In Silico Analysis of Phenolic Compounds from Ceriops decandra Griff. Leaves and Molecular Interaction as Anti Diabetes
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Keywords:
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Ceriops sp., in Silico, α-amylase, Flavonoid, Phenolic Compound, α-Glucosidase
Abstract
α-amylase and α-glucosidase in the gastrointestinal tract have an important role in the hydrolysis α-1,4 and α-1,6 glycosidic chain of starch, respectively. Inhibition of both enzyme activities becomes one of the strategies to control diabetes. However, commercial drugs such as antidiabetics have adverse effects such as gastrointestinal problems. Therefore, exploring functional food, especially from marine natural products as antidiabetic agents, is potential. In particular, Ceriops sp. was reported to contain bioactive compounds with antidiabetic properties, but its mechanism to treat diabetes has not been proved. The potency of phenolic compounds of C. decandra leaves as α-amylase and α-glucosidase inhibitors were examined in this research by implementing the molecular docking analysis in silico. Three steps of analysis were carried out in this study, including extraction from C. decandra leaves with different polarity solvents, identification of phenolic compounds using LC-HRMS, and molecular docking analysis of phenolic compounds identified from C. decandra leaves. This study revealed that quercetin, rutin, epicatechin, isorhamnetin, caffeic acid, and ferulic acid were identified from C. decandra leaves. According to the drug-likeness and toxicity analysis, the presented compounds in C. decandra leaves had high potential pharmacological properties. Furthermore, molecular interaction analysis exhibited phenolic compounds extracted with ethyl acetate, such as quercetin and epicatechin, and with methanolic extracts, such as quercetin, rutin, epicatechin, and isorhamnetin, were more effective as α-amylase and α-glucosidase inhibitors than from caffeic acid and ferulic acid. Among the phenolic compounds of C. decandra leaves, rutin and quercetin were predicted to be the potential α-glucosidase inhibitors.
References
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Lauritano, C. and A. Ianora (2016). Marine Organisms with Anti-diabetes Properties. Marine Drugs, 14(12); 1–14
Lawag, I. L., A. M. Aguinaldo, S. Naheed, and M. Mosihuzzaman (2012). α-Glucosidase Inhibitory Activity of Selected Philippine Plants. Journal of Ethnopharmacology, 144(1); 217–219
Lipinski, C. A., F. Lombardo, B. W. Dominy, and P. J. Feeney (1997). Experimental and Computational Approaches to Estimate Solubility and Permeability in Drug Discovery and Development Settings. Advanced Drug Delivery Reviews, 23(1-3); 3–25
Mahmud, I., N. Shahria, S. Yeasmin, A. Iqbal, E. H. Mukul, S. Gain, J. A. Shilpi, and M. K. Islam (2018). Ethnomedicinal, Phytochemical and Pharmacological Profile of A Mangrove Plant Ceriops Decandra Griffdin Hou. Journal of Complementary and Integrative Medicine, 16(1); 20170129
Mahmud, M. (2011). Vegetasi Mangrove Sebagai Bahan Makanan Pada Empat Suku Di Papua Mangrove Vegetation as Foods Amongst Ethnics in Papua. Biota: Jurnal Ilmiah Ilmu-Ilmu Hayati, 16(1); 88–94 (in Indonesia)
Martinez-Gonzalez, A. I., Á. Díaz-Sánchez, L. De La Rosa, I. Bustos Jaimes, and E. Alvarez Parrilla (2019). Inhibition of α-amylase by Flavonoids: Structure Activity Relationship (SAR). Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 206; 437–447
Nahoum, V., G. Roux, V. Anton, P. RougÉ, A. Puigserver, H. Bischoff, B. Henrissat, and F. Payan (2000). Crystal Structures of Human Pancreatic α-amylase in Complex with Carbohydrate and Proteinaceous Inhibitors. Biochemical Journal, 346(1); 201–208
Nipun, T. S., A. Khatib, Z. Ibrahim, Q. U. Ahmed, I. E. Redzwan, M. Z. Saiman, F. Supandi, R. Primaharinastiti, and H. R. El Seedi (2020). Characterization of α-glucosidase Inhibitors from Psychotria Malayana Jack Leaves Extract Using LC-MS-based Multivariate Data Analysis and in silico Molecular Docking. Molecules, 25(24); 5885
Prabowo, R. E. (2018). Peluang Bisnis Kuliner Buah Mangrove (Culinary Business Opportunities of Mangrove Fruit). Prosiding Seminar Nasional Multidisiplin Ilmu, 7; 978–979 (in Indonesia)
Proença, C., M. Freitas, D. Ribeiro, S. M. Tomé, E. F. Oliveira, M. F. Viegas, A. N. Araújo, M. J. Ramos, A. M. Silva, P. A. Fernandes, et al. (2019). Evaluation of A Flavonoids Library for Inhibition of Pancreatic α-amylase Towards A Structure–activity Relationship. Journal of Enzyme Inhibition and Medicinal Chemistry, 34(1); 577–588
Proença, C., D. Ribeiro, M. Freitas, and E. Fernandes (2022). Flavonoids as Potential Agents in the Management of Type 2 Diabetes Through the Modulation of α-amylase and α-glucosidase Activity: A Review. Critical Reviews in Food Science and Nutrition, 62(12); 3137–3207
Ramadhan, R., P. Phuwapraisirisan, I. Kusuma, and R. Amirta (2020). Ethnopharmacological Evaluation of Selected East Kalimantan Flora For Diabetes Therapy: The Isolation of Lupane Triterpenoids as α-glucosidase Inhibitors From Ceriops Tagal (perr) (PERR) C.B.ROBB. Rasayan Journal of Chemistry, 13(3); 1727–1734
Riyaphan, J., D. C. Pham, M. K. Leong, and C. F. Weng (2021). In Silico Approaches to Identify Polyphenol Compounds As α-glucosidase and α-amylase Inhibitors Against Type-II Diabetes. Biomolecules, 11(12); 1877
Sadeghi, M., M. Moradi, H. Madanchi, and B. Johari (2021). In Silico Study of Garlic (Allium sativum L.) Derived Compounds Molecular Interactions with α-glucosidase. In Silico Pharmacology, 9; 1–8
Sivakumar, K., S. Kannappan, B. Vijayakumar, K. P. Jithendran, S. Balasubramaniam, and A. Panigrahi (2021). Molecular Docking Study of Bio-inhibitors Extracted From Marine Macro-alga Ulva Fasciata Against Hemolysin Protein of Luminescence Disease-causing Vibrio Harveyi. Archives of Microbiology, 203(7); 4243–4258
Şöhretoğlu, D. and S. Sari (2020). Flavonoids as Alpha-glucosidase Inhibitors: Mechanistic Approaches Merged with Enzyme Kinetics and Molecular Modelling. Phytochemistry Reviews, 19(5); 1081–1092
Tian, S., J. Wang, Y. Li, D. Li, L. Xu, and T. Hou (2015). The Application of in Silico Drug-likeness Predictions in Pharmaceutical Research. Advanced Drug Delivery Reviews, 86; 2–10
Trinh, B. T., D. Staerk, and A. K. Jäger (2016). Screening for Potential α-glucosidase and α-amylase Inhibitory Constituents from Selected Vietnamese Plants Used to Treat Type 2 Diabetes. Journal of Ethnopharmacology, 186; 189–195
Trott, O. and A. J. Olson (2010). AutoDock Vina: Improving the Speed and Accuracy of Docking with A New Scoring Function, Efficient Optimization, and Multithreading. Journal of Computational Chemistry, 31(2); 455–461
Udrea, A. M., G. G. Pircalabioru, A. A. Boboc, C. Mares, A. Dinache, M. Mernea, and S. Avram (2021). Advanced Bioinformatics Tools in the Pharmacokinetic Profiles of Natural and Synthetic Compounds with Anti-diabetic Activity. Biomolecules, 11(11); 1692
Yamamoto, K., H. Miyake, M. Kusunoki, and S. Osaki (2010). Crystal Structures of Isomaltase From Saccharomyces Cerevisiae and in Complex with its Competitive Inhibitor Maltose. The FEBS journal, 277(20); 4205–4214
Zeng, L., H. Ding, X. Hu, G. Zhang, and D. Gong (2019). Galangin Inhibits α-glucosidase Activity and Formation of Non-enzymatic Glycation Products. Food Chemistry, 271; 70–79
Zhang, B. W., X. Li, W. L. Sun, Y. Xing, Z. L. Xiu, C. L. Zhuang, and Y. S. Dong (2017). Dietary Flavonoids and Acarbose Synergistically Inhibit α-glucosidaseand Lower Postprandial Blood Glucose. Journal of Agricultural and Food Chemistry, 65(38); 8319–8330
Alamsjah, M. A. and M. FauzulImron (2021). Monitoring of Diversity, Characteristics, Threatening Rate and Potency of Mangrove Vegetation in Denpasar, Bali, Indonesia. Plant Archives, 21(1); 592–599
Askama, S., S. Wahyuni, and M. Mashuni (2017). Pengaruh Penambahan Bubuk Daun Tanaman Mangrove (Ceriops sp.) Terhadap Karakteristik Organoleptik Produk Cokelat Batang (Effect of The Addition of Mangrove Plant (Ceriops sp.) Leaf on The Organoleptic Characteristics of Chocolate Bars). Jurnal Sains Dan Teknologi Pangan, 2(4); 729–735 (in Indonesia)
Banerjee, P., F. O. Dehnbostel, and R. Preissner (2018a). Prediction is a Balancing act: Importance of Sampling Methods to Balance Sensitivity and Specificity of Predictive Models Based on Imbalanced Chemical Data Sets. Frontiers in Chemistry, 1(11); 1–11
Banerjee, P., A. O. Eckert, A. K. Schrey, and R. Preissner (2018b). ProTox-II: a Webserver for the Prediction of Toxicity of Chemicals. Nucleic Acids Research, 46(W1); 257–263
Bibi, S. N., M. M. Fawzi, Z. Gokhan, J. Rajesh, N. Nadeem, R. K. RR, A. RDDG, and S. K. Pandian (2019). Ethnopharmacology, Phytochemistry, and Global Distribution Of Mangroves-a Comprehensive Review. Marine Drugs, 17(4); 1–82
Bischoff, H. (1994). Pharmacology of Alpha-glucosidase Inhibition. European Journal of Clinical Investigation, 24; 3–10
Canusa, B. S., I. L. Lawag, O. B. Villaflores, V. D. Wagh, M. Korinek, Y.-H. Tsai, F.-R. Chang, and A. M. Aguinaldo (2021). α-Glucosidase Inhibitors from the Bark Extract of Ethno-Antidiabetic Ceriops tagal (Perr.) CB Rob. Philippine Journal of Science, 151(S1); 25–60
Casacchia, T., M. A. Occhiuzzi, F. Grande, B. Rizzuti, M. C. Granieri, C. Rocca, A. Gattuso, A. Garofalo, T. Angelone, and G. Statti (2019). A Pilot Study on the Nutraceutical Properties of the Citrus hybrid Tacle® as a Dietary Source of Polyphenols for Supplementation in Metabolic Disorders. Journal of Functional Foods, 52; 370–381
Chen, L. and Y. H. Kang (2013). In Vitro Inhibitory Effect of Oriental Melon (Cucumis melo L. Var. Makuwa Makino) Seed on Key Enzyme Linked to Type 2 Diabetes: Assessment of Anti-diabetic Potential of Functional Food. Journal of Functional Foods, 5(2); 981–986
Derosa, G. and P. Maffioli (2012). α-Glucosidase Inhibitors and Their Use in Clinical Practice. Archives of Medical Science: AMS, 8(5); 899–906
Dham, S. V. H. S. . B. M. A., S. (2006). The Role of Complementary and Alternative Medicine In Regenerative Medicine. Current Diabetes Reports, 6(3); 251–258
Drwal, M. N., P. Banerjee, M. Dunkel, M. R. Wettig, and R. Preissner (2014). ProTox: a Web Server for the in Silico Prediction of Rodent Oral Toxicity. Nucleic Acids Research, 42(W1); 53–58
Hardoko, H., Y. E. Puspitasari, and E. Suprayitno (2015). α-Glucosidase Inhibitory Activities of Rhizophora Mucronata Fruitpowder. International Journal of ChemTech Research, 8(1); 211–215
Hardoko, H., B. B. Sasmito, and Y. E. Puspitasari (2016). Antidiabetic and Antioxidant Activities of Tannin Extract of Rhizophora Mucronata Leaves. Journal of Chemical and Pharmaceutical Research, 8(3); 143–148
Hardoko, H., B. B. Sasmito, and Y. E. Puspitasari (2017). Tannin Extract Characterization of Young Mangrove Rhizophora Mucronata Leaves as Ingredients for Diabetic Functional Food. Asian Journal of Microbiology, Biotechnology and Environmental Sciences, 19(2); 331–336
Jadhav, B. (2019). Phytochemical Composition, In Vitro Studies On A-Amylase And A-Glucosidase Inhibitory Activity Of Selected Mangrove Plants. International Journal of Pharmaceutical Sciences and Drug Research, 11(5); 181–186
Kharroubi, A. T. and H. M. Darwish (2015). Diabetes Mellitus: The Epidemic of the Century. World Journal of Diabetes, 6(6); 850–867
Kim, Y., J. B. Keogh, and P. M. Clifton (2016). Polyphenols and Glycemic Control. Nutrients, 8(1); 1–27
Lauritano, C. and A. Ianora (2016). Marine Organisms with Anti-diabetes Properties. Marine Drugs, 14(12); 1–14
Lawag, I. L., A. M. Aguinaldo, S. Naheed, and M. Mosihuzzaman (2012). α-Glucosidase Inhibitory Activity of Selected Philippine Plants. Journal of Ethnopharmacology, 144(1); 217–219
Lipinski, C. A., F. Lombardo, B. W. Dominy, and P. J. Feeney (1997). Experimental and Computational Approaches to Estimate Solubility and Permeability in Drug Discovery and Development Settings. Advanced Drug Delivery Reviews, 23(1-3); 3–25
Mahmud, I., N. Shahria, S. Yeasmin, A. Iqbal, E. H. Mukul, S. Gain, J. A. Shilpi, and M. K. Islam (2018). Ethnomedicinal, Phytochemical and Pharmacological Profile of A Mangrove Plant Ceriops Decandra Griffdin Hou. Journal of Complementary and Integrative Medicine, 16(1); 20170129
Mahmud, M. (2011). Vegetasi Mangrove Sebagai Bahan Makanan Pada Empat Suku Di Papua Mangrove Vegetation as Foods Amongst Ethnics in Papua. Biota: Jurnal Ilmiah Ilmu-Ilmu Hayati, 16(1); 88–94 (in Indonesia)
Martinez-Gonzalez, A. I., Á. Díaz-Sánchez, L. De La Rosa, I. Bustos Jaimes, and E. Alvarez Parrilla (2019). Inhibition of α-amylase by Flavonoids: Structure Activity Relationship (SAR). Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 206; 437–447
Nahoum, V., G. Roux, V. Anton, P. RougÉ, A. Puigserver, H. Bischoff, B. Henrissat, and F. Payan (2000). Crystal Structures of Human Pancreatic α-amylase in Complex with Carbohydrate and Proteinaceous Inhibitors. Biochemical Journal, 346(1); 201–208
Nipun, T. S., A. Khatib, Z. Ibrahim, Q. U. Ahmed, I. E. Redzwan, M. Z. Saiman, F. Supandi, R. Primaharinastiti, and H. R. El Seedi (2020). Characterization of α-glucosidase Inhibitors from Psychotria Malayana Jack Leaves Extract Using LC-MS-based Multivariate Data Analysis and in silico Molecular Docking. Molecules, 25(24); 5885
Prabowo, R. E. (2018). Peluang Bisnis Kuliner Buah Mangrove (Culinary Business Opportunities of Mangrove Fruit). Prosiding Seminar Nasional Multidisiplin Ilmu, 7; 978–979 (in Indonesia)
Proença, C., M. Freitas, D. Ribeiro, S. M. Tomé, E. F. Oliveira, M. F. Viegas, A. N. Araújo, M. J. Ramos, A. M. Silva, P. A. Fernandes, et al. (2019). Evaluation of A Flavonoids Library for Inhibition of Pancreatic α-amylase Towards A Structure–activity Relationship. Journal of Enzyme Inhibition and Medicinal Chemistry, 34(1); 577–588
Proença, C., D. Ribeiro, M. Freitas, and E. Fernandes (2022). Flavonoids as Potential Agents in the Management of Type 2 Diabetes Through the Modulation of α-amylase and α-glucosidase Activity: A Review. Critical Reviews in Food Science and Nutrition, 62(12); 3137–3207
Ramadhan, R., P. Phuwapraisirisan, I. Kusuma, and R. Amirta (2020). Ethnopharmacological Evaluation of Selected East Kalimantan Flora For Diabetes Therapy: The Isolation of Lupane Triterpenoids as α-glucosidase Inhibitors From Ceriops Tagal (perr) (PERR) C.B.ROBB. Rasayan Journal of Chemistry, 13(3); 1727–1734
Riyaphan, J., D. C. Pham, M. K. Leong, and C. F. Weng (2021). In Silico Approaches to Identify Polyphenol Compounds As α-glucosidase and α-amylase Inhibitors Against Type-II Diabetes. Biomolecules, 11(12); 1877
Sadeghi, M., M. Moradi, H. Madanchi, and B. Johari (2021). In Silico Study of Garlic (Allium sativum L.) Derived Compounds Molecular Interactions with α-glucosidase. In Silico Pharmacology, 9; 1–8
Sivakumar, K., S. Kannappan, B. Vijayakumar, K. P. Jithendran, S. Balasubramaniam, and A. Panigrahi (2021). Molecular Docking Study of Bio-inhibitors Extracted From Marine Macro-alga Ulva Fasciata Against Hemolysin Protein of Luminescence Disease-causing Vibrio Harveyi. Archives of Microbiology, 203(7); 4243–4258
Şöhretoğlu, D. and S. Sari (2020). Flavonoids as Alpha-glucosidase Inhibitors: Mechanistic Approaches Merged with Enzyme Kinetics and Molecular Modelling. Phytochemistry Reviews, 19(5); 1081–1092
Tian, S., J. Wang, Y. Li, D. Li, L. Xu, and T. Hou (2015). The Application of in Silico Drug-likeness Predictions in Pharmaceutical Research. Advanced Drug Delivery Reviews, 86; 2–10
Trinh, B. T., D. Staerk, and A. K. Jäger (2016). Screening for Potential α-glucosidase and α-amylase Inhibitory Constituents from Selected Vietnamese Plants Used to Treat Type 2 Diabetes. Journal of Ethnopharmacology, 186; 189–195
Trott, O. and A. J. Olson (2010). AutoDock Vina: Improving the Speed and Accuracy of Docking with A New Scoring Function, Efficient Optimization, and Multithreading. Journal of Computational Chemistry, 31(2); 455–461
Udrea, A. M., G. G. Pircalabioru, A. A. Boboc, C. Mares, A. Dinache, M. Mernea, and S. Avram (2021). Advanced Bioinformatics Tools in the Pharmacokinetic Profiles of Natural and Synthetic Compounds with Anti-diabetic Activity. Biomolecules, 11(11); 1692
Yamamoto, K., H. Miyake, M. Kusunoki, and S. Osaki (2010). Crystal Structures of Isomaltase From Saccharomyces Cerevisiae and in Complex with its Competitive Inhibitor Maltose. The FEBS journal, 277(20); 4205–4214
Zeng, L., H. Ding, X. Hu, G. Zhang, and D. Gong (2019). Galangin Inhibits α-glucosidase Activity and Formation of Non-enzymatic Glycation Products. Food Chemistry, 271; 70–79
Zhang, B. W., X. Li, W. L. Sun, Y. Xing, Z. L. Xiu, C. L. Zhuang, and Y. S. Dong (2017). Dietary Flavonoids and Acarbose Synergistically Inhibit α-glucosidaseand Lower Postprandial Blood Glucose. Journal of Agricultural and Food Chemistry, 65(38); 8319–8330
Authors
Puspitasari, Y. E. ., Alfikri, M. A. ., Sitanggang, R., Tambunan, J. E., & Hardoko, H. (2023). In Silico Analysis of Phenolic Compounds from Ceriops decandra Griff. Leaves and Molecular Interaction as Anti Diabetes. Science and Technology Indonesia, 8(4), 542–553. https://doi.org/10.26554/sti.2023.8.4.542-553
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