Fungal metabolites, 44 - Isolation of a new caryophyllane ester from Lactarius subumbonatus: Conformational analysis and absolute configuration

(1R,GR,SS)-6-Hydroxycaryophyllene (S)-6-hydroxystearate, a sesquiterpene al cohol esterified by the unusual fatty acid (S)(+)-6-hydroxystearic acid, ha s been isolated from the fruiting bodies of the Basidiomycete Lactarius sub umbonatus. Both NMR data and AM1 calculations indicate that the caryophylle ne macrocyclic ring adopts a beta beta conformation. The absolute configura tion of the sesquiterpene moiety has been established by theoretical Circul ar Dichroism calculations (De Voe coupled oscillators theory) and that of t he Salty acid by NMR studies of the (R)-2-methoxy-2-naphthylacetic acid (2- NMA) ester.