The chemical constituents of Australian Zanthoxylum species. III. The constituents of Z. parviflorum Benth.; The structure of parvifloral; Some observations on the biogenesis of furoquinoline alkaloids

Abstract

The leaves of Zanthoxylum parviflorum Benth. yielded lupeol, sitosterol, and skimmianine; the bark gave sucrose, hesperidin, lupeol, skimmianine, chelerythrine chloride, (-)-α-canadine methiodide, and magnoflorine iodide. From the wood there were isolated hesperidin, sitosterol, dictamnine, skimmianine, platydesmine, and a new phenolic aldehyde, parvifloral. Spectroscopic data and biogenetic considerations suggested that parvifloral was 5-prenylconiferaldehyde, and the assignment of structure was confirmed by a rational synthesis. Oxidation of platydesmine with iodine/lead tetraacetate gave dictamnine. The significance of this result to the biogenesis of furoquinoline alkaloids is discussed.