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Review | Regular issue | Vol 4, No. 2, 1976, pp.429-451
Published online, 1st January, 1970
DOI: 10.3987/R-1976-02-0429
Studies on Indole Alkaloid Biosynthesis. Part II. Alkaloids Lacking the Normal Tryptophan Side Chain

James P. Kutney*

*Department of Chemisry, University of British Columbia, Vancouver 8, V5T 1W5 , Canada

Abstract

A summary of experiments relating to the biosynthesis of apparicine (II) and uleine (I) is presented. These alkaloids which lack the two carbon unit normally derived from tryptophan provide an interesting comparison with the Aspidosperma and Iboga bases for which a considerable amount of biosynthetic data has been accumulated. It is shown that tryptophan is utilized by the plant (Aspidosperma pyricollum) to provide the indole unit and the one carbon bridge between the β-position of the indole and the basic nitrogen atom in apparicine. Secodine is also incorporated intact into this alkaloid but the levels of incorporation are low. Interpretation of these results and their implications for future experiments are also provided. Preliminary experiments relating to the biosynthesis of olivacine (III, R = H; R’ - CH3) and guatambuine (XV) are presented.