HPLC-UV Standard Phenolic Constituents of African Bush Mango (Irvingia gabonensis) and Molecular Docking on Polyphenol Oxidases

Main Article Content

Catherine Joke Adeseko
David Morakinyo Sanni
Sule Ola Salawu
Ige Joseph Kade
Toluwase Hezekiah Fatoki

Abstract

Introduction: Irvingia gabonensis belongs to the Irvingiaceae plant family and commonly known as the African bush mango, wild mango, Dika nut and Manguier sauvage. The fruits of I. gabonensis are edible and their use in traditional medicine has been reported for the treatment of diabetes, diarrhea, wound ulcer, hepatic disorder, microbial infections, and inflammatory pains. 

Aim: This study aimed to identify the standard phenolic contents of I. gabonensis fruit pulp and peel extracts and investigate the bind energy on polyphenol oxidase in order to know why browning of I. gabonensis fruit is often rapidly occur and how to prevent it with suitable inhibitor in an industrial processing.

Results: The phenolics that were identified include ellagic acid, cinnamic acid, gallic acid, 3-friedelanone, lupeol, kaempferol, quercetin, alpha-curcumene and zingiberene. The two PPO from Solanum lycopersicum (PDB ID: 6HQI) and Mangifera indica (PDB: D2XZ13_model) have different binding energies across the ligands with highest score by 3-friedelanone (-14.3 and -16.1 kcal/mol respectively), followed by lupeol (-13.9 and -14.6 kcal/mol respectively). The differences in the binding energies across the plant PPOs could be due to variation in the amino acid composition and more importantly the amino acid residues that participate in the catalytic and allosteric activities

Conclusion: This study has shown the reason behind rapid browning that usually occur in I. gabonensis and more importantly, the need for effective edible inhibitors of PPO.

Keywords:
Irvingia gabonensis, African bush mango, HPLC-UV, phenolic constituents, molecular docking

Article Details

How to Cite
Adeseko, C. J., Sanni, D., Salawu, S., Kade, I., & Fatoki, T. (2019). HPLC-UV Standard Phenolic Constituents of African Bush Mango (Irvingia gabonensis) and Molecular Docking on Polyphenol Oxidases. Journal of Applied Life Sciences International, 22(1), 1-11. https://doi.org/10.9734/jalsi/2019/v22i130119
Section
Original Research Article

References

Ayuk ET, Duguma B, Franzel S, Kenque J, Mollet M, Tiki-Manga T, Zenkenga P. Uses, management and economic potential of Irvingia gabonensis in the humid lowlands of Cameroon. Forest Ecology and Management. 1999;113(1):1-9.

Kuete V, Wabo GF, Ngameni B, Mbaveng AT, Metuno R, Etoa FX, Ngadjui BT, Beng VP, Meyer JJ, Lall N. Antimicrobial activity of the methanolic extract, fractions and compounds from the stem bark of Irvingia gabonensis (Ixonanthaceae). Journal of Ethnopharmacology. 2007;114:54−60.

Adamson I, Okafor C, Abu-Bakare A. A supplement of Dikanut (Irvingia gabonesis) improves treatment of type II diabetics. West African Journal of Medicine. 1990;9: 108–115.

Okolo CO, Johnson PB, Abdurahman EM, Abdu-Aguye I, Hussaini IM. Analgesic effect of Irvingia gabonensis stem bark extract. Journal of Ethnopharmacology. 1995;45:125−129.

Ozolua RI, Eriyamremu GE, Okene EO, Ochei U. Hypoglycaemic effects of viscous preparation of Irvingia gabonensis (Dikanut) seeds in streptozotocin-induced diabetic Wistar rats. Journal of Herbs, Spices and Medicinal Plants. 2006;12:1-9.

Ngondi JL, Etoundi BC, Nyangono CB, Mbofung CM, Oben JE. IGOB131, a novel seed extract of the West African plant Irvingia gabonensis, significantly reduces body weight and improves metabolic parameters in overweight humans in a randomized double-blind placebo-controlled investigation. Lipids Health and Diseases. 2009; 8:7.
DOI: 10.1186/1476-511X-8-7

Donfack JH, Fosto GW, Ngameni B, Tsofack FN, Tchoukoua A, Ambassa P, Abia W, Tchana AN, Giardina S, Buonocore D, Finzi, PV, Vidari G, Marzatico F, Ngadjui BT, Moundipa PF. In vitro hepatoprotective and antioxidant activities of the crude extract and isolated compounds from Irvingia gabonensis. Asian Journal of Traditional Medicines. 2010;5:79−88.

Awah FM, Uzoegwu PN, Ifeonu P, Oyugi JO, Rutherford J, Yao X, Fehrmann F, Fowke KR, Eze MO. Free radical scavenging activity, phenolic contents and cytotoxicity of selected Nigerian medicinal plants. Food Chemistry. 2012;131:1279–1286.

Sun J, Chen P. Ultra-high-performance liquid chromatography with high-resolution mass spectrometry analysis of African mango (Irvingia gabonensis) seeds, extract and related dietary supplements. Journal of Agriculture and Food Chemistry. 2012; 60:8703−8709.

Macheix J, Fleuriet A, Billot J. Phenolic compounds in fruit processing. In Fruit Phenolics, (J. Macheix, A. Fleuriet and J. Billot, eds.). CRC Press, Boca Raton, Florida. 1990;239-312.

Bravo K, Osorio E. Characterization of polyphenol oxidase from cape gooseberry (Physalis peruviana L.) fruit. Food Chemistry. 2016;197:185–190.
DOI: 10.1016/j.foodchem.2015.10.126

Rolff M, Schottenheim J, Decker H, Tuczek F. Copper-O2 reactivity of tyrosinase models towards external monophenolic substrates: Molecular mechanism and comparison with the enzyme. Chemical Society Reviews. 2011;40:4077–4098.

Wuyts N, De Waele D, Swennen R. Extraction and partial characterization of polyphenol oxidase from banana (Musa acuminata Grande naine) roots. Plant Physiology and Biochemistry. 2006;44: 308–314.

Falguera V, Sánchez-Riaño A, Quintero-Cerón J, Rivera-Barrero C, Méndez-Arteaga J, Ibarz A. Characterization of polyphenol oxidase activity in juices from 12 underutilized tropical fruits with high agroindustrial potential. Food Bioprocess Technology. 2012;5:2921–2927.

Reinkensmeier A, Steinbrenner K, Homann T, Bußler S, Rohn S, Rawel HM. Monitoring the apple polyphenol oxidase-modulated adduct formation of phenolic and amino compounds. Food Chemistry. 2016;194:76–85.

Taranto F, Pasqualone A, Mangini G, Tripodi P, Miazzi MM, Pavan S, Montemurro C. Polyphenol oxidases in crops: Biochemical, physiological and genetic aspects. International Journal of Molecular Science. 2017;18:377.

Murata M, Tsurutani M, Tomita M, Homma S, Kaneko K. Relationship between apple ripening and browning: Changes in polyphenol content and polyphenol oxidase. Journal of Agriculture and Food Chemistry. 1995;43:1115–1121.

Yoruk R, Marshall MR. Physicochemical properties and function of plant polyphenol oxidase: A review. Journal of Food Biochemistry. 2003;27:361–422.

Guven GR, Guven K, Bekler FM, Acer O, Alkan H, Dogru M. Purification and characterization of polyphenol oxidase from purslane. Food Science and Techno-logy Campinas. 2017;37(3):356-362.

Lourenco EJ, Neves VA, Silva MAD. Polyphenol oxidase from sweet potato: Purification and properties. Journal of Agriculture and Food Chemistry. 1992;40: 2369–2373.

Rapeanu G, Loey VA, Smout C, Hendrickx M. Biochemical characterization and process stability of polyphenol oxidase extracted from Victoria grape (Vitis vinifera ssp. Sativa). Food Chemistry. 2006;94: 253–261.

Saeidian S. Partial purification and characterization of polyphenol oxidase from tomatoes (Solanum lycopersicum). International Journal of Advanced Biological and Biomedical Research. 2013; 1(6):637-648

Sakiroglu H, Yılmaz E, Erat M, Öztürk AE. Selected properties of polyphenol oxidase obtained from ISPIR sugar bean. Inter-national Journal of Food Properties. 2013; 16(6):1314-1321.
DOI: 10.1080/10942912.2011.584258

Chandra A, Rana J, Li Y. Separation, identification, quantification and method validation of anthocyanins in botanical supplement raw materials by HPLC and HPLC-MS. Journal of Agriculture and Food Chemistry. 2001;49:3515-3521.

Mishra BB, Gautam S. Polyphenol oxidases: Biochemical and molecular characterization, distribution, role and its control. Enzyme Engineering. 2016; 5(1):141-149.
DOI: 10.4172/2329-6674.1000141

Waterhouse A, Bertoni M, Bienert S, Studer G, Tauriello G, Gumienny R, Heer FT, de Beer TAP, Rempfer C, Bordoli L, Lepore R, Schwede T. SWISS-model: homology modelling of protein structures and complexes. Nucleic Acids Research. 2018;46(W1):W296-W303.

Camacho C, Coulouris G, Avagyan V, Ma N, Papadopoulos J, Bealer K, Madden TL. BLAST+: Architecture and applications. BMC Bioinformatics. 2009;10:421-430

Remmert M, Biegert A, Hauser A, Söding J. HHblits: Lightning-fast iterative protein sequence searching by HMM-HMM alignment. Nature Methods. 2012;9:173-175.

Kampatsikas I, Bijelic A, Pretzler M, Rompel A. A peptide-induced self-cleavage reaction initiates the activation of tyrosinase. Angewandte. Chemie Inter-national Edition. 2019;58:7475-7479.
DOI: 10.1002/anie.201901332

Sanni DM, Lawal OT, Fatoki TH, Salawu SO. In silico Phylogenetics and molecular docking studies of rhodanese from yeast. Journal of Advances in Biology and Biotechnology. 2018;17(4):1-10.

DOI: 10.9734/JABB/2018/40974

Morris GM, Huey R, Lindstrom W, Sanner MF, Belew RK, Goodsell DS, et al. Auto Dock4 and AutoDockTools4: Automated docking with selective receptor flexibility. Journal of Computational Chemistry. 2009; 30(16):2785–2791.

Trott O, Olson AJ. AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. Journal of Computational Chemistry. 2010; 31(2):455–61.

Igoli OJ, Alexander GI. Friedelanone and other triterpenoids from Hymenocardia acida. International Journal of Physical Sciences. 2008;3:156–158.

Atawodi SE. Polyphenol content and in vitro antioxidant activity of methanol extract of seeds of Irvingia gabonensis Baill. of Nigerian origin. Electronic Journal of Environmental, Agricultural and Food Chemistry. 2011;10:2314− 2321.

Terashima S, Shimizu M, Horie S, Morita N. Studies on aldose reductase inhibitors from natural products. IV. Constituents and aldose reductase inhibitory effect of Chrysanthemum morifolium, Bixa orellana and Ipomoea batatas. Chemical and Pharmaceutical Bulletin. 1991;39:3346-3347.

Cuendet M, Oteham CP, Moon RC, Pezzuto JM. Quinone reductase induction as a biomarker for cancer chemopreven-tion. Journal of Natural Products. 2006;69: 460−463.