Natural flavonoids as antidiabetic agents. The binding of gallic and ellagic acids to glycogen phosphorylase b

FEBS Letters

Volumn 589, Issue 15, 2015, Pages 1787-1794

  Kyriakis, Efthimios ^a   Stravodimos, George A ^a   Kantsadi, Anastassia L ^a   Chatzileontiadou, Demetra S M ^a   Skamnaki, Vassiliki T ^a   Leonidas, Demetres D ^a  

^a UNIVERSITY OF THESSALY   (Greece)

Author keywords

Abbreviations GP glycogen phosphorylase; Glc 1 P d glucose 1 phosphate; GPb rabbit muscle glycogen phosphorylase b; PLP pyridoxal 5 phosphate; r.m.s.d. root mean square displacement

Indexed keywords

CAFFEINE; CHRYSIN; ELLAGIC ACID; FLAVONOID; FLAVOPIRIDOL; GALLIC ACID; GLUCOSE 1 PHOSPHATE; GLYCOGEN PHOSPHORYLASE B; ANTIDIABETIC AGENT; GLYCOGEN PHOSPHORYLASE;

ANIMAL TISSUE; ANTIDIABETIC ACTIVITY; ARTICLE; BINDING AFFINITY; BINDING SITE; CATALYSIS; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG EFFICACY; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG STRUCTURE; ENZYME INHIBITION; GRAPE; HYDROPHOBICITY; NONHUMAN; PRIORITY JOURNAL; PROTEIN CONFORMATION; PROTEIN PHOSPHORYLATION; PROTEIN PROTEIN INTERACTION; SKELETAL MUSCLE; X RAY CRYSTALLOGRAPHY; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; ENZYMOLOGY; METABOLISM; RABBIT;

ORYCTOLAGUS CUNICULUS;

ANIMALS; ELLAGIC ACID; FLAVONOIDS; GALLIC ACID; GLYCOGEN PHOSPHORYLASE; GLYCOGEN PHOSPHORYLASE, MUSCLE FORM; HYPOGLYCEMIC AGENTS; MOLECULAR STRUCTURE; MUSCLE, SKELETAL; RABBITS;

EID: 84934442977     PISSN: 00145793     EISSN: 18733468     Source Type: Journal    
DOI: 10.1016/j.febslet.2015.05.013     Document Type: Article

References (38)

1. N.G. Oikonomakos Glycogen phosphorylase as a molecular target for type 2 diabetes therapy Curr. Protein Pept. Sci. 3 2002 561 586
2. L. Somsak, K. Czifrak, M. Toth, E. Bokor, E.D. Chrysina, K.M. Alexacou, J.M. Hayes, C. Tiraidis, E. Lazoura, D.D. Leonidas, S.E. Zographos, and N.G. Oikonomakos New inhibitors of glycogen phosphorylase as potential antidiabetic agents Curr. Med. Chem. 15 2008 2933 2983
3. N.G. Oikonomakos, and L. Somsak Advances in glycogen phosphorylase inhibitor design Curr. Opin. Investig. Drugs 9 2008 379 395
4. J.M. Hayes, A.L. Kantsadi, and D.D. Leonidas Natural products and their derivatives as inhibitors of glycogen phosphorylase: potential treatment for type 2 diabetes Phytochem. Rev. 13 2014 471 498
5. L. Agius Physiological control of liver glycogen metabolism: lessons from novel glycogen phosphorylase inhibitors Mini Rev. Med. Chem. 10 2010 1175 1187
6. J. Monod, J. Wyman, and J.P. Changeux On the nature of allosteric transitions: a plausible model J. Mol. Biol. 12 1965 88 118
7. A.L. Kantsadi, A. Apostolou, S. Theofanous, G.A. Stravodimos, E. Kyriakis, V.A. Gorgogietas, D.S. Chatzileontiadou, K. Pegiou, V.T. Skamnaki, D. Stagos, D. Kouretas, A.M. Psarra, S.A. Haroutounian, and D.D. Leonidas Biochemical and biological assessment of the inhibitory potency of extracts from vinification byproducts of Vitis vinifera extracts against glycogen phosphorylase Food Chem. Toxicol. 67 2014 35 43
8. L. Somsak Glucose derived inhibitors of glycogen phosphorylase C. R. Chim. 14 2011 211 223
9. P.J. Kasvinsky, R.J. Fletterick, and N.B. Madsen Regulation of the dephosphorylation of glycogen phosphorylase a and synthase b by glucose and caffeine in isolated hepatocytes Can. J. Biochem. 59 1981 387 395
10. N. Ercan-Fang, and F.Q. Nuttall The effect of caffeine and caffeine analogs on rat liver phosphorylase a activity J. Pharmacol. Exp. Ther. 280 1997 1312 1318
11. E.K. Kalra Nutraceutical-definition and introduction AAPS PharmSci. 5 2003 E25
12. M. Whitman Understanding the perceived need for complementary and alternative nutraceuticals: lifestyle issues Clin. J. Oncol. Nurs. 5 2001 190 194
13. K.C. Ong, and H.E. Khoo Effects of myricetin on glycemia and glycogen metabolism in diabetic rats Life Sci. 67 2000 1695 1705
14. M. Ahmad, M.S. Akhtar, T. Malik, and A.H. Gilani Hypoglycaemic action of the flavonoid fraction of Cuminum nigrum seeds Phytother. Res. 14 2000 103 106
15. L. Anila, and N.R. Vijayalakshmi Beneficial effects of flavonoids from Sesamum indicum, Emblica officinalis and Momordica charantia Phytother. Res. 14 2000 592 595
16. S. Jakobs, D. Fridrich, S. Hofem, G. Pahlke, and G. Eisenbrand Natural flavonoids are potent inhibitors of glycogen phosphorylase Mol. Nutr. Food Res. 50 2006 52 57
17. L.J. Hampson, C. Arden, L. Agius, M. Ganotidis, M.N. Kosmopoulou, C. Tiraidis, Y. Elemes, C. Sakarellos, D.D. Leonidas, and N.G. Oikonomakos Bioactivity of glycogen phosphorylase inhibitors that bind to the purine nucleoside site Bioorg. Med. Chem. 14 2006 7835 7845
18. N.G. Oikonomakos, J.B. Schnier, S.E. Zographos, V.T. Skamnaki, K.E. Tsitsanou, and L.N. Johnson Flavopiridol inhibits glycogen phosphorylase by binding at the inhibitor site J. Biol. Chem. 275 2000 34566 34573
19. K.E. Tsitsanou, J.M. Hayes, M. Keramioti, M. Mamais, N.G. Oikonomakos, A. Kato, D.D. Leonidas, and S.E. Zographos Sourcing the affinity of flavonoids for the glycogen phosphorylase inhibitor site via crystallography, kinetics and QM/MM-PBSA binding studies: comparison of chrysin and flavopiridol Food Chem. Toxicol. 61 2013 14 27
20. A. Kato, N. Nasu, K. Takebayashi, I. Adachi, Y. Minami, F. Sanae, N. Asano, A.A. Watson, and R.J. Nash Structure-activity relationships of flavonoids as potential inhibitors of glycogen phosphorylase J. Agric. Food Chem. 56 2008 4469 4473
21. V.G. Tsirkone, E. Tsoukala, C. Lamprakis, S. Manta, J.M. Hayes, V.T. Skamnaki, C. Drakou, S.E. Zographos, D. Komiotis, and D.D. Leonidas 1-(3-Deoxy-3-fluoro-beta-d-glucopyranosyl) pyrimidine derivatives as inhibitors of glycogen phosphorylase b: kinetic, crystallographic and modelling studies Bioorg. Med. Chem. 18 2010 3413 3425
22. J.M. Hayes, V.T. Skamnaki, G. Archontis, C. Lamprakis, J. Sarrou, N. Bischler, A.L. Skaltsounis, S.E. Zographos, and N.G. Oikonomakos Kinetics, in silico docking, molecular dynamics, and MM-GBSA binding studies on prototype indirubins, KT5720, and staurosporine as phosphorylase kinase ATP-binding site inhibitors: the role of water molecules examined Proteins 79 2011 703 719
23. R.J. Leatherbarrow GraFit version 4.06 1998 Erithacus Software Ltd Staines UK
24. K.M. Alexacou, A.C. Tenchiu Deleanu, E.D. Chrysina, M.D. Charavgi, I.D. Kostas, S.E. Zographos, N.G. Oikonomakos, and D.D. Leonidas The binding of beta-d-glucopyranosyl-thiosemicarbazone derivatives to glycogen phosphorylase: a new class of inhibitors Bioorg. Med. Chem. 18 2010 7911 7922
25. A.G.W. Leslie, and H.R. Powell Processing diffraction data with mosflm R.J. Read, J.I. Sussman, Evolving Methods for Macromolecular Crystallography 2007 Springer 41 51
26. W. Kabsch Xds Acta Crystallogr. D Biol. Crystallogr. 66 2010 125 132
27. CCP4, The CCP4 suite: programs for protein crystallography Acta Crystallogr. D 50 1994 760 763
28. G.N. Murshudov, P. Skubak, A.A. Lebedev, N.S. Pannu, R.A. Steiner, R.A. Nicholls, M.D. Winn, F. Long, and A.A. Vagin REFMAC5 for the refinement of macromolecular crystal structures Acta Crystallogr. D Biol. Crystallogr. 67 2011 355 367
29. V.B. Chen, W.B. Arendall 3rd, J.J. Headd, D.A. Keedy, R.M. Immormino, G.J. Kapral, L.W. Murray, J.S. Richardson, and D.C. Richardson MolProbity: all-atom structure validation for macromolecular crystallography Acta Crystallogr. D Biol. Crystallogr. 66 2010 12 21
30. W.L. DeLano, The PyMol Molecular Visualization System in Sa Carlos, CA, USA, 2002.
31. J.W. Hudson, G.B. Golding, and M.M. Crerar Evolution of allosteric control in glycogen phosphorylase J. Mol. Biol. 234 1993 700 721
32. A.C. Papageorgiou, N.G. Oikonomakos, and D.D. Leonidas Inhibition of rabbit muscle glycogen phosphorylase by d-gluconohydroximo-1,5-lactone-N-phenylurethane Arch. Biochem. Biophys. 272 1989 376 385
33. I.H. Segel Enzyme Kinetics 1993 Wiley Interscience New York
34. N.B. Madsen, S. Shechosky, and R.J. Fletterick Site-site interactions in glycogen phosphorylase b probed by ligands specific for each site Biochemistry 22 1983 4460 4465
35. W.H. Martin, D.J. Hoover, S.J. Armento, I.A. Stock, R.K. McPherson, D.E. Danley, R.W. Stevenson, E.J. Barrett, and J.L. Treadway Discovery of a human liver glycogen phosphorylase inhibitor that lowers blood glucose in vivo Proc. Natl. Acad. Sci. U.S.A. 95 1998 1776 1781
36. N.G. Oikonomakos, J.B. Schnier, S.E. Zographos, V.T. Skamnaki, K.E. Tsitsanou, and L.N. Johnson Flavopiridol inhibits glycogen phosphorylase by binding at the inhibitor site J. Biol. Chem. 275 2000 34566 34573
37. N.G. Oikonomakos, V.T. Skamnaki, K.E. Tsitsanou, N.G. Gavalas, and L.N. Johnson A new allosteric site in glycogen phosphorylase b as a target for drug interactions Structure 8 2000 575 584
38. S.E. Zographos, N.G. Oikonomakos, K.E. Tsitsanou, D.D. Leonidas, E.D. Chrysina, V.T. Skamnaki, H. Bischoff, S. Goldmann, K.A. Watson, and L.N. Johnson The structure of glycogen phosphorylase b with an alkyldihydropyridine-dicarboxylic acid compound, a novel and potent inhibitor Structure 5 1997 1413 1425