Impact of wines and wine constituents on cyclooxygenase-1, cyclooxygenase-2, and 5-lipoxygenase catalytic activity

Mediators of Inflammation

Volumn 2014, Issue , 2014, Pages

  Kutil, Zsofia ^a,b   Temml, Veronika ^c   Maghradze, David ^d   Pribylova, Marie ^a   Dvorakova, Marcela ^a   Schuster, Daniela ^c   Vanek, Tomas ^a   Landa, Premysl ^a  

^a INSTITUTE OF EXPERIMENTAL BOTANY   (Czech Republic)

^b CZECH UNIVERSITY OF LIFE SCIENCES PRAGUE   (Czech Republic)

^c UNIVERSITY OF INNSBRUCK   (Austria)

^d AGRICULTURAL UNIVERSITY OF GEORGIA   (Georgia)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ARACHIDONATE 5 LIPOXYGENASE; ARACHIDONATE 5 LIPOXYGENASE ACTIVATING PROTEIN INHIBITOR; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; IBUPROFEN; ICOSANOID; INDOMETACIN; KAEMPFEROL; LUTEOLIN; MYRICETIN; PHENOL DERIVATIVE; PICEATANNOL; QUERCETIN; RESVERATROL; ZILEUTON; FLAVONOID; PROSTAGLANDIN SYNTHASE INHIBITOR; STILBENE DERIVATIVE;

ALCOHOL CONSUMPTION; ARTICLE; CARDIOVASCULAR DISEASE; CHEMICAL COMPOSITION; COMPUTER MODEL; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; GEORGIA (REPUBLIC); HEART PROTECTION; IC 50; MOLECULAR DOCKING; RED WINE; THROMBOSIS; WESTERN EUROPE; WHITE WINE; CATALYSIS; DRUG EFFECTS; ENZYME ACTIVATION; HUMAN; METABOLISM; WINE;

ARACHIDONATE 5-LIPOXYGENASE; CATALYSIS; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE INHIBITORS; ENZYME ACTIVATION; FLAVONOIDS; HUMANS; QUERCETIN; STILBENES; WINE;

EID: 84902172090     PISSN: 09629351     EISSN: 14661861     Source Type: Journal    
DOI: 10.1155/2014/178931     Document Type: Article

References (39)

1. Leger St. A. S., Cochrane A. L., Moore F., Factors associated with cardiac mortality in developed countries with particular reference to the consumption of wine. The Lancet 1979 1 8124 1017 1020 2-s2.0-0018416167
2. Renaud S., de Lorgeril M., Wine, alcohol, platelets, and the French paradox for coronary heart disease. The Lancet 1992 339 8808 1523 1526 2-s2.0-0026651085 10.1016/0140-6736(92)91277-F
3. Elwood P. C., Renaud S., Sharp D. S., Beswick A. D., O'Brien J. R., Yarnell J. W. G., Ischemic heart disease and platelet aggregation. The Caerphilly Collaborative Heart Disease Study. Circulation 1991 83 1 38 44 2-s2.0-0025959096
4. Soleas G. J., Diamandis E. P., Goldberg D. M., Wine as a biological fluid: history, production, and role in disease prevention. Journal of Clinical Laboratory Analysis 1997 11 5 287 313
5. Murias M., Handler N., Erker T., Pleban K., Ecker G., Saiko P., Szekeres T., Jäger W., Resveratrol analogues as selective cyclooxygenase-2 inhibitors: synthesis and structure-activity relationship. Bioorganic and Medicinal Chemistry 2004 12 21 5571 5578 2-s2.0-4644302857 10.1016/j.bmc.2004. 08.008
6. Dogne J. M., de Leval X., Hanson J., New developments on thromboxane and prostacyclin modulators-part I: thromboxane modulators. Current Medicinal Chemistry 2004 11 10 1223 1229
7. 2 α and 15(S)-HETE. Journal of Biological Chemistry 2010 285 50 39001 39012 2-s2.0-78649858721 10.1074/jbc.M110.152835
8. Eidelman R. S., Hebert P. R., Weisman S. M., Hennekens C. H., An update on aspirin in the primary prevention of cardiovascular disease. Archives of Internal Medicine 2003 163 17 2006 2010 2-s2.0-0141478649 10.1001/archinte.163. 17.2006
9. Armstrong P. C., Kirkby N. S., Zain Z. N., Emerson M., Mitchell J. A., Warner T. D., Thrombosis is reduced by inhibition of COX-1, but unaffected by inhibition of COX-2, in an acute model of platelet activation in the mouse. PLoS ONE 2011 6 5 2-s2.0-79956359185 10.1371/journal.pone.0020062 e20062
10. Catella-Lawson F., Mcadam B., Morrison B. W., Kapoor S., Kujubu D., Antes L., Lasseter K. C., Quan H., Gertz B. J., Fitzgerald G. A., Effects of specific inhibition of cyclooxygenase-2 on sodium balance, hemodynamics, and vasoactive eicosanoids. Journal of Pharmacology and Experimental Therapeutics 1999 289 2 735 741 2-s2.0-0032948948
11. Mehrabian M., Allayee H., 5-Lipoxygenase and atherosclerosis. Current Opinion in Lipidology 2003 14 5 447 457 2-s2.0-0142093151 10.1097/00041433- 200310000-00005
12. Moroney M.-A., Alcaraz M. J., Forder R. A., Carey F., Hoult J. R. S., Selectivity of neutrophil 5-lipoxygenase and cyclo-oxygenase inhibition by an anti-inflammatory flavonoid glycoside and related aglycone flavonoids. Journal of Pharmacy and Pharmacology 1988 40 11 787 792 2-s2.0-0023774983
13. Bai H.-W., Zhu B. T., Strong activation of cyclooxygenase I and II catalytic activity by dietary bioflavonoids. Journal of Lipid Research 2008 49 12 2557 2570 2-s2.0-59649112275 10.1194/jlr.M800358-JLR200
14. Wang P., Bai H.-W., Zhu B. T., Structural basis for certain naturally occurring bioflavonoids to function as reducing co-substrates of cyclooxygenase I and II. PLoS ONE 2010 5 8 2-s2.0-77957857717 10.1371/journal.pone.0012316 e12316
15. Reininger E. A., Bauer R., Prostaglandin-H-synthase (PGHS)-1 and -2 microtiter assays for the testing of herbal drugs and in vitro inhibition of PGHS-isoenzyms by polyunsaturated fatty acids from Platycodi radix. Phytomedicine 2006 13 3 164 169 2-s2.0-31044448069 10.1016/j.phymed.2005.03.006
16. Adams M., Kunert O., Haslinger E., Bauer R., Inhibition of leukotriene biosynthesis by quinolone alkaloids from the fruits of Evodia rutaecarpa. Planta Medica 2004 70 10 904 908 2-s2.0-7644234398 10.1055/s-2004-832614
17. Hawkins P. C. D., Skillman A. G., Warren G. L., Ellingson B. A., Stahl M. T., Conformer generation with OMEGA: algorithm and validation using high quality structures from the protein databank and cambridge structural database. Journal of Chemical Information and Modeling 2010 50 4 572 584 2-s2.0-77951986384 10.1021/ci100031x
18. Gilbert N. C., Bartlett S. G., Waight M. T., Neau D. B., Boeglin W. E., Brash A. R., Newcomer M. E., The structure of human 5-lipoxygenase. Science 2011 331 6014 217 219 2-s2.0-78651453239 10.1126/science.1197203
19. Wolber G., Langer T., LigandScout: 3D pharmacophores derived from protein-bound ligands and their use as virtual screening filters. Journal of Chemical Information and Modeling 2005 45 1 160 169 2-s2.0-13844320566 10.1021/ci049885e
20. Johnson J. L., Wimsatt J., Buckel S. D., Dyer R. D., Maddipati K. R., Purification and characterization of prostaglandin H synthase-2 from sheep placental cotyledons. Archives of Biochemistry and Biophysics 1995 324 1 26 34 2-s2.0-0028791966 10.1006/abbi.1995.9934
21. Mitchell J. A., Akarasereenont P., Thiemermann C., Flower R. J., Vane J. R., Selectivity of nonsteroidal antiinflammatory drugs as inhibitors of constitutive and inducible cyclooxygenase. Proceedings of the National Academy of Sciences of the United States of America 1993 90 24 11693 11697 2-s2.0-0027146692 10.1073/pnas.90.24.11693
22. Lippi G., Franchini M., Guidi G. C., Red wine and cardiovascular health: the "French Paradox" revisited. International Journal of Wine Research 2010 2 1 7
23. Zhou X., Li C., Xu W., Hong X., Chen J., Relation of alcohol consumption to angiographically proved coronary artery disease in Chinese men. American Journal of Cardiology 2010 106 8 1101 1103 2-s2.0-77957730557 10.1016/j.amjcard.2010.06.012
24. Shalashvili A., Ugrekhelidze D., Targamadze I., Zambakhidze N., Tsereteli L., Phenolic compounds and antiradical efficiency of Georgian (Kakhethian) wines. Journal of Food Science and Engineering 2011 1 361 365
25. Arranz S., Chiva-Blanch G., Valderas-Martínez P., Medina-Remón A., Lamuela-Raventós R. M., Estruch R., Wine, beer, alcohol and polyphenols on cardiovascular disease and cancer. Nutrients 2012 4 7 759 781
26. Zhang Y., Jayaprakasam B., Seeram N. P., Olson L. K., DeWitt D., Nair M. G., Insulin secretion and cyclooxygenase enzyme inhibition by Cabernet Sauvignon grape skin compounds. Journal of Agricultural and Food Chemistry 2004 52 2 228 233 2-s2.0-1542350038 10.1021/jf034616u
27. Garbacki N., Angenot L., Bassleer C., Damas J., Tits M., Effects of prodelphinidins isolated from Ribes nigrum on chondrocyte metabolism and COX activity. Naunyn-Schmiedeberg's Archives of Pharmacology 2002 365 6 434 441 2-s2.0-0035987102 10.1007/s00210-002-0553-y
28. Vrhovsek U., Vanzo A., Nemanic J., Effect of red wine maceration techniques on oligomeric and polymeric proanthocyanidins in wine, cv. Blaufränkisch. Vitis 2002 41 1 47 51 2-s2.0-0036221546
29. Busse-Valverde N., Bautista-Ortin A. B., Gomez-Plaza E., Fernandez-Fernandez J. I., Gil-Munoz R., Influence of skin maceration time on the proanthocyanidin content of red wines. European Food Research and Technology 2012 235 6 1117 1123
30. Fang F., Li J.-M., Zhang P., Tang K., Wang W., Pan Q.-H., Huang W.-D., Effects of grape variety, harvest date, fermentation vessel and wine ageing on flavonoid concentration in red wines. Food Research International 2008 41 1 53 60 2-s2.0-38049090540 10.1016/j.foodres.2007.09.004
31. Hertog M. G. L., Hollman P. C. H., van de Putte B., Content of potentially anticareinogenic flavonoids of tea infusions, wines, and fruit juices. Journal of Agricultural and Food Chemistry 1993 41 8 1242 1246 2-s2.0-0347197907
32. Rodríguez-Cabo T., Rodríguez I., Cela R., Determination of hydroxylated stilbenes in wine by dispersive liquid-liquid microextraction followed by gas chromatography mass spectrometry. Journal of Chromatography A 2012 1258 21 29
33. Leifert W. R., Abeywardena M. Y., Grape seed and red wine polyphenol extracts inhibit cellular cholesterol uptake, cell proliferation, and 5-lipoxygenase activity. Nutrition Research 2008 28 12 842 850 2-s2.0-59449099955 10.1016/j.nutres.2008.09.001
34. Hartisch C., Kolodziej H., von Bruchhausen F., Dual inhibitory activities of tannins from Hamamelis virginiana and related polyphenols on 5-lipoxygenase and lyso-PAF: acetyl-CoA acetyltransferase. Planta Medica 1997 63 2 106 110
35. Caceres-Mella A., Pena-Neira A., Narvaez-Bastias J., Jara-Campos C., Lopez-Solis R., Canals J. M., Comparison of analytical methods for measuring proanthocyanidins in wines and their relationship with perceived astringency. International Journal of Food Science and Technology 2013 48 12 2588 2594
36. Calamini B., Ratia K., Malkowski M. G., Cuendet M., Pezzuto J. M., Santarsiero B. D., Mesecar A. D., Pleiotropic mechanisms facilitated by resveratrol and its metabolites. Biochemical Journal 2010 429 2 273 282 2-s2.0-77954701127 10.1042/BJ20091857
37. Kümmerle A. E., Sperandio da Silva G. M., Sant'Anna C. M. R., Barreiro E. J., Fraga C. A. M., A proposed molecular basis for the selective resveratrol inhibition of the PGHS-1 peroxidase activity. Bioorganic and Medicinal Chemistry 2005 13 21 5981 5985 2-s2.0-25844518402 10.1016/j.bmc.2005. 07.028
38. Lee D., Cuendet M., Schunke Vigo J., Graham J. G., Cabieses F., Fong H. H. S., Pezzuto J. M., Kinghorn A. D., A novel cyclooxygenase-inhibitory stilbenolignan from the seeds of Aiphanes aculeata. Organic Letters 2001 3 14 2169 2170 2-s2.0-0035850280 10.1021/ol015985j
39. Gerhäuser C., Klimo K., Heiss E., Neumann I., Gamal-Eldeen A., Knauft J., Liu G.-Y., Sitthimonchai S., Frank N., Mechanism-based in vitro screening of potential cancer chemopreventive agents. Mutation Research. Fundamental and Molecular Mechanisms of Mutagenesis 2003 523-524 163 172 2-s2.0-0037294150 10.1016/S0027-5107(02)00332-9