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01-10-2008 | Natural Medicine Note

Alkaloids from the seeds of Peganum harmala showing antiplasmodial and vasorelaxant activities

Authors: Adil Astulla, Kazumasa Zaima, Yosuke Matsuno, Yusuke Hirasawa, Wiwied Ekasari, Aty Widyawaruyanti, Noor Cholies Zaini, Hiroshi Morita

Published in: Journal of Natural Medicines | Issue 4/2008

Abstract

Bioassay-guided purification from the seeds of Peganum harmala led to the isolation of harmine (1), harmaline (2), vasicinone (3), and deoxyvasicinone (4). Harmine (1) and harmaline (2) showed a moderate in vitro antiplasmodial activity against Plasmodium falciparum. Quinazoline alkaloid, vasicinone (3), showed a vasorelaxant activity against phenylephrine-induced contraction of isolated rat aorta.

Wang C, Liu J, Zheng L, Lin Y, Zou X, Chen M, Sun D (2002) Analysis of harmine and harmaline in different parts of Peganum harmala form different areas. Zhongguo Yaoxue Za Zhi 37:211–215

El-Saad EM (1980) Peganum harmala: its use in certain dermatoses. Int J Dermatol 19:221–222CrossRef

Grosso DS, Gawienowski AM (1976) Inhibition of mitochondrial monoamine oxidase of the rat uterus and liver by clorgyline, pargyline and harmine. Biochem Pharmacol 25:957–961PubMedCrossRef

Sanchez-Ramos JR (1991) Banisterine and Parkinson’s disease. Clin Neuropharmacol 14:391–402PubMedCrossRef

Airaksinen MM, Kari I (1981) β-Carbolines, psychoactive compounds in the mammalian body. Part II: effects. Med Biol 59:190–211PubMed

Gaviraj EN, Babu GR, Murthy UD (1998) An antibacterial activity-guided isolation of harmine from Peganum harmala seeds by bioautography. Indian Drugs 35:471–474

Al-Shamma A, Drake S, Flynn DL, Mitscher LA, Park YH, Rao GS, Simpson A, Swayze JK, Veysoglu T, Wu ST (1981) Antimicrobial agents from higher plants. Antimicrobial agents from Peganum harmala seeds. J Nat Prod 44:745–747PubMedCrossRef

Berrougui H, Lopez-Lazaro M, Martin-Cordero C, Mamouchi M, Ettaib A, Herrera MD (2005) Cytotoxic activity of methanolic extract and two alkaloids extracted from seeds of Peganum harmala L. J Natl Remedies 5:41–45

Chen Q, Chao R, Chen H, Hou X, Yan H, Zhou S, Peng W, Xu A (2005) Antitumor and neurotoxic effects of novel harmine derivatives and structure-activity relationship analysis. Int J Cancer 114:675–682PubMedCrossRef

10.

Wang XW, Xie H (1999) Antineoplastic alkaloids from Peganum harmala. Drugs Future 24:1333–1337CrossRef

11.

Liu J, Zhao G (2005) Effects of Peganum harmala extract on the growth and antioxidase activity of wheat seedlings. Xibei Zhiwu Xuebao 25:1756–1760

12.

Sobhani AM, Ebrahimi S-A, Mahmoudian M (2002) An in vitro evaluation of human DNA topoisomerase I inhibition by Peganum harmala L. seeds extract and its beta-carboline alkaloids. J Pharm Pharm Sci 5:19–23PubMed

13.

Bian D, Li G, Zhang H (1987) Effects of harmine on the immune function of mice. Zhongguo Yaoli Xuebao 8:477–480PubMed

14.

Berrougui H, Martin-Cordero C, Khalil A, Hmamouchi M, Ettaib A, Marhuenda E, Herrera MD (2006) Vasorelaxant effects of harmine and harmaline extracted from Peganum harmala L. seeds in isolated rat aorta. Pharmacol Res 54:150–157PubMedCrossRef

15.

Shi CC, Liao JF, Chen CF (2001) Comparative study on the vasorelaxant effects of three harmala alkaloids in vitro. Jpn J Pharmacol 85:299–305PubMedCrossRef

16.

Lala S, Pramanick S, Mukhopadhyay S, Bandyopadhyay S, Basu MK (2004) Harmine: evaluation of its antileishmanial properties in various vesicular delivery systems. J Drug Target 12:165–175PubMedCrossRef

17.

Di GC, Delmas F, Ollivier E, Elias R, Balansard G, Timon-David P (2004) In vitro activity of the β-carboline alkaloids harmane, harmine, and harmaline toward parasites of the species Leishmania infantum. Exp Parasitol 106:67–74CrossRef

18.

Morita H, Oshimi S, Hirasawa Y, Koyama K, Honda T, Ekasari W, Indrayanto G, Zaini NC (2007) Cassiarins A and B, novel antiplasmodial alkaloids from Cassia siamea. Org Lett 9:3691–3693PubMedCrossRef

19.

Morita H, Eda M, Iizuka T, Hirasawa Y, Sekiguchi M, Yun YS, Itokawa H, Takeya K (2006) Structure of a new cyclic nonapeptide, segetalin F and vasorelaxant activity of segetalins from Vaccaria segetalis. Bioorg Med Chem Lett 17:4458–4461CrossRef

20.

Morita H, Iizuka T, Choo CY, Chan KL, Takeya K, Kobayashi J (2006) Vasorelaxant activity of cyclic peptide, cyclosquamosin B, from Annona squamosa. Bioorg Med Chem Lett 16:4609–4611PubMedCrossRef

21.

Pandita K, Bhatia MS, Thappa RK, Agarwal SG, Dhar KL, Atal CK (1983) Seasonal variation of alkaloids of Adhatoda vasica and detection of glycosides and N-oxides of vasicine and vasicinone. Planta Med 48:81–82PubMedCrossRef

22.

Joshi BS, Newton MG, Lee DW, Barber AD, Pelletier SW (1996) Reversal of Absolute stereochemistry of the pyrrolo[2, 1-b]quinazoline alkaloids vasicine, vasicinone, vasicinol and vasicinolone. Tetrahedron Asymmetry 7:25–28CrossRef

23.

Mbatchi SF, Mbatchi B, Banzouzi JT, Bansimba T., Nsonde NGF, Ouamba JM, Berry A, Benoit VF (2006) In vitro antiplasmodial activity of 18 plants used in Congo Brazzaville traditional medicine. J Ethnopharmacol 104:168–174PubMedCrossRef

24.

Sanon S, Ollivier E, Azas N, Mahiou V, Gasquet M, Ouattara CT, Nebie I, Traore AS, Esposito F, Balansard G, Timon DP, Fumoux F (2003) Ethnobotanical survey and in vitro antiplasmodial activity of plants used in traditional medicine in Burkina Faso. J Ethnopharmacol 86:143–147PubMedCrossRef

25.

Trager W, Jensen JB (1976) Human malaria parasites in continuous culture. Science 193:673–675PubMedCrossRef

26.

Budimulja AS, Syafruddin Tapchaisri P, Wilairat P, Marzuki S (1997) The sensitivity of Plasmodium protein synthesis to prokaryotic ribosomal inhibitors. Mol Biochem Parasitol 84:137–141PubMedCrossRef

Title: Alkaloids from the seeds of Peganum harmala showing antiplasmodial and vasorelaxant activities
Authors: Adil Astulla
Kazumasa Zaima
Yosuke Matsuno
Yusuke Hirasawa
Wiwied Ekasari
Aty Widyawaruyanti
Noor Cholies Zaini
Hiroshi Morita
Publication date: 01-10-2008
Publisher: Springer Japan
Published in: Journal of Natural Medicines / Issue 4/2008
Print ISSN: 1340-3443
Electronic ISSN: 1861-0293
DOI: https://doi.org/10.1007/s11418-008-0259-7

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Alkaloids from the seeds of Peganum harmala showing antiplasmodial and vasorelaxant activities

Abstract

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