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1.
There is increasing interest in olive polyphenols because of their biological properties as well as their contribution to the color, taste, and shelf life of olive products. However, some of these compounds remain unidentified. It has been shown that hydroxytyrosol 4-beta-D-glucoside (4-beta-D-glucosyl-3-hydroxyphenylethanol) coeluted with hydroxytyrosol [(3,4-dihydroxyphenyl)ethanol] under reversed phase conditions in the phenolic chromatograms of olive pulp, vegetation water, and pomace of olive oil processing. A method to separate this compound from hydroxytyrosol by HPLC has been developed. The concentration of this glucoside increased in olive pulp with maturation and could be the main phenolic compound in mature olives. In contrast, the presence of this compound was not detected in olive oil by using HPLC-MS. The compound must be considered both in table olives and olive oil processing because of its glucose and hydroxytyrosol contribution to these products.  相似文献   

2.
Epidemiological studies have linked the Mediterranean diet with a low incidence of cardiovascular diseases. Olive oil, the major fat component of this diet, is characterized by antioxidant properties related to their content in catecholic components, particularly oleuropein aglycon. Therefore quantification of these components in edible oils may be important in determining the quality, and consequently its commercial value. The present method allows us to obtain the profile of the phenolic components of the oil from the methanolic extracts of the crude olive oil. In particular tyrosol, hydroxytyrosol, elenolic acid, deacetoxyligstroside and deacetoxyoleuropein aglycons, ligstroside and oleuropein aglycons, and 10-hydroxy-oleuropein are clearly identified by atmospheric pressure chemical ionization-mass spectrometry (APCI-MS). Moreover, oleuropein and its isomers present in the oil are quantified by APCI-MS/MS analysis of the extracts without preliminary separation from other phenolic compounds.  相似文献   

3.
The individual evolution of phenolic compounds has been studied during the natural fermentation of black olives for the first time. Cyanidin 3-rutinoside and cyanidin 3-glucoside were the main anthocyanins identified in fresh olives, and they were not detected after 1 month of storage either in brine or in olive. The fruit colors were different when aerobic or anaerobic conditions were used and as a consequence of the different anthocyanin polymerizations that took place. At time zero, the polyphenols observed in the olive juice were hydroxytyrosol-4-beta-glucoside, oleuropein, hydroxytyrosol, tyrosol, salidroside, and verbascoside and, after 12 months, the main phenol was hydroxytyrosol. The polyphenol content in the oil phase of olives was also analyzed. The dialdehydic form of elenolic acid linked to hydroxytyrosol and tyrosol, oleuropein aglycon, and ligstroside aglycon were the main compounds found at the beginning of fermentation but were not detected after 3 months. In contrast, hydroxytyrosol, hydroxytyrosol acetate, tyrosol, and tyrosol acetate were the main polyphenols detected in the oil phase of the final product. The acid hydrolysis of the initial glucosides (in olive juice) and the aglycons (in oil phase) was, therefore, the main reaction that took place during fermentation.  相似文献   

4.
Fifty lactobacilli isolated from black table olive brines were evaluated for their salt tolerance, resistance to oleuropein and verbascoside, and ability to grow in modified filter-sterilized brines. A strain of Lactobacillus pentosus was selected and used as a starter to ferment, in pilot plant, black olives (Itrana and Leccino cv.) in brines modified for pH, carbohydrate, and growth factor concentrations, at 28 degrees C. The temperature-controlled fermentation of Leccino cv. olives resulted in obtaining ready-to-eat, high-quality table olives in a reduced-time process. HPLC analysis of phenolic compounds from fermented olives showed a decrease of oleuropein, a glucoside secoiridoid responsible for the bitter taste of olive drupes, and an increase of the hydroxytyrosol concentration. The selected strain of L. pentosus (1MO) allowed the reduction of the debittering phase period to 8 days.  相似文献   

5.
Polyphenols were determined by HPLC in the juice and oil of packed table olives. The phenolic compositions of the two phases were very different, hydroxytyrosol and tyrosol being the main polyphenols in olive juice and tyrosol acetate, hydroxtyrosol acetate, hydroxytyrosol, tyrosol, and lignans (1-acetoxypinoresinol and pinoresinol) in oil. The type of processing had a marked influence on the concentration of polyphenols in olive juice and little on the content in oil. The analyses carried out on 48 samples showed that turning color olives in brine had the highest concentration in polyphenols ( approximately 1200 mg/kg), whereas oxidized olives had the lowest ( approximately 200 mg/kg). Among olive cultivars, Manzanilla had a higher concentration than Hojiblanca and Gordal. The type of olive presentation also influenced the concentration of polyphenols in olives, decreasing in the order plain > pitted > stuffed. The results obtained in this work indicate that table olives can be considered a good source of phenolic antioxidants, although their concentration depends on olive cultivar and processing method.  相似文献   

6.
Olive oil is the essential component of the Mediterranean diet, a nutritional regimen gaining ever-increasing renown for its beneficial effects on inflammation, cardiovascular disease, and cancer. A unique characteristic of olive oil is its enrichment in oleuropein, a member of the secoiridoid family, which hydrolyzes to the catechol hydroxytyrosol and functions as a hydrophilic phenolic antioxidant that is oxidized to its catechol quinone during redox cycling. Little effort has been spent on exploring the biological properties of the catechol hydroxytyrosol quinone, a strong arylating electrophile that forms Michael adducts with thiol nucleophiles in glutathione and proteins. This study compares the chemical and biological characteristics of hydroxytyrosol with those of the tocopherol family in which Michael adducts of arylating desmethyltocopherol quinones have been identified and correlated with biologic properties including cytotoxicity and induction of endoplasmic reticulum stress. It is noted that hydroxytyrosol and desmethyltocopherols share many similarities, suggesting that Michael adduct formation by an arylating quinone electrophile may contribute to the biological properties of both families, including the unique nutritional benefit of olive oil.  相似文献   

7.
Capillary electrophoresis (CE) can be effectively used as a fast screening tool to obtain qualitative and semiquantitative information about simple and complex phenolic compounds of extra virgin olive oil. Three simple phenols (tyrosol, hydroxytyrosol, and vanillic acid), a secoiridoid derivative (deacetoxy oleuropein aglycon), and two lignans (pinoresinol and acetoxypinoresinol) were detected as the main compounds in extra virgin olive oils by high-performance liquid chromatography (HPLC) and capillary zone electrophoresis (CZE). Spectrophotometric indices, radical scavenging activity, and oxidative stability of extra virgin olive oil samples obtained from olives hand-picked at different ripening degrees were statistically correlated with the CZE and HPLC quantification. The concentration of phenols in extra virgin olive oil decreased with ripeness of olive fruits. The high correlations found between CZE and the other analytical results indicate that CE can be applied as a rapid and reliable tool to routinely determine phenolic compounds in extra virgin olive oils.  相似文献   

8.
New bioactive epimeric derivatives of oleuropein have been detected in olive fruits and structurally characterized by (1)H and (13)C NMR. These hydrolytic metabolites, obtained by enzymatic catalysis, can be molecular microcomponents, present in Mediterranean food, table olives, and olive oil, responsible for complex sensorial attributes and for pathogen natural defense.  相似文献   

9.
The aim of this study was to characterize antioxidant activities of phenolic compounds that appear in olive pulp and olive oils using both radical scavenging and antioxidant activity tests. Antiradical and antioxidant activities of olive pulp and olive oil phenolic compounds were due mainly to the presence of a 3,4-dihydroxy moiety linked to an aromatic ring, and the effect depended on the polarity of the phenolic compound. Glucosides and more complex phenolics exhibited higher antioxidant activities toward oxidation of liposomes, whereas in bulk lipids aglycons were more potent antioxidants with the exception of oleuropein. Lignans acted as antioxidants only in liposomes, which could partly be due to their chelating activity, because liposome oxidation was initiated by cupric acetate. The antioxidant activity of virgin olive oil is principally due to the dialdehydic form of elenolic acid linked to hydroxytyrosol (3,4-DHPEA-EDA), a secoiridoid derivative (peak RT 36, structure unidentified), and luteolin.  相似文献   

10.
The Mediterranean diet reduces the risk of coronary artery disease as a consequence of its high content of antioxidants, namely, hydroxytyrosol (HT) and oleuropein aglycone (OleA), typical of virgin olive oil. Because intercellular and vascular cell adhesion molecules (ICAM-1 and VCAM-1) and E-selectin are crucial for endothelial activation, the role of the phenolic extract from extra virgin olive oil (OPE), OleA, HT, and homovanillyl alcohol (HVA) on cell surface and mRNA expression in human umbilical vascular endothelial cells (HUVEC) was evaluated. OPE strongly reduced cell surface expression of ICAM-1 and VCAM-1 at concentrations physiologically relevant (IC50 < 1 microM), linked to a reduction in mRNA levels. OleA and HT were the main components responsible for these effects. HVA inhibited cell surface expression of all the adhesion molecules, whereas the effect on mRNA expression was weaker. These results supply new insights on the protective role of olive oil against vascular risk through the down-regulation of adhesion molecules involved in early atherogenesis.  相似文献   

11.
Typical components of the Mediterranean diet, such as olive oil and red wine, contain high concentrations of complex phenols, which have been suggested to have an important antioxidant role. The aim of the present work was to determine the inhibitory potency of compounds such as oleuropein, hydroxytyrosol, and other structurally related compounds, such as gallic acid, toward reactive oxygen species generation and free radical scavenging ability. The potency of these compounds was also examined with respect to protecting in vitro low-density lipoprotein oxidation. These studies indicate that complex phenols, such as hydroxytyrosol, and gallic acid both inhibit free radical generation and act as free radical scavengers. The use of three different approaches to determine antioxidant potency demonstrates that activity in one test does not necessarily correlate with activity in another. It was also demonstrated that the presence of two phenolic groups is not always associated with antioxidant activity.  相似文献   

12.
The inhibitors involved in the lactic acid fermentation of table olives were investigated in aseptic olive brines of the Manzanilla and Gordal varieties. Phenolic and oleosidic compounds in these brines were identified by high-performance liquid chromatography with ultraviolet and electrospray ionization mass spectrometry detection, and several substances were also characterized by nuclear magnetic resonance. Among these compounds, the dialdehydic form of decarboxymethyl elenolic acid linked to hydroxytyrosol showed the strongest antilactic acid bacteria activity, and its presence in brines could explain the growth inhibition of these microorganisms during olive fermentation. However, it was found that the dialdehydic form of decarboxymethyl elenolic acid, identified for the first time in table olives, and an isomer of oleoside 11-methyl ester were also effective against Lactobacillus pentosus and can, therefore, contribute to the antimicrobial activity of olive brines. It must also be stressed that the three new inhibitors discovered in table olive brines exerted a more potent antibacterial activity than the well-studied oleuropein and hydroxytyrosol.  相似文献   

13.
The phenolic compounds composition, antioxidant potential, and antimicrobial activity of different table olives from Portugal, namely, natural black olives "Galega", black ripe olive "Negrinha de Freixo", Protected Designation of Origin (PDO) "Azeitona de Conserva Negrinha de Freixo" olives, and "Azeitona de Conserva de Elvas e Campo Maior" Designation of Origin (DO) olives, were investigated. The analysis of phenolic compounds was performed by reversed-phase HPLC/DAD, and seven compounds were identified and quantified: hydroxytyrosol, tyrosol, 5-O-caffeoilquinic acid, verbascoside, luteolin 7-O-glucoside, rutin, and luteolin. The antioxidant activity was assessed by the reducing power assay, the scavenging effect on DPPH (2,2-diphenyl-1-picrylhydrazyl) radicals, and the beta-carotene linoleate model system. The antioxidant activity was correlated with the amount of phenolics found in each sample. The antimicrobial activity was screened using Gram-positive (Bacillus cereus, Bacillus subtilis, Staphylococcus aureus) and Gram-negative bacteria (Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumoniae) and fungi (Candida albicans, Cryptococcus neoformans). PDO and DO table olives revealed a wide range of antimicrobial activity. C. albicans was resistant to all the analyzed extracts.  相似文献   

14.
The ferric complexing capacity of four phenolic compounds, occurring in olives and virgin olive oil, namely, oleuropein, hydroxytyrosol, 3,4-dihydroxyphenylethanol-elenolic acid (3,4-DHPEA-EA), and 3,4-dihydroxyphenylethanol-elenolic acid dialdehyde (3,4-DHPEA-EDA), and their stability in the presence of ferric ions were studied. At pH 3.5, all compounds formed a reversible 1:1 complex with ferric ions, but hydroxytyrosol could also form complexes containing >1 ferric ion per phenol molecule. At pH 5.5, the complexes between ferric ions and 3,4-DHPEA-EA or 3,4-DHPEA-EDA were relatively stable, indicating that the antioxidant activity of 3,4-DHPEA-EA or 3,4-DHPEA-EDA at pH 5.5 is partly due to their metal-chelating activity. At pH 7.4, a complex containing >1 ferric ion per phenol molecule was formed with hydroxytyrosol. Oleuropein, 3,4-DHPEA-EA, and 3,4-DHPEA-EDA also formed insoluble complexes at this pH. There was no evidence for chelation of Fe(II) by hydroxytyrosol or its derivatives. At all pH values tested, hydroxytyrosol was the most stable compound in the absence of Fe(III) but the most sensitive to the presence of Fe(III).  相似文献   

15.
Hydroxytyrosol acetate was synthesized, and the antioxidant activity of this olive oil component was assessed in comparison with that of other olive oil components, namely hydroxytyrosol, oleuropein, 3,4-DHPEA-EA, and alpha-tocopherol in bulk oil and oil-in-water emulsions. The activity of the compounds was also assessed by scavenging of 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals. Hydroxytyrosol acetate had a weaker DPPH radical scavenging activity than hydroxytyrosol, oleuropein, or 3,4-DHPEA-EA but it had a radical scavenging activity similar to that of alpha-tocopherol. In oil, the antioxidant activity of hydroxytyrosol acetate was much higher than that of alpha-tocopherol or oleuropein, but in an emulsion 3,4-DHPEA-EA and alpha-tocopherol were more effective as antioxidants than hydroxytyrosol acetate. The antioxidant activity of hydroxytyrosol acetate was rather similar to that of hydroxytyrosol in oil and emulsions despite the difference in DPPH radical scavenging activity.  相似文献   

16.
Technomimetic NMR experiments were performed in accordance with the lye treatment adopted during table olive industrial procedures for the debittering process causing oleuropein degradation. The site selective hydrolysis of the two ester groups, characterizing the biophenolic secoiridoid molecule, was shown to be dependent on the different reactivities of these functionalities. The process is controlled by the experimental conditions exerted on the olive pulp and determined by the buffering capacity of the olive mesocarp and by the epicarp molecular components influencing the reactant penetration into the fruit pulp. The overall hydrolytic process of oleuropein, the bitter principle of olives, using the technomimetic experimental mode, gave rise to its catabolic derivatives, hydroxytyrosol, 11-methyloleoside, and the monoterpene glucoside, technomimetically produced, isolated, and structurally characterized by (1)H, (13)C, and COSY spectroscopy as the oleoside.  相似文献   

17.
Maturity is one of the most important factors associated with the quality evaluation of fruit and vegetables. This work aims to investigate the effect of the maturation process of the olive fruit on the phenolic fraction and fatty acid of irrigated Chétoui cultivar. The phenolic composition was studied by using reverse-phase high-performance liquid chromatography followed by LC-MS and GC-MS analyses and fatty acids by GC. Oleuropein was the major phenolic compound at all stages of ripeness. Unexpectedly, both phenolic compounds hydroxytyrosol and oleuropein exhibited the same trends during maturation. Indeed, the oleuropein levels decreased during the ripening process and were not inversely correlated with the concentrations of hydroxytyrosol. The antioxidant capacity of olive extracts was evaluated by measuring the radical scavenging effect on 1,1-diphenyl-2-picrylhydrazyl and the beta-carotene linoleate model system. The IC 50 and AAC values of the olive extracts decreased from 3.68 to 1.61 microg/mL and from 645 to 431, respectively. There was a correlation between the antioxidant activity and the oleuropein concentration. The fatty acid composition was quantified in olive fruit during maturation and showed that fatty acids were characterized by the highest level of oleic acid, which reached 65.2%.  相似文献   

18.
Phenolic compounds in extra virgin olive oil (EVOO) have been associated with beneficial effects for health. Indeed, these compounds exert strong antiproliferative effects on many pathological processes, which has stimulated chemical characterization of the large quantities of wastes generated during olive oil production. In this investigation, the potential of byproducts generated during storage of EVOO as a natural source of antioxidant compounds has been evaluated using solid-liquid and liquid-liquid extraction processes followed by rapid resolution liquid chromatography (RRLC) coupled to electrospray time-of-flight and ion trap mass spectrometry (TOF/IT-MS). These wastes contain polyphenols belonging to different classes such as phenolic acids and alcohols, secoiridoids, lignans, and flavones. The relationship between phenolic and derived compounds has been tentatively established on the basis of proposed degradation pathways. Finally, qualitative and quantitative characterizations of solid and aqueous wastes suggest that these byproducts can be considered an important natural source of phenolic compounds, mainly hydroxytyrosol, tyrosol, decarboxymethyl oleuropein aglycone, and luteolin, which, after suitable purification, could be used as food antioxidants or as ingredients in nutraceutical products due to their interesting technological and pharmaceutical properties.  相似文献   

19.
Phenols present in olive oil may contribute to the health effects of the Mediterranean lifestyle. Olive oil antioxidants increase the resistance of low-density lipoproteins (LDL) against oxidation in vitro, but human intervention studies have failed to demonstrate similar consistent effects. To better mimic the in vivo situation, plasma was incubated with either individual olive oil phenols or olive oil extracts with different phenolic compositions, and LDL was subsequently isolated and challenged for its resistance to oxidation. The results show that the ortho-dihydroxy phenols (hydroxytyrosol and oleuropein-aglycone) are more efficient than their mono-hydroxy counterparts (tyrosol and ligstroside-aglycone) in increasing the resistance of LDL to oxidation. However, the concentration of antioxidants required to inhibit LDL oxidation when added to whole plasma was substantially higher as compared to previous data where antioxidants are directly added to isolated LDL. In conclusion, this study supports the hypothesis that extra virgin olive oil phenols protect LDL in plasma against oxidation. The explanation that in vitro studies show protective effects in contrast to the lack of effect in the majority of human studies may be that the dose of the phenols and thus their plasma concentration in humans was too low to influence ex vivo LDL oxidizability. Further studies are required to gain a better understanding of the potential health benefits that extra virgin olive oil may provide.  相似文献   

20.
This study reports the HPLC profiles of phenolic compounds of virgin olive oils obtained from young olive trees (Olea europaea L. cv. Arbequina) and how the application of a linear irrigation strategy affected these. Hydroxytyrosol, tyrosol, vanillic acid, vanillin, 4-(acetoxyethyl)-1,2-dihydroxybenzene, p-coumaric acid, the dialdehydic form of elenolic acid linked to hydroxytyrosol and to tyrosol, lignans, and the oleuropein aglycon were found in all the oils. Hydroxytyrosol, tyrosol, vanillic acid, and p-coumaric acid contents in the oils were unaffected by linear irrigation. The concentration of lignans was lower in the oils from the least irrigated treatment and the concentration of vanillin increased as the amount of irrigation water applied to olive trees increased. However, 4-(acetoxyethyl)-1,2-dihydroxybenzene, the dialdehydic form of elenolic acid linked to hydroxytyrosol and to tyrosol, and the oleuropein aglycon, all of them hydroxyphenyl derivatives, decreased as the level of irrigation water increased. The latter three compounds represented the most considerable part of the phenolic fraction of the oils and they were shown to be correlated to the oxidative stability, the bitter index (K(225)), and the bitter, pungent, and sweet sensory attributes. Linear irrigation strategy changed the profile of the oil phenolic compounds and, therefore, changed both the organoleptic properties and the antioxidant capacity of the product.  相似文献   

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