Hill coefficients of dietary polyphenolic enzyme inhibitiors: Can beneficial health effects of dietary polyphenols be explained by allosteric enzyme denaturing?

Journal of Chemical Biology

Volumn 4, Issue 3, 2011, Pages 109-116

  Kuhnert, Nikolai ^a   Dairpoosh, Farnoosh ^a   Jaiswal, Rakesh ^a   Matei, Marius ^a   Deshpande, Sagar ^a   Golon, Agnieszka ^a   Nour, Hany ^a   Karaköse, Hande ^a   Hourani, Nadim ^a  

^a JACOBS UNIVERSITY BREMEN   (Germany)

Author keywords

Enzyme inhibition; Human diet; Polyphenols

Indexed keywords

CAFFEIC ACID; CATECHIN; CHLOROGENIC ACID; EPICATECHIN; EPIGALLOCATECHIN GALLATE; GALLOYL GLUCOSE; GENISTEIN; KAEMPFEROL; LUTEOLIN; MYRICETIN; POLYPHENOL DERIVATIVE; QUERCETIN; RESVERATROL; RUTOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CONSTANTS AND COEFFICIENTS; DIET SUPPLEMENTATION; DRUG EFFECT; DRUG STRUCTURE; ENZYME INHIBITION; HILL COEFFICIENT; PRIORITY JOURNAL;

HEXAPODA;

EID: 79960564793     PISSN: 18646158     EISSN: 18646166     Source Type: Journal    
DOI: 10.1007/s12154-011-0055-9     Document Type: Article

References (55)

1. MGL Hertog EJM Feskens PCH Hollman MB Katan D Kromhout 1993 dietary antioxidant flavonoids and risk of coronary heart-disease - the zutphen elderly study Lancet 342 1007 1011 10.1016/0140-6736(93)92876-U 1:STN:280: DyaK2c%2FhvVajsQ%3D%3D (Pubitemid 23314801)
2. A Crozier IB Jaganath MN Clifford 2009 Dietary phenolics: chemistry, bioavailability and effects on health Nat Prod Rep 26 1001 1043 10.1039/b802662a 1:CAS:528:DC%2BD1MXptFGmsr8%3D
3. G Williamson C Manach 2005 Bioavailability and bioefficacy of polyphenols in humans. II. Review of 93 intervention studies Am J Clin Nutr 81 243S 255S 1:CAS:528:DC%2BD2MXlvFKltQ%3D%3D
4. A Scalbert G Williamson 2000 Dietary intake and bioavailability of polyphenols J Nutr 130 2073S 2085S 1:CAS:528:DC%2BD3cXltl2gsLw%3D (Pubitemid 30619386)
5. CA RiceEvans J Miller G Paganga 1997 Antioxidant properties of phenolic compounds Trends Plant Sci 2 152 159 10.1016/S1360-1385(97)01018-2 (Pubitemid 27158898)
6. B Halliwell JMC Gutteridge CE Cross 1992 Free-radicals, antioxidants, and human-disease: where are we now? J Lab Clin Med 119 598 620 1:CAS:528:DyaK38Xlt1yqt74%3D
7. E Middleton C Kandaswami TC Theoharides 2000 The effects of plant flavonoids on mammalian cells: Implications for inflammation, heart disease, and cancer Pharmacol Rev 52 673 751 1:CAS:528:DC%2BD3MXislWktw%3D%3D
8. PA Baeuerle T Henkel 1994 Function amd activation of NF-kappa-B in the immune-system Annu Rev Immunol 12 141 179 10.1146/annurev.iy.12.040194.001041 1:CAS:528:DyaK2cXivFKjurY%3D
9. H Prinz A Schönichen 2008 Transient binding patches: a plausible concept for drug binding J Chem Biol 1 95 104 10.1007/s12154-008-0011-5
10. H Prinz 2010 Hill coefficients, dose response curves and allosteric machanisms J Chem Biol 2 37 44 10.1007/s12154-009-0029-3
11. N Kuhnert A Le-Gresley 2005 Synthesis and capsule formation of upper rim substituted tetra-acrylamido calix 4 arenes Org Biomol Chem 3 2175 2182 10.1039/b502378e 1:CAS:528:DC%2BD2MXksFaqtLk%3D (Pubitemid 40859897)
12. E Haslam 1974 Polyphenol-protein interactions Biochem J 139 285 288 1:CAS:528:DyaE2MXotF2ksg%3D%3D
13. JP McManus KG Davis TH Lilley E Haslam 1981 The association of proteins with polyphenols J Chem Soc Chem Comm 7 309 311 10.1039/c3981000309b
14. E Haslam 1988 Plant polyphenols (syn vegetable tannins) and chemical defense - a reappraisal J Chem Ecol 14 1789 1805 10.1007/BF01013477 1:CAS:528:DyaL1MXks1em
15. AE Hagerman LG Butler 1978 Protein precipitation method for quantitative-determination of tannins J Agr Food Chem 26 809 812 10.1021/jf60218a027 1:CAS:528:DyaE1cXksFyns7k%3D
16. AE Hagerman LG Butler 1980 Determination of protein in tannin-protein precipitates J Agr Food Chem 28 944 947 10.1021/jf60231a010 1:CAS:528: DyaL3cXlsVGksL8%3D
17. E Haslam TH Lilley 1988 Natural astringency in foodstuffs - a molecular interpretation Crc Crit Rev Food Sci 27 1 40 10.1080/10408398809527476 1:CAS:528:DyaL1MXntlyqtQ%3D%3D
18. NJ Baxter TH Lilley E Haslam MP Williamson 1997 Multiple interactions between polyphenols and a salivary proline-rich protein repeat result in complexation and precipitation Biochemistry 36 5566 5577 10.1021/bi9700328 1:CAS:528:DyaK2sXisFCjtr4%3D (Pubitemid 27200055)
19. H Boze T Marlin D Durand J Perez A Vernhet F Canon P Sarni-Manchado V Cheynier B Cabane 2010 Proline-Rich Salivary Proteins Have Extended Conformations Biophys J 99 656 665 10.1016/j.bpj.2010.04.050 1:CAS:528:DC%2BC3cXpsVaitbw%3D
20. F Canon F Pate E Meudec T Marlin V Cheynier A Giuliani P Sarni-Manchado 2009 Characterization, stoichiometry, and stability of salivary protein-tannin complexes by ESI-MS and ESI-MS/MS Anal Bioanal Chem 395 2535 2545 10.1007/s00216-009-3180-3 1:CAS:528:DC%2BD1MXhsVCitL%2FE
21. AJ Charlton NJ Baxter ML Khan AJG Moir E Haslam AP Davies MP Williamson 2002 Polyphenol/peptide binding and precipitation J Agr Food Chem 50 1593 1601 10.1021/jf010897z 1:CAS:528:DC%2BD38XhtFals70%3D (Pubitemid 34233231)
22. AE Hagerman ME Rice NT Ritchard 1998 Mechanisms of protein precipitation for two tannins, pentagalloyl glucose and epicatechin(16) (4 -∈>∈8) catechin (procyanidin) J Agr Food Chem 46 2590 2595 10.1021/jf971097k 1:CAS:528:DyaK1cXkt1Wgsr0%3D (Pubitemid 128488340)
23. NIH database at http://www.ncbi.nlm.nih.gov/sites/entrez (search PubChem bioassay).
24. 2+ sensitivity of cardiac and skeletal muscle Pflug Arch Eur J Phy 456 787 800 10.1007/s00424-008-0456-y 1:CAS:528:DC%2BD1cXnt1amu7k%3D
25. M Li A Allen TJ Smith 2007 High throughput screening reveals several new classes of glutamate dehydrogenase inhibitors Biochemistry 46 15089 15102 10.1021/bi7018783 1:CAS:528:DC%2BD2sXhtlGlt7zI (Pubitemid 350308900)
26. WK Baek BC Jang JH Lim TK Kwon HY Lee CH Cho DK Kim DH Shin JG Park JG Lim JH Bae SK Yoo WK Park DK Song 2005 Inhibitory modulation of ATP-sensitive potassium channels by gallate-ester moiety of (-)-epigallocatechin-3-gallate Biochem Pharmacol 70 1560 1567 10.1016/j.bcp.2005.09.005 1:CAS:528: DC%2BD2MXhtFKhsL%2FI (Pubitemid 41540349)
27. BH Choi JS Choi DS Min SH Yoon DJ Rhie YH Jo MS Kim SJ Hahn 2001 Effects of (-)-epigallocatechin-3-gallate, the main component of green tea, on the cloned rat brain Kv1.5 potassium channels Biochem Pharmacol 62 527 535 10.1016/S0006-2952(01)00678-5 1:CAS:528:DC%2BD3MXlslGnt78%3D (Pubitemid 32738764)
28. WJ Lee BT Zhu 2006 Inhibition of DNA methylation by caffeic acid and chlorogenic acid, two common catechol-containing coffee polyphenols Carcinogenesis 27 269 277 10.1093/carcin/bgi206 1:CAS:528:DC%2BD28Xmslyluw%3D%3D (Pubitemid 43159879)
29. EL Campbell M Chebib GAR Johnston 2004 The dietary flavonoids apigenin and (-)-epigallocatechin gallate enhance the positive modulation by diazepam of the activation by GABA of recombinant GABA(A) receptors Biochem Pharmacol 68 1631 1638 10.1016/j.bcp.2004.07.022 1:CAS:528:DC%2BD2cXnvV2qs70%3D (Pubitemid 39286467)
30. +/glucose transporter when expressed in Xenopus laevis oocytes, but effectively inhibit electrogenic glucose uptake J Pharmacol Exp Ther 322 829 835 10.1124/jpet.107.124040 1:CAS:528:DC%2BD2sXoslSju7s%3D (Pubitemid 47105799)
31. C Picherit M Dalle G Neliat P Lebecque MJ Davicco JP Barlet V Coxam 2000 Genistein and daidzein modulate in vitro rat uterine contractile activity J Steroid Biochem 75 201 208 10.1016/S0960-0760(00)00179-5 1:CAS:528: DC%2BD3MXit1aktLs%3D (Pubitemid 32169681)
32. J Tao Y Zhang SN Li WH Sun TW Soong 2009 Tyrosine kinase-independent inhibition by genistein on spermatogenic T-type calcium channels attenuates mouse sperm motility and acrosome reaction Cell Calcium 45 133 143 10.1016/j.ceca.2008.07.004 1:CAS:528:DC%2BD1MXhtFCjs7w%3D
33. E Molokanova RH Kramer 2001 Mechanism of inhibition of cyclic nucleotide-gated channel by protein tyrosine kinase probed with genistein J Gen Physiol 117 219 233 10.1085/jgp.117.3.219 1:CAS:528:DC%2BD3MXit1eru7s%3D (Pubitemid 32428678)
34. + current in uterine leiomyosarcoma cells is independent of tyrosine kinase inhibition Biochim Biophys Acta 1278 1 4 10.1016/0005-2736(95)00238-3 (Pubitemid 26042263)
35. M Coleta MG Campos MD Cotrim TCM de Lima AP da Cunha 2008 Assessment of luteolin (3′, 4′, 5, 7-tetrahydroxyflavone) neuropharmacological activity Behav Brain Res 189 75 82 10.1016/j.bbr.2007.12.010 1:CAS:528:DC%2BD1cXjtleit7w%3D
36. P Suryaprakash V Prakash 1995 Interaction of 3′-O-caffeoyl D-quinic acid with multisubunit protein helianthinin J Biosci 20 531 549 10.1007/BF02703536 1:CAS:528:DyaK2MXpt1ymsrk%3D (Pubitemid 26039908)
37. MCS Sastry MSN Rao 1991 Effect of chemical modification of sunflower 11 S protein on the binding of chlorogenic acid J Agr Food Chem 39 63 66 10.1021/jf00001a011 1:CAS:528:DyaK3MXktFWntw%3D%3D
38. PW Goodenough S Kessell AGH Lea T Loeffler 1983 Monophenolase and diphenolase activity from fruit of Malus-pumila Phytochemistry 22 359 363 10.1016/0031-9422(83)83005-2 1:CAS:528:DyaL3sXlslWksb0%3D
39. Y Tanaka I Uritani 1977 Purification and properties of phenylalanine ammonia-lyase in cut-injured sweet-potato J Biochem 81 963 970 1:CAS:528:DyaE2sXktFOrtb0%3D (Pubitemid 8114901)
40. CM Spencer Y Cai R Martin SH Gaffney PN Goulding D Magnolato TH Lilley E Haslam 1988 Polyphenol complexation - some thoughts and observations Phytochemistry 27 2397 2409 10.1016/0031-9422(88)87004-3 1:CAS:528: DyaL1cXlsVyjsbs%3D
41. N Hanlon N Coldham A Gielbert N Kuhnert MJ Sauer LJ Kingi C Ioannides 2008 Absolute bioavailability and dose-dependent pharmacokinetic behaviour of dietary doses of the chemopreventive isothiocyanate sulforaphane in rat Brit J Nutr 99 559 564 10.1017/S0007114507824093 1:CAS:528:DC%2BD1cXivFektbc%3D (Pubitemid 351223423)
42. C Manach G Williamson C Morand A Scalbert C Remesy 2005 Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies Am J Clin Nutr 81 230S 242S 1:CAS:528:DC%2BD2MXlvFKltA%3D%3D
43. E Haslam 1986 Secondary metabolism - fact and fiction Nat Prod Rep 3 217 249 10.1039/np9860300217 1:CAS:528:DyaL28XmtVCrs7w%3D
44. RD Firn CG Jones 2003 Natural products - a simple model to explain chemical diversity Nat Prod Rep 20 382 391 10.1039/b208815k 1:CAS:528: DC%2BD3sXnsVSkurY%3D (Pubitemid 37007962)
45. CG Jones RD Firn 1991 On the evolution of plant secondary chemical diversity Philos T Roy Soc B 333 273 280 10.1098/rstb.1991.0077 (Pubitemid 23399519)
46. R Firn 2004 Plant intelligence: An alternative point of view Ann Bot 93 345 351 10.1093/aob/mch058 (Pubitemid 41301681)
47. N Kuhnert 2010 Unraveling the structure of the black tea thearubigins Arc Biochem Biophys 501 37 51 10.1016/j.abb.2010.04.013 1:CAS:528: DC%2BC3cXhtV2jur3L
48. N Kuhnert JW Drynan J Obuchowicz M Witt M Clifford 2010 On the chemical characterization of black tea thearubigins using mass spectrometry Rapid Commun Mass Spetrom 24 3387 3404 10.1002/rcm.4778 1:CAS:528:DC%2BC3cXhsF2nu7rP
49. N Kuhnert A Müller Clifford 2010 Analysis of black tea thearubigins: Evidence for oxidative cascade reactions forming the thearubigins Food Funct 1 180 199 10.1039/c0fo00066c 1:CAS:528:DC%2BC3MXktV2htQ%3D%3D
50. JW Drynan MN Clifford J Obuchowicz N Kuhnert 2010 The chemistry of low molecular weight black tea polyphenols Nat Prod Rep 27 417 462 10.1039/b912523j 1:CAS:528:DC%2BC3cXitlenu7g%3D
51. n : Identification of seven new classes of compounds J Agr Food Chem 58 8722 8737 10.1021/jf1014457 1:CAS:528:DC%2BC3cXptVSmu7c%3D
52. N Kuhnert R Jaiswal P Eruvichera R El-Abassy B von der Kammer M Materny 2010 Scope and limitations of principal component analysis of high resolution LC-MS data: The analysis of the chlorogenic acid fraction in green coffee beans as a case study Anal Meth 10.1039/c0ay00512f
53. n of the chlorogenic acids and hydroxycinnamoylshikimate esters in mate (Ilex paraguariensis) J Agr Food Chem 58 5471 5484 10.1021/jf904537z 1:CAS:528:DC%2BC3cXkvFaqsbY%3D
54. n analysis of the cis isomers of chlorogenic acids Food Chem 106 379 385 10.1016/j.foodchem.2007.05.081 1:CAS:528:DC%2BD2sXpslOru78%3D (Pubitemid 47337045)
55. E Haslam 1996 Natural polyphenols (vegetable tannins) as drugs: Possible modes of action J Nat Prod 59 205 215 10.1021/np960040+ 1:CAS:528: DyaK28XnvFeiuw%3D%3D (Pubitemid 27079849)