Novel binary carbazole alkaloids from Murraya euchrestifolia.

Chemical and Pharmaceutical Bulletin
1990.0

Abstract

As part of a continuing phytochemical investigation of Murraya plants, nine binary carbazole alkaloids, as well as various monomeric carbazoles and carbazolequinones, had previously been isolated and characterized from Murraya euchrestifolia HAYATA. This paper deals with the isolation and structural elucidation of another seven new binary carbazole alkaloids from the root bark of M. euchrestifolia collected in Taiwan in February 1980. The seven new alkaloids were named murrastifoline-A (1), -B (2), -C (3), -D (4) and chrestifoline-A (5), -B (6), -C (7). The acetone extract of the root bark was subjected successively to silica gel column chromatography and preparative thin-layer chromatography (TLC) to obtain these compounds. Their structures were elucidated by means of spectral methods including ultraviolet (UV) spectroscopy, proton nuclear magnetic resonance (¹H-NMR) with proton-proton correlation spectroscopy (H-H COSY), nuclear Overhauser effect (NOE) experiments, and high resolution mass spectrometry (HR-MS). A common N-substituted 1-methoxy-3-methylcarbazole structural unit was identified in the four murrastifolines (1-4) based on spectral data, and the complete structures of all seven alkaloids were determined through detailed analysis of their spectral information.

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