A strain of Fusarium semitectum Berk. & Rav. from maize stalk rot in southern Italy produced bioactive metabolites when cultured on autoclaved rice kernels at room temperature for 4 weeks. The organic extracts of fungal culture showed a strong antibiotic activity towards Geotrichum candidum in disk diffusion assays, but they were not toxic to Artemia salina larvae. Two antifungal metabolites were isolated and characterized by chemical and spectroscopic methods as two 3-substituted-4-hydroxy-6-alkyl-2-pyrones, in particular, the 3-(4-deoxy-β-xylo-hexopyranosyl)-4-hydroxy-6-[2-hydroxy-7-hydroxymethyl-1,1,5,9,11-pentamethyl-3,5,8-heptadecatrienyl]-2H-pyran-2-one and its 6-[2-hydroxy-1,1,5,7,9,11-hexamethyl] analog, which were named fusapyrone and deoxyfusapyrone, respectively.
4-hydroxy-6-alkyl-2-pyrones, antifungal metabolites, Fusarium semitectum, Geotrichum candidum assay
NCBI PubMed ID: 8032694Publication DOI: 10.1002/nt.2620020103Journal NLM ID: 9212382Publisher: New York, NY: Wiley-Liss, Inc.
Institutions: Dipartimento di Scienze Chimico-Agrarie, Università di Napoli ''Federico II'', Portici, Italy, Istituto Tossine E Micotossine Da Parassiti Vegetali Del CNR, Bari, Italy, Istituto di Patologia Vegetale, Università degli Studi, Sassari, Italy, Dipartimento di Chimica, Università della Calabria, Arcavacata, Italy, Istituto di Strutturistica Chimica ''G. Giacomello'' del CNR, Rome, Italy
Methods: 13C NMR, 1H NMR, NMR-2D, IR, FAB-MS, TLC, ESI-MS, biological assays, alkaline hydrolysis, UV, extraction, optical rotation measurement, CC, cell growth