Isotopic labelling of quercetin 3-glucoside

被引：30
作者：
Caldwell, Stuart T.
Petersson, Hanna M.
Farrugia, Louis J.
Mullen, William
Crozier, Alan
Hartley, Richard C. [1 ]
机构：
[1] Univ Glasgow, WestCHEM Dept Chem, Glasgow G12 8QQ, Lanark, Scotland
[2] Univ Glasgow, Div Biochem & Mol Biol, Glasgow G12 8QQ, Lanark, Scotland
来源：
TETRAHEDRON | 2006年 / 62卷 / 31期
关键词：
D O I：
10.1016/j.tet.2006.05.046
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The potentially important dietary antioxidant, quercetin 3-O-beta-D-glucoside, has been C-13-labelled at C-2 of the flavonoid unit by synthesis in 15% yield over five steps from [C-13] carbon dioxide. The route is appropriate for radiochemical synthesis. Formation of the protected 3-glucosylated flavonol appears to result from [1,7]-sigmatropic rearrangement with migration of a benzyl group followed by cyclisation. A free 5-OH results even when a phosphazene superbase is used. (c) 2006 Elsevier Ltd. All rights reserved.
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收藏
页码：7257 / 7265
页数：9
相关论文
共 40 条
[1]  
AHUJA M, 1974, INDIAN J CHEM, V12, P26
[2]   DFT study of pericyclic reaction cascades in the synthesis of antibiotic TAN-1085 [J].
Akerling, ZR ;
Norton, JE ;
Houk, KN .
ORGANIC LETTERS, 2004, 6 (23) :4273-4275
[3]   The type of sugar moiety is a major determinant of the small intestinal uptake and subsequent biliary excretion of dietary quercetin glycosides [J].
Arts, ICW ;
Sesink, ALA ;
Faassen-Peters, M ;
Hollman, PCH .
BRITISH JOURNAL OF NUTRITION, 2004, 91 (06) :841-847
[4]  
Bois F, 1999, SYNLETT, P1480
[5]   Regio- and stereoselective synthesis of the major metabolite of quercetin, quercetin-3-O-β-D-glucuronide [J].
Bouktaib, M ;
Atmani, A ;
Rolando, C .
TETRAHEDRON LETTERS, 2002, 43 (35) :6263-6266
[6]   Isotopic labelling of quercetin 4′-O-β-D-glucoside [J].
Caldwell, ST ;
Crozier, A ;
Hartley, RC .
TETRAHEDRON, 2000, 56 (24) :4101-4106
[7]   Quercetin glucosides inhibit glucose uptake into brush-border-membrane vesicles of porcine jejunum [J].
Cermak, R ;
Landgraf, S ;
Wolffram, S .
BRITISH JOURNAL OF NUTRITION, 2004, 91 (06) :849-855
[8]   Anthoxanthins Part XIV omega-Hydroxyphloracetophenone and certain derivatives - Synthesis of galangin under milder conditions than those used heretofore [J].
Chavan, JJ ;
Robinson, R .
JOURNAL OF THE CHEMICAL SOCIETY, 1933, :368-370
[9]   C-isoprenylation of flavonoids enhances binding affinity toward P-glycoprotein and modulation of cancer cell chemoresistance [J].
Comte, G ;
Daskiewicz, JB ;
Bayet, C ;
Conseil, G ;
Viornery-Vanier, A ;
Dumontet, C ;
Di Pietro, A ;
Barron, D .
JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (05) :763-768
[10]   SYNTHESIS OF 3-METHOXY-FLAVYLIUM AND 3-(BETA-D-GLUCOPYRANOSYLOXY)FLAVYLIUM IONS - INFLUENCE OF THE FLAVYLIUM SUBSTITUTION PATTERN ON THE REACTIVITY OF ANTHOCYANINS IN AQUEOUS-SOLUTION [J].
DANGLES, O ;
ELHAJJI, H .
HELVETICA CHIMICA ACTA, 1994, 77 (06) :1595-1610
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