+H]+;1HNMR(DMSOd6,600
MHz)δ:1311(1H,brs,5OH),731(1H,s,H6′),
716(1H,s,H3),677(1H,s,H3′),672(1H,s,
H8),644(1H,s,H6),508(1H,d,J=80Hz,H
1′),487(1H,d,J=60Hz,H1″),320~360
(11H,m,H2″~ H6″,H2~H5);13CNMR
(DMSOd6,150MHz)δ:1618(C2),1089(C3),
1824(C4),1614(C5),996(C6),1631(C7),
944(C8),1579(C9),1054(C10),1106(C
1′),1504(C2′),1044(C3′),1504(C4′),
1406(C5′),1148(C6′),1000(C1″),733(C
2″),766(C3″),697(C4″),773(C5″),608(C
6″),1018(C1),725(C2),707(C3),673
(C4),654(C5)。¼Á=ª^kB£4[
Q
[7],
ÝÒ×µ_ñ.
1
¯
isoestin7OβDgluco
pyranosyl2′OαLarabinopyranoside。
_ñ.
2
Û>%¥
,
d»
U%βfÂ
。
ESIMSm/z597[M+H]+;1HNMR(DMSOd6,600
MHz)δ:1311(1H,brs,5OH),730(1H,s,H6′),
708(1H,s,H3),673(1H,s,H3′),673(1H,s,
H8),644(1H,s,H6),507(1H,d,J=72Hz,
H1′),489(1H,d,J=64Hz,H1″),320~360
(11H,m,H2″~H6″,H2~H5);13CNMR
(DMSOd6,150MHz)δ:1618(C2),1089(C3),
1822(C4),1613(C5),995(C6),1630(C7),
947(C8),1573(C9),1047(C10),1108(C
1′),1502(C2′),1054(C3′),1503(C4′),
1406(C5′),1148(C6′),1000(C1″),733(C
·568·
2016
y
3
z ©
41
ª©
5
}
Vol41,No.5 March,2016
2″),765(C3″),697(C4″),773(C5″),608(C
6″),1023(C1),733(C2),766(C3),695
(C4),659(C5)。¼Á=ª^kB£4[
Q
[7],
ÝÒ×µ_ñ.
2¯ isoetin7OβDglucopyr
anosyl2′OβDxyloypyranoside。
_ñ.
3
Û>%¥
,
d»
U%βfÂ
。
ESIMSm/z627[M+H]+;1HNMR(DMSOd6,600
MHz)δ:1307(1H,brs,5OH),731(1H,s,H6′),
711(1H,s,H3),680(1H,s,H3′),672(1H,s,
H8),645(1H,s,H6),508(1H,d,J=80Hz,H
1′),491(1H,brs,H1″),320~360(12H,m,
H2″~H6″,H2~H6);13CNMR(DMSOd6,150
MHz)δ:1618(C2),1089(C3),1822(C4),
1614(C5),995(C6),1630(C7),947(C8),
1572(C9),1054(C10),1104(C1′),1504(C
2′),1047(C3′),1054(C4′),1405(C5′),
1147(C6′),1001(C1″),733(C2″),765(C
3″),697(C4″),773(C5″),608(C6″),1013
(C1),735(C2),769(C3),697(C4),
773(C5),608(C6)。¼Á=ª^kB£
4[Q
[7],
ÝÒ×µ_ñ.
3¯ isoetin7OβDglu
copyranosyl2′OαDglucopyranoside。
_ñ.
4
Û>%¥
,
d»
U%βfÂ
。
ESIMSm/z465[M+H]+;1HNMR(DMSOd6,600
Hz)δ:1123(1H,brs,5OH),736(1H,brs,H
6′),703(1H,s,H3),675(1H,brs,H3′),649
(1H,s,H8),615(1H,s,H6),466(1H,d,J=70
Hz,H1′),316~357(6H,m,H2″~H6″);13C
NMR(DMSOd6,150MHz)δ:1614(C2),1072
(C3),1820(C4),1610(C5),986(C6),1639
(C7),942(C8),1575(C9),1036(C10),
1077(C1′),1517(C2′),1043(C3′),1540(C
4′),1393(C5′),1164(C6′),1032(C1″),733
(C2″),757(C3″),698(C4″),771(C5″),609
(C6″)。
¼Á=ª^kB£4[Q
[8],
ÝÒ×
µ_ñ.
4¯ isoetin5′OβDglucopyranoside。
_ñ.
5
Û>%¥
,
d»
U%βfÂ
。
ESIMSm/z435[M+H]+;1HNMR(DMSOd6,600
MHz)δ:1310(1H,s,5OH),728(1H,s,H6′),
701(1H,s,H3),673(1H,s,H3′),639(1H,d,
J=20Hz,H8),617(1H,d,J=20Hz,H6),
484(1H,d,J=64Hz,H1′),319377(5H,m,
H2′~H5′);13CNMR(DMSOd6,150MHz) δ:
1614(C2),1084(C3),1818(C4),1614(C
5),985(C6),1639(C7),935(C8),1573(C
9),1035(C10),1106(C1′),1498(C2′),1043
(C3′),1498(C4′),1405(C5′),1142(C6′),
1020(C1″),731(C2″),764(C3″),692(C
4″),657(C5″)。
¼Á=ª^kB£4[
Q
[8],
ÝÒ×µ_ñ.
5
¯
isoetin2′OβDxyloy
pyranoside。
_ñ.
6
Û>%¥
,
d»
U%βfÂ
。
ESIMSm/z465[M+H]+;1HNMR(DMSOd6,600
MHz)δ:1310(1H,s,5OH),732(1H,s,H6′),
705(1H,s,H3),679(1H,s,H3′),617(1H,d,
J=20Hz,H6),643(1H,d,J=20Hz,H8),
478(1H,d,J=76Hz,H1′),319~368(6H,m,
H2″~H6″);13CNMR(DMSOd6,150MHz) δ:
1614(C2),1078(C3),1818(C4),1611(C
5),986(C6),1640(C7),937(C8),1573(C
9),1036(C10),1100(C1′),1509(C2′),1046
(C3′),1489(C4′),1395(C5′),1137(C6′),
1012(C1″),731(C2″),759(C3″),692(C
4″),771(C5″),603(C6″)。
¼Á=ª^k
B£4[Q
[8],
ÝÒ×µ_ñ.
6¯ isoetin4′Oβ
Dglucopyranoside。
_ñ.
7
Û>%¥
,
d»
U%βfÂ
。
ESIMSm/z465[M+H]+;1HNMR(DMSOd6,600
MHz)δ:1310(1H,s,5OH),728(1H,s,H6′),
708(1H,s,H3),682(1H,s,H3′),671(1H,d,
J=19Hz,H8),640(1H,d,J=19Hz,H6),
507(1H,d,J=74Hz,H1′),320~350(6H,m,
H2″~H6″),370(1H,brd,J=100Hz,H5′);
13CNMR(DMSOd6,150MHz)δ:1620(C2),
1068(C3),1820(C4),1610(C5),998(C6),
1627(C7),944(C8),1570(C9),1039(C
10),1100(C1′),1500(C2′),1049(C3′),
1490(C4′),1390(C5′),1140(C6′),1010
(C1″),731(C2″),763(C3″),694(C4″),771
(C5″),605(C6″)。
¼Á=ª^kB£4[
Q
[9],
ÝÒ×µ_ñ.
7¯ isoetin7OβDglucopyr
anoside。
_ñ.
8
Û>%¥
,
d»
U%βfÂ
。
ESIMSm/z597[M+H]+;1HNMR(DMSOd6,600
·668·
¨
:
45678Û9
MHz)δ:1311(1H,brs,5OH),731(1H,s,H6′),
716(1H,s,H3),677(1H,s,H3′),672(1H,s,
H8),644(1H,s,H6),508(1H,d,J=80Hz,
H1′),487(1H,d,J=60Hz,H1″),320~360
(5H,m,H2′~H5′),320~360(5H,m,H2″~
H5″);13CNMR(DMSOd6,150MHz)δ:1618(C
2),1088(C3),1823(C4),1614(C5),996(C
6),1645(C7),941(C8),1578(C9),1045(C
10),1108(C1′),1504(C2′),1040(C3′),
1504(C4′),1408(C5′),1147(C6′),1018
(C1″),727(C2″),707(C3″),673(C4″),657
(C5″)。
¼Á=ª^kB£4[Q
[7],
ÝÒ×
µ_ñ.
8¯ isoestin2′OαLarabinopyranoside。
_ñ.
9
Û>%¥
,
d»
U%βfÂ
。
ESIMSm/z449[M+H]+;1HNMR(DMSOd6,600
MHz)δ:1298(1H,s,5OH),674(1H,s,H3),
644(1H,d,J=18Hz,H6),678(1H,d,J=18
Hz,H8),742(1H,d,J=24Hz,H2′),690(1H,
d,J=84Hz,H5′),743(1H,brd,J=84Hz,
H6′),508(1H,d,J=72Hz,H1′),320~370
(6H,m,H2″~H6″);13CNMR(DMSOd6,150
MHz)δ:1634(C2),1036(C3),1823(C4),
1616(C5),1000(C6),1649(C7),948(C8),
1574(C9),1058(C10),1218(C1′),1140
(C2′),1462(C3′),1504(C4′),1164(C5′),
1196(C6′),1004(C1″),736(C2″),769
(C3″),700(C4″),776(C5″),611(C6″)。
¼
Á=ª^kB£4[Q
[10],
ÝÒ×µ_ñ.
9
¯ÀTì
7OβDbNûügÄ。
_ñ.
10
Û>%¥
,
d»
U%βfÂ
。
ESIMSm/z301[M-H]-;1HNMR(DMSOd6,600
MHz)δ:1282(1H,s,5OH),732(1H,s,H6′),
702(1H,s,H3),672(1H,s,H3′),615(1H,d,
J=20Hz,H6),638(1H,d,J=20Hz,H8);
13CNMR(DMSOd6,150MHz)δ:1617(C2),
1068(C3),1817(C4),1614(C5),985(C6),
1639(C7),935(C8),1572(C9),1035(C
10),1070(C1′),1505(C2′),1042(C3′),
1516(C4′),1387(C5′),1134(C6′)。
¼Á=
ª^kB£4[Q
[8],
ÝÒ×µ_ñ.
10
¯
isoetin。
_ñ.
11
Û>%¥
,
d»
U%βfÂ
。
ESIMSm/z287[M+H]+;1HNMR(DMSOd6,600
MHz)δ:740(1H,dd,J=84,20Hz,H6′),739
(1H,d,J=20Hz,H2′),689(1H,d,J=84Hz,
H5′),663(1H,s,H3),643(1H,d,J=20Hz,
H8),618(1H,d,J=20Hz,H6);13CNMR(DM
SOd6,150MHz)δ:1641(C2),1027(C3),1817
(C4),1615(C5),989(C6),1639(C7),939
(C8),1573(C9),1036(C10),1215(C1′),
1132(C2′),1456(C3′),1497(C4′),1161
(C5′),1196(C6′)。
2¼=ª^kB£4[
Q
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[1]
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,2004:107
[7] ShiSY,ZhangYP,ZhaoY,etalPreparativeisolationandpur
ificationofthreeflavonoidglycosidesfromTaraxacummongolicum
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[8] ChristianZIsoetinanditsderivatives:analytics,chemosystem
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ciumpiloselal(Asteraceae)[J]ActaSocBotPol,2009,78
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