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Di-Isatropolone C, a Spontaneous Isatropolone C Dimer Derivative with Autophagy Activity.

ABSTRACT: Isatropolone C from Streptomyces sp. CPCC 204095 features a fused cyclopentadienone-tropolone-oxacyclohexadiene tricyclic moiety in its structure. Herein, we report an isatropolone C dimer derivative, di-isatropolone C, formed spontaneously from isatropolone C in methanol. Notably, the structure of di-isatropolone C resolved by NMR reveals a newly formed cyclopentane ring to associate the two isatropolone C monomers. The configurations of four chiral carbons, including a ketal one, in the cyclopentane ring are assigned using quantum NMR calculations and DP4+ probability. The plausible molecular mechanism for di-isatropolone C formation is proposed, in which complex dehydrogenative C-C bond coupling may have happened to connect the two isatropolone C monomers. Like isatropolone C, di-isatropolone C shows the biological activity of inducing autophagy in HepG2 cells.

SUBMITTER: Fu J

PROVIDER: S-EPMC11013608 | biostudies-literature | 2024 Mar

REPOSITORIES: biostudies-literature

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Di-Isatropolone C, a Spontaneous Isatropolone C Dimer Derivative with Autophagy Activity.

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

Molecules (Basel, Switzerland) 20240326 7

Isatropolone C from <i>Streptomyces</i> sp. CPCC 204095 features a fused cyclopentadienone-tropolone-oxacyclohexadiene tricyclic moiety in its structure. Herein, we report an isatropolone C dimer derivative, di-isatropolone C, formed spontaneously from isatropolone C in methanol. Notably, the structure of di-isatropolone C resolved by NMR reveals a newly formed cyclopentane ring to associate the two isatropolone C monomers. The configurations of four chiral carbons, including a ketal one, in the ...[more]

PMID: 38611756

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Dataset Information

Di-Isatropolone C, a Spontaneous Isatropolone C Dimer Derivative with Autophagy Activity.

Publications

Di-Isatropolone C, a Spontaneous Isatropolone C Dimer Derivative with Autophagy Activity.

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