1. Di-Isatropolone C, a Spontaneous Isatropolone C Dimer Derivative with Autophagy Activity.
- Author
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Fu, Jie, Liu, Xiaoyan, Zhang, Miaoqing, Liu, Jiachang, Li, Shufen, Jiang, Bingya, and Wu, Linzhuan
- Subjects
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AUTOPHAGY , *COUPLING reactions (Chemistry) , *CYCLOPENTANE , *MONOMERS , *STREPTOMYCES - 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. [ABSTRACT FROM AUTHOR]
- Published
- 2024
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