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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...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
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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 |
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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 |
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