Cargando…

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

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, whi...

Descripción completa

Detalles Bibliográficos
Autores principales: Liu, Yanfei, Long, Shuo, Zhang, Shanshan, Tan, Yifu, Wang, Ting, Wu, Yuwei, Jiang, Ting, Liu, Xiaoqin, Peng, Dongming, Liu, Zhenbao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9033176/
https://www.ncbi.nlm.nih.gov/pubmed/35480221
http://dx.doi.org/10.1039/d1ra01339d
_version_ 1784692825514835968
author Liu, Yanfei
Long, Shuo
Zhang, Shanshan
Tan, Yifu
Wang, Ting
Wu, Yuwei
Jiang, Ting
Liu, Xiaoqin
Peng, Dongming
Liu, Zhenbao
author_facet Liu, Yanfei
Long, Shuo
Zhang, Shanshan
Tan, Yifu
Wang, Ting
Wu, Yuwei
Jiang, Ting
Liu, Xiaoqin
Peng, Dongming
Liu, Zhenbao
author_sort Liu, Yanfei
collection PubMed
description 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.
format Online
Article
Text
id pubmed-9033176
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-90331762022-04-26 Synthesis and antioxidant activities of berberine 9-O-benzoic acid derivatives Liu, Yanfei Long, Shuo Zhang, Shanshan Tan, Yifu Wang, Ting Wu, Yuwei Jiang, Ting Liu, Xiaoqin Peng, Dongming Liu, Zhenbao RSC Adv Chemistry 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. The Royal Society of Chemistry 2021-05-13 /pmc/articles/PMC9033176/ /pubmed/35480221 http://dx.doi.org/10.1039/d1ra01339d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Liu, Yanfei
Long, Shuo
Zhang, Shanshan
Tan, Yifu
Wang, Ting
Wu, Yuwei
Jiang, Ting
Liu, Xiaoqin
Peng, Dongming
Liu, Zhenbao
Synthesis and antioxidant activities of berberine 9-O-benzoic acid derivatives
title Synthesis and antioxidant activities of berberine 9-O-benzoic acid derivatives
title_full Synthesis and antioxidant activities of berberine 9-O-benzoic acid derivatives
title_fullStr Synthesis and antioxidant activities of berberine 9-O-benzoic acid derivatives
title_full_unstemmed Synthesis and antioxidant activities of berberine 9-O-benzoic acid derivatives
title_short Synthesis and antioxidant activities of berberine 9-O-benzoic acid derivatives
title_sort synthesis and antioxidant activities of berberine 9-o-benzoic acid derivatives
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9033176/
https://www.ncbi.nlm.nih.gov/pubmed/35480221
http://dx.doi.org/10.1039/d1ra01339d
work_keys_str_mv AT liuyanfei synthesisandantioxidantactivitiesofberberine9obenzoicacidderivatives
AT longshuo synthesisandantioxidantactivitiesofberberine9obenzoicacidderivatives
AT zhangshanshan synthesisandantioxidantactivitiesofberberine9obenzoicacidderivatives
AT tanyifu synthesisandantioxidantactivitiesofberberine9obenzoicacidderivatives
AT wangting synthesisandantioxidantactivitiesofberberine9obenzoicacidderivatives
AT wuyuwei synthesisandantioxidantactivitiesofberberine9obenzoicacidderivatives
AT jiangting synthesisandantioxidantactivitiesofberberine9obenzoicacidderivatives
AT liuxiaoqin synthesisandantioxidantactivitiesofberberine9obenzoicacidderivatives
AT pengdongming synthesisandantioxidantactivitiesofberberine9obenzoicacidderivatives
AT liuzhenbao synthesisandantioxidantactivitiesofberberine9obenzoicacidderivatives