Mahanimbine, from carbazole alkaloid

Dineshkumar B, Mitra A, Mahadevappa M. (2010) Antidiabetic and hypolipidemic effects of mahanimbine (carbazole alkaloid) from Murraya koenigii (rutaceae) leaves. Int J Phytomed 2 22-30. 

From the stem bark, a new carbazole derivative, named murrayanine, has been isolated. It has been formulated as l-methoxy-3-formylcarbazole (I) (Chakraborty et al., 1965). Roy and Chakraborty (1974) reported the isolation of mahanimbine. The structure of a new hexacyclic carbazole alkaloid, isomur-rayazoline, from stem bark has been shown to be 9a,10,11,12,13,13a-hexahydro-5,9,9,12-... 

Five carbazole alkaloids isolated from the CH2C12 extract and their structures, namely, euchrestine B (compound 1), bismurraya-foline E (compound 2), mahanine (compound 3), mahanimbicine (compound 4) and mahanimbine (compound 5), exhibited antioxidative properties (Nakatani, 2000 Tachibana et al., 2001). The levels of antioxidant vitamins in fresh curry leaves were... 

The three bioactive carbazole alkaloids, e.g. mahanimbine, murrayanol and maha-nine, were found to be mosquitocidal and antimicrobial. The antioxidant activity of carbazoles (l,l-diphenyl-2-picryl hydrazyl DPH) from M. koenigii was found to be in order ascorbic acid > bismurraya foline E > euchestine B, mahanine and a-tocopherol... 

Carbazole alkaloids have been isolated from a few Rutaceae species, especially Murraya koenigii, the leaves of which have been used in southern India as a flavoring in food. Murrayanine, mukoeic acid, girinimbine, and mahanimbine have been isolated from the leaves. Carbazole alkaloids occur in all parts of this plant. 

Non-tryptamines.—In the Murray a carbazoles area, more details2 of the structural work on murrayacine1" (la) have been given. The alkaloid isomahanimbine1" (lb) has unfortunately been given a second name, mahanimbicine, in an independent structure determination.3 The hexacyclic bicyclomahanimbicine was also isolated in this investigation 3 it is related to the tetracyclic mahanimbicine ( = isomahanimbine) as bicyclomahanimbine is1" to mahanimbine, and can likewise be obtained from the tetracyclic compound by acid treatment... 

Reviews have been published on Rhazyal and indoline Vinca alkaloids, and a book d has been devoted to the chemistry, botany, folklore, and biological activities associated with Vinca species. A table surveys all the Rutaceae species so far studied and lists the alkaloids obtained therefrom canthinone, euxylo-phorine, and pyrano-carbazoles of the murrayacine-mahanimbine series have been obtained from this family. 

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