Synthesis of hydroxycinnamoyl 尾-d-xylopyranosides and evaluation of their antioxidant properties

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• 作者：Yasutaka Shimotori^a ; ^{yasu@mail.kitami-it.ac.jp" class="auth_mail} ; Masayuki Hoshi^a ; Kouji Soga^b ; Yosuke Osawa^b ; Tetsuo Miyakoshi^b
• 关键词：Hydroxycinnamic acids ; Hydroxycinnamoyl 尾-d-xylopyranosides ; Lipase ; Regioselective transesterification ; Antioxidant properties
• 刊名：Carbohydrate Research
• 出版年：31 March, 2014
• 年：2014
• 卷：388
• 期：Complete
• 页码：138-146
• 全文大小：703 K

文摘

Various hydroxycinnamoyl 尾-d-xylopyranosides were efficiently prepared from 2,3,4-tri-O-acetyl-伪-d-xylopyranosyl bromide (TAXB) with amine by amine-promoted glycosylation. The resulted acetylated hydroxycinnamoyl 尾-d-xylopyranosides with acetoxy groups at C-2, C-3, and C-4 were regioselectively deacetylated at C-4 position with Novozym 435. Antioxidant activities of free hydroxycinnamic acids and the respective 尾-d-xylopyranosides were evaluated by DPPH radical scavenging activity as well as their inhibitory effect on autoxidation of bulk methyl linoleate. The radical scavenging activity on 1,1-diphenyl-2-picrylhydrazyl (DPPH) decreased in the order ferulic acid > caffeic acid 鈮?#xA0;caffeoyl 尾-d-xylopyranosides 鈮?#xA0;sinapinic acid > sinapoyl 尾-d-xylopyranosides 鈮?#xA0;feruloyl 尾-d-xylopyranosides > p-coumaric acid > p-coumaroyl 尾-d-xylopyranosides. In bulk methyl linoleate, the antioxidant activity order against autoxidation was almost consistent with the scavenging activity order. The results showed that caffeoyl 尾-d-xylopyranosides and sinapoyl 尾-d-xylopyranosides were as effective as free caffeic acid, sinapinic acid, and ferulic acid.