The chemical constituents of Australian Flindersia species. XIX. Triterpenoids from the leaves of F. bourjotiana F. Muell

Abstract

From the leaves of Flindersia bourjotinna F. Muell. there were isolated sitosterol, triacontanol, lupeol, germanicol, germanicone, and four new triterpenoids, the bourjotinolones A, B, and C, and bourjotone. By chemical degradation and spectroscopic methods, the structures of these substances were shown to be 21,24-epoxy-23,25-dihydroxytirucall-7-en-3one, 23,24-dihydroxytirucalla-7,25-dien- 3-one, 25-chloro-23,24-dihydroxytirucall-7-en-3-one, and 25,26,27-trisnortirucall-7- ene-3,23-dione, respectively. Bourjotinolone C is almost certainly an artefact but bourjotinolone B and bourjotone are less likely to be. From biogenetic and N.M.R. spectral considerations, the absolute stereochemistry of the new triterpenes may be deduced.