Abstract
Carbazole alkaloids characterized by a heterocyclic aromatic basic skeleton are known from different organisms but do not represent a biogenetically homogenous group. The majority, comprising more than 330 derivatives, is derived from 3-methylcarbazole as common precursor and is designated as phytocarbazoles. They are nearly exclusively known from the four closely related plant genera Bergera (part of Murraya s. l.), Clausena, Glycosmis, and Micromelum of the family Rutaceae. Derived from anthranilic acid and malonyl-CoA the tricyclic basic skeleton is formed via a prenylated 2-quinolone intermediate. The following steps are speculated to involve the formation of 2-prenylindole and cyclization of the prenyl side chain to generate 3-methylcarbazole. Apart from different oxygenations and oxidations of the basic skeleton additional prenylations and geranylations contribute to the great structural diversity of phytocarbazoles which are grouped together according to their C13-, C18-, and C23-basic structures. Of taxonomic significance are the different oxidations of the characteristic C-3 methyl group leading to 3-formyl- and 3-carboxyl derivatives particularly accumulated in Clausena and Micromelum species. Predominant prenylation at C-5 is typical for Glycosmis and Micromelum, whereas in Clausena prenylation at different positions can contribute to an infrageneric grouping. Geranylation represents a characteristic biogenetic trend of Bergera. A wide variety of biological activities ranges from significant antimicrobial, antiprotozoal, and insecticidal properties to anti-inflammatory, antioxidative, antiplatelet aggregative, and anti-HIV activities. Of particular interest is the cytotoxicity of phytocarbazoles against various cancer cell lines, where some derivatives turned out to act as cell cycle inhibitors and apoptosis inducers. Especially the C23 derivative mahanine induced different cell-signaling pathways suggesting that it represents a multi-targeted and multi-functional compound that works on an array of different cancer types and has the potential to inhibit tumor growth in vivo.
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References
Adebajo AC, Ayoola OF, Iwalewa EO, Akindahunsi AA, Omisore NOA, Adewunmi CO, Adenowo TK (2006) Anti-trichomonal, biochemical and toxicological activities of methanolic extract and some carbazole alkaloids isolated from the leaves of Murraya koenigii growing in Nigeria. Phytomedicine 13:246–254
Adebajo AC, Iwalewa EO, Obuotor EM, Ibikunle GF, Omisore NO, Adewunmi CO, Obaparusi OO, Klaes M, Adetogun GE, Schmidt TJ, Verspohl EJ (2009) Pharmacological properties of the extract and some isolated compounds of Clausena lansium stem bark: anti-trichomonal, antidiabetic, anti-inflammatory, hepatoprotective and antioxidant effects. J Ethnopharmacol 122:10–19
Auranwiwat C, Laphookhieo S, Trisuwan K, Pyne SG, Ritthiwigrom T (2014) Carbazole alkaloids and coumarins from the roots of Clausena guillauminii. Phytochem Lett 9:113–116
Bacher M (1999) Strukturaufklärung von Sekundärmetaboliten aus tropischen Rutaceen und Meliaceen. Ph.D. thesis, University of Vienna (herein the NMR data of the newly described derivatives 117, 118, 178, 179, 181, 237)
Bayer RJ, Mabberley DJ, Morton C, Miller CH, Sharma IK, Pfeil BE, Rich S, Hitchcock R, Sykes S (2009) A molecular phylogeny of the orange subfamily (Rutaceae: Aurantioideae) using nine cpDNA sequences. Am J Bot 96:668–685
Bhattacharya K, Samanta SK, Tripathi R, Mallick A, Chandra S, Pal BC, Shaha C, Mandal C (2010) Apoptotic effects of mahanine on human leukemic cells are mediated through crosstalk between Apo-1/Fas signaling and Bid protein and via mitochondrial pathways. Biochem Pharmacol 79:361–372
Bhattacharya K, Bag AK, Tripathi R, Samanta SK, Pal BC, Shaha C, Chi Mandal (2014) Mahanine, a novel mitochondrial complex-III inhibitor induces GO/G1 arrest through redox alteration-mediated DNA damage response and regresses glioblastoma multiforme. Am J Cancer Res 4:629–647
Bhattacharya K, Maiti S, Mandal C (2016) PTEN negatively regulated mTORC2 formation and signaling in grade IVglioma via Rictor hyperphosphorylation at Thr1135 and direct the mode of action of an mTORC1/2 inhibitor. Oncogenesis 5:e227 (1–14)
Bhattacharyya P, Chakraborty A (1984) Mukonal, a probable biogenetic intermediate of pyranocarbazole alkaloids from Murraya koenigii. Phytochemistry 23:471–472
Bhattacharyya P, Chakraborty DP (1987) Carbazole alkaloids. In: Herz W, Grisebach H, Kirby GW, Tamm C (eds) Progress in the chemistry of organic natural products, vol 52. Springer, Wien, New York
Bhattacharyya P, Chowdhury BK (1984) Clausenapin: a new carbazole alkaloid from Clausena heptaphylla Wt. & Arn. Chem Ind 301
Bhattacharyya P, Chowdhury BK (1985a) Glycozolidal, a new carbazol alkaloid from Glycosmis pentaphylla. J Nat Prod 48:465–466
Bhattacharyya P, Chowdhury BK (1985b) 2-Methoxy-3-methylcarbazole from Murraya koenigii. Indian J Chem 24B:452
Bhattacharyya L, Roy SK, Chakraborty DP (1982) Structure of the carbazole alkaloid isomurrayazoline from Murraya koenigii. Phytochemistry 21:2432–2433
Bhattacharyya P, Chakraborty A, Chowdhury BK (1984) Heptazolicine, a carbazole alkaloid from Clausena heptaphylla. Phytochemistry 23:2409–2410
Bhattacharyya P, Chakrabarty PK, Chowdhury BK (1985) Glycozolidol, an antibacterial carbazole alkaloid from Glycosmis pentaphylla. Phytochemistry 24:882–883
Bhattacharyya P, Jash SS, Chowdhury BK (1986) A biogenetically important carbazole alkaloid from Murraya koenigii Spreng. Chem Ind 246
Bhattacharyya L, Chatterjee SK, Roy S, Chakraborty DP (1989) Murrayazolinol—a minor carbazole alkaloid from Murraya koenigii Spreng. J Indian Chem Soc 66:140–141
Bhattacharyya P, Biswas GK, Barua AK, Saha C, Roy IB, Chowdhury BK (1993) Clausenalene, a carbazole alkaloid from Clausena heptaphylla. Phytochemistry 33:248–250
Bhattacharyya P, Maiti AK, Basu K, Chowdhury BK (1994) Carbazole alkaloids from Murraya koenigii. Phytochemistry 35:1085–1086
Birari R, Roy SK, Singh A, Bhutani KK (2009) Pancreatic lipase inhibitory alkaloids of Murraya koenigii leaves. Nat Prod Commun 4:1089–1092
Birari R, Javia V, Bhutani KK (2010) Antiobesity and lipid lowering effects of Murraya koenigii (L.) Spreng leaves extracts and mahanimbine on high fat diet induced obese rats. Fitoterapia 81:1129–1133
Bordner J, Chakraborty DP, Chowdhury BK, Ganguli SN, Das KC, Weinstein B (1972) The crystal structure of murrayazoline (mahanimbidine, curryangin). Experientia 28:1406–1407
Börger C, Schmidt AW, Knölker HJ (2014) First total synthesis of chrestifoline-B and (±)-chrestifoline-C, and improved synthetic routes to bismurrayafoline-A, bismurrayafolinol and chrestifoline-D. Org Biomol Chem 12:3831–3835
Bowen IH, Perera KPWC (1982) Alkaloids, coumarins, and flavonoids of Micromelum ceylanicum. Phytochemistry 21:433–437
Bringmann G, Tasler S, Endress H, Peters K, Peters EM (1998a) Synthesis of mukonine and seven further 1-oxygenated carbazole alkaloids. Synthesis 1501–1505
Bringmann G, Ledermann A, Holenz J, Kao MT, Busse U, Wu HG, François G (1998b) Antiplasmodial activity of mono- and dimeric carbazoles. Planta Med 64:54–57
But PPH, Poon AWS, Shaw PC, Simmons MP, Greger H (2009) Contribution of molecular cladistics to the taxonomy of Rutaceae in China. J Syst Evol 47:144–150
Chaichantipyuth C, Pummangura S, Naowsaran K, Thanyavuthi D, Anderson JE, Mclaughlin JL (1988) Two new bioactive carbazole alkaloids from the root bark of Clausena harmandiana. J Nat Prod 51:1285–1288
Chakrabarty M, Nath AC, Khasnobis S, Chakrabarty M, Konda Y, Harigaya Y, Komiyama K (1997) Carbazole alkaloids from Murraya koenigii. Phytochemistry 46:751–755
Chakraborty DP (1966) Glycozoline, a carbazole derivative from Glycosmis pentaphylla (Retz.) DC. Tetrahedron Lett 7:661–664
Chakraborty DP (1969) Glycozoline, a carbazole derivative, from Glycosmis pentaphylla. Phytochemistry 8:769–772
Chakraborty DP (1977) Carbazole alkaloids. In: Herz W, Grisebach H, Kirby GW (eds) Fortschritte der Chemie organischer Naturstoffe, vol 34. Springer, Wien, New York
Chakraborty DP, Das BP (1966) Glycozolidine, a new carbazole derivative from Glycosmis pentaphylla. Sci Cult 32:181–182
Chakraborty DP, Roy S (1991) Carbazole alkaloids III. In: Herz W, Kirby GW, Steglich W, Tamm C (eds) Progress in the chemistry of organic natural products, vol 57. Springer, Wien, New York
Chakraborty DP, Barman BK, Bose PK (1964) On the structure of girinimbine, a pyranocarbazole derivative, isolated from Murraya koenigii Spreng. Sci Cult 30:445
Chakraborty DP, Barman BK, Bose PK (1965) On the constitution of murrayanine, a carbazole derivative isolated from Murraya koenigii Spreng. Tetrahedron 21:681–685
Chakraborty DP, Das KC, Bose PK (1966) Structure of mahanimbine, a pyranocarbazole derivative from Murraya koenigii Spreng. Sci Cult 32:83–84
Chakraborty DP, Das KC, Islam A (1970) Chemical taxonomy. XXIII. Heptazoline, a new carbazole alkaloid from Clausena heptaphylla Wt. and Arn. J Indian Chem Soc 47:1197–1198
Chakraborty DP, Das KC, Chowdhury BK (1971) Structure of murrayacine. J Org Chem 36:725–727
Chakraborty DP, Ganguly SN, Maji PN, Mitra AR, Das KC, Weinstein B (1973) Murrayazolinine, a carbazole alkaloid from Murraya koenigii Spreng. Chem Ind 322–323
Chakraborty DP, Bhattacharyya P, Islam A, Roy S (1974a) Chemical taxonomy. XXXV. Structure of murrayacinine, a new carbazole alkaloid from Murraya koenigii Spreng. Chem Ind 165
Chakraborty DP, Bhattacharyya P, Islam A, Roy S (1974b) Chemical taxonomy. XXXVI. Heptazolidine, a carbazole alkaloid from Clausena heptaphylla. Chem Ind 303
Chakraborty DP, Das KC, Das BP, Chowdhury BK (1975) On the antibiotic properties of some carbazole alkaloids. Trans Bose Res Inst 38:1–4
Chakraborty DP, Bhattacharyya P, Roy S, Bhattacharyya SP, Biswas AK (1978) Structure and synthesis of mukonine, a new carbazole alkaloid from Murraya koenigii. Phytochemistry 17:834–835
Chakraborty A, Saha C, Podder G, Chowdhury BK, Bhattacharyya P (1995a) Carbazole alkaloid with antimicrobial activity from Clausena heptaphylla. Phytochemistry 38:787–789
Chakraborty A, Chowdhury BK, Bhattacharyya P (1995b) Clausenol and clausenine—two carbazole alkaloids from Clausena anisata. Phytochemistry 40:295–298
Chakraborty M, Saha S, Mukhapadhyay S (2009) Murrayakoeninol—a new carbazole alkaloid from Murraya koenigii (Linn) Spreng. Nat Prod Commun 4:355–358
Chakravarty AK, Sarkar T, Masuda K, Shiojima K (1999) Carbazole alkaloids from roots of Glycosmis arborea. Phytochemistry 50:1263–1266
Chakravarty AK, Sarkar T, Masuda K, Takey T, Doi H, Kotani E, Shiojima K (2001) Structure and synthesis of glycoborine, a new carbazole alkaloid from the roots of Glycosmis arborea: a note on the structure of glycozolicine. Indian J Chem 40:484–489
Chakthong S, Bindulem N, Raknai S, Yodwaree S, Kaewsanee S, Kanjana-Opas A (2016) Carbazole-pyranocoumarin conjugate and two carbazole alkaloids from the stems of Clausena excavata. Nat Prod Res 30:1690–1697
Chen Y, Tang C, Wu Y, Mo SS, Wang S, Yang GZ, Mei ZN (2015) Glycosmisines A and B: isolation of two new carbazole-indole-type dimeric alkaloids from Glycosmis pentaphylla and an evaluation of their antiproliferative activities. Org Biomol Chem 13:6773–6781
Choi TA, Czerwonka R, Fröhner W, Krahl MP, Reddy KR, Franzblau SG, Knölker HJ (2006) Synthesis and activity of carbazole derivatives against Mycobacterium tuberculosis. Chem Med Chem 1:812–815
Choi TA, Czerwonka R, Forke R, Jäger A, Knöll J, Krahl MP, Krause T, Reddy KR, Franzblau SG, Knölker HJ (2008) Transition metals in organic synthesis—part 83: synthesis and pharmacological potential of carbazoles. Med Chem Res 17:374–385
Choi H, Gwak J, Cho M, Ryu MJ, Lee JH, Kim SK, Kim YH, Lee GW, Yun MY, Cuong NM, Shin JG, Song GY, Oh S (2010) Murrayafoline A attenuates the Wnt/β-catenin pathway by promoting the degradation of intracellular β-catenin proteins. Biochem Biophys Res Commun 391:915–920
Choudhury BK, Chakraborty DP (1971) Mukoeic acid, the first carbazole carboxylic acid from a plant source. Phytochemistry 10:1967–1970
Chowdhury BK, Mustapha A, Garba M, Bhattacharyya P (1987) Carbazole and 3-methylcarbazole from Glycosmis pentaphylla. Phytochemistry 26:2138–2139
Chowdhury BK, Jha S, Bhattacharyya P, Mukherjee M (2001) Two new carbazole alkaloids from Murraya koenigii. Indian J Chem 40B:490–494
Cui CB, Yan SY, Cai B, Yao XS (2002) Carbazole alkaloids as new cell cycle inhibitor and apoptosis inducers from Clausena dunniana Levl. J Asian Nat Prod Res 4:233–241
Cuong NM, Hung TQ, Sung TV, Taylor WC (2004) A new carbazole alkaloid from Glycosmis stenocarpa roots. Chem Pharm Bull 52:1175–1178
Cuong NM, Wilhelm H, Porzel A, Arnold N, Wessjohann L (2008) 1-O-Substituted derivatives of murrayafoline A and their antifungal properties. Nat Prod Res 22:1428–1432
Dai J, Ma D, Fu C, Ma S (2015) Gram scale total synthesis of 2-hydroxy-3-methylcarbazole, pyrano[3,2-a]carbazole and prenylcarbazole alkaloids. Eur J Org Chem 5655–5662
Das KC, Chakraborty DP, Bose PK (1965) Antifungal activity of some constituents of Murraya koenigii Spreng. Experientia 21:340
Das R, Bhattacharya K, Samanta SK, Pal BC, Mandal Chi (2014) Improved chemosensitivity in cervical cancer to cisplatin: synergistic activity of mahanine through STAT3 inhibition. Cancer Lett 351:81–90
Deng HD, Mei WL, Wang H, Guo ZK, Dong WH, Wang H, Li SP, Dai HF (2014) Carbazole alkaloids from the peels of Clausena lansium. J Asian Nat Prod Res 16:1024–1028
Du YQ, Liu H, Li CJ, Ma J, Zhang D, Li L, Sun H, Bao XQ, Zhang DM (2015) Bioactive carbazole alkaloids from the stems of Clausena lansium. Fitoterapia 103:122–128
Fiebig M, Pezzuto JM, Soejarto DD, Kinghorn AD (1985) Koenoline, a further cytotoxic carbazole alkaloid from Murraya koenigii. Phytochemistry 24:3041–3043
Furukawa H, Wu TS, Ohta T (1983) Bismurrayafoline-A and -B, two novel “dimeric” carbazole alkaloids from Murraya euchrestifolia. Chem Pharm Bull 31:4202–4205
Furukawa H, Yogo M, Ito C, Wu TS, Kuoh CS (1985a) New carbazolequinones having dimethylpyran ring system, from Murraya euchrestifolia. Chem Pharm Bull 33:1320–1322
Furukawa H, Wu TS, Kuoh CS (1985b) Structures of murrafoline-B and -C, new binary carbazole alkaloids from Murraya euchrestifolia. Chem Pharm Bull 33:2611–2613
Furukawa H, Wu TS, Ohta T, Kuoh CS (1985c) Chemical constituents of Murraya euchrestifolia Hayata. Structures of novel carbazolequinones and other new carbazole alkaloids. Chem Pharm Bull 33:4132–4138
Furukawa H, Wu TS, Kuoh CS (1985d) Dihydroxygirinimbine, a new carbazole alkaloid from Murraya euchrestifolia. Heterocycles 23:1391–1393
Furukawa H, Ito C, Yogo M, Wu TS (1986) Structures of murrayastine, murrayaline, and pyrayafoline; three new carbazole alkaloids from Murraya euchrestifolia. Chem Pharm Bull 34:2672–2675
Furukawa H, Ito C, Wu TS, McPhail AT (1993) Structure elucidation of murrafolines, six novel binary alkaloids isolated from Murraya euchrestifolia. Chem Pharm Bull 41:1249–1254
Ganguly SN, Sarkar A (1978) Exozoline, a new carbazole alkaloid from the leaves of Murraya exotica. Phytochemistry 17:1816–1817
Graebe C, Glaser C (1872) Ueber Carbazol. Chem Ber 5:12–15
Grassi P (1998) Vergleichende phytochemische Untersuchungen in der Gattung Micromelum (Rutaceae). Diploma-thesis, University of Vienna
Greger H, Hofer O, Kählig H, Wurz G (1992) Sulfur containing cinnamides with antifungal activity from Glycosmis cyanocarpa. Tetrahedron 48:1209–1218
Greger H, Zechner G, Hofer O, Vajrodaja S (1996) Bioactive amides from Glycosmis species. J Nat Prod 59:1163–1168
Han JH, Kim Y, Jung SH, Lee JJ, Park HS, Song GY, Cuong NM, Kim YH, Myung CS (2015) Murrayafoline A induces a G0/G1-phase arrest in platelet-derived growth factor-stimulated vascular smooth muscle cells. Korean J Physiol Pharmacol 19:421–426
Herdits-Riemer B (2002) Vergleichende phytochemische Untersuchungen in der Gattung Clausena (Rutaceae). Organspezifische und geographische Differenzierung. Ph.D. thesis, University of Vienna
Hesse R, Kataeva O, Schmidt AW, Knölker HJ (2014) Synthesis of prenyl- and geranyl-substituted carbazole alkaloids by DIBAL-H promoted reductive pyran ring opening of dialkylpyrano[3,2-a]carbazoles. Chem Eur J 20:9504–9509
Huang JY, Ma YZ, Yuan YH, Zuo W, Chu SF, Liu H, Du GH, Zhang DM, Chen NH (2016) Claulansine F promoted the neuronal differentiation of neural stem and progenitor cells through Akt/GSK-3ß/ß-catenin pathway. Eur J Pharmacol 786:72–84
Ito C, Furukawa H (1990) New carbazole alkaloids from Murraya euchrestifolia Hayata. Chem Pharm Bull 38:1548–1550
Ito C, Furukawa H (1991) Structure of murranimbine, a novel dimeric carbazole alkaloid from Murraya euchrestifolia. Chem Pharm Bull 39:1355–1357
Ito C, Wu TS, Furukawa H (1987) Three new carbazole alkaloids from Murraya euchrestifolia. Chem Pharm Bull 35:450–452
Ito C, Wu TS, Furukawa H (1988) New carbazole alkaloids from Murraya euchrestifolia. Chem Pharm Bull 36:2377–2380
Ito C, Wu TS, Furukawa H (1990) Novel binary carbazole alkaloids from Murraya euchrestifolia. Chem Pharm Bull 38:1143–1146
Ito C, Nakagawa M, Wu TS, Furukawa H (1991a) New carbazole alkaloids from Murraya euchrestifolia. Chem Pharm Bull 39:1668–1671
Ito C, Nakagawa M, Wu TS, Furukawa H (1991b) New carbazole alkaloids from Murraya euchrestifolia. Chem Pharm Bull 39:2525–2528
Ito C, Okahana N, Wu TS, Wang ML, Lai JS, Kuoh CS, Furukawa H (1992a) New carbazole alkaloids from Murraya euchrestifolia. Chem Pharm Bull 40:230–232
Ito C, Kanbara H, Wu TS, Furukawa H (1992b) Murrayamine-C from Murraya euchrestifolia. Phytochemistry 31:1083–1084
Ito C, Thoyama Y, Omura M, Kajiura I, Furukawa H (1993) Alkaloidal constituents of Murraya koenigii. Isolation and structural elucidation of novel binary carbazolequinones and carbazole alkaloids. Chem Pharm Bull 41:2096–2100
Ito C, Ohta H, Tan HTW, Furukawa H (1996) Constituents of Clausena excavata. Isolation and structural elucidation of seven new carbazole alkaloids and a new coumarin. Chem Pharm Bull 44:2231–2235
Ito C, Katsuno S, Ohta H, Omura M, Kajiura I, Furukawa H (1997) Constituents of Clausena excavata. Isolation and structural elucidation of new carbazole alkaloids. Chem Pharm Bull 45:48–52
Ito C, Katsuno S, Ruangrungsi N, Furukawa H (1998) Structures of clausamine-A, -B, -C, three novel carbazole alkaloids from Clausena anisata. Chem Pharm Bull 46:344–346
Ito C, Katsuno S, Itoigawa M, Ruangrungsi N, Mukainaka T, Okuda M, Kitagawa Y, Tokuda H, Nishino H, Furukawa H (2000) New carbazole alkaloids from Clausena anisata with antitumor promoting activity. J Nat Prod 63:125–128
Ito C, Itoigawa M, Sato A, Hasan CM, Rashid MA, Tokuda H, Mukainaka T, Nishino H, Furukawa H (2004) Chemical constituents of Glycosmis arborea: three new carbazole alkaloids and their biological activity. J Nat Prod 67:1488–1491
Ito C, Itoigawa M, Nakao K, Murata T, Tsuboi M, Kaneda N, Furukawa H (2006) Induction of apoptosis by carbazole alkaloids isolated from Murraya koenigii. Phytomedicine 13:359–365
Ito C, Itoigawa M, Aizawa K, Yoshida K, Ruangrungsi N, Furukawa H (2009) γ-Lactone carbazoles from Clausena anisata. J Nat Prod 72:1202–1204
Ito C, Itoigawa M, Nakao K, Murata T, Kaneda N, Furukawa H (2012) Apoptosis of HL-60 leukemia cells induced by carbazole alkaloids isolated from Murraya euchrestifolia. J Nat Med 66:357–361
Itoigawa M, Kashiwada Y, Ito C, Furukawa H, Tachibana Y, Bastow KF, Lee KH (2000) Antitumor agents 203. Carbazole alkaloid murrayaquinone A and related synthetic carbazolequinones as cytotoxic agents. J Nat Prod 63:893–897
Jagadeesh S, Sinha S, Pal BC, Battacharya S, Banerjee PP (2007) Mahanine reverses an epigenetically silenced tumor suppressor gene RASSF1A in human prostate cancer cells. Biochem Biophys Res Commun 362:212–217
Jagtap S, Khare P, Mangal P, Kondepudi KK, Bishnoi M, Bhutani KK (2016) Effect of mahanimbine, an alkaloid from curry leaves, on high-fat diet-induced adiposity, insulin resistance, and inflammatory alterations. BioFactors. doi:10.1002/biof.1333(1-12)
Jash SS, Biswas GK, Bhattacharyya SK, Bhattacharyya P, Chakraborty A, Chowdhury BK (1992) Carbazole alkaloids from Glycosmis pentaphylla. Phytochemistry 31:2503–2505
Jiang HY, Zhang WJ, You CX, Yang K, Fan L, Feng JB, Chen J, Yang YJ, Wang CF, Deng ZW, Yin HB, Du SS (2014) Two new cytotoxic constituents from the Clausena lansium (Lour.) Skeels. Phytochem Lett 9:92–95
Joshi BS, Gawad DH (1974) Isolation and structure of indizoline, a new carbazole alkaloid from Clausena indica. Indian J Chem 12:437–440
Joshi BS, Kamat VN, Saksena AK, Govindachari TR (1967) Structure of heptaphylline, a carbazole alkaloid from Clausena heptaphylla Wt. & Arn. Tetrahedron Lett 41:4019–4022
Joshi BS, Kamat VN, Gawad DH (1970) On the structures of girinimbine, mahanimbine, isomahanimbine, koenimbidine and murrayacine. Tetrahedron 26:1475–1482
Joshi BS, Kamat VN, Gawad DH, Govindachari TR (1972) Structure and synthesis of heptaphylline. Phytochemistry 11:2065–2071
Kamaruzzman RS, Chakraborty DP (1989) Mupamine from Glycosmis pentaphylla. Phytochemistry 28:677–678
Kedderis GL, Rickert DE, Pandey RN, Hollenberg PF (1986) 18 O-studies of the peroxidase-catalyzed oxidation of N-methylcarbazole. J Biol Chem 261:15910–15914
Khan D, Khan S, Badshah S, Ali H, Ullah H, Muhammad Z, Woodward S (2016) New furocarbazole alkaloids from Lonicera quinquelocularis. Nat Prod Res 30:74–78
Knölker HJ, Reddy KR (2002) Isolation and synthesis of biologically active carbazole alkaloids. Chem Rev 102:4303–4427
Knölker HJ, Reddy KR (2008) The chemistry and biology of carbazoles. In: Cordell GA (ed) The alkaloids, vol 65. Academic Press, Amsterdam
Ko FN, Lee YS, Wu TS, Teng CM (1994) Inhibition of cyclooxygenase activity and increase in platelet cyclic AMP by girinimbine isolated from Murraya euchrestifolia. Biochem Pharmacol 48:353–360
Kok YY, Mooi LY, Ahmed K, Sukari MA, Mat N, Rahmani M, Ali AM (2012) Anti-tumour promoting activity and antioxidant properties of girinimbine isolated from the stem bark of Murraya koenigii S. Molecules 17:4651–4660
Kong YC, Cheng KF, Ng KH, But PPH, Li Q, Yu SX, Chang HT, Cambie RC, Kinoshita T, Kan WS, Waterman PG (1986) A chemotaxonomic division of Murraya based on the distribution of the alkaloids yuehchukene and girinimbine. Biochem Syst Ecol 14:491–497
Kong YC, But PPH, Ng KH, Cheng KF, Chang KL, Wong KM, Gray AI, Waterman PG (1988a) The biochemical systematics of Merrillia; in relation to Murraya, the Clauseneae and the Aurantioideae. Biochem Syst Ecol 16:47–50
Kong YC, But PPH, Ng KH, Li Q, Cheng KF, Waterman PG (1988b) Micromelum: a key genus in the chemosystematics of the Clauseneae. Biochem Syst Ecol 16:485–489
Kongkathip B, Kongkathip N, Sunthitikawinsakul A, Napaswat C, Yoosook C (2005) Anti-HIV-1 constituents from Clausena excavata: Part II. Carbazoles and a pyranocoumarin. Phytother Res 19:728–731
Kumar V, Reisch J, Wickramasinghe A (1989) Glycomaurin and glycomaurrol, new carbazole alkaloids from Glycosmis mauritiana (Rutaceae) bark. Aust J Chem 42:1375–1379
Kumar V, Vallipuram K, Adebajo AC, Reisch J (1995) 2,7-Dihydro-3-formyl-1-(3′-methyl-2′-butenyl)carbazole from Clausena lansium. Phytochemistry 40:1563–1565
Kureel SP, Kapil RS, Popli SP (1969a) Terpenoid alkaloids from Murraya koenigii Spreng. II. The constitution of cyclomahanimbine, bicyclomahanimbine, and mahanimbidine. Tetrahedron Lett 3857–3862
Kureel SP, Kapil RS, Popli SP (1969b) New alkaloids from Murraya koenigii Spreng. Experientia 25:790–791
Kureel SP, Kapil RS, Popli SP (1970a) Terpenoid alkaloids from Murraya koenigii Spreng. IV. Structure and synthesis of mahanimbinine. Experientia 26:1055
Kureel SP, Kapil RS, Popli SP (1970b) Two novel alkaloids from Murraya koenigii Spreng: mahanimbicine and bicyclomahanimbicine. Chem Ind 29:958
Lamberton JA, Price JR, Redcliffe AH (1967) Micromelin, a new coumarin from Micromelum minutum (Forst. f.) Seem (family Rutaceae). Aust J Chem 20:973–979
Lebold TP, Kerr MA (2007) Total synthesis of eustifolines A–D and glycomaurrol via a divergent Diels–Alder strategy. Org Lett 9:1883–1886
Lee V, Cheung MK, Wong WT, Cheng KF (1996) Studies on the acid-catalyzed dimerization of 2-prenylindoles. Tetrahedron 52:9455–9468
Li WS, McChesney JD, El-Feraly FS (1991) Carbazole alkaloids from Clausena lansium. Phytochemistry 30:343–346
Liger F, Popowycz F, Besson T, Picot L, Galmarini CM, Joseph B (2007) Synthesis and antiproliferative activity of clausine E, mukonine, and koenoline bioisosteres. Bioorg Med Chem 15:5615–5619
Lin W, Wang Y, Lin S, Li CX, Zhou C, Wang SG, Huang H, Liu PQ, Ye G, Shen XY (2012) Induction of cell cycle arrest by the carbazole alkaloid clauszoline-I from Clausena vestita D. D. Tao via inhibition of the PKCδ phosphorylation. Eur J Med Chem 47:214–220
Liu H, Li CJ, Yang JZ, Ning N, Si YK, Li L, Chen NH, Zhao Q, Zhang DM (2012) Carbazole alkaloids from the stems of Clausena lansium. J Nat Prod 75:677–682
Lontsi D, Ayafor JF, Sondengam BL, Connolly JD, Rycroft DS (1985) Ekeberginine, a new carbazole alkaloid from Ekebergia senegalensis (Meliaceae). Tetrahedron Lett 26:4249–4252
Lukaseder B (2000) Vergleichende HPLC-Analysen in der Gattung Glycosmis (Rutaceae). Isolierung und Identifizierung charakteristischer Inhaltsstoffe. Diploma-thesis, University of Vienna
Lukaseder B, Vajrodaya S, Hehenberger T, Seger C, Nagl M, Lutz-Kutschera G, Robien W, Greger H, Hofer O (2009) Prenylated flavanones and flavanonols as chemical markers in Glycosmis species (Rutaceae). Phytochemistry 70:1030–1037
Lv HN, Wen R, Zhou Y, Zeng KW, Li J, Guo XY, Tu PF, Jiang Y (2015) Nitrogen oxide inhibitory trimeric and dimeric carbazole alkaloids from Murraya tetramera. J Nat Prod 78:2432–2439
Ma CY, Case RJ, Wang YH, Zhang HJ, Tan GT, Hung NV, Cuong NM, Franzblau SG, Soejarto DD, Fong HHS, Pauli GF (2005) Anti-tuberculosis constituents from the stem bark of Micromelum hirsutum. Planta Med 71:261–267
Ma YZ, Ning N, He WB, Li JW, Hu JF, Chu SF, Chen NH (2013) Claulansine F promotes neuritogenesis in PC12 cells via the ERK signaling pathway. Acta Pharmacol Sin 34:1499–1507
Maneerat W, Laphookhieo S (2010) Antitumor alkaloids from Clausena lansium. Heterocycles 81:1261–1269
Maneerat W, Ritthiwigrom T, Cheenpracha S, Prawat U, Laphookhieo S (2011) Clausenawallines A and B, two new dimeric carbazole alkaloids from the roots of Clausena wallichii. Tetrahedron Lett 52:3303–3305
Maneerat W, Ritthiwigrom T, Cheenpracha S, Laphookhieo S (2012a) Carbazole alkaloids and coumarins from Clausena lansium roots. Phytochem Lett 5:26–28
Maneerat W, Ritthiwigrom T, Cheenpracha S, Promgool T, Yossathera K, Deachathai S, Phakhodee W, Laphookhieo S (2012b) Bioactive carbazole alkaloids from Clausena wallichii roots. J Nat Prod 75:741–746
Manimekalai R, Salomi MV, Shoba G (2015) Insiliko docking analysis of carbazole alkaloids from Murraya koenigii against PP2A. Int J Pharm Bio Sci 6(B):913–928
Markad SB, Argade NP (2016) Biomimetic collective total synthesis of bioactive carbazole alkaloids indizoline, mafaicheenamine A, claulamine A, claulansine A, and the proposed claulamine E. J Org Chem 81:5222–5227
McPhail AT, Wu TS, Ohta T, Furukawa H (1983) Structure of ±murrafoline, a novel biscarbazole alkaloid from Murraya euchrestifolia. Tetrahedron Lett 24:5377–5380
Meragelman KM, McKee TC, Boyd MR (2000) Siamenol, a new carbazole alkaloid from Murraya siamensis. J Nat Prod 63:427–428
Mester I, Reisch J (1977) Constituents of Clausena anisata (Willd.) Oliv. (Rutaceae), II. Isolation and structure of mupamine, a new carbazole alkaloid. Liebigs Ann Chem 1725–1729
Mou FJ, Zhang DX (2009) Pollen morphology supports the reinstatement of Bergera (Rutaceae). Nord J Bot 27:298–304
Mukherjee M, Mukherjee S, Shaw AK, Ganguly SN (1983a) Mukonicine, a carbazole alkaloid from leaves of Murraya koenigii. Phytochemistry 22:2328–2329
Mukherjee S, Mukherjee M, Ganguly SN (1983b) Glycozolinine, a carbazole derivative from Glycosmis pentaphylla. Phytochemistry 22:1064–1065
Nagappan T, Ramasamy P, Abdul Wahid ME, Chandra Segaran T, Vairappan CS (2011) Biological activity of carbazole alkaloids and essential oil of Murraya koenigii against antibiotic resistant microbes and cancer cell lines. Molecules 16:9651–9664
Nagappan T, Chandra Segaran T, Abdul Wahid ME, Ramasamy P, Vairappan CS (2012) Efficacy of carbazole alkaloids, essential oil and extract of Murraya koenigii in enhancing subcutaneous wound healing in rats. Molecules 17:14449–14463
Nakahara K, Trakoontivakorn G, Alzoreky NS, Ono H, Onishi-Kameyama M, Yoshida M (2002) Antimutagenicity of some edible Thai plants, and a bioactive carbazole alkaloid, mahanine, isolated from Micromelum minutum. J Agric Food Chem 50:4796–4802
Nakamura S, Nakashima S, Oda Y, Yokota N, Fujimoto K, Matsumoto T, Ohta T, Ogawa K, Maeda S, Nishida S, Matsuda H, Yoshikawa M (2013) Alkaloids from Sri Lankan curry-leaf (Murraya koenigii) display melanogenesis inhibitory activity: Structures of karapinchamines A and B. Bioorg Med Chem 21:1043–1049
Nakatani N, Tachibana Y, Kikuzaki H (2001) Establishment of a model substrate oil for antioxidant activity assessment by oil stability index method. J Am Oil Chem Soc 78:19–23
Nalli Y, Khajuria V, Gupta S, Arora P, Riyaz-Ul-Hassan S, Ahmed Z, Ali A (2016) Four new carbazole alkaloids from Murraya koenigii that display anti-inflammatory and anti-microbial activities. Org Biomol Chem 14:3322–3332
Narasimhan NS, Paradkar MV, Chitguppi VP (1968) Structures of mahanimbin and koenimbin. Tetrahedron Lett 5501–5504
Narasimhan NS, Paradkar MV, Kelkar SL (1970) Alkaloids of Murraya koenigii: Structures of mahanine, koenine, koenigine, and koenidine. Indian J Chem 8:473–474
Ngadjui BT, Ayafor JF, Sondengam BL, Connolly JD (1989) Quinolone and carbazole alkaloids from Clausena anisata. Phytochemistry 28:1517–1519
Nutan MTH, Hasnat A, Rashid MA (1998) Antibacterial and cytotoxic activities of Murraya koenigii. Fitoterapia 69:173–175
Nutan MTH, Hasan CM, Rashid MA (1999) Bismurrayafoline E: a new dimeric carbazole alkaloid from Murraya koenigii. Fitoterapia 70:130–133
Okorie DA (1975) A new carbazole alkaloid and coumarins from roots of Clausena anisata. Phytochemistry 14:2720–2721
Pacher T (2005) Phytochemical analyses within the two tropical plant genera Glycosmis (Rutaceae) and Stemona (Stemonaceae) in special consideration of the formation of phytoalexins and artifacts. Ph.D. thesis, University of Vienna
Pacher T, Bacher M, Hofer O, Greger H (2001) Stress induced carbazole phytoalexins in Glycosmis species. Phytochemistry 58:129–135
Pandey J, Maurya R, Raykhera R, Srivastava MN, Yadav PP, Tamrakar AK (2014) Murraya koenigii (L.) Spreng. ameliorates insulin resistance in dexamethasone-treated mice by enhancing peripheral insulin sensitivity. J Sci Food Agric 94:2282–2288
Patel OPS, Mishra A, Maurya R, Saini D, Pandey J, Taneja I, Raju KSR, Kanojiya S, Shukla SK, Srivastava MN, Wahajuddin M, Tamrakar AK, Srivastava AK, Yadav PP (2016) Naturally occurring carbazole alkaloids from Murraya koenigii as potential antidiabetic agents. J Nat Prod 79:1276–1284
Pemmer J (2002) Charakteristische Stoffausstattungen von Bergera (Rutaceae) und ihre antifungalen Aktivitäten. Diploma-thesis, University of Vienna
Peng WW, Zeng GZ, Song WW, Tan NH (2013) A new cytotoxic carbazole alkaloid and two new other alkaloids from Clausena excavata. Chem Biodivers 10:1317–1321
Pieroni M, Girmay S, Sun D, Sahu R, Tekwani BL, Tan GT (2012) Synthesis and structure-activity relationships of lansine analogues as antileishmanial agents. Chem Med Chem 7:1895–1900
Potterat O, Puder C, Bolek W, Wagner K, Ke C, Ye Y, Gillardon F (2005) Clausine Z, a new carbazole alkaloid from Clausena excavata with inhibitory activity on CDK5. Pharmazie 60:637–639
Prakash D, Raj K, Kapil RS, Popli SP (1980) Chemical constituents of Clausena lansium: part I. Structure of lansamide I and lansine. Indian J Cem 19B:1075–1076
Qiu Y, Ma D, Fu CL, Ma SM (2013) An efficient Au-catalyzed synthesis of isomukonidine, clausine L, mukondine, glycosinine, mukonal, and clausine V from propadienyl methyl ether. Org Biomol Chem 11:1666–1671
Rahman MM, Gray AI (2005) A benzoisofuranone derivative and carbazole alkaloids from Murraya koenigii and their antimicrobial activity. Phytochemistry 66:1601–1606
Rahmani M, Ling CY, Sukari MA, Ismail HBM, Meon S, Aimi N (1998) 7-Methoxyglycomaurin: A new carbazole alkaloid from Glycosmis rupestris. Planta Med 64:780
Rama Rao AV, Bhide KS, Mujumdar RB (1980) Mahanimbinol. Chem Ind 697–698
Ramsewak RS, Nair MG, Strasburg GM, DeWitt DL, Nitiss JL (1999) Biologically active carbazole alkaloids from Murraya koenigii. J Agric Food Chem 47:444–447
Reisch J, Goj O, Wickramasinghe A, Herath HMTB, Henkel G (1992) Carbazole alkaloids from seeds of Murraya koenigii. Phytochemistry 31:2877–2879
Reisch J, Adebajo AC, Aladesanmi AJ, Adesina KS, Bergenthal D, Meve U (1994) Chemotypes of Murraya koenigii growing in Sri Lanka. Planta Med 60:295–296
Riemer B, Hofer O, Greger H (1997) Tryptamine derived amides from Clausena indica. Phytochemistry 45:337–341
Rodanant P, Surarit R, Lapookhieo S, Kuvatanasuchati J (2015) In vitro evaluation of the antibacterial and anti-inflammation activities of Clausena lansium. Songklanakarin J Sci Technol 37:43–48
Roy S, Bhattacharyya P, Chakraborty DP (1974) 3-Methylcarbazole from Clausena heptaphylla. Phytochemistry 13:1017
Roy S, Guha R, Ghosh S, Chakraborty DP (1982a) Biomimetic hydroxylation studies on carbazole alkaloids. Indian J Chem 21B:617–618
Roy S, Bhattacharyya L, Chakraborty DP (1982b) Structure and synthesis of mukoline and mukolidine, two new carbazole alkaloids from Murraya koenigii Spreng. J Ind Chem Soc 59:1369–1371
Roy MK, Thalang VN, Trakoontivakorn G, Nakahara K (2004) Mechanism of mahanine-induced apoptosis in human leukemia cells (HL-60). Biochem Pharmacol 67:41–51
Roy MK, Thalang VN, Trakoontivakorn G, Nakahara K (2005) Mahanine, a carbazole alkaloid from Micromelum minutum, inhibits cell growth and induces apoptosis in U937 cells through a mitochondrial dependent pathway. Br J Pharmacol 145:145–155
Ruangrungsi N, Ariyaprayoon J, Lange GL, Organ MG (1990) Three new carbazole alkaloids isolated from Murraya siamensis. J Nat Prod 53:946–952
Saha C, Chowdhury BK (1998) Carbazoloquinones from Murraya koenigii. Phytochemistry 48:363–366
Samanta SK, Dutta D, Roy S, Bhattacharya K, Sarkar S, Dasgupta AK, Pal BC, Chhab Mandal, Chit Mandal (2013) Mahanine, a DNA minor groove binding agent exerts cellular cytotoxicity with involvement of C-7-OH and –NH functional group. J Med Chem 56:5709–5721
Samuel R, Ehrendorfer F, Chase MW, Greger H (2001) Phylogenetic analyses of Aurantioideae (Rutaceae) based on non-coding plastid DNA sequences and phytochemical features. Plant Biol 3:77–87
Sarkar S, Dutta D, Samanta SK, Bhattacharya K, Pal BC, Li JP, Datta K, Chhab Mandal, Chit Mandal (2013) Oxidative inhibition of Hsp90 disrupts the super-chaperone complex and attenuates pancreatic adenocarcinoma in vitro and in vivo. Int J Cancer 132:695–706
Schmidt AW, Reddy KR, Knölker HJ (2012) Occurrence, biogenesis, and synthesis of biologically active carbazole alkaloids. Chem Rev 112:3193–3328
Shaikh MS, Karpoormath R, Thapliyal N, Rane RA, Palkar MB, Faya AM, Patel HM, Alwan WS, Jain K, Hampannavar GA (2015) Current perspective of natural alkaloid carbazole and its derivatives as antitumor agents. Anticancer Agents Med Chem 15:1049–1065
Shen DY, Chao CH, Chan HH, Huang GJ, Hwang TL, Lai CY, Lee KH, Thang TD, Wu TS (2012) Bioactive constituents of Clausena lansium and a method for discrimination of aldose enantiomers. Phytochemistry 82:110–117
Shen DY, Chan YY, Hwang TL, Juang SH, Huang SC, Kuo PC, Thang TD, Lee EJ, Damu AG, Wu TS (2014) Constituents of the roots of Clausena lansium and their potential anti-inflammatory activity. J Nat Prod 77:1215–1223
Shen DY, Kuo PC, Huang SC, Hwang TL, Chan YY, Shieh PC, Ngan NT, Thang TD, Wu TS (2017) Constituents from the leaves of Clausena lansium and their anti-inflammatory activity. J Nat Med 71:96–104
Shi XJ, Ye G, Tang WJ, Zhao WM (2010) A new coumarin and carbazole alkaloid from Clausena vestita D. D. Tao. Helv Chim Acta 93:985–990
Shivakumar VS, Appelhans MS, Johnson G, Carlsen M, Zimmer EA (2016) Analysis of whole chloroplast genomes from the genera of the Clauseneae, the curry tribe (Rutaceae, Citrus family). Mol Phylogenet Evol 10:10. doi:10.1016/j.ympev.2016.12.015
Sim KM, Teh HM (2011) A new carbazole alkaloid from the leaves of Malayan Murraya koenigii. J Asian Nat Prod Res 13:972–975
Sinha S, Pal BC, Jagadeesh S, Banerjee PP, Bandyopadhaya A, Bhattacharya S (2006) Mahanine inhibits growth and induces apoptosis in prostate cancer cells through the deactivation of Akt and activation of caspases. Prostate 66:1257–1265
Songsiang U, Thongthoom T, Boonyarat C, Yenjai C (2011) Claurailas A–D, cytotoxic carbazole alkaloids from the roots of Clausena harmandiana. J Nat Prod 74:208–212
Songue JL, Kouam Dongo E, Mpondo TN, White RL (2012) Chemical constituents from stem bark and roots of Clausena anisata. Molecules 17:13673–13686
Sriphana U, Thongsri Y, Prariyachatigul C, Pakawatchai C, Yenjai C (2013) Clauraila E from the roots of Clausena harmandiana and antifungal activity against Pythium insidiosum. Arch Pharm Res 36:1078–1083
Sripisut T, Laphookhieo S (2010) Carbazole alkaloids from the stems of Clausena excavata. J Asian Nat Prod Res 12:614–617
Sripisut T, Cheenpracha S, Ritthiwigrom T, Prawat U, Laphookhieo S (2012) Chemical constituents from the roots of Clausena excavata and their cytotoxicity. Rec Nat Prod 6:386–389
Sunthitikawinsakul A, Kongkathip N, Kongkathip B, Phonnakhu S, Daly JW, Spande TF, Nimit Y, Rochanaruangrai S (2003) Coumarins and carbazoles from Clausena excavata exhibited antimycobacterial and antifungal activities. Planta Med 69:155–157
Syam S, Abdul AB, Sukari MA, Mohan S, Abdelwahab SI, Wah TS (2011) The growth suppressing effects of girinimbine on Hepg2 involve induction of apoptosis and cell cycle arrest. Molecules 16:7155–7170
Tachibana Y, Kikuzaki H, Lajis NH, Nakatani N (2001) Antioxidative activity of carbazoles from Murraya koenigii leaves. J Agric Food Chem 49:5589–5594
Tachibana Y, Kikuzaki H, Lajis NH, Nakatani N (2003) Comparison of antioxidative properties of carbazole alkaloids from Murraya koenigii leaves. J Agric Food Chem 51:6461–6467
Tan SP, Ali AM, Nafiah MA, Awang K, Ahmad K (2015) Isolation and cytotoxic investigation of new carbazole alkaloids from Murraya koenigii (Linn.) Spreng. Tetrahedron 71:3946–3953
Tatsimo SJN, Tamokou JDD, Lamshöft M, Mouafo FT, Lannang AM, Sarkar P, Bag PK, Spiteller M (2015) LC-MS guided isolation of antibacterial and cytotoxic constituents from Clausena anisata. Med Chem Res 24:1468–1479
Taufiq-Yap YH, Peh TH, Ee GCL, Rahmani M, Sukari MA, Ali AM, Muse R (2007) A new cytotoxic carbazole alkaloid from Clausena excavata. Nat Prod Res 21:810–813
Thongthoom T, Songsiang U, Phaosiri C, Yenjai C (2010) Biological activity of chemical constituents from Clausena harmandiana. Arch Pharm Res 33:675–680
Utaipan T, Athipornchai A, Suksamrarn A, Jirachotikoon C, Yuan X, Lertcanawanichakul M, Chunglok W (2017) Carbazole alkaloids from Murraya koenigii trigger apoptosis and autophagic flux inhibition in human oral squamous cell carcinoma cells. J Nat Med 71:158–169
Uvarani C, Sankaran M, Jaivel N, Chandraprakash K, Ata A, Mohan PS (2013) Bioactive dimeric carbazole alkaloids from Murraya koenigii. J Nat Prod 76:993–1000
Uvarani C, Jaivel N, Sankaran M, Chandraprakash K, Ata A, Mohan PS (2014) Axially chiral biscarbazoles and biological evaluation of the constituents from Murraya koenigii. Fitoterapia 94:10–20
Vajrodaya S (1998) Comparative phytochemical analyses within the genus Glycosmis (Rutaceae-Citroideae). Ph.D. thesis, University of Vienna
Vajrodaya S, Bacher M, Greger H, Hofer O (1998) Organ-specific chemical differences in Glycosmis trichanthera. Phytochemistry 48:897–902
Wang YS, He HP, Shen YM, Hong X, Hao XJ (2003) Two new carbazole alkaloids from Murraya koenigii. J Nat Prod 66:416–418
Wang JS, Zheng YT, Efferth T, Wang RR, Shen YM, Hao XJ (2005) Indole and carbazole alkaloids from Glycosmis montana with weak anti-HIV and cytotoxic activities. Phytochemistry 66:697–701
Wang SL, Cai B, Cui CB, Yan SY, Wu CF (2008) Study on induction of apoptosis by girinimbine in HCT-15 cell in vitro. Chin J Pharm Anal 28:176–181
Whiting DA, Begley MJ, Clarke DG, Crombie L (1970) X-ray structure of dibromocannabicyclol structure of bicyclomahanimbine. J Chem Soc Chem Commun 1547–1548
Winkelblech J, Fan A, Li SM (2015) Prenyltransferases as key enzymes in primary and secondary metabolism. Appl Microbiol Biotechnol 99:7379–7397
Wu TS (1991) Murrayamine-A,-B,-C and (+)-mahanine, carbazole alkaloids from Murraya euchrestifolia. Phytochemistry 30:1048–1051
Wu TS, Huang SC (1992) Clausine-D and –F, two new 4-prenylcarbazole alkaloids from Clausena excavata. Chem Pharm Bull 40:1069–1071
Wu TS, Wang ML, Lai JS, Ito C, Furukawa H (1991) Binary carbazole alkaloids from Murraya euchrestifolia. Phytochemistry 30:1052–1054
Wu TS, Huang SC, Lai JS, Teng CM, Ko FN, Kuoh CS (1993) Chemical and antiplatelet aggregative investigation of the leaves of Clausena excavata. Phytochemistry 32:449–451
Wu TS, Huang SC, Wu PL, Lee KH (1994) Structure and synthesis of clausenaquinone A. A novel carbazolequinone alkaloid and bioactive principle from Clausena excavata. Bioorg Med Chem Lett 4:2395–2398
Wu TS, Wang ML, Wu PL, Jong TT (1995a) Two carbazole alkaloids from leaves of Murraya euchrestifolia. Phytochemistry 40:1817–1819
Wu TS, Wang ML, Wu PL (1995b) Murrayamine-O and -P, two cannabinol-skeletal carbazole alkaloids from Murraya euchrestifolia. Tetrahedron Lett 36:5385–5388
Wu TS, Wang ML, Wu PL, Ito C, Furukawa H (1996a) Carbazole alkaloids from the leaves of Murraya euchrestifolia. Phytochemistry 41:1433–1435
Wu TS, Huang SC, Wu PL (1996b) Carbazole-pyranocoumarin dimer and binary carbazole alkaloid from Clausena excavata. Tetrahedron Lett 37:7819–7822
Wu TS, Huang SC, Wu PL, Teng CM (1996c) Carbazole alkaloids from Clausena excavata and their biological activity. Phytochemistry 43:133–140
Wu TS, Huang SC, Wu PL (1996d) Carbazole alkaloids from stem bark of Clausena excavata. Phytochemistry 43:1427–1429
Wu TS, Wang ML, Wu PL (1996e) Seasonal variations of carbazole alkaloids in Murraya euchrestifolia. Phytochemistry 43:785–789
Wu TS, Huang SC, Wu PL (1997) Pyrano- and furocarbazole alkaloids from the root bark of Clausena excavata. Heterocycles 45:969–973
Wu TS, Chan YY, Liou MJ, Lin FW, Shi LS, Chen KT (1998a) Platelet aggregation inhibitor from Murraya euchrestifolia. Phytother Res 12:S80–S82
Wu TS, Huang SC, Wu PL (1998b) Lactonic carbazole alkaloids from the root bark of Clausena excavata. Chem Pharm Bull 46:1459–1461
Wu TS, Huang SC, Wu PL, Kuoh CS (1999) Alkaloidal and other constituents from the root bark of Clausena excavata. Phytochemistry 52:523–527
Wurz G, Hofer O, Greger H (1993) Structure and synthesis of phenaglydon, a new quinolone derived phenanthridine alkaloid from Glycosmis cyanocarpa. Nat Prod Lett 3:177–182
Xia HM, Yang GQO, Li CJ, Yang JZ, Ma J, Zhang D, Li Y, Li L, Zhang DM (2015) Clauemarazoles A–G, seven carbazole alkaloids from the stems of Clausena emarginata. Fitoterapia 103:83–89
Yan SY, Cui CB, Cai B, Qu GX, Yao XS (2001) New carbazole alkaloid from Clausena dunniana Levl. Chin J Med Chem 11:345–346
Yang GZ, Wu Y, Chen Y (2012) Alkaloids from the stems of Glycosmis pentaphylla. Helv Chim Acta 95:1449–1454
Yang H, Tian ST, Wu RY, Chen Y, Mei ZN, Wang CY, Yang GZ (2014) Glycoborinine induces apoptosis through mitochondrial pathway in H3pG2 cells. J Asian Nat Prod Res 16:991–999
Yenjai C, Sripontan S, Sriprajun P, Kittakoop P, Jintasirikul A, Tanticharoen M, Thebtharanonth Y (2000) Coumarins and carbazoles with antiplasmodial activity for Clausena harmandiana. Planta Med 66:277–279
Zhang FF, Gan LL, Zhou CH (2010) Synthesis, antibacterial and antifungal activities of some carbazole derivatives. Bioorg Med Chem Lett 20:1881–1884
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Greger, H. Phytocarbazoles: alkaloids with great structural diversity and pronounced biological activities. Phytochem Rev 16, 1095–1153 (2017). https://doi.org/10.1007/s11101-017-9521-5
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DOI: https://doi.org/10.1007/s11101-017-9521-5