Dihydroisatropolone C from Streptomyces and Its Implication in Tropolone-Ring Construction for Isatropolone Biosynthesis

Isatropolones/isarubrolones are actinomycete secondary metabolites featuring a tropolone-ring in their structures. From the isatropolone/isarubrolone producer Streptomyces sp. CPCC 204095, 7,12-dihydroisatropolone C (H(2)ITC) is discovered and identified as a mixture of two interchangeable diastereo...

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Detalles Bibliográficos
Autores principales: Liu, Jiachang, Liu, Xiaoyan, Fu, Jie, Jiang, Bingya, Li, Shufen, Wu, Linzhuan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9099902/
https://www.ncbi.nlm.nih.gov/pubmed/35566231
http://dx.doi.org/10.3390/molecules27092882
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author Liu, Jiachang
Liu, Xiaoyan
Fu, Jie
Jiang, Bingya
Li, Shufen
Wu, Linzhuan
author_facet Liu, Jiachang
Liu, Xiaoyan
Fu, Jie
Jiang, Bingya
Li, Shufen
Wu, Linzhuan
author_sort Liu, Jiachang
collection PubMed
description Isatropolones/isarubrolones are actinomycete secondary metabolites featuring a tropolone-ring in their structures. From the isatropolone/isarubrolone producer Streptomyces sp. CPCC 204095, 7,12-dihydroisatropolone C (H(2)ITC) is discovered and identified as a mixture of two interchangeable diastereomers differing in the C-6 configuration. As a major metabolite in the mycelial growth period of Streptomyces sp. CPCC 204095, H(2)ITC can be oxidized spontaneously to isatropolone C (ITC), suggesting H(2)ITC is the physiological precursor of ITC. Characterization of H(2)ITC makes us propose dihydrotropolone-ring construction in the biosynthesis of isatropolones.
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spelling pubmed-90999022022-05-14 Dihydroisatropolone C from Streptomyces and Its Implication in Tropolone-Ring Construction for Isatropolone Biosynthesis Liu, Jiachang Liu, Xiaoyan Fu, Jie Jiang, Bingya Li, Shufen Wu, Linzhuan Molecules Communication Isatropolones/isarubrolones are actinomycete secondary metabolites featuring a tropolone-ring in their structures. From the isatropolone/isarubrolone producer Streptomyces sp. CPCC 204095, 7,12-dihydroisatropolone C (H(2)ITC) is discovered and identified as a mixture of two interchangeable diastereomers differing in the C-6 configuration. As a major metabolite in the mycelial growth period of Streptomyces sp. CPCC 204095, H(2)ITC can be oxidized spontaneously to isatropolone C (ITC), suggesting H(2)ITC is the physiological precursor of ITC. Characterization of H(2)ITC makes us propose dihydrotropolone-ring construction in the biosynthesis of isatropolones. MDPI 2022-04-30 /pmc/articles/PMC9099902/ /pubmed/35566231 http://dx.doi.org/10.3390/molecules27092882 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Liu, Jiachang
Liu, Xiaoyan
Fu, Jie
Jiang, Bingya
Li, Shufen
Wu, Linzhuan
Dihydroisatropolone C from Streptomyces and Its Implication in Tropolone-Ring Construction for Isatropolone Biosynthesis
title Dihydroisatropolone C from Streptomyces and Its Implication in Tropolone-Ring Construction for Isatropolone Biosynthesis
title_full Dihydroisatropolone C from Streptomyces and Its Implication in Tropolone-Ring Construction for Isatropolone Biosynthesis
title_fullStr Dihydroisatropolone C from Streptomyces and Its Implication in Tropolone-Ring Construction for Isatropolone Biosynthesis
title_full_unstemmed Dihydroisatropolone C from Streptomyces and Its Implication in Tropolone-Ring Construction for Isatropolone Biosynthesis
title_short Dihydroisatropolone C from Streptomyces and Its Implication in Tropolone-Ring Construction for Isatropolone Biosynthesis
title_sort dihydroisatropolone c from streptomyces and its implication in tropolone-ring construction for isatropolone biosynthesis
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9099902/
https://www.ncbi.nlm.nih.gov/pubmed/35566231
http://dx.doi.org/10.3390/molecules27092882
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