The phenolic compounds of olive oil: Structure, biological activity and beneficial effects on human health

Nutrition Research Reviews

Volumn 18, Issue 1, 2005, Pages 98-112

  Tripoli, Elisa ^a   Giammanco, Marco ^a   Tabacchi, Garden ^a   Di Majo, Danila ^a   Giammanco, Santo ^a   La Guardia, Maurizio ^a  

^a UNIVERSITY OF PALERMO   (Italy)

Author keywords

Antioxidants; Cardiovascular diseases; Oleuropein; Olive oil; Phenolic compounds

Indexed keywords

1 ACETOXYPINORESINOL; 1 HYDROXYPINORESINOL; 10 HYDROXYLIGSTROSIDE; 10 HYDROXYOLEUROPEIN; ACTEOSIDE; ALPHA TOCOPHEROL; ANDROSTENEDIONE; ANTHOCYANIN; ANTIOXIDANT; ASCORBIC ACID; BETA CAROTENE; CAFFEIC ACID; CAROTENE; COPPER; DELPHINIDIN; DEMETHYLOLEUROPEIN; ELENOLIC ACID; ENDOTOXIN; ENTEROTOXIN; ESTRADIOL; ESTRONE; FLAVONOL; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE; HYDROXYTYROSOL; IRON; LEUKOTRIENE B4; LIGNAN; LIGSTROSIDE; LIPOXYGENASE; LUTEOLIN 7 GLUCOSIDE; LYCOPENE; NITRIC OXIDE; NUZHENIDE; OLEUROPEIN; OLIVE OIL; PEROXYNITRITE; PHENOL DERIVATIVE; PINORESINOL; POLYPHENOL; REACTIVE OXYGEN METABOLITE; RUTOSIDE; SATURATED FATTY ACID; SECOIRIDOID; STEROID HORMONE; TESTOSTERONE; THROMBOXANE B2; TRANSITION ELEMENT; TYROSOL; UNCLASSIFIED DRUG; UNSATURATED FATTY ACID; XANTHINE OXIDASE;

ANTIINFLAMMATORY ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ANTIVIRAL ACTIVITY; ATHEROSCLEROSIS; BACILLUS CEREUS; CARDIOVASCULAR DISEASE; CELL STRAIN CACO 2; CHEMICAL STRUCTURE; CONTROLLED STUDY; CORYNEBACTERIUM; DEGENERATIVE DISEASE; DIABETES MELLITUS; ENZYME ACTIVITY; ESCHERICHIA COLI; FORSYTHIA; HAEMOPHILUS INFLUENZAE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; INFLAMMATORY DISEASE; KLEBSIELLA PNEUMONIAE; LIPID PEROXIDATION; LIVER MICROSOME; MASS SPECTROMETRY; MEDITERRANEAN DIET; MORAXELLA CATARRHALIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLIVE TREE; OXIDATIVE STRESS; PSEUDOMONAS SYRINGAE; REVIEW; RHEUMATOID ARTHRITIS; SALMONELLA ENTERITIDIS; SESAME; STAPHYLOCOCCUS AUREUS; THROMBOCYTE AGGREGATION INHIBITION;

EID: 20444476857     PISSN: 09544224     EISSN: None     Source Type: Journal    
DOI: 10.1079/NRR200495     Document Type: Review

References (166)

1. Abbey M, Nestel PJ & Baghurst PA (1993) Antioxidant vitamins and low density lipoprotein oxidation. American Journal of Clinical Nutrition 58, 52.
2. Adlercreutz H, Bannwart C, Wähälä K, Makela T, Brunow G, Hase T, Arosemena PJ, Kellis JT Jr & Vickery LE (1993) Inhibition of human aromatase by mammalian lignans and isoflavoid phytooestrogens. Journal of Steroid Biochemistry and Molecular Biology 44, 147-153.
3. Adlercreutz H, Mousavi Y, Clark J, Hockerstedt K, Hamalainen E, Wähälä K, Makela T & Hase T (1992) Dietary phytoestrogens and cancer: in vitro and in vivo studies. Journal of Steroid Biochemistry and Molecular Biology 41, 331-337.
4. Aeschbach R, Loliger J, Scott BC, Murcia A, Butler J, Halliwell B & Aurome OI (1994) Antioxidant actions of tymol, carvacrol, 6-gingerolo, zingerone and hydroxytyrosol. Food and Chemical Toxicology 32, 31-36.
5. Alarcon de la Lastra C, Barranco MD, Motilova V & Herrerias JM (2001) Mediterranean diet and health: biological importance of olive oil. Current Pharmaceutical Design 7, 933-950.
6. Alloggio V & Caponio F (1997) The influence of olive paste preparation techniques on the quality of olive oil. II. Evolution of phenolic substances and of some quality parameters referred to the ripening of drupes in virgin olive oil from the Coratina cv. Rivista Italiana Sostanze Grasse 74, 443-447.
7. Amiot MJ, Fleuriet A & Macheix JJ (1986) Importance and evolution of phenolic compounds in olive during growth and maturation. Journal of Agricultural and Food Chemistry 34, 823-826.
8. Amiot MJ, Fleuriet A & Macheix JJ (1989) Accumulation of oleuropein derivatives during olive maturation. Photochemistry 28, 67-69.
9. Angerosa F, D'Alessandro N, Konstantinou P & Di Giacinto L (1995) GC-MS evaluation of phenolic compounds in virgin olive oil. Journal of Agricultural and Food Chemistry 43, 1802-1807.
10. Aruoma OI (1994) Nutrition and health aspects of free radicals and antioxidants. Food and Chemical Toxicology 32, 671-683.
11. Aruoma OI, Deiana M, Jenner A, Halliwell B, Harparkash K, Banni S, Corongiu FF, Dessi MA & Aeschbach R (1998) Effect of hydroxytyrosol found in extra virgin olive oil on DNA damage and on low-density lipoprotein oxidation. Journal of Agricultural and Food Chemistry 46, 5181-5187.
12. Aziz NH, Farag SE, Mousa LAA & Abo Zaid MA (1998) Comparative antibacterial and antifungal effects of some phenolic compounds. Microbios 93, 43-54.
13. Bai C, Yan X, Takenake M, Sekiya K & Nagata T (1998) Determination of synthetic hydroxytyrosol in rat plasma by GC-MS. Journal of Agricultural and Food Chemistry 46, 3998-4001.
14. Benkhalti F, Prost J, Paz E, Perez-Jimenez F, El Modafar C & El Boustani E (2002) Effects of feeding virgin olive oil or their polyphenols on lipid of rat liver. Nutrition Research 22, 1067-1075.
15. Berra B, Caruso D, Cortesi N, Fedeli E, Rasetti MF & Galli G (1995) Antioxidant properties of minor polar components of olive oil on the oxidative processes of cholesterol in human LDL. La Rivista Italiana delle Sostanze Grasse 72, 285-288.
16. Beuchat LR & Golden DA (1989) Antimicrobials occurring naturally in foods. Food Technology 43, 134-142.
17. Bianco A, Lo Scalzo R & Scarpati ML (1993) Isolation of cornoside from Olea europaea and its transformation into halleridone. Phytochemistry 32, 455-457.
18. Bianco A & Uccella N (2000) Biophenolic components of olives. Food Research International 33, 475-485.
19. Bianco AD, Mazzei RA, Melchioni C, Romeo G, Scarpati ML & Uccella N (1998a) Microcomponents of olive oil. Part II: digalactosyldiacylglycerols from Olea europaea. Food Chemistry 62, 343-346.
20. Bianco AD, Mazzei RA, Melchioni C, Romeo G, Scarpati ML & Uccella N (1998b) Microcomponents of olive oil-III. Glucosides of 2 (3, 4-dihydroxy-phenyl)ethanol. Food Chemistry 63, 461-464.
21. Bisignano G, Tomaino A, Lo Cascio R, Crisafi G, Uccella N & Saija A (1999) On the in-vitro antimicrobial activity of oleuropein and hydroxytyrosol. Journal of Pharmacy and Pharmacology 51, 971-974.
22. Bonanome A, Pagnan A, Biffanti S, Opportuno A, Sorgato F, Dorella M, Maiorino M & Ursini F (1992) Effect of dietary monounsaturated and polyunsaturated fatty acids on the susceptibility of plasma low density lipoproteins to oxidative modification. Arteriosclerosis and Thrombosis 12, 529-533.
23. Bourne LC & Rice-Evans CA (1998) Urinary detection of hydroxycinnamates and flavonoids in humans after high dietary intake of fruit. Free Radical Research 28, 429-438.
24. Brenes M, Garcia A, Garcia P, Rios JJ & Garrido A (1999) Phenolic compounds in Spanish olive oils. Journal of Agricultural and Food Chemistry 47, 3535-3540.
25. Brown MS & Goldstein JL (1983) Lipoprotein metabolism in the macrophage: implications for cholesterol deposition in atherosclerosis. Annual Review of Biochemistry 52, 223.
26. Burant C, Takeda J, Brot-Laroche E, Bell G & Davidson N (1992) Fructose transporter in human spermatozoa and small intestine is Glut5. Journal of Biological Chemistry 267, 14523-14526.
27. Calis I, Saracoglu I, Zor M & Alacam R (1988) Antimicrobial activities of some phenylpropanoid glycosides isolated from Scrophularia scopoli. Turk Tip Eczacilik Dergisi 12, 230-233.
28. Cao G, Sofic E & Prior RL (1997) Antioxidant and prooxidant behavior of flavonoids: structure-activity relationships. Free Radical Biology and Medicine 22, 749-760.
29. Capasso R, Cristinzio G, Evidente A & Scognamiglio F (1992) Isolation, spectroscopy and selective phytotoxic effects of polyphenols from vegetable waste waters. Phytochemistry 31, 4125-4128.
30. Capasso R, Evidente A, Avolio S & Solla F (1999) A highly convenient synthesis of hydroxytyrosol and its recovery from agricultural waste waters. Journal of Agricultural and Food Chemistry 47, 1745-1748.
31. Capasso R, Evidente A, Schivo L, Orru G, Marcialis MA & Cristinzio G (1995) Antibacterial polyphenols from olive oil mill waste waters. Journal of Applied Bacteriology 79, 393-398.
32. Caruso D, Colombo R, Patelli R, Giavarini F & Galli G (2000) Rapid evaluation of phenolic component profile and analysis of oleuropein aglycon in olive oil by atmospheric pressure chemical ionization-mass spectrometry (APCI-MS). Journal of Agricultural and Food Chemistry 48, 1182-1185.
33. Caruso D, Visioli F, Patelli R, Galli C & Galli G (2001) Urinary excretion of olive oil phenols and their metabolites in humans. Metabolism Clinical and Experimental 50, 1426-1428.
34. Chen J, Blanc P, Stoddart CA, Bogan M, Rozhon EJ, Parkinson N, Ye Z, Cooper R, Balick M, Nanakorn W, Kernan MR, Chen JL & Ye ZJ (1998) New iridoids from the medicinal plant Barleria prionitis with potent activity against respiratory syncytial virus. Journal of Natural Products 61, 1295-1297.
35. 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, 1259-1264.
36. Climato A, Mattel A & Osti M (1990) Variation of poly phenol composition with harvesting period. Acta Horticulturae 286, 453-456.
37. Colditz GA (1993) Epidemiology of breast cancer. Findings from the Nurses' Health Study. Cancer 71, 1480-1489.
38. Cominacini L, Garbin U, Cenci B & Davoli A (1991) Predisposition to LDL oxidation during copper-catalyzed oxidative modification and its relation to α-tocopherol content in humans. Clinica Chimica Acta 204, 57-68.
39. D'Angelo S, Manna C, Migliardi V, Mazzoni O, Monica P, Capasso G, Pontoni G, Galletti P & Zappia V (2001) Pharmacokinetics and metabolism of hydroxytyrosol, a natural antioxidant from olive oil. Drug Metabolism and Disposition 29, 1492-1498.
40. Davin BD, Bedgar DL, Katayama T & Lewis NG (1992) On the stereoselective synthesis of (+)-pinoresinol in Forsythia suspensa from its achiral precursor, coniferyl alcohol. Phytochemistry 31, 3869-3874.
41. Deiana M, Aruoma OI, Bianchi MDLP, Spencer JPE, 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 Radical Biology and Medicine 26, 762-769.
42. De la Puerta R, Martínez-Domínguez E & Ruíz-Gutiérrez V (2000) Effect of minor components of virgin olive oil on topical antunflammatory assays. Zeitschrift für Naturforschung 55C, 814-819.
43. De la Puerta R, Ruiz Gutierrez V, Robin J & Hoult S (1999) Inhibition of leukocyte 5-lipoxygenase by phenolics from virgin olive oil. Biochemical Pharmacology 57, 445-449.
44. De Pergola G, Giorgino F, Garruti G, Cignarelli M & Giorgino R (1996) Rapporto tra variabili antropometriche, ormoni sessuali e complicanze dell'obesità (Relationship between anthropometric variables, sex hormones and complications in obesity). Metabolismo Oggi 13, 138-145.
45. de Rojas-Walker T, Tamir S, Ji H, Wishnock J & Tennanbaum SR (1995) Nitric oxide induces oxidative damage in addition to deamination in macrophages DNA. Chemical Research in Toxicology 8, 473-477.
46. Edgecombe SC, Stretch GL & Hayball PJ (2000) Oleuropein, an antioxidant polyphenol from olive oil, is poorly absorbed from isolated perfused rat intestine. Journal of Nutrition 130, 2996-3002.
47. Eling TE, Curtis JF, Harman LS & Mason RP (1986) Oxidation of glutathione to its thiyl free radical metabolite by prostaglandin H synthase. Journal of Biological Chemistry 261, 5023-5028.
48. Esterbauer H, Gebicki J, Puhl H & Jurgens G (1992) The role of lipid peroxidation and antioxidants in oxidative modification of LDL. Free Radical Biology and Medicine 13, 341.
49. Esti M, Cinquanta L, Notte EI & La Notte E (1998) Phenolic compounds in different olive varieties. Journal of Agricultural and Food Chemistry 46, 32-35.
50. Federici F & Bongi G (1983) Improved method for isolation of bacterial inhibitors from oleuropein hydrolysis. Applied and Environmental Microbiology 46, 509-510.
51. Finotti E & Di Majo D (2003) Influence of solvents on the antioxidant property of flavonoids. Nahrung/Food 47, 186-187.
52. Garrido Fernández A, Fernández Diez MJ & Adams MR (1997) Table Olives: Production and Processing, pp. 67-109. London: Chapman & Hall.
53. Gourama H & Bullerman LB (1987) Effects of oleuropein on growth and aflatoxin production by Aspergillus parasiticus. Lebensmittel Wissenschaft Technologie 20, 226-228.
54. Gutierrez F, Jimenez B, Ruiz A & Albi MA (1999) Effect of olive ripeness on the oxidative stability of virgin olive oil extracted from the varieties picual and hojiblanca and on the different components involved. Journal of Agricultural and Food Chemistry 47, 121-127.
55. Halliwell B (1997) Antioxidants and human disease: a general introduction. Nutrition Reviews 55, 44-52.
56. Halliwell B, Aeschbach R, Loliger J & Aruoma OI (1995) The characterization of antioxidants. Food and Chemical Toxicology 33, 601-617.
57. Halliwell B & Gutterige MC (1990) Role of free radicals and catalytic metal ions in human disease: an overview. Methods in Enzymology 186, 1-85.
58. Hankinson SE, Willett WC, Manson JE, Hunter DJ, Colditz GA, Stampfer MJ, Longcope C & Speizer FE (1995) Alcohol, height, and adiposity in relation to estrogen and prolactin levels in postmenopausal women. Journal of the National Cancer Institute 87, 1297-1302.
59. Hertog MLG, Feskens EJM, Katan MB & Kromhout D (1993) Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen Elderly Study. Lancet 342, 1007.
60. Hirano T, Fukuoka F, Oka K, Naito T, Hosaka K, Mitsuhashi H & Matsumoto Y (1990) Antiproliferative activity of mammalian lignan derivatives against the human breast carcinoma cell line, ZR-75-1. Cancer Investigation 8, 592-602.
61. Hirschman SZ (1972) Inactivation of DNA polymerases of murine leukaemia viruses by calcium elenolate. Nature: New Biology 238, 277-279.
62. Huang MT, Osawa T, Ho CT & Rosen RT (1994) Food phytochemicals for cancer prevention. In Fruits and Vegetables. ACS Symposium Series no. 46. Washington, DC: American Chemical Society.
63. Jialal I, Fuller CJ & Huet BA (1995) The effect of α-tocopherol supplementation on LDL oxidation. A dose-response study. Arteriosclerosis, Thrombosis, and Vascular Biology 15, 190-198.
64. Johnson IT, Williamson G & Musk SRR (1994) Anticarcinogenic factors in plant foods. A new class of nutrients. Nutrition Research Reviews 7, 1-30.
65. Juven B, Henis Y & Jacoby B (1972) Studies on the mechanism of the antimicrobial action of oleuropein. Journal of Applied Bacteriology 35, 559-567.
66. Kane S, Seatter M & Gould G (1997) Functional studies of human Glut5: effect of pH on substrate selection and an analysis of substrate interactions. Biochemical and Biophysical Research Communications 238, 503-505.
67. Kardono LB, Tsauri S, Pezzuto JM & Kinghorn AD (1990) Cytotoxic constituents of the bark of Plumeria rubra collected in Indonesia. Journal of Natural Products 53, 1447-1455.
68. Kato MJ, Chu A, Davin LB & Lewis NG (1998) Biosynthesis of antioxidant lignans in Sesamum indicum seeds. Phytochemistry 47, 583-591.
69. Kayano T, Burant C, Fukumoto H, Gould G, Fan Y, Eddy R, Byers M, Shows T, Seino S & Bell G (1990) Human facilitative glucose transporters. Journal of Biological Chemistry 265, 13276-13282.
70. Keceli T & Gordon MH (2001) The antioxidant activity and stability of the phenolic fraction of green olives and extra virgin olive oil. Journal of the Science of Food and Agriculture 81, 1391-1396.
71. Kernan MR, Amarquaye A, Chen J, Chan J, Sesin DF, Parkinson N, Ye Z, Barren M, Bales C, Stoddart CA, Sloan B, Blanc P, Limbach C, Mrisho S, Rozhon EJ, Chen JL & Ye ZJ (1998) Antiviral phenylpropanoid glycosides from the medicinal plant Markhamia lutea. Journal of Natural Products 61, 564-570.
72. Keys A (1995) Mediterranean diet and public health: personal reflections. American Journal of Clinical Nutrition 61, 1321-1323.
73. Kissebah AH & Krakower GR (1994) Regional adiposity and morbidity. Physiological Reviews 74, 761-811.
74. Kohyama N, Nagata T, Fujimoto S & Sekiya K (1997) Inhibition of arachidonate lipoxygenase activities by 2-(3, 4-dihydroxyphenyl)ethanol, a phenolic compound from olives. Bioscience, Biotechnology, and Biochemistry 61, 347-350.
75. Laranjinha JA, Almeida LM & Madeira VM (1994) Reactivity of dietary phenolic acids with peroxyl radicals: antioxidant activity upon low density lipoprotein peroxidation. Biochemical Pharmacology 48, 487-494.
76. Leenen R, Roodenburg AJ, Vissers MN, Schuurbiers JA, van Putte KP, Wiseman SA & van de Put FH (2002) Supplementation of plasma with olive oil phenols and extracts: influence on LDL oxidation. Journal of Agricultural and Food Chemistry 50, 1290-1297.
77. 13C NMR characterization of oleuropein aglycones. Journal of the Chemical Society, Perkin Transactions 15, 1519-1523.
78. 1H NMR study of phenolics in the vegetation water of three cultivars of Olea europaea: similarities and differences. Journal of Agricultural and Food Chemistry 44, 2040-2048.
79. Lipworth L, Martinez ME, Angell J, Hsien CC & Trichopoulos D (1997) Olive oil and human cancer an assessment of evidence. Preventive Medicine 26, 181-190.
80. Lo Scalzo R, Scarpati ML & Scalzo RI (1993) A new secoiridoid from olive wastewaters. Journal of Natural Products 56, 621-623.
81. Maggino T, Pirrone F, Velluti F & Bucciante G (1993) The role of the endocrine factors and obesity in hormone-dependent gynecological neoplasias. European Journal of Gynaecological Oncology 14, 119-126.
82. Manna C, Galletti 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, 286-292.
83. Manna C, Galletti P, Cucciolla V, Montedoro GF & Zappia V (1999) Olive oil hydroxytirosol protects human erythrocytes against oxidative damages. Journal of Nutritional Biochemistry 10, 159-165.
84. Manna C, Galletti P, Misto G, Cucciolla V, D'Angelo S & Zappia V (2000) Transport mechanism and metabolism of olive oil hydroxytyrosol in Caco-2 cells. FEBS Letters 470, 341-344.
85. Mannino S, Cosio MS & Bertuccioli M (1993) High performance liquid chromatography of phenolic compounds in virgin olive oil using amperometric detector. Italian Journal of Food Science 4, 363-370.
86. Martinez-Dominguez E, de la Puerta R & Ruiz-Gutierrez V (2001) Protective effects upon experimental inflammation models of a polyphenol-supplemented virgin olive oil diet. Inflammation Research 50, 102-106.
87. Masella R, Cantafora A, Modesti D, Cardilli A, Gennnaro L, Bocca A & Coni E (1999) Antioxidant activity of 3, 4-DHPEA-EA and protocatechuic acid: a comparative assessment with other olive oil biophenols. Redox Report 4, 113-121.
88. Miró Casas E, Albadalejo MF, Covas Planells MI, Colomer MF, Lamuela Raventós RM & de la Torre Fornell R (2001) Tyrosol bioavailability in humans after ingestion of virgin olive oil. Clinical Chemistry 47, 341-343.
89. Miró Casas E, Covas MI, Farre M, Fito M, Ortuno J, Weinbrenner T, Roset P & de la Torre R (2003) Hydroxytyrosol disposition in humans. Clinical Chemistry 49, 945-952.
90. Mirochnitchenko O, Prokopenko O, Palnitkar U, Kister I, Powell WS & Inouye M (2000) Endotoxemia in transgenic mice overexpressing human glutathione peroxidases. Circulation Research 87, 289-295.
91. Montedoro GF (1972) I costituenti fenolici presenti negli oli vergini di oliva. Nota 1: identificazione di alcuni acidi fenolici e loro potere antiossidante (Phenolic constituents present in virgin olive oils. Part 1: identification of some phenolic acids and their antioxidant ability). STA 3, 177-186.
92. 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, 1571-1576.
93. Monteleone E, Caporale G, Carlucci A & Pagliarini E (1998) Optimisation of extra virgin olive oil quality. Journal of the Science of Food and Agriculture 77, 31-37.
94. Moreno JJ & Mitjavilab MT (2003) The degree of unsaturation of dietary fatty acids and the development of atherosclerosis (Review). Journal of Nutritional Biochemistry 14, 182-195.
95. Mosca L, De Marco C, Visioli F & Cannella C (2000) Enzymatic assay for the determination of olive oil polyphenol content: assay conditions and validation of the method. Journal of Agricultural and Food Chemistry 48, 297-301.
96. Mousavi Y & Adlercreutz H (1992) Enterolactone and estradiol inhibit each others proliferative effect on MCF-7 breast cancer cells in culture. Journal of Steroid Biochemistry and Molecular Biology 41, 615-619.
97. Mulinacci N, Romani A, Galardi C, Pinelli P, Giaccherini C & Vincieri FF (2001) Polyphenolic content in olive oil waste waters and related olive samples. Journal of Agricultural and Food Chemistry 49, 3509-3514.
98. Nardini M, D'aquino M, Tomassi G, Gentili V, Di Felice M & Scaccini C (1995) Inhibition of human low-density lipoprotein oxidation by caffeic acid and other idroxycinnamic acid derivatives. Free Radical Biology and Medicine 19, 541-552.
99. Newcomb TG & Loeb LA (1998) Mechanism of mutagenicity of oxidatively-modified bases. In Molecular Biology of Free Radicals in Human Diseases, pp. 137-166 [OI Aruoma and B Halliwell, editors]. Saint Lucia: OICA International.
100. Nomoto M, Yamada K, Haga M & Hayashi M (1998) Improvement of intestinal absorption of peptide drugs by glycosylation: transport of tetrapeptide by the sodium ion-dependent D-glucose transporter. Journal of Pharmaceutical Sciences 87, 326-332.
101. Owen RW, Giacosa A, Hull WE, Haubner R, Spiegelhalder B & Bartsch H (2000a) The antioxidant/anticancer potential of phenolic compounds isolated from olive oil. European Journal of Cancer 36, 1235-1247.
102. Owen RW, Giacosa A, Hull WE, Haubner R, Wurtele G, Spiegelhalder B & Bartsch H (2000b) Olive-oil consumption and health: the possible role of antioxidants. Lancet Oncology 1, 107-112.
103. Owen RW, Mier W, Giacosa A, Hull WE, Spiegelhalder B & Bartsch H (2000c) Identification of lignans as major components in the phenolic fraction. Clinical Chemistry 46, 976-988.
104. Papadopoulos G & Boskou D (1991) Antioxidant effect of natural phenols on olive oil. Journal of the American Oil Chemists Society 68, 669-671.
105. Pardo F, Perich F, Villarroel L & Torres R (1993) Isolation of verbascoside, an antimicrobial constituent of Buddleja globosa leaves. Journal of Ethnopharmacology 39, 221-222.
106. Parthasarathy S (1991) Novel atherogenic oxidative modification of low density lipoprotein. Diabetes/Metabolism Reviews 7, 163.
107. Petroni A, Blasevich M, Salami M, Papini N, Montedoro GF & Galli C (1995) Inhibition of platelet aggregation and eicosanoid production by phenolic components of olive oil. Thrombosis Research 78, 151-160.
108. Pezzuto JM (1997) Plant-derived anticancer agents. Biochemical Pharmacology 53, 121-133.
109. Prasad K (1997) Hydroxyl radical-scavenging property of secoisolar-iciresinol diglucoside (SDG) isolated from flaxseed. Molecular and Cellular Biochemistry 168, 117-123.
110. Princen HMG, van Poppel G, Vogelazang C, Buytenhek R & Kok FJ (1992) Supplementation with vitamin E but not β-carotene in vivo protects low density lipoprotein from lipid peroxidation in vitro. Arteriosclerosis and Thrombosis 12, 554.
111. Ranalli A, De Mattia G & Ferrante ML (1997) Comparative evaluation of the olive oil given by a new processing system. International Journal of Food Science and Technology 32, 289-297.
112. Ranalli A, De Mattia G & Ferrante ML (1998) The characteristics of percolation olive oils produced with a new processing enzyme aid. International Journal of Food Science and Technology 33, 247-258.
113. Ranalli A, Ferrante ML, De Mattia G & Costantini N (1999) Analytical evaluation of virgin olive oil of first and second extraction. Journal of Agricultural and Food Chemistry 47, 417-424.
114. Reaven PD, Khouw A, Beltz WF, Parthasarathy S & Witztum J (1993) Effect of dietary antioxidant combinations in humans. Protection of LDL by vitamin E but not by β-carotene. Arteriosclerosis and Thrombosis 13, 590.
115. Reaven PD, Parthasarathy S, Grasse BJ, Miller E, Almazan F, Mattson FH, Khoo JC, Steinberg D & Witztum JL (1991) Feasibility of using an oleate-rich diet to reduce the susceptibility of low-density lipoprotein to oxidative modification in humans. American Journal of Clinical Nutrition 54, 701-706.
116. Rice-Evans CA, Miller NJ & Paganga G (1996) Structure-antioxidant activity relationship of flavonoids and phenolic acids. Free Radical Biology and Medicine 20, 933-956.
117. Rohn TT, Hinds TR & Vincenzi FF (1993) Ion transport ATPases as targets for free radical damage. Protection by an aminosteroid of the Ca21 pump ATPase and Na1/K1 pump ATPase of human red blood cell membranes. Biochemical Pharmacology 46, 525-534.
118. Ryan D, Lawrence H, Prenzler PD & Antolovic M (2001) Recovery of phenolic compounds from Olea europeae. Analytica Chimica Acta 445, 67-77.
119. Sadrzadeh SMH, Graf E, Panter SS, Hallaway PE & Eaton JW (1984) Hemoglobin. A biologic Fenton reagent. Journal of Biological Chemistry 259, 14354-14356.
120. Salami M, Galli C, De Angelis L & Visioli F (1995) Formation of F2-isoprostanes in oxidized low density lipoprotein. Inhibitory effects of hydroxytyrosol. Pharmacological Research 31, 275-279.
121. Scaccini C, Nardini M, D'Acquino M, Gentili V, Di Felice M & Tomassi G (1992) Effect of dietary oils on lipid peroxidation and on antioxidant parameters of rat plasma and lipoprotein fractions. Journal of Lipid Research 33, 627-633.
122. Schapira DV, Kumar NB & Lyman GH (1991) Obesity, body fat distribution, and sex hormones in breast cancer patients. Cancer 67, 2215-2218.
123. Schroder HC, Merz H, Steffen R, Muller WE, Sarin PS, Trumm S, Schulz J & Eich E (1990) Differential in vitro antiHIV activity of natural lignans. Zeitschrift Naturforschung 45, 1215-1221.
124. Serraino M & Thompson LU (1991) The effect of flaxseed supplementation on early risk markers for mammary carcinogenesis. Cancer Letters 60, 135-142.
125. Serraino M & Thompson LU (1992) The effect of flaxseed consumption on the initiation and promotional stages of mammary carcinogenesis. Nutrition and Cancer 17, 153-159.
126. Servili M, Baldioli M, Selvaggini R, Macchioni A & Montedoro GF (1999a) Phenolic compounds of olive fruit: one- and two-dimensional nuclear magnetic resonance characterization of nüzhenide and its distribution in the constitutive parts of fruit. Journal of Agricultural and Food Chemistry 47, 12-18.
127. Servili M, Baldioli M, Selvaggini R, Miniati E, Macchioni A & Montedoro GF (1999b) HPLC evaluation of phenols in olive fruit, virgin olive oil, vegetation waters and pomace and ID and 2D-NMR characterization. Journal of the American Oil Chemists Society 76, 873-882.
128. Soler-Rivas C, Espin JC & Wichers HJ (2000) Oleuropein and related compounds. Journal of the Science of Food and Agriculture 80, 1013-1023.
129. Solinas M & Cichelli A (1981) Sulla determinazione delle sostanze fenoliche dell'olio di oliva (On the determination of phenolic substances of olive oil). Rivista Italiana Sostanze Grasse 58, 159-164.
130. Speroni E, Guerra MC, Minghetti A, Crespi-Perellino N, Pasini P, Piazza F & Roda A (1998) Oleuropein evaluated in vitro and in vivo as an antioxidant. Phytotherapy Research 12, 98-100.
131. Stretch G, Nation R, Evans A & Milne R (1999) Organ perfusion techniques in drug development. Drug Development Research 46, 292-301.
132. Takata K (1995) Glucose transporters in the transepithelial transport of glucose. Journal of Electron Microscopy 45, 275-284.
133. Tanaka T, Makita H, Kawamori T, Kawabata K, Mon H, Murakami A, Satoh K, Kara A, Ohigashi H & Koshimizu K (1997) A xanthine oxidase inhibitor 10 acetoxychavicol acetate inhibits azoxymethane-induced colonic aberrant crypt foci in rats. Carcinogenesis 18, 1113-1118.
134. Tassou CC & Nychas GJE (1994) Inhibition of Staphylococcus aureus by olive phenolics in broth and in a model food system. Journal of Food Protection 57, 120-124.
135. Tassou CC & Nychas GJE (1995) Inhibition of Salmonella enteritidis by oleuropein in broth and in a model food system. Letters in Applied Microbiology 20, 120-124.
136. Tassou CC, Nychas GJE & Board RG (1991) Effect of phenolic compounds and oleuropein on the germination of Bacillus cereus T spores. Biotechnology and Applied Biochemistry 13, 231-237.
137. Thompson LU, Seidl MM, Rickard SE, Orcheson LJ & Fong HH (1996) Antitumorigenic effect of a mammalian lignan precursor from flaxseed. Nutrition and Cancer 26, 159-165.
138. Tranter HS, Tassou SC & Nychas GJ (1993) The effect of the olive phenolic compound, oleuropein, on growth and enterotoxin B production by Staphylococcus aureus. Journal of Applied Bacteriology 74, 253-259.
139. Trichopoulou A (1995) Olive oil and breast cancer. Cancer Causes Control 6, 475-476.
140. Trichopoulou A, Vasilopoulou E & Lagiou A (1999) Mediterranean diet and coronary heart disease: are antioxidants critical? Nutrition Reviews 57, 253-255.
141. Tsimidou M, Lytridou M, Boskou D, Paooa-Lousi A, Kotsifaki F & Petrakis C (1996) On the determination of minor phenolic acids of virgin olive oil by RP-HPLC. Grasas y Aceites en la Nutrición Humana 47, 151-157.
142. Tsukamoto H, Hisada S & Nishibe S (1984) Lignans from bark of the Olea plants, 1. Chemical and Pharmaceutical Bulletin 32, 2730-2735.
143. Tsukamoto H, Hisada S & Nishibe S (1985) Lignans from bark of the Olea plants, 2. Chemical and Pharmaceutical Bulletin 33, 1232-1241.
144. Tuck KL, Freeman MP, Hayball PJ, Stretch GL & Stupans I (2001) The in vivo fate of hydroxytyrosol and tyrosol, antioxidant phenolic constituents of olive oil, after intravenous and oral dosing of labeled compounds to rats. Journal of Nutrition 131, 1993-1996.
145. Tuck KL & Hayball PJ (2002) Major phenolic compounds in olive oil: metabolism and health effects. Journal of Nutritional Biochemistry 13, 636-644.
146. van Dyke BR & Saltman P (1996) Hemoglobin: a mechanism for the generation of hydroxyl radicals. Free Radical Biology and Medicine 20, 985-989.
147. Vasquez Roncero A (1978) Les polyphenols de l'huile d'olive et leur influence sur les characteristiques de l'huile (Polyphenols of olive oil and their influence on oil characteristics). Revue Française des Corps Gras 25, 21-26.
148. Venkatasubbaiah P & Chilton WS (1990) Phytotoxins of Botryosphaeria obtusa. Journal of Natural Products 53, 1628-1630.
149. Vieira O, Laranjinha J, Madeira V & Almeida L (1998) Cholesteryl ester hydroperoxide formation in myoglobin-catalyzed low density lipoprotein oxidation: concerted antioxidant activity of caffeic and p-coumaric acids with ascorbate. Biochemical Pharmacology 55, 333-340.
150. Visioli F (2000) Antioxidants in Mediterranean diets. World Review of Nutrition and Dietetics 87, 43-55.
151. Visioli F, Bellomo G, Montedoro GF & Galli C (1995a) Low density lipoprotein oxidation is inhibited in vitro by olive oil constituents. Atherosclerosis 117, 25-32.
152. Visioli F, Bellomo GF & Galli C (1998) Free radical scavenging properties of olive oil polyphenols. Biochemical and Biophysical Research Communications 247, 60-64.
153. Visioli F, Bordone R, Perugini C, Bagnati M, Cau C & Bellomo G (2000a) The kinetics of copper-induced LDL oxidation depend upon its lipid composition and antioxidant content. Biochemical and Biophysical Research Communications 268, 818-822.
154. Visioli F, Borsani L & Galli C (2000b) Diet and prevention of coronary heart disease: the potential role of phytochemicals. Cardiovascular Research 47, 419-425.
155. Visioli F & Galli C (1998a) Olive oil phenols and their potential effects on human health. Journal of Agricultural and Food Chemistry 46, 4292-4296.
156. Visioli F & Galli C (1998b) The effect of minor constituents of olive oil on cardiovascular disease: new findings. Nutrition Reviews 56, 142-147.
157. Visioli F & Galli C (2001) Antiatherogenic components of olive/olive oil. Current Atherosclerosis Reports 3, 64-67.
158. Visioli F, Galli C, Bornet F, Mattei A, Patelli R, Galli G & Caruso D (2000c) Olive oil phenolics are dose-dependently absorbed in humans. FEBS Letters 468, 159-160.
159. Visioli F, Poli A & Galli C (2002) Antioxidant and other biological activities of phenols from olives and olive oil. Medicinal Research Reviews 22, 65-75.
160. Visioli F, Vinceri FF & Galli C (1995e) "Waste waters" from olive oil production are rich in natural antioxidants. Experientia 51, 32-34.
161. Walter WM Jr, Hemming HP & Etchells JL (1973) Preparation of antimicrobial compounds by hydrolysis of oleuropein from green olives. Applied Microbiology 26, 773-776.
162. Wang C, Mäkelä T, Hase T, Adlercreutz H & Kurzer MS (1994) Lignans and flavonoids inhibit aromatase enzyme in human preadipocytes. Journal of Steroid Biochemistry and Molecular Biology 50, 205-212.
163. Willet WC, Sacks S, Trichopoulou A, Drescher G, Ferro-Luzzi A, Helsinf E & Trichopoulos D (1995) Mediterranean diet pyramid: a cultural model for healthy eating. American Journal of Clinical Nutrition 61, 1402-1406.
164. Wiseman SA, Mathot JNNJ, De Fouw NJ & Tijburg LBM (1996) Dietary non-tocopherol antioxidants present in extra virgin olive oil increase the resistance of low density lipoproteins to oxidation in rabbits. Atherosclerosis 120, 15-23.
165. 2+-induced low-density lipoprotein oxidation in propagation phase. FEBS Letters 401, 230-234.
166. Yermilov V, Rubio J & Ohshima H (1995) Formation of 8-nitroguanine in DNA treated with peroxynitrite in vitro and its rapid removal from DNA by depurination. FEBS Letters 376, 207-210.