Improvement of stability and lipophilicity of pelargonidin-3-glucoside by enzymatic acylation with aliphatic dicarboxylic acid.

Jiahong Xie, Xin Hao, Yiqiu Shang, Wei Chen

Food chemistry 2022 Sep 30

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Dicarboxylic acids derived acylated-anthocyanins are common in nature, which can also be obtained by enzymatic acylation of anthocyanins. However, little research have focused on the properties of anthocyanins with dicarboxylic acid derivatives due to the complexity of isolation, detection, and identification. In this work, pelargonidin-3-glucoside (Pg3G) was acylated with various dicarboxylic acids. The conversion yields of acylated Pg3G were positively associated with carbon chain lengths of dicarboxylic acids. The primary acylated products were identified as pelargonidin-3-(6″-malonyl) glucoside, pelargonidin-3-(6″-succinyl) glucoside, and pelargonidin-3-(6″-glutaryl) glucoside using LC-MS and NMR. Furthermore, the three acylated Pg3G derivatives exhibited improved thermostability and enhanced lipophilicity compared with Pg3G. The improved thermostability was attributed to the influence of dicarboxylic acids substituent on the distribution of flavylium cation, quinoidal base, hemiketal, cis-chalcone, and trans-chalcone at the equilibrium condition. Overall, our research provided insights about the improved stability and lipophilicity of pelargonidin-3-glucoside following enzymatic acylation with aliphatic dicarboxylic acids. Copyright © 2022 Elsevier Ltd. All rights reserved.

Citation

Jiahong Xie, Xin Hao, Yiqiu Shang, Wei Chen. Improvement of stability and lipophilicity of pelargonidin-3-glucoside by enzymatic acylation with aliphatic dicarboxylic acid. Food chemistry. 2022 Sep 30;389:133077