Chemical composition of leaf essential oil of Schinopsis lorentzii and its inhibitory effects against key enzymes relevant to type-2 diabetes: an emphasis on GC-MS chemical profiling and molecular docking studies

References

• Kaur, R., Kaur, M., Singh, J. (2018). Endothelial dysfunction and platelet hyperactivity in type 2 diabetes mellitus: molecular insights and therapeutic strategies. Cardiovascular Diabetology. 17 (1): 1-17 doi: 10.1186/s12933-018-0763-3
   PubMedGoogle Scholar
• El-Nashar, H.A., Taleb, M., EL-Shazly, M., Zhao, C., Farag, M.A. (2024). Polysaccharides (pectin, mucilage, and fructan inulin) and their fermented products: A critical analysis of their biochemical, gut interactions, and biological functions as antidiabetic agents. Phytotherapy Research. 38(2): 662-693 doi: 10.1002/ptr.8067
   PubMed Web of Science ®Google Scholar
• Mukhtar, Y., Galalain, A., Yunusa, U. (2020). A modern overview on diabetes mellitus: a chronic endocrine disorder. European Journal of Biology. 5(2): 1-14 doi: 10.47672/ejb.409
   Google Scholar
• Chaudhury, A., Duvoor, C., Reddy Dendi, V.S., Kraleti, S., Chada, A., Ravilla, R., Marco, A., Shekhawat, N.S., Montales, M.T., Kuriakose, K., Sasapu, A., Beebe, A., Patil, N., Musham, C.K., Lohani, G.P., Mirza, W. (2017). Clinical review of antidiabetic drugs: implications for type 2 diabetes mellitus management. Front. Endocrinol. (Lausanne). 8: 6. doi: 10.3389/fendo.2017.00006
   PubMed Web of Science ®Google Scholar
• El-Nashar, H.A., Ali, A.A.M., Salem, Y.H. (2023). Genus Pimenta: an updated comprehensive review on botany, distribution, ethnopharmacology, phytochemistry and bio-logical approaches. Chemistry & Biodiversity. 20(12): e202300855 doi: 10.1002/cbdv.202300855
   PubMed Web of Science ®Google Scholar
• Derosa, G., Maffioli, P. (2012). α-Glucosidase inhibitors and their use in clinical practice. Arch. Med. Sci. 8(5): 899-906. doi: 10.5114/aoms.2012.31621
   PubMed Web of Science ®Google Scholar
• Godbout, A., Chiasson, J.L. (2007). Who should benefit from the use of alpha-glucosidase inhibitors? Curr. Diab. Rep. 7(5): 333-339 doi: 10.1007/s11892-007-0055-x
   PubMedGoogle Scholar
• Riyaphan, J., Pham, D.-C., Leong, M. K., Weng, C.-F. (2021). In Silico approaches to identify polyphenol compounds as α-glucosidase and α-amylase inhibitors against type-II diabetes. Biomolecules. 11(12): 1877 doi: 10.3390/biom11121877
   PubMed Web of Science ®Google Scholar
• Tundis, R., Loizzo, M.R., Menichini, F. (2010). Natural products as alpha-amylase and alpha-glucosidase inhibitors and their hypoglycaemic potential in the treatment of diabetes: an update. Mini Rev. Med. Chem. 10(4): 315-331. doi: 10.2174/138955710791331007
   PubMed Web of Science ®Google Scholar
• Hung, H.Y., Qian, K., Morris-Natschke, S.L., Hsu, C.S., Lee, K.H. (2012). Recent discovery of plant-derived anti-diabetic natural products. Nat. Prod. Rep. 29(5): 580-606. doi: 10.1039/c2np00074a
   PubMed Web of Science ®Google Scholar
• Ervina, M. (2020). The recent use of Swietenia mahagoni (L.) Jacq. as antidiabetes type 2 phytomedicine: A systematic review. Heliyon. 6(3): e03536 doi: 10.1016/j.heliyon.2020.e03536
   PubMed Web of Science ®Google Scholar
• Jamaddar, S., Sarkar, C., Akter, S., Mubarak, M.S., El-Nashar, H.A., El-Shazly, M., Islam, M.T. (2023). Brazilin: An updated literature-based review on its promising therapeutic approaches and toxicological studies. South African Journal of Botany. 158: 118-132 doi: 10.1016/j.sajb.2023.04.053
   Web of Science ®Google Scholar
• Tahir, H.U., Sarfraz, R.A., Ashraf, A., Adil, S. (2016). Chemical composition and antidiabetic activity of essential oils obtained from two spices (Syzygium aromaticum and Cuminum cyminum). International Journal of Food Properties. 19(10): 2156-2164 doi: 10.1080/10942912.2015.1110166
   Web of Science ®Google Scholar
• Ishaq, A.R., El-Nashar, H.A., Younis, T., Mangat, M.A., Shahzadi, M., Ul Haq, A.S., El-Shazly, M. (2022). Genus Lupinus (Fabaceae): A review of ethnobotanical, phytochemical and biological studies. Journal of Pharmacy and Pharmacology. 74(12): 1700-1717 doi: 10.1093/jpp/rgac058
   PubMed Web of Science ®Google Scholar
• Figueiredo, A.C., Barroso, J.G., Pedro, L.G., Scheffer, J.J. (2008). Factors affecting secondary metabolite production in plants: volatile components and essential oils. Flavour and Fragrance Journal. 23(4): 213-226 doi: 10.1002/ffj.1875
   Web of Science ®Google Scholar
• El-Nashar, H.A., Eldehna, W.M., Al-Rashood, S.T., Alharbi, A., Eskandrani, R.O., Aly, S.H. (2021). GC/MS Analysis of essential oil and enzyme inhibitory activities of Syzygium cumini (Pamposia) grown in Egypt: chemical characterization and molecular docking studies. Molecules. 26(22): 6984 doi: 10.3390/molecules26226984
   PubMed Web of Science ®Google Scholar
• Lammari, N., Demautis, T., Louaer, O., Meniai, A.H., Casabianca, H., Bensouici, C., Devouassoux, G., Fessi, H., Bentaher, A., Elaïssari, A. (2021). Nanocapsules containing Saussurea lappa essential oil: Formulation, characterization, antidiabetic, anti-cholinesterase and anti-inflammatory potentials. International Journal of Pharmaceutics. 593: 120138 doi: 10.1016/j.ijpharm.2020.120138
   PubMed Web of Science ®Google Scholar
• El-Nashar, H.A., Al-Azzawi, M.A., Al-Kazzaz, H.H., Alghanimi, Y.K., Kocaebli, S.M., Alhmammi, M., Asad, A., Salam, T., El-Shazly, M., Ali, M.A. (2024). HPLC-ESI/MS-MS metabolic profiling of white pitaya fruit and cytotoxic potential against cervical cancer: comparative studies, synergistic effects, and molecular mechanistic approaches. Journal of Pharmaceutical and Biomedical Analysis. 116121 doi: 10.1016/j.jpba.2024.116121
   PubMed Web of Science ®Google Scholar
• Roitman, J.N., Merrill, G.B., Beck, J.J. (2011). Survey of ex situ fruit and leaf volatiles from several Pistacia cultivars grown in California. J. Sci. Food Agric. 91(5): 934-942. doi: 10.1002/jsfa.4268
   PubMed Web of Science ®Google Scholar
• Montanari, R.M., Barbosa, L.C., Demuner, A.J., Silva, C.J., Andrade, N.J., Ismail, F.M., Barbosa, M.C. (2012). Exposure to Anacardiaceae volatile oils and their constituents induces lipid peroxidation within food-borne bacteria cells. Molecules. 17(8): 9728-9740. doi: 10.3390/molecules17089728
   PubMed Web of Science ®Google Scholar
• El-Nashar, H.A., El-Labbad, E.M., Al-Azzawi, M.A., Ashmawy, N.S. (2022). A new xanthone glycoside from Mangifera indica L.: physicochemical properties and in vitro anti-skin aging activities. Molecules. 27(9): 2609 doi: 10.3390/molecules27092609
   PubMed Web of Science ®Google Scholar
• Simionatto, E., Peres, M., Hess, S., Da Silva, C., Chagas, M., Poppi, N., Prates, C., Matos, M.d.F., Santos, E., De Carvalho, J. (2010). Chemical composition and cytotoxic activity of leaves essential oil from Mangifera indica var. coquinho (Anacardiaceae). Journal of Essential Oil Research. 22(6): 596-599 doi: 10.1080/10412905.2010.9700408
   Web of Science ®Google Scholar
• Vivanco, K., Montesinos, J.V., Cumbicus, N., Malagón, O., Gilardoni, G. (2023). The essential oil from leaves of Mauria heterophylla Kunth (Anacardiaceae): chemical and enantioselective analyses. Journal of Essential Oil Research. 35(6): 563-569 doi: 10.1080/10412905.2023.2266430
   Web of Science ®Google Scholar
• Douissa, F.B., Hayder, N., Chekir-Ghedira, L., Hammami, M., Ghedira, K., Mariotte, A.M., Dijoux-Franca, M.G. (2005). New study of the essential oil from leaves of Pistacia lentiscus L.(Anacardiaceae) from Tunisia. Flavour and Fragrance Journal. 20(4): 410-414 doi: 10.1002/ffj.1445
   Web of Science ®Google Scholar
• Basha, R.H., Sankaranarayanan, C. (2014). β-Caryophyllene, a natural sesquiterpene, modulates carbohydrate metabolism in streptozotocin-induced diabetic rats. Acta Histochemica. 116(8): 1469-1479. doi: 10.1016/j.acthis.2014.10.001
   PubMed Web of Science ®Google Scholar
• Bandaru, S.D., Balraj, M., Badrachalam, R., Mani, V. (2023). Effect of β-Caryophyllene on oxidative stress, glucose metabolism in the skeletal muscle of high fat diet and fructose-induced type-2 diabetic adult male rats. Bioinformation. 19(4): 417-422. doi: 10.6026/97320630019417
   PubMed Web of Science ®Google Scholar
• Cardullo, N., Muccilli, V., Cunsolo, V., Tringali, C. (2020). Mass spectrometry and (1)H-NMR study of Schinopsis lorentzii (Quebracho) tannins as a source of hypoglycemic and antioxidant principles. Molecules. 25(14).
   Web of Science ®Google Scholar
• Venter, P.B., Sisa, M., van der Merwe, M.J., Bonnet, S.L., van der Westhuizen, J.H. (2012). Analysis of commercial proanthocyanidins. Part 1: the chemical composition of quebracho (Schinopsis lorentzii and Schinopsis balansae) heartwood extract. Phytochemistry. 73(1): 95-105. doi: 10.1016/j.phytochem.2011.10.006
   PubMedGoogle Scholar
• Cejas, E., Pinto, S., Prosdócimo, F., Batallé, M., Barrios, H., Tellez, G., De Franceschi, M. (2011). Evaluation of quebracho red wood (Schinopsis lorentzii) polyphenolic vegetable extract for the reduction of coccidiosis in broiler chicks. International Journal of Poultry Science. 10(5): 344-349 doi: 10.3923/ijps.2011.344.349
   Google Scholar
• Elfarnini, M., Abdel-hamid, A., Achir, M., Jamaleddine, J., Blaghen, M. (2018). Volatile compounds in the skin essential oil of Moroccan Feijoa sellowiana. European Journal of Medicinal Plants. 1-7 doi: 10.9734/EJMP/2018/40817
   Google Scholar
• Todirascu-Ciornea, E., El-Nashar, H.A.S., Mostafa, N.M., Eldahshan, O.A., Boiangiu, R.S., Dumitru, G., Hritcu, L., Singab, A.N. B. (2019). Schinus terebinthifolius essential oil attenuates scopolamine-induced memory deficits via cholinergic modulation and antioxidant properties in a zebrafish model. Evid. Based Complement. Alternat. Med. 2019: 5256781. doi: 10.1155/2019/5256781
   PubMed Web of Science ®Google Scholar
• Mosbah, H., Louati, H., Boujbiha, M.A., Chahdoura, H., Snoussi, M., Flamini, G., Ascrizzi, R., Bouslema, A., Achour, L., Selmi, B. (2018). Phytochemical characterization, antioxidant, antimicrobial and pharmacological activities of Feijoa sellowiana leaves growing in Tunisia. Industrial Crops and Products. 112: 521-531. doi: 10.1016/j.indcrop.2017.12.051
   Web of Science ®Google Scholar
• El-Nashar, H.A.S., Eldehna, W.M., Al-Rashood, S.T., Alharbi, A., Eskandrani, R.O., Aly, S.H. (2021). GC/MS analysis of essential oil and enzyme inhibitory activities of Syzygium cumini (Pamposia) grown in Egypt: chemical characterization and molecular docking studies. Molecules. 26(22).
   Web of Science ®Google Scholar
• El-Nashar, H.A.S., Mostafa, N.M., El-Badry, M.A., Eldahshan, O.A., Singab, A.N.B. (2020). Chemical composition, antimicrobial and cytotoxic activities of essential oils from Schinus polygamus (Cav.) cabrera leaf and bark grown in Egypt. Nat Prod Res. 35(23): 5369-5372. doi: 10.1080/14786419.2020.1765343
   PubMed Web of Science ®Google Scholar
• Mashiach, E., Nussinov, R., Wolfson, H.J. (2010). FiberDock: Flexible induced-fit backbone refinement in molecular docking. Proteins. 78(6): 1503-1519. doi: 10.1002/prot.22668
   PubMed Web of Science ®Google Scholar
• Boehr, D.D., Nussinov, R., Wright, P.E. (2009). The role of dynamic conformational ensembles in biomolecular recognition. Nat. Chem. Biol. 5(11): 789-796. doi: 10.1038/nchembio.232
   PubMed Web of Science ®Google Scholar
• Etsassala, N., Badmus, J.A., Marnewick, J.L., Egieyeh, S., Iwuoha, E.I., Nchu, F., Hussein, A.A. (2022). Alpha-glucosidase and alpha-amylase inhibitory activities, molecular docking, and antioxidant capacities of Plectranthus ecklonii constituents. Antioxidants (Basel). 11(2).
   Google Scholar
• ul Qamar, M.T., Kiran, S., Ashfaq, U.A., Javed, M.R., Anwar, F., Ali, M.A., Gilani, A.u.H. (2016). Discovery of novel dengue NS2B/NS3 protease inhibitors using pharmacophore modeling and molecular docking based virtual screening of the zinc database. International Journal of Pharmacology. 12(6): 621-632 doi: 10.3923/ijp.2016.621.632
   Web of Science ®Google Scholar
• Ali, H., Houghton, P., Soumyanath, A. (2006). α-Amylase inhibitory activity of some Malaysian plants used to treat diabetes; with particular reference to Phyllanthus amarus. Journal of Ethnopharmacology. 107(3): 449-455 doi: 10.1016/j.jep.2006.04.004
   PubMed Web of Science ®Google Scholar
• Ahmad, Z., Zamhuri, K.F., Yaacob, A., Siong, C.H., Selvarajah, M., Ismail, A., Hakim, M. N. (2012). In vitro anti-diabetic activities and chemical analysis of polypeptide-k and oil isolated from seeds of Momordica charantia (Bitter Gourd). Molecules. 17(8): 9631-9640 doi: 10.3390/molecules17089631
   PubMed Web of Science ®Google Scholar
• Cardullo, N., Muccilli, V., Cunsolo, V., Tringali, C. (2020). Mass spectrometry and 1H-NMR study of Schinopsis lorentzii (Quebracho) tannins as a source of hypoglycemic and antioxidant principles. Molecules. 25(14): 3257 doi: 10.3390/molecules25143257
   PubMed Web of Science ®Google Scholar
• Kumawat, V.S., Kaur, G. (2020). Insulinotropic and antidiabetic effects of β-caryophyllene with l-arginine in type 2 diabetic rats. Journal of Food Biochemistry. 44(4): e13156 doi: 10.1111/jfbc.13156
   PubMed Web of Science ®Google Scholar
• Stevens, N., Allred, K. (2022). Antidiabetic potential of volatile cinnamon oil: a review and exploration of mechanisms using in silico molecular docking simulations. Molecules. 27 (3): 853 doi: 10.3390/molecules27030853
   PubMed Web of Science ®Google Scholar
• Usman, L., Oguntoye, O., Ismaeel, R. (2020). Effect of seasonal variation on chemical composition, antidiabetic and antioxidant potentials of leaf essential oil of Eucalyptus globulus L. Journal of Essential Oil Bearing Plants. 23(6): 1314-1323 doi: 10.1080/0972060X.2020.1862710
   Web of Science ®Google Scholar
• Hajlaoui, H., Arraouadi, S., Noumi, E., Aouadi, K., Adnan, M., Khan, M.A., Kadri, A., Snoussi, M. (2021). Antimicrobial, antioxidant, anti-acetylcholinesterase, antidiabetic, and pharmacokinetic properties of Carum carvi L. and Coriandrum sativum L. essential oils alone and in combination. Molecules. 26(12): 3625 doi: 10.3390/molecules26123625
   PubMed Web of Science ®Google Scholar
• Kaskoos, R.A. (2019). GC/MS Profile and in-vitro Antidiabetic Activity of Cinnamomum zeylanicum Blume., Bark and Trachyspermum ammi (L.) Sprague, Seeds. Journal of Essential Oil Bearing Plants. 22(2): 535-544 doi: 10.1080/0972060X.2019.1612281
   Web of Science ®Google Scholar
• Özbek, H., Sever, B. (2017). Anti-inflammatory and hypoglycemic activities of alpha-pinene. ACTA Pharmaceutica Sciencia. 55(4): doi: 10.23893/1307-2080.APS.05522
   Google Scholar
• Ben Lamine, J., Boujbiha, M.A., Dahane, S., Cherifa, A.B., Khlifi, A., Chahdoura, H., Yakoubi, M.T., Ferchichi, S., El Ayeb, N., Achour, L. (2019). α-Amylase and α-glucosidase inhibitor effects and pancreatic response to diabetes mellitus on Wistar rats of Ephedra alata areal part decoction with immunohistochemical analyses. Environ. Sci. Pollut. Res Int. 26(10): 9739-9754. doi: 10.1007/s11356-019-04339-3
   PubMed Web of Science ®Google Scholar
• Hiyoshi, T., Fujiwara, M., Yao, Z. (2017). Postprandial hyperglycemia and postprandial hypertriglyceridemia in type 2 diabetes. J. Biomed. Res. 33(1): 1-16. doi: 10.7555/JBR.31.20160164
   PubMed Web of Science ®Google Scholar
• Ahmed, S., Ali, M.C., Ruma, R.A., Mahmud, S., Paul, G.K., Saleh, M.A., Alshahrani, M.M., Obaidullah, A.J., Biswas, S.K., Rahman, M.M., Rahman, M.M., Islam, M.R. (2022). Molecular Docking and dynamics simulation of natural compounds from betel leaves (Piper betle L.) for investigating the potential inhibition of alpha-amylase and alpha-glucosidase of type 2 diabetes. Molecules. 27(14).
   Web of Science ®Google Scholar
• Kazeem, M.I., Adamson, J.O., Ogunwande, I.A. (2013). Modes of inhibition of α-amylase and α-glucosidase by aqueous extract of Morinda lucida Benth leaf. Biomed. Res. Int. 2013: 527570. doi: 10.1155/2013/527570
   PubMed Web of Science ®Google Scholar
• Balfour, J.A., McTavish, D. (1993). Acarbose. An update of its pharmacology and therapeutic use in diabetes mellitus. Drugs. 46(6): 1025-1054. doi: 10.2165/00003495-199346060-00007
   PubMed Web of Science ®Google Scholar
• Ademiluyi, A.O., Oboh, G. (2013). Aqueous extracts of Roselle (Hibiscus sabdariffa Linn.) varieties inhibit α-amylase and α-glucosidase activities in vitro. J. Med. Food. 16(1): 88-93. doi: 10.1089/jmf.2012.0004
   PubMed Web of Science ®Google Scholar
• Noor, Z.I., Ahmed, D., Rehman, H.M., Qamar, M.T., Froeyen, M., Ahmad, S., Mirza, M.U. (2019). In vitro antidiabetic, anti-obesity and antioxidant analysis of Ocimum basilicum aerial biomass and in silico molecular docking simulations with alpha-amylase and lipase enzymes. Biology (Basel). 8(4).
   PubMedGoogle Scholar
• Gilles, C., Astier, J.P., Marchis-Mouren, G., Cambillau, C., Payan, F. (1996). Crystal structure of pig pancreatic alpha-amylase isoenzyme II, in complex with the carbohydrate inhibitor acarbose. Eur. J. Biochem. 238(2): 561-569. doi: 10.1111/j.1432-1033.1996.0561z.x
   PubMedGoogle Scholar
• Tagami, T., Yamashita, K., Okuyama, M., Mori, H., Yao, M., Kimura, A. (2013). Molecular basis for the recognition of long-chain substrates by plant α-glucosidases. J. Biol. Chem. 288(26): 19296-19303. doi: 10.1074/jbc.M113.465211
   PubMed Web of Science ®Google Scholar
• Boström, J., Greenwood, J.R., Gottfries, J. (2003). Assessing the performance of OMEGA with respect to retrieving bioactive conformations. J. Mol. Graph. Model. 21(5): 449-462. doi: 10.1016/S1093-3263(02)00204-8
   PubMed Web of Science ®Google Scholar
• Winkler, F.K., D'Arcy, A., Hunziker, W. (1990). Structure of human pancreatic lipase. Nature. 343(6260): 771-774. doi: 10.1038/343771a0
   PubMed Web of Science ®Google Scholar
• Quezada-Calvillo, R., Robayo-Torres, C.C., Opekun, A.R., Sen, P., Ao, Z., Hamaker, B.R., Quaroni, A., Brayer, G.D., Wattler, S., Nehls, M.C., Sterchi, E.E., Nichols, B.L. (2007). Contribution of mucosal maltase-glucoamylase activities to mouse small intestinal starch alpha-glucogenesis. J. Nutr. 137(7): 1725-1733. doi: 10.1093/jn/137.7.1725
   PubMed Web of Science ®Google Scholar
• Martin, A.E., Montgomery, P.A. (1996). Acarbose: an alpha-glucosidase inhibitor. Am. J. Health Syst. Pharm. 53(19): 2277-2290. doi: 10.1093/ajhp/53.19.2277
   PubMed Web of Science ®Google Scholar