Fusaristatins D–F and (7S,8R)-(−)-chlamydospordiol from Fusarium sp. BZCB-CA, an endophyte of Bothriospermum chinense

Abstract

Three new lipodepsipeptides, fusaristatins D–F ( 1 – 3 ) and a new α -pyrone derivative, (7 S ,8 R )-(−)-chlamydospordiol ( 5 ), together with eight known compounds ( 4 , 6 – 12 ) were obtained from solid rice cultures of Fusarium sp. BZCB-CA, an endophyte of the Chinese medicinal plant, Bothriospermum chinense . The planar structures of the new metabolites ( 1 – 3 , 5 ) were established by spectroscopic techniques (1D/2D NMR and HRESIMS). Marfey’s method was applied to determine the absolute configuration of 1 , while the absolute configuration of 5 was determined by single-crystal X-ray crystallography analysis in addition to Mosher’s method. Crystallographic data of inflatin C ( 7 ) are also supplied here for the first time. In cytotoxicity assays, rubrofusarin ( 8 ) showed a moderate effect on the lymphoma cell lines L5178Y, Ramos and Jurkat, with IC 50 values of 7.7, 6.2 and 6.3 μ M, respectively, while the remaining compounds were inactive. When subjected to antibacterial assay, only lateropyrone ( 9 ) exhibited good to weak activity against a panel of Gram-positive bacteria including drug-resistant strains with MICs ranging from 3.1 to 25 μ M. • Fermentation of Bothriospermum chinense yielded three new lipodepsipeptides. • One new α -pyrone derivative was obtained. • Rubrofusarin showed moderate cytotoxicity on cell lines L5178Y, Ramos and Jurkat.