7-Methoxyglycomaurin: A New Carbazole Alkaloid fromGlycosmis rupestris

Planta Medica
1998.0

Abstract

In continuation of our work on the local Rutaceae family, we have investigated the constituents of the bark of Glycosmis rupestris Ridely collected from Langkawi Island and used medicinally, especially the roots, for the treatment of fever, swollen spleen, and as a stimulant to digestion (1, 2). A voucher specimen has been deposited at the herbarium, Department of Botany, Universiti Kebangsaan Malaysia. Previous studies of this genus have revealed the presence of various compounds such as alkaloids, coumarins, and sulphur-containing amides from plant materials collected in Sri Lanka, India, Thailand, and also Malaysia (3—5). In this work we report the isolation and identification of a new carbazole alkaloid 7-methoxyglycomaurin (1) and the known glycomaurin and de-N-methylacronycine from G. rupestris Ridely. The ground air-dried bark(1.53kg) of the plant was extracted with CHCI3 twice and the combined extract was concentrated to give 25 g dark gummy solid. The extract (19 g) was purified by column chromatography on silica to give the compounds. The UV spectrum of 1 with absorptions at 235, 240, 256, 293, and 334 nm is characteristic of a carbazole nucleus, while its IR spectrum with an absorption at 3386 cm⁻¹ indicated an NH group. The MS gave the molecular ion at m/z 293 (molecular formula C₁₉H₁₉NO₂). A complete ¹H-NMR spectral assignment (substantiated by NOESY) supported the structure of 7-methoxyglycomaurin, a carbazole alkaloid with a skeleton proposed by Kumar et al. (6). Identification of all compounds was achieved by UV, IR, mass, ¹H- and ¹³C-NMR spectroscopy.

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