Recent pharmacological developments in β-carboline alkaloid "harmaline"

European Journal of Pharmacology

Volumn 721, Issue 1-3, 2013, Pages 391-394

  Khan, Farhan A ^a   Maalik, Aneela ^a   Iqbal, Zafar ^a   Malik, Imran ^a  

^a COMSATS Institute of Information Technology ^*  (Pakistan)

Author keywords

Antileishmanial; Antitumor; Harmaline; Peganum harmala; Plasmodium; Vasorelaxant

Indexed keywords

ALKALOID; BETA CARBOLINE DERIVATIVE; HARMALINE; HARMALOL; HARMAN; HARMINE; HARMOL;

ANTIMALARIAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIPROTOZOAL ACTIVITY; CYTOTOXICITY; DOSE RESPONSE; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG POTENCY; DRUG STRUCTURE; HYPOTHERMIA; NONHUMAN; PEGANUM HARMALA; PRIORITY JOURNAL; REVIEW; STRUCTURE ACTIVITY RELATION; THROMBOCYTE AGGREGATION; VASODILATATION;

ANTILEISHMANIAL; ANTITUMOR; HARMALINE; PEGANUM HARMALA; PLASMODIUM; VASORELAXANT;

ANIMALS; DRUG DISCOVERY; HARMALINE; HUMANS;

EID: 84890117262     PISSN: 00142999     EISSN: 18790712     Source Type: Journal    
DOI: 10.1016/j.ejphar.2013.05.003     Document Type: Article

References (39)

1. A.F.M. Abdelfattah, K. Matsumoto, H.A.K. Gammaz, and H. Watanabe Hypothermic effect of harmala alkaloid in rats - involvement of serotonergic mechanism Pharmacol. Biochem. BE 52 1995 421 426
2. J. Adachi, Y. Mizoi, T. Naito, K. Yamamoto, S. Fujiwara, and I. Ninomiya Determination of beta-carbolines in foodstuffs by high-performance liquid chromatography and high-performance liquid chromatography-mass spectrometry J. Chromatogr. 538 1991 331 339
3. M.M. Airaksinen, and I. Kari Beta-carbolines, psychoactive compounds in the mammalian body. Part II. Effects Medical Biology 59 1981 190 211 (Pubitemid 12102769)
4. T.A. al-Allaf, R.F. Khuzaie, L.J. Rashan, and W.F. Halaseh Cytotoxic activity against a series of tumour cell lines of dimethyltin dichloride complexes with various donor ligands Boll. Chim. Farm. 138 1999 267 271 (Pubitemid 29372120)
5. N. Arshad, C. Neubauer, S. Hasnain, and M. Hess Peganum harmala can minimize Escherichia coli infection in poultry, but long-term feeding may induce side effects Poult. Sci. 87 2008 240 249 (Pubitemid 351198488)
6. N. Arshad, K. Zitterl-Eglseer, S. Hasnain, and M. Hess Effect of Peganum harmala or its beta-carboline alkaloids on certain antibiotic resistant strains of bacteria and protozoa from poultry Phytother. Res. 22 2008 1533 1538 (Pubitemid 352789625)
7. J. Asgarpanah, and F. Ramezanloo Chemistry, pharmacology and medicinal properties of Peganum harmala L. AFR J. Pharm. Pharmacol. 6 2012 1573 1580
8. A. Astulla, K. Zaima, Y. Matsuno, Y. Hirasawa, W. Ekasari, A. Widyawaruyanti, N.C. Zaini, and H. Morita Alkaloids from the seeds of Peganum harmala showing antiplasmodial and vasorelaxant activities J. Nat. Med. 62 2008 470 472
9. S. Begum, B. Usmani, B.S. Siddiqui, S.A. Saeed, S. Farnaz, K.A. Khan, S.A. Khan, S.M. Khalid, and A. Zia Chemistry and biological activity of a tryptamine and beta-carboline series of bases Arzneim. Forsch. 46 1996 1163 1168 (Pubitemid 27010602)
10. H. Berrougui, C. Martin-Cordero, A. Khalil, M. Hmamouchi, A. Ettaib, E. Marhuenda, and M.D. Herrera Vasorelaxant effects of harmine and harmaline extracted from Peganum harmala L. seed's in isolated rat aorta Pharmacol. Res. 54 2006 150 157 (Pubitemid 44038386)
11. J. Bruinvels Comparison of intracisternally and intraperitoneally injected harmaline on body temperature and tremor in the rat J. Pharm. Pharmacol. 21 1969 506 508
12. C. Di Giorgio, F. Delmas, E. Ollivier, R. Elias, G. Balansard, and P. Timon-David In vitro activity of the β-carboline alkaloids harmane, harmine, and harmaline toward parasites of the species Leishmania infantum Exp. Parasitol. 106 2004 67 74 (Pubitemid 38686275)
13. R. Cao, W. Peng, Z. Wang, and A. Xu beta-Carboline alkaloids: biochemical and pharmacological functions Curr. Med. Chem. 14 2007 479 500
14. D. Douer New advances in the treatment of acute promyelocytic leukemia Int. J. Hematol. 2 2002 179 187
15. M.A.M. El Gendy, A.A. Soshilov, M.S. Denison, and A.O.S. El-Kadi Harmaline and harmalol inhibit the carcinogen-activating enzyme CYP1A1 via transcriptional and posttranslational mechanisms Food Chem. Toxicol. 50 2012 353 362
16. A.T. Evans, and S.L. Croft Antileishmanial activity of harmaline and other tryptamine derivatives Phytother. Res. 1 1987 25 27
17. L. Farouk, A. Laroubi, R. Aboufatima, A. Benharref, and A. Chait Evaluation of the analgesic effect of alkaloid extract of Peganum harmala L.: possible mechanisms involved J. Ethnopharmacol. 115 2008 449 454 (Pubitemid 350299085)
18. G. Grimaldi Jr., R.B. Tesh, and D. McMahon-Pratt A review of the geographic distribution and epidemiology of leishmaniasis in the New World Am. J. Trop. Med. Hyg. 41 1989 687 725 (Pubitemid 20022744)
19. Goegel Isolation of harmalol and harmaline form Peganum harmala Annalen 38 1841 363
20. H. Hussain, S. Specht, S.R. Sarite, A. Hoerauf, and K. Krohn New quinoline-5,8-dione and hydroxynaphthoquinone derivatives inhibit a chloroquine resistant Plasmodium falciparum strain Eur. J. Med. Chem. 54 2012 936 942
21. J.H. Im, Y.R. Jin, J.J. Lee, J.Y. Yu, X.H. Han, S.H. Im, J.T. Hong, H.S. Yoo, M.Y. Pyo, and Y.P. Yun Antiplatelet activity of beta-carboline alkaloids from Perganum harmala: a possible mechanism through inhibiting PLCgamma2 phosphorylation Vasc. Pharmacol. 50 2009 147 152
22. J. Ishida, H.K. Wang, K.F. Bastow, C.Q. Hu, and K.H. Lee Antitumor agents 201. Cytotoxicity of harmine and beta-carboline analogs Bioorg. Med. Chem. Lett. 9 1999 3319 3324
23. J.D. Jordan, and J.R. Carhuapoma Hypothermia: comparing technology J. Neurol. Sci. 261 2007 35 38 (Pubitemid 47313493)
24. M. Kartal, M.L. Altun, and S. Kurucu HPLC method for the analysis of harmol, harmalol, harmine and harmaline in the seeds of Peganum harmala L. J. Pharm. Biomed. 31 2003 263 269 (Pubitemid 36254808)
25. F. Lamchouri, A. Settaf, Y. Cherrah, M. Hassar, M. Zemzami, N. Atif, E.B. Nadori, A. Zaid, and B. Lyoussi In vitro cell-toxicity of Peganum harmala alkaloids on cancerous cell-lines Fitoterapia 71 2000 50 54 (Pubitemid 30012017)
26. X.-J. Luo, J. Peng, and Y.-J. Li Recent advances in the study on capsaicinoids and capsinoids Eur. J. Pharmacol. 650 2011 1 7
27. C.M. Mang'era, F.N. Mbai, I.A. Omedo, P.O. Mireji, and S.A. Omar Changes in genotypes of Plasmodium falciparum human malaria parasite following withdrawal of chloroquine in Tiwi, Kenya Acta Trop. 123 2012 202 207
28. Y. Nakagawa, T. Suzuki, H. Ishii, A. Ogata, and D. Nakae Mitochondrial dysfunction and biotransformation of β-carboline alkaloids, harmine and harmaline, on isolated rat hepatocytes Chem-Biol. Interact. 188 2010 393 403
29. Z.S. Saify, J. Farhad, N. Mushtaq, F. Noor, S. Takween, and S. Akhtar Effect of diazepam on the CNS excitation and behavioural changes induced by harmaline and its newly synthesized analogues Pak. J. Pharm. Sci. 17 2004 31 36
30. S. Sanon, E. Ollivier, N. Azas, V. Mahiou, M. Gasquet, C.T. Ouattara, I. Nebie, A.S. Traore, F. Esposito, G. Balansard, P. Timon-David, and F. Fumoux Ethnobotanical survey and in vitro antiplasmodial activity of plants used in traditional medicine in Burkina Faso J. Ethnopharmacol. 86 2003 143 147 (Pubitemid 36542868)
31. T. Schmeller, and M. Wink M.F. Roberts, M. Wink, Biochemistry, Ecology and Medicinal Application 1998 Plenum Press New York 435 459
32. C.C. Shi, J.F. Liao, and C.F. Chen Comparative study on the vasorelaxant effects of three harmala alkaloids in vitro Jpn. J. Pharmacol. 85 2001 299 305
33. F.R. Shourmasti, I. Goudarzi, T. Lashkarbolouki, K. Abrari, M.E. Salmani, and A. Goudarzi Effects of riluzole on harmaline induced tremor and ataxia in rats: biochemical, histological and behavioral studies Eur. J. Pharmacol. 695 2012 40 47
34. I.D. Spenser A synthesis of harmaline Can. J. Chem. 37 1959 1851 1858
35. K.M. Wasan, E.K. Wasan, P. Gershkovich, X.H. Zhu, R.R. Tidwell, K.A. Werbovetz, J.G. Clement, and S.J. Thornton Highly effective oral amphotericin b formulation against murine visceral leishmaniasis J. Infect. Dis. 200 2009 357 360
36. Y.Z. Xiang, L.Y. Kang, X.M. Gao, H.C. Shang, J.H. Zhang, and B.L. Zhang Strategies for antiplatelet targets and agents Thromb. Res. 123 2008 35 49
37. F. Zaker, A. Oody, and A. Arjmand A study on the antitumoral and differentiation effects of peganum harmala derivatives in combination with ATRA on leukaemic cells Arch. Pharm. Res. 30 2007 844 849
38. T. Zhao, Y.Q. He, J. Wang, K.M. Ding, C.H. Wang, and Z.T. Wang Inhibition of human cytochrome P450 enzymes 3A4 and 2D6 by beta-carboline alkaloids, harmine derivatives Phytother. Res. 25 2011 1671 1677
39. T. Zhao, S.S. Zheng, B.F. Zhang, Y.Y. Li, S.W.A. Bligh, C.H. Wang, and Z.T. Wang Metabolic pathways of the psychotropic-carboline alkaloids, harmaline and harmine, by liquid chromatography/mass spectrometry and NMR spectroscopy Food Chem. 134 2012 1096 1105