A facile synthesis of isoflavone 7-O-glucuronides

被引：30

作者：

Al-Maharik, Nawaf ^{[1
]}

Botting, Nigel P. ^{[1
]}

机构：

[1] Univ St Andrews, Sch Chem, St Andrews KY16 9ST, Fife, Scotland

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 49期

关键词：

isoflavones; glucuronides; phytoestrogens; glycosylation;

D O I：

10.1016/j.tetlet.2006.10.034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method is presented for the synthesis of isoflavone 7-glucuronides using a N-(4-methoxyphenyl)-trifluoroacetimidate glucuronsyl donor. A 4-hexanoyl derivative of the isoflavone is used in the coupling reaction, both for protection and to improve solubility. These glucuronides are the human metabolites of estrogenic dietary isotlavones, but their biological activity and pharmacokinetics have yet to be established as until now there were no good methods for their synthesis. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：8703 / 8706

页数：4

共 22 条

[11] The phase transfer catalysed synthesis of isoflavone-O-glucosides [J].

Lewis, P ;

Kaltia, S ;

Wähälä, K .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (16) :2481-2484

[12] Facile synthesis of flavonoid 7-O-glycosides [J].

Li, M ;

Han, XW ;

Yu, B .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (17) :6842-6845

[13] Isoflavones in soy-based infant formulas [J].

Murphy, PA ;

Song, TT ;

Buseman, G ;

Barua, K .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1997, 45 (12) :4635-4638

[14] Syntheses of daidzein-7-yl β-D-glucopyranosiduronic acid and daidzein-4′,7-yl di-β-D-glucopyranosiduronic acid [J].

Needs, PW ;

Williamson, G .

CARBOHYDRATE RESEARCH, 2001, 330 (04) :511-515

[15] Isoflavones, substances with multi-biological and clinical properties [J].

Ren, MQ ;

Kuhn, G ;

Wegner, J ;

Chen, J .

EUROPEAN JOURNAL OF NUTRITION, 2001, 40 (04) :135-146

[16] Soy protein, isoflavones, and cardiovascular health - An American heart association science advisory for professionals from the nutrition committee [J].

Sacks, FM ;

Lichtenstein, A ;

Van Horn, L ;

Harris, W ;

Kris-Etherton, P ;

Winston, M .

CIRCULATION, 2006, 113 (07) :1034-1044

[17] Comparing the pharmacokinetics of daidzein and genistein with the use of 13C-labeled tracers in premenopausal women [J].

Setchell, KDR ;

Faughnan, MS ;

Avades, T ;

Zimmer-Nechemias, L ;

Brown, NM ;

Wolfe, BE ;

Brashear, WT ;

Desai, P ;

Oldfield, MF ;

Botting, NP ;

Cassidy, A .

AMERICAN JOURNAL OF CLINICAL NUTRITION, 2003, 77 (02) :411-419

[18] Exposure of infants to phyto-oestrogens from soy-based infant formula [J].

Setchell, KDR ;

ZimmerNechemias, L ;

Cai, JN ;

Heubi, JE .

LANCET, 1997, 350 (9070) :23-27

[19] Absorption and metabolism of soy isoflavones - from food to dietary supplements and adults to infants [J].

Setchell, KDR .

JOURNAL OF NUTRITION, 2000, 130 (03) :654S-655S

[20] Mass balance study of isoflavones during soybean processing [J].

Wang, HJ ;

Murphy, PA .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1996, 44 (08) :2377-2383

← 1 2 3 →