Lupeol.
The title compound [systematic name: 3beta-lup-20(29)-en-3-ol], C(30)H(50)O, was isolated from the leaves of Garcinia 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 in trans fashion. Lupeol is isomorphic with the pentacyclic triterpene 3beta,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 the c axis.
Corrêa
Rodrigo S
RS
Instituto de Física de São Carlos, Universidade de São Paulo, 13560-970, São Carlos, SP, Brazil. rodrigocorrea@ursa.ifsc.usp.br
Coelho
Carla P
CP
dos Santos
Marcelo H
MH
Ellena
Javier
J
Doriguetto
Antônio C
AC
D018360:Crystallography, X-Ray; D029760:Garcinia / Q000737:chemistry; D015394:Molecular Structure; D053978:Pentacyclic Triterpenes; D014315:Triterpenes / Q000737:chemistry*; D000094042:Lupanes
D053978:Pentacyclic Triterpenes; D014315:Triterpenes; C010480:lupeol; D000094042:Lupanes