期刊
PHYTOCHEMISTRY
卷 70, 期 2, 页码 278-287出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.phytochem.2008.12.012
关键词
6-C-glycosyl-3-deoxyanthocyanidins; 8-C-glycosyl-3-deoxyanthocyanidins; 6,8-Di-C-glycosyl-3-deoxyanthocyanidins; C-glycosylflavones; Rotamers; Clemmensen reduction; Stability; pH effects; 2D NMR
资金
- Norwegian Research Council of Norway
Nine C-glycosyldeoxyanthocyanidins, 6-C-beta-glucopyranosyl-7-0-methylapigeninidin, 6-C-beta-glucopyranosyl-7-O-methylluteolinidin, 6-C-beta-(2-O-beta-glucopyranosylglucopyranosyl)-7-O-methylapigeninidin, 6C-beta-(2-O-beta-glucopyranosylglucopyranosyl)-7,4'-di-O-methylapigeninidin, 8-C-beta-glucopyranosylapigeninidin, 8-C-beta-(2-O-alpha-rhamnopyranosylglucopyranosyl)apigeninidin, 8-C-beta-(2-O-alpha-(4'-O-acetyl-rhamnopyranosyl)glucopyranosyl)apigeninidin, 6,8-di-C-beta-glucopyranosylapigeninidin (8), 6,8-di-C-beta-glucopyranosyl-4'-O-methylluteolinidin (9), have been synthesized from their respective C-glycosylflavones (yields between 14% and 32%) by the Clemmensen reduction reaction using zinc-amalgam. The various precursors (C-glycosylflavones) of the C-glycosylanthocyanidins were isolated from either flowers of Iris sibirica L., leaves of Hawthorn 'Crataegi Folium Cum Flore', or lemons and oranges. This is the first time C-glycosylanthocyanidins have been synthesized. The structures of all flavonoids including the flavone rotamers were elucidated by 2D NMR techniques and high-resolution electrospray MS. The distribution of the various structural forms of 8 and 9 are different at pH 1.1, 4.5, and 7.0, however, the two pigments undergoes similar structural transformations at the various pH values. Pigments 8 and 9 with C-C linkages between the sugar moieties and the aglycone, were found to be far more stable towards acid hydrolysis than pelargonidin 3-O-glucoside, which has the typical anthocyanidin C-O linkage between the sugar and aglycone. This stability may extend the present use of anthocyanins as nutraceuticals, pharmaceuticals or colorants. (C) 2009 Elsevier Ltd. All rights reserved.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据