Lupeol

Abstract

The title compound [systematic name: 3β-lup-20(29)-en-3-ol], C30H50O, was isolated from the leaves ofGarcinia brasiliensis(common name: bacupari; a member of the Guttiferae family) and has been shown to have many useful medicinal and biological properties. The lupeol molecule consists of four six-membered rings (adopting chair conformations) and one five-membered ring (with an envelope conformation), all fused intransfashion. Lupeol is isomorphic with the pentacyclic triterpene 3β,30-dihydroxylup-20(29)-ene, which differs from lupeol due to the presence of an additional hydroxy group. The crystal packing is stabilized by van der Waals interactions and intermolecular O—H...O hydrogen bonds, giving rise to an infinite helical chain along thecaxis.