首页|Phomaketals A and B,pentacyclic meroterpenoids from a eupC overexpressed mutant strain of Phoma sp.

Phomaketals A and B,pentacyclic meroterpenoids from a eupC overexpressed mutant strain of Phoma sp.

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Phomaketals A(1)and B(2),two tropolonic meroterpenoids with the unprecedented pentacyclic skele-tons,were isolated from the solid-substrate fermentation cultures of a eupC overexpressed mutant strain of the fungus Phoma sp.,together with a biogenetically related secondary metabolite pughiinin B(3),and the known one noreupenifeldin B(4).The structures of 1-3 were elucidated primarily by nuclear magnetic resonance(NMR)experiments.The absolute configurations of 1 and 2 were assigned by elec-tronic circular dichroism calculations and the calculated NMR with DP4+analysis,while that of 3 was established by single-crystal X-ray diffraction analysis using Cu Kα radiation.Biogenetically,phomaketals A(1)and B(2)could be derived from the hypothetical tropolonic sesquiterpene intermediates neose-tophomone B(6)and 9-R-neosetophomone B(6′),respectively,via different reactions cascades.Com-pound 1 showed antiproliferative effect only against the SUPB15 cells,with an 50% inhibitory concentra-tion(IC50)value of 4.85μmol/L,while the co-isolated known meroterpenoid 4 displayed potent effects against three tumor cell lines,SUPB15,EL4,and H9,showing IC50 values of 0.36-27.08 μmol/L.

Phoma sp.Tropolonic sesquiterpenesBiosynthetic pathwaysHetero-Diels-AlderCytotoxicity

Chuan Li、Yangyang Han、Yanan Zhai、Ke Li、Xingzhong Liu、Zhuan Zhang、Cai Jia、Yongsheng Che

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NHC Key Laboratory of Biotechnology of Antibiotics,Institute of Medicinal Biotechnology,Chinese Academy of Medical Sciences&Peking Union Medical College,Beijing 100050,China

State Key Laboratory of Toxicology&Medical Countermeasures,Beijing Institute of Pharmacology&Toxicology,Beijing 100850,China

Department of Microbiology,College of Life Sciences,Nankai University,Tianjin 300071,China

National Natural Science Foundation of ChinaCAMS Innovation Fund for Medical SciencesCAMS Innovation Fund for Medical SciencesCAMS Innovation Fund for Medical Sciences

820036282021-I2M-1-0302021-I2M-1-0282021-1-I2M-2-002

2024

中国化学快报(英文版)
中国化学会

中国化学快报(英文版)

CSTPCD
影响因子:0.771
ISSN:1001-8417
年,卷(期):2024.35(7)