Monday, 17 September 2018

Antidiabetic potential of phytochemicals isolated from the stem bark of Myristica fatua Houtt. var. magnifica (Bedd.) Sinclair

Bioorganic and Medicinal Chemistry Volume 26, Issue 12, 23 July 2018, Pages 3461-3467 Prabha, B.a, Neethu, S.a,b, Krishnan, S.L.c, Sherin, D.R.d, Madhukrishnan, M.a, Ananthakrishnan, R.e, Rameshkumar, K.B.e, Manojkumar, T.K.d, Jayamurthy, P.b,c, Radhakrishnan, K.V.a,bEmail Author View Correspondence (jump link) aChemical Science and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology, Thiruvananthapuram, 695019, India bAcademy of Scientific and Innovative Research (AcSIR), Thiruvananthapuram, 695019, India cAgroprocessing and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology, Thiruvananthapuram, 695019, India View additional affiliations Abstract View references (39) Phytochemical investigation of the stem bark of Myristica fatua Houtt. led to the isolation of a new compound 1 (3-tridecanoylbenzoic acid), along with six known acylphenols (2–7). All the compounds displayed moderate inhibitory activity on α-amylase and significant activity on α-glucosidase; however malabaricone B (6) and C (7) were identified as potent α-glucosidase inhibitors with IC50 values of 63.70 ± 0.546, and 43.61 ± 0.620 µM respectively. Acylphenols (compounds 3–7) also showed significant antiglycation property. The molecular docking and dynamics simulation studies confirmed the efficient binding of malabaricone C with C-terminus of human maltase-glucoamylase (2QMJ). Malabaricone B also enhanced the 2-NBDG [2-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-2-deoxy glucose] uptake in L6 myotubes. These findings demonstrate that acylphenols isolated from Myristica fatua Houtt. can be considered as a lead scaffold for the treatment of type II diabetes mellitus. © 2018 Elsevier Ltd Author keywords Glucose uptake in L6 myotubesMyristica fatua HouttProtein glycationSimulation studiesα-Amylaseα-Glucosidase Indexed keywords EMTREE drug terms: 2 [n (7 nitrobenz 2 oxa 1,3 diazol 4 yl)amino] 2 deoxyglucose3 tridecanoylbenzoic acidacarboseacylphenol derivativealpha glucosidaseamylaseantidiabetic agentascorbic acidcarbohydrate derivativedichloromethanemalabaricone Bmalabaricone CMyristica fatua extractplant extractplant medicinal productunclassified drug EMTREE medical terms: animal cellantidiabetic activityantiglycation activityArticlebarkcarbohydrate transportcarboxy terminal sequenceconcentration responsecontrolled studydrug activitydrug cytotoxicitydrug identificationdrug isolationdrug potencydrug protein bindingdrug structuredrug uptakeenzyme inhibitionIC50L6 myotubemolecular dockingmolecular dynamicsmyotubeMyristicaMyristica fatuanonhumanphytochemistryrat Chemicals and CAS Registry Numbers: acarbose, 56180-94-0; alpha glucosidase, 9001-42-7; amylase, 9000-90-2, 9000-92-4, 9001-19-8; ascorbic acid, 134-03-2, 15421-15-5, 50-81-7; dichloromethane, 75-09-2 Funding details Funding number Funding sponsor Acronym Funding opportunities SB/S1/OC-24/2014 Science and Engineering Research Board SERB See opportunities by SERB Science and Engineering Research Board SERB See opportunities by SERB University Grants Commission UGC ORIGIN-CSC-0108 Council of Scientific and Industrial Research CSIR See opportunities by CSIR NaPAHA CSC-0130 Council of Scientific and Industrial Research CSIR See opportunities by CSIR Funding text BP, SN, and MM thank UGC and CSIR for research fellowships. Financial assistance from Science and Engineering Research Board (SERB), New Delhi (SB/S1/OC-24/2014) and Council of Scientific and Industrial Research (12th FYP projects: ORIGIN-CSC-0108 and NaPAHA CSC-0130) are greatly acknowledged. We thank Mrs. Saumini Mathew and Mrs. S. Viji, of CSIR-NIIST, Thiruvananthapuram, for recording NMR and mass spectra. Authors acknowledge Dr. Jubi John, Mrs. Aparna P. S and Mr. Ijinu T. P for the help rendered during the preparation of the manuscript. A ISSN: 09680896 CODEN: BMECE Source Type: Journal Original language: English DOI: 10.1016/j.bmc.2018.05.020 Document Type: Article Publisher: Elsevier Ltd References (39) View in search results format All Export Print E-mail Save to PDF Create bibliography 1 Ross, S.A., Gulve, E.A., Wang, M. Chemistry and biochemistry of type 2 diabetes (2004) Chemical Reviews, 104 (3), pp. 1255-1282. Cited 224 times. doi: 10.1021/cr0204653 View at Publisher 2 Global report on diabetes, World Health Organisation. April 2016. 3 Trapero, A., Llebaria, A. A prospect for pyrrolidine iminosugars as antidiabetic α-glucosidase inhibitors (2012) Journal of Medicinal Chemistry, 55 (23), pp. 10345-10346. Cited 22 times. doi: 10.1021/jm301682r View at Publisher 4 Yonemoto, R., Shimada, M., Gunawan-Puteri, M.D.P.T., Kato, E., Kawabata, J. α-amylase inhibitory triterpene from abrus precatorius leaves (2014) Journal of Agricultural and Food Chemistry, 62 (33), pp. 8411-8414. Cited 15 times. doi: 10.1021/jf502667z View at Publisher 5 Riya, M.P., Antu, K.A., Pal, S., Chandrakanth, K.C., Anilkumar, K.S., Tamrakar, A.K., Srivastava, A.K., (...), Raghu, K.G. Antidiabetic property of Aerva lanata (L.) Juss. ex Schult. is mediated by inhibition of alpha glucosidase, protein glycation and stimulation of adipogenesis (2015) Journal of Diabetes, 7 (4), pp. 548-561. Cited 5 times. doi: 10.1111/1753-0407.12216 View at Publisher 6 Patel, O.P.S., Mishra, A., Maurya, R., Saini, D., Pandey, J., Taneja, I., Raju, K.S.R., (...), Yadav, P.P. Naturally Occurring Carbazole Alkaloids from Murraya koenigii as Potential Antidiabetic Agents (2016) Journal of Natural Products, 79 (5), pp. 1276-1284. Cited 14 times. doi: 10.1021/acs.jnatprod.5b00883 View at Publisher 7 Prabhakar, P.K., Doble, M. Interaction of cinnamic acid derivatives with commercial hypoglycemic drugs on 2-deoxyglucose uptake in 3T3-L1 adipocytes (2011) Journal of Agricultural and Food Chemistry, 59 (18), pp. 9835-9844. Cited 22 times. doi: 10.1021/jf2015717 View at Publisher 8 Victor, J.N., John, R.S. (2006) N Engl J Med, 354, pp. 731-739. Cited 2 times. 9 Hollander, P. Anti-diabetes and anti-obesity medications: Effects on weight in people with diabetes (2007) Diabetes Spectrum, 20 (3), pp. 159-165. Cited 34 times. doi: 10.2337/diaspect.20.3.159 View at Publisher 10 Nissen, S.E., Wolski, K. Effect of rosiglitazone on the risk of myocardial infarction and death from cardiovascular causes (2007) New England Journal of Medicine, 356 (24), pp. 2457-2471. Cited 3290 times. doi: 10.1056/NEJMoa072761 View at Publisher 11 Muhammad, A., Guerrero-Analco, J.A., Martineau, L.C., Musallam, L., Madiraju, P., Nachar, A., Saleem, A., (...), Arnason, J.T. Antidiabetic compounds from Sarracenia purpurea used traditionally by the eeyou istchee Cree first nation (2012) Journal of Natural Products, 75 (7), pp. 1284-1288. Cited 15 times. doi: 10.1021/np3001317 View at Publisher 12 Chang, K.-C., Li, L., Sanborn, T.M., Shieh, B., Lenhart, P., Ammar, D., LaBarbera, D.V., (...), Petrash, J.M. Characterization of Emodin as a Therapeutic Agent for Diabetic Cataract (2016) Journal of Natural Products, 79 (5), pp. 1439-1444. Cited 5 times. doi: 10.1021/acs.jnatprod.6b00185 View at Publisher 13 Kim, S., Go, G.-W., Imm, J.-Y. Promotion of Glucose Uptake in C2C12 Myotubes by Cereal Flavone Tricin and Its Underlying Molecular Mechanism (2017) Journal of Agricultural and Food Chemistry, 65 (19), pp. 3819-3826. Cited 4 times. doi: 10.1021/acs.jafc.7b00578 View at Publisher 14 Spínola, V., Castilho, P.C. Evaluation of Asteraceae herbal extracts in the management of diabetes and obesity. Contribution of caffeoylquinic acids on the inhibition of digestive enzymes activity and formation of advanced glycation end-products (in vitro) (2017) Phytochemistry, 143, pp. 29-35. Cited 5 times. doi: 10.1016/j.phytochem.2017.07.006 View at Publisher 15 Ajish, K.R., Antu, K.A., Riya, M.P., Preetharani, M.R., Raghu, K.G., Dhanya, B.P., Radhakrishnan, K.V. Studies on α-glucosidase, aldose reductase and glycation inhibitory properties of sesquiterpenes and flavonoids of Zingiber zerumbet Smith (2015) Natural Product Research, 29 (10), pp. 947-952. Cited 15 times. doi: 10.1080/14786419.2014.956741 View at Publisher 16 Sasikumar, P., Prabha, B., Reshmitha, T.R., Veluthoor, S., Pradeep, A.K., Rohit, K.R., Dhanya, B.P., (...), Radhakrishnan, K.V. Comparison of antidiabetic potential of (+) and (-)-hopeaphenol, a pair of enantiomers isolated from: Ampelocissus indica (L.) and Vateria indica Linn., with respect to inhibition of digestive enzymes and induction of glucose uptake in L6 myotubes (2016) RSC Advances, 6 (80), pp. 77075-77082. Cited 4 times. doi: 10.1039/c6ra14334b View at Publisher 17 Billoa, M., Cabalionb, P., Waikedreb, J. (2005) J Ethnopharmacol, 96, pp. 195-200. 18 Viveka, M.R., Chandrashekar, K.R. Antioxidant and antibacterial activities of Myristica fatua var. Magnifica (Beddome) Sinclair (2016) Asian Journal of Pharmaceutical and Clinical Research, 9 (4), pp. 235-239. Cited 3 times. 19 Desrivot, J., Waikedre, J., Cabalion, P., Herrenknecht, C., Bories, C., Hocquemiller, R., Fournet, A. Antiparasitic activity of some New Caledonian medicinal plants (2007) Journal of Ethnopharmacology, 112 (1), pp. 7-12. Cited 41 times. doi: 10.1016/j.jep.2007.01.026 View at Publisher 20 Pandey, R., Mahar, R., Hasanain, M., Shukla, S.K., Sarkar, J., Rameshkumar, K.B., Kumar, B. Rapid screening and quantitative determination of bioactive compounds from fruit extracts of Myristica species and their in vitro antiproliferative activity (2016) Food Chemistry, 211, pp. 483-493. Cited 8 times. doi: 10.1016/j.foodchem.2016.05.065 View at Publisher 21 Fajriah, S., Darmawan, A., Megawati, Hudiyono, S., Kosela, S., Hanafi, M. New cytotoxic compounds from Myristica fatua Houtt leaves against MCF-7 cell lines (2017) Phytochemistry Letters, 20, pp. 36-39. Cited 2 times. doi: 10.1016/j.phytol.2017.03.013 View at Publisher 22 Megawati, Darmawan, A. (2017) J Indonesian Pharm, 28, pp. 82-90. 23 Xio, Z., Storms, R., Tsang, A. (2006) Anal Biochem, 351, pp. 146-148. 24 Apostolidis, E., Kwon, Y.-I., Shetty, K. Inhibitory potential of herb, fruit, and fungal-enriched cheese against key enzymes linked to type 2 diabetes and hypertension (2007) Innovative Food Science and Emerging Technologies, 8 (1), pp. 46-54. Cited 207 times. doi: 10.1016/j.ifset.2006.06.001 View at Publisher 25 Jedsadayanmata, A. (2005) J Naresun Univ, 13, pp. 35-41. Cited 39 times. 26 Schro¨dinger User Manuals, Glide 5.8; Schro¨dinger, New York, NY: L.L.C.;2012. 27 QikProp 3.5; Schro¨dinger, New York, NY: L.L.C.; 2012. 28 Williams, L.K., Li, C., Withers, S.G., Brayer, G.D. Order and disorder: Differential structural impacts of myricetin and ethyl caffeate on human amylase, an antidiabetic target (2012) Journal of Medicinal Chemistry, 55 (22), pp. 10177-10186. Cited 25 times. doi: 10.1021/jm301273u View at Publisher 29 Ren, L., Qin, X., Cao, X., Wang, L., Bai, F., Bai, G., Shen, Y. Structural insight into substrate specificity of human intestinal maltase-glucoamylase (2011) Protein and Cell, 2 (10), pp. 827-836. Cited 61 times. doi: 10.1007/s13238-011-1105-3 View at Publisher 30 Sim, L., Quezada-Calvillo, R., Sterchi, E.E., Nichols, B.L., Rose, D.R. Human Intestinal Maltase-Glucoamylase: Crystal Structure of the N-Terminal Catalytic Subunit and Basis of Inhibition and Substrate Specificity (2008) Journal of Molecular Biology, 375 (3), pp. 782-792. Cited 117 times. doi: 10.1016/j.jmb.2007.10.069 View at Publisher 31 Mosmann, T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays (1983) Journal of Immunological Methods, 65 (1-2), pp. 55-63. Cited 35476 times. doi: 10.1016/0022-1759(83)90303-4 View at Publisher 32 Somwar, R., Sweeney, G., Ramlal, T., Klip, A. Stimulation of glucose and amino acid transport and activation of the insulin signaling pathways by insulin lispro in L6 skeletal muscle cells (1998) Clinical Therapeutics, 20 (1), pp. 125-140. Cited 46 times. doi: 10.1016/S0149-2918(98)80040-4 View at Publisher 33 Tamrakar, A.K., Jaiswal, N., Yadav, P.P., Maurya, R., Srivastava, A.K. Pongamol from Pongamia pinnata stimulates glucose uptake by increasing surface GLUT4 level in skeletal muscle cells (2011) Molecular and Cellular Endocrinology, 339 (1-2), pp. 98-104. Cited 42 times. doi: 10.1016/j.mce.2011.03.023 View at Publisher 34 Kumar, N.S., Herath, H.M.T.B., Karunaratne, V. Arylalkanones from Myristica dactyloides (1988) Phytochemistry, 27 (2), pp. 465-468. Cited 19 times. doi: 10.1016/0031-9422(88)83121-2 View at Publisher 35 Purushothaman, K.K., Sarada, A., Connolly, J.D. Malabaricones A-D, novel diarylnonanoids from Myristica malabarica Lam (Myristicaceae) (1977) Journal of the Chemical Society, Perkin Transactions 1, (5), pp. 587-588. Cited 45 times. View at Publisher 36 Sui, X., Zhang, Y., Zhou, W. In vitro and in silico studies of the inhibition activity of anthocyanins against porcine pancreatic α-amylase (2016) Journal of Functional Foods, 21, pp. 50-57. Cited 16 times. doi: 10.1016/j.jff.2015.11.042 View at Publisher 37 Sun, H., Wang, D., Song, X., Zhang, Y., Ding, W., Peng, X., Zhang, X., (...), Yu, P. Natural Prenylchalconaringenins and Prenylnaringenins as Antidiabetic Agents: α-Glucosidase and α-Amylase Inhibition and in Vivo Antihyperglycemic and Antihyperlipidemic Effects (2017) Journal of Agricultural and Food Chemistry, 65 (8), pp. 1574-1581. Cited 11 times. doi: 10.1021/acs.jafc.6b05445 View at Publisher 38 Sivasothya, Y., Yong, L.-K., Hoong, L.-K., Litaudon, M., Awang, K. (2016) Phytochemistry, 122, pp. 265-269. Cited 2 times. 39 Adrover, M., Mariño, L., Sanchis, P., Pauwels, K., Kraan, Y., Lebrun, P., Vilanova, B., (...), Donoso, J. Mechanistic insights in glycation-induced protein aggregation (2014) Biomacromolecules, 15 (9), pp. 3449-3462. Cited 25 times. doi: 10.1021/bm501077j View at Publisher Rameshkumar, K.B.; Chemical Science and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology, Thiruvananthapuram, India © Copyright 2018 Elsevier B.V., All rights reserved.