Highly oxidized ergosterols and isariotin analogs from an entomopathogenic fungus, Gibellula formosana, cultivated in the presence of epigenetic modifying agents
作者： Teigo Asai , Yu-Ming Chung , Hiroaki Sakurai , Tomoji Ozeki , Fang-Rong Chang
DOI: 10.1016/J.TET.2012.05.020
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摘要: Abstract The concomitant addition of a histone deacetylase inhibitor, suberoyl bis-hydroxamic acid, and DNA methyltransferase RG-108, to the culture medium Gibellula formosana, an entomopathogenic fungus, induced significant increase in diversity secondary metabolites. From media were isolated two new highly oxidized ergosterols, formosterols A (1) B (2), five isariotin analogs, 12′-O-acetylisariotin (4), 1-epi-isariotin (5), isariotins K–M (6–8), together with 22,23-epoxy-3,12,14,16-tetrahydroxyergosta-5,7-dien-11-one (named formosterol C) (3), (9), C (10), E (11), TK-57-164A (12), beauvericin (13). NMR spectra, X-ray single crystallographic diffraction, chemical transformations revealed structures isariotins. stereochemistry (3) was deduced from its spectroscopic data. side chains A–C (1–3) contained cis-22,23-epoxide, which is rarely present naturally occurring sterols triterpenes.
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