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Alkaloidal constituents of root and stem bark of Murraya koenigii (L.) SPRENG. (Rutaceae) grown in the green-house of Okitsu Branch, Fruit Tree Research Station, Shizuoka, were studied. Three new monomeric and five novel binary carbazole alkaloids named mukoenine-A (1), -B (2), and -C (4), and murrastifoline-F (8), bis-2-hydroxy-3-methylcarbazole (9), bismahanine (11), bikoeniquinone-A (12), and bismurrayaquinone-A (13), respectively, were isolated, as well as 16 kinds of known carbazoles and carbazolequinones, and their structures were elucidated by spectrometric methods. Among the new binary carbazoles, bikoeniquinone-A (12) and bismurrayaquinone-A (13) were found to contain a carbazole-1, 4-quinone skeleton as a basic structural unit. These are the first examples of binary carbazolequinone alkaloids to be found in nature, and also the first carbazolequinone alkaloids to be isolated from Murraya plants except for M. euchrestifolia.
Ito et al. (1993) studied this question.