Chemical composition and antibacterial properties of Peganum harmala L.

Document Type: Original Research Article

Authors

1 Department of Pharmacognosy, School of Pharmacy, Mashhad University of Medical Sciences, Mashhad, Iran

2 Biotechnology Research Center, Pharmaceutical Technology Institute, Mashhad University of Medical Sciences, Mashhad, Iran.

3 Pharmaceutical Control Department, School of Pharmacy, Mashhad University of Medical Sciences, Mashhad, Iran

4 Medicinal Chemistry Department, School of Pharmacy, Mashhad University of Medical Sciences, Mashhad, Iran

5 Medicinal Chemistry Department, School of Pharmacy, Mashhad University of Medical Sciences, Mashhad, Iran.

Abstract

Objective: The present study was conducted to investigate antibacterial properties of fruit and flower of Peganum harmala.
Material and Methods: Column chromatography, followed by preparative thin layer chromatography (TLC) was used for final purification. The structure of pure alkaloids was determined using spectroscopic methods (1H-NMR, 13C-NMR, UV and MS). Smoke and extract of total alkaloids were investigated for antimicrobial activity against five different microorganisms (standards and hospital isolates). The antibacterial activity was evaluated using disc diffusion assay and minimum inhibitory concentration (MIC) was determined by serial dilution methods.
Results: Chemical investigation of the chloroform extract of ripe fruit and flower of P. harmala led to identification of three alkaloids in ripe fruit and two alkaloids in the flower and leaves of this plant. Alkaloids identified in ripe fruit were harmine, peganine (vasicine) and harmaline. Two alkaloids, harmine and peganine, were detected in the flower of P. harmala, while harmaline was only found in the ripe fruit. The total alkaloids of flower were compared with total alkaloids of ripe fruit by TLC method.  Fruits and flowers had 3.12 and 3.27% alkaloid contents, respectively.
Conclusion: Our results showed that the alkaloids and smoke were specifically more effective on Candida albicans and Gram- positive bacteria (Micrococcus luteus and Staphylococcus aureus), while Gram- negative bacteria, especially Pseudomonas aeruginosa,were less sensitive.

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Main Subjects


"The plant list ", from http://www.theplantlist.org/tpl1.1/record/kew-2548698.

Abutbul S, Golan-Goldhirsh A, Barazani O, Ofir R, Zilberg D. 2005. Screening of desert plants for use against bacterial pathogens in fish. Israeli J of Aquacult, 57 71-80.

Achour S, Rhalem N, Khattabi A, Lofti H, Mokhtari A, Soulaymani A, Turcant A and Bencheikh RS. 2012. [Peganum harmala L. poisoning in Morocco: about 200 cases]. Therapie, 67:53-58.

Al-Shamma A, Drake S, Flynn DL, Mitscher L A, 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, 44:745-747.

Asgarpanah J, Ramezanloo F. 2012. Chemistry, pharmacology and medicinal properties of Peganum harmala L. Afr J Pharm Pharmacol, 6:1573-1580.

Ayoub MT, Rashan L, Khazraji A, Adaay M. 1989. An oxamide from Peganum harmala seeds. Phytochemistry, 28:2000-2001.

Benbott A, Yahyia A, Belaidi A. 2012. Assessment of the antibacterial activity of crude alkaloids extracted from seeds and roots of the plant Peganum harmala L. J Nat Prod Plant Resour, 2:568-573.

Branch S. 2012. Etymological review on chemical and pharmaceutical substances of the oriental origin. Int J Anim Veter Adv, 4:40-44.

Brossi A (1985). The alkaloids: Chemistry and pharmacology, Academic Press, pp. 140-143.

Bukhari N, Choi J, Jeon C, Park H, Kim W, Khan M, Leet S. 2008. Phytochemical studies of the alkaloids from Peganum harmala. Applied Chem, 12:101-104.

Chatterjee A, Ganguly M. 1968. Alkaloidal constituents of Peganum harmala and synthesis of the minor alkaloid deoxyvascinone. Phytochemistry, 7:307-311.

Cowan MM. 1999. Plant products as antimicrobial agents. Clin Microbiol Rev, 12:564-582.

Darabpour E, Poshtkouhian Bavi A, Motamedi H, Seyyed Nejad SM. 2011. Antibacterial activity of different parts of Peganum harmala L. growing in Iran against multi-drug resistant bacteria. EXCLIJ, 10:252-263.

Farnsworth NR. 1996. Biological and phytochemical screening of plants. J Pharm Sci, 55:225-276.

Ghasemi Pirbalouti A, Momeni M, Bahmani M. 2013. Ethnobotanical study of medicinal plants used by Kurd tribe in Dehloran and Abdanan Districts, Ilam Province, Iran. Afr J Tradit Complement Altern Med, 10:368-385.

Hemmateenejad B, Abbaspour A, Maghami H, Miri R, Panjehshahin MR. 2006. Partial least squares-based multivariate spectral calibration method for simultaneous determination of beta-carboline derivatives in Peganum harmala seed extracts. Anal Chim Acta, 575:290-299.

Herraiz T, Gonzalez D, Ancin-Azpilicueta C, Aran VJ, Guillen H. 2010. beta-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO). Food Chem Toxicol, 48:839-845.

Kaskoos R. 2014. Physico-chemical parameters, phytochemical screening and antioxidant activity of seeds of Peganum harmala collected from Iraq. Asian J Biomed Pharm Sci, 4:20-24

Lamchouri F. 2014. Antitumor properties and toxicity effects of Peganum harmala L.(Zygophyllaceae). Plant Sci Tod, 1:192-195.

Manske RY, Holmes HL. 1954. The alkaloids. Acad Press, New York, 57.

Mina CN, Farzaei MH, Gholamreza A. 2015. Medicinal properties of Peganum harmala L. in traditional Iranian medicine and modern phytotherapy: a review. J Tradit Chin Med, 35:104-109.

Mirzaie M, Nosratabadi SJ, Derakhshanfar A and Sharif I. 2007. Antileishmanial activity of Peganum harmala extract on the in vitro growth of Leishmania major promastigotes in comparison to a trivalent antimony drug. Veterinarski Arhiv, 77:365.

Moloudizargari M, Mikaili P, Aghajanshakeri S, Asghari MH, Shayegh J. 2013. Pharmacological and therapeutic effects of Peganum harmala and its main alkaloids. Pharmacogn Rev, 7:199-212.

Sharaf M, el-Ansari MA, Matlin SA, Saleh NA. 1997. Four flavonoid glycosides from Peganum harmala. Phytochemistry, 44:533-536.

Siddiqui S, Khan OY, Faizi S, Siddiqui BS. 1988. Studies in the chemical constituents of the seeds of Peganum harmala: isolation and structure elucidation of two β-carboline lactams―harmalanine and harmalacidine. Heterocycles, 27:1401-1410.

Siddiqui S, Khan O Y, Siddiqui B S and Faizi S. 1987. Harmalidine, A β-carboline alkaloid from Peganum harmala. Phytochemistry, 26:1548-1550.

Splettstoesser F, Bonnet U, Wiemann M, Bingmann D, Busselberg D. 2005. Modulation of voltage-gated channel currents by harmaline and harmane. Br J Pharmacol, 144:52-58.

Suzuki K, Nomura I, Ninomiya M, Tanaka K, Koketsu M. 2018. Synthesis and antimicrobial activity of β-carboline derivatives with N2-alkyl modifications. Bioorg Med Chem Lett, 28:2976-2978.