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Biological Activities of Phenolic Compounds Present in Virgin Olive Oil

Sara Cicerale, Lisa Lucas, Russell Keast

International Journal of Molecular Sciences · 2010 · Review · CC BY

doi:10.3390/ijms11020458

Abstract

The Mediterranean diet is associated with a lower incidence of atherosclerosis, cardiovascular disease, neurodegenerative diseases and certain types of cancer. The apparent health benefits have been partially ascribed to the dietary consumption of virgin olive oil by Mediterranean populations. Much research has focused on the biologically active phenolic compounds naturally present in virgin olive oils to aid in explaining reduced mortality and morbidity experienced by people consuming a traditional Mediterranean diet. Studies (human, animal, in vivo and in vitro) have demonstrated that olive oil phenolic compounds have positive effects on certain physiological parameters, such as plasma lipoproteins, oxidative damage, inflammatory markers, platelet and cellular function, antimicrobial activity and bone health. This paper summarizes current knowledge on the bioavailability and biological activities of olive oil phenolic compounds.

Full text

From PubMed Central, U.S. National Library of Medicine, as current on Oct 18, 2026. Paragraph numbers are ours, so an answer can point at one.

Introduction

A lower prevalence of non-communicable diseases such as cardiovascular disease and certain types of cancers have been demonstrated in countries residing in the Mediterranean region in comparison to other parts of the world. This lowered incidence has been partially attributed to the regular intake of virgin olive oil as part of a traditional Mediterranean diet. Dietary consumption of virgin olive oil in a Mediterranean diet typically ranges between 25–50 mL per day.

Virgin olive oil is produced from the first and second pressings of the olive fruit by the cold-pressing method (where no chemicals and only a small amount of heat are applied) and is composed of a glycerol fraction (making up 90–99% of the olive fruit) and a non-glycerol or unsaponifiable fraction (making up 0.4–5% of the olive fruit) which contains phenolic compounds. Historically, the beneficial health effects of virgin olive oil intake were attributed to the glycerol fraction with its high concentration of monounsaturated fatty acids (MUFAs) (particularly oleic acid). However, several seed oils (including sunflower, soybean, and rapeseed) containing high quantities of MUFAs are ineffective in beneficially altering chronic disease risk factors. Therefore, a substantial number of investigations examining the biological actions of olive oil phenolic compounds in the unsaponifiable fraction have been conducted. In this paper, the term virgin olive oil will be used to describe both extra virgin and virgin olive oil.

Studies conducted thus far (including human, animal, in vivo and in vitro) have demonstrated that olive oil phenolic compounds have positive effects on various physiological biomarkers, implicating phenolic compounds as partially responsible for health benefits associated with the Mediterranean diet. Furthermore, olive oil phenolic compounds have been shown to be highly bioavailable, reinforcing their potential health promoting properties.

The phenolic fraction of virgin olive oil is heterogeneous, with at least 36 structurally distinct phenolic compounds identified. Variation in the phenolic concentration exists between differing virgin olive oils due to numerous factors including: variety of the olive fruit, region in which the olive fruit is grown, agricultural techniques used to cultivate the olive fruit, maturity of the olive fruit at harvest, and olive oil extraction, processing, storage methods and time since harvest. Cooking methods have also been shown to alter phenolic concentrations in virgin olive oil. Finally, research has shown that the analytical method used to quantify the concentration of phenolic compounds present in virgin olive oil has an influence on the reported concentration. The factors mentioned above are not discussed in the current paper. For an extensive review on the matter, please see the paper by Cicerale and colleagues. Therefore, the objective of the current paper was to review the bioavailability of olive oil phenolic compounds and the biological activities associated with them.

Bioavailability of Olive Oil Phenolic Compounds

The bioavailability of a compound refers to the degree in which it is extracted from a food matrix and absorbed by the body. The majority of research regarding the bioavailability of olive oil phenolic compounds has focused on three major phenolics: hydroxytyrosol, tyrosol, and oleuropein, and in general, phenolics from virgin olive oil have been demonstrated to be readily bioavailable.

Research has shown that the phenolic compounds, hydroxytyrosol and tyrosol are absorbed after ingestion in a dose-dependent manner. Tuck and colleagues demonstrated increased bioavailability of hydroxytyrosol and tyrosol when administered as an olive oil solution compared to an aqueous solution. The differences in bioavailability have been suggested to be due to the high antioxidant content of virgin olive oil compared to water and this high antioxidant content may have protected the breakdown of phenolics in the gastrointestinal tract prior to absorption. A further study found that absorption of administered ligstroside-aglycone, hydroxytyrosol, tyrosol, and oleuropein-aglycone was as high as 55–66% in humans. Finally, oleuropein was demonstrated to be somewhat absorbed from isolated perfused rat intestine. The mechanism by which absorption occurs with regards to olive oil phenolic compounds remains unclear. However, the different polarities of the various phenolics has been postulated to play a role in the absorption of these compounds. For instance, the phenolics tyrosol and hydroxytyrosol are polar compounds and their absorption has been postulated to occur via passive diffusion. The polar but larger phenolic, oleuropein-glycoside may be absorbed via a different mechanism to tyrosol and hydroxytyrosol. It has been proposed that oleuropein-glycoside may diffuse through the lipid bilayer of the epithelial cell membrane and be absorbed via a glucose transporter. Two additional mechanisms for oleuropein-glycoside absorption are potentially via the paracellular route or transcellular passive diffusion. The phenolics, oleuropein and ligstroside-aglycones are less polar and currently there is no data available on their mechanism of absorption. Further research is required to substantiate the mechanisms of absorption for these phenolics and further investigate the mechanisms for other phenolic compounds.

Studies examining the quantity of phenolics excreted have also been carried out. A low quantity of phenolics present in urine after ingestion would indicate that these phenolics are readily absorbed. Excreted phenolics (mainly in the form of hydroxytyrosol and tyrosol) were determined to be 5–16% of the total ingested. Excretion of approximately 24% of administered tyrosol was demonstrated in a study by Miro-Cases and colleagues. Finally, Visioli and colleagues reported the excretion of administered hydroxytyrosol and tyrosol to be between 30–60% and 20–22% of the total ingested by human subjects, respectively. The above findings demonstrate that humans absorb a significant portion (~40–95%, using hydroxytyrosol and tyrosol as proxy) of the dietary olive oil phenolic compounds they consume. As most of the data is only based on three phenolics, more research is required on the excretion of other key phenolics in virgin olive oil.

The metabolism of olive oil phenolic compounds is important in determining their availability. If phenolics are broken down and converted to other phenolics this may have a notable effect on their bioavailability. Phenolic compounds, oleuropein-glycoside and oleuropein and ligstroside-aglycones are converted to hydroxytyrosol or tyrosol and excreted in urine. Hydroxytyrosol and tyrosol themselves are sometimes conjugated to glucuronic acid and excreted in urine as glucuronides. However, further work is needed in this area.

Olive Oil Phenolic Compounds and Health

Human and animal research have shown that olive oil phenolic compound’s possess important biological activities that may exert a preventative effect in regards to the development of chronic degenerative diseases. Figure 1 demonstrates the biological activities exerted by olive oil phenolic compounds. Table 1 briefly summarizes the findings of several human studies that have investigated the biological activities of olive oil phenolic compounds.

Olive Oil Phenolic Compounds and Their Beneficial Effect on Plasma Lipoproteins

Elevated levels of total cholesterol (TC) and low density lipoprotein cholesterol (LDL-C) have been established as risk factors for atherosclerosis, which is the primary cause of cardiovascular disease (CVD). However, on the other hand, elevated high density lipoprotein cholesterol (HDL-C) levels are believed to have protective, anti-inflammatory properties. Data from a controlled human study containing 200 healthy male subjects, found a decrease in TC to HDL-C ratio with increasing phenolic content of the virgin olive oil consumed. An increase in HDL-C was also noted with increasing phenolic concentration of the oil. Consumption of phenol rich virgin olive oils have resulted in increases in circulating HDL-C ranging between 5.1–6.7% in two further human studies. Additionally, an earlier study showed a significant decrease in LDL-C after one week of phenol rich virgin olive oil consumption. There are three human studies that showed olive oil phenolic compounds had no effect on blood lipid composition. These studies used people with mild dyslipidemia and peripheral vascular disease (as opposed to healthy subjects used in the other studies) in two of the three studies and in the third study the authors propose the three week study period may not have been long enough to observe a treatment effect. However, it should be noted that in one study, four days was ample time to see a change in HDL-C.

Studies involving animals have demonstrated that ingestion of phenol rich virgin olive oil led to improvements in blood lipid profile. A study involving rabbits demonstrated a reduction in circulating TC and an increase in HDL-C upon virgin olive oil consumption. Furthermore, studies in rats have found that the intake of phenol rich virgin olive oil decreases TC, LDL-C and triglyceride (TG) levels and substantially increases HDL-C concentrations.

Olive Oil Phenolic Compounds and Their Beneficial Effect on Lipid Oxidation

LDL oxidation (oxLDL) is considered to be a major risk factor for the development of atherosclerosis and CVD. Oxidation of LDL causes damage to the vascular wall, stimulating macrophage uptake and formation of foam cells, which in turn result in the formation of plaque within the arterial wall. Both human and animal in vivo studies have shown that the level at which LDL oxidizes, decreases linearly with increasing phenolic concentration. Two further mechanistic studies, demonstrated that phenolic compounds are able to bind to LDL and the authors suggest that this may account for the increase in LDL resistance to oxidation. Although it is important to note that there have been conflicting results from three short term studies suggesting that the phenolic content of the virgin olive oil does not play a role in the lowering of oxLDL. In addition, in vitro studies have found that the phenolic compounds extracted from virgin olive oil inhibit the oxidation of LDL-C.

Olive Oil Phenolic Compounds and Their Beneficial Effect on Oxidative DNA Damage

Oxidative damage to DNA is a precursor for human carcinogenesis and it is well known that oxygen radicals continually attack human cells. Unless damage to these cells is counteracted, DNA damage may result, and such damage can lead to cancer development. A randomized crossover intervention trial has shown that intake of phenol rich virgin olive oil decreases oxidative DNA damage by up to 30% compared to a low phenol virgin olive oil. An additional study also demonstrated that after consumption of phenol rich virgin olive oil there was decreased urinary excretion of 8-oxo-deoxygyuanosine (8oxodG) a systemic marker of DNA oxidation.

In support of these findings, animal studies have also reported that a diet enriched with olive oil phenolic compounds has a protective effect against DNA damage. In agreement with these findings, a recent in vitro study reported that olive oil phenolic compounds showed DNA oxidation preventative activity.

Olive Oil Phenolic Compounds and Their Beneficial Effect on Additional Markers of Oxidation

Oxidative stress produced by reactive oxygen species (ROS) has been linked to a number of diseases such as atherosclerosis, certain cancers and neurodegenerative diseases and is considered as a by-product of aerobic metabolism. Goya et al. treated a sample of human hepatoma HepG2 cells with hydroxytyrosol and found that there was a decrease in ROS production. Similarly olive oil phenolic compounds have been shown to scavenge ROS under natural and chemically simulated oxidative stress conditions. A further study by Moreno et al. demonstrated that tyrosol modulated ROS production, in murine macrophages.

Total plasma antioxidant activity has also been reported to increase in humans after the ingestion of olive oil phenolic compounds. However, one study did not report an increase in the total blood antioxidant capacity.

Oxidative stress can be indicated by the presence of markers such as F2-isoprostanes, lipid peroxides (LPO), oxidized gluthathione (GSSG), reduced gluthathione (GSH) and glutathione peroxidase (GSH-Px). F2-isoprostanes are a result of the free radical induced peroxidation of arachidonic acid. LPO is more than likely a by-product of the oxidation of fatty acids and depletion of the protective GSH precedes lipid oxidation and atherogenesis in vivo.

Human studies have shown beneficial effects of olive oil phenolic compounds on these aforementioned markers of oxidative stress. A randomized cross over study found the intake of a olive oil phenolic-enriched breakfast significantly lowered F2-isoprostane levels compared to a low phenolic-enriched breakfast. Visioli and colleagues demonstrated that consumption of a phenolic-rich virgin olive oil was associated with a significant decrease in urinary excretion of F2-isoprostanes. Another human study did not find an effect of olive oil phenolics on F2-isoprostane levels, this may be possibly due to the considerably low phenolic content of the oil administered (166 mg/kg) compared to a phenolic content up 1950 mg/kg in the Visioli et al. study. An animal study also found that administration of hydroxytyrosol-containing olive oil waste water to rats exposed to cigarette smoke, lowered F2-isoprostane levels significantly (p < 0.05).

Covas and colleagues found that phenol-rich virgin olive oil beneficially modulated the balance between GSH and GSSG, while Weinbrenner and colleagues found an increase in GSH-Px after phenol-rich virgin olive oil administration in human subjects. Moreover, a decrease in LPO after olive oil phenolic administration has been noted. More recently, olive oil phenolic compounds sourced from olive mill waste water were found to increase GSH concentrations in human blood. Two further studies have also shown that olive oil phenolic compounds reduce oxidative damage to both red blood cells and renal cells.

Olive Oil Phenolic Compounds and Their Beneficial Effect on Markers of Inflammation

Elevated concentrations of inflammation markers in serum are associated with increased cardiovascular risk. Plasma thromboxane B2 (TXB2) and leukotriene B4 (LTB4) are known pro-inflammatory agents. TXB2 has the ability to increase blood platelet aggregation and LTB4 has a chemostactic effect on neutrophils, directing the cells to damaged tissue. These inflammatory agents are known to produce the pain, redness and swelling associated with inflammation. Bogani and colleagues found a decrease in TXB2 and LTB4 concentrations with increasing phenolic concentration of the olive oil. These results were also in accordance with previous investigations.

The inflammatory markers, Interleukin-6 (IL-6) and C-reactive protein (CRP) have been shown to be predictors for CVD also. IL-6 is a pro-inflammatory agent that stimulates inflammation in response to trauma and CRP generally rises when inflammation is present. Fito and colleagues found that consumption of olive oil phenolic compounds from a daily dose of virgin olive oil decreased the circulating concentrations of both IL-6 and CRP in 28 stable coronary heart patients.

In vitro study findings also support the anti-inflammatory capacity of olive oil phenolic compounds. Olive oil phenolics have been found to decrease arachidonic acid release and arachidonic acid metabolite synthesis in vitro and both of these are involved in the inflammatory process. The olive oil phenolic compound, oleocanthal was shown to inhibit cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) activity (both involved in the inflammatory process) in the same way as the anti-inflammatory drug, ibuprofen does. Inhibition of COX enzymes results in the reduction of arachidonate to the eicosanoids, prostaglandins and thromboxane, in the inflammatory pathway.

Olive Oil Phenolic Compounds and Their Beneficial Effect on Platelet Function

Blood platelets have been demonstrated to play a role in CVD and atherosclerosis development. Continual damage to the vascular epithelium results in the development of lesions and these lesions stimulate endothelial adhesion molecule expression, platelet activity and aggregation. Circulating monocytes are attracted by these particular molecules and adhere to the endothelium and differentiate into macrophages, which in turn scavenge LDL and triglyceride (TG) rich lipoproteins, becoming foam cells and forming fatty streaks.

Olive oil phenolic compounds have been shown to inhibit endothelial adhesion molecule expression upon incubation with human umbilical vein endothelial cells. They also have been demonstrated to inhibit human platelet activity in vitro. The phenolic compound, hydroxytyrosol has been noted to completely inhibit platelet aggregation in human blood (in vitro) in the range of 100–400 μM. A more recent investigation, demonstrated that a number of olive oil phenolic compounds (such as oleuropein aglycone and luteolin) also were potent inhibitors of platelet aggregation. Virgin olive oil containing a high content (400 mg/kg) of phenolic compounds has been demonstrated to also decrease plasminogen activator inhibitor-1 (PAI-1) and factor VII (FVII). Both PAI-1 and FVII are pro-coagulant factors that have been linked to the development of coronary heart disease (CHD). Furthermore, olive oil phenolics have been shown to decrease homocysteine, which has been linked to increased adhesiveness of the endothelium.

Olive Oil Phenolic Compounds and Their Beneficial Effect on Cellular Function

Cell proliferation and suppressed cell death are underlying factors for tumor formation and progression. Research to date has shown that the olive oil phenolic, hydroxytyrosol inhibits cell proliferation in human promyelocytic HL60 leukemia cells and in human colon cancer lines. Hashim and colleagues demonstrated a dose-related inhibition of colon cancer cell invasion by olive oil phenolic compounds. Also, hydroxytyrosol has been found to exert strong anti-proliferative effects against human colon adenocarcinoma cells. More recently, research using MCF-7 and SKBR3 breast cancer cells showed that phenolic compounds inhibit cell growth in these cell lines in a dose dependent manner and reduce expression of the HER2 oncogene which plays a integral role in malignant transformation, tumorigenesis, and metastasis. Furthermore, oleuropein and hydroxytyrosol have been show to induce cell death of MCF-7 human breast cancer cells. Olive oil phenolics have also been found to improve cell integrity and viability in CaCo2 cells.

The olive oil phenolic compound, oleocanthal has been implicated in the reduced incidence of Alzheimer’s disease in Mediterranean populations via two mechanisms. First, in Alzheimer’s disease a microtubule-associated protein (Tau) involved in the promotion of microtubule assembly and stability begin to aggregate into neurofibrillary tangles. Li and colleagues demonstrated that oleocanthal inhibits tau aggregation. Second, beta-amyloid (Aβ) oligomers (also referred to as ADDLs) have also been suggested to be involved in the development of Alzheimer’s disease. These ADDLs are believed to bind to postsynaptic sites and cause synaptic and neuronal loss. Pitt and colleagues have demonstrated that oleocanthal has the capacity to alter the oligomerization state of ADDLs whilst protecting neurons from the synaptopathological effects of ADDLs. Thus, oleocanthal protects neurons from ADDL induced synaptic deterioration and additionally promotes the antibody clearance of ADDLs. A further study demonstrated the neuro-protection of hydroxytyrosol in rat brains. In this study it was found that hydroxytyrosol reduced lactate dehydrogenase activity which has been closely related with a reduction in brain lipid peroxidation.

Olive Oil Phenolic Compounds and Their Beneficial Effect on Microbial Activity

In vitro research has shown that olive oil phenolic compounds have antimicrobial properties. Particularly, the phenolic compounds, oleuropein, hydroxytyrosol and tyrosol have demonstrated potent antimicrobial activity against several strains of bacteria responsible for intestinal and respiratory infections. Romero and colleagues found that the dialdehydic form of decarboxymethyl ligstroside is not hydrolyzed in the stomach and therefore aids in inhibiting the growth of Helicobacter pylori bacteria. Helicobacter pylori bacteria are linked to the development of peptic ulcers and some types of gastric cancer. Hydroxytyrosol and oleuropein have also been shown to be cytotoxic to a large number of bacterial strains.

Olive Oil Phenolic Compounds and Their Beneficial Effect on Bone

One study to date has investigated the effect of olive oil phenolic compounds on bone. In this study, both tyrosol and hydroxytyrosol increased bone formation in rats significantly. Further studies are now required to substantiate these findings.

Conclusions

In conclusion, olive oil phenolic compounds are highly bioavailable in humans. The high bioavailability of such compounds lends support to evidence that these phenolic components exert beneficial effects on health. Although, the beneficial health effects of virgin olive oil ingestion are well known, it is only recent that that the biological properties of olive oil phenolic compounds have been investigated. In experimental studies (in vivo and in vitro), olive oil phenolic compounds have been shown to beneficially alter lipid composition, platelet and cellular function, microbial activity and bone formation, as well as reduce oxidative damage and inflammation. The modes of action detailed in the paper, may explain the low rate of diet-related diseases amongst populations residing in the Mediterranean region. For example, the anti-atherogenic effects associated with the ingestion of virgin olive oil may explain the low rate of cardiovascular disease in Mediterranean populations. Since DNA oxidative damage is a mechanism underlying cancer development, the protective effects of olive oil phenolic compounds may explain some of the differences in cancer incidence between Mediterranean populations and other populations in the world. The anti-inflammatory effects that arise from the ingestion of olive oil phenolic compounds have been shown to provide protection against diseases marked by an inflammatory component. This may, along with other modes of action, partly explain the low rate of CVD mortality and certain types of cancer in populations residing in the Mediterranean. Olive oil phenolic compounds may also be useful in the treatment of some infectious diseases. Finally, although more studies are required, findings demonstrating the beneficial effects of olive oil phenolics in relation to bone health, may aid in partly explaining the low incidence of osteoporosis in populations residing in the Mediterranean area. These biological properties may have a significant impact on population health through the reduction in incidence of chronic degenerative disease development.

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    Gimeno E Castellote AI Lamuela-Raventos RM De la Torre MC Lopez-Sabater MC The effects of harvest and extraction methods on the antioxidant content (phenolics, alpha-tocopherol, and beta-carotene) in virgin olive oilFood Chem2002 78207211

    Not in our library

  46. 46.

    Brenes M Garcia A Garcia P Rios JJ Garrido A Phenolic compounds in Spanish olive oilsJ. Agric. Food Chem1999 4735353540

    Not in our library10.1021/jf990009o

  47. 47.

    Kalua CM Allen MS Bedgood DR Jr Bishop AG Prenzler PD Discrimination of olive oils and fruits into cultivars and maturity stages based on phenolic and volatile compoundsJ. Agric. Food Chem2005 5380548062

    Not in our library10.1021/jf051233i

  48. 48.

    Tovar MJ Motilva MJ Romero MP Changes in the phenolic composition of virgin olive oil from young trees (Olea europaea L. cv. Arbequina) grown under linear irrigation strategiesJ. Agric. Food Chem2001 4955025508

    Not in our library10.1021/jf0102416

  49. 49.

    Ranalli A Ferrante ML De Mattia G Costantini N Analytical evaluation of virgin olive oil of first and second extractionJ. Agric. Food Chem1999 47417424

    Not in our library10.1021/jf9800256

  50. 50.

    Kalua CM Bedgood DR Jr Bishop AG Prenzler PD Changes in volatile and phenolic compounds with malaxation time and temperature during virgin olive oil productionJ. Agric. Food Chem2006 5476417651

    Not in our library10.1021/jf061122z

  51. 51.

    Mailer RJ Ayton J Comparison of olive oil (Olea europaea) quality extracted by stonemill and hammermillNZ. J. Crop Hort. Sci2004 32325330

    Not in our library

  52. 52.

    Fregapane G Lavelli V Leon S Kapuralin J Desamparados Salvador M Effect of filtration on virgin olive oil stability during storageEur. J. Lip. Sci. Technol2006 108134142

    Not in our library

  53. 53.

    Di Giovacchino L Sestili S Di Vincenzo D Influence of olive processing on virgin olive oil qualityEur. J. Lip. Sci. Technol2002 104587601

    Not in our library

  54. 54.

    Brenes M Garcia A Garcia P Garrido A Acid hydrolysis of secoiridoid aglycons during storage of virgin olive oilJ. Agric. Food Chem2001 4956095614

    Not in our library10.1021/jf0107860

  55. 55.

    Gutierrez F Fernandez JL Determinant parameters and components in the storage of virgin olive oil. Prediction of storage time beyond which the oil is no longer of “extra” qualityJ. Agric. Food Chem2002 50571577

    Not in our library10.1021/jf0102158

  56. 56.

    Okogeri O Tasioula-Margari M Changes occurring in phenolic compounds and alpha-tocopherol of virgin olive oil during storageJ. Agric. Food Chem2002 5010771080

    Not in our library10.1021/jf010895e

  57. 57.

    Rastrelli L Passi S Ippolito F Vacca G De Simone F Rate of degradation of alpha-tocopherol, squalene, phenolics, and polyunsaturated fatty acids in olive oil during different storage conditionsJ. Agric. Food Chem2002 5055665570

    Not in our library10.1021/jf011063j

  58. 58.

    Brenes M Garcia A Dobarganes MC Velasco J Romero C Influence of thermal treatments simulating cooking processes on the polyphenol content in virgin olive oilJ. Agric. Food Chem2002 5059625967

    Not in our library10.1021/jf020506w

  59. 59.

    Gomez-Alonso S Fregapane G Salvador MD Gordon MH Changes in phenolic composition and antioxidant activity of virgin olive oil during fryingJ. Agric. Food Chem2003 51667672

    Not in our library10.1021/jf025932w

  60. 60.

    Cicerale S Conlan XA Barnett NW Sinclair AJ Keast RS Influence of heat on biological activity and concentration of oleocanthal—A natural anti-inflammatory agent in virgin olive oilJ. Agric. Food Chem2009 5713261330

    Not in our library10.1021/jf803154w

  61. 61.

    Carrasco-Pancorbo A Cerretani L Bendini A Segura-Carretero A Gallina-Toschi T Fernandez-Gutierez A Analytical determination of polyphenols in olive oilsJ Sep Sci2005 28837858

    Not in our library10.1002/jssc.200500032

  62. 62.

    Cicerale S Conlan XA Sinclair AJ Keast RSJ Chemistry and health of olive oil phenolicsCrit. Rev. Food Sci. Nutr2009 49218236

    Not in our library10.1080/10408390701856223

  63. 63.

    Martini FH Fundamentals of Anatomy and Physiology7 edPearson Education IncSan Francisco, CA, USA2006

    Not in our library

  64. 64.

    Visioli F Galli C Plasmati E Viappiani S Hernandez A Colombo C Sala A Olive phenol hydroxytyrosol prevents passive smoking-induced oxidative stressCirculation2000 10221692171

    Not in our library10.1161/01.cir.102.18.2169

  65. 65.

    Caruso D Visioli F Patelli R Galli C Galli G Urinary excretion of olive oil phenols and their metabolites in humansMetabolism2001 5014261428

    Not in our library10.1053/meta.2001.28073

  66. 66.

    Tuck KL Freeman MP Hayball PJ Stretch GL Stupans I The in vivo fate of hydroxytyrosol and tyrosol, antioxidant phenolic constituents of olive oil, after intravenous and oral dosing of labeled compounds to ratsJ. Nutr2001 13119931996

    Not in our library10.1093/jn/131.7.1993

  67. 67.

    Edgecombe S Stretch GL Hayball PJ Oleuropein, an antioxidant polyphenol from olive oil, is poorly absorbed from isolated perfused rat intestineJ. Nutr2000 13029963002

    Not in our library10.1093/jn/130.12.2996

  68. 68.

    Manna C Galletti P Maisto G Cucciolla V D’Angelo S Zappia V Transport mechanism and metabolsi of olive oil hydroxytyrosol in Caco-2 cellsFEBS Letters2000 470341344

    Not in our library10.1016/s0014-5793(00)01350-8

  69. 69.

    Visioli F Caruso D Plasmati E Patelli R Mulinacci N Romani A Galli G Galli C Hydroxytyrosol, as a component of olive mill waste water, is dose- dependently absorbed and increases the antioxidant capacity of rat plasmaFree Rad. Res2001 34301305

    Not in our library10.1080/10715760100300271

  70. 70.

    Fito M Cladellas M de la Torre R Marti J Munoz D Schroder H Alcantara M Pujadas-Bastardes M Marrugat J Lopez-Sabater MC Bruguera J Covas MI Anti-inflammatory effect of virgin olive oil in stable coronary disease patients: a randomized, crossover, controlled trialEur. J. Clin. Nutr2008 62570574

    Not in our library10.1038/sj.ejcn.1602724

  71. 71.

    Ruano J Lopez-Miranda J de la Torre R Delgado-Lista J Fernandez J Caballero J Covas MI Jimenez Y Perez-Martinez P Marin C Fuentes F Perez-Jimenez F Intake of phenol-rich virgin olive oil improves the postprandial prothrombotic profile in hypercholesterolemic patientsAm. J. Clin. Nutr2007 86341346

    Not in our library10.1093/ajcn/86.2.341

  72. 72.

    Gimeno E de la Torre-Carbot K Lamuela-Raventos RM Castellote AI Fito M de la Torre R Covas MI Carmen Lopez-Sabater M Changes in the phenolic content of low density lipoprotein after olive oil consumption in men. A randomized crossover controlled trialBr J Nutr2007 18

    Not in our library10.1017/s0007114507778698

  73. 73.

    Bogani P Galli C Villa M Visioli F Postprandial anti-inflammatory and antioxidant effects of extra virgin olive oilAtherosclerosis2007 190181186

    Not in our library10.1016/j.atherosclerosis.2006.01.011

  74. 74.

    Salvini S Sera F Caruso D Giovannelli L Visioli F Saieva C Masala G Ceroti M Giovacchini V Pitozzi V Galli C Romani A Mulinacci N Bortolomeazzi R Dolara P Palli D Daily consumption of a high-phenol extra-virgin olive oil reduces oxidative DNA damage in postmenopausal womenBr. J. Nutr2006 95742751

    Not in our library10.1079/bjn20051674

  75. 75.

    Covas MI de la Torre K Farre-Albaladejo M Kaikkonen J Fito M Lopez-Sabater C Pujadas-Bastardes MA Joglar J Weinbrenner T Lamuela-Raventos RM de la Torre R Postprandial LDL phenolic content and LDL oxidation are modulated by olive oil phenolic compounds in humansFree Rad. Biol. Med2006 40608616

    Not in our library10.1016/j.freeradbiomed.2005.09.027

  76. 76.

    Ruano J Lopez-Miranda J Fuentes F Moreno JA Bellido C Perez-Martinez P Lozano A Gomez P Jimenez Y Perez Jimenez F Phenolic content of virgin olive oil improves ischemic reactive hyperemia in hypercholesterolemic patientsJ. Am. Coll. Cardiol2005 4618641868

    Not in our library10.1016/j.jacc.2005.06.078

  77. 77.

    Visioli F Caruso D Grande S Bosisio R Villa M Galli G Sirtori C Galli C Virgin Olive Oil Study (VOLOS): Vasoprotective potential of extra virgin olive oil in mildly dyslipidemic patientsEur. J. Nutr2005 44121127

    Not in our library10.1007/s00394-004-0504-0

  78. 78.

    Fito M Cladellas M de la Torre R Marti J Alcantara M Pujadas-Bastardes M Marrugat J Bruguera J Lopez-Sabater MC Vila J Covas MI Antioxidant effect of virgin olive oil in patients with stable coronary heart disease: a randomized, crossover, controlled, clinical trialAtherosclerosis2005 181149158

    Not in our library10.1016/j.atherosclerosis.2004.12.036

  79. 79.

    Marrugat J Covas MI Fito M Schroder H Miro-Casas E Gimeno E Lopez-Sabater MC de la Torre R Farre M Effects of differing phenolic content in dietary olive oils on lipids and LDL oxidation–a randomized controlled trialEur. J. Nutr2004 43140147

    Not in our library10.1007/s00394-004-0452-8

  80. 80.

    Weinbrenner T Fito M de la Torre R Saez GT Rijken P Tormos C Coolen S Albaladejo MF Abanades S Schroder H Marrugat J Covas MI Olive oils high in phenolic compounds modulate oxidative/antioxidative status in menJ. Nutr2004 13423142321

    Not in our library10.1093/jn/134.9.2314

  81. 81.

    Moschandreas J Vissers MN Wiseman S van Putte KP Kafatos A Extra virgin olive oil phenols and markers of oxidation in Greek smokers: a randomized cross-over studyEur. J. Clin. Nutr2002 5610241029

    Not in our library10.1038/sj.ejcn.1601444

  82. 82.

    Vissers MN Zock PL Wiseman SA Meyboom S Katan MB Effect of phenol-rich extra virgin olive oil on markers of oxidation in healthy volunteersEur. J. Clin. Nutr2001 55334341

    Not in our library10.1038/sj.ejcn.1601161

  83. 83.

    Bonanome A Pagnan A Caruso D Toia A Xamin A Fedeli E Berra B Zamburlini A Ursini F Galli G Evidence of postprandial absorption of olive oil phenols in humansNutr. Metab. Cardiovas. Dis2000 10111120

    Not in our library

  84. 84.

    Ramirez-Tortosa MC Urbano G Lopez-Jurado M Nestares T Gomez MC Mir A Ros E Mataix J Gil A Extra-virgin olive oil increases the resistance of LDL to oxidation more than refined olive oil in free-living men with peripheral vascular diseaseJ. Nutr1999 12921772183

    Not in our library10.1093/jn/129.12.2177

  85. 85.

    Gordon T Kannel WB Castelli WP Dawber TR Lipoproteins, cardiovascular disease, and death. The Framingham studyArch. Intern. Med1981 14111281131

    Not in our library

  86. 86.

    Chrysohoou C Pitsavos C Skoumas J Masoura C Katinioti A Panagiotakos D Stefanadis C The emerging anti-inflammatory role of HDL-cholesterol, illustrated in cardiovascular disease free population; the ATTICA studyInt. J. Cardio2006 1222933

    Not in our library10.1016/j.ijcard.2006.11.010

  87. 87.

    Gimeno E Fito M Lamuela-Raventos RM Castellote AI Covas M Farre M de La Torre-Boronat MC Lopez-Sabater MC Effect of ingestion of virgin olive oil on human low-density lipoprotein compositionEur. J. Clin. Nutr2002 56114120

    Not in our library10.1038/sj.ejcn.1601293

  88. 88.

    Gorinstein S Leontowicz H Lojek A Leontowicz M Ciz M Krzeminski R Gralak M Czerwinski J Jastrzebski Z Trakhtenberg S Grigelmo-Miguel N Soliva-Fortuny R Martin-Belloso O Olive oils improve lipid metabolism and increase antioxidant potential in rats fed diets containing cholesterolJ. Agric. Food Chem2002 5061026108

    Not in our library10.1021/jf020306k

  89. 89.

    Mangas-Cruz MA Fernandez-Moyano A Albi T Guinda A Relimpio F Lanzon A Pereira JL Serrera JL Montilla C Astorga R Garcia-Luna PP Effects of minor constituents (non-glyceride compounds) of virgin olive oil on plasma lipid concentrations in male Wistar ratsClin. Nutr2001 20211215

    Not in our library10.1054/clnu.2000.0382

  90. 90.

    Witztum JL The oxidation hypothesis of atherosclerosisLancet1994 344793795

    Not in our library10.1016/s0140-6736(94)92346-9

  91. 91.

    Coni E Di Benedetto R Di Pasquale M Masella R Modesti D Mattei R Carlini EA Protective effect of oleuropein, an olive oil biophenol, on low density lipoprotein oxidizability in rabbitsLipids2000 354554

    Not in our library10.1007/s11745-000-0493-2

  92. 92.

    Patrick L Uzick M Cardiovascular disease: C-reactive protein and the inflammatory disease paradigm: HMG-CoA reductase inhibitors, alpha-tocopherol, red yeast rice, and olive oil polyphenols. A review of the literatureAltern. Med. Rev2001 6248271

    Not in our library

  93. 93.

    Ramirez-Tortosa C Lopez-Pedrosa JM Suarez A Ros E Mataix J Gil A Olive oil- and fish oil-enriched diets modify plasma lipids and susceptibility of LDL to oxidative modification in free-living male patients with peripheral vascular disease: the Spanish Nutrition StudyBr. J. Nutr1999 823139

    Not in our library10.1017/s0007114599001099

  94. 94.

    Ochoa JJ Quiles JL Ramirez-Tortosa C Mataix J Huertas JR Dietary oil high in oleic acid but with different unsaponifiable fraction contents have different effects in fatty acid composition and peroxidation in rabit LDLNutrition2002 186065

    Not in our library10.1016/s0899-9007(01)00732-8

  95. 95.

    De la Torre-Carbot K Chavez-Servin JL Jauregui O Castellote AI Lamuela-Raventos RM Fito M Covas MI Munoz-Aguayo D Lopez-Sabater MC Presence of virgin olive oil phenolic metabolites in human low density lipoprotein fraction: determination by high-performance liquid chromatography-electrospray ionization tandem mass spectrometryAnalyt. Chim. Acta2007 583402410

    Not in our library10.1016/j.aca.2006.10.029

  96. 96.

    Berrougui H Cloutier M Isabelle M Khalil A Phenolic-extract from argan oil (Argania spinosa L.) inhibits human low-density lipoprotein (LDL) oxidation and enhances cholesterol efflux from human THP-1 macrophagesAtherosclerosis2006 184389396

    Not in our library10.1016/j.atherosclerosis.2005.05.018

  97. 97.

    Masella R Vari R D’Archivio M Di Benedetto R Matarrese P Malorni W Scazzocchio B Giovannini C Extra virgin olive oil biophenols inhibit cell-mediated oxidation of LDL by increasing the mRNA transcription of glutathione-related enzymesJ. Nutr2004 134785791

    Not in our library10.1093/jn/134.4.785

  98. 98.

    Visioli F Bellomo G Montedoro G Galli C Low density lipoprotein oxidation is inhibited in vitro by olive oil constituentsAtherosclerosis1995 1172532

    Not in our library10.1016/0021-9150(95)05546-9

  99. 99.

    Cooke MS Evans MD Dizdaroglu M Lunec J Oxidative DNA damage: mechanisms, mutation, and diseaseFed. Am. Soc. Exper. Biol. J2003 1711951214

    Not in our library10.1096/fj.02-0752rev

  100. 100.

    Machowetz A Poulsen HE Gruendel S Weimann A Fito M Marrugat J de la Torre R Salonen JT Nyyssonen K Mursu J Nascetti S Gaddi A Kiesewetter H Baumler H Selmi H Kaikkonen J Zunft HJ Covas MI Koebnick C Effect of olive oils on biomarkers of oxidative DNA stress in Northern and Southern EuropeansFASEB J2007 214552

    Not in our library10.1096/fj.06-6328com

  101. 101.

    Jacomelli M Pitozzi V Zaid M Larrosa M Tonini G Martini A Urbani S Taticchi A Servili M Dolara P Giovannelli L Dietary extra-virgin olive oil rich in phenolic antioxidants and the aging process: long-term effects in the ratJ Nutr Biochem2009 doi:10.1016/j.jnutbio.2008.12.014

    Not in our library10.1016/j.jnutbio.2008.12.014

  102. 102.

    Quiles JL Farquharson AJ Simpson DK Grant I Wahle KW Olive oil phenolics: effects on DNA oxidation and redox enzyme mRNA in prostate cellsBr. J. Nutr2002 88225234

    Not in our library10.1079/bjn2002620

  103. 103.

    Fabiani R Rosignoli P De Bartolomeo A Fuccelli R Servili M Montedoro GF Morozzi G Oxidative DNA damage is prevented by extracts of olive oil, hydroxytyrosol, and other olive phenolic compounds in human blood mononuclear cells and HL60 cellsJ. Nutr2008 13814111416

    Not in our library10.1093/jn/138.8.1411

  104. 104.

    Reinisch N Kiechl S Mayr C Schratzberger P Dunzendorfer S Kahler CM Buratti T Willeit J Wiedermann CJ Association of high plasma antioxidant capacity with new lesion formation in carotid atherosclerosis: a prospective studyEur. J. Clin. Invest1998 28787792

    Not in our library10.1046/j.1365-2362.1998.00357.x

  105. 105.

    Goya L Mateos R Bravo L Effect of the olive oil phenol hydroxytyrosol on human hepatoma HepG2 cells: Protection against oxidative stress induced by tert-butylhydroperoxideEur. J. Nutr2007 467078

    Not in our library10.1007/s00394-006-0633-8

  106. 106.

    De la Puerta R Martinez Dominguez ME Ruiz-Gutierrez V Flavill JA Hoult JR Effects of virgin olive oil phenolics on scavenging of reactive nitrogen species and upon nitrergic neurotransmissionLife Sci2001 6912131222

    Not in our library10.1016/s0024-3205(01)01218-8

  107. 107.

    Owen RW Giacosa A Hull WE Haubner R Spiegelhalder B Bartsch H The antioxidant/anticancer potential of phenolic compounds isolated from olive oilEur. J. Cancer2000 3612351247

    Not in our library10.1016/s0959-8049(00)00103-9

  108. 108.

    Paiva-Martins F Fernandes J Rocha S Nascimento H Vitorino R Amado F Borges F Belo L Santos-Silva A Effects of olive oil polyphenols on erythrocyte oxidative damageMol. Nutr. Food Res2009 53609616

    Not in our library10.1002/mnfr.200800276

  109. 109.

    Moreno JJ Effect of olive oil minor components on oxidative stress and arachidonic acid mobilization and metabolism by macrophagesFree Rad. Biol. Med2003 3510731081

    Not in our library10.1016/s0891-5849(03)00465-9

  110. 110.

    Biswas SK Newby DE Rahman I Megson IL Depressed glutathione synthesis precedes oxidative stress and atherogenesis in Apo-E(–/–) miceBiochem. Biophys. Res. Comm2005 33813681373

    Not in our library10.1016/j.bbrc.2005.10.098

  111. 111.

    Visioli F Wolfram R Richard D Abdullah MICB Crea R Olive phenolics increase glutathione levelsin healthy volunteersJ. Agric. Food Chem2009 5717931796

    Not in our library10.1021/jf8034429

  112. 112.

    Loru D Incani A Deiaa M Corona G Atzeri A Melis MP Rosa A Dessi MA Protective effect of hydroxytyrosol and tyrosol against oxidative stress in kidney cellsToxicol. Ind. Health2009 25301310

    Not in our library10.1177/0748233709103028

  113. 113.

    Packard RRS Libby P Inflammation in atherosclerosis: From vascular biology to biomarker discovery and risk predictionClin. Chem2008 542438

    Not in our library10.1373/clinchem.2007.097360

  114. 114.

    Groff JL Gropper SS Advanced Nutrition and Human Metabolism3rd edWadsworth Thomson LearningBelmont, CA, USA2000

    Not in our library

  115. 115.

    Tiziani A Harvard’s Nursing Guide to DrugsElsevier AustraliaSydney, Australia2006

    Not in our library

  116. 116.

    Leger CL Carbonneau MA Michel F Mas E Monnier L Cristol JP Descomps B A thromboxane effect of a hydroxytyrosol-rich olive oil wastewater extract in patients with uncomplicated type I diabetesEur. J. Clin. Nutr2005 59727730

    Not in our library10.1038/sj.ejcn.1602133

  117. 117.

    Beauchamp GK Keast RS Morel D Lin J Pika J Han Q Lee CH Smith AB Breslin PA Phytochemistry: ibuprofen-like activity in extra-virgin olive oilNature2005 4374546

    Not in our library10.1038/437045a

  118. 118.

    Brody T Nutritional Biochemistry2nd edAcademic PressSan Diego, CA, USA1999

    Not in our library

  119. 119.

    White JG Platelets and atherosclerosisEur J Clin Invest1994 24Suppl 12529

    Not in our library10.1111/j.1365-2362.1994.tb02422.x

  120. 120.

    De La Cruz JP Villalobos MA Carmona JA Martin-Romero M Smith-Agreda JM de la Cuesta FS Antithrombotic potential of olive oil administration in rabbits with elevated cholesterolThromb. Res2000 100305315

    Not in our library10.1016/s0049-3848(00)00321-2

  121. 121.

    Perona JS Cabello-Moruno R Ruiz-Gutierrez V The role of virgin olive oil components in the modulation of endothelial functionJ. Nutr. Biochem2006 17429445

    Not in our library10.1016/j.jnutbio.2005.11.007

  122. 122.

    Togna GI Togna AR Franconi M Marra C Guiso M Olive oil isochromans inhibit human platelet reactivityJ. Nutr2003 13325322536

    Not in our library10.1093/jn/133.8.2532

  123. 123.

    Petroni A Blasevich M Salami M Papini N Montedoro G Galli C Inhibition of platelet aggregation and eicosanoid production by phenolic components of olive oilThromb Res1995 78151160

    Not in our library10.1016/0049-3848(95)00043-7

  124. 124.

    Dell’ Agli M Maschi O Galli GV Fagnani R Dal Cero E Caruso D Bosisio E Inhibition of platelet aggregation by olive oil phenols via cAMP-phosphodiesteraseBr. J. Nutr2008 99945951

    Not in our library10.1017/s0007114507837470

  125. 125.

    Manna C Napoli D Cacciapuoti G Porcelli M Zappia V Olive oil phenolic compounds inhibit homocysteine-induced endothelial cell adhesion regardless of their different antioxidant activityJ. Agric. Food Chem2009 5734783482

    Not in our library10.1021/jf8037659

  126. 126.

    Evan GI Vousden KH Proliferation, cell cycle and apoptosis in cancerNature2001 411342348

    Not in our library10.1038/35077213

  127. 127.

    Fabiani R De Bartolomeo A Rosignoli P Servili M Selvaggini R Montedoro GF Di Saverio C Morozzi G Virgin olive oil phenols inhibit proliferation of human promyelocytic leukemia cells (HL60) by inducing apoptosis and differentiationJ. Nutr2006 136614619

    Not in our library10.1093/jn/136.3.614

  128. 128.

    Gill CI Boyd A McDermott E McCann M Servili M Selvaggini R Taticchi A Esposto S Montedoro G McGlynn H Rowland I Potential anti-cancer effects of virgin olive oil phenols on colorectal carcinogenesis models in vitroInt. J. Cancer2005 11717

    Not in our library10.1002/ijc.21083

  129. 129.

    Fini L Hotchkiss E Fogliano V Graziani G Romano M De Vol EB Qin H Selgrad M Boland CR Ricciardiello L Chemopreventive properties of pinoresinol-rich olive oil involve a selective activation of the ATM-p53 cascade in colon cancer cell linesCarcinogenesis2008 29139146

    Not in our library10.1093/carcin/bgm255

  130. 130.

    Hashim YZ Rowland IR McGlynn H Servili M Selvaggini R Taticchi A Esposto S Montedoro G Kaisalo L Wahala K Gill CI Inhibitory effects of olive oil phenolics on invasion in human colon adenocarcinoma cells in vitroInt. J. Cancer2008 122495500

    Not in our library10.1002/ijc.23148

  131. 131.

    Corona G Deiana M Incani A Vauzour D Dessi MA Spencer JPE Hydroxytyrosol inhibits the proliferation of human colon adeocarcinoma cells through ihibition of ERK1/2 ad cyclin D1Mol. Nutr. Food Res2009 53897903

    Not in our library10.1002/mnfr.200800269

  132. 132.
    Olive oil's bitter principle reverses acquired autoresistance to trastuzumab (Herceptin™) in HER2-overexpressing breast cancer cells · 2007
    No notice
  133. 133.

    Menendez JA Vazquez-Martin A Oliveras-Ferraros C Garcia-Villalba R Carrasco Pancorbo A Fernandez-Gutierez A Segura-Carretero A Analysing effects of extra-virgin olive oil polyphenols on breast cancer-associated fatty acid synthase protein expression using reverse-phase protein microarraysInt. J. Mol. Med2008 22433439

    Not in our library

  134. 134.

    Menendez JA Vazquez-Martin A Oliveras-Ferraros C Garcia-Villalba R Carrasco Pancorbo A Fernandez-Gutierrez A Segura-Carretero A Extra-virgin olive oil polyphenolics inhibit HER2 (erbB-2)-induced malignant transformation in human breast epithelial cells: Relationship between the chemical structures of extra-virgin olive oil secoiridoids and lignans and their inhibitory activities on the tyrosine kinase activity of HER2Int. J. Oncol2009 344351

    Not in our library

  135. 135.

    Han J Talorete TPN Yamada P Isoda H Anti-proliferative and apototic effects of oleuropein and hydroxytyrosol on human breast cancer MCF-7 cellsCytotechnology2009 594553

    Not in our library10.1007/s10616-009-9191-2

  136. 136.

    Manna C Galletti P Cucciolla V Moltedo O Leone A Zappia V The protective effect of the olive oil polyphenol (3,4-dihydroxyphenyl)-ethanol counteracts reactive oxygen metabolite-induced cytotoxicity in Caco-2 cellsJ. Nutr1997 127286292

    Not in our library10.1093/jn/127.2.286

  137. 137.

    Li W Sperry JB Crowe A Trojanowki JQ Smith AB Lee VMY Inhibition of tau fibrillization by oleocanthal via reaction with amino groups of tauJ. Neurochem2009 11013391351

    Not in our library10.1111/j.1471-4159.2009.06224.x

  138. 138.

    Pitt J Roth W Lacor P Blankenship M Velasco P De Felice F Breslin PA Klein WL Alzheimer’s-associated A-beta oligomers show altered structure, immunoreactivity and synaptotoxicity with low doses of oleocanthalToxicol Appl Pharmacol2009 doi:10.1016/j.taap.2009.07.018

    Not in our library10.1016/j.taap.2009.07.018

  139. 139.

    Gonzalez-Correa JA Navas MD Lopez-Villodres JA Trujillo M Espartero JL De la Cruz JP Neuroprotective effect of hydroxytyrosol and hydroxytyrosol acetate in rat brain slices subjected to hypoxia-reoxygeationNeurosci. Lett2008 446143146

    Not in our library10.1016/j.neulet.2008.09.022

  140. 140.

    Medina E de Castro A Romero C Brenes M Comparison of the concentrations of phenolic compounds in olive oils and other plant oils: correlation with antimicrobial activityJ. Agric. Food Chem2006 5449544961

    Not in our library10.1021/jf0602267

  141. 141.

    Romero C Medina E Vargas J Brenes M De Castro A In vitro activity of olive oil polyphenols against Helicobacter pyloriJ. Agric. Food Chem2007 55680686

    Not in our library10.1021/jf0630217

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