Liquid Chromatography-Mass Spectrometric Analyses of Potential Antioxidant Constituents from Zanthoxylum zanthoxyloides Leaves: Probing into the Role of Alkaloids doi.org/10.26538/tjnpr/v4i10.26
Main Article Content
Abstract
Zanthoxylum zanthoxyloides is a plant used traditionally as food and in medicine, with known antioxidant properties. The study aimed to prepare n-butanol fractions of Z. zanthoxyloides leaves and evaluate their in-vitro antioxidant potential. Vacuum liquid chromatography (VLC) was used to separate the constituents of the n-butanol fraction using gradients of binary mixtures of dichloromethane in methanol (1L) sequentially in the ratios; 9:1 (BF1), 7:3 (BF2), 5:5 (BF3), 3:7 (BF4), and 1:9 (BF5). Three standard antioxidant assay models were adopted for the in-vitro antioxidant activity. Ascorbic acid (53.60%) exhibited superior antioxidant activity relative to the n-butanol sub-fractions; (BF1 14.51%, BF2 24.76%, BF3 10.90%, BF4 6.19% and BF5 23.38%). Meanwhile, BF3 displayed superior reducing potential relative to ascorbic acid using both the TAC and FRAP method (TAC 2.320 ± 0.002; FRAP 2.27 ± 0.002 versus TAC 0.298 ± 0.000; FRAP 0.274 ± 0.002). BF1, BF2, BF4 and BF5 displayed lower reducing potential: TAC 0.202 ± 0.001; FRAP 0.199 ± 0.000, TAC 0.162 ± 0.001; FRAP 0.153 ± 0.001, TAC 0.186 ± 0.002; FRAP 0.174 ± 0.002 and TAC 0.262 ± 0.000; FRAP 0.223 ± 0.003, respectively when compared to ascorbic acid. Several known potential antioxidants were tentatively characterized in the n-butanol sub-fractions by liquid chromatography-mass spectrometry (LC-MS) dereplication. However, a significant number of alkaloids and phenolic compounds unknown for any role in radical scavenging activity (RSA) were detected in n-butanol sub-fractions. Our findings also further probed the possible role of alkaloids in antioxidant cascade.
Article Details
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
References
Onwudiwe NN, Njoku OU, Nwodo FC, Parker JE, Ogugofor MO. Evaluation of the nutritional compositions and analgesic effects of the flavonoid fraction of Eugenia uniflora Ripe Fruit Pulp. Am J Ethnomed. 2018; 5(1):1-8.
Al-snafi AE. Medicinal plants with anticancer effects (Part 2)-Plant based review. Sch Acad J Pharm. 2016; 5(5):175- 193.
Anne IO, Andrew OO, Idu M. Phytochemistry and antimicrobial activity of Zanthoxylum zanthoxyloides root used as chewing stick in Nigeria. J Phytopharm. 2013; 2(6):1-7.
Chakrabarty B, Acharyya RN, Kundu N, Mahmud I, Hossain H, Biswas NN, Uddin SJ, Dev S, Das AK. Evaluation of Anti-Diabetic and Anti-Allergic Activities of Brownlowia tersa (L.) kosterm leaves Extract and Determination of its Phenolic Compounds by HPLC-DAD. Trop J Nat Prod Res. 2020; 4(8):326-333.
Balunas MJ and Kinghorn AD. Drug discovery from medicinal plants. Life Sci. 2005; 78:431-441.
Henda K, Sahla B, Lobna J, Abdelfattah EF, Mohamed D, Sami S, Noureddine A. LC-MS–MS and GC-MS analyses of biologically active extracts and fractions from Tunisian Juniperusphoenice leaves, Pharm Biol., 2016; 55(1):88-95.
Uzor PF, Nnadi CO, Ahiabuike JE, Ani HN. Antidiabetic studies and dereplication of the bioactive constituents of Anthocleista nobilis. G. Don by UHPLC/ESI-QTOF-MS. Dhaka Univ J Pharm Sci. 2018; 17(1):19-28.
Gan J, Feng Y, Zhao H, Xian L, Zhang H. Correlations between antioxidant activity and alkaloids and phenols of Maca (Lepidium meyenii). J Food Chem. 2017; 2017:1-10.
He XG. On-line identification of phytochemical constituents in botanical extracts by combined high performance liquid chromatographic–diode array detectionmass spectrometric techniques. J Chromatog A. 2000; 880:203–232.
Fabre N, Rustan I, Hoffman E, Quetin-Leclercq J. Determination of flavone, flavonol and flavanone aglycones by negative liquid chromatography ion trap mass spectrometry; J Am Soc Mass Spec. 2001; 12:707-715.
Ye M, Yan Y, Guo DA. Characterization of phenolic compounds in the Chinese herbal drug, Tu-Si-Zi by liquid chromatography coupled to electrospray ionization mass spectrometry. Rapid Comm Mass Spec. 2005; 19:1469- 1484.
Zhong L, Wang L, Yang G, Shi H, Jiang C, Liu W, et al. Study on the determination of polyphenols in tobacco by HPLC coupled with ESI-MS after solid-phase extraction. J Chromatog Sci. 2003; 41(1):36-40.
Cyckens F and Claeys M. Mass spectrometry in the structural analysis of flavonoids. J Mass Spec. 2004; 39:1- 15.
Yuan H, Ma Q, Ye L, Piao G. The Traditional Medicine and Modern Medicine from Natural Products. Molecules. 2016; 599:1-18.
Al-snafi AE. Medicinal plants with antioxidant and free radical scavenging effects (Part 2): Plant based review. IOSR J Pharm. 2016; 6(7):62-82.
Altemimi A, Lakhssassi N, Baharlouei A, Watson DG. Phytochemicals: Extraction, isolation, and identification of bioactive compounds from plant extracts. Plants. 2017; 6(42):1–23.
Wüst A, Aydi A, Arauco M, Bolzan A, Barth D. Solvent extraction and purification of rosmarinic acid from supercritical fluid extraction fractionation waste : Economic evaluation and scale-up. J Supercrit Fluids. 2013; 83:133- 145.
Mir MA, Zahoor I, Shafi A. Isolation, Characterization and Bioactivities of Sambucus wightiana derived Dotriacontanoic acid. Int J Trend Sci Res Dev. 2017; 1(6):1323-1332.
Mohandas GG and Kumaraswamy M. Antioxidant activities of terpenoids from Thuidium tamariscellum (C. Muell.) Bosch and Sande-Lac. a Moss. Pharmacog J. 2018; 10(4):645-649.
Pratima NA and Gadikar R. Liquid Chromatography-Mass Spectrometry and Its Applications: A Brief Review. Arch Org Inorg Chem Sci. 2018; 1(1):1–9.
Adeniran AA, Sonibare MA, Ajayi OS, Rajacharya GH, Kumar S. Antioxidant Activity of column fractions and Caryatin isolated from the ethyl acetate extract of Dioscorea hirtiflora tuber. Trop J Nat Prod Res. 2020; 4(7):276-281.
Mukhtar AE, Abubaka A, Chukwubuike OG. In vitro Antioxidant Activities of Different Stem Bark Extracts of Irvingia gabonensis (Irvingiaceae). Trop J Nat Prod Res. 2020; 4(6):223-227
Aloke C, Nwachukwu N, Ugwuja EI, Idenyi JN, Nwachi EU, Obasi IO, et al. Effects of Zanthoxylum zanthoxyloides leaves on blood glucose, lipid profile and some liver enzymes in alloxan induced diabetic rats. Int J Sci Nat. 2012; 3(3):497–501.
Boye A, Koffuor GA, Boampong JN, Amoateng P, Ameyaw EO, Ansah EO, et al. Gastroprotective Effect and Safety Assessment of Zanthoxylum Zanthoxyloides (Lam) Waterm Root Bark Extract. Am J Pharmacol Toxicol. 2012; 7(2):73-80.
Ouédraogo L, Nacoulma AP, Compaoré M, Lagnika L, Kiendrebeogo M. Stem bark of Zanthoxylum zanthoxyloïdes a possible substitute of root bark for the conservation of the species in Burkina Faso. African J Biotechnol. 2019; 18(9):197-205.
Tine Y, Yang Y, Renucci F, Costa J, Wele A, Paolini J. LCMS / MS analysis of flavonoid compounds from Zanthoxylum zanthoxyloides extracts and their antioxidant activities. Nat Prod Commun. 2017; 12(12):1865-1868.
Adekunle AS, Kamdem J, Rocha JB. Antioxidant activity and HPLC analysis of Zanthoxylum zanthoxyloides. Rep Opin. 2012; 4:6-13.
Yoro T, Renucci F, Costa J, Wele A, Paolini J. A method of LC-MS/MS profiling of coumarins in Zanthoxylum zanthoxyloides (Lam.), B. Zepernich and timber extracts and essential oils. Molecules. 2017; 22:174.
Ayoka TO, Nwachukwu N, Nnadi CO. Identification of potential antioxidant and hepatoprotective constituents of Vitex doniana by UHPLC/+ESI-QQTOF-MS/MS analysis. Asian J Pharm Clin Res. 2020; 13(8):142-148.
Pluskal T, Castillo S, Villar-Briones A, Oresic M. 2: Modular framework for processing, visualizing, and analyzing mass spectrometry-based molecular profile data. BMC bioinformatics. 2010; 11:395.
Shiqi P. Methods and Applications of Antioxidant Activity Assays. In: Pharmaceutical bioassay: Methods and Applications. John Wiley & Sons, Inc, New York, 2009; 205-218.
Cleophas TJ, Zwinderman AH. SPSS for Starters and 2nd Levelers. Second Ed. Springer; 2016. 47 p.
Airaodion AI, Ogbuagu EO, Ogbuagu U, Adeniji AR, Agunbiade AP, Airaodion EO. Hepatoprotective Effect of Parkia biglobosa on Acute Ethanol-induced Oxidative Stress in Wistar Rats. Int Res J Gastroenterol Hepatol. 2019; 2(1):1-11.
Ibrahim AK and Al-azawi AH. Hepatoprotective effect of (Arachis hypogea L.) peanut skin extracts on CCl4 induced liver damage in mice. Biosci Res. 2018; 15(4):3415-3428.
Chaaib F, Queiroz EF, Ndjoko K, Diallo D, Hostettmann K. Antifungal and antioxidant compounds from the root bark of Fagara zanthoxyloides. Planta Med. 2003; 69:316-320.
Negi J, Bisht V, Bh A, Singh P, Sundriyal R. Chemical constituents and biological activities of the genus Zanthoxylum: a review. J Pure Appl Chem. 2011; 5:412– 416.
Patino LOJ, Prieto RJA, Cuca SLE. Zanthoxylum genus as potential source of bioactive compounds. Bioact Compd Phytomed. 2012 ;10:185–218.
Fogang HP, Tapondjou LA, Womeni HM, Quassinti L, Bramucci M, Vitali LA, et al. Characterization and biological activity of essential oils from fruits of Zanthoxylum zanthoxyloides Lam. and Z. leprieurii Guill & Per., two culinary plants from Cameroon. Flavour Fragr J. 2012; 27:171-179.
Queiroz EF, Hay AE, Chaaib F, Van Diemen D, Dialla D, Hostettmann K. New and bioactive aromatic compounds from Zanthoxylum zanthoxyloides. Plant Med. 2006; 72:746-750.