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Simultaneous determination of four coumaroylspermidine constituents in Carthamus tinctorius by HPLC-DAD

HPLC-DAD同时测定红花中4种亚精胺成分



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Simultaneousdeterminationoffourcoumaroylspermidineconstituentsin
CarthamustinctoriusbyHPLCDAD
LIShifei,YUANMaoye,ZHANGLiwei
(InstituteofMolecularScience,ShanxiUniversity,Taiyuan030006,China)
[Abstract] TheHPLCDADmethodwasestablishedtosimultaneouslydeterminethecontentsoffourcoumaroylspermidine[N1,
N5,N10(Z)tripcoumaroylspermidine(1),N1,N5(Z)N10(E)tripcoumaroylspermidine(2),N1(E)N5(Z)N10(E)
tripcoumaroylspermidine(3),andN1,N5,N10(E)tripcoumaroylspermidine(4)]inCarthamustinctoriusThemethodwas
performedonanEclipseXDBC18column(46mm×250mm,5μm)elutedwith47% methanolinanisocraticprogramTheflow
ratewas1mL·min-1;theinjectionvolumewas10μL,andthecolumntemperaturewas30℃Thedetectivewavelengthwas270,
280,290,and300nm,respectivelyFourcoumaroylspermidineconstituentsshowedagoodlinearityintherangeof0002100416
(r=09995),0002600512(r=09997),0002700540(r=09998)g·L-1,and0005001004(r=09998)g·
L-1,respectivelyTheaveragerecoveriesofthesefourcoumaroylspermidineconstituentswereintherangeof9861%1009% (RSD
23%30%).Inconclusion,themethodissimple,rapid,andsensitive,whichcouldbeusedasaquantitativedeterminationmethod
forthefourcoumaroylspermidinecomponentsinCtinctorius
[Keywords] Carthamustinctorius;HPLC;coumaroylspermidineconstituents
doi:10.4268/cjcmm20160819
  
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3 Y=38854X-50026 290 09998 00027~00540
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Table2 Recoveryofcoumaroylspermidines14
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825 408 1214 9804
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825 840 1633 9626
825 816 1609 9877
825 1176 2025 9936
825 1260 2024 9832
825 1224 1982 10317
2 1650 840 2441 9690 9968 25
1650 820 2481 9960
1650 804 2492 10266
1650 1680 3220 9661
1650 1640 3350 10366
1650 1608 3273 9767
1650 2529 4126 10031
1650 2460 4100 10129
1650 2412 4092 9843
3 2025 980 3057 10246 1009 25
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2025 1020 3001 9692
2025 1960 4140 9916
2025 2008 4032 9998
2025 2040 3969 10367
2025 2940 4991 9961
2025 3012 5186 9994
2025 3060 5037 10115
4 5700 2850 8592 9624 1001 30
5700 2842 8398 10117
5700 2834 8508 10136
5700 5700 11627 10020
5700 5684 11600 10170
5700 5668 11368 10467
5700 8550 14318 9852
5700 8526 14326 9494
5700 8502 13928 10204
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Table3 ContentsofcoumaroylspermidinesinCarthamustinctoriusfromdiferentregions(n=3) mg·g-1
ZF _HÉ

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0165±0050 0330±0024 0405±0035 1140±0068
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0142±0034 0320±0038 0403±0061 0644±0026
À9
0196±0020 0427±0026 0530±0033 0680±0027
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[1] KazumaK,TakahashiT,SatoK,etal.Quinochalconesandfla
vonoidsfromfreshfloretsindiferentcultivarsofCarthamustinc
toriusL.[J].BiosciBiotechnolBiochem,2000,64(8):1588.
[2] ZhangHL,NagatsuA,WatanabeT,etal.Antioxidativecom
poundsisolatedfromsaflower(CarthamustinctoriusL.)oil
cake[J].ChemPharmBul,1997,45(12):1910.
[3] 
h|

­Œ,Æ-»¢˜_ʵ­ËÉ̹ą†
[D].
23

$%*»A&o
,2004.
[4] AkihisaT,NozakiA,InoueY,etal.Alkanediolsfromflowerpet
alsofCarthamustinctorius[J].Phytochemistry,1997,45(4):
725.
[5] AkihisaT,OinumaH,TamuraT,etal.Erythrohentriacontane6,
8dioland11otheralkane6,8diolsfromCarthamustinctorius
[J].Phytochemistry,1994,36(1):105.
[6] 
©H“

‚t|

0]¢

Ö

$,¢˜_ʵ­,诰
[J].
%£A,
·
ÈÉ,µA
,1999,14(5):201.
[7] 
ðì1



!;;

¢˜²kB¬ÊµÄ…†

Ó[k

[J].
$,@k
,1984,9(1):31.
[8] NagatsuA,ZhangHL,WatanabeT,etal.Newsteroidandma
tairesinolglycosidesfromsaflower(CarthamustinctoriusL.)oil
cake[J].ChemPharmBul,1998,46(6):1044.
[9] JiangJS,LuL,YangYJ,etal.Newspermidinesfromtheflorets
ofCarthamustinctorius[J].JAsianNatProdRes,2008,10
(5):447.
[10] MaCM,NakamuraN,HatoriM,etal.InhibitoryefectsonHIV
1proteaseoftripcoumaroylspermidinefromArtemisiacaruifolia
andrelatedamides[J].ChemPharmBul,2001,49(7):915.
[11] ItoH,MiyakeM,NishitaniE,etal.Antitumorpromotingactivity
ofpolyphenolsfromCowaniamexicanaandColeogyneramosis
sima[J].CancerLet,1999,143(1):5.
[12] OhtaS,FujimakiT,UyMM,etal.Antioxidanthydroxycinnamic
acidderivativesisolatedfromBrazilianbeepolen[J].NatProd
Res,2007,21(8):726.
[13] ZhaoG,GaiaY,ChuaW J,etal.AnovelcompoundN1,N5
(Z)N10(E)tripcoumaroylspermidineisolatedfromCartham
ustinctoriusL.andactingbyserotonintransporterinhibition
[J].JEuroneuro,2009,19(10):749.
[14] LiW C,WangXY,LinPC,etal.Preparativeseparationand
purificationoffourcistransisomersofcoumaroylspermidineana
logsfromsaflowerbyhighspeedcountercurentchromatography
[J].JChromatogrB,2013,938(1):75.

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