Olive Oil Phenolic Compounds Research Articles

Oleuropein improves insulin resistance in skeletal muscle by promoting the translocation of GLUT4.

As the beneficial effects of the Mediterranean diet on human health are well established, the phenolic compounds in olive oil have been gaining interest. Oleuropein, a major phenolic compound in olives, is known to reduce the blood glucose levels in alloxan-induced diabetic rats and rabbits, however, its effect on type 2 diabetes caused by obesity is not clear. The purpose of this study is clarifying the effect of oleuropein on the glucose tolerance in skeletal muscle under the condition of lipotoxicity caused by type 2 diabetes. Oleuropein enhanced glucose uptake in C2C12 cells without insulin. Translocation of glucose transporter 4 (GLUT4) into the cell membrane was promoted by activation of adenosine monophosphate-activated protein kinase (AMPK) but not protein kinase B (Akt). Physiological concentration of oleuropein (10 µM) was sufficient to express beneficial effects on C2C12 cells. Oleuropein prevented palmitic acid-induced myocellular insulin resistance. Furthermore, in gastrocnemius muscles of mice fed a high fat diet, oleuropein also induced the GLUT4 localization into cell membrane. These results suggest the possibility of oleuropein to be effective for type 2 diabetes by reducing insulin resistance in skeletal muscles.

The Health Benefiting Mechanisms of Virgin Olive Oil Phenolic Compounds.

Virgin olive oil (VOO) is credited as being one of the many healthful components associated with the Mediterranean diet. Mediterranean populations experience reduced incidence of chronic inflammatory disease states and VOO is readily consumed as part of an everyday Mediterranean dietary pattern. VOO is rich in phenolic compounds and the health promoting benefits of these phenolics are now established. Recent studies have highlighted the biological properties of VOO phenolic compounds elucidating their anti-inflammatory activities. This paper will review current knowledge on the anti-inflammatory and nutrigenomic, chemoprotective and anti-atherosclerotic activities of VOO phenolics. In addition the concentration, metabolism and bioavailability of specific phenolic compounds will be discussed. The evidence presented in the review concludes that oleurepein, hydroxytyrosol and oleocanthal have potent pharmacological activities in vitro and in vivo; however, intervention studies with biologically relevant concentrations of these phenolic compounds are required.

219 - Optical Non Destructive UV-VIS-NIR Spectroscopic Tools and Chemometrics in the Monitoring of Olive Oil Phenolic Compounds and Oxidation

Olive oil is a high quality natural product typical of the Mediterranean area and its nutritional and sensory properties are mainly attributed to the presence of minor phenolic compounds. The phenolic compounds are important antioxidants and responsible for the olive oil oxidation stability an important quality factor of olive oil storage. Moreover, phenols are the main contributors to the typical taste of the highest quality virgin olive oil and may also contribute to the prevention of several human diseases. Because of technical difficulties in the quantitative determination of phenolic compounds using the classical instrumental analytical methods it is important to study the application of alternative methods such as UV-VIS-NIR spectroscopy. In this review study, several applications of UV-VIS-NIR spectroscopy in off-on line monitoring of olive oil phenolic compounds and oxidation status have been considered in combination with the appropriately used spectra preprocessing and data analysis by using chemometric tools.

Anti-inflammatory effects of tyrosol in streptozotocin-induced diabetic Wistar rats

The anti-inflammatory effect of tyrosol (4-(2-hydroxyethyl)), a phenolic compound in olive oil (20 mg/kg body weight), in streptozotocin (STZ)-induced diabetic rat was evaluated. Diabetic rats showed significant (P < 0.05) increase in plasma glucose and lipid peroxidation products and significant (P < 0.05) decrease in plasma insulin and enzymatic and non-enzymatic antioxidants in the liver and pancreas. The levels of inflammatory marker, C-reactive protein in plasma and protein expressions of nuclear factor-kappa B p65, tumour necrosis factor-alpha and interleukin-6 in the liver and pancreas were significantly (P < 0.05) increased in STZ-induced diabetic rats. Conversely, daily oral treatment with tyrosol for 45 days significantly (P < 0.05) restored all the above mentioned parameters to near normal levels. The immunohistochemical studies confirm the anti-inflammatory effects of tyrosol. Tyrosol exerts anti-inflammatory effects on the liver and pancreas of STZ-induced diabetic rats via its antioxidant activity, hence it may play an important role in the management of diabetes mellitus.

Antioxidant Behavior of Olive Phenolics in Oil-in-Water Emulsions.

The effect of the surrounding molecular environment (β-lactoglobulin as an emulsion stabilizer and maltodextrin as a viscosity modifier) on the antioxidant activity of three olive oil phenolic compounds (PCs) in olive oil-in-water emulsions was investigated. Oxidation potential, phenolic partitioning, and radical quenching capacity were assessed in solution and in emulsion for oleuropein, hydroxytyrosol, and tyrosol; the influence of β-lactoglobulin and maltodextrin concentration was also evaluated. Finally, the observed properties were related to the oxidative stability of the emulsions containing the PCs to explain their behavior. The order hydroxytyrosol > oleuropein > tyrosol was observed among the antioxidants for both oxidation potential and radical quenching activity. Radical quenching capacity in emulsion and anodic potential were complementary indices of antioxidant effectiveness. As the intrinsic susceptibility of an antioxidant to oxidation expressed by its anodic potential decreased, the environmental conditions (molecular interactions and changes in continuous phase viscosity) played a major role in the antioxidant effectiveness in preventing hydroperoxide decomposition.

Towards green analysis of virgin olive oil phenolic compounds: Extraction by a natural deep eutectic solvent and direct spectrophotometric detection

The determination of phenolic compounds in extra virgin olive oils (EVOO) by means of rapid, low-cost, environment-free methods would be a desirable achievement. A natural deep eutectic solvent (DES) based on glucose and lactic acid was considered as extraction solvent for phenolic compounds in EVOO. DESs are green solvents characterized by high availability, biodegradability, safety, and low cost. The spectrophotometric characteristics of DES extracts of 65 EVOO samples were related to the total phenolic content of the oils, assessed by methanol-water extraction coupled to the Folin-Ciocalteu assay. A regression model (ncalibration=45, nvalidation=20), including the absorbance at two wavelengths (257, 324nm), was obtained, with an adjusted R2=0.762. Therefore the DES could provide a promising and viable approach for a green screening method of phenolic compounds in EVOO, by means of simple spectrophotometric measurements of extracts, even for on-field analysis (for example in olive mills).

Influence of Phenol-Enriched Olive Oils on Human Intestinal Immune Function.

Olive oil (OO) phenolic compounds (PC) are able to influence gut microbial populations and metabolic output. Our aim was to investigate whether these compounds and changes affect the mucosal immune system. In a randomized, controlled, double blind cross-over human trial, for three weeks, preceded by two-week washout periods, 10 hypercholesterolemic participants ingested 25 mL/day of three raw virgin OO differing in their PC concentration and origin: (1) an OO containing 80 mg PC/kg (VOO); (2) a PC-enriched OO containing 500 mg PC/kg from OO (FVOO); and (3) a PC-enriched OO containing a mixture of 500 mg PC/kg from OO and thyme (1:1, FVOOT). Intestinal immunity (fecal immunoglobulin A (IgA) and IgA-coated bacteria) and inflammation markers (C-reactive protein (CRP) and fecal interleukin 6 (IL-6), tumor necrosis factor α (TNFα) and calprotectin) was analyzed. The ingestion of high amounts of OO PC, as contained in FVOO, tended to increase the proportions of IgA-coated bacteria and increased plasma levels of CRP. However, lower amounts of OO PC (VOO) and the combination of two PC sources (FVOOT) did not show significant effects on the variables investigated. Results indicate a potential stimulation of the immune system with very high doses of OO PC, which should be further investigated.

Phenolic Compounds in Extra Virgin Olive Oil Stimulate Human Osteoblastic Cell Proliferation.

In this study, we aimed to clarify the effects of phenolic compounds and extracts from different extra virgin olive oil (EVOO) varieties obtained from fruits of different ripening stages on osteoblast cells (MG-63) proliferation. Cell proliferation was increased by hydroxytyrosol, luteolin, apigenin, p-coumaric, caffeic, and ferulic acids by approximately 11–16%, as compared with controls that were treated with one vehicle alone, while (+)-pinoresinol, oleuropein, sinapic, vanillic acid and derivative (vanillin) did not affect cell proliferation. All phenolic extracts stimulated MG-63 cell growth, and they induced higher cell proliferation rates than individual compounds. The most effective EVOO phenolic extracts were those obtained from the Picual variety, as they significantly increased cell proliferation by 18–22%. Conversely, Arbequina phenolic extracts increased cell proliferation by 9–13%. A decline in osteoblast proliferation was observed in oils obtained from olive fruits collected at the end of the harvest period, as their total phenolic content decreases at this late stage. Further research on the signaling pathways of olive oil phenolic compounds involved in the processes and their metabolism should be carried out to develop new interventions and adjuvant therapies using EVOO for bone health (i.e.osteoporosis) in adulthood and the elderly.

Olive oil phenolic compounds and high-density lipoprotein function.

The functional capacities of high-density lipoproteins (HDLs) reflect the physiological role of the particle better than the quantity of HDL cholesterol. Owing to its phenolic compounds, the consumption of virgin olive oil has emerged as a promising therapy to promote these capacities. This review highlights the human studies that explain these benefits and explores some possible mechanisms. The consumption of olive oil phenolic compounds increased the ability of HDLs to pick up cholesterol excess in peripheral cells (the cholesterol efflux capacity). Olive oil phenolic compounds have also been shown to improve HDL antioxidant capacities and some anti-inflammatory traits. These changes respond to an improvement of HDL oxidative status and composition. Novel strategies to increase HDL functional capacities are in demand from clinicians. The attainment of a fully-functional HDL through dietary or lifestyle changes is a priority in cardiovascular research. Within this context, the consumption of virgin olive oil, because of its phenolic compounds, may be a relevant protective approach. Further studies in large-scale, randomized controlled trials are, however, required to confirm these effects in HDL functionality.

Olive Oil Phenolic Compounds: May Prevent Cancer in Human?

Olive Oil Phenolic Compounds: May Prevent Cancer in Human?

Effect of olive oil phenolic compounds on the expression of blood pressure-related genes in healthy individuals.

To investigate whether the ingestion of olive oil having different phenolic contents influences the expression of blood pressure-related genes, involved in the renin-angiotensin-aldosterone system, in healthy humans. A randomized, double-blind, crossover human trial with 18 healthy subjects, who ingested 25mL/day of olive oils (1) high (366mg/kg, HPC) and (2) low (2.7mg/kg, LPC) in phenolic compounds for 3weeks, preceded by 2-week washout periods. Determination of selected blood pressure-related gene expression in peripheral blood mononuclear cells (PBMNC) by qPCR, blood pressure and systemic biomarkers. HPC decreased systolic blood pressure compared to pre-intervention values and to LPC, and maintained diastolic blood pressure values compared to LPC. HPC decreased ACE and NR1H2 gene expressions compared with pre-intervention values, and IL8RA gene expression compared with LPC. The introduction to the diet of an extra-virgin olive oil rich in phenolic compounds modulates the expression of some of the genes related to the renin-angiotensin-aldosterone system. These changes could underlie the decrease in systolic blood pressure observed.

Effect of virgin olive oil and thyme phenolic compounds on blood lipid profile: implications of human gut microbiota.

To investigate the effect of virgin olive oil phenolic compounds (PC) alone or in combination with thyme PC on blood lipid profile from hypercholesterolemic humans, and whether the changes generated are related with changes in gut microbiota populations and activities. A randomized, controlled, double-blind, crossover human trial (n=12) was carried out. Participants ingested 25mL/day for 3weeks, preceded by 2-week washout periods, three raw virgin olive oils differing in the concentration and origin of PC: (1) a virgin olive oil(OO) naturally containing 80mgPC/kg, (VOO), (2) a PC-enriched virgin olive oil containing 500mgPC/kg, from OO (FVOO), and (3) a PC-enriched virgin olive oil containing a mixture of 500mgPC/kg from OO and thyme, 1:1 (FVOOT). Blood lipid values and faecal quantitative changes in microbial populations, short chain fatty acids, cholesterol microbial metabolites, bile acids, and phenolic metabolites were analysed. FVOOT decreased seric ox-LDL concentrations compared with pre-FVOOT, and increased numbers of bifidobacteria and the levels of the phenolic metabolite protocatechuic acid compared to VOO (P<0.05). FVOO did not lead to changes in blood lipid profile nor quantitative changes in the microbial populations analysed, but increased the coprostanone compared to FVOOT (P<0.05), and the levels of the faecal hydroxytyrosol and dihydroxyphenylacetic acids, compared with pre-intervention values and to VOO, respectively (P<0.05). The ingestion of a PC-enriched virgin olive oil, containing a mixture of olive oil and thyme PC for 3weeks, decreases blood ox-LDL in hypercholesterolemic humans. This cardio-protective effect could be mediated by the increases in populations of bifidobacteria together with increases in PC microbial metabolites with antioxidant activities.

Comparing two metabolic profiling approaches (liquid chromatography and gas chromatography coupled to mass spectrometry) for extra-virgin olive oil phenolic compounds analysis: A botanical classification perspective

Over the last decades, the phenolic compounds from virgin olive oil (VOO) have become the subject of intensive research because of their biological activities and their influence on some of the most relevant attributes of this interesting matrix. Developing metabolic profiling approaches to determine them in monovarietal virgin olive oils could help to gain a deeper insight into olive oil phenolic compounds composition as well as to promote their use for botanical origin tracing purposes. To this end, two approaches were comparatively investigated (LC–ESI–TOF MS and GC–APCI–TOF MS) to evaluate their capacity to properly classify 25 olive oil samples belonging to five different varieties (Arbequina, Cornicabra, Hojiblanca, Frantoio and Picual), using the entire chromatographic phenolic profiles combined to chemometrics (principal component analysis (PCA) and partial least square-discriminant analysis (PLS–DA)). The application of PCA to LC–MS and GC–MS data showed the natural clustering of the samples, seeing that 2 varieties were dominating the models (Arbequina and Frantoio), suppressing any possible discrimination among the other cultivars. Afterwards, PLS–DA was used to build four different efficient predictive models for varietal classification of the samples under study. The varietal markers pointed out by each platform were compared. In general, with the exception of one GC–MS model, all exhibited proper quality parameters. The models constructed by using the LC–MS data demonstrated superior classification ability.

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.

Stability of Virgin Olive Oil Phenolic Compounds during Long-Term Storage (18 Months) at Temperatures of 5-50 °C.

Virgin olive oil (VOO) phenolic compounds have high nutritional and biological properties. The purpose of this research was to study the stability of VOO phenolic compounds during long-term storage (18 months) at different temperatures (5, 15, 25, and 50 °C) and to verify the advantage of storing VOO at a temperature lower than the usual commercial conditions (20-25 °C). Four monovarietal VOOs that differed in their fatty acid profile and content of natural antioxidants were used in this study. The degradation of secoiridoid phenolics during storage displayed pseudo-first-order kinetics and depended on the initial content of phenolics related to olive oil variety. The initial degradation rate was similar at 5 and 15 °C but increased considerably at 25 °C and was even faster at 50 °C. Tyrosol derivatives were more stable than hydroxytyrosol compounds, especially in closed bottles with limited oxygen availability. The increase in the content of simple phenolics, the decrease of their secoiridoid derivatives, or the ratio of simple to secoiridoid phenolics could be used as indices of the oxidative and hydrolytic degradation of VOO phenolics. The shelf life of the studied VOO was considerably extended at reduced storage temperature (15 vs 25 °C). Moreover, storage conditions affected VOO phenolic content and therefore the expiration date of the health claim that olive oil polyphenols contribute to the protection of blood lipids from oxidative stress.

Complementary phenol-enriched olive oil improves HDL characteristics in hypercholesterolemic subjects. A randomized, double-blind, crossover, controlled trial. The VOHF study.

Consumption of olive oil (OO) phenolic compounds (PCs) has beneficial effects on lipid profile. HDL functionality is currently considered to be a more important issue than its circulating quantity. Our aim was to assess whether functional virgin olive oils (FVOOs), one enriched with its own PC (500 ppm; FVOO) and another with OOPC (250 ppm) plus additional complementary PCs from thyme (250 ppm) (total: 500 ppm; FVOOT (functional virgin olive oil with thyme)), could improve HDL functionality related properties versus a virgin OO control (80 ppm; VOO). In a randomized, double-blind, crossover, controlled trial, 33 hypercholesterolemic volunteers received 25 mL/day of VOO, FVOO, and FVOOT during 3 wk. HDL cholesterol increased 5.74% (p < 0.05) versus its baseline after the FVOOT consumption in the participants without hypolipidemic medication. We detected, after FVOOT consumption, an increase in HDL2 -subclass (34.45, SD = 6.38) versus VOO intake (32.73, SD = 6.71). An increment in esterified cholesterol/free cholesterol and phospholipids/free cholesterol in HDL was observed after FVOOT consumption (1.73, SD = 0.56; 5.44, SD = 1.39) compared with VOO intervention (1.53, SD = 0.35; 4.97, SD = 0.81) and FVOO intervention (1.50, SD = 0.33; 4.97, SD = 0.81). Accordingly, lecithin-cholesterol acyltransferase mass increased after FVOOT consumption (1228 μg/mL, SD = 130), compared with VOO consumption (1160 μg/mL, SD = 144). An improvement in HDL oxidative-status was reflected after FVOOT consumption versus its baseline, given an increment in the paraoxonase activity (118 × 10(3) U/L, SD = 24). FVOOT improves HDL-subclass distribution and composition, and metabolism/antioxidant enzyme activities. FVOOT could be a useful dietary tool in the management of high cardiovascular risk patients.

Effect of intracerebral hydroxytyrosol and its nitroderivatives on striatal dopamine metabolism: A study by in vivo microdialysis.

The natural phenolic oil compound hydroxytyrosol (HTy) is widely studied because of its antioxidant and neuroprotective properties. Nitroderivatives of HTy have been studied in order to evaluate their putative effects on catechol-O-methyltransferase (COMT) activity. To study its effect on dopamine metabolism, nitrohydroxytyrosol and its lipophilic derivatives (nitrohydroxytyrosyl acetate and ethyl nitrohydroxytyrosyl ether), were administered into the rat corpus striatum through a microdialysis probe. Other catechols (HTy and the known COMT inhibitor Ro 41-0960) were also studied for comparison. The olive oil phenolic compounds (nitroderivatives and HTy) increased extracellular levels of 3,4-dihydroxyphenylacetic acid during the perfusion with similar maximum values to that of Ro 41-0960 when comparing to basal dialysate levels (approximately 140%). None of the compound series produced a decrease in the homovanillic acid extracellular levels below 75%. Among all novel compounds studied, both lipophilic nitrocatechols (nitrohydroxytyrosyl acetate and ethyl nitrohydroxytyrosyl ether) showed a long-acting effect over time once the perfusion through the microdialysis probe ended. In accordance with the actual design of novel COMT inhibitors with a long profile, our results suggest a certain influence of the side chain substituent on the COMT activity that could provide new lipophilic COMT inhibitors.

Influence of olive oil phenolic compounds on headspace aroma release by interaction with whey proteins.

The release of volatile compounds in an oil-in-water model system obtained from olive oil-whey protein (WP) pairing was investigated by considering the effect of phenolic compounds. Human saliva was used to simulate mouth conditions by retronasal aroma simulator (RAS) analysis. Twelve aroma compounds were quantified in the dynamic headspace by SPME-GC/MS. The results showed significant influences of saliva on the aroma release of virgin olive oil (VOO) volatiles also in the presence of WP. The interaction between WP and saliva leads to lower headspace release of ethyl esters and hexanal. Salivary components caused lower decrease of the release of acetates and alcohols. A lower release of volatile compounds was found in the RAS essay in comparison to that in orthonasal simulation of only refined olive oil (without addition of saliva or WP), with the exception of hexanal and 1-penten-3-one, where a significantly higher release was found. Our results suggest that the extent of retronasal odor (green, pungent) of these two volatile compounds is higher than orthonasal odor. An extra VOO was used to verify the release in model systems, indicating that WP affected aroma release more than model systems, while saliva seems to exert an opposite trend. A significant increase in aroma release was found when phenolic compounds were added to the system, probably due to the contrasting effects of binding of volatile compounds caused by WP, for the polyphenol-protein interaction phenomenon. Our study could be applied to the formulation of new functional foods to enhance flavor release and modulate the presence and concentrations of phenolics and whey proteins in food emulsions/dispersions.

Interaction between extra virgin olive oil phenolic compounds and mucin

Extra virgin olive oil (EVOO) phenolic compounds provide nutritional benefits because of their antioxidant capacity. The interaction between phenolic compounds and proteins may reduce their bioavailability and antioxidant capacity. The objective of this project was to evaluate the interaction between phenolic compounds from EVOO and mucin (protein produced by epithelial tissues). EVOO phenolic extract and a number of commercially available pure phenolics present in EVOO were also used in this study: cinnamic, p‐coumaric, caffeic, vanillic and protocatechuic acids, tyrosol, hydroxytyrosol and oleuropein. The interaction between polyphenols and proteins was measured by monitoring the increasing turbidity of the reaction mixture and expressed in nephelometric turbidity units. Polyphenol solutions at different concentrations were mixed with mucin solutions. Reaction mixtures were measured after 1, 30, 60, 90 and 180 min at 37°C. The results suggest that EVOO polyphenols interact with the mucin solution forming an insoluble complex after 1 min of reaction. The highest interaction between polyphenols and proteins was observed for the EVOO phenolic extract and cinnamic, p‐coumaric and caffeic acids. The interaction between polyphenols and mucin varied depending on the phenol concentration and chemical structure. The importance of the results is to evaluate the possible consequences of EVOO phenolic–protein interactions in the bioavailability and antioxidant capacity of the polyphenols present in the EVOO.Practical applications: Nephelometry is a simple method for the evaluation of the interaction between phenolic extract from EVOO and mucin. Phenolic compounds interact with mucin and this could provide information about possible negative consequences for the bioavailability of polyphenols and finally for the health benefits of EVOO. Additionally, this method could complement sensorial analysis for evaluation of the astringency of EVOOs, according to their polyphenol profiles.Schematic representation of the stages occurring in binding and precipitation of polyphenol by mucin. Adapted from [30, 45].

Potential role of olive oil phenolic compounds in the prevention of neurodegenerative diseases.

Adherence to the Mediterranean Diet (MD) has been associated with a reduced incidence of neurodegenerative diseases and better cognitive performance. Virgin olive oil, the main source of lipids in the MD, is rich in minor phenolic components, particularly hydroxytyrosol (HT). HT potent antioxidant and anti-inflammatory actions have attracted researchers’ attention and may contribute to neuroprotective effects credited to MD. In this review HT bioavailability and pharmacokinetics are presented prior to discussing health beneficial effects. In vitro and in vivo neuroprotective effects together with its multiple mechanisms of action are reviewed. Other microconstituents of olive oil are also considered due to their potential neuroprotective effects (oleocanthal, triterpenic acids). Finally, we discuss the potential role of HT as a therapeutic tool in the prevention of neurodegenerative diseases.