Simplified isolation method of mangiferin from Mangifera indica L. leaves and evaluation of tyrosinase inhibitory activity
Main Article Content
Abstract
A method of the isolation of mangiferin from mango (Mangifera indica L) leaves using a modification of Pressured Liquid Extraction (PLE), fractionation liquid-liquid partition (ethyl acetate and n-butanol), and recrystallization was applied in this investigation. Additionally, melting point, infrared (IR) spectroscopy, ultraviolet-visible spectroscopy (UV-Vis), and 1H and 13C nuclear magnetic resonance (NMR) spectroscopy were used to validate the chemical structure of mangiferin. Tyrosinase inhibitory activity of mango leaf extracts were then compared to that of kojic acid. Mangiferin effectively inhibited tyrosinase enzyme (inhibitory concentration (IC50) = 195.50±1.40µg/mL). It was also observed that n-hexane and ethyl acetate extracts have tyrosinase inhibitory activity (IC50= 210.07±1.37µg/mL and IC50= 436.79±0.89µg/mL), respectively. These findings are important preliminary studies for further exploration of both mangiferin and the extract to develop pharmaceutical formulations of this potent tyrosinase inhibitor.
Article Details
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
References
Rodríguez J, Di Pierro D, Gioia M, et al. Effects of a natural extract from Mangifera indica L, and its active compound, mangiferin, on energy state and lipid peroxidation of red blood cells. Biochim Biophys Acta 2006; 1760: 1333–1342.
Maisuthisakul P, Gordon MH. Antioxidant and tyrosinase inhibitory activity of mango seed kernel by product. Food Chem 2009; 117: 332–341.
Rawdkuen S, Sai-Ut S, Benjakul S. Optimizing the Tyrosinase Inhibitory and Antioxidant Activity of Mango Seed Kernels with a Response Surface Methodology. Food Anal Methods 2016; 9: 3032–3043.
Ling LT, Yap S-A, Radhakrishnan AK, et al. Standardised mangifera indica extract is an ideal antioxidant. Food Chem 2009; 113: 1154–1159.
Hostettmann K, Wagner H. Xanthone glycosides. Phytochemistry 1977; 16: 821–829.
Rocha Ribeiro S, Queiroz J, Lopes Ribeiro de Queiroz M, et al. Antioxidant in mango (Mangifera indica L.) pulp. Plant Foods Hum Nutr 2007; 62: 13–17.
Saleem M, Tanvir M, Akhtar MF, et al. Antidiabetic Potential of Mangifera indica L. cv. Anwar Ratol Leaves: Medicinal Application of Food Wastes. Medicina (B Aires); 55. Epub ahead of print 2019. DOI: 10.3390/MEDICINA55070353.
Rivera D, Balmaseda I, León A, et al. Anti-allergic properties of Mangifera indica L. extract (Vimang) and contribution of its glucosylxanthone mangiferin. J Pharm Pharmacol 2006; 58: 385–392.
Pardo-Andreu G, Barrios M, Curti C, et al. Protective effects of Mangifera indica L extract (Vimang), and its major component mangiferin, on iron-induced oxidative damage to rat serum and liver. Pharmacol Res 2008; 57: 79–86.
Shah KA, Patel MB, Patel RJ, et al. Mangifera Indica (Mango). Pharmacogn Rev 2010; 4: 42.
Ediriweera MK, Tennekoon KH, Samarakoon SR. A Review on Ethnopharmacological Applications, Pharmacological Activities, and Bioactive Compounds of Mangifera indica (Mango). Evidence-based Complement Altern Med; 2017. Epub ahead of print 2017. DOI: 10.1155/2017/6949835.
Ybañez-Julca RO, Asunción-Alvarez D, Quispe-Díaz IM, et al. Metabolomic Profiling of Mango (Mangifera indica Linn) Leaf Extract and Its Intestinal Protective Effect and Antioxidant Activity in Different Biological Models. Mol 2020, Vol 25, Page 5149 2020; 25: 5149.
Kanwal Q, Hussain I, Siddiqui HL, et al. Antifungal activity of flavonoids isolated from mango (Mangifera indica L.) leaves. http://dx.doi.org/101080/147864192010488628 2010; 24: 1907–1914.
Singh SK, Tiwari RM, Sinha SK, et al. Antimicrobial evaluation of mangiferin and its synthesized analogues. Asian Pac J Trop Biomed 2012; 2: S884–S887.
Morozkina SN, Nhung Vu TH, Generalova YE, et al. Mangiferin as new potential anti-cancer agent and mangiferin-integrated polymer systems-a novel research direction. Biomolecules 2021; 11: 1–27.
Zou T-B, Xia E-Q, He T-P, et al. Ultrasound-Assisted Extraction of Mangiferin from Mango (Mangifera indica L.) Leaves Using Response Surface Methodology. Molecules 2014; 19: 1411.
Kulkarni VM, Rathod VK. Extraction of mangiferin from Mangifera indica leaves using three phase partitioning coupled with ultrasound. Ind Crops Prod 2014; 52: 292–297.
Prado IM, Prado GHC, Prado JM, et al. Supercritical CO2 and low-pressure solvent extraction of mango (Mangifera indica) leaves: Global yield, extraction kinetics, chemical composition and cost of manufacturing. Food Bioprod Process 2013; 91: 656–664.
Vo THT, Nguyen TD, Nguyen QH, et al. EXTRACTION OF MANGIFERIN FROM THE LEAVES OF THE MANGO TREE MANGIFERA INDICA AND EVALUATION OF ITS BIOLOGICAL ACTIVITY IN TERMS OF BLOCKADE OF a-GLUCOSIDASE. 2017; 51: 44–48.
Brenner M, Hearing V. The protective role of melanin against UV damage in human skin. Photochem Photobiol 2008; 84: 539–549.
Videira IF dos S, Moura DFL, Magina S. Mechanisms regulating melanogenesis. An Bras Dermatol 2013; 88: 76.
Chang T-S. An Updated Review of Tyrosinase Inhibitors. Int J Mol Sci 2009, Vol 10, Pages 2440-2475 2009; 10: 2440–2475.
Burnett C, Bergfeld W, Belsito D, et al. Final report of the safety assessment of Kojic acid as used in cosmetics. Int J Toxicol; 29. Epub ahead of print November 2010. DOI: 10.1177/1091581810385956.
McGregor D. Hydroquinone: An Evaluation of the Human Risks from its Carcinogenic and Mutagenic Properties. http://dx.doi.org/101080/10408440701638970 2008; 37: 887–914.
Zhang Q-W, Lin L-G, Ye W-C. Techniques for extraction and isolation of natural products: a comprehensive review. Chinese Med 2018 131 2018; 13: 1–26.
Momtaz S, Mapunya B, Houghton P, et al. Tyrosinase inhibition by extracts and constituents of Sideroxylon inerme L. stem bark, used in South Africa for skin lightening. J Ethnopharmacol 2008; 119: 507–512.
Faizi S, Zikr-Ur-Rehman S, Ali M, et al. Temperature and solvent dependent NMR studies on mangiferin and complete NMR spectral assignments of its acyl and methyl derivatives. Magn Reson Chem 2006; 44: 838–844.
Lin YS, Chen HJ, Huang JP, et al. Kinetics of tyrosinase inhibitory activity using vitis vinifera leaf extracts. Biomed Res Int; 2017. Epub ahead of print 2017. DOI: 10.1155/2017/5232680.
Wu L, Chen C, Cheng C, et al. Evaluation of Tyrosinase Inhibitory, Antioxidant, Antimicrobial, and Antiaging Activities of Magnolia officinalis Extracts after Aspergillus Niger Fermentation. Biomed Res Int; 2018. Epub ahead of print 2018. DOI: 10.1155/2018/5201786.
Lim YP, Pang SF, Yusoff MM, et al. Correlation between the extraction yield of mangiferin to the antioxidant activity, total phenolic and total flavonoid content of Phaleria macrocarpa fruits. J Appl Res Med Aromat Plants 2019; 14: 100224.
Zengin G, Uysal S, Ceylan R, et al. Phenolic constituent, antioxidative and tyrosinase inhibitory activity of Ornithogalum narbonense L. from Turkey: A phytochemical study. Ind Crops Prod 2015; 70: 1–6.
Shi F, Xie L, Lin Q, Tong C, Fu Q, Xu J, Xiao J, Shi S. Profiling of tyrosinase inhibitors in mango leaves for a sustainable agro-industry. Food Chem. 2020;312:126042.
Diyana NA, Koh SP, Aziz N., Hamid NSA, Abdullah R, Puteh F, Sarah S. Assessment of Anti-Tyrosinase, Anti-Elastase and Anti-Acetylcholinesterase Properties of Fermented Mango Leaves at Different Maturity Level. Sains Malaysiana 2021;50(9): 2675-2685