Fusaristatins D–F and (7S, 8R)-(−)-chlamydospordiol from Fusarium sp. BZCB-CA, an endophyte of Bothriospermum chinense. (9th April 2021)

• Record Type: Journal Article
• Authors: Ariantari, Ni Putu; Frank, Marian; Gao, Ying; Stuhldreier, Fabian; Kiffe-Delf, Anna-Lene; Hartmann, Rudolf; Höfert, Simon-Patrick; Janiak, Christoph; Wesselborg, Sebastian; Müller, Werner E.G.; Kalscheuer, Rainer; Liu, Zhen; Proksch, Peter
• Is Part Of: Tetrahedron. Volume 85(2021)
• Publication Date: 2021-04-09
• Subjects: Endophyte -- Fusarium sp. -- Lipodepsipeptide -- Fusaristatin -- Cytotoxicity -- Antibacterial activity; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2021.132065
• Languages: English
• ISSNs: 0040-4020

Abstract

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 IC50 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. Graphical abstract: Image 1 Highlights: 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.