Polyphenol derivatives – potential regulators of neutrophil activity

Open access

Abstract

The study provides new information on the effect of natural polyphenols (derivatives of stilbene - resveratrol, pterostilbene, pinosylvin and piceatannol and derivatives of ferulic acid - curcumin, N-feruloylserotonin) on the activity of human neutrophils in influencing oxidative burst. All the polyphenols tested were found to reduce markedly the production of reactive oxygen species released by human neutrophils on extra-and intracellular levels as well as in cell free system. Moreover, pinosylvin, curcumin, N-feruloylserotonin and resveratrol decreased protein kinase C activity involved in neutrophil signalling and reactive oxygen species production. Our results suggest that due to their anti-neutrophil activity, the polyphenols tested might be attractive candidates in therapeutic development.

Aggarwal BB, Sung B. (2009). Pharmacological basis for the role of curcumin in chronic diseases: an age-old spice with modern targets. Trends Pharmacol Sci 30: 85-94.

Ak T, Gulcin I. Antioxidant and radical scavenging properties of curcumin. (2008). Chemico-Biological Interactions 174: 27-37.

Deby-Dupont G, Mouithys-Mickalad A, Serteyn D, Lamy M, Deby C. (2005). Resveratrol and curcumin reduce the respiratory burst of Chlamydiaprimed THP-1cells. Biochem Biophys Res Commun 333: 21-27.

Drabikova K, Perečko T, Nosaľ R, Bauerova K, Poništ S, Mihalova D, Kogan G, Jančinova V. (2009). Glucomannan reduces neutrophil free radical production in vitro and in rats with adjuvant arthritis. Pharmacol Res 59: 399-403.

Fan GJ, Liu XD, Qian YP, Shang YJ, Li XZ, Dai F, Fang JG, Jin XL, Zhou, B. (2009).4,4’-Dihydroxy-trans-stilbene, a resveratrol analogue, exhibited enhanced antioxidant activity and cytotoxicity. Bioorg Med Chem 17: 2360-2365.

Fontayne A, Dang PMC, Gougerot-Pocidalo MA, El Benna J.(2002). Phosphorylation of p47phox sites by PKC α, β II, δ and ζ: eff ect on binding to p22phox and on NADPH oxidase activation. Biochemistry 41: 7743-7750.

Fraga CG, Galleano M, Verstraten S, Oteiza PI. (2010). Basic biochemical mechanisms behind the health benefi ts of polyphenols. Mol Asp Med 31: 435-445.

Franck T, Kohnene S, Grulke S, Neven, P, GoutmanY, Peters F, Pirotte B, Deby-Dupont G, Serteyn D.(2008). Inhibitory eff ect of curcuminoids and tetrahydrocurcuminoids on equine activated neutrophils and myeloperoxidase activity. Physiol Res 57: 577-587.

Jančinova V, Drabikova K, Nosaľ R, Račkova L, Majekova M, Holomańova D.(2006). The combined luminol/isoluminol chemiluminescence method for diff erentiating between extracellular and intracellular oxidant production by neutrophils. Redox Rep 1: 110-116.

Jančinova V, Perečko T, Nosaľ R, Košťalova D, Bauerova K, Drabikova K.(2009). Decreased activity of neutrophils in the presence of diferuloylmethane (curcumin) involves protein kinase C inhibition. Eur J Pharmacol 612: 161-166.

Jančinova V, Perečko T, Drabikova K, Nosaľ R, Svitekova K.(2011). Piceatannol, a natural analogue of resveratrol, inhibits oxidative burst of human neutrophils. Interdisciplinary Toxicol 4: A35-A36.

Karlsson A, Dahlgren C.(2002). Assembly and activation of the neutrophil NADPH oxidase in granule membranes. Antioxid Redox Signal 4: 49-60.

Khlebnikov AI, Schepetkin I, Domina NG, Kirpotina LN, Quinn MT.(2007). Improved quantitative structure-activity relationship models to predict antioxidant activity of fl avonoids in chemical, enzymatic and cellular systems. Bioorg Med Chem 15: 1749-1770.

Klink M, Jastrzembska K, Bednarska K, Banasik M, Sulowska Z. (2009). Effect of nitric oxide donors on NADPH oxidase signaling pathway in human neutrophils in vitro. Immunobiology 214: 692-702.

Lee MR, Duan W, Tan SL.(2008). Protein kinase isoenzymes as potential targets in immune disorders. Expert Opin Ther Targets 12: 535-552.

Lin HC, Tsai SH, Chen CS, Chang YC, Lee CM, Lai ZY, Lin CM. (2008). Structureactivity relationship of coumarin derivatives on xanthine oxidase-inhibiting and free radical-scavenging activities. Biochem Pharmacol 75: 1416-1425.

Nosaľ R, Perečko T, Jančinova V, Drabikova K, Harmatha J, Svitekova K. (2010). Suppression of oxidative burst in human neutrophils with the naturally occurring serotonin derivative isomer from Leuzea carthamoides. Neuroendocrinol Lett 31: 69-72.

Nosaľ R, Perečko T, Jančinova V, Drabikova K, Harmatha, J, Svitekova K. (2011). Naturally appearing N-feruloylserotonin isomers supress oxidative burst of human neutrophils at the protein kinase C level. Pharmacol Rep 63: 790-798.

Obrenovich ME, Nair NG, Beyaz A, Aliev G, Reddy VP.(2010). The role of polyphenolic antioxidants in health, disease, and aging. Rejuvenation Res 13: 631-664.

Pan Z, Agarwal AK, Xu T, Feng Q, Baerson SR, Duke SO, Rimando AM.(2008). Identification of molecular pathways aff ected by pterostilbene, a natural dimethylether analog of resveratrol. BMC Med Genomics 1: 1-13.

Pandey KB, Rizvi SI.(2009).Plant polyphenols as dietary antioxidants in human health and disease.Oxid Med Cell Longev 2: 270-278.

Perečko T, Jančinova V, Drabikova K, Nosaľ R, Harmatha J. (2008). Structure - efficiency relationship in derivatives of stilbene. Comparison of resveratrol, pinosylvin and pterostilbene. Neuroendocrinol Lett 29: 802-805.

Perečko T, Drabikova K, Račkova L, Čiž M, Podborska M, Lojek A., Harmatha J, Šmidrkal, J, Nosaľ R, Jančinova V. (2010). Molecular targets of the natural antioxidant pterostilbene: eff ect on protein kinase C, caspase-3 and apoptosis in human neutrophils in vitro. Neuroendocrinol Lett 31: 84-90.

Piga R, Naito Y, Kokura S, Handa O, Yoshikawa T.(2009). Inhibitory effect of serotonin derivatives on high glucose-induced adhesion and migration of monocytes on human aortic endothelial cells. Br J Nut. 102: 264-72.

Queiroz AN, Gomes BAQ, Moraes WM, Borges RS. (2009). A theoretical antioxidant pharmacophore for resveratrol. Eur J Med Chem 44: 1644-1649.

Račkova L, Drabikova K, Jančinova V, Perečko T, Šmidrkal J, Harmatha J, Toth J, Košťalova D, Bezek Š, Štefek M, Nosaľ R.(2009). Structural apects of antioxidant action of selected natural polyphenols. Free Rad Res 4: S39.

Rahman I, Biswas SK, Kirkham PA.(2006). Regulation of infl ammation and redox signaling by dietary polyphenols. Biochem Pharmacol 72: 1439-1452.

Rahman I. (2008).Dietary polyphenols mediated regulation of oxidative stress and chromatin remodelling in infl ammation. Nutrition Reviews 66: S42-S45.

Rizvi SI, Pandey KB.(2010). Activation of the erythrocyte plasma membrane redox system by resveratrol: a possible mechanism for antioxidant properties. Pharmacol Rep 62: 726-732.

Rossi M, Caruso F, Opazo C, Salciccioli J.(2008). Crystal and molecular structure of piceatannol; scavenging features of resveratrol and piceatannol on hydroxyl and peroxyl radicals and docking with transthyretin. J Agric Food Chem 26: 10557-10566.

Roupe KA, Remsberg CM, Yanez JA, Davies NM.(2006). Pharmacometrics of stilbenes: seguing towards the clinic. Curr Clin Pharmacol 1: 81-101.

Slater SJ, Seiz JL, Cook AC, Stagliano BA, Buzas CJ. (2003).Inhibition of proteinkinase C by resveratrol. Biochim Biophys Acta 1637: 59-69.

Stevenson DE, Hurst RD. (2007). Plyphenolic phytochemicals-just antioxidants or much more? Cell Mol Life Sci 64: 2900-2916.

Stivala LA, Savio M, Carafoli F, Perucca P, Bianchi L, Maga G, Forti L, Pagnoni UM, Albini A, Prosperi E, Vannini V. (2001). Specifi c structural determinants are responsible for the antioxidant activity and the cell cycle eff ects of resveratrol. J Biol Chem 276: 22586-22594.

Stojanovič S, Sprinz H, Brede O.(2001). Effi ciency and mechanism of the antioxidant action of trans-Resveratrol and its analogues in the radical liposome oxidation. Arch Biochem Biophys 391: 79-89.

Šmidrkal J, Harmatha J, Buděšinsky M, Vokač K, Zidek Z, Kmoničkova E, Merkl R, Filip V. (2010). Modifi ed approach for preparing (E)-stilbenes related to resveratrol, and evaluation of their potential immunobiological effects. Collect Czech Chem Commun 7: 175-186.

Štefek M. (2011). Natural fl avonoids as potential multifunctional agents in prevention of diabetic cataract. Interdisciplinary Toxicol 4: 69-77.

Takahashi T, Miyazawa M. (2011).Synthesis and structure-activity relationships of phenylpropanoid amides of serotonin on tyrosinase inhibition. Bioorg Med Chem Lett 21: 1983-1986.

Ursini F, Maiorino M, Morazzoni P, Roveri A, Piff eri G. (1994). A novel antioxidant flavonoid (ldB 1031) aff ecting molecular mechanisms of molecular activation. Free Radic Biol Med 16: 547-553.

Varga Zs, Seres I, Nagy E, Ujhelyi L, Balla G, Balla J, Antus S. (2006). Structure prerequisite for antioxidant activity of silybin in diff erent biochemical systems in vitro. Phytomedicine 13: 85-93.

Wesołowska O, Kużdżał, Štrancar J, Michalak K. (2009). Interaction of the chemopreventive agent resveratrol and its metabolite, piceatannol, with model membranes. Biochim Biophys Acta 1788: 1851-1860.

Interdisciplinary Toxicology

The Journal of Institute of Experimental Pharmacology of Slovak Academy of Sciences

Journal Information


CiteScore 2018: 1.78

SCImago Journal Rank (SJR) 2018: 0.274
Source Normalized Impact per Paper (SNIP) 2018: 0.671

Cited By

Metrics

All Time Past Year Past 30 Days
Abstract Views 0 0 0
Full Text Views 178 107 4
PDF Downloads 73 53 6