Isolation of a New Caryophyllane Ester fromLactarius subumbonatus: Conformational Analysis and Absolute Configuration

Abstract

(1R,6R,9S)‐6‐Hydroxycaryophyllene (S)‐6‐hydroxystearate, a sesquiterpene alcohol esterified by the unusual fatty acid (S)‐(+)‐6‐hydroxystearic acid, has been isolated from the fruiting bodies of the Basidiomycete Lactarius subumbonatus. Both NMR data and AM1 calculations indicate that the caryophyllene macrocyclic ring adopts a ββ conformation. The absolute configuration of the sesquiterpene moiety has been established by theoretical Circular Dichroism calculations (De Voe coupled oscillators theory) and that of the fatty acid by NMR studies of the (R)‐2‐methoxy‐2‐naphthylacetic acid (2‐NMA) ester.

Volatile sesquiterpenes from fungi: what are they good for?

“…These products are chemically very reactive, hence toxic on the one hand but instable on the other hand (Sterner et al 1985). Some of them are volatiles acting as repellents or kairomones (messengers for interspecies communication that just benefit the receiving organisms) (Raudaskoski and Kothe 2010;Bahn et al 2007 (Clericuzio et al 1999). The toxicity of this metabolite was tested against the brine shrimp Artemia salina.…”