Antioxidant activities of chlorogenic acid derivatives with different acyl donor chain lengths and their stabilities during in vitro simulated gastrointestinal digestion

Shan Wang; Yue Li; Xiangyong Meng; Shangwei Chen; Dejian Huang; Yongmei Xia; Song Zhu

doi:10.1016/j.foodchem.2021.129904

Antioxidant activities of chlorogenic acid derivatives with different acyl donor chain lengths and their stabilities during in vitro simulated gastrointestinal digestion

Food Chem. 2021 Apr 20:357:129904. doi: 10.1016/j.foodchem.2021.129904. Online ahead of print.

Authors

Shan Wang¹, Yue Li², Xiangyong Meng³, Shangwei Chen⁴, Dejian Huang⁵, Yongmei Xia⁴, Song Zhu⁶

Affiliations

¹ State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, Jiangsu 214122, China; International Joint Laboratory on Food Safety, Jiangnan University, Wuxi, Jiangsu 214122, China.
² State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, Jiangsu 214122, China; School of Food Science and Technology, Jiangnan University, Wuxi, Jiangsu 214122, China.
³ College of Life Science, Anhui Normal University, Wuhu, Anhui 241000, China.
⁴ State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, Jiangsu 214122, China.
⁵ Department of Food Science and Technology, National University of Singapore, Singapore 117543, Singapore.
⁶ State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi, Jiangsu 214122, China; International Joint Laboratory on Food Safety, Jiangnan University, Wuxi, Jiangsu 214122, China. Electronic address: zhusong@jiangnan.edu.cn.

PMID: 33915469
DOI: 10.1016/j.foodchem.2021.129904

Abstract

In this study, chlorogenic acid (CA) was acylated with vinyl esters of different carbon chain lengths under the action of the lipase Lipozyme RM. Five CA derivatives (C2-CA, C4-CA, C6-CA, C8-CA, and C12-CA) with different lipophilicities were obtained, and their digestive stabilities and antioxidant activities were evaluated. The lipophilicities were positively correlated with the digestive stabilities of CA derivatives. The antioxidant activities of CA derivatives did not change with the reduction of phenolic hydroxyl groups, and their capacity to scavenge 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS⁺•) and 1,1-diphenyl-2-picrylhydrazyl (DPPH•) were similar to those of CA. In cellular antioxidant activity (CAA) tests, it was found that the capacity of these derivates to cross cell membranes were enhanced upon enhancing lipophilicity, and their antioxidant activities were improved. C12-CA showed the best antioxidant activity with a median effective dose (EC₅₀) of 9.40 μg/mL, which was significantly lower than that of CA (i.e., 29.08 μg/mL).

Keywords: Acylated chlorogenic acid; Antioxidantactivity; Chlorogenic acid; Digestive stability; Lipophilization.