AI Article Synopsis
- Isatropolone C is a compound with a complex tricyclic structure derived from a specific microbial species and has been shown to dimerize into di-isatropolone C in methanol.
- The NMR analysis of di-isatropolone C reveals a new cyclopentane ring connecting two isatropolone C molecules and provides insights into the configuration of its chiral carbons using advanced quantum calculations.
- Both isatropolone C and di-isatropolone C have been found to induce autophagy in HepG2 liver cancer cells, indicating their potential biological significance.
Article Abstract
Isatropolone C from 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.
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Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11013608 | PMC |
| http://dx.doi.org/10.3390/molecules29071477 | DOI Listing |
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