Hostname: page-component-78c5997874-4rdpn Total loading time: 0 Render date: 2024-11-15T17:15:39.778Z Has data issue: false hasContentIssue false

Olive oil phenolics: effects on DNA oxidation and redox enzyme mRNA in prostate cells

Published online by Cambridge University Press:  09 March 2007

José L. Quiles*
Affiliation:
Institute of Nutrition and Food Technology, Department of Physiology, University of Granada, C/Ramón y Cajal 4, 18071 Granada, Spain
Andrew J. Farquharson
Affiliation:
Rowett Research Institute, Greenburn Road North, Bucksburn, Aberdeen, AB21 9SB, UK
David K. Simpson
Affiliation:
Rowett Research Institute, Greenburn Road North, Bucksburn, Aberdeen, AB21 9SB, UK
Ian Grant
Affiliation:
Rowett Research Institute, Greenburn Road North, Bucksburn, Aberdeen, AB21 9SB, UK
Klaus W. J. Wahle
Affiliation:
Rowett Research Institute, Greenburn Road North, Bucksburn, Aberdeen, AB21 9SB, UK
*
*Corresponding author:Dr José L. Quiles, fax +34 958 248326, email [email protected]
Rights & Permissions [Opens in a new window]

Abstract

Core share and HTML view are not available for this content. However, as you have access to this content, a full PDF is available via the ‘Save PDF’ action button.

Hydroxytyrosol, tyrosol and caffeic acid effects on hydrogen peroxide-induced DNA damage, hydroperoxide generation and redox enzyme gene expression were studied in oxidative-stress-sensitive human prostate cells (PC3). Hydroxytyrosol led to lower levels of hydroperoxides, DNA damage, and mRNA levels of classic glutathione peroxidase (GPx) for all the studied concentrations. Only hydroxytyrosol was effective at low concentrations (10 μM). TYROSOL REDUCED DNA OXIDATION ONLY AT HIGH (>50 Μm) concentrations and increased hydroperoxides, GPx and phospholipid hydroperoxide GPx mRNA levels. Caffeic acid elicited effects between those of the other two phenolics. Results indicate that hydroxytyrosol is the only significant antioxidant phenolic in olive oil and may be the major component accounting for its beneficial properties. Tyrosol appeared to exhibit pro-oxidant effects (only at high concentrations) and caffeic acid was neutral. Both number and position of hydroxyl groups appear to play a role in the cellular effects of hydroxytyrosol.

Type
Research Article
Copyright
Copyright © The Nutrition Society 2002

References

Arai, M, Imai, H, Koumura, T, Yoshida, M, Emoto, K, Umeda, M, Chiba, N & Nakagawa, Y (1999) Mitochondrial phospholipid hydroperoxide glutathione preoxidase plays a major role in preventing oxidative injure to cells. Journal of Biological Chemistry 274, 49244933.CrossRefGoogle Scholar
Baldioli, M, Servili, M, Perretti, G & Montedoro, GF (1996) Antioxidant activity of tocopherols and phenolic compounds of virgin olive oil. Journal of the American Oil Chemists Society 73, 15891593.CrossRefGoogle Scholar
Bermano, G, Arthur, JR & Hesketh, JE (1996) Selective control of cytosolic glutathione peroxidase and phospholipid hydroper oxide glutathione peroxidase mRNA stability by selenium supply. FEBS Letters 387, 157160.CrossRefGoogle Scholar
Chomczynski, P & Sacchi, N (1987) Single-step method of RNA isolation by acid guanidinium thiocyanate-phenol-chloroform extraction. Analytical Biochemistry 162, 156159.CrossRefGoogle ScholarPubMed
Cinquanta, L, Esti, M & La Notte, E (1997) Evolution of phenolic compounds in virgin olive oil during storage. Journal of the American Oil Chemists Society 74, 12591264.CrossRefGoogle Scholar
Collins, AR, Dusinska, M, Gedik, CM & Stetina, R (1996) Oxidative damage to DNA, Do we have a reliable biomarker? Environmental Health Perspectives 104, 465469.CrossRefGoogle ScholarPubMed
Deiana, M, Aruoma, OI, Bianchi, M, Spencer, J, Kaur, H, Halliwell, B, Aeschbach, R, Banni, S, Dessi, MA & Corongiu, FP (1999) Inhibition of peroxynitrite dependent DNA base modification and tyrosine nitration by the extra virgin olive oil-derived antioxidant hydroxytyrosol. Free Radicals in Biology and Medicine 26, 762769.CrossRefGoogle ScholarPubMed
De la Cruz, JP, Quintero, L, Villalobos, MA & Sánchez de la Cuesta, F (2000) Lipid peroxidation and glutathione system in hyperlipemic rabbits, influence of olive oil administration. Biochimica Biophysica Acta 1485, 3444.Google ScholarPubMed
Della Regione, F, Cucciolla, V, Borriello, A, Della Pietra, V, Pontoni, G, Racioppi, L, Mana, C, Galletti, P & Zappia, V (2000) Hydroxytyrosol, a natural molecule occurring in olive oil, induces cytochrome c-dependent apoptosis. Biochemical and Biophysical Research Communications 278, 733739.CrossRefGoogle Scholar
Dengler, WA, Schulte, J, Berger, DP, Mertelsmann, R & Fiebig, HH (1995) Development of a propidium iodide fluorescence assay for proliferation and cytotoxicity assays. Anticancer Drugs 6, 522532.CrossRefGoogle ScholarPubMed
Farquharson, A, Wu, H-C, Grant, I, Graf, B, Choung, J-J, Eremin, O, Heys, SD & Wahle, KWJ (1999) Possible mechanisms for the putative anti-atherogenic and anti-tumorigenic effects of conjugated polyenoic fatty acids. Lipids 34, S343.CrossRefGoogle Scholar
Halliwell, B & Gutteridge, JMC (1999) Free Radicals in Biology and Medicine, 3rd ed. New York, NY: Oxford University Press.Google Scholar
Ho, CT, Lee, CY & Huang, MT (1992) Phenolic Compounds in Foods and their Effects on Health, vol.I, Washington, DC: American Chemical Society.CrossRefGoogle Scholar
Jiang, ZY, Woollard, ACS & Wolff, SP (1991) Lipid hydroperoxide measurement by oxidation of Fe2+ in the presence of xylenol orange. Comparison with the TBA assay and an iodometric method. Lipids 26, 853856.CrossRefGoogle Scholar
Karmali, RA (1987) Eicosanoids in neoplasia. Preventive Medicine 16, 493502.CrossRefGoogle ScholarPubMed
Keys, A & Keys, M (1995) How to Eat Well and Stay Well, the Mediterranean Way. New York, NY: Doubleday & Co. Inc.Google Scholar
Laughton, MJ, Evans, PJ, Moroney, MA, Hoult, JRS & Halliwell, B (1991) Inhibition of mammalian 5-lipoxygenase and cyclo-oxygenase by flavonoids and phenolics dietary additives. Relationship to antioxidant activity and to iron ion-reducing ability. Biochemical Pharmacology 42, 16731681.CrossRefGoogle ScholarPubMed
Leist, M, Raab, B, Maurer, S, Rösick, U & Brigelius-Flohé, R (1996) Conventional cell culture media do not adequately supply cells with antioxidants and thus facilitate peroxide-induced genotoxicity. Free Radicals in Biology and Medicine 21, 297306.CrossRefGoogle Scholar
Manna, C, Della Regione, F, Cucciolla, V, Borriello, A, D'Àngelo, S, Galletti, P & Zappia, V (1999) Biological effects of hydroxytyrosol, a polyphenol from olive oil endowed with antioxidant activity. In Advances in Nutrition and Cancer 2, pp. 115130 [Zappia, V, editor]. New York, NY: Plenum Publishers.CrossRefGoogle Scholar
Manna, C, Galleti, P, Cucciolla, V, Moltedo, O, Leone, A & Zappia, V (1997) The protective effect of the olive oil polyphenol (3,4-Dihydroxyphenyl)-ethanol counteracts reactive oxygen metabolite-induced cytotoxicity in Caco-2 cells. Journal of Nutrition 127, 286292.Google Scholar
Manna, C, Galletti, P, Maisto, G, Cucciolla, V, D'Angelo, S & Zappia, V (2000) Transport mechanism and metabolism of olive oil hydroxytyrosol in Caco-2 cells. FEBS Letters 470, 341344.CrossRefGoogle ScholarPubMed
Masella, R, Cantafora, A, Modesti, D, Cardilli, A, Gennaro, L, Bocca, A & Coni, E (1999) Antioxidant activity of 3,4-DHPEA-EA and protocateuuic acid, a comparative assessment with other olive oil biophenols. Redox Report 4, 113121.CrossRefGoogle ScholarPubMed
Mataix, J, Quiles, JL, Huertas, JR, Battino, M & Mañas, M (1998) Tissue specific interactions of exercise, dietary fatty acids, and vitamin E in lipid peroxidation. Free Radicals in Biology and Medicine 24, 511521.CrossRefGoogle ScholarPubMed
Mattson, FH & Grundy, SM (1985) Comparison of dietary saturated, monounsaturated, and polyunsaturated fatty acids on plasma lipids and lipoproteins in man. Journal of Lipid Research 26, 194202.CrossRefGoogle ScholarPubMed
Middleton, E & Kandaswami, C (1992) Effects of flavonoids on immune and inflammatory cell functions. Biochemical Pharmacology 43, 11671179.CrossRefGoogle ScholarPubMed
Montedoro, G, Servili, M, Baldioli, M & Miniati, E (1992) Simple and hydrolyzable phenolic compounds in virgin olive oil. 1. Their extraction, separation and quantitative and semiquantitative evaluation by HPLC. Journal of Agricultural and Food Chemistry 40, 15711576.CrossRefGoogle Scholar
Newmark, HL (1987) Plant phenolics as inhibitors of mutational and precarcinogenic events. Canadian Journal of Physiology and Pharmacology 65, 461466.CrossRefGoogle ScholarPubMed
Owen, RW, Giacosa, A, Hull, WE, Haubner, R, Spiegelhalder, B & Bartsch, H (2000) The antioxidant/anticancer potential of phenolic compounds isolated from olive oil. European Journal of Cancer 36, 12351247.CrossRefGoogle ScholarPubMed
Petroni, A, Blasevich, M, Papini, N, Salami, M, Sala, A & Galli, C (1997) Inhibition of leukocyte leukotriene B4 production by an olive oil-derived phenol identified by mass spectrometry. Thrombosis Research 87, 315322.CrossRefGoogle ScholarPubMed
Quiles, JL, Huertas, JR, Mañas, M, Battino, M & Mataix, J (1999 a) Physical exercise affects the lipid profile of mitochondrial membranes in rats fed with virgin olive oil or sunflower oil. British Journal of Nutrition 81, 2124.CrossRefGoogle ScholarPubMed
Quiles, JL, Ramírez-Tortosa, MC, Ibáñez, S, González, JA, Duthie, GG, Huertas, JR & Mataix, J (1999 b) Vitamin E supplementation increases the stability and the in vivo antioxidant capacity of refined olive oil. Free Radical Research 31, S129S135.CrossRefGoogle ScholarPubMed
Ramírez-Tortosa, MC, Urbano, G, López-Jurado, M, Nestares, T, Gonzalez, MC, Mir, A, Ros, E, Mataix, J & Gil, A (1999) Extra-Virgin more than Refined Olive Oil Increases the Resistance of LDL to Oxidation in Free-Living Men with Peripheral Vascular Disease. Journal of Nutrition 129, 21772183.CrossRefGoogle ScholarPubMed
Sies, H (1993) Strategies of antioxidant defense. European Journal of Biochemistry 215, 213219.CrossRefGoogle ScholarPubMed
Stavric, B (1994) Role of chemopreventers in human diet. Clinical Biochemistry 27, 319332.CrossRefGoogle ScholarPubMed
Visioli, F, Bellomo, G & Galli, C (1998 a) Free radical-scavenging properties of olive oil polyphenols. Biochemical Biophysical Research Communications 247, 6064.CrossRefGoogle ScholarPubMed
Visioli, F, Bellosta, S & Galli, C (1998 b) Oleuropein, the bitter principle of olives, enhances nitric oxide production by mouse macrophages. Life Science 62, 541546.CrossRefGoogle ScholarPubMed
Visioli, F, Caruso, D, Galli, C, Viappiani, S, Galli, G & Sala, A (2000 a) Olive oils rich in natural catecholic phenols decrease isoprostane excretion in humans. Biochemical and Biophysical Research Communications 278, 797799.CrossRefGoogle Scholar
Visioli, F & Galli, C (1998) The effect of minor constituents of olive oil on cardiovascular disease, new findings. Nutrition Reviews 56, 142147.CrossRefGoogle ScholarPubMed
Visioli, F, Galli, C, Bornet, M, Mattei, A, Patelli, R, Galli, G & Caruso, D (2000 b) Olive oil phenolics are dose-dependently absorbed in humans. FEBS Letters 468, 159160.CrossRefGoogle ScholarPubMed
Willett, WC (1997) Specific fatty acids and the risk of breast and prostate cancer, dietary intake. American Journal of Clinical Investigation 66, 1557S1576S.Google ScholarPubMed