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Intramolecular Annulation of Gossypol by Laccase to Produce Safe Cottonseed Protein
The presence of the phenol gossypol has severely limited the utilization of cottonseed meal and oil in the food and animal feed industries. Highly efficient means of biodegradation of gossypol and an understanding of the cytotoxicity of its degradation products remain outside current knowledge and a...
Autores principales: | , , , , , , , , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Frontiers Media S.A.
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7736553/ https://www.ncbi.nlm.nih.gov/pubmed/33335884 http://dx.doi.org/10.3389/fchem.2020.583176 |
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author | Wang, Lin Chen, Ming Luo, Xuecai Fan, Yanan Zheng, Zai He, Zongqin Yin, Ruochun Meng, Tao Xu, Shuyang Pan, Yu Su, Jihu Du, Jiangfeng Zhang, Liang Tian, Xiaohe Tian, Yupeng Chen, Dongdong Ge, Honghua Zhang, Nannan Li, Ping |
author_facet | Wang, Lin Chen, Ming Luo, Xuecai Fan, Yanan Zheng, Zai He, Zongqin Yin, Ruochun Meng, Tao Xu, Shuyang Pan, Yu Su, Jihu Du, Jiangfeng Zhang, Liang Tian, Xiaohe Tian, Yupeng Chen, Dongdong Ge, Honghua Zhang, Nannan Li, Ping |
author_sort | Wang, Lin |
collection | PubMed |
description | The presence of the phenol gossypol has severely limited the utilization of cottonseed meal and oil in the food and animal feed industries. Highly efficient means of biodegradation of gossypol and an understanding of the cytotoxicity of its degradation products remain outside current knowledge and are of universal interest. In this work, we showed for the first time that laccase can catalyze the intramolecular annulation of the aldehyde and hydroxyl groups of gossypol for the o-semiquinone radical and originate the released ·OH radical. It was further found that the oxidation of aldehyde groups significantly decreases reproductive toxicity and hepatotoxicity. These results indicate a novel detoxification pathway for gossypol and reveal the crucial role played by radical species in cyclization. This discovery could facilitate the development of safe, convenient, and low-cost industrial methods for the detoxification of cotton protein and oil resources. |
format | Online Article Text |
id | pubmed-7736553 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | Frontiers Media S.A. |
record_format | MEDLINE/PubMed |
spelling | pubmed-77365532020-12-16 Intramolecular Annulation of Gossypol by Laccase to Produce Safe Cottonseed Protein Wang, Lin Chen, Ming Luo, Xuecai Fan, Yanan Zheng, Zai He, Zongqin Yin, Ruochun Meng, Tao Xu, Shuyang Pan, Yu Su, Jihu Du, Jiangfeng Zhang, Liang Tian, Xiaohe Tian, Yupeng Chen, Dongdong Ge, Honghua Zhang, Nannan Li, Ping Front Chem Chemistry The presence of the phenol gossypol has severely limited the utilization of cottonseed meal and oil in the food and animal feed industries. Highly efficient means of biodegradation of gossypol and an understanding of the cytotoxicity of its degradation products remain outside current knowledge and are of universal interest. In this work, we showed for the first time that laccase can catalyze the intramolecular annulation of the aldehyde and hydroxyl groups of gossypol for the o-semiquinone radical and originate the released ·OH radical. It was further found that the oxidation of aldehyde groups significantly decreases reproductive toxicity and hepatotoxicity. These results indicate a novel detoxification pathway for gossypol and reveal the crucial role played by radical species in cyclization. This discovery could facilitate the development of safe, convenient, and low-cost industrial methods for the detoxification of cotton protein and oil resources. Frontiers Media S.A. 2020-12-01 /pmc/articles/PMC7736553/ /pubmed/33335884 http://dx.doi.org/10.3389/fchem.2020.583176 Text en Copyright © 2020 Wang, Chen, Luo, Fan, Zheng, He, Yin, Meng, Xu, Pan, Su, Du, Zhang, Tian, Tian, Chen, Ge, Zhang and Li. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms. |
spellingShingle | Chemistry Wang, Lin Chen, Ming Luo, Xuecai Fan, Yanan Zheng, Zai He, Zongqin Yin, Ruochun Meng, Tao Xu, Shuyang Pan, Yu Su, Jihu Du, Jiangfeng Zhang, Liang Tian, Xiaohe Tian, Yupeng Chen, Dongdong Ge, Honghua Zhang, Nannan Li, Ping Intramolecular Annulation of Gossypol by Laccase to Produce Safe Cottonseed Protein |
title | Intramolecular Annulation of Gossypol by Laccase to Produce Safe Cottonseed Protein |
title_full | Intramolecular Annulation of Gossypol by Laccase to Produce Safe Cottonseed Protein |
title_fullStr | Intramolecular Annulation of Gossypol by Laccase to Produce Safe Cottonseed Protein |
title_full_unstemmed | Intramolecular Annulation of Gossypol by Laccase to Produce Safe Cottonseed Protein |
title_short | Intramolecular Annulation of Gossypol by Laccase to Produce Safe Cottonseed Protein |
title_sort | intramolecular annulation of gossypol by laccase to produce safe cottonseed protein |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7736553/ https://www.ncbi.nlm.nih.gov/pubmed/33335884 http://dx.doi.org/10.3389/fchem.2020.583176 |
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