New α-pyrones produced by fungal culture LL-11G219 function as androgen receptor ligands

Abstract This report describes the isolation and characterization of several closely related compounds, produced by fungal culture LL-11G219, with androgen-like activity. Bioassay-guided isolation yielded four novel fermentation products of the α-pyrone class: 11G219α, β, γ, and δ. Structures were assigned to these compounds on the basis of spectroscopic data, particularly those from 1D and 2D NMR experiments. α-Pyrones bearing an olefinic side chain in conjunction with a 6-alkyl substitution were hitherto unknown.