The Chemistry of the Western Australian Rutaceae. III. The Alkaloids of Boronia ternata Endl

Australian Journal of Chemistry
1963.0

Abstract

In Western Australia, Boronia ternata Endl is an exception among Boronia species (Rutaceae) that occurs in arid and semi-arid regions, prompting a preliminary examination of its constituents. Ether extraction of leaves yielded an alkaloid mixture containing 1-acetoxymethyl-2-n-propyl-4-quinolone (C15H17NO3) and skimmianine. The structure of 1-acetoxymethyl-2-n-propyl-4-quinolone was confirmed by infrared (ester at 1740 cm-1, conjugated carbonyl at 1640 cm-1), ultraviolet, and 60 Mc/s nuclear magnetic resonance (n.m.r.) spectra, which revealed acetoxymethyl, propyl, and quinolone moieties. Methanol extraction produced 2-n-propyl-4-quinolone (C12H13NO), identified as an artifact from 1-acetoxymethyl-2-n-propyl-4-quinolone via alkali (yielding formaldehyde, acetic acid, and the artifact) or hydrogen chloride treatment. The occurrence of 2-n-propyl-4-quinolone completes the series of odd-numbered homologous chains (up to undecyl) in Rutaceae alkaloids, consistent with biogenesis via anthranilic ester and β-ketoacid as proposed by Cornforth and James.

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