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

Jiachang Liu; Xiaoyan Liu; Jie Fu; Bingya Jiang; Shufen Li; Linzhuan Wu

doi:10.3390/molecules27092882

Molecules (Apr 2022)

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

Jiachang Liu,
Xiaoyan Liu,
Jie Fu,
Bingya Jiang,
Shufen Li,
Linzhuan Wu

Affiliations

Jiachang Liu: NHC Key Laboratory of Biotechnology of Antibiotics, CAMS Key Laboratory of Synthetic Biology for Drug Innovation, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Tiantan Xili, Beijing 100050, China
Xiaoyan Liu: NHC Key Laboratory of Biotechnology of Antibiotics, CAMS Key Laboratory of Synthetic Biology for Drug Innovation, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Tiantan Xili, Beijing 100050, China
Jie Fu: NHC Key Laboratory of Biotechnology of Antibiotics, CAMS Key Laboratory of Synthetic Biology for Drug Innovation, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Tiantan Xili, Beijing 100050, China
Bingya Jiang: NHC Key Laboratory of Biotechnology of Antibiotics, CAMS Key Laboratory of Synthetic Biology for Drug Innovation, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Tiantan Xili, Beijing 100050, China
Shufen Li: NHC Key Laboratory of Biotechnology of Antibiotics, CAMS Key Laboratory of Synthetic Biology for Drug Innovation, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Tiantan Xili, Beijing 100050, China
Linzhuan Wu: NHC Key Laboratory of Biotechnology of Antibiotics, CAMS Key Laboratory of Synthetic Biology for Drug Innovation, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Tiantan Xili, Beijing 100050, China

DOI: https://doi.org/10.3390/molecules27092882
Journal volume & issue: Vol. 27, no. 9
p. 2882

Abstract

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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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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