Synthesis of various β-D-glucopyranosyl and β-D-xylopyranosyl hydroxybenzoates and evaluation of their antioxidant activities

Heterocyclic communications

article

Yasutaka Shimotori¹  Masayuki Hoshi²  Yosuke Osawa²  Tetsuo Miyakoshi² 

[1] Department of Biotechnology and Environmental Chemistry, Kitami Institute of Technology;Department of Applied Chemistry, School of Science of Technology, Meiji University

关键词: antioxidant activity;    β-D-glycopyranosyl hydroxybenzoate;    hydroxybenzoic acid;    lipase-catalyzed regioselective deacetylation;    methyl linoleate;   

DOI  :  10.1515/hc-2016-0214

学科分类：内科医学

来源: De Gruyter

【 摘 要 】

Various β-D-glucopyranosyl and β-D-xylopyranosyl hydroxybenzoates were efficiently prepared from 2,3,4,6-tetra- O -acetyl-α-D-glucopyranosyl bromide (TAGB) or 2,3,4-tri- O -acetyl-α-D-xylopyranosyl bromide (TAXB), respectively, by amine-promoted glycosylation. Regioselective deacetylation of the resulting acetylated β-D-gluco- and β-D-xylopyranosyl hydroxybenzoates was investigated using Novozym 435 as a lipase catalyst. In the case of β-D-glucopyranosyl hydroxybenzoates, Novozym 435-catalyzed deacetylation is regioselective at C-4 and C-6 positions. On the other hand, β-D-xylopyranosyl hydroxybenzoates are deacetylated only at the C-4 position. Antioxidant activities of free hydroxybenzoic acids and the respective β-D-gluco- and β-D-xylopyranosyl hydroxybenzoates were evaluated by DPPH˙ radical scavenging as well as their inhibitory effect on autoxidation of bulk methyl linoleate. The β-D-xylopyranosyl protocatechoate, as well as quercetin and α-tochopherol, show high antioxidant activity for the radical scavenging activity by 1,1-diphenyl-2-picrylhydrazyl (DPPH˙). In bulk methyl linoleate, the antioxidant activities of β-D-gluco- and β-D-xylopyranosyl protocatechoates are higher than that of α-tocopherol.

【 授权许可】

CC BY|CC BY-NC-ND