Phenolic molecules in virgin olive oils: a survey of their sensory properties, health effects, antioxidant activity and analytical methods. An overview of the last decade.

Among vegetable oils, virgin olive oil (VOO) has nutritional and sensory characteristics that to make it unique and a basic component of the Mediterranean diet. The importance of VOO is mainly attributed both to its high content of oleic acid a balanced contribution quantity of polyunsaturated fatty acids and its richness in phenolic compounds, which act as natural antioxidants and may contribute to the prevention of several human diseases. The polar phenolic compounds of VOO belong to different classes: phenolic acids, phenyl ethyl alcohols, hydroxy-isochromans, flavonoids, lignans and secoiridoids. This latter family of compounds is characteristic of Oleaceae plants and secoiridoids are the main compounds of the phenolic fraction. Many agronomical and technological factors can affect the presence of phenols in VOO. Its shelf life is higher than other vegetable oils, mainly due to the presence of phenolic molecules having a catechol group, such as hydroxytyrosol and its secoiridoid derivatives. Several assays have been used to establish the antioxidant activity of these isolated phenolic compounds. Typical sensory gustative properties of VOO, such as bitterness and pungency, have been attributed to secoiridoid molecules. Considering the importance of the phenolic fraction of VOO, high performance analytical methods have been developed to characterize its complex phenolic pattern. The aim of this review is to realize a survey on phenolic compounds of virgin olive oils bearing in mind their chemical-analytical, healthy and sensory aspects. In particular, starting from the basic studies, the results of researches developed in the last ten years will be focused.

[1]  G. Montedoro,et al.  Inhibition of platelet aggregation and eicosanoid production by phenolic components of olive oil. , 1995, Thrombosis research.

[2]  J. Hoult,et al.  Inhibition of leukocyte 5-lipoxygenase by phenolics from virgin olive oil. , 1999, Biochemical pharmacology.

[3]  A. Escarpa,et al.  An Overview of Analytical Chemistry of Phenolic Compounds in Foods , 2001 .

[4]  A. Coelho,et al.  Phenolic Compounds and Antioxidant Activity of Olea europaea L. Fruits and Leaves , 2006 .

[5]  M. Servili,et al.  Antioxidant activity of tocopherols and phenolic compounds of virgin olive oil , 1996 .

[6]  G. Mellerio,et al.  Characterization of phenolic and secoiridoid aglycons present in virgin olive oil by gas chromatography-chemical ionization mass spectrometry , 1996 .

[7]  H. Sakurai,et al.  Protective effects of hydroxybenzoic acids and their esters on cell damage induced by hydroxyl radicals and hydrogen peroxides. , 1997, Biological & pharmaceutical bulletin.

[8]  G. Bellomo,et al.  Low density lipoprotein oxidation is inhibited in vitro by olive oil constituents. , 1995, Atherosclerosis.

[9]  G. Beauchamp,et al.  Synthesis and assignment of absolute configuration of (-)-oleocanthal: a potent, naturally occurring non-steroidal anti-inflammatory and anti-oxidant agent derived from extra virgin olive oils. , 2005, Organic letters.

[10]  P. Schmitt‐Kopplin,et al.  Capillary electrophoresis – mass spectrometry: Survey on developments and applications 2003–2004 , 2005, Electrophoresis.

[11]  F. Tomás-Barberán,et al.  Determination of phenolic compounds in honeys with different floral origin by capillary zone electrophoresis , 1997 .

[12]  R. de Caterina,et al.  Quenching of Intracellular ROS Generation as a Mechanism for Oleate-Induced Reduction of Endothelial Activation and Early Atherogenesis , 2002, Thrombosis and Haemostasis.

[13]  P. Prenzler,et al.  Quantitative changes in phenolic content during physiological development of the olive (Olea europaea) cultivar Hardy's Mammoth. , 2003, Journal of agricultural and food chemistry.

[14]  B. Dimitrios.  Sources of natural phenolic antioxidants , 2006 .

[15]  M. Servili,et al.  Simple and hydrolyzable compounds in virgin olive oil. 3. Spectroscopic characterizations of the secoiridoid derivatives. , 1993 .

[16]  A. Napoli,et al.  Secondary metabolism of olive secoiridoids. New microcomponents detected in drupes by electrospray ionization and high-resolution tandem mass spectrometry. , 2007, Rapid communications in mass spectrometry : RCM.

[17]  N. Cortesi,et al.  Dosaggio dei componenti minori polari (CMP) in oli vergini di oliva , 1995 .

[18]  E. Lund.  Olive oil phenolics: effects on DNA-oxidation and redox enzyme mRNA in prostate cells , 2002, British Journal of Nutrition.

[19]  T. G. Toschi,et al.  Liquid-liquid and solid-phase extractions of phenols from virgin olive oil and their separation by chromatographic and electrophoretic methods. , 2003, Journal of chromatography. A.

[20]  M. Coimbra,et al.  Characterisation of phenolic extracts from olive pulp and olive pomace by electrospray mass spectrometry , 2005 .

[21]  R. Frazier.  Recent advances in capillary electrophoresis methods for food analysis , 2001, Electrophoresis.

[22]  K. Schwarz,et al.  Effect of the full refining process on rice bran oil composition and its heat stability , 2006 .

[23]  R. Keast,et al.  Phytochemistry: Ibuprofen-like activity in extra-virgin olive oil , 2005, Nature.

[24]  L. Skibsted,et al.  Efficiency of Natural Phenolic Compounds Regenerating α-Tocopherol from α-Tocopheroxyl Radical , 2007 .

[25]  M. Gordon,et al.  Effects of pH and ferric ions on the antioxidant activity of olive polyphenols in oil-in-water emulsions , 2002 .

[26]  A. Segura‐Carretero,et al.  Olive oil's bitter principle reverses acquired autoresistance to trastuzumab (Herceptin™) in HER2-overexpressing breast cancer cells , 2007, BMC Cancer.

[27]  R. Cotter,et al.  Mass Spectrometry , 1992, Bio/Technology.

[28]  R. Aparicio,et al.  Effect of various compounds on virgin olive oil stability measured by Rancimat. , 1999, Journal of agricultural and food chemistry.

[29]  P. Dais,et al.  Novel approach to the detection and quantification of phenolic compounds in olive oil based on 31P nuclear magnetic resonance spectroscopy. , 2006, Journal of agricultural and food chemistry.

[30]  E. Sikora,et al.  The sources of natural antioxidants , 2008 .

[31]  V. Marsilio,et al.  1 H and 13C NMR characterization of new oleuropein aglycones , 1995 .

[32]  A. Segura Carretero,et al.  Electrophoretic identification and quantitation of compounds in the polyphenolic fraction of extra‐virgin olive oil , 2005, Electrophoresis.

[33]  F. Shahidi,et al.  Phenolic antioxidants. , 1992, Critical reviews in food science and nutrition.

[34]  E. Frankel.  Volatile lipid oxidation products. , 1983, Progress in lipid research.

[35]  M. Brenes,et al.  Use of 1-acetoxypinoresinol to authenticate Picual olive oils , 2002 .

[36]  D. Caruso,et al.  Rapid evaluation of phenolic component profile and analysis of oleuropein aglycon in olive oil by atmospheric pressure chemical ionization-mass spectrometry (APCI-MS). , 2000, Journal of agricultural and food chemistry.

[37]  P. Prenzler,et al.  Novel secoiridoids with antioxidant activity from Australian olive mill waste. , 2007, Journal of agricultural and food chemistry.

[38]  A. S. Carretero,et al.  Electrophoretic identification and quantitation of compounds in the polyphenolic fraction of extra-virgin olive oil. , 2005 .

[39]  Elena Falqué,et al.  Effect of storage time and container type on the quality of extra-virgin olive oil , 2007 .

[40]  R. Lamuela-Raventós,et al.  Presence of virgin olive oil phenolic metabolites in human low density lipoprotein fraction: determination by high-performance liquid chromatography-electrospray ionization tandem mass spectrometry. , 2007, Analytica chimica acta.

[41]  R. Prior,et al.  Standardized methods for the determination of antioxidant capacity and phenolics in foods and dietary supplements. , 2005, Journal of agricultural and food chemistry.

[42]  S. Wiseman,et al.  Supplementation of plasma with olive oil phenols and extracts: influence on LDL oxidation. , 2002, Journal of agricultural and food chemistry.

[43]  K. Webb,et al.  Intercomparison study on accurate mass measurement of small molecules in mass spectrometry , 2003, Journal of the American Society for Mass Spectrometry.

[44]  L. Verotta,et al.  Secoiridoids from Olea europaea , 1986 .

[45]  M. Amiot,et al.  Importance and evolution of phenolic compounds in olive during growth and maturation , 1986 .

[46]  G. la Marca,et al.  Electrospray ionisation tandem mass spectrometric investigation of phenylpropanoids and secoiridoids from solid olive residue. , 2006, Rapid communications in mass spectrometry : RCM.

[47]  P. Lorenz,et al.  Natural and newly synthesized hydroxy-1-aryl-isochromans: A class of potential antioxidants and radical scavengers , 2005, Free radical research.

[48]  T. V. van Beek,et al.  Isolation and identification of radical scavengers in olive tree (Olea europaea) wood. , 2006, Journal of chromatography. A.

[49]  G. Bellomo,et al.  Free radical-scavenging properties of olive oil polyphenols. , 1998, Biochemical and biophysical research communications.

[50]  José M. García,et al.  Modification of volatile compound profile of virgin olive oil due to hot-water treatment of olive fruit. , 2003, Journal of agricultural and food chemistry.

[51]  L. Barthelmebs,et al.  Knockout of the p-Coumarate Decarboxylase Gene from Lactobacillus plantarum Reveals the Existence of Two Other Inducible Enzymatic Activities Involved in Phenolic Acid Metabolism , 2000, Applied and Environmental Microbiology.

[52]  H. Bartsch,et al.  Phenolic compounds and squalene in olive oils: the concentration and antioxidant potential of total phenols, simple phenols, secoiridoids, lignansand squalene. , 2000, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[53]  J. Bautista,et al.  Lipophilic hydroxytyrosyl esters. Antioxidant activity in lipid matrices and biological systems. , 2006, Journal of agricultural and food chemistry.

[54]  U. Holzgrabe,et al.  Analysis of the glucosinolate pattern of Arabidopsis thaliana seeds by capillary zone electrophoresis coupled to electrospray ionization‐mass spectrometry , 2005, Electrophoresis.

[55]  P Mata,et al.  International conference on the healthy effect of virgin olive oil , 2005, European journal of clinical investigation.

[56]  M. Uceda,et al.  Evaluation of virgin olive oil bitterness by total phenol content analysis , 2007 .

[57]  F. Angerosa,et al.  GC-MS evaluation of phenolic compounds in virgin olive oil , 1995 .

[58]  L. Le Marchand.  Cancer preventive effects of flavonoids--a review. , 2002, Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.

[59]  M. D. Valle,et al.  Componentes fenolicos de la aceituna, 3: Polifenoles del aceite [de oliva]. , 1976 .

[60]  T. G. Toschi,et al.  Qualitative and semiquantitative analysis of phenolic compounds in extra virgin olive oils as a function of the ripening degree of olive fruits by different analytical techniques. , 2004, Journal of agricultural and food chemistry.

[61]  R. Lamuela-Raventós,et al.  Characterization and quantification of phenolic compounds in olive oils by solid-phase extraction, HPLC-DAD, and HPLC-MS/MS. , 2005, Journal of agricultural and food chemistry.

[62]  N. Uccella,et al.  Biophenolic profile in olives by nuclear magnetic resonance , 2001 .

[63]  J. M. Olías,et al.  Evaluation of the bitter taste in virgin olive oil , 1992 .

[64]  G. la Marca,et al.  Solid olive residues: insight into their phenolic composition. , 2005, Journal of agricultural and food chemistry.

[65]  M. Gordon,et al.  Effects of copper on the antioxidant activity of olive polyphenols in bulk oil and oil-in-water emulsions. , 2006, Journal of agricultural and food chemistry.

[66]  F. Pastor,et al.  Biochemical studies on cloned Bacillus sp. BP-7 phenolic acid decarboxylase PadA , 2003, Applied Microbiology and Biotechnology.

[67]  Anne M. Drolet,et al.  Use of polyamide oxidative fluorescence test on lipid emulsions : contrast in relative effectiveness of antioxidants in bulk versus dispersed systems , 1989 .

[68]  M. Desamparados Salvador,et al.  Retention effects of oxidized polyphenols during analytical extraction of phenolic compounds of virgin olive oil. , 2007, Journal of separation science.

[69]  M. V. Russo,et al.  Determination of phenolic acids in olive oil by capillary electrophoresis. , 2004, Annali di chimica.

[70]  K. Hrnčiřík,et al.  Comparability and reliability of different techniques for the determination of phenolic compounds in virgin olive oil , 2004 .

[71]  De Nino A,et al.  Virtual freezing of the hemiacetal-aldehyde equilibrium of the aglycones of oleuropein and ligstroside present in olive oils from Carolea and Coratina cultivars by ionspray ionization tandem mass spectrometry , 2000, Journal of mass spectrometry : JMS.

[72]  N. Cortesi,et al.  I componenti minori polari degli oli vergini di oliva : ipotesi di struttura mediante LC-MS , 1995 .

[73]  F. Bornet,et al.  Olive oil phenolics are dose‐dependently absorbed in humans , 2000, FEBS letters.

[74]  T. Gomes,et al.  Phenolic compounds in virgin olive oils: influence of the degree of olive ripeness on organoleptic characteristics and shelf-life , 2001 .

[75]  L. Liberatore,et al.  HPLC and HRGC analyses of polyphenols and secoiridoid in olive oil , 2001 .

[76]  H. Mykkänen,et al.  Screening of selected flavonoids and phenolic acids in 19 berries , 1999 .

[77]  C. Kandaswami,et al.  The antitumor activities of flavonoids. , 2005, In vivo.

[78]  L. Skibsted,et al.  Antioxidant synergy and regeneration effect of quercetin, (-)-epicatechin, and (+)-catechin on alpha-tocopherol in homogeneous solutions of peroxidating methyl linoleate. , 2002, Journal of agricultural and food chemistry.

[79]  I. Stupans,et al.  The in vivo fate of hydroxytyrosol and tyrosol, antioxidant phenolic constituents of olive oil, after intravenous and oral dosing of labeled compounds to rats. , 2001, The Journal of nutrition.

[80]  F. Visioli,et al.  Olive Oil Phenols and Their Potential Effects on Human Health , 1998 .

[81]  R. Lamuela-Raventós,et al.  Rapid high-performance liquid chromatography-electrospray ionization tandem mass spectrometry method for qualitative and quantitative analysis of virgin olive oil phenolic metabolites in human low-density lipoproteins. , 2006, Journal of chromatography. A.

[82]  E. Fedeli,et al.  Minor polar components of virgin olive oils. A hypothetical structure by LC-MS [liquid chromatography - mass spectrometry]. , 1995 .

[83]  L. Tseng,et al.  Separation and identification of phenolic compounds in olive oil by coupling high-performance liquid chromatography with postcolumn solid-phase extraction to nuclear magnetic resonance spectroscopy (LC-SPE-NMR). , 2005, Journal of agricultural and food chemistry.

[84]  A. S. Csallany,et al.  High-performance liquid chromatography of selected phenolic compounds in olive oils , 1993 .

[85]  H. Bartsch,et al.  Isolation, structure elucidation and antioxidant potential of the major phenolic and flavonoid compounds in brined olive drupes. , 2003, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[86]  A. Segura‐Carretero,et al.  Evaluation of the influence of thermal oxidation on the phenolic composition and on the antioxidant activity of extra-virgin olive oils. , 2007, Journal of agricultural and food chemistry.

[87]  D. Arráez-Román,et al.  Capillary electrophoresis‐electrospray ionization‐mass spectrometry method to determine the phenolic fraction of extra‐virgin olive oil , 2006, Electrophoresis.

[88]  V. Fogliano,et al.  Oleocanthal in olive oil: between myth and reality. , 2006, Molecular nutrition & food research.

[89]  F. Sinesio,et al.  The dynamic sensory evaluation of bitterness and pungency in virgin olive oil , 2005 .

[90]  A. Bendini,et al.  Quality, composition and production process of virgin olive oils , 2007 .

[91]  Albi,et al.  Bitter Taste of Virgin Olive Oil: Correlation of Sensory Evaluation and Instrumental HPLC Analysis , 1989 .

[92]  Bo Zhou,et al.  Antioxidant effects of green tea polyphenols on free radical initiated peroxidation of rat liver microsomes. , 2002, Chemistry and physics of lipids.

[93]  L. Thompson,et al.  The effect of flaxseed supplementation on the initiation and promotional stages of mammary tumorigenesis. , 1992, Nutrition and cancer.

[94]  T. Hofmann,et al.  Characterization of an intense bitter-tasting 1H,4H-quinolizinium-7-olate by application of the taste dilution analysis, a novel bioassay for the screening and identification of taste-active compounds in foods. , 2001, Journal of agricultural and food chemistry.

[95]  Jeffrey B. Harborne,et al.  The Flavonoids Advances in Research Since 1986 , 1993 .

[96]  A. Cimato,et al.  Polyphenolic content in five tuscany cultivars of Olea europaea L. , 1999, Journal of agricultural and food chemistry.

[97]  P. Richardson.  The Flavonoids: Advances in Research , 1982 .

[98]  R. J. Robbins,et al.  Phenolic acids in foods: an overview of analytical methodology. , 2003, Journal of agricultural and food chemistry.

[99]  Francesco Addeo,et al.  1H and 13C NMR of virgin olive oil. An overview , 1997 .

[100]  E. G. Constante,et al.  Estudio de los componentes del aceite de oliva por cromatografia liquida de alta eficacia (HPLC). II. Cromatografia en fase inversa , 1980 .

[101]  C. Nergiz,et al.  Determination of phenolic acids in virgin olive oil , 1991 .

[102]  T. Gutfinger,et al.  Polyphenols in olive oils , 1981 .

[103]  A. Segura‐Carretero,et al.  Evaluation of the antioxidant capacity of individual phenolic compounds in virgin olive oil. , 2005, Journal of agricultural and food chemistry.

[104]  Dejian Huang,et al.  The chemistry behind antioxidant capacity assays. , 2005, Journal of agricultural and food chemistry.

[105]  A. Romani,et al.  Antioxidant effect of two virgin olive oils depends on the concentration and composition of minor polar compounds. , 2006, Journal of agricultural and food chemistry.

[106]  P. Prenzler,et al.  Liquid chromatography with electrospray ionisation mass spectrometric detection of phenolic compounds from Olea europaea. , 1999, Journal of chromatography. A.

[107]  A. Romani,et al.  HPLC analysis of flavonoids and secoiridoids in leaves of Ligustrum vulgare L. (Oleaceae). , 2000, Journal of agricultural and food chemistry.

[108]  A. Polidori,et al.  ANALYSIS BY HPLC-MS/MS OF BIOPHENOLIC COMPONENTS IN OLIVES AND OILS , 2001 .

[109]  F. Angerosa,et al.  Virgin olive oil odour notes: their relationships with volatile compounds from the lipoxygenase pathway and secoiridoid compounds , 2000 .

[110]  R. Elias,et al.  Rapid high-performance liquid chromatography analysis for the quantitative determination of oleuropein in Olea europaea leaves. , 2001, Journal of agricultural and food chemistry.

[111]  M. Tsimidou,et al.  Determination of phenolic compounds in virgin olive oil by reversed-phase HPLC with emphasis on UV detection , 1992 .

[112]  H. Bartsch,et al.  Identification of lignans as major components in the phenolic fraction of olive oil. , 2000, Clinical chemistry.

[113]  R. Frazier,et al.  The development and application of capillary electrophoresis methods for food analysis , 1999, Electrophoresis.

[114]  Sami Sayadi,et al.  The use of polyphenolic extract, purified hydroxytyrosol and 3,4-dihydroxyphenyl acetic acid from olive mill wastewater for the stabilization of refined oils: a potential alternative to synthetic antioxidants , 2005 .

[115]  A. Bianco,et al.  Analysis by liquid chromatography‐tandem mass spectrometry of biophenolic compounds in virgin olive oil, Part II , 2003 .

[116]  J. Fernández-Bolaños,et al.  Production in large quantities of highly purified hydroxytyrosol from liquid-solid waste of two-phase olive oil processing or "Alperujo". , 2002, Journal of agricultural and food chemistry.

[117]  D. Bedgar,et al.  On the stereoselective synthesis of (+)-pinoresinol in Forsythia suspensa from its achiral precursor, coniferyl alcohol. , 1992, Phytochemistry.

[118]  M. Amiot,et al.  Accumulation of oleuropein derivatives during olive maturation , 1989 .

[119]  G. Vlahov.  Flavonoids in three olive (Olea europaea) fruit varieties during maturation , 1992 .

[120]  E. Ibáñez,et al.  New Analytical Techniques in Food Science , 2001, Critical reviews in food science and nutrition.

[121]  G. Cartoni,et al.  HPLC ANALYSIS OF THE BENZOIC AND CINNAMIC ACIDS IN EDIBLE VEGETABLE OILS , 2000 .

[122]  S. Sayadi,et al.  Identification and antioxidant potential of flavonoids and low molecular weight phenols in olive cultivar chemlali growing in Tunisia. , 2005, Journal of agricultural and food chemistry.

[123]  M. Guiso,et al.  The occurrence in olive oil of a new class of phenolic compounds: hydroxy-isochromans , 2002 .

[124]  C. S. Yang,et al.  Inhibition of carcinogenesis by dietary polyphenolic compounds. , 2001, Annual review of nutrition.

[125]  M. Coimbra,et al.  Identification of oleuropein oligomers in olive pulp and pomace , 2006 .

[126]  M. Murkovic,et al.  Analysis of minor components in olive oil. , 2004, Journal of biochemical and biophysical methods.

[127]  L. Marchand.  Cancer preventive effects of flavonoids—a review , 2002 .

[128]  P. Nestel.  Isoflavones: their effects on cardiovascular risk and functions , 2003, Current opinion in lipidology.

[129]  Dimitrios Boskou,et al.  Phenolic compounds and stability of virgin olive oil—Part I , 1992 .

[130]  W. Steurer,et al.  Olive oil is more potent than fish oil to reduce septic pulmonary dysfunctions in rats , 2007, Langenbeck's Archives of Surgery.

[131]  Maurizio Servili,et al.  Simple and hydrolyzable phenolic compounds in virgin olive oil. 1. Their extraction, separation, and quantitative and semiquantitative evaluation by HPLC , 1992 .

[132]  R. Nucci,et al.  Antioxidant properties of low molecular weight phenols present in the mediterranean diet. , 2003, Journal of agricultural and food chemistry.

[133]  M. C. Pérez-Camino,et al.  Evaluation of virgin olive oil bitterness by quantification of secoiridoid derivatives , 2004 .

[134]  B. Stavric.  Role of chemopreventers in human diet. , 1994, Clinical biochemistry.

[135]  T. G. Toschi,et al.  Effect of olive ripening degree on the oxidative stability and organoleptic properties of cv. Nostrana di Brisighella extra virgin olive oil. , 2004, Journal of agricultural and food chemistry.

[136]  A. Segura‐Carretero,et al.  CE‐ and HPLC‐TOF‐MS for the characterization of phenolic compounds in olive oil , 2007, Electrophoresis.

[137]  M. Gordon,et al.  Interactions of ferric ions with olive oil phenolic compounds. , 2005, Journal of agricultural and food chemistry.

[138]  A. Gómez-Caravaca,et al.  Effect of Filtration Systems on the Phenolic Content in Virgin Olive Oil by HPLC-DAD-MSD , 2007 .

[139]  Hong-yu Zhang,et al.  Radical scavenging potential of phenolic compounds encountered in O. europaea products as indicated by calculation of bond dissociation enthalpy and ionization potential values. , 2005, Journal of agricultural and food chemistry.

[140]  P. Matarrese,et al.  Extra virgin olive oil biophenols inhibit cell-mediated oxidation of LDL by increasing the mRNA transcription of glutathione-related enzymes. , 2004, The Journal of nutrition.

[141]  R. de Caterina,et al.  Olive Oil and Red Wine Antioxidant Polyphenols Inhibit Endothelial Activation: Antiatherogenic Properties of Mediterranean Diet Phytochemicals , 2003, Arteriosclerosis, thrombosis, and vascular biology.

[142]  A. Segura Carretero,et al.  Co-electroosmotic capillary electrophoresis determination of phenolic acids in commercial olive oil. , 2005, Journal of separation science.

[143]  L. Diosady,et al.  Rapid method for total phenolic acid determination in rapeseed/canola meals , 1997 .

[144]  A. Gómez-Caravaca,et al.  Rapid quantification of the phenolic fraction of Spanish virgin olive oils by capillary electrophoresis with UV detection. , 2006, Journal of agricultural and food chemistry.

[145]  M. Tsimidou,et al.  Methodology for identification of phenolic acids in complex phenolic mixtures by high-resolution two-dimensional nuclear magnetic resonance. Application to methanolic extracts of two oregano species , 1998 .

[146]  J. Andrade,et al.  Anticancer activity of phenolic acids of natural or synthetic origin: a structure-activity study. , 2003, Journal of medicinal chemistry.

[147]  A. Gómez-Caravaca,et al.  A simple and rapid electrophoretic method to characterize simple phenols, lignans, complex phenols, phenolic acids, and flavonoids in extra-virgin olive oil. , 2006, Journal of separation science.

[148]  K. James,et al.  Comparison of four mass analyzers for determining carbosulfan and its metabolites in citrus by liquid chromatography/mass spectrometry. , 2006, Rapid communications in mass spectrometry : RCM.

[149]  Hermann Wätzig,et al.  Quantitation in capillary electrophoresis‐mass spectrometry , 2005, Electrophoresis.

[150]  Marco Mascini,et al.  Biosensor measurements of polar phenolics for the assessment of the bitterness and pungency of virgin olive oil. , 2006, Journal of agricultural and food chemistry.

[151]  J. J. Moreno.  Effect of olive oil minor components on oxidative stress and arachidonic acid mobilization and metabolism by macrophages RAW 264.7. , 2003, Free radical biology & medicine.

[152]  M. Tsimidou,et al.  On the determination of minor phenolic acids of virgin olive oil by RP-HPLC , 1996 .

[153]  J. Maga,et al.  Simple phenol and phenolic compounds in food flavor. , 1978, CRC critical reviews in food science and nutrition.

[154]  G. Vlahov,et al.  Application of NMR to the study of olive oils , 1999 .

[155]  J. Cillard,et al.  Peroxyl and hydroxyl radical scavenging activity of some natural phenolic antioxidants , 1991 .

[156]  M. Tsimidou.  Polyphenols and quality of virgin olive oil in retrospect , 1998 .

[157]  M. Motilva,et al.  Antioxidant activity of olive pulp and olive oil phenolic compounds of the arbequina cultivar. , 2005, Journal of agricultural and food chemistry.

[158]  Å. Hansen,et al.  Content of phenolic acids and ferulic acid dehydrodimers in 17 rye (Secale cereale L.) varieties. , 2000, Journal of agricultural and food chemistry.

[159]  A. Kiritsakis,et al.  Flavor components of olive oil—A review , 1998 .

[160]  E. Frankel.  Antioxidants in lipid foods and their impact on food quality , 1996 .

[161]  H. Bartsch,et al.  The antioxidant/anticancer potential of phenolic compounds isolated from olive oil. , 2000, European journal of cancer.

[162]  H. Wätzig,et al.  Quantification in capillary electrophoresis‐mass spectrometry: Long‐ and short‐term variance components and their compensation using internal standards , 2005, Electrophoresis.

[163]  R. Lamuela-Raventós,et al.  Protective effect of olive oil and its phenolic compounds against low density lipoprotein oxidation , 2000, Lipids.

[164]  G. Togna,et al.  Olive oil isochromans inhibit human platelet reactivity. , 2003, The Journal of nutrition.

[165]  C. Keen,et al.  Cocoa and chocolate flavonoids: implications for cardiovascular health. , 2003, Journal of the American Dietetic Association.

[166]  Jacques Vervoort,et al.  LC-UV-solid-phase extraction-NMR-MS combined with a cryogenic flow probe and its application to the identification of compounds present in Greek oregano. , 2003, Analytical chemistry.

[167]  C. F. Timberlake.  The Flavonoids—Advances in Research since 1980: : edited by J. B. Harborne. Chapman & Hall, London and New York, xiii+621 pp. £95. , 1989 .

[168]  W. Griffiths.  Food phenolics: Sources, chemistry, effects, applications , 1996 .

[169]  Z. Madar,et al.  Olive oil as a functional food: epidemiology and nutritional approaches. , 2002, Nutrition reviews.

[170]  C. Cruces‐Blanco,et al.  Sensitive determination of phenolic acids in extra-virgin olive oil by capillary zone electrophoresis. , 2004, Journal of agricultural and food chemistry.

[171]  D. Pilbeam.  The Flavonoids: Advances in Research : Edited by J.B. Harborne and T.J. Mabry Chapman and Hall; London, New York, 1982 744 pages. £ 49.50 , 1983 .

[172]  M. Gil,et al.  Solid-phase extraction gas chromatography-ion trap-mass spectrometry qualitative method for evaluation of phenolic compounds in virgin olive oil and structural confirmation of oleuropein and ligstroside aglycons and their oxidation products. , 2005, Journal of chromatography. A.

[173]  Paul Andrewes,et al.  Sensory properties of virgin olive oil polyphenols: identification of deacetoxy-ligstroside aglycon as a key contributor to pungency. , 2003, Journal of agricultural and food chemistry.

[174]  Rafael de la Torre,et al.  Minor Components of Olive Oil: Evidence to Date of Health Benefits in Humans , 2006 .

[175]  K. Tuck,et al.  Major phenolic compounds in olive oil: metabolism and health effects. , 2002, The Journal of nutritional biochemistry.

[176]  A. Romani,et al.  Polyphenolic content in olive oil waste waters and related olive samples. , 2001, Journal of agricultural and food chemistry.

[177]  F. Shahidi,et al.  Phenolics in food and nutraceuticals , 1995 .

[178]  S. Mannino,et al.  High performance liquid chromatography of phenolic compounds in virgin olive oils using amperometric detection , 1993 .

[179]  G. Bandino,et al.  Phenolic compounds in virgin olive oils I. Low-wavelength quantitative determination of complex phenols by high-performance liquid chromatography under isocratic elution , 1997 .

[180]  E. Coni,et al.  Protective effect of oleuropein, an olive oil biophenol, on low density lipoprotein oxidizability in rabbits , 2000, Lipids.

[181]  A. F. Vinha,et al.  Phenolic profiles of Portuguese olive fruits (Olea europaea L.): Influences of cultivar and geographical origin , 2005 .

[182]  P. Cabras,et al.  Phenolic compounds in virgin olive oil. 2. Reappraisal of the extraction, HPLC separation, and quantification procedures. , 2000, Journal of agricultural and food chemistry.

[183]  A. Saija,et al.  On the In‐vitro Antimicrobial Activity of Oleuropein and Hydroxytyrosol , 1999, The Journal of pharmacy and pharmacology.

[184]  Maurizio Servili,et al.  High-performance liquid chromatography evaluation of phenols in olive fruit, virgin olive oil, vegetation waters, and pomace and 1D- and 2D-nuclear magnetic resonance characterization , 1999 .

[185]  I. Stupans,et al.  Structural characterization of the metabolites of hydroxytyrosol, the principal phenolic component in olive oil, in rats. , 2002, Journal of agricultural and food chemistry.

[186]  N. Uccella,et al.  Biophenolic components of olives , 2000 .

[187]  Hugh McGlynn,et al.  Components of olive oil and chemoprevention of colorectal cancer. , 2005, Nutrition reviews.

[188]  A. S. Carretero,et al.  Co-electroosmotic capillary electrophoresis determination of phenolic acids in commercial olive oil. , 2005 .

[189]  A. Bendini,et al.  Protective effects of extra virgin olive oil phenolics on oxidative stability in the presence or absence of copper ions. , 2006, Journal of agricultural and food chemistry.

[190]  H. Kuwajima,et al.  A secoiridoid glucoside from Olea europaea , 1988 .

[191]  G. Fregapane,et al.  Effect of filtration on virgin olive oil stability during storage , 2006 .

[192]  A. Romani,et al.  Evaluation of lignans and free and linked hydroxy-tyrosol and tyrosol in extra virgin olive oil after hydrolysis processes , 2006 .

[193]  M. Tsimidou,et al.  Loss of stability of “veiled” (cloudy) virgin olive oils in storage , 2005 .

[194]  R. Rouseff,et al.  Distribution of bound and free phenolic acids in oranges (Citrus sinensis) and Grapefruits (Citrus paradisi) , 1991 .

[195]  A. García,et al.  Phenolic compounds in Spanish olive oils. , 1999, Journal of agricultural and food chemistry.

[196]  Jozef P. H. Linssen,et al.  Phenolic compounds in virgin olive oils : Fractionation by solid phase extraction and antioxidant activity assessment , 1997 .

[197]  R. Mateos,et al.  Reduction of oil bitterness by heating of olive (Olea europaea) fruits. , 2001, Journal of agricultural and food chemistry.

[198]  M. Servili,et al.  Simple and hydrolyzable phenolic compounds in virgin olive oil. 2. Initial characterization of the hydrolyzable fraction. , 1992 .

[199]  F. Gutiérrez-Rosales,et al.  Main polyphenols in the bitter taste of virgin olive oil. Structural confirmation by on-line high-performance liquid chromatography electrospray ionization mass spectrometry. , 2003, Journal of agricultural and food chemistry.

[200]  M. Boyce.  Determination of additives in food by capillary electrophoresis , 2001, Electrophoresis.

[201]  M. Gordon,et al.  Antioxidant activity of hydroxytyrosol acetate compared with that of other olive oil polyphenols. , 2001, Journal of agricultural and food chemistry.

[202]  A. Ranalli,et al.  1H NMR Study of Phenolics in the Vegetation Water of Three Cultivars of Olea europaea: Similarities and Differences† , 1996 .

[203]  E. Lissi,et al.  Review of methods to determine chain-breaking antioxidant activity in food , 2005 .

[204]  E. Fedeli,et al.  Analysis of flavonoids from Olea Europaea by HPLC-UV and HPLC-electrospray-MS , 1997 .

[205]  R. Capasso.  A review on the electron ionization and fast atom bombardment mass spectrometry of polyphenols naturally occurring in olive wastes and some of their synthetic derivatives , 1999 .

[206]  F. Visioli,et al.  Postprandial anti-inflammatory and antioxidant effects of extra virgin olive oil. , 2007, Atherosclerosis.

[207]  J. Havel,et al.  Separation of polyphenols in Canary Islands wine by capillary zone electrophoresis without preconcentration. , 2000, Journal of chromatography. A.

[208]  T. Gallina Toschi,et al.  Fast separation and determination of tyrosol, hydroxytyrosol and other phenolic compounds in extra-virgin olive oil by capillary zone electrophoresis with ultraviolet-diode array detection. , 2003, Journal of chromatography. A.

[209]  J J Ríos,et al.  Determination of phenols, flavones, and lignans in virgin olive oils by solid-phase extraction and high-performance liquid chromatography with diode array ultraviolet detection. , 2001, Journal of agricultural and food chemistry.

[210]  H. Issaq.  Capillary electrophoresis of natural products‐II , 1999, Electrophoresis.