Preparative-scale fermentation of hypoestenone (1) with Mucor ramannianus (
ATCC 9628) has resulted in the isolation of 8(9)alpha -epoxyhypoestenone (2
) and the new metabolites 8(9)alpha -epoxy-12,13-anhydrohypoestenone (3), 1
7-hydroxyhypoestenone (4), 13 alpha ,18-dihydroxyhypoestenone (5), and 13 b
eta ,18-dihydroxyhypoestenone (6). Structure elucidation of these metabolit
es was based primarily on 1D and 2D NMR analyses.