Inducing Intermediates in Biotransformation of Natural Polyacetylene and A Novel Spiro-γ-Lactone from Red Ginseng by Solid Co-Culture of Two Gut Chaetomium globosum and The Potential Bioactivity Modification by Oxidative Metabolism

The ω-hydroxyl-panaxytriol (1) and ω-hydroxyl-dihydropanaxytriol (2)—are rare examples of polyacetylene metabolism by microbial transformation, and these new metabolites (1, 2) from fermented red...

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Main Authors:	Bang-Yan Wang, Chen-Hao Zhu, Xue-Qiong Yang, Ming Hu, Ting-Ting Xu, Xue-Yin Wang, Shuang Yang, Ya-Bin Yang, Zhong-Tao Ding
Format:	Article
Language:	English
Published:	MDPI AG 2020-03-01
Series:	Molecules
Subjects:	fermented red ginseng <i>chaetomium globosum</i> polyacetylene detoxification oxidative metabolism
Online Access:	https://www.mdpi.com/1420-3049/25/5/1216

id	doaj-e10e63ee82eb401dadcd7c76a017a127
record_format	Article
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Bang-Yan Wang Chen-Hao Zhu Xue-Qiong Yang Ming Hu Ting-Ting Xu Xue-Yin Wang Shuang Yang Ya-Bin Yang Zhong-Tao Ding
spellingShingle	Bang-Yan Wang Chen-Hao Zhu Xue-Qiong Yang Ming Hu Ting-Ting Xu Xue-Yin Wang Shuang Yang Ya-Bin Yang Zhong-Tao Ding Inducing Intermediates in Biotransformation of Natural Polyacetylene and A Novel Spiro-γ-Lactone from Red Ginseng by Solid Co-Culture of Two Gut <i>Chaetomium globosum</i> and The Potential Bioactivity Modification by Oxidative Metabolism Molecules fermented red ginseng <i>chaetomium globosum</i> polyacetylene detoxification oxidative metabolism
author_facet	Bang-Yan Wang Chen-Hao Zhu Xue-Qiong Yang Ming Hu Ting-Ting Xu Xue-Yin Wang Shuang Yang Ya-Bin Yang Zhong-Tao Ding
author_sort	Bang-Yan Wang
title	Inducing Intermediates in Biotransformation of Natural Polyacetylene and A Novel Spiro-γ-Lactone from Red Ginseng by Solid Co-Culture of Two Gut <i>Chaetomium globosum</i> and The Potential Bioactivity Modification by Oxidative Metabolism
title_short	Inducing Intermediates in Biotransformation of Natural Polyacetylene and A Novel Spiro-γ-Lactone from Red Ginseng by Solid Co-Culture of Two Gut <i>Chaetomium globosum</i> and The Potential Bioactivity Modification by Oxidative Metabolism
title_full	Inducing Intermediates in Biotransformation of Natural Polyacetylene and A Novel Spiro-γ-Lactone from Red Ginseng by Solid Co-Culture of Two Gut <i>Chaetomium globosum</i> and The Potential Bioactivity Modification by Oxidative Metabolism
title_fullStr	Inducing Intermediates in Biotransformation of Natural Polyacetylene and A Novel Spiro-γ-Lactone from Red Ginseng by Solid Co-Culture of Two Gut <i>Chaetomium globosum</i> and The Potential Bioactivity Modification by Oxidative Metabolism
title_full_unstemmed	Inducing Intermediates in Biotransformation of Natural Polyacetylene and A Novel Spiro-γ-Lactone from Red Ginseng by Solid Co-Culture of Two Gut <i>Chaetomium globosum</i> and The Potential Bioactivity Modification by Oxidative Metabolism
title_sort	inducing intermediates in biotransformation of natural polyacetylene and a novel spiro-γ-lactone from red ginseng by solid co-culture of two gut <i>chaetomium globosum</i> and the potential bioactivity modification by oxidative metabolism
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2020-03-01
description	The ω-hydroxyl-panaxytriol (<b>1</b>) and ω-hydroxyl-dihydropanaxytriol (<b>2</b>)—are rare examples of polyacetylene metabolism by microbial transformation, and these new metabolites (<b>1</b>, <b>2</b>) from fermented red ginseng (FRG) by solid co-culture induction of two <i>Chaetomium globosum</i> should be the intermediates of biotransformation of panaxylactone (metabolite <b>A</b>). The metabolic pathway of panaxylactone was also exhibited. The ingredients of red ginseng (RG) also induced the production of rare 6/5/5 tricyclic ring spiro-γ-lactone skeleton (<b>3</b>). The ω-hydroxylation of new intermediates (<b>1</b>, <b>2</b>) decreases cytotoxicity and antifungal activity against <i>C. globosum</i> compared with that of its bioprecursor panaxytriol. Additionally, compounds <b>1</b> and <b>2</b> indicated obvious inhibition against nitric oxide (NO) production, with ratios of 44.80 ± 1.37 and 23.10 ± 1.00% at 50 μM. <b>1</b> has an equivalent inhibition of NO production compared with the positive drug. So, the microbial biotransformation that occurred in FRG fermented by gut <i>C. globosum</i> can change the original bioactivity of polyacetylene, which gave a basis about the metabolic modification of red ginseng by intestinal fungus fermentation.
topic	fermented red ginseng <i>chaetomium globosum</i> polyacetylene detoxification oxidative metabolism
url	https://www.mdpi.com/1420-3049/25/5/1216
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spelling	doaj-e10e63ee82eb401dadcd7c76a017a1272020-11-25T03:03:25ZengMDPI AGMolecules1420-30492020-03-01255121610.3390/molecules25051216molecules25051216Inducing Intermediates in Biotransformation of Natural Polyacetylene and A Novel Spiro-γ-Lactone from Red Ginseng by Solid Co-Culture of Two Gut <i>Chaetomium globosum</i> and The Potential Bioactivity Modification by Oxidative MetabolismBang-Yan Wang0Chen-Hao Zhu1Xue-Qiong Yang2Ming Hu3Ting-Ting Xu4Xue-Yin Wang5Shuang Yang6Ya-Bin Yang7Zhong-Tao Ding8Functional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, 2st Cuihu North Road, Kunming 650091, ChinaFunctional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, 2st Cuihu North Road, Kunming 650091, ChinaFunctional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, 2st Cuihu North Road, Kunming 650091, ChinaFunctional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, 2st Cuihu North Road, Kunming 650091, ChinaFunctional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, 2st Cuihu North Road, Kunming 650091, ChinaFunctional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, 2st Cuihu North Road, Kunming 650091, ChinaFunctional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, 2st Cuihu North Road, Kunming 650091, ChinaFunctional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, 2st Cuihu North Road, Kunming 650091, ChinaFunctional Molecules Analysis and Biotransformation Key Laboratory of Universities in Yunnan Province, Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, 2st Cuihu North Road, Kunming 650091, ChinaThe ω-hydroxyl-panaxytriol (<b>1</b>) and ω-hydroxyl-dihydropanaxytriol (<b>2</b>)—are rare examples of polyacetylene metabolism by microbial transformation, and these new metabolites (<b>1</b>, <b>2</b>) from fermented red ginseng (FRG) by solid co-culture induction of two <i>Chaetomium globosum</i> should be the intermediates of biotransformation of panaxylactone (metabolite <b>A</b>). The metabolic pathway of panaxylactone was also exhibited. The ingredients of red ginseng (RG) also induced the production of rare 6/5/5 tricyclic ring spiro-γ-lactone skeleton (<b>3</b>). The ω-hydroxylation of new intermediates (<b>1</b>, <b>2</b>) decreases cytotoxicity and antifungal activity against <i>C. globosum</i> compared with that of its bioprecursor panaxytriol. Additionally, compounds <b>1</b> and <b>2</b> indicated obvious inhibition against nitric oxide (NO) production, with ratios of 44.80 ± 1.37 and 23.10 ± 1.00% at 50 μM. <b>1</b> has an equivalent inhibition of NO production compared with the positive drug. So, the microbial biotransformation that occurred in FRG fermented by gut <i>C. globosum</i> can change the original bioactivity of polyacetylene, which gave a basis about the metabolic modification of red ginseng by intestinal fungus fermentation.https://www.mdpi.com/1420-3049/25/5/1216fermented red ginseng<i>chaetomium globosum</i>polyacetylenedetoxificationoxidative metabolism

Inducing Intermediates in Biotransformation of Natural Polyacetylene and A Novel Spiro-γ-Lactone from Red Ginseng by Solid Co-Culture of Two Gut <i>Chaetomium globosum</i> and The Potential Bioactivity Modification by Oxidative Metabolism

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