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

Molecules

Jiachang Liu¹  Jie Fu¹  Bingya Jiang¹  Xiaoyan Liu¹  Shufen Li¹  Linzhuan Wu¹ 

[1] 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;

关键词: Streptomyces;    7,12-dihydroisatropolone C;    spontaneous oxidation;   

DOI  :  10.3390/molecules27092882

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown