Coprinolone and Δ⁶-coprinolone: new sesquiterpenes from <i>Coprinus psychromorbidus</i>

Abstract

The structure of coprinolone (1), an oxygen-bridged protoilludane from the W2 isolate of the fungus Coprinuspsychromorbidus, has been elucidated by chemical transformations and detailed 1 H and 13 C magnetic resonance studies, including homo- and heteronuclear correlation spectra. The 1 H– 1 H coupling data and nuclear Overhauser difference spectra for 1 and derived isomers led to the establishment of its stereochemistry. A second metabolite was identified as Δ 6 -coprinolone (20) by spectroscopic results. Confirmatory evidence in support of the structures was obtained from the labelling patterns of the compounds from cultures supplemented with sodium [1,2- 13 C 2 ]acetate. Keywords: coprinolone, Δ 6 -coprinolone, protoilludane, sesquiterpenes, NMR.