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二氢异阿朴啡酮 C 来源于 和其对异阿朴啡酮生物合成中 tropolone 环构建的意义。

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

机构信息

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.

出版信息

Molecules. 2022 Apr 30;27(9):2882. doi: 10.3390/molecules27092882.

Abstract

Isatropolones/isarubrolones are actinomycete secondary metabolites featuring a tropolone-ring in their structures. From the isatropolone/isarubrolone producer sp. CPCC 204095, 7,12-dihydroisatropolone C (HITC) 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 sp. CPCC 204095, HITC can be oxidized spontaneously to isatropolone C (ITC), suggesting HITC is the physiological precursor of ITC. Characterization of HITC makes us propose dihydrotropolone-ring construction in the biosynthesis of isatropolones.

摘要

异茨醇酮/异红没药醇酮是放线菌的次级代谢产物,其结构中具有三酮环。从异茨醇酮/异红没药醇酮的产生菌 sp. CPCC 204095 中发现并鉴定了 7,12-二氢异茨醇酮 C(HITC),它是两种可互换的非对映异构体的混合物,其区别在于 C-6 构型。作为 sp. CPCC 204095 丝状生长阶段的主要代谢产物,HITC 可以自发氧化为异茨醇酮 C(ITC),这表明 HITC 是 ITC 的生理前体。HITC 的特性使我们提出在异茨醇酮的生物合成中存在二氢三酮环的构建。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bffc/9099902/fbe53b163eec/molecules-27-02882-g001.jpg

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