Common origin of methylenedioxy ring degradation and demethylation in bacteria

Abstract Plants produce many specific secondary metabolites as a response to environmental stress, especially biological stress. These compounds show strong biological activities and high stability against degradation by microbes and animals. Berberine, a benzylisoquinoline alkaloid, is found in man...

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Main Authors:	Hisashi Takeda, Kazuki Ishikawa, Hinaka Yoshida, Daisuke Kasai, Daigo Wakana, Masao Fukuda, Fumihiko Sato, Tomoo Hosoe
Format:	Article
Language:	English
Published:	Nature Publishing Group 2017-08-01
Series:	Scientific Reports
Online Access:	https://doi.org/10.1038/s41598-017-07370-x

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spelling	doaj-73af0d3f7204474aaa3f3aa3a46ec0922020-12-08T02:50:17ZengNature Publishing GroupScientific Reports2045-23222017-08-01711810.1038/s41598-017-07370-xCommon origin of methylenedioxy ring degradation and demethylation in bacteriaHisashi Takeda0Kazuki Ishikawa1Hinaka Yoshida2Daisuke Kasai3Daigo Wakana4Masao Fukuda5Fumihiko Sato6Tomoo Hosoe7Department of Organic Chemistry, Hoshi University, EbaraDepartment of Organic Chemistry, Hoshi University, EbaraDepartment of Organic Chemistry, Hoshi University, EbaraDepartment of Bioengineering, Nagaoka University of Technology, KamitomiokaDepartment of Organic Chemistry, Hoshi University, EbaraDepartment of Bioengineering, Nagaoka University of Technology, KamitomiokaDivision of Integrated Life Science, Graduate School of Biostudies, Kyoto University, KitashirakawaDepartment of Organic Chemistry, Hoshi University, EbaraAbstract Plants produce many specific secondary metabolites as a response to environmental stress, especially biological stress. These compounds show strong biological activities and high stability against degradation by microbes and animals. Berberine, a benzylisoquinoline alkaloid, is found in many plant species and has strong antimicrobial activity, and is often included in traditional herbal medicines. We previously investigated how berberine is degraded in nature and we isolated two berberine-utilizing bacteria. In this study, we characterized the gene encoding the enzyme that degrades the 2,3-methylenedioxy ring of berberine; this ring is important for its activity and stability. Further characterization of several other berberine-utilizing bacteria and the genes encoding key demethylenation enzymes revealed that these enzymes are tetrahydrofolate dependent and similar to demethylation enzymes such as GcvT. Because the degradation of O-methyl groups or the methylenedioxy ring in phenolic compounds such as lignin, lignan and many other natural products, including berberine, is the key step for the catabolism of these compounds, our discovery reveals the common origin of the catabolism of these stable chemicals in bacteria.https://doi.org/10.1038/s41598-017-07370-x
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Hisashi Takeda Kazuki Ishikawa Hinaka Yoshida Daisuke Kasai Daigo Wakana Masao Fukuda Fumihiko Sato Tomoo Hosoe
spellingShingle	Hisashi Takeda Kazuki Ishikawa Hinaka Yoshida Daisuke Kasai Daigo Wakana Masao Fukuda Fumihiko Sato Tomoo Hosoe Common origin of methylenedioxy ring degradation and demethylation in bacteria Scientific Reports
author_facet	Hisashi Takeda Kazuki Ishikawa Hinaka Yoshida Daisuke Kasai Daigo Wakana Masao Fukuda Fumihiko Sato Tomoo Hosoe
author_sort	Hisashi Takeda
title	Common origin of methylenedioxy ring degradation and demethylation in bacteria
title_short	Common origin of methylenedioxy ring degradation and demethylation in bacteria
title_full	Common origin of methylenedioxy ring degradation and demethylation in bacteria
title_fullStr	Common origin of methylenedioxy ring degradation and demethylation in bacteria
title_full_unstemmed	Common origin of methylenedioxy ring degradation and demethylation in bacteria
title_sort	common origin of methylenedioxy ring degradation and demethylation in bacteria
publisher	Nature Publishing Group
series	Scientific Reports
issn	2045-2322
publishDate	2017-08-01
description	Abstract Plants produce many specific secondary metabolites as a response to environmental stress, especially biological stress. These compounds show strong biological activities and high stability against degradation by microbes and animals. Berberine, a benzylisoquinoline alkaloid, is found in many plant species and has strong antimicrobial activity, and is often included in traditional herbal medicines. We previously investigated how berberine is degraded in nature and we isolated two berberine-utilizing bacteria. In this study, we characterized the gene encoding the enzyme that degrades the 2,3-methylenedioxy ring of berberine; this ring is important for its activity and stability. Further characterization of several other berberine-utilizing bacteria and the genes encoding key demethylenation enzymes revealed that these enzymes are tetrahydrofolate dependent and similar to demethylation enzymes such as GcvT. Because the degradation of O-methyl groups or the methylenedioxy ring in phenolic compounds such as lignin, lignan and many other natural products, including berberine, is the key step for the catabolism of these compounds, our discovery reveals the common origin of the catabolism of these stable chemicals in bacteria.
url	https://doi.org/10.1038/s41598-017-07370-x
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Common origin of methylenedioxy ring degradation and demethylation in bacteria

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