Molecular Docking of Polyphenol Compounds from Anacardium occidentale with Alpha-Glucosidase and Dipeptidyl-Peptidase-4 Enzymes
DOI:
https://doi.org/10.11113/mjfas.v17n2.2059Keywords:
Molecular docking, Type 2 Diabetes Mellitus, Anacardium occidentale, enzymes, acarboseAbstract
Type 2 diabetes mellitus (T2DM) is a chronic disease, in which the body failed to regulate blood glucose level due to insulin resistance. This condition may lead to high glucose level, which could potentially causes many serious health problems associated with cardiovascular system, nerve, eye and kidney. In treatment of T2DM, enzymes such as alpha-glucosidase (AG) and dipeptidyl-peptidase IV (DPP-4) have become the main targets since these enzymes play important roles in controlling the blood glucose level in the human body. In this study, the computational approach using molecular docking simulation study was used to predict the interaction and binding affinity of polyphenol compounds from Anacardium occidentale (A. occidentale) towards the AG and DPP-4 enzymes. The results were analysed based on three parameters: binding energy value, hydrogen bond formation and hydrophobic interaction between the compound and the protein at the binding site. The result showed that myricetin interacted with AG with the lowest binding energy of -7.6 kcal/mol and formed only one hydrogen bond to the Asp327 residue. In contrast, acarbose the positive control, interacted with many residues such as Asp327, Asp443 and Asp542 with the binding energy of - 6.0 kcal/mol. As for DPP-4 enzyme, sitagliptin was predicted as the best binder out of 15 polyphenols with binding energy of -9.2 kcal/mol. At the DPP-4 enzyme druggable region, sitagliptin formed an interaction with Tyr547 residue. In conclusion, our result suggested alpha-glucosidase as the most promising enzyme interacted with polyphenol compounds with favourable inhibitory effect since it can interact better than the current anti-diabetic drug, acarbose.
References
Abdullah Thaidi, N. I., Mat Jusoh, H., Ghazali, A. B., Susanti, D., & Haron, N. (2019). The Effect of Bioactive Polyphenols from Anacardium occidentale Linn. Leaves on Alpha-Amylase and Dipeptidyl Peptidase IV Activities. Indonesian Journal of Chemistry.
Abdullahi, S., & Olatunji, G. A. (2010). Antidiabetic Activity of Anacardium occidentale in Alloxan – diabetic Rats. Journal of Science and Technology, 30(3), 35–39.
Agius, L. (2008). Targeting Hepatic Glucokinase in Type 2 Diabetes: Weighing the Benefits and Risks. Diabetes, 58(1), 18–20.
Aracelli, de S. L., Md., T. I., Antonio, L. G. J., Joao, M. de C. e S., Marcus, V. O. B. de A., Marcia, F. C. J. P., … Jose, A. D. L. (2016). Pharmacological properties of cashew (Anacardium occidentale). African Journal of Biotechnology, 15(35), 1855–1863.
Baig, M. H., Ahmad, K., Rabbani, G., Danishuddin, M., & Choi, I. (2018). Computer Aided Drug Design and its Application to the Development of Potential Drugs for Neurodegenerative Disorders. Current neuropharmacology, 16(6), 740–748.
Baptista, A., Gonçalves, R. V., Bressan, J., & do Carmo Gouveia Pelúzio, M. (2018). Antioxidant and Antimicrobial Activities of Crude Extracts and Fractions of Cashew (Anacardium occidentale L.), Cajui (Anacardium microcarpum), and Pequi (Caryocar brasiliense C.): A systematic Review. Oxidative Medicine and Cellular Longevity.
Berg, J. M., Tymoczko, J. L. & Stryer, L. (2002). Biochemistry: Section 1.3, Chemical Bonds in Biochemistry (5th ed). New York, NY: W H Freeman 2002.
Chotphruethipong, L., Benjakul, S., & Kijroongrojana, K. (2019). Ultrasound assisted extraction of antioxidative phenolics from cashew (Anacardium occidentale L.) leaves. Journal of Food Science and Technology.
Dias, C. C. Q., Madruga, M. S., Pintado, M. M. E., Almeida, G. H. O., Alves, A. P. V., Dantas, F. A., … Soares, J. K. B. (2019). Cashew nuts (Anacardium occidentale L.) decrease visceral fat, yet augment glucose in dyslipidemic rats. PLOS ONE, 14(12).
El-Kabbani, O., Ruiz, F., Darmanin, C., & Chung, R. P.-T. (2004). Aldose reductase structures: implications for mechanism and inhibition. Cellular and Molecular Life Sciences (CMLS), 61(7-8), 750–762.
Fikrika, H., Ambarsari, L., & Sumaryada, T. (2016). Molecular Docking Studies of Catechin and Its Derivatives as Anti-bacterial Inhibitor for Glucosamine-6-Phosphate Synthase. IOP Conference Series: Earth and Environmental Science, 31, 012009.
Hebert, L. F., Jr, Daniels, M. C., Zhou, J., Crook, E. D., Turner, R. L., Simmons, S. T., Neidigh, J. L., Zhu, J. S., Baron, A. D., & McClain, D. A. (1996). Overexpression of glutamine:fructose-6-phosphate amidotransferase in transgenic mice leads to insulin resistance. The Journal of clinical investigation, 98(4), 930–936.
Hubbard, R. E. (2010). Hydrogen Bonds in Proteins : Role and Strength, (February).
Hyun, T. K., Eom, S. H., & Kim, J. (2014). Molecular docking studies for discovery of plant- derived α -glucosidase inhibitors, 7(3), 166–170.
Kalhotra, P., Chittepu, V. C., Osorio-Revilla, G., & Gallardo-Velázquez, T. (2019). Discovery of Galangin as a Potential DPP-4 Inhibitor That Improves Insulin-Stimulated Skeletal Muscle Glucose Uptake: A Combinational Therapy for Diabetes. International journal of molecular sciences, 20(5), 1228.
Klvana, M. (2018). Re: The number and distance of H-bond formed between protein-ligand complex varies in 2 different softwares, how it is possible?.
Kondo, H., Fujimoto, K.J., Tanaka, S., Deki, H., Nakamura, T. (2015). Theoretical Prediction and Experimental Verification on Enantioselectivity of haloacid dehalogenase L-DEX YL with chloropropionate. Chemical Physics Letters.
Mohammed, A., Kumar, D., & Rizvi, S. I. (2015). Antidiabetic Potential of Some Less Commonly Used Plants in Traditional Medicinal Systems of India and Africa. Journal of Intercultural Ethnopharmacology, 4(1).
Natarajan, A., Sugumar, S., Bitragunta, S., & Balasubramanyan, N. (2015). Molecular docking studies of (4Z, 12Z)-cyclopentadeca-4, 12-dienone from Grewia hirsuta with some targets related to type 2 diabetes. BMC Complementary and Alternative Medicine, 15(1).
National Center for Biotechnology Information. PubChem Database. Phenol, CID=996
Nur Athirah Zabidi , Nur Akmal Ishak , Muhajir Hamid , Siti Efliza Ashari & Muhammad Alif Mohammad Latif (2021) Inhibitory evaluation of Curculigo latifolia on α-glucosidase, DPP (IV) and in vitro studies in antidiabetic with molecular docking relevance to type 2 diabetes mellitus. Journal of Enzyme Inhibition and Medicinal Chemistry, 36(1), 109-121.
Nurul Iilani, A. H. (2015). Affinity of dehalogenase E towards various of haloalkanoic acids. International Islamic University Malaysia, Kuantan.
Okpashi, V. E., Bayim, P. R. B., & Obi-Abang, M. (2014). Comparative Effects of Some Medicinal Plants: Anacardium occidentale, Eucalyptus globulus, Psidium guajava, and Xylopia aethiopica Extracts in Alloxan-Induced Diabetic Male Wistar Albino Rats. Biochemistry Research International.
Rizvi, S. I., & Mishra, N. (2013). Traditional Indian Medicines Used for the Management of Diabetes Mellitus. Journal of Diabetes Research.
Ross, I. A. (2001). Anacardium occidentale. Medicinal Plants of the World. Humana Press. Totowa, NJ. (2). 43-45.
Salehi, Gültekin-Özgüven, Kırkın, Özçelik, Morais-Braga, Carneiro, Bezerra, et al. (2019). Anacardium Plants: Chemical, Nutritional Composition and Biotechnological Applications. Biomolecules, 9(9), 465.
Schulze-Kaysers, N., Feuereisen, M. M., & Schieber, A. (2015). Phenolic compounds in edible species of the Anacardiaceae family – a review. RSC Advances, 5(89), 73301–73314.
Shen, W., & Lu, Y. H. (2013). Molecular docking of citrus flavonoids with some targets related to diabetes. Bangladesh Journal of Pharmacology, 8(2), 156-170.
Thallapally, P. K., & Nangia, A. (2001). A Cambridge Structural Database analysis of the C – H … Cl interaction : C – H … Cl 2 and C – H … Cl – M often behave as hydrogen bonds but C – H … Cl – C is generally a van der Waals interaction, 1–6.
Wallace, A. C., Laskowski, R. A., & Thornton, J. M. (1995). LIGPLOT : a program to generate schematic diagrams of protein-ligand interactions Clean up structure, 8(2), 127–134.
World Health Organization. (2020). Diabetes. Retrieved from https://www.who.int/news-room/fact-sheets/detail/diabetes
Yuan, H., Ma, Q., Ye, L., & Piao, G. (2016). The Traditional Medicine and Modern Medicine from Natural Products. Molecules, 21.
