Effect of standard phenolic compounds and olive oil phenolic extracts on acrylamide formation in an emulsion system

In this work the effect of standard phenolic compounds such as trolox, phenolic acids (ferulic, gallic, protocatechuic and caffeic acid) and secoiridoids, extracted from virgin olive oil (VOO), on acrylamide formation in an emulsion system was investigated. The emulsion system was heated in an oil bath at different temperatures and for different periods of time. At 105 and 115 °C the generated amounts of acrylamide were negligible during the monitoring time. At 125 °C addition of standard phenolic compounds reduced acrylamide formation which was more pronounced at initial time of heating (20 min) reaching up to 70%. Protocatechuic and gallic acid were more effective than trolox, caffeic and ferulic acid in acrylamide reduction at the final time intervals of heating (30–60 min). On the contrary, addition of VOO extract in the emulsion system resulted in a remarkable increase of acrylamide level, which was ascribed to secoiridoids’ structure containing aldehydic groups.     

Impact of oregano and virgin olive oil phenolic compounds on acrylamide content in a model system and fresh potatoes

In this study the effect of olive oil and oregano phenolic compounds on antioxidant activity (AOA) and acrylamide formation in a model system and fresh potatoes was evaluated. The addition of oregano phenolic extract in the model system resulted in an increase of AOA and in a reduction of acrylamide content, up to 49%, after heating. On the contrary, addition of olive oil extract resulted in AOA reduction and a concentration-dependent effect on acrylamide formation was observed with a reduction up to 15% (p < 0.05) followed by an increase up to 48%. The same trend, in acrylamide formation, was observed in fresh potatoes but to a lower extent. Finally, addition of tyrosol, oleuropein and p-hydroxyphenylacetic acid in the model system resulted in acrylamide reduction up to 50%. The discrepancy in acrylamide formation, caused by phenolic compounds, is ascribed to their structure and related to their terminal functional hydroxyl and aldehydic groups.     

Effect of oxygen reduction during malaxation on the quality of extra virgin olive oil (Cv. Carboncella) extracted through “two-phase” and “three-phase” centrifugal decanters

Quality and composition of virgin olive oil (VOO) are strictly dependent on complex processes that take place during the olive fruit crushing and malaxation of the olive paste. In this work, modulation of O₂ levels within malaxation chambers (R1: unmodified atmosphere; R2: oxygen: 12.73–4.64 kPa from the beginning to the end of malaxation; R3: 10.46–2.27 kPa; R4: 9.87–0.69 kPa) in two continuous “two-phase” and “three-phase” oil extraction plants was performed. Combined effects on the biosynthesis of nutritionally bioactive molecules and aroma volatiles and on the resulting sensory properties of the produced oils were investigated. Results showed that the type of oil extraction plant markedly affected the level of the phenolic compounds in the oil (and the related sensory attributes of bitter, pungency, astringency and bitter and pungency persistence). Reduction of O₂ concentration in the malaxing chamber, while having a minor impact on the presence of phenolic compounds, significantly affected the formation of all the examined volatiles. Particularly, lowered levels of oxygen hindered the formation of lipoxygenase derived volatiles weakening odours and flavours of artichoke, fresh fruity, and fresh cut grass.     

High performance size-exclusion chromatography analysis of polar compounds applied to refined, mild deodorized, extra virgin olive oils and their blends: An approach to their differentiation

An investigation was carried out to evaluate the use of High Performance Size-Exclusion Chromatography (HPSEC) of polar compounds of refined, mild deodorized, extra virgin olive oils as well as of their blends, in attempting to reveal significant differences in the amounts of the substance classes constituting polar compounds among these oils. Two sets of blends were prepared by mixing an extra virgin olive oil with both refined and mild deodorized olive oils in increasing amounts. The obtained data highlighted that the triacylglycerol oligopolymers were absent or present in traces in the extra virgin olive oil, while their mean amount was equal to 0.04 g/100 g and 0.72 g/100 g in mild deodorized and refined olive oils, respectively. Oxidized triacylglycerols and diacylglycerols were more abundant in mild deodorized oil and refined oil than in extra virgin olive oil. The Factorial Discriminant Analysis of the data showed that the HPSEC analysis could reveal the presence of refined/mild deodorized oils in extra virgin olive oils. In particular, the classification functions obtained allowed designation of mixtures containing at least 30 g/100 g of mild deodorized oil and all those containing refined olive oil as deodorized oil, therefore as oils subjected to at least a mild refining treatment.     

Aroma and physical characteristics of cakes prepared by replacing margarine with extra virgin olive oil

The effect of margarine substitution by extra virgin olive oil on the quality of Madeira cakes was studied. Three cakes containing either extra virgin olive oil or extra virgin olive oil/margarine mixture or margarine were prepared. The use of extra virgin olive oil increased batter density and cake volume while decreased the weight loss (%) during baking. Texture profile analysis also showed that the replacement of margarine by extra virgin olive oil affected significantly hardness and cohesiveness of the cakes. Headspace solid phase microextraction was applied in order to analyze the aroma of the three cakes. The addition of extra virgin olive oil produced a wide range of volatile compounds, which were analyzed by gas chromatography/mass spectrometry and were originated either from extra virgin olive oil or were produced during the baking process. Hedonic sensory tests were also conducted revealing that the cake prepared with extra virgin olive oil/margarine mixture was highly appreciated by the consumers as it got scores similar to control.     

Antioxidant activity of virgin olive oil phenolic compounds in a micellar system†

The antioxidant activity of two virgin olive oils, obtained from the same olive (Olea europaea sativa) batch but processed with different hammer crushing conditions, was evaluated by measuring their protective action towards linoleic acid peroxidation in a micellar system. The antioxidant efficiency (AE) of the oil phenolic fraction was higher when the olives were processed with a higher hammer crusher rotation rate. HPLC analysis demonstrated that one of the main derivatives of oleuropein, indicated as 3,4-DHPEA-EDA (the dialdehydic form of elenolic acid linked with 3,4-dihydroxyphenylethanol), is present only in the oil with higher AE. 3,4-DHPEA-EDA showed the greatest antioxidant ability among virgin olive oil phenols. Its greater efficiency in the micellar system in comparison with 3,4-dihydroxyphenylethanol (3,4-DHPEA) is related to its greater lipophilicity. It is suggested that the behaviour in the water–micellar environment is representative of that in a real system such as tomato-based sauce with added virgin olive oil. © 1999 Society of Chemical Industry     

A comparison between olive oil and extra-virgin olive oil used as covering liquids in canned dried tomatoes: hydrolytic and oxidative degradation during storage

The hydrolytic and oxidative degradation of olive oil and extra‐virgin olive oil, used as covering liquids in canned dried tomatoes, was studied during storage by means of conventional (acidity, peroxide value, p‐anisidine value) and non conventional (polar compounds) analyses. The effects of the addition of spices were also considered. The hydrolysis and oxidation of olive oil increased faster and was higher than that of extra‐virgin olive oil in terms of absolute values but some other indices, such as percentage of oligopolymers and percentage of oxidized triglycerides, increased faster in extra‐virgin olive oil than in olive oil. The antioxidant effect given by a higher concentration of polyphenols in the extra‐virgin olive oil was shown by a reduced amount of secondary oxidation. However, olive oil and extra‐virgin olive oils showed similar behaviour in terms of peroxide formation.     

Classification of ‘Chemlali’ accessions according to the geographical area using chemometric methods of phenolic profiles analysed by HPLC-ESI-TOF-MS

The present work describes a classification method of Tunisian ‘Chemlali’ olive oils based on their phenolic composition and geographical area. For this purpose, the data obtained by HPLC-ESI-TOF-MS from 13 samples of extra virgin olive oils, obtained from different production area throughout the country, were used for this study focusing in 23 phenolics compounds detected. The quantitative results showed a significant variability among the analysed oil samples. Factor analysis method using principal component was applied to the data in order to reduce the number of factors which explain the variability of the selected compounds. The data matrix constructed was subjected to a canonical discriminant analysis (CDA) in order to classify the oil samples. These results showed that 100% of cross-validated original group cases were correctly classified, which proves the usefulness of the selected variables.     

Acrylamide and 5-hydroxymethylfurfural formation during baking of biscuits: NaCl and temperature–time profile effects and kinetics

The present study aimed to investigate the effect of recipe and temperature–time on the formation of acrylamide and 5-hydroxymethylfurfural (HMF) during biscuit baking. Baking experiments were performed with biscuits of two different recipes, with and without NaCl, at 180 °C, 190 °C and 200 °C. Acrylamide and HMF reached highest concentrations at 200 °C for both recipes. The presence of NaCl in the biscuit formulation lowered acrylamide concentrations at 180 °C and 190 °C but not at 200 °C, and led to higher concentrations of HMF at all the tested temperatures. Sucrose hydrolysis was a key step in acrylamide and HMF formation during biscuit baking, even though a significant amount of acrylamide already had formed before the onset of sucrose hydrolysis. A lag phase was observed before sucrose hydrolysis occurred, which might depend on the melting of crystalline sucrose occurring at approximately 180 °C.A mathematical model based on the chemical reaction pathways was developed for the recipe with NaCl baked at 200 °C. The model described the chemical evolution during the last part of biscuit baking, and accurately predicted acrylamide and HMF content at the end of baking. The model showed the significant contribution of the reducing sugars to the formation of both acrylamide and HMF. The model could not be extended to the entire baking period because it was not possible to incorporate the lag phase observed before sucrose hydrolysis. The results reported in this study confirm that the kinetics of acrylamide and HMF formation in real food and dry systems may depend on the physical state of their precursors.     

Influence of chemical composition of olive oil on the development of volatile compounds during frying

In this study, 15 virgin olive oils from an industrial oil plant in the Abruzzo region were analyzed in terms of the volatile compounds responsible for the characteristic odor and olfactory perception of virgin olive oils and its modification upon frying (up to 60 min of heat treatment). Dynamic headspace–gas chromatography–mass spectrometry analysis was used to evaluate the volatile profile before and after each frying step and examine correlations with qualitative characteristic of oil (fatty acid composition, total phenolic compound content, tocopherols and pigments). The chemometric approach (genetic algorithms–partial least squares/multiple linear regression) developed for this study is a novel model for data treatment to select important variables in olive oil composition and understand their influence on spoilage during frying. An inverse correlation between oleic acid content and formation of toxic volatiles such as acrolein and crotonal during frying was demonstrated. Moreover, it was also observed that pigments such as chlorophylls, pheophytins, and carotenoids may prevent the formation of some aldehydes during frying.     

Phenolic compounds in virgin olive oils: influence of the degree of olive ripeness on organoleptic characteristics and shelf-life

 An experimental investigation was performed on virgin olive oils from Coratina and Ogliarola salentina cultivars extracted from green, partially blackened and totally blackened olives in order to evaluate changes in the organoleptic properties and in the shelf-life of the oil. The aim of the investigation was to identify the optimal stage of olive maturation for each cultivar to produce higher quality oils. Routine analyses in accordance with EC regulation no. 2568/91, the determination of phenols by HPLC and induction times were carried out. On the whole, the simple phenolic compounds increased as darker olives were used whereas the hydrolysable phenolic compounds decreased. In both the cultivars, total phenols and induction times were significantly higher in the oils obtained from green olives than in oils from totally blackened olives. Hence, it seems advisable to delay olive harvesting for cultivars usually yielding bitter to pungent oils (e.g. Coratina), but to anticipate harvesting for olives producing sweet tasting oils (e.g. O. Salentina). This would produce less bitter Coratina oils, with organoleptic features which may better fulfil consumers' expectations, and O. Salentina oils more resistant to oxidation. Received: 5 June 2000     

Prediction of Polyphenol Fraction in Virgin Olive Oil Using Mid-Infrared Attenuated Total Reflectance Attenuated Total Reflectance Accessory–Mid-Infrared Coupled With Partial Least Squares Regression

This study focuses on the quantification of virgin olive oil phenolic compound while using mid-infrared spectroscopy with chemometrics. For that, 100 samples of virgin olive oils in phenolic compounds which varied between 1.04 and 10.33 g/L were picked up in Morocco’s regions and subjected to infrared analysis. The aim was to develop a calibration model for the prediction of phenolic compounds in olive oil by using Fourier transform-infrared spectroscopy. The spectral transmissions of all samples were obtained in the spectral range of 600–4000 cm^–1. The values obtained for correlation coefficient and root mean square errors of prediction were 0.99 and 0.11, respectively. These results showed the capability of the Fourier transform-infrared spectroscopy and the chemometric in developing accurate models to predict the phenolic compounds in virgin olive oil.     

Impact of olive oil phenolic concentration on human plasmatic phenolic metabolites

Three different functional phenol-enriched virgin olive oils (FVOO) were prepared with a phenolic content of 250 (L-FVOO), 500 (M-FVOO), and 750 mg (H-FVOO) total phenols/kg. In a randomised, cross-over study with 12 healthy volunteers, the pharmacokinetics of phenolic biological metabolites was assessed. An increasing linear trend was observed for hydroxytyrosol sulfate, the main phenolic metabolite quantified in plasma, with C_max values of 1.35, 3.32, and 4.09 μmol/l, and AUC mean values of 263.7, 581.4, and 724.4 μmol/min for L-FVOO, M-FVOO, and H-FVOO, respectively. From our data an acute intake of phenol-enriched olive oils promotes a dose-dependent response of phenol conjugate metabolites in human plasma. Also, we point out for the first time hydroxytyrosol acetate sulfate as a main biological metabolite of hydroxytyrosol from olive oil ingestion.     

Characterization of the Maillard reaction in bread crisps

Maillard reaction (MR) is one of the main chemical event occurring during baking. To study the reaction in bakery products, a dry model system is more useful than an aqueous one. In this work, the effects of formulation and processing conditions in a crisp bread system were investigated to test the effects of different additives on both the overall reaction and the formation of MR products such as 5-hydroxymethyl-2-furaldehyde (HMF) and acrylamide. Cylindrical dough made up of flour, water and yeast was baked at 180 °C for 35 min and the slices were toasted at different times/temperatures combinations. Browning and water content were monitored along with the kinetic of formation of chemical indicators such as HMF and acrylamide also calculating rate constants and activation energy. These parameters were also monitored in systems added with glycine and asparaginase. During toasting water content follows an exponential trend, being the rate of water loss faster in the initial stage of toasting and at higher temperature. Browning was more intense when toasting at higher temperature and a linear correlations between browning (ΔL*, ΔE*), HMF and acrylamide concentration were observed when toasting at 180 °C. HMF and acrylamide content increased with the toasting time and temperature. Their concentrations were strongly dependent on the water content of the final product, and both the addition of glycine and asparaginase are effective in reducing acrylamide content. The addition of glycine enhanced the browning of toasted bread, and slightly increased HMF content at any toasting temperature. The system characterized in this work represents a suitable tool to study the development of the MR in dry systems.     

Use of 1-acetoxypinoresinol to authenticate Picual olive oils

Picual olive oils may represent 25% of the world olive oil production. This monovarietal oil is highly valued from a nutritional viewpoint because of its high content of monounsaturated acid and polyphenols. This study reports a method to authenticate virgin olive oils of the Picual variety. The method was based on the very low content of the lignan 1-acetoxypinoresinol in these oils. The compound, as well as the other phenolic substances, was extracted from oil by using N,N -dimethylformamide (DMF), the extract was washed with hexane and nitrogen was bubbled into the solution. The identification and quantification of the lignan used HPLC to separate, followed by UV, electrochemical, fluorescence and mass spectrometry detection or gas chromatography (GC) coupled to a mass spectrometry detector. UV detection offered low sensitivity and peaks coeluting with 1-acetoxypinoresinol were also observed. Mass spectrometry detection clearly discriminated between olive oils of Picual variety and other Spanish varieties. However, lignans show a very high response to fluorescence excitation, this detector is cheaper than mass spectrometry detectors and therefore it was considered as more appropriate for industrial uses. Thus, the latter method allowed discrimination between thirty-eight Picual olive oils and eight oils of the Hojiblanca, Cornicabra, Empeltre and Arbequina varieties. The paper also demonstrated the possibility of analysing all the phenolic compounds in virgin olive oil by fluorescence. Using this technique an easy methodology to authenticate Picual olive oils was developed.     

Use of capillary electrophoresis with UV detection to compare the phenolic profiles of extra‐virgin olive oils belonging to Spanish and Italian PDOs and their relation to sensorial properties

BACKGROUND: There is much interest in foods that belong to Protected Designations of Origin (PDO) because the quality and other essential and exclusive characteristics are guaranteed because of a particular geographical environment. We have used a capillary electrophoretic method for the simple, rapid and simultaneous characterization and quantification of the polyphenolic fraction of extra‐virgin olive oil from different PDOs (18 compounds in less than 7 min). To demonstrate the usefulness of this method, we have analyzed 16 samples of a Spanish PDO and nine other samples belonging to an Italian PDO (n = 5). RESULTS: In this way, it was possible to compare the phenolic profiles of the oils of different zones of the same PDO, as well as the phenolic profiles of Spanish and Italian extra‐virgin olive oils. Univariate statistics were used for differentiating the oils produced in each PDO. Furthermore, the correlations among several of the phenolic compounds present in the extracts of olive oil and its sensorial properties were checked. decarboxylated oleuropein aglycon (DOA) (b) (peak 6) was the compound more related to the bitterness of the oils, Ac Pin (peak number 4) and the unidentified peak with t_mig 4.025 min played an important role in the pungent taste of the oils, and these two latter compounds and the peak 13 seemed to be related to the fruitiness of the oils. CONCLUSIONS: The electrophoretic method described in the current work has the ability to detect and quantify simultaneously 18 phenolic compounds (belonging to five different families) in less than 7 min. This technique could improve the characterization of this polar fraction and determine the geographical origin of olive oils or detect possible ‘PDO markers’. In fact, capillary electrophoresis coupled to statistical analysis enabled discrimination among olive oils belonging to two different PDOs considering eight phenolic compounds present in the extracts, and also identification of the phenolic compounds which could have more influence on several sensory attributes such as bitterness, pungency and fruitiness. Copyright © 2009 Society of Chemical Industry     

Phenolic content of commercial olive oils

The phenolic composition of commercial virgin olive oils (Picual, Hojiblanca, Arbequina and Cornicabra varieties) was studied by high performance liquid chromatography, sampling oils over 1 year. Oils sold in March displayed the lowest polyphenol concentration, particularly in secoiridoid aglycons. In contrast, lignans and tocopherols concentrations were not affected by sampling date. Among varieties, Picual and Cornicabra oils had slightly higher concentrations of polyphenols than Hojiblanca and Arbequina. Overall, the concentration of polyphenols in commercial Spanish virgin olive oils ranged from 330 to 500 mg/kg oil, which is higher than data reported previously. In contrast, "olive oil" and "pomace-olive oil" (mixtures of refined and virgin olive oils) had much lower concentrations in polyphenols than virgin olive oil, although higher than other edible vegetable oils. Thus, olive oil can be considered a good source of natural antioxidants. Moreover, the polyphenol and tocopherol contents of virgin olive oils were also found useful for the classification of the different commercial monovarietal oils when analysing the data by chemometric methods.     

Chemical composition and oxidative stability of Tunisian monovarietal virgin olive oils with regard to fruit ripening

The chemical composition of virgin olive oil may be influenced by genotype and different agronomic (i.e. fruit ripeness degree, water supply) and technological factors. This article reports the evaluation of the influence of the olive ripening stage on the quality indices, the major and the minor components and the oxidative stability of the two main monovarietal Tunisian cultivars (cvv. Chétoui and Chemlali) virgin olive oils. Moreover, the olives cv. Chétoui were tested in a rain-fed control and an irrigation regime. The oils sampled at five different ripeness stages were submitted to liquid chromatographic determination (HPLC-DAD/MSD) of their quali-quantitative phenolic and tocopherolic profiles. Moreover, the triacylglycerol and fatty acid compositions, and minor components such as squalene, pigments and their relation with the oil oxidative stability were evaluated. The tested oils showed very good correlation between the oxidative stability and the concentrations of total phenols, practically secoiridoids and α-tocopherol.     

Changes in volatile compounds and oil quality with malaxation time of Tunisian cultivars of Olea europea

While there has been considerable work examining the effect of malaxation time on different characteristics of olive oils, there have been few that deal with all the major aspects. Here, the influence of malaxation time was evaluated using major local Tunisian (cv. Chemlali and Chetoui) cultivars. Standard characteristics were measured as well as detailed analyses of volatile compounds were conducted. Headspace solid‐phase microextraction (HS‐SPME) was applied to the analysis of volatile compounds of virgin olive oils from Chemlali and Chetoui varieties with differing malaxation time. Twenty‐seven compounds were characterised by GC‐FID and GC–MS. Compounds belonging mainly to alcohols, esters, aldehydes, ketones and hydrocarbons chemical classes characterized the volatile profile. Significant differences in the proportion of volatiles from oils of different malaxation time were detected. The results suggest that besides genetic factors, malaxation time influences volatile formation. The main variables that were affected by malaxation time were the total amount of phenols and composition of the volatile compounds. At malaxation time of 30 min, Chemlali and Chetoui olive oils presented the highest total phenol content (244.19 and 877.63 mg kg^?1, respectively), while the lowest content was observed at 60 min from regardless of cultivars. In turn, this influenced the oxidative stability and peroxide value. It was also clear that the cultivars behaved differently and this prevented general conclusions being made for all of the quality characteristics.     

Analytical evaluation of two monovarietal virgin olive oils cultivated in the south of Tunisia: Jemri‐Bouchouka and Chemlali‐Tataouin cultivars

BACKGROUND: The characterisation of virgin olive oils from two Tunisian cultivars, growing in the Tataouin zone, namely Jemri‐Bouchouka, a rare olive cultivar, and Chemlali‐Tataouin, was carried out. Several analytical parameters were evaluated; these include quality index, fatty acids, phenolic, chlorophyll, carotenoid, squalene, α‐tocopherol compositions and oxidative stability. RESULTS: Jemri‐Bouchouka olive oil had the highest value of oleic acid (74.50%) while Chemlali‐Tataouin was characterised by a high percentage of palmitic acid (14.75%), which makes this oil freeze at a low temperature. On the other hand, Jemri‐Bouchouka oil was characterised by a low phenolic and α‐tocopherol content (267.72 mg GAE kg^?1 and 278.34 mg kg^?1, respectively). Ten phenolic compounds were identified. The main phenols found in the two olive oils were oleuropein aglycon and pinoresinol. All phenolic compounds showed significant correlations with oxidative stability. CONCLUSION: The analytical parameters of virgin olive oil that were determined in this study were greatly influenced by cultivar. © 2012 Society of Chemical Industry