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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...

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Autores principales: 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
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2020
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.
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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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