A. Arnone et al., SECONDARY MOLD METABOLITES .47. ISOLATION AND STRUCTURE ELUCIDATION OF CLAVILACTONES AC, NEW METABOLITES FROM THE FUNGUS CLITOCYBE CLAVIPES, Journal of the Chemical Society. Perkin transactions. I, (15), 1994, pp. 2165-2168
Clavilactones A-C (1, 4 and 5) have been isolated from cultures of the
Basidiomycetous fungus Clitocybe clavipes. Their structures and relat
ive configurations have been deduced from H-1 and C-13 NMR studies, ch
emical reactions and single-crystal X-ray analysis of the dimethyl eth
er derivative 3. H-1-H-1 coupling constants, NOE data and molecular mo
delling calculations all-suggest that the molecules have little confor
mational mobility and the conformation adopted in solution by clavilac
tone A 1 and dimethyl ether derivative 3 is essentially identical with
that of 3 in the solid state. Clavilactones A-C exhibit antifungal an
d antibacterial activity and inhibit the growth germination of Lepidiu
m sativum. A possible biogenetic origin of clavilactone A 1 is discuss
ed.