Murraya carbazole

Murraya exotica has yielded5 3-formylindole it would be intriguing to know if the biogenesis of this simple indole is related to that of the Murraya carbazoles, for which it has been postulated that the methyl-substituted c or a rings are derived from an indole by interaction with an isoprene unit. 

Fuostifoline (47), a furo[3,2-a]carbazole, was isolated from Murraya euchrestifolia. Timdri s total synthesis of 47 commenced with alkylation of bromocresol 43 with bromoacetaldehyde diethyl acetal and P4Oio-promoted cyclization to furnish 5-bromo-7-methylbenzofuran (44) [47]. The Suzuki coupling of boronic acid 45, derived from 44, with o-bromonitrobenzene yielded biaryl 46. Nitrene generation, achieved via deoxygenation of nitro compound 46 using triethyl phosphite, was followed by cyclization to fuostifoline (47). 

The dimeric carbazole alkaloids often occur along with the corresponding monomeric carbazoles in terrestrial plants [7,62] (Scheme 7). Clausenamine-A was obtained by Wu from the stem bark of Clausena excavata [63]. Clausen-amine-A and its synthetic analogs, like bis(O-demethylmurrayafoline-A), show cytotoxic activities against diverse human cancer cell lines [64] and exhibit moderate antimalarial activity [65,66]. Furukawa isolated l,r-bis(2-hy-droxy-3-methylcarbazole) and bismurrayaquinone-A, the first dimeric car-bazolequinone alkaloid found in nature, from Murraya koenigii [67]. 

Dineshkumar et al. investigated the antidiabetic efficacy of mahan-imbine (33), a carbazole alkaloid isolated from Murraya koenigii... 

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. 

The isolation of carbazole (1), 3-methylcarbazole (2), and several oxidized derivatives of 3-methylcarbazole from taxonomically related higher plants of the genera Glycosmis, Glausena, and Murraya (family Rutaceae) indicates that the aromatic methyl group of the biogenetic key intermediate 3-methylcarbazole can be eliminated oxidatively (5,6). Most of the carbazole alkaloids isolated from the... 

In 1988, Furukawa et al. isolated murrafoline-E (184) and murrafoline-F (185) from the root bark of M. euchrestifolia. Murrafoline-E was the third example of an N-benzyl-linked bis-carbazole alkaloid from a Murraya plant, while murrafoline-F was the first N-methoxy-bis-carbazole alkaloid (22). 

Wu et al. studied a range of natural carbazole alkaloids isolated from Murraya euchrestifolia for platelet aggregation inhibitory activity, and found that murrayamine A (7-hydroxygirinimbine, mukoenine-C) (120) (see Scheme 2.22) and murrayamine-M... 

The bis-carbazole alkaloids typically contain previously known monomeric carbazoles as structural subunits. To date, bis-carbazole alkaloids have been isolated from plants of two genera of the family Rutaceae, Murraya and Clausena, and are linked either by a methylene unit, a bisbenzylic ether bridge, a bond joining one aromatic portion directly to an annotated dihydropyran unit, or by a biaryl bond. Many reviews have appeared on the monomeric carbazole alkaloids. However, in these articles only a few bis-carbazole alkaloids were listed (3,5-7). For the first time, in 1992, Furukawa et al. compiled all of the bis-carbazole alkaloids that were known to the end of 1992 (158). Taster and Bringmann summarized to the end of 2001, the occurrence, stereochemistry, synthesis, and biological activity of the bis-carbazoles linked through a biaryl bond (159). We compiled to the mid of 2002, the occurrence, stereochemistry, synthesis, and the biological activity of all classes of bis-carbazoles (8). In this section, we cover the total syntheses of the natural bis-carbazole alkaloids reported since 1990. 

Recently, Tripathi et al. reported a new pyrano[3,2-a]carbazole alkaloid, 7-isovaleryl-oxy-8-methoxygirinimbine (1569) from the leaves of Murraya koenigii (896) (Scheme 6.2). 

Rahman, M. M. and Gray, A. I. 2005. A benzoisofuranone derivative and carbazole alkaloids from Murraya koenigii and their antimicrobial activity. Phytochemistry, 66 1601-1606. 

Biologically active carbazole alkaloids from Murraya koenigii. Journal of Agriculture and Food Chemistry, 47 444 47. 

The known alkaloid heptaphylline has been isolated from the roots of Clausena harmandiana Pierre (Rutaceae) along with two new carbazole alkaloids identified as 2-hydroxy-3-formyl-7-methoxycarbazole (58) and 7-methoxyheptaphylline (59). The H- and l3C-NMR spectra have been analyzed and used to position the various functional groups (54,55). Other carbazole alkaloids isolated from the roots of Murraya siamensis Craib are identified as murrayanine, girinimbine, and mukonal, which occur together with heptaphylline and compounds 58 and 59 (56-55). Three new alkaloids have also been isolated from M. siamensis and named 3-formyl-2,7-dimethoxycarbazole (60), 3-formyl-2-methoxylcarbazole (O-methylmukonal) (61), and 7-methoxymurrayacine (62) (59). From the roots of Rauwolfia serpentina, the new alkaloid indobine (63) (60), the benzyl ester, and indobinine (64) (61), the cyclohexyl ester of indolepropionic acid, have been isolated and identified. 

Anwer, F., Kapil, R.S. and Popli, S.P. (1 972) Terpenoid alkaloids from Murraya koenigiiVW. Synthesis of DL-O-methylmahanine and related carbazoles. Experientia 28, 769. 

Bhattacharya, L., Roy, S.K. and Chakraborty, D.P. (1982) Structure of the carbazole alkaloid isomurrayazoline from Murraya koenigii [stem bark]. Phytochemistry 21, 2432-2433. 

Bhattacharyya, P., Jash, S.S. and Chowdhury, B.K. (1 986) A biogenetically important carbazole alkaloid from Murraya koenigii Spreng. Chemistry and Industry 7, 246. 

Chakraborty, D.P., Barman, B.K. and Bose, P.K. (1 965) On the constitution of murrayanine, a carbazole derivative isolated from Murraya koenigii Spreng. Tetrahedron 21, 681-685. 

Chowdhury, B.K., Jha, S., Bhattacharyya, P. and Mukherjee, J. (2001) Two new carbazole alkaloids from Murraya koenigii. Indian Journal of Chemistry Section-B 40(6), 490 494. 

Fiebig, M., Pezzuto, J.M., Soejarto, D.D. and Kinghorn, A.D. (1 985) Koenoline, a further cytotoxic carbazole alkaloid from Murraya koenigii. Phytochemistry 24, 3041-3043. 

Ito, C., Thoyama, Y., Omura, M., Kajiura, I. and Furukawa, H. (1 993) Alkaloidal constituents of Murraya koenigii. Isolation and structural elucidation of novel binary carbazolequinones and carbazole alkaloids. Chemical and Pharmaceutical Bulletin 41, 2096-21 00. 

Ito, C., Itoigawa, M., Nakao, K., Murata, T., Tsuboi, M., Kaneda, N. and Furukawa, H. (2006) Induction of apoptosis by carbazole alkaloids isolated from Murraya koenigii. Phytomedicine 1 3, 359-365. 

Mukherjee, M., Mukherjee, S., Shaw, A.K. and Ganguly, S.N. (1983) Mukonicine, a carbazole alkaloid from leaves of Murraya koenigii. Phytochemistry 22, 2328-2329. 

Nutan, M.T.H., Hasan, C.M. and Rashid, M.A. (1999) Bismurrayafoline E a new dimeric carbazole alkaloid from Murraya koenigii. Fitoterapia 70(2), 130-133. 

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