The chemical constituents of Australian Flindersia species. XXI. An examination of the bark and the leaves of F. laevicarpa

Abstract

From extracts of the bark of Flindersia laevicarpa C. T. White & Francis (Rutaceae), the known substances lupeol, β-sitosterol, hesperidin and salicylic acid were isolated together with eight othersubstances. Three of them, flindercarpin-1, C_25,H₂₂O₁₁, flindercarpin-2, C₃₂H₄₀O₁₃,and flindercarpin-3, C₂₆H₃₂O₉, were reserved for further study. The others were shown to be (-)-nerolidol,(+)-threo-1,5-diphenylpentane-1,3-diol, 2-(2-pheny1ethyl)chromone (flindersiachromone), its 2,3-dihydro derivative, and its 8-methoxy derivative (8-methoxyflindersiachromone).The leaves yielded hesperidin, flindercarpin-2, harmalan and five other products. A triterpene, flindersolide, C₃₀H₄₈O₄, was reserved for further study. Acetylation of the harmalan mother liquors gave acetylharmalan, a mixture of dimers of the latter and also N-[2-(2-acetyl-3-indolyl)ethyl]acetamide, all of which are artefacts. The remaining substance, a flavone, carpachromene, C₂₀H₁₆O₅, was shown to be 5-hydroxy-8-(4-hydroxyphenyl)-2,2-dimethyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one.