Synthesis and antioxidant activities of berberine 9- O-benzoic acid derivatives

Yanfei Liu; Shuo Long; Shanshan Zhang; Yifu Tan; Ting Wang; Yuwei Wu; Ting Jiang; Xiaoqin Liu; Dongming Peng; Zhenbao Liu

doi:10.1039/d1ra01339d

Synthesis and antioxidant activities of berberine 9- O-benzoic acid derivatives

RSC Adv. 2021 May 13;11(29):17611-17621. doi: 10.1039/d1ra01339d.

Authors

Affiliations

¹ Department of Pharmaceutical Engineering, College of Chemistry and Chemical Engineering, Central South University Changsha 410083 China.
² Department of Pharmaceutics, Xiangya School of Pharmaceutical Sciences, Central South University Changsha 410013 China zhenbaoliu@csu.edu.cn.
³ Department of Medicinal Chemistry, School of Pharmacy, Hunan University of Chinese Medicine Changsha 410208 China.

Abstract

Although berberine (BBR) shows antioxidant activity, its activity is limited. We synthesized 9-O-benzoic acid berberine derivatives, and their antioxidant activities were screened via ABTS, DPPH, HOSC and FRAP assays. The para-position was modified with halogen elements on the benzoic acid ring, which led to an enhanced antioxidant activity and the substituent on the ortho-position was found to be better than the meta-position. Compounds 8p, 8c, 8d, 8i, 8j, 8l, and especially 8p showed significantly higher antioxidant activities, which could be attributed to the electronic donating groups. All the berberine derivatives possessed proper lipophilicities. In conclusion, compound 8p is a promising antioxidant candidate with remarkable elevated antioxidant activity and moderate lipophilicity.