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- Title
Di-Isatropolone C, a Spontaneous Isatropolone C Dimer Derivative with Autophagy Activity.
- Authors
Fu, Jie; Liu, Xiaoyan; Zhang, Miaoqing; Liu, Jiachang; Li, Shufen; Jiang, Bingya; Wu, Linzhuan
- 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.
- Subjects
AUTOPHAGY; COUPLING reactions (Chemistry); CYCLOPENTANE; MONOMERS; STREPTOMYCES
- Publication
Molecules, 2024, Vol 29, Issue 7, p1477
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules29071477