The alkaloids of Margaritaria indica. Part 2. The structures of 4-epiphyllanthine, margaritarine and the structural revision of securinol A

Journal of the Chemical Society, Perkin Transactions 1
1991.0

Abstract

In continuation of our work on the alkaloids of Margaritaria indica, we report on the constitution and stereochemistry of the minor bases of the bark of this West Sumatran tree. In addition to the known compounds securinine 1, allosecurinine 4 and (2α,15α)-14,15-dihydro-15-methoxysecurinan-11-one (14,15-dihydro-15α-methoxyphyllochrysine) 11 (isolation previously reported), we also isolated the known compounds (4α)-4-methoxysecurinan-11-one (phyllanthine) 2 and (2α,4α)-4-methoxysecurinan-11-one (securitinine) 5, identified by their physical and spectroscopic properties in accord with literature records. We also isolated the known alkaloid securinol A, originally assigned structure 14 but now revised to structure 17. Furthermore, we report the structures of the new alkaloids (4α)-4-methoxysecurinan-11-one (4-epiphyllanthine) 3 and 3-{N-[(2α,15α)-14,15-dihydro-11-oxosecurinan-15-yl]-2-aminoethyl}-1H-indole 10, whose structures were deduced from their spectroscopic properties. High field NMR spectra for the known Securinega alkaloids (4α)-4-methoxysecurinan-11-one 2 and (2α,4α)-4-methoxysecurinan-11-one 5 were recorded and interpreted. The structure of the known alkaloid securinol A is revised to 17 as a result of an X-ray crystal structure determination of its hydrobromide.

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