M. Clericuzio et al., Fungal metabolites, 44 - Isolation of a new caryophyllane ester from Lactarius subumbonatus: Conformational analysis and absolute configuration, EUR J ORG C, (9), 1999, pp. 2059-2065
(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.