2. Academic Validation
  3. Ascomylactams A-C, Cytotoxic 12- or 13-Membered-Ring Macrocyclic Alkaloids Isolated from the Mangrove Endophytic Fungus Didymella sp. CYSK-4, and Structure Revisions of Phomapyrrolidones A and C

Ascomylactams A-C, Cytotoxic 12- or 13-Membered-Ring Macrocyclic Alkaloids Isolated from the Mangrove Endophytic Fungus Didymella sp. CYSK-4, and Structure Revisions of Phomapyrrolidones A and C

  • J Nat Prod. 2019 Jul 26;82(7):1752-1758. doi: 10.1021/acs.jnatprod.8b00918.
Yan Chen 1 2,  Zhaoming Liu 1 3,  Yun Huang 4 5,  Lan Liu 2,  Jianguo He 2,  Lan Wang 5,  Jie Yuan 4,  Zhigang She 1 2
Affiliations

Affiliations

  • 1 School of Chemistry , Sun Yat-sen University , Guangzhou 510275 , People's Republic of China.
  • 2 School of Marine Sciences, Sun Yat-sen University , South China Sea Bio-Resource Exploitation and Utilization Collaborative Innovation Center , Guangzhou 510006 , People's Republic of China.
  • 3 Guangdong Institute of Microbiology , Guangzhou 510075 , People's Republic of China.
  • 4 Department of Biochemistry, Zhongshan School of Medicine , Sun Yat-sen University , Guangzhou 510080 , People's Republic of China.
  • 5 Department of Pathogen Biology and Immunology, School of Basic Courses , Guangdong Pharmaceutical University , Guangzhou 510006 , People's Republic of China.
PMID: 31251621 DOI: 10.1021/acs.jnatprod.8b00918
Abstract

Three new 12- or 13-membered-ring macrocyclic Alkaloids, named ascomylactams A-C (1-3), along with the analogues phomapyrrolidone C (4) and phomapyrrolidone A (5) were isolated from the mangrove endophytic fungus Didymella sp. CYSK-4. Their structures were elucidated by analysis of extensive spectroscopic data and mass spectrometric data. The structures and absolute configurations of 1 and 2 were determined by single-crystal X-ray diffraction experiments, which represents the first crystal structures described for a (6/5/6/5) tetracyclic skeleton fused with a 12- or 13-membered-ring macrocyclic moiety. The configurations of phomapyrrolidone C (4) and phomapyrrolidone A (5) were revised by detailed analysis of the NMR data. In a cytotoxic assay, compounds 1 and 3 showed moderate cytotoxicity against MDA-MB-435, MDA-MB-231, SNB19, HCT116, NCI-H460, and PC-3 human Cancer cell lines, with IC50 values in the range of 4.2-7.8 μM.

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