Antioxidant activity of Haloxylon scoparium alkaloid extracts from Figuig region (southeastern of Morocco)

Authors

  • Sara Haida Laboratory of Advanced Materials and Process Engineering, Department of Chemistry, Faculty of Science, Ibn Tofail University, Kenitra, Morocco https://orcid.org/0000-0001-8776-8239
  • Abdelaziz Kribii Laboratory of Advanced Materials and Process Engineering, Department of Chemistry, Faculty of Science, Ibn Tofail University, Kenitra, Morocco
  • Naima Ait Daoud Anti Poison and Pharmacovigilance Center of Morocco, Ministry of Health, Rabat, Morocco
  • Rida Allah Belakhmima University Center of Analysis, Expertise, Technology Transfer and Incubation, Ibn Tofail University, Kenitra, Morocco
  • Abderahim Kribii Laboratory of Advanced Materials and Process Engineering, Department of Chemistry, Faculty of Science, Ibn Tofail University, Kenitra, Morocco

DOI:

https://doi.org/10.1590/s2175-97902022e19494%20

Keywords:

Haloxylon scoparium, Alkaloids, Extract, GC-MS analysis, DPPH, FRAP

Abstract

The aim of this paper is to study the chemical composition of alkaloids present in Haloxylon scoparium Pomel extracts and to evaluate their antioxidant capacity. The alkaloids were isolated from two parts of Haloxylon scoparium plant by two extraction protocols. and The quantitative study made it possible to propose the best protocol for the extraction of the alkaloids. Moreover, GC-MS analysis of alkaloid extracts allowed us to determine their chemical composition. Haloxylon scoparium contains four types of alkaloids: tetraisoquinolines, phenylethylamines, tryptolines and tryptamines. The main compounds are the tetraisoquinolines type, the predominant product of which was N-methylsalsoline. These compounds present a great interest for the researchers due to their various pharmacological and biological activities. The antioxidant effect of the different plant extracts was studied by two methods: the ferric reducing antioxidant power (FRAP) and 1,1-diphenyl-2-picryl hydrazyl free radical (DPPH·) scavenging tests. The results show that extracts of root part are more active than those from aerial part; the acetone/water extract is the most powerful. The interesting results obtained in this study will be supplemented by other analyses and biological tests in order to better valorize this plant.

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References

Ben Salah H, Jarraya R, Martin MT, Veitch NC, Grayer RJ, Simmonds MSJ, et al. Flavonol Triglycosides from the Leaves of Hammada scoparia (POMEL) ILJIN. Chem Pharm Bull. 2002;50(9):1268-1270.

Benkrief R, Brum-Bousquet M, Tillequin F, Koch M. Alkaloids and a flavonoid from aerial parts of hammada articulate ssp. Scoparia. Ann Pharm Fr. 1990;48(4):219-224.

Bhattacharya S. Reactive Oxygen Species and Cellular Defense System. V. Rani and U. C. S. Yadav, Editors. Free Radicals in Human Health and Disease. 1st ed. New Delhi: Springer; 2014. p. 17-29.

Blond A, Boutefnouchet S, Cachet X, Cottet K, Genta- Jouve G, Grougnet R, et al. Pharmacognosie, Guide de travaux pratiques 3ème année. 2013. Available from: Available from: https://docplayer.fr/17979390-Pharmacognosie-guide-de-travaux-pratiques-3eme-annee-enseignants-2013-2014.html [accessed 22 February 2018].

» https://docplayer.fr/17979390-Pharmacognosie-guide-de-travaux-pratiques-3eme-annee-enseignants-2013-2014.html

Bouaziz A, Mhalla D, Zouari I, Jlaiel L, Tounsi S, Jarraya R, et al. Antibacterial and antioxidant activities of Hammada scoparia extracts and its major purified alkaloids. S Afr J Bot. 2016;105:89-96.

Bracca ABJ, Kaufman TS. Synthetic approaches to carnegine, a simple tetrahydroisoquinoline alkaloid. Tetrahedron. 2004;60(47):10575-10610.

Bringmann G, Feineis D, Brückner R, Blank M, Peters K, Peters EM, et al. Bromal-derived tetrahydro-β-carbolines as neurotoxic agents: chemistry, impairment of the dopamine metabolism, and inhibitory effects on mitochondrial respiration. Bioorg Med Chem. 2000;8(6):1467-1478.

Buckholtz NS. Neurobiology of tetrahydro-β-carbolines. Life Sci. 1980;27(11):893-903.

Cao R, Peng W, Wang Z, Xu A. β-Carboline Alkaloids: Biochemical and Pharmacological Functions. Curr Med Chem. 2007;14(4):479-500.

Chan EWC, Lim YY, Chew YL. Antioxidant activity of Camellia sinensis leaves and tea from a lowland plantation in Malaysia. Food Chem. 2007;102(4):1214-1222.

Chaves SK, Feitosa CM, da S Araújo L. Alkaloids Pharmacological Activities - Prospects for the Development of Phytopharmaceuticals for Neurodegenerative Diseases. Curr Pharm Biotechnol. 2016;17(7):629-35.

Coutts RT, Locock RA, Slywka GWA. Mass spectra of selected beta-carbolines [β-9H-pyrido(3,4-b)indoles]. J Mass Spectrom. 1970;3(7) :879-889.

Crauste C, Vigor C, Vercauteren J. Travaux pratiques de VASAM-pharmacognosie : initiation à la reconnaissance des grandes classes de substances actives médicamenteuses d’origine végétale; 2015. Available from: Available from: http://jpm2001.free.fr/gnosie/polyTP%20VASAM%202017-18.pdf [accessed 15 December 2017].

» http://jpm2001.free.fr/gnosie/polyTP%20VASAM%202017-18.pdf

Eddouks M, Maghrani M, Lemhadri A, Ouahidi ML, Jouad H. Ethnopharmacological survey of medicinal plants used for the treatment of diabetes mellitus, hypertension and cardiac diseases in the south-east region of Morocco (Tafilalet). J Ethnopharmacol. 2002;82(2-3):97-103.

El Shaer HM. Halophytes and salt-tolerant plants as potential forage for ruminants in the Near East region. Small Rumin Res. 2010;91(1):3-12.

El-Shazly A, Wink M. Tetrahydroisoquinoline and β-Carboline Alkaloids from Haloxylon articulatum (Cav.) Bunge (Chenopodiaceae). Z Naturforsch C. 2003;58:477-480.

Estevinho L, Pereira AP, Moreira L, Dias LG, Pereira E. Antioxidant and antimicrobial effects of phenolic compounds extracts of Northeast Portugal honey. Food Chem Toxicol. 2008;46(12):3774-3779.

Fennane M, Ibn Tattou M, Mathez J, Ouyahya A, El oualidi J. Flore pratique du Maroc. Manuel de détermination des plantes vasculaires. Volume 1. Travaux de l’Institut Scientifique Série Botanique, n° 36, Rabat, Maroc; 1999.

Gupta PK, Barone G, Gurley BJ, Fifer EK, Hendrickson HP. Hydrastine Pharmacokinetics and Metabolism after a Single Oral Dose of Goldenseal (Hydrastiscanadensis) to Humans. Drug Metab Dispos. 2015;43(4):534-552.

Herraiz T, Galisteo J. Tetrahydro-β-carboline Alkaloids Occur in Fruits and Fruit Juices. Activity as Antioxidants and Radical Scavengers. J Agric Food Chem. 2003;51(24):7156-7161.

Herraiz T. Analysis of Tetrahydro-β-carbolines and Their Precursors by Electron Ionization Mass Spectrometry. Identification in Foodstuffs by Gas Chromatography/ Mass Spectrometry. Rapid Commun Mass Spectrom. 1997;11(7):762-768.

Irsfeld M, Spadafore M, Prüß BM. β-phenylethylamine, a small molecule with a large impact. Webmed Central. 2013;4(9):4409.

Jarraya RM, Bouaziz A, Hamdi B, Ben Salah A, Damak M. N-Methylisosalsoline from Hammada scoparia. Acta Crystallogr Sect E. 2008;64(9):o1714-o1714.

Jerkovic I, Mastelic J. GC-MS Characterization of Acetylated b-D-glucopyranosides: Transglucosylation of Volatile Alcohols Using Almond b-glucosidase. Croat Chem Acta. 2004;77(3):529-535.

Jung HA, Min BS, Yokozawa T, Lee JH, Kim YS, Choi JS. Anti-Alzheimer and Antioxidant Activities of Coptidis Rhizoma Alkaloids. Biol Pharm Bull. 2009;32(8):1433-1438.

Li Y, Plitzko I, Zaugg J, Hering S, Hamburger M. HPLC- Based Activity Profiling for GABAA Receptor Modulators: A New Dihydroisocoumarin from Haloxylon scoparium. J Nat Prod. 2010;73(4):768-770.

Lobo V, Patil A, Phatak A, Chandra N. Free radicals, antioxidants and functional foods: Impact on human health. Pharmacogn Rev. 2010;4(8):118-126.

Mezghani-Jarraya R, Hammami H, Ayadi A, Damak M. Molluscicidal activity of Hammada scoparia (Pomel) Iljin leaf extracts and the principal alkaloids isolated from them against Galba truncatula. Mem Inst Oswaldo Cruz. 2009;104(7):1035-1038.

Nichols DE, Nichols CD. Serotonin Receptors. Chem Rev. 2008;108(5):1614-1641.

Olugbami JO, Gbadegesin MA, Odunola OA. In vitro free radical scavenging and antioxidant properties of ethanol extract of Terminalia glaucescens. Phcog Res. 2015;7(1):49-56.

Oyaizu M. Studies on products of browning reaction. Antioxidative activities of products of browning reaction prepared from glucosamine. Jpn J Nutr Diet. 1986;44(6):307-315.

Ramya R, Kalaiselvi M, Narmadha R, Gomathi D, Bhuvaneshwari V, Amsaveni R, Devaki K. Secondary metabolite credentials and in vitro free radical scavenging activity of Alpinia calcarata. J Acute Med. 2015;5(2):33-37.

Sarmadi BH, Ismail A. Antioxidative peptides from food proteins: A review. Peptides. 2010;31(10):1949-1956.

Sathiyamoorthy P, Lugasi-Evgi H, Van-Damme P, Abu- Rabia A, Gopas J, Golan-Goldhirsh A. Larvicidal Activity in Desert Plants of the Negev and Bedouin Market Plant Products. Int J Pharmacogn. 1997;35(4):265-273.

Seijas JA, Vázquez-Tato MP, Martínez MM. β-Phenylethylamines, Indolines and Isoquinolones via Hydroamination of Styrenes by Microwave Irradiation. Synlett. 2001;(06):0875-0877.

Singh RP, Chidambara Murthy KN, Jayaprakasha GK. Studies on the antioxidant activity of pomegranate (Punica granatum) peel and seed extracts using in vitro models. J Agric Food Chem. 2002;50(1):81-86.

Tadeusz A. Alkaloids-Secrets of Life: Alkaloid Chemistry, Biological Significance, Applications and Ecological Role. First edition. Amsterdam; Oxford: Elsevier; 2007. 316 p.

Tiong SH, Looi CY, Hazni H, Arya A, Paydar M, Wong WF, et al. Antidiabetic and Antioxidant Properties of Alkaloids from Catharanthus roseus (L.) G. Don. Molecules. 2013;18(8):9770-9784.

Tomas Herraiz T. Tetrahydro-β-carboline Bioactive Alkaloids in Beverages and Foods. American Chemical Society, editor. Nutraceutical Beverages. Washington: ACS Publications; 2003. p. 405-426.

Zanetta JP, Pons A, Iwersen M, Mariller C, Leroy Y, Timmerman P, et al. Diversity of sialic acids revealed using gas chromatography/mass spectrometry of heptafluorobutyrate derivatives. Glycobiology. 2001;11(8):663-676.

Ziani BEC, Calhelha RC, Barreira JCM, Barros L, Hazzit M, Ferreira ICFR. Bioactive properties of medicinal plants from the Algerian flora: Selecting the species with the highest potential in view of application purposes. Ind Crop Prod. 2015;77:582-589.

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Published

2022-11-23

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Original Article

How to Cite

Antioxidant activity of Haloxylon scoparium alkaloid extracts from Figuig region (southeastern of Morocco). (2022). Brazilian Journal of Pharmaceutical Sciences, 58. https://doi.org/10.1590/s2175-97902022e19494