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


ABSTRACT: 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 (H2ITC) 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, H2ITC can be oxidized spontaneously to isatropolone C (ITC), suggesting H2ITC is the physiological precursor of ITC. Characterization of H2ITC makes us propose dihydrotropolone-ring construction in the biosynthesis of isatropolones.

SUBMITTER: Liu J 

PROVIDER: S-EPMC9099902 | biostudies-literature | 2022 Apr

REPOSITORIES: biostudies-literature

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Dihydroisatropolone C from <i>Streptomyces</i> and Its Implication in Tropolone-Ring Construction for Isatropolone Biosynthesis.

Liu Jiachang J   Liu Xiaoyan X   Fu Jie J   Jiang Bingya B   Li Shufen S   Wu Linzhuan L  

Molecules (Basel, Switzerland) 20220430 9


Isatropolones/isarubrolones are actinomycete secondary metabolites featuring a tropolone-ring in their structures. From the isatropolone/isarubrolone producer <i>Streptomyces</i> sp. CPCC 204095, 7,12-dihydroisatropolone C (H<sub>2</sub>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 <i>Streptomyces</i> sp. CPCC 204095, H<sub>2</sub>ITC can be oxidized spontaneously to i  ...[more]

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