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Synthesis and antioxidant activities of berberine 9-O-benzoic acid derivatives. 2021

Yanfei Liu, and Shuo Long, and Shanshan Zhang, and Yifu Tan, and Ting Wang, and Yuwei Wu, and Ting Jiang, and Xiaoqin Liu, and Dongming Peng, and Zhenbao Liu
Department of Pharmaceutical Engineering, College of Chemistry and Chemical Engineering, Central South University Changsha 410083 China.

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.

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