Alkaloids of Geijera salicifolia Schott. (family Rutaceae): The identification of platydesmine and platydesmine acetate

Australian Journal of Chemistry
1966.0

Abstract

Geijera salicifolia Schott., a tree of moderate size belonging to the family Rutaceae widely distributed in the coastal area of central and southern Queensland and in New Guinea, had no alkaloids detected in its bark in an earlier chemical examination but a new coumarin (6-isovaleryl-7 methoxycoumarin) was identified. Leaves of G. salicifolia gave a positive field test for alkaloids, and alkaloids were isolated in 0.48% yield from a sample of leaves collected in New Guinea. Two leaf alkaloids were identified as the furoquinolines skimmianine and γ-fagarine (isolated from many rutaceous genera), while two other leaf alkaloids were isopropyldihydrofuroquinolines. The major one was identified as platydesmine (previously from Platydesma campandata) based on comparison of physical and spectroscopic properties with published data and confirmed by chemical degradation to products consistent with its known structure. The minor base, C₁₇H₁₉NO₄, was shown to be platydesmine acetate via spectroscopic data (infrared bands typical of acetate ester, NMR with OCOCH₃ singlet and no exchangeable protons), hydrolysis to platydesmine under mild alkaline conditions, and preparation from platydesmine by acetylation. It appears to be the first example of an acetate ester within this group of alkaloids, although 1-acetoxy-2-n-propylquinol-4-one has been isolated from Boroniu ternata A. Cum. (Rutaceae).

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