Abstract
Cultivation of a deep-sea-derived fungus Eutypella sp. MCCC 3A00281 by a chemical epigenetic manipulation using suberohydroxamic acid (SBHA), a histone deacetylase inhibitor (HDI), resulted in the significant change of the metabolite profile. Chromatographic application of the extended metabolites led to the isolation of a total of 30 eremophilane-type sesquiterpenoids, of which 26 were identified as new entities namely eutyperemophilanes A-Z (1–26). Their structures were established by extensive analyses of the 1D and 2D NMR, and HRESIMS data, as well as the modified Mosher's method, X-ray crystallography, and ECD data for the assignment of their absolute configurations. Most eremophilanes from the fungal strain showed a trans-fusion of rings A and B, uncommonly found from nature. All compounds were evaluated for the inhibitory effects toward the nitric oxide (NO) production that was induced by lipopolysaccharide (LPS) in RAW 264.7 macrophage cells, while compounds 9 and 10 exerted significant inhibition.
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