Two novel secoergosterols, 3 beta-hydroxy-8 alpha,9 alpha-oxido-8,9-secoerg
osta-7,9(11),22-triene (tylopiol A) (1) and 3 beta-hydroxy-8 alpha,9 alpha-
oxido-8,9-secoergosta-7,22dien-12-one (tylopiol B) (2), were isolated from
the fresh fruit bodies of Tylopilus plumbeoviolaceus, along with three know
n compounds, ergosta-7,22-dien-3 beta-ol, uridine, and allitol. Their struc
tures were elucidated by NMR techniques, including H-1 NMR, C-13 NMR, HMQC,
HMBC, and MS. The structure and stereochemistry of compound 1 were demonst
rated by X-ray crystallography.