Isolation of bergenin from the root bark of Securinega virosa and evaluation of its potential sleep promoting effect

Document Type : Original Research Article

Authors

1 Department of Pharmacology and Therapeutics, Ahmadu Bello University, Zaria-Nigeria

2 Department of Pharmaceutical and Medicinal Chemistry, Ahmadu Bello University, Zaria-Nigeria

3 Department of Pharmaceutical and Medicinal Chemistry, Usmanu Danfodiyo University, Sokoto-Nigeria

4 Department of Pharmacology, University of Maiduguri, Maiduguri-Nigeria

Abstract

Objectives: Securinega virosa Roxb (Ex Willd) Baill (Euphorbaiceae) root bark has been reportedly used in African traditional medicine in the management of mental illnesses. Previously, the sleep-inducing potential of the crude methanol root bark of Securinega virosa extract and its butanol fraction have been reported. The study aimed to isolate and characterize the bioactive constituent that may be responsible for the sleep inducing property of the root of the plant.
Materials and Methods: The phytochemical investigation of the S. virosa root bark was carried out leading to the isolation of a compound from the butanol-soluble fraction of the methanol extract. The structure of the compound was elucidated on the basis of its spectral data, including IR, 1D and 2D NMR, mass spectrometry as well as X-ray diffraction analysis. The compound was investigated for sleep-inducing potential using diazepam-induced sleeping time test and beam walking assay in mice.
Results: This is the first report on the isolation of bergenin from the root of the plant. It significantly decreased the mean onset of sleep [F (2, 15) =7.167; P < 0.01] at the dose of 10 mg/kg, without significantly affecting the total sleep duration [F (2, 15) = 0.090, P=0.914]. Conversely, it did not significantly affect the number of foot slips at the doses of 5 and 10 mg/kg tested.
Conclusion: Bergenin isolated from the root bark of S. virosa possesses sleep-inducing property and could be partly responsible for the sedative potential of the root of S. virosa.

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Apseloff G., Hilliard JB, Gerber, N, Mays DC. 1991. Inhibition and induction of drug metabolism by psoralens: alterations in duration of sleep induced by hexobarbital and in clearance of caffeine and hexobarbital in mice. Xenobiotica, 21: 1461-1471.
Beretz A, Haag-Berrurie RM, Anton R. 1978. Choice of pharmacological methods for the study of the activities of the hawthorn. Med Plant Herbal Med, 4: 305-314.
Caldas CS, De Simone CA, Pereira MA, Malta VRS, Carvalho RLP, Da Silva TBC, Sant'ana AEG, Conserva LM. 2002. Bergenin monohydrate, a constituent of Hurmiria balsamifera, at 120 K. Acta Cryst, 58: o609-o611.
Danjuma NM, Abdu-Aguye I, Anuka JA, Hussaini IM, Zezi AU. 2009. Evaluation of anticonvulsant activity of the hydroalcoholic stem bark extract of Randia nilotica Stapf. in mice and chicks. Nig J Pharm Sci, 8: 36-45
Dehmlow EV, Guntenhoner M, Ree TV. 1999. A novel alkaloid from Fluggea virosa: 14, 15-epoxynorsecurinine. Phytochemistry, 52: 1715-1716
Dung NT, Ty PE, Taylor WC, Hoang VE. 2004. Bergenin isolated from Ficus glomerata bark. Vietnam J Chem, 42: 250-252.
Eaton WE, Badawi M, Melton B. 1995. Prodromes and precursors: epidemiologic data for primary prevention of disorders with slow onset. Am J Psychiatry, 152: 967-972
Epifano F, Molinaro G, Genovese S, Ngomba RT, Nicoletti F, Curini M. 2008. Neuroprotective effect of prenyloxycoumarins from edible vegetables. Neurosci lett, 443: 57-60.
Ford DE, Kamerow DB. 1989. Epidemiologic study of sleep disturbances and psychiatric disorders: an opportunity for prevention? JAMA, 262: 1479-1484
Fujimori H. 1965. Potentiation of barbital hypnosis as an evaluation method of central nervous system depressant. Psychopharmacology, 7: 374-397.
Gillin CJ, Seifritz E, Zoltoski RK. 2000. Basic science of sleep In: Sadock BJ, Sadock VA eds, Kaplan and Sadock׳s Comprehensive Textbook of Psychiatry (7th edition), pp. 199–209,  Philadelphia: Lippincott Williams and Wilkins,
Iketubosin GO, Mathieson DW. 1963. The isolation of hordenineandnorsecurinine from Securinega virosa. The structure of norsecurinine. J Pharm Pharmacol, 15: 810-815.
Jiang JG, Huang XJ, Chen J, Lin QS. 2007. Comparison of the sedative and hypnotic effects of flavonoids, saponins, and polysaccharides extracted from Semen Ziziphus jujube. Nat Prod Res, 21: 310-320.
Kang SY, Kim YC. 2007. Neuroprotective coumarins from the root of Angelica gigas: Structure-activity relationships. Arch Pharmacal Res, 30: 1368-1373.
Kang SY, Lee, KY, Sung SH, Kim YC. 2005. Four New Neuroprotective Dihydropyranocoumarins from Angelica gigas. J Nat Prod, 68: 56-59.
Li BH, Wu JD, Li XL. 2013. LC–MS/MS determination and pharmacokinetic study of bergenin, the main bioactive component of Bergenia purpurascens after oral administration in rats. J Pharmaceut Anal, 3: 229-234.
Lim HK, Kim HS, Choi HS, Oh S, Choi J. 2000. Hepatoprotective effects of bergenin, a major constituent of Mallotus japonicus, on carbon tetrachloride-intoxicated rats. J Ethnopharmacol, 72: 469-474.
Magaji MG, Anuka JA, Abdu-Aguye I, Yaro AH, Hussaini IM. 2008. Behavioural Effects of the methanolic root bark extract of Securinega virosa in rodents. Afr J Tradit Complement Altern Med, 5: 147-153
Magaji MG, Mohammed M, Magaji RA, Musa AM, Abdu-Aguye I, Hussaini IM. 2014. Evaluation of the Antipsychotic Potential of Aqueous Fraction of Securinega virosa Root Bark extract in mice. Metab Brain Dis, 29: 161-165
Magaji MG, Yakubu Y, Magaji RA, Yaro AH, Hussaini IM. 2014. Psychopharmacological potentials of Methanol leaf extract of Securinega virosa Roxb (Ex Willd) Baill. in mice. Pak J Biol Sci, 17: 855-859.
Magaji MG, Yaro AH, Musa AM, Anuka JA, Abdu-Aguye I, Hussaini IM. 2013. Neuropharmacological studies on ethyl acetate fraction of Securinega virosa root bark extract. Afr J Pharm Pharmacol, 7: 275-279. 
Magaji, MG, Yaro, AH, Musa, AM, Anuka, JA, Abdu-Aguye, I and Hussaini, IM. 2012. Central Depressant Activity of butanol fraction of Securinega virosa root bark in mice. J Ethnopharmacol, 141: 128-133.
McKernan RM, Rosahl TW, Reynolds DS, Sur C, Wafford KA, Atack JR, Farrar S, Myers J, Cook G, Ferris P, Garrett L, Bristow L, Marshall G, Macaulay A, Brown N, Howell O, Moore KW, Carling RW, Street LJ, Castro JL, Ragan CI, Dawson GR, Whiting PJ. 2000. Sedative but not anxiolytic properties of benzodiazepines are mediated by the GABAA receptor α1 subtype. Nature Neurosci, 3: 587-592.
Miyamoto M. 2009. Pharmacology of ramelteon, a selective MT1/MT2 receptor agonist: a novel therapeutic drug for sleep disorders. CNS Neurosci Ther, 15: 32-51.
Monkodkaew S, Loetchutinat C, Nuntasaen N, Pompimon W. 2009. Identification and Antiproliferative Activity Evaluation of a Series of Triterpenoids Isolated from Flueggea virosa (Roxb. ex Willd). Am J Appl Sci, 6: 1800-1806.
Muhammad N, Saeed M, Khan H, Adhikari A, Khan KM. 2013. Muscle Relaxant and Sedative-Hypnotic Activities of Extract of Viola betonicifolia in Animal Models Supported by Its Isolated Compound, 4-Hydroxy Coumarin. J Enzyme Inhib Med Chem, 28: 997-1001
 Najib J. 2006. Eszopiclone, a nonbenzodiazepine sedative-hypnotic agent for the treatment of transient and chronic insomnia. Clin therap, 28: 491-516.
Nasser JA, Yaacob WA, Din LB, Yamin BM, Latip J. 2009. Isolation of atranorin, bergenin and goniothalamin from Hopea sangal. ARPN J Eng Appl Sci, 4: 92-95.
Nazir N, Koul S, Qurishi MA, Taneja SC, Ahmad SF, Bani S, Qazi GN. 2007. Immunomodulatory effect of bergenin and norbergenin against adjuvant-induced arthritis—A flow cytometric study. J Ethnopharmacol, 112: 401-405.
Neuwinger JD. 1996. (translated from the German by Porter, A.). African ethnobotany-poisons and drugs, pp. 495-499, Weinheim, Germany: Chapman and Hall.
Nunomura R, Oliveira VG, Da Silva SL,  Nunomura SM. 2009. Characterization of bergenin in Endopleura uchi bark and its anti-inflammatory activity. J Braz Chem Soc, 20: 1060-1064.
Osuide G, Wambebe, C. 1980. Antagonism of pentobarbitone sleep by dopamine, levodopa and apomorphine in chicks. Clin Exp Pharmacol Physiol, 7: 237–248
Otte DM, Bilkei-Gorzó A, Filiou MD, Turck CW, Yilmaz Ö, Holst MI, Schilling K, Abou-Jamra R, Schumacher J, Benzel I, Kunz WS, Beck H, Zimmer A. 2009. Behavioral changes in G72/G30 transgenic mice. Eur Neuropsychopharmacol, 19: 339-348.
Patel DK, Patel K, Kumar R, Gadewar M, Tahilyani V. 2012. Pharmacological and analytical aspects of bergenin: a concise report. Asian Pac J Trop Biomed, 2: 163-167.
Perez GRM, Perez LJA, Garcia D LM, Sossa M H. 1998. Neuropharmacological activity of Solanum nigrum fruit. J Ethnopharmacol, 62: 43-48.
Piacente S, Pizza C, De Tommasi N, Mahmood N. 1996. Constituents of Ardisia japonica and their in vitro anti-HIV activity. J Nat Prod, 59: 565-569.
Pu HL, Huang X, Zhao JH, Hong A. 2002. Bergenin is the Antiarrhythmic Principle of Fluggea virosa . Planta Med, 68: 372-374.
Rakotonirina SV, Ngo Bum E, Rakotonirina A Bopelet M. 2001. Sedative properties of the decoction of the rhizome of Cyperus articularis. Fitoterapia, 72: 22-29.
Reynolds EH. 2003. Brain and mind: a challenge for WHO. Lancet, 361: 1924–1925.
Rolland A, Fleurentain J, Lanhers M, Younos C, Misslin R, Morier F. 1991. Behavioural effects of American traditional plant. Eschscholzia California: Sedative and anxiolytic properties. Planta Med, 57: 212-216.
Saito S, Tanaka T, Kotera K, Nakai H, Sugimoto N, Horii Z, Ikeda M, Tamura Y. 1964. Structure and stereochemistry of norsecurinine and dihydronorsecurinine. Chem Pharm Bull, 12: 1520-1523.
Sanogo R, Vassallo A, Malafronte N, Imparato S, Russo A, Dal Piaz F. 2009. New phenolic glycosides from Securinega virosa and their antioxidant activity. Nat Prod Commun, 4: 1645-1650
Silva SLD, Oliveira VGD, Yano T, Nunomura RDCS. 2009. Antimicrobial activity of bergenin from Endopleura uchi (Huber) Cuatrec. Acta Amaz, 39: 187-191.
Stanley JL, Lincoln RJ, Brown TA, McDonald LM, Dawson GR, Reynolds DS. 2005. The mouse beam walking assay offers improved sensitivity over the mouse rotarod in determining motor coordination deficits induced by benzodiazepines. J Psychopharmacol, 19: 221-227.
Takahashi H, Kosaka M, Watanabe Y, Nakade K, Fukuyama Y. 2003. Synthesis and neuroprotective activity of bergenin derivatives with antioxidant activity. Bioorg Med Chem, 11: 1781-1788.
Trampus M, Ferri N, Monopoli A, Ongini E. 1991. The dopamine D 1 receptor is involved in the regulation of REM sleep in the rat. Eur J Pharmacol, 194: 189-194.
Qu WM, Xu XH, Yan MM, Wang YQ, Urade Y, Huang ZL. 2010. Essential role of dopamine D2 receptor in the maintenance of wakefulness, but not in homeostatic regulation of sleep, in mice. J Neurosci, 30: 4382-4389.
WHO. 2001. The World Health Report. Mental health: new understanding new hope. Geneva, PP.1-15.
Zhang ZJ. 2004. Therapeutic effects of herbal extracts and constituents in animal models of psychiatric disorders, Life Sci, 75: 1659–1699.