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BioMed Research International
Volume 2017, Article ID 8386065, 14 pages
https://doi.org/10.1155/2017/8386065
Research Article

Antioxidant and Antidiabetic Effects of Flavonoids: A Structure-Activity Relationship Based Study

1Department of Pharmaceutical Chemistry, Faculty of Pharmacy, International Islamic University Malaysia (IIUM), 25200 Kuantan, Pahang, Malaysia
2School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia (UKM), 46300 Bangi, Selangor, Malaysia

Correspondence should be addressed to Qamar Uddin Ahmed; ym.ude.muii@demhauq and Jalifah Latip; ym.ude.mku@hafilaj

Received 23 July 2017; Revised 21 September 2017; Accepted 12 October 2017; Published 28 November 2017

Academic Editor: Isabelle Chevalot

Copyright © 2017 Murni Nazira Sarian et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. J. Wall, “Antioxidants in prevention of reperfusion damage vascular endothelium,” The Trinity Student Medical Journal, vol. 1, pp. 67–71, 2000. View at Google Scholar
  2. D. Amic, D. Davidovic-Amic, D. Beslo, and N. Trinajstic, “Structureradical scavenging activity relationships of flavonoids,” Croatia ChemicaActa, vol. 76, pp. 55–61, 2003. View at Google Scholar
  3. M. A. Soobrattee, V. S. Neergheen, A. Luximon-Ramma, O. I. Aruoma, and T. Bahorun, “Phenolics as potential antioxidant therapeutic agents: Mechanism and actions,” Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis, vol. 579, no. 1-2, pp. 200–213, 2005. View at Publisher · View at Google Scholar · View at Scopus
  4. Y. Hanasaki, S. Ogawa, and S. Fukui, “The correlation between active oxygens scavenging and antioxidative effects of flavonoids,” Free Radical Biology & Medicine, vol. 16, no. 6, pp. 845–850, 1994. View at Publisher · View at Google Scholar · View at Scopus
  5. P. Cos, L. Ying, M. Calomme et al., “Structure-activity relationship and classification of flavonoids as inhibitors of xanthine oxidase and superoxide scavengers,” Journal of Natural Products, vol. 61, no. 1, pp. 71–76, 1998. View at Publisher · View at Google Scholar · View at Scopus
  6. I. Morel, G. Lescoat, P. Cogrel et al., “Antioxidant and iron-chelating activities of the flavonoids catechin, quercetin and diosmetin on iron-loaded rat hepatocyte cultures,” Biochemical Pharmacology, vol. 45, no. 1, pp. 13–19, 1993. View at Publisher · View at Google Scholar · View at Scopus
  7. R. Hirano, W. Sasamoto, A. Matsumoto, H. Itakura, O. Igarashi, and K. Kondo, “Antioxidant ability of various flavonoids against DPPH radicals and LDL oxidation,” Journal of Nutritional Science and Vitaminology, vol. 47, no. 5, pp. 357–362, 2001. View at Publisher · View at Google Scholar · View at Scopus
  8. C. C. Lima, R. P. Lemos, and L. M. Conserva, “Dilleniaceae family: an overview of its ethnomedicinal uses, biological and phytochemical profile,” Journal of Pharmacognosy and Phytochemistry, vol. 3, no. 2, pp. 181–204, 2014. View at Google Scholar
  9. J. S. Johansen, A. K. Harris, D. J. Rychly, and A. Ergul, “Oxidative stress and the use of antioxidants in diabetes: linking basic science to clinical pratice,” Cardiovascular Diabetology, vol. 4, article 5, 2005. View at Publisher · View at Google Scholar · View at Scopus
  10. P. Rosen, P. P. Nawroth, G. King, W. Möller, H. J. Tritschler, and L. Packer, “The role of oxidative stress in the onset and progression of diabetes and its complications: a summary of a congress series sponsored by UNESCO-MCBN, the American diabetes association and the German diabetes society,” Diabetes/Metabolism Research and Reviews, vol. 17, no. 3, pp. 189–212, 2001. View at Publisher · View at Google Scholar · View at Scopus
  11. F. Folli, D. Corradi, P. Fanti et al., “The role of oxidative stress in the pathogenesis of type 2 diabetes mellitus micro-and macrovascular complications: Avenues for a mechanistic-based therapeutic approach,” Current Diabetes Reviews, vol. 7, no. 5, pp. 313–324, 2011. View at Publisher · View at Google Scholar · View at Scopus
  12. B. Halliwell and J. M. C. Gutteridge, “Role of free radicals and catalytic metal ions in human disease: an overview,” Methods in Enzymology, vol. 186, pp. 1–85, 1990. View at Publisher · View at Google Scholar · View at Scopus
  13. A. Ceriello, “Oxidative stress and glycemic regulation,” Metabolism - Clinical and Experimental, vol. 49, no. 2, pp. 27–29, 2000. View at Publisher · View at Google Scholar · View at Scopus
  14. G. Paolisso, A. D'Amore, V. V. Balbi et al., “Plasma vitamin C affects glucose homeostasis in healthy subjects and non-insulin-dependent diabetics,” American Journal of Physiology, vol. 1266, pp. 261–268, 1994. View at Google Scholar
  15. G. Paolisso, A. D'Amore, D. Giugliano, A. Ceriello, M. Varricchio, and F. D'Onofrio, “Pharmacologic doses of vitamin E improve insulin action in healthy subjects and non-insulin-dependent diabetic patients,” American Journal of Clinical Nutrition, vol. 57, no. 5, pp. 650–656, 1993. View at Google Scholar · View at Scopus
  16. P. Faure, E. Rossini, J. L. Lafond, M. J. Richard, A. Favier, and S. Halimi, “Vitamin E improves the free radical defense system potential and insulin sensitivity of rats fed high fructose diets,” Journal of Nutrition, vol. 127, no. 1, pp. 103–107, 1997. View at Google Scholar · View at Scopus
  17. E. Nicolle, F. Souard, P. Faure, and A. Boumendjel, “Flavonoids as promising lead compounds in type 2 diabetes mellitus: molecules of interest and structure-activity relationship,” Current Medicinal Chemistry, vol. 18, no. 17, pp. 2661–2672, 2011. View at Publisher · View at Google Scholar · View at Scopus
  18. P. Bansal, P. Paul, J. Mudgal et al., “Antidiabetic, antihyperlipidemic and antioxidant effects of the flavonoid rich fraction of Pilea microphylla (L.) in high fat diet/streptozotocin-induced diabetes in mice,” Experimental and Toxicologic Pathology, vol. 64, no. 6, pp. 651–658, 2012. View at Publisher · View at Google Scholar · View at Scopus
  19. M. Aslan, D. Deliorman Orhan, N. Orhan, E. Sezik, and E. Yesilada, “In vivo antidiabetic and antioxidant potential of Helichrysum plicatum ssp. plicatum capitulums in streptozotocin-induced-diabetic rats,” Journal of Ethnopharmacology, vol. 109, no. 1, pp. 54–59, 2007. View at Publisher · View at Google Scholar · View at Scopus
  20. P. Sarkhail, S. Rahmanipour, S. Fadyevatan et al., “Antidiabetic effect of Phlomis anisodonta: effects on hepatic cells lipid peroxidation and antioxidant enzymes in experimental diabetes,” Pharmacological Research, vol. 56, no. 3, pp. 261–266, 2007. View at Publisher · View at Google Scholar · View at Scopus
  21. K. Muhammad, S. M. Mohd, A. Muhammad, H. Sardar, and U. Izhar, “A review on Malaysian medicinal plants having anti-hyperglycemic activity,” Journal of Coastal Life Medicine, vol. 4, no. 11, pp. 898–901, 2016. View at Google Scholar
  22. F. Abdullah, F. Jamaludin, N. H. Ismail, K. M. Khan, and S. N. Mohd Hashim, “Xanthine Oxidase Inhibitory Activity of,” The Open Conference Proceedings Journal, vol. 4, no. 1, pp. 168–168, 2013. View at Publisher · View at Google Scholar
  23. Q. U. Ahmed, B. B. S. Dogarai, M. Z. A. M Amiroudine et al., “Antidiabetic activity of the leaves of Tetraceraindica Merr. (Dilleniaceae) in vivo and in vitro,” Journal of Medicinal Plants Research, vol. 6, no. 49, pp. 5912–5922, 2012. View at Google Scholar
  24. Q. U. Ahmed, A. Umar, M. Z. A. M. Amiroudine, M. Taher, D. Susanti, and J. Latip, “Phytochemical investigation of the leaves of Tetracerascandens Linn. and antidiabetic activity of hypoletin,” in Proceedings of the International Conference on Science, Technology and Social Sciences (ICSTSS, Springer Science, pp. 591–608, 2014. View at Publisher · View at Google Scholar
  25. T. Mabry, K. R. Markham, and M. B. Thomas, The systematic identification of flavonoids, Springer Science & Business Media, 2012.
  26. C. Soler-Rivas, J. C. Espín, and H. J. Wichers, “An easy and fast test to compare total free radical scavenger capacity of foodstuffs,” Phytochemical Analysis, vol. 11, no. 5, pp. 330–338, 2000. View at Publisher · View at Google Scholar · View at Scopus
  27. L. L. Mensor, F. S. Menezes, G. G. Leitao et al., “Screening of Brazilian plant extracts for antioxidant activity by the use of DPPH free radical method,” Phytotherapy Research, vol. 15, pp. 127–130, 2001. View at Google Scholar
  28. B. Fauconneau, P. Waffo-Teguo, F. Huguet, L. Barrier, A. Decendit, and J.-M. Merillon, “Comparative study of radical scavenger and antioxidant properties of phenolic compounds from Vitis vinifera cell cultures using in vitro tests,” Life Sciences, vol. 61, no. 21, pp. 2103–2110, 1997. View at Publisher · View at Google Scholar · View at Scopus
  29. R. Re, N. Pellegrini, A. Proteggente, A. Pannala, M. Yang, and C. Rice-Evans, “Antioxidant activity applying an improved ABTS radical cation decolorization assay,” Free Radical Biology & Medicine, vol. 26, no. 9-10, pp. 1231–1237, 1999. View at Publisher · View at Google Scholar · View at Scopus
  30. W.-S. Chang, Y.-H. Chang, F.-J. Lu, and H.-C. Chiang, “Inhibitory effects of phenolics on xanthine oxidase,” Anticancer Reseach, vol. 14, no. 2, pp. 501–506, 1994. View at Google Scholar · View at Scopus
  31. L.-N. Huo, W. Wang, C.-Y. Zhang et al., “Bioassay-guided isolation and identification of xanthine oxidase inhibitory constituents from the leaves of perilla frutescens,” Molecules, vol. 20, no. 10, pp. 17848–17859, 2015. View at Publisher · View at Google Scholar · View at Scopus
  32. M. T. T. Nguyen, S. Awale, Y. Tezuka, Q. L. Tran, H. Watanabe, and S. Kadota, “Xanthine oxidase inhibitory activity of Vietnamese medicinal plants,” Biological & Pharmaceutical Bulletin, vol. 27, no. 9, pp. 1414–1421, 2004. View at Publisher · View at Google Scholar · View at Scopus
  33. A. Abdullahi, R. Hamzah, A. Jigam et al., “Inhibitory activity of xanthine oxidase by fractions Crateva adansonii,” Journal of Acute Disease, vol. 1, no. 2, pp. 126–129, 2012. View at Publisher · View at Google Scholar
  34. A. Szydlowska-Czerniak, K. Trokowski, G. Karlovits, and E. Szłyk, “Effect of refining processes on antioxidant capacity, total contents of phenolics and carotenoids in palm oils,” Food Chemistry, vol. 129, no. 3, pp. 1187–1192, 2011. View at Publisher · View at Google Scholar · View at Scopus
  35. A. Khatib, V. Perumal, Q. Ahmed, B. Uzir, and S. Murugesu, “Low inhibition of alpha-glucosidase and xanthine oxidase activities of ethanol extract of Momordica charantia fruit,” Journal of Pharmaceutical Negative Results, vol. 8, no. 1, p. 20, 2017. View at Publisher · View at Google Scholar
  36. L. J. Harrison, G.-L. Sia, and K.-Y. Sim, “5,7-Dihydroxy-8-methoxyflavone from Tetracera indica,” Planta Medica, vol. 60, no. 5, pp. 493-494, 1994. View at Publisher · View at Google Scholar · View at Scopus
  37. A. A. L. Mesquita, D. D. B. Corrêa, A. P. De Pádua, M. L. O. Guedes, and O. R. Gottlieb, “Flavonoids from four compositae species,” Phytochemistry, vol. 25, no. 5, pp. 1255-1256, 1986. View at Publisher · View at Google Scholar · View at Scopus
  38. T. Supinya, S. Sanan, and K. Sopa, “Anti-allergic activity of compounds from Kaempferia parviflora,” Journal of Ethnopharmacology, vol. 116, pp. 191–193, 2008. View at Google Scholar
  39. P. Seetharaman, S. Gnanasekar, R. Chandrasekaran, G. Chandrakasan, M. Kadarkarai, and S. Sivaperumal, “Isolation and characterization of anticancer flavone chrysin (5,7-dihydroxy flavone)-producing endophytic fungi from Passiflora incarnata L. leaves,” Annals of Microbiology, vol. 67, no. 4, pp. 321–331, 2017. View at Publisher · View at Google Scholar · View at Scopus
  40. Y. Miyasaki, J. D. Rabenstein, J. Rhea et al., “Isolation and characterization of antimicrobial compounds in plant extracts against multidrug-resistant Acinetobacter baumannii,” PLoS ONE, vol. 8, no. 4, Article ID e61594, 2013. View at Publisher · View at Google Scholar · View at Scopus
  41. J. Baumann, G. Wurm, and F. Von Bruchhausen, “Prostaglandin synthetase inhibition by flavonoids and phenolic compounds in relation to their O2-scavenging properties (author's transl),” Archiv der Pharmazie, vol. 313, no. 4, p. 330, 1980. View at Publisher · View at Google Scholar
  42. A. I. Huguet, S. Máñez, and M. J. Alcaraz, “Superoxide scavenging properties of flavonoids in a non-enzymic system,” ZeitschriftfürNaturforschung C, vol. 45, no. 1-2, pp. 19–24, 1990. View at Google Scholar
  43. N. Cotelle, J. L. Bernier, J. P. Hénichart, J. P. Catteau, E. Gaydou, and J. C. Wallet, “Scavenger and antioxidant properties of ten synthetic flavones,” Free Radical Biology & Medicine, vol. 13, no. 3, pp. 211–219, 1992. View at Publisher · View at Google Scholar · View at Scopus
  44. G. Cao, E. Sofic, and R. L. Prior, “Antioxidant and prooxidant behavior of flavonoids: structure-activity relationships,” Free Radical Biology & Medicine, vol. 22, no. 5, pp. 749–760, 1997. View at Publisher · View at Google Scholar · View at Scopus
  45. K. E. Heim, A. R. Tagliaferro, and D. J. Bobilya, “Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships,” The Journal of Nutritional Biochemistry, vol. 13, no. 10, pp. 572–584, 2002. View at Publisher · View at Google Scholar · View at Scopus
  46. A. Seyoum, K. Asres, and F. K. El-Fiky, “Structure–radical scavenging activity relationships of flavonoids,” Phytochemistry, vol. 67, no. 18, pp. 2058–2070, 2006. View at Publisher · View at Google Scholar · View at Scopus
  47. J. Jang, H. P. Kim, and H. Park, “Structure and anti-inflammatory activity relationships of wogonin derivatives,” Archives of Pharmacal Research, vol. 28, no. 8, pp. 877–884, 2005. View at Publisher · View at Google Scholar · View at Scopus
  48. C. Rosak and G. Mertes, “Effects of acarbose on proinsulin and insulin secretion and their potential significance for the intermediary metabolism and cardiovascular system,” Current Diabetes Reviews, vol. 5, no. 3, pp. 157–164, 2009. View at Publisher · View at Google Scholar · View at Scopus
  49. T. Nishioka, J. Kawabata, and Y. Aoyama, “Baicalein, an α-glucosidase inhibitor from Scutellaria baicalensis,” Journal of Natural Products, vol. 61, no. 11, pp. 1413–1415, 1998. View at Publisher · View at Google Scholar · View at Scopus
  50. K. Tadera, Y. Minami, K. Takamatsu, and T. Matsuoka, “Inhibition of α-glucosidase and α-amylase by flavonoids,” Journal of Nutritional Science and Vitaminology, vol. 52, no. 2, pp. 149–153, 2006. View at Publisher · View at Google Scholar · View at Scopus
  51. Y. Zhenhua, Z. Wei, F. Fajin, Z. Yong, and K. Wenyi, “α-Glucosidase inhibitors isolated from medicinal plants,” Journal of Food Science and Human Wellness, vol. 3, no. 3, pp. 136–174, 2014. View at Google Scholar
  52. N. F. Brás, N. M. F. Cerqueira, M. J. Ramos, and P. A. Fernandes, “Glycosidase inhibitors: a patent review (2008–2013),” Expert Opinion on Therapeutic Patents, vol. 24, no. 8, pp. 857–874, 2014. View at Publisher · View at Google Scholar · View at Scopus
  53. Y. Q. Li, F. C. Zhou, F. Gao, J. S. Bian, and F. Shan, “Comparative evaluation of quercetin, isoquercetin and rutin as inhibitors of α-glucosidase,” Journal of Agricultural and Food Chemistry, vol. 57, no. 24, pp. 11463–11468, 2009. View at Publisher · View at Google Scholar · View at Scopus
  54. H. Xu, “Inhibition kinetics of flavonoids on yeast α-glucosidase merged with docking simulations,” Protein and Peptide Letters, vol. 17, no. 10, pp. 1270–1279, 2010. View at Publisher · View at Google Scholar · View at Scopus
  55. J. Vaya, S. Mahmood, A. Goldblum et al., “Inhibition of LDL oxidation by flavonoids in relation to their structure and calculated enthalpy,” Phytochemistry, vol. 62, no. 1, pp. 89–99, 2003. View at Publisher · View at Google Scholar · View at Scopus
  56. X. Peng, G. Zhang, Y. Liao, and D. Gong, “Inhibitory kinetics and mechanism of kaempferol on α-glucosidase,” Food Chemistry, vol. 190, pp. 207–215, 2016. View at Publisher · View at Google Scholar · View at Scopus
  57. J. Kawabata, K. Mizuhata, E. Sato, T. Nishioka, Y. Aoyama, and T. Kasai, “6-Hydroxyflavonoids as α-glucosidase inhibitors from marjoram (origanum majorana) leaves,” Bioscience, Biotechnology, and Biochemistry, vol. 67, no. 2, pp. 445–447, 2003. View at Publisher · View at Google Scholar · View at Scopus
  58. R. Mentlein, “Dipeptidyl-peptidase IV (CD26)-role in the inactivation of regulatory peptides,” Regulatory Peptides, vol. 85, no. 1, pp. 9–24, 1999. View at Publisher · View at Google Scholar · View at Scopus
  59. C. F. Deacon, M. A. Nauck, J. Meier, K. Hücking, and J. J. Holst, “Degradation of endogenous and exogenous gastric inhibitory polypeptide in healthy and in type 2 diabetic subjects as revealed using a new assay for the intact peptide,” The Journal of Clinical Endocrinology & Metabolism, vol. 85, no. 10, pp. 3575–3581, 2000. View at Google Scholar · View at Scopus
  60. E. P. Semighini, J. A. Resende, P. De Andrade et al., “Using computer-aided drug design and medicinal chemistry strategies in the fight against diabetes,” Journal of Biomolecular Structure and Dynamics, vol. 28, no. 5, pp. 787–796, 2011. View at Publisher · View at Google Scholar · View at Scopus
  61. P. Jadav, R. Bahekar, S. R. Shah et al., “Long-acting peptidomimetics based DPP-IV inhibitors,” Bioorganic & Medicinal Chemistry Letters, vol. 22, no. 10, pp. 3516–3521, 2012. View at Publisher · View at Google Scholar · View at Scopus
  62. J. Fan, M. H. Johnson, M. A. Lila, G. Yousef, and E. G. De Mejia, “Berry and citrus phenolic compounds inhibit dipeptidyl peptidase IV: Implications in diabetes management,” Evidence-Based Complementary and Alternative Medicine, vol. 2013, Article ID 479505, 2013. View at Publisher · View at Google Scholar · View at Scopus
  63. P. L. Teissedre, E. N. Frankel, A. L. Waterhouse, H. Peleg, and J. Bruce German, “Inhibition of in vitro human LDL oxidation by phenolic antioxidants from grapes and wines,” Journal of the Science of Food and Agriculture, vol. 70, no. 1, pp. 55–61, 1996. View at Publisher · View at Google Scholar · View at Scopus