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Wild olive oil (WOO) derives from naturally occurring wild olive trees. WOO has received increasing attention over the last decade, in response to the growing demand of the consumer for high-quality food products which may also provide health benefits. This study provides a comprehensive review of the available studies concerning the chemical composition of WOO produced across diverse geographical regions. The composition of WOO is characterized by the presence of acylglycerols (mainly triacylglycerols), biophenols, sterols, tocopherols, pigments, and triterpene alcohols. Many of these compounds present important variations depending on the wild olive tree subspecies and the specific ecological niches of production. Further, the presence of phenolic and volatile fraction may contribute to the fruity, bitter, and pungent flavor notes of WOO. The concentration of several compounds (e.g. phenols) are comparable to those found in olive oils from cultivated varieties, while sterol levels consistently surpass the international standard of 1000 mg/kg for all olive oils (extra virgin, virgin and refined). Both the qualitative and quantitative characteristics of the chemical profile of WOO underscore its potential as a viable alternative edible oil., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Ltd. All rights reserved.)

Essential oils (EOs) are gaining importance as sustainable food antioxidants, but kinetic data on peroxyl radical trapping are missing. Thirteen EOs from 11 botanical species were studied in the inhibited autoxidation of cumene by oxygen-uptake kinetics. EOs of Juniperus oxycedrus , Syzygium aromaticum , Thymus vulgaris , Thymbra capitata , Betula alba , Pimenta racemosa , and Satureja montana , containing 23-86% phenolic components by gas chromatography/mass spectrometry (GC-MS) analysis, afforded inhibition rate constants k inh in the order of 10 4 M -1 s -1 -butyl-4-methylphenol) (BHT). They matched or outperformed BHT in the protection of olive oil. The EOs tert -butyl-4-methylphenol) (BHT). They matched or outperformed BHT in the protection of olive oil. The EOs Daucus carota with <1% phenols and those of Cedrus atlantica with <1% phenols and those of Apium graveolens and Tagetes minuta with no phenolics had no chain-breaking activity. Key components carvacrol, thymol, eugenol, dihydroeugenol, umbelliferone, conyferyl alcohol, o -cresol, m -cresol, p -cresol, 4-allylphenol, 2,3-xylenol, 2,4-xylenol, and phenol had k inh in the range of 10 3 -10 4 M -1 s -1 and, along with EOs containing them, could potentially replace BHT in the protection of food products.

Olive oil is an indispensable part of the diet in Mediterranean regions, and is appreciated worldwide for its sensory characteristics, combining a fine aroma and pleasant flavor with the high nutritional value of specific chemical compounds. However, making rapid measurements of phenolic compounds is a major challenge for the olive oil sector. The development of a new method based on near infrared (NIR) spectroscopy may be considered an important advance for the sector, as it is rapid, low-cost, non-contaminant and non-destructive. In this study, three different NIR instruments - one FT-NIR benchtop instrument (671.82-2702.70 nm) and two low-cost portable devices (900-1700 nm and 1350-2150 nm) - were used to analyze a collection of virgin olive oil samples from various Mediterranean regions. To predict both the individual and total concentration of phenols in the olive oil, four signal pretreatment methods and modified partial least squares regression analyses were employed to develop the predictive models. The results showed that the benchtop FT-NIR instrument performed better than the other portable instruments when measuring the phenolic compounds in virgin olive oil. The best models of hydroxytyrosol derivatives, tyrosol derivatives, total phenols and "EFSA phenols" showed R 2 cv values were 2.51, 2.61, 2.93 and 2.95, respectively. Meanwhile, for the portable NIR instruments, the prediction models for hydroxytyrosol derivatives, total phenols and "EFSA phenols" (the sum of the hydroxityrosol and tyrosol derivatives) showed R cv values were 2.51, 2.61, 2.93 and 2.95, respectively. Meanwhile, for the portable NIR instruments, the prediction models for hydroxytyrosol derivatives, total phenols and "EFSA phenols" (the sum of the hydroxityrosol and tyrosol derivatives) showed R 2 between 2 and 2.5. These results indicate the great potential of NIR, both with benchtop and portable devices, to detect phenolic compounds in virgin olive oil, which can guarantee the quality of virgin olive oil and thus aid progress in the olive oil industry. Moreover, this is the first published work to determine phenolic compounds in virgin olive oil using portable NIR instruments.cv values ranging between 0.75 and 0.81 and an RPD cv between 2 and 2.5. These results indicate the great potential of NIR, both with benchtop and portable devices, to detect phenolic compounds in virgin olive oil, which can guarantee the quality of virgin olive oil and thus aid progress in the olive oil industry. Moreover, this is the first published work to determine phenolic compounds in virgin olive oil using portable NIR instruments., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 The Authors. Published by Elsevier B.V. All rights reserved.)

The olive tree ( Olea europaea ) and olive oil hold significant cultural and historical importance in Europe. The health benefits associated with olive oil consumption have been well documented. This paper explores the mechanisms of the anti-cancer effects of olive oil and olive leaf, focusing on their key bioactive compounds, namely oleocanthal, oleacein, and oleuropein. The chemopreventive potential of oleocanthal, oleacein, and oleuropein is comprehensively examined through this systematic review. We conducted a systematic literature search to identify eligible articles from Scopus, PubMed, and Web of Science databases published up to 10 October 2023. Among 4037 identified articles, there were 88 eligible articles describing mechanisms of chemopreventive effects of oleocanthal, oleacein, and oleuropein. These compounds have the ability to inhibit cell proliferation, induce cell death (apoptosis, autophagy, and necrosis), inhibit angiogenesis, suppress tumor metastasis, and modulate cancer-associated signalling pathways. Additionally, oleocanthal and oleuropein were also reported to disrupt redox hemostasis. This review provides insights into the chemopreventive mechanisms of O. europaea -derived secoiridoids, shedding light on their role in chemoprevention. The bioactivities summarized in the paper support the epidemiological evidence demonstrating a negative correlation between olive oil consumption and cancer risk. Furthermore, the mapped and summarized secondary signalling pathways may provide information to elucidate new synergies with other chemopreventive agents to complement chemotherapies and develop novel nutrition-based anti-cancer approaches.

Three Portuguese olive oils with PDO ('Azeite do Alentejo Interior', 'Azeites da Beira Interior' and 'Azeite de Trás-os-Montes') were studied considering their physicochemical quality, antioxidant capacity, oxidative stability, total phenols content, gustatory sensory sensations and Fourier transform infrared (FTIR) spectra. All oils fulfilled the legal thresholds of EVOOs and the PDO's specifications. Olive oils from 'Azeite da Beira Interior' and 'Azeite de Trás-os-Montes' showed greater total phenols contents and antioxidant capacities, while 'Azeites da Beira Interior' presented higher oxidative stabilities. Linear discriminant models were developed using FTIR spectra (transmittance and the 1 st and 2 nd derivatives), allowing the correct identification of the oils' PDO (100 % sensitivity and specificity, repeated K-fold-CV). This study also revealed that multiple linear regression models, based on FTIR transmittance data, could predict the sweet, bitter, and pungent intensities of the PDO oils (R 2 ≥0.979±0.016; RMSE≤0.26±0.05, repeated K-fold-CV). This demonstrates the potential of using FTIR as a non-destructive technique for authenticating oils with PDO., (© 2023 Wiley-VHCA AG, Zurich, Switzerland.)

Extra virgin olive oil phenolic compounds have been identified as possible biostimulant agents against different pathological processes, including alterations in healing processes. However, there is little evidence on the molecular mechanisms involved in this process. The aim was to analyse the effect of hydroxytyrosol, tyrosol, and oleocanthal on fibroblast gene expression. PCR was used to determine the expression of different differentiation markers, extracellular matrix elements, and growth factors in cultured human fibroblasts CCD-1064Sk treated with different doses of hydroxytyrosol (10 -5 M and 10 -6 M), tyrosol (10 -5 M and 10 -6 M), and oleocanthal (10 -6 M and 10 -7 M). After 24 h of hydroxytyrosol treatment, increased expression of connective tissue growth factor, fibroblast growth factor (FGF), platelet-derived growth factor, vascular endothelial growth factor, transforming growth factor β1 (TGF-β1), and their receptors was observed. Tyrosol and olecanthal modulated the expression of FGF and TGFβR1. All phytochemicals tested modified the expression of differentiation markers and extracellular matrix elements, increasing gene expression of actin, fibronectin, decorin, collagen I, and III. Phenolic compounds present in extra virgin olive could have a beneficial effect on tissue regeneration by modulating fibroblast physiology.

The chemistry of the phenolic compounds found in virgin olive oil (VOO) is very complex due, not only to the different classes of polyphenols that can be found in it, but, above all, due to the existence of a very specific phenol class found only in oleaceae plants: the secoiridoids. Searching in the Scopus data base the keywords flavonoid, phenolic acid, lignin and secoiridoid, we can find a number of 148174, 79435, 11326 and 1392 research articles respectively, showing how little is devote to the latter class of compounds. Moreover, in contrast with other classes, that include only phenolic compounds, secoiridoids may include phenolic and non-phenolic compounds, being the articles concerning phenolic secoiridoids much less than the half of the abovementioned articles. Therefore, it is important to clarify the structures of these compounds and their chemistry, as this knowledge will help understand their bioactivity and metabolism studies, usually performed by researchers with a more health science's related background. In this review, all the structures found in many research articles concerning VOO phenolic compounds chemistry and metabolism was gathered, with a special attention devoted to the secoiridoids, the main phenolic compound class found in olives, VOO and olive leaf.

Olive oil (OO) polyphenols have been shown to improve HDL anti-atherogenic function, thus demonstrating beneficial effects against cardiovascular risk factors. The aim of the present study was to investigate the effect of extra virgin high polyphenol olive oil (HPOO) v . low polyphenol olive oil (LPOO) on the capacity of HDL to promote cholesterol efflux in healthy adults. In a double-blind, randomised cross-over trial, fifty participants (aged 38·5 (sd 13·9) years, 66 % females) were supplemented with a daily dose (60 ml) of HPOO (320 mg/kg polyphenols) or LPOO (86 mg/kg polyphenols) for 3 weeks. Following a 2-week washout period, participants crossed over to the alternate treatment. Serum HDL-cholesterol efflux capacity, circulating lipids (i.e. total cholesterol, TAG, HDL, LDL) and anthropometrics were measured at baseline and follow-up. No significant between-group differences were observed. Furthermore, no significant changes in HDL-cholesterol efflux were found within either the LPOO and HPOO treatment arms; mean changes were 0·54 % (95 % CI (0·29, 1·37)) and 0·10 % (95 % CI (0·74, 0·94)), respectively. Serum HDL increased significantly after LPOO and HPOO intake by 0·13 mmol/l (95 % CI (0·04, 0·22)) and 0·10 mmol/l (95 % CI (0·02, 0·19)), respectively. A small but significant increase in LDL of 0·14 mmol/l (95 % CI (0·001, 0·28)) was observed following the HPOO intervention. Our results suggest that additional research is warranted to further understand the effect of OO with different phenolic content on mechanisms of cholesterol efflux via different pathways in multi-ethnic populations with diverse diets.

Extra virgin olive oil (EVOO) is largely used in Mediterranean diet, and it is also worldwide apprised not only for its organoleptic properties but also for its healthy effects mainly attributed to the presence of several naturally occurring phenolic and polyphenolic compounds (bio-phenols). These compounds are characterized by the presence of multiple phenolic groups in more or less complex structures. Their content is fundamental in defining the healthy qualities of EVOO and consequently the analytical methods for their characterization and quantification are of current interest. Traditionally their determination has been conducted using a colorimetric assay based on the reaction of Folin-Ciocalteu (FC) reagent with the functional hydroxy groups of phenolic compounds. Identification and quantification of the bio-phenols in olive oils requires certainly more performing analytical methods. Chromatographic separation is now commonly achieved by HPLC, coupled with spectrometric devices as UV, FID, and MS. This last approach constitutes an actual cutting-edge application for bio-phenol determination in complex matrices as olive oils, mostly on the light of the development of mass analyzers and the achievement of high resolution and accurate mass measurement in more affordable instrument configurations. After a short survey of some rugged techniques used for bio-phenols determination, in this review have been described the most recent mass spectrometry-based methods, adopted for the analysis of the bio-phenols in EVOOs. In particular, the sample handling and the results of HPLC coupled with low- and high-resolution MS and MS/MS analyzers, of ion mobility mass spectrometry and ambient mass spectrometry have been reported and discussed., (© 2021 The Authors. Mass Spectrometry Reviews published by John Wiley & Sons Ltd.)

The defense mechanism against harmful stimuli is inflammation. Indeed, neurodegenerative disorders can arise as a result of a persistent neuroinflammation. Beta-amyloid (Aβ 1-42 ) is an early trigger in the origination of Alzheimer's disease, leading to synaptic and cognitive impairments. Virgin olive oil (VOO) is correlated with a decreased risk of developing immune-inflammatory disorders, but the potential effects of the phenolic fraction (PF) from VOO in the modulation of neuroinflammatory processes in neutrophils remain unknown. In this study, we investigated the ability of the PF to modulate the activation of Aβ 1-42 -stimulated primary human neutrophils, focusing on the expression of gene and surface markers and the release of pro-inflammatory and chemoattractant mediators. Down-regulation of pro-inflammatory cytokine gene expression in Aβ 1-42 -treated neutrophils, among other changes, was reported. Furthermore, pretreatment with PF prevented neutrophil activation. The beneficial effects in the modulation of inflammatory responses show the relevance of VOO to achieve a healthier diet that can help prevent inflammatory diseases.

The European Food Safety Authority highlights the beneficial effects of olive oil phenols, mainly, secoiridoids. Nevertheless, the metabolism of secoiridoids in humans has not been fully elucidated. This research evaluated the metabolism of secoiridoids in humans after intake of olive oils with diverse phenolic profiles. For this purpose, three extra virgin olive oils (EVOOs) were ingested by six volunteers at scheduled meals, and urine samples were collected the following morning for subsequent LC-MS/MS analysis. Using untargeted analysis, urinary metabolites revealed representative patterns associated with the various olive oil phenolic contents in absolute and relative terms. We were able to identify metabolites obtained through phase I, phase II, and microbial metabolism with discrimination between tyrosol and hydroxytyrosol derivatives. Metabolism of phenols is differentially activated as a function of the olive oil secoiridoids content, and this proof-of-concept study shows how urinary metabolites represent olive oil phenolic content., (Copyright © 2022 Elsevier Ltd. All rights reserved.)

Maternal breast milk provides the newborn with passive immunity and stimulates the maturation of the infant immune system. The aim of the present study was to evaluate the vertical transmission of phenolic compounds and their metabolites to offspring in rats fed with extra virgin olive oil (EVOO) during pregnancy and lactation. For this purpose, plasma and lactic serum from dams and plasma from offspring were analyzed by LC-ESI-LTQ-Orbitrap-MS. Both enzymatic and microbial metabolites of hydroxytyrosol and tyrosol were detected in dam plasma and lactic serum. In addition, significant levels of phenolic compounds and their metabolites were found in offspring plasma. The concentration and number of hydroxytyrosol derivatives was higher than those of tyrosol and the microbial metabolites were found in the highest concentration. The observed vertical transmission of EVOO phenolic compounds, whose health benefits are widely reported, provides further support for the importance of the maternal diet during pregnancy and lactation., (Copyright © 2022 The Author(s). Published by Elsevier Ltd.. All rights reserved.)

Extra virgin olive oil (EVOO) was gelled with 10% monoglycerides, (MG), rice wax (RW), γ-oryzanol, and β-sitosterol (PS), or ethylcellulose (EC). The oleogel structure and the stability of bioactive compounds were investigated during storage up to 120 days at 20, 30, and 40 °C. All samples were self-standing but presented different structures. PS produced the firmest gel, whereas EC caused the lowest firmness and rheological values. Structural properties did not change during storage, except for EC oleogel. Structuring triggered a depletion in phenolic content and α-tocopherol, which was more pronounced when a higher temperature was required for oleogel preparation (MG ~ RW < PS < EC). However, during storage phenolics and α-tocopherol decreased following zero-order kinetics with a higher susceptibility in unstructured oil, suggesting in all cases a protective effect of the gel network., (Copyright © 2021 Elsevier Ltd. All rights reserved.)

The aim of this work was to recover phenolic compounds such as oleacein and oleocanthal from low commercial value olive oils destined for refining [lampante olive oil (LOO)]. For this, the ability of three extraction systems of phenols from oils was evaluated. A new quick and simple extraction method (NM) for obtaining phenols was developed, consisting of the acidified mixture MeOH/H 2 O (50:50) (v/v) 0.1% formic acid, and it was compared to a conventional method (CM) widely used for the analytical determination of phenolic compounds in olive oil using MeOH: H 2 O (80:20) (v/v). NM showed a higher yield for the extraction of oleacein with an increase of 14% compared to CM; no significant differences were observed in the extraction of oleocanthal between the two methods. The third method, using two formulations of deep eutectic solvents (DESs) based on ChCl, showed higher extractive efficiency for the two secoiridoids than CM and NM when DES consisted of ChCl and xylitol. On the other hand, the concentrations of oleacein and oleocanthal were determined in 14 samples of blended oils that were previously classified as extra virgin olive oil and LOO according to EU regulation. LOO contained amounts up to 109.89 and 140.16 mg/kg of oleacein and oleocanthal, respectively. Oleacein (>98%) and oleocanthal (>95%) were successfully recovered from phenolic extracts obtained from LOO oils through chromatographic separation and purification by semipreparative high-performance liquid chromatography. Therefore, these low-quality oils are an inexpensive source of bioactive substances.

The Mediterranean diet includes virgin olive oil (VOO) as the main fat and olives as snacks. In addition to providing nutritional and organoleptic properties, VOO and the fruits (olives) contain an extensive number of bioactive compounds, mainly phenolic compounds, which are considered to be powerful antioxidants. Furthermore, olive byproducts, such as olive leaves, olive pomace, and olive mill wastewater, considered also as rich sources of phenolic compounds, are now valorized due to being mainly applied in the pharmaceutical and nutraceutical industries. The digestive system must physically and chemically break down these ingested olive-related products to release their phenolic compounds, which will be further metabolized to be used by the human organism. The first purpose of this review is to provide an overview of the current status of in-vitro static digestion models for olive-related products. In this sense, the in-vitro gastrointestinal digestion methods are widely used with the following aims: (i) to study how phenolic compounds are released from their matrices and to identify structural changes of phenolic compounds after the digestion of olive fruits and oils and (ii) to support the functional value of olive leaves and byproducts generated in the olive industry by assessing their health properties before and after the gastrointestinal process. The second purpose of this review is to survey and discuss all the results available to date.

The INFOGEST standardized method was applied to assess the potential bioaccessibility and bioaccessibility of the phenolic compounds from a Galician extra-virgin olive oil (EVOO). The in vitro digestion model involves three steps and generates two fractions after each one: an aqueous fraction (namely, water phase (Wp)) and an oily fraction (namely, oily phase (Op)). The results showed that secoiridoids were the most abundant family in the Galician EVOO polar fraction, representing 98% of the total phenolic compounds. After oral digestion, phenolic acids and simple phenols were mainly detected in Wp, while lignans and flavonoids were mostly found in Op. After gastric digestion, extensive hydrolysis of secoiridoids was observed to generate free tyrosol, hydroxytyrosol, and hydroxytyrosol acetate. The instability of secoiridoids after intestinal digestion was again responsible for the release of simple phenols, which were mainly recovered in Wp together with flavonoids. In contrast, lignans were stable to duodenal conditions and remained in Op.

In the last few years, a new term, "High-phenolic olive oil", has appeared in scientific literature and in the market. However, there is no available definition of that term regarding the concentration limits of the phenolic ingredients of olive oil. For this purpose, we performed a large-scale screening and statistical evaluation of 5764 olive oil samples from Greece coming from >30 varieties for an eleven-year period with precisely measured phenolic content by qNMR. Although there is a large variation among the different cultivars, the mean concentration of total phenolic content was 483 mg/kg. The maximum concentration recorded in Greece reached 4003 mg/kg. We also observed a statistically significant correlation of the phenolic content with the harvest period and we also identified varieties affording olive oils with higher phenolic content. In addition, we performed a study of phenolic content loss during usual storage and we found an average loss of 46% in 12 months. We propose that the term high-phenolic should be used for olive oils with phenolic content > 500 mg/kg that will be able to retain the health claim limit (250 mg/kg) for at least 12 months after bottling. The term exceptionally high phenolic olive oil should be used for olive oil with phenolic content > 1200 mg/kg (top 5%).

The cultivar Bianchera is an autochthonous variety from the eastern part of northern Italy, but it is also cultivated in the Slovenian and Croatian peninsula of Istria where it is named Belica (Slovenia) and Bjelica (Croatia). The properties of oleocanthal, a natural anti-inflammatory ibuprofen-like compound found in commercial monocultivar extra virgin olive oils, were determined by means of both quantitative 1 H NMR ( q NMR) and HPLC analyses, where q NMR was identified as a rapid and reliable method for determining the oleocanthal content. The total phenolic content (TPC) was determined by means of the Folin-Ciocalteau method and the major phenols present in the olive oils were also quantified by means of HPLC analyses. All these analyses confirmed that the cultivar Bianchera was very rich in polyphenols and satisfied the health claim provided by the EU Commission Regulation on the polyphenols content of olive oils and their beneficial effects on human health.

The study was conducted to determine the effects of cultivar, harvest period and their interaction on the hydrophilic phenolic components extra virgin olive oils of the cultivars 'Ayvalık', 'Memecik' and 'Topakaşı'. Olives were collected at three different harvesting periods; (1) early harvest period-1 (Beginning of spotting), (2) early harvest period-2 (End of spotting), and (3) optimum harvest period. Oils were extracted using an abencor system. HPLC (High-performance liquid chromatograph) technique was used to quantify The phenolic compounds including: tyrosol (p-HPEA), hydroxytyrosol (3,4-DHPEA), luteolin, rutin, quercetin, catechin, sinapinic acid, p-coumaric acid, cinnamic acid, vanillin, vanillic acid, ferulic acid and gallic acid were quantified using HPLC. The results indicated that the effects of harvest period on the phenolic components were variety dependent. At the early harvest period-1, 'Memecik' and 'Topakaşı' had the highest efficiency in luteolin, cinnamic acid, vanillic acid, and ferulic acid contents, while 'Ayvalık' had the highest efficiency in hydroxytyrosol, sinapinic acid, p-coumaric, vanillin and ferulic acid contents. At the optimum harvest period, 'Ayvalık' had the highest efficiency in luteolin, tyrosol and gallic acid contents, while 'Topakaşı' had the highest efficiency in tyrosol, hydroxytyrosol and rutin content. The highest phenolic content was detected in the early harvest period-1. The content of tyrosol linearly increased with the progress of maturity harvest period, whereas the contents of the sinapinic acid, vanillin, vanilic acid and ferulic acid decreased. The oils of 'Memecik' variety had significantly higher phenolic content than those of 'Ayvalık' and 'Topakaşı' varieties.

Oleuropein, a glycosylated secoiridoid present in olive leaves, is known to be an important antioxidant phenolic compound. We studied the antioxidant effect of low doses of oleuropein aglycone (3,4-DHPEA-EA) and oleuropein aglycone peracetylated (3,4-DHPEA-EA(P)) in murine C2C12 myocytes treated with hydrogen peroxide (H 2 O 2 ). Both compounds were used at a concentration of 10 μM and were able to inhibit cell death induced by the H 2 O 2 treatment, with 3,4-DHPEA-EA(P) being more. Under our experimental conditions, H 2 O 2 efficiently induced the phosphorylated-active form of JNK and of its downstream target c-Jun. We demonstrated, by Western blot analysis, that 3,4-DHPEA-EA(P) was efficient in inhibiting the phospho-active form of JNK. This data suggests that the growth arrest and cell death of C2C12 proceeds via the JNK/c-Jun pathway. Moreover, we demonstrated that 3,4-DHPEA-EA(P) affects the myogenesis of C2C12 cells; because MyoD mRNA levels and the differentiation process are restored with 3,4-DHPEA-EA(P) after treatment. Overall, the results indicate that 3,4-DHPEA-EA(P) prevents ROS-mediated degenerative process by functioning as an efficient antioxidant.

The extra virgin olive oil (EVOO) dihydroxy-phenol oleacein is a natural inhibitor of multiple metabolic and epigenetic enzymes capable of suppressing the functional traits of cancer stem cells (CSC). Here, we used a natural product-inspired drug discovery approach to identify new compounds that phenotypically mimic the anti-CSC activity of oleacein. We coupled 3D quantitative structure-activity relationship-based virtual profiling with phenotypic analysis using 3D tumorsphere formation as a gold standard for assessing the presence of CSC. Among the top 20 computationally-predicted oleacein mimetics, four fulfilled the phenotypic endpoint of specifically suppressing the tumorsphere-initiating capacity of CSC, in the absence of significant cytotoxicity against differentiated cancer cells growing in 2D cultures in the same low micromolar concentration range. Of these, 3,4-dihydrophenetyl butyrate -a lipophilic ester conjugate of the hydroxytyrosol moiety of oleacein- and (E)-N -allyl-2-((5-nitrofuran-2-yl)methylene)hydrazinecarbothioamide) -an inhibitor of Trypanosoma cruzi triosephosphate isomerase- were also highly effective at significantly reducing the proportion of aldehyde dehydrogenase (ALDH)-positive CSC-like proliferating cells. Preservation of the mTOR/DNMT binding mode of oleacein was dispensable for suppression of the ALDH + -CSC functional phenotype in hydroxytyrosol-unrelated mimetics. The anti-CSC chemistry of complex EVOO phenols such as oleacein can be phenocopied through the use of mimetics capturing its physico-chemical properties.

The aim of this study was to determine the cognitive and behavioral effects of extra virgin olive oil total phenolic content (TPC) and Sideritis (SID) extracts in female mice, and identify the associated neurochemical changes in the hippocampus and the prefrontal cortex. All animals received intraperitoneal low or high doses of TPC, SID or vehicle treatment for 7 days and were subjected to the Open Field (OF), Novel Object Recognition (NOR) and Tail Suspension Test (TST). The prefrontal cortex and hippocampus were dissected for analysis of neurotransmitters and aminoacids with high performance liquid chromatography with electrochemical detection (HPLC-ED). Both TPC doses enhanced vertical activity and center entries in the OF, which could indicate an anxiolytic-like effect. In addition, TPC enhanced non-spatial working memory and, in high doses, exerted antidepressant effects. On the other hand, high SID doses remarkably decreased the animals' overall activity. Locomotor and exploratory activities were closely associated with cortical increases in serotonin turnover induced by both treatments. Cognitive performance was linked to glutamate level changes. Furthermore, TPC reduced cortical taurine levels, while SID reduced cortical aspartate levels. TPC seems to have promising cognitive, anxiolytic and antidepressant effects, whereas SID has sedative effects in high doses. Both extracts act in the brain, but their specific actions and properties merit further exploration.

There is extensive information of the beneficial effects of virgin olive oil (VOO), especially on cardiovascular diseases. Some VOO healthy properties have been attributed to their phenolic-compounds (PCs). The aim of this review is to present updated data on the effects of olive oil (OO) PCs on the gut microbiota, lipid metabolism, immune system, and obesity, as well as on the crosstalk among them. We summarize experiments and clinical trials which assessed the specific effects of the olive oil phenolic-compounds (OOPCs) without the synergy with OO-fats. Several studies have demonstrated that OOPC consumption increases Bacteroidetes and/or reduces the Firmicutes / Bacteroidetes ratio, which have both been related to atheroprotection. OOPCs also increase certain beneficial bacteria and gut-bacteria diversity which can be therapeutic for lipid-immune disorders and obesity. Furthermore, some of the mechanisms implicated in the crosstalk between OOPCs and these disorders include antimicrobial-activity, cholesterol microbial metabolism, and metabolites produced by bacteria. Specifically, OOPCs modulate short-chain fatty-acids produced by gut-microbiota, which can affect cholesterol metabolism and the immune system, and may play a role in weight gain through promoting satiety. Since data in humans are scarce, there is a necessity for more clinical trials designed to assess the specific role of the OOPCs in this crosstalk.

Phenolic compounds largely contribute to the nutraceutical properties of virgin olive oil (VOO), the organoleptic attributes and the shelf life due to their antioxidant capabilities. Due to the relevance of malaxation in the oil extraction process, we tested the effects of malaxation time on the concentrations of relevant phenolic compounds in VOO, and we evaluated the influence of performing malaxation under vacuum. An increase in malaxation time significantly decreased the concentrations of aglycone isomers of oleuropein and ligstroside but, conversely, increased the oleocanthal and oleacein contents. Additionally, malaxation under vacuum led to an increase in phenolic contents compared to standard conditions carried out at atmospheric pressure. Finally, we explored the possibility of predicting the VOO oxidative stability on the basis of the phenolic profile, and a model (R 2  = 0.923; p < 0.0001) was obtained by combining the concentration of the VOO phenolic compounds and the main fatty acids., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2020 Elsevier Ltd. All rights reserved.)

The phenolic fraction of the extra virgin olive oil (EVOO) has been studied over the past two decades because of its important health protective properties. Numerous studies have been performed in order to clarify the most crucial factors that affect the concentration of the EVOO's phenolic fraction and many contradictory results have been reported. Having as target to maximize the phenolic content of EVOO and its healthy properties we investigated the impact of harvest time, malaxation temperature, and malaxation duration on the concentration of individual phenols in extra virgin olive oil. Olive oil was prepared in a lab-scale olive mill from different varieties in Greece. The extraction process for cultivar (cv) Koroneiki samples was performed at five different harvest periods from the same trees with three different malaxation temperatures and five different malaxation duration times (N = 75). Similar types of experiments were also performed for other varieties: cv Athenolia (N = 20), cv Olympia (N = 3), cv Kalamata (N = 3), and cv Throubolia Aegean (N=3) in order to compare the changes in the phenolic profile during malaxation. The quantitative analysis of the olive oil samples with NMR showed that the total phenolic content has a negative correlation with the ripening degree and the malaxation time. The NMR data we collected helped us to quantitate not only the total phenolic content but also the concentration of the major phenolic compounds such as oleocanthal, oleacein, oleokoronal, and oleomissional. We noticed different trends for the concentration of these phenols during malaxation process and for different malaxation temperatures. The different trends of the concentration of the individual phenols during malaxation and the completely different behavior of each variety revealed possible biosynthetic formation steps for oleocanthal and oleacein and may explain the discrepancies reported from previous studies.

Reversed-phase liquid chromatography with electrospray ionization-high-resolution/accuracy Fourier transform mass spectrometry (RPC-ESI-FTMS) and chemometrics were exploited to evaluate the influence of horizontal centrifugation by two- or three-phase decanters on the content of major phenolic secoiridoids in extravirgin olive oils (EVOOs). Despite the occurrence of other potential sources of variability typical of commercial olive oils, horizontal centrifugation was found to play a primary role, with a general increase of secoiridoid content occurring when two-phase decanters were used. As emphasized by principal component analysis (PCA), the increase involved preferentially oleacin and oleocanthal, when oxidative deterioration was purposely minimized during and/or after production, and oleuropein and ligstroside aglycones, when no vertical centrifugation was performed at the end of the productive cycle. The influence of the type of horizontal centrifugation was also emphasized by the elaboration of RPC-ESI-FTMS data based on hierarchical cluster analysis (HCA) and linear discriminant analysis (LDA).

Olive mill wastewaters (OMWs) are important by-products of olive oil production. The wide availability and the forbidding economic costs of OMWs disposal have generated interest in their possible exploitation as a sustainable source of polyphenols. The development and optimisation of improved analytical methods for the detailed characterisation of polyphenol molecular profiles after production and during storage conditions are thus required. A new analytical method based on reverse-phase HPLC separation of polyphenols in OMWs on an embedded-polar group (EPG) stationary phase is proposed as an alternative to conventional C18 columns. The procedure was used for the quantitation of 11 polyphenols, using diode-array detection (DAD), and achieving quantitation limits equal to or lower than 0.1 µg g -1 . The same chromatographic set-up, coupled with high resolution tandem mass spectrometry (HPLC/ESI-Q-ToF), allowed us to identify hydroxytyrosyl esters of elenolic acid, whose relative abundance is proposed for monitoring the ageing of OMWs during storage.

Epidemiological studies have compellingly documented the ability of the Mediterranean diet rich in extra-virgin olive oil to reduce the incidence of certain malignancies, and cardiovascular diseases, and slow the Alzheimer's disease progression. S-(-)-Oleocanthal (OC) was identified as the most bioactive olive oil phenolic with documented anti-inflammatory, anticancer, and anti-Alzheimer's activities. OC consumption causes irritating sensation at the oropharynx via activation of TRPA1. Accordingly, a taste-masked formulation of OC is needed for its future use as a nutraceutical while maintaining its bioactivity and unique chemistry. Therefore, the goal of this study was to prepare a taste-masked OC solid formulation with improved dissolution and pharmacodynamic profiles, by using (+)-xylitol as an inert carrier. Xylitol was hypothesized to serve as an ideal vehicle for the preparation of OC solid dispersions due to its low melting point and sweetness. The optimized OC-(+)-xylitol solid dispersion was physically and chemically characterized and showed effective taste masking and enhanced dissolution properties. Furthermore, OC-(+)-xylitol solid dispersion maintained potent in vivo anti-breast cancer activity. It effectively suppressed the human triple negative breast cancer development, growth, and recurrence after primary tumor surgical excision in nude mice orthotopic xenograft models. Collectively, these results suggest the OC-(+)-xylitol solid dispersion formulation as a potential nutraceutical for effective control and prevention of human triple negative breast cancer., (Copyright © 2019 Elsevier B.V. All rights reserved.)

The health promoting effects of extra virgin olive oil (EVOO) relate to its unique repertoire of phenolic compounds. Here, we used a chemoinformatics approach to computationally identify endogenous ligands and assign putative biomolecular targets to oleacein, one of the most abundant secoiridoids in EVOO. Using a structure-based virtual profiling software tool and reference databases containing more than 9000 binding sites protein cavities, we identified 996 putative oleacein targets involving more than 700 proteins. We subsequently identified the high-level functions of oleacein in terms of biomolecular interactions, signaling pathways, and protein-protein interaction (PPI) networks. Delineation of the oleacein target landscape revealed that the most significant modules affected by oleacein were associated with metabolic processes (e.g., glucose and lipid metabolism) and chromatin-modifying enzymatic activities (i.e., histone post-translational modifications). We experimentally confirmed that, in a low-micromolar physiological range (<20 μmol/l), oleacein was capable of inhibiting the catalytic activities of predicted metabolic and epigenetic targets including nicotinamide N-methyltransferase, ATP-citrate lyase, lysine-specific demethylase 6A, and N-methyltransferase 4. Our computational de-orphanization of oleacein provides new mechanisms through which EVOO biophenols might operate as chemical prototypes capable of modulating the biologic machinery of healthy aging., (Copyright © 2019 Elsevier Ltd. All rights reserved.)

The objective of this study is the determination of the chemical structure of nine phenolic molecules responsible for the phytotoxic action on the germination of the plant species "Trigonella foenum-graecum". The phytotoxic action was evaluated by calculating the germination index of the plant species for a period of 5 days of incubation. The analysis of the physicochemical properties of phenolic molecules shows that hydrophobicity is a key factor in phytotoxicity. The sublethal concentration varies as follows: hydroquinone (0.91 mM), 4-aminophenol (0.85 mM), phenol (0.75 mM), gallic acid (0.59 mM), caffeic acid (0.56 mM), 3,5-di-tert-butylcatechol (0,45 mM), quercetin (0.33 mM), oleuropein (0.3 mM), and catechol (0.13 mM). Phytotoxicity varies depending on the nature and position of the substituents on the aromatic ring. The reactivity of this type of molecule is partly linked to the presence of catechol function that can play the main role in phytotoxicity of the Fenugreek.

Olive oil is not only known for its pungent, bitter, and fruity taste, but also for its health potential, which is often hypothesized to depend on its phenolic compounds. One hundred extra virgin olive oil samples (monocultivaric as well as blends of varieties) were assessed with regard to their sensory properties and phenolic compound composition. Nineteen phenolic compounds have been determined and correlated with sensory data. In all olive oil samples, oleocanthal and oleacein were the most abundant phenolic compounds, with average amounts of 77.9 mg/kg and 41.8 mg/kg, respectively. The highest correlation coefficient between a sensory descriptor and the phenolic compounds was found for the bitter taste sensation and the total phenolic content with r = 0.72 and in particular, for 3,4-DHPEA-EA, with r = 0.57. Intensity plots were assessed for the three main sensory descriptors fruitiness, bitterness, pungency, and for the quality factor harmony, which is associated with the degree of ripeness aroma of olive oil. Positive correlations for the aroma descriptors freshly cut grass, leaves, and nuts, and the phenolic compounds were especially observed for oleoside 11-methylester and vanillic acid. The present study provides a comprehensive database of phenolic compounds in olive oils from six different varieties and seven countries.

The current therapeutic scenario for inflammatory bowel diseases (IBD) involves aminosalicylates, corticosteroids, and immunomodulators, but concerns regarding their safety profiles and high costs heavily impact their widespread use. In recent years, the beneficial effects thatbiophenols-from fruit and vegetables-have on human health have been investigated. The antioxidant and anti-inflammatory properties of phenolic fraction, from olive leaves and fruits, have been suggested, and a potential application in gut inflammation has been supported by in vitro and IBD-animal models studies. In the present review, we first introduced the potential therapeutic role of olive tree biophenolsin chronic inflammatory disease. Then, we aimed to describe their most interesting application for gut inflammation, as the results of basic science studies and animal experimental models. Finally, the potential role of olive tree biophenols in the setting of human IBD is discussed.

A regular consumption of virgin olive oil (VOO) is associated with a reduced risk of cardiovascular disease. We aimed to assess whether the raw intake of an optimized VOO (OVOO, 490 ppm of phenolic compounds and 86 ppm of triterpenes), and a functional olive oil (FOO, 487 ppm of phenolic compounds and enriched with 389 ppm of triterpenes) supplementation (30 mL per day) during three weeks would provide additional health benefits to those produced by a standard VOO (124 ppm of phenolic compounds and 86 ppm of triterpenes) on oxidative and inflammatory biomarkers. Fifty-one healthy adults participated in a randomized, crossover, and controlled study. Urinary 8-hidroxy-2'-deoxyguanosine, plasma interleukin-8 (IL-8), and tumor necrosis factor α (TNF- α) concentrations were lower after the intervention with the FOO than after the OVOO ( p = 0.033, p = 0.011 and p = 0.020, respectively). In addition, IL-8 was lower after the intervention with FOO than after VOO intervention ( p = 0.002). This study provides a first level of evidence on the in vivo health benefits of olive oil triterpenes (oleanolic and maslinic acids) in healthy humans, decreasing DNA oxidation and plasma inflammatory biomarkers. The trial was registered in ClinicalTrials.gov ID: NCT02520739.

In this study we investigated the genotoxic potential of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, (PhIP); 2-amino-3-methyl-3H-imidazo[4,5-f]quinoline, (IQ); 2-amino-3,8-dimethyl-imidazo[4,5-f]quinoxaline, (MeIQx) and 2-amino-3,4,8-trimethyl-3H-imidazo[4,5-f]quinoxaline (DiMeIQx) on human freshly isolated peripheral blood mononuclear cells (PBMC) by the comet assay. The preventive ability of three different phenolic extracts derived from olive (O-PE), virgin olive oil (OO-PE) and olive leaf (OL-PE) on PhIP induced DNA damage was also investigated. PhIP and IQ induced a significant DNA damage at the lowest concentration tested (100 μM), while the genotoxic effect of MeIQx and DiMeIQx become apparent only in the presence of DNA repair inhibitors Cytosine b-D-arabinofuranoside and Hydroxyurea (AraC/HU). The inclusion of metabolic activation (S9-mix) in the culture medium increased the genotoxicity of all HCAs tested. All three phenolic extracts showed an evident DNA damage preventive activity in a very low concentration range (0.1-1.0 μM of phenols) which could be easily reached in human tissues "in vivo" under a regular intake of virgin olive oil. These data further support the observation that consumption of olive and virgin olive oil may prevent the initiation step of carcinogenesis. The leaf waste could be an economic and simple source of phenolic compounds to be used as food additives or supplements., (Copyright © 2018. Published by Elsevier Ltd.)

Although the anticancer properties of extra virgin olive oil (EVOO) extracts have been recognized, the role of single compounds in non-melanoma skin cancer is still unknown. The in vitro chemopreventive and anticancer action of EVOO extracts and oil-derived compounds in non-melanoma skin cancer models were evaluated on cutaneous squamous cell carcinoma cells and on immortalized human keratinocytes stimulated with epidermal growth factor. Preparation of EVOO extracts and isolation of single compounds was carried out by chromatographic methods. Antitumor activity was assessed by cell-based assays (cell viability, migration, clonogenicity, and spheroid formation) and apoptosis documented by internucleosomal DNA fragmentation. Finally, inhibition of key oncogenic signaling nodes involved in the progression from actinic keratosis to cutaneous squamous cell carcinoma was studied by western blot. EVOO extracts reduced non-melanoma skin cancer cell viability and migration, prevented colony and spheroid formation, and inhibited proliferation of atypical keratinocytes stimulated with epidermal growth factor. Such a pharmacological activity was promoted by oleocanthal and oleacein through the inhibition of Erk and Akt phosphorylation and the suppression of B-Raf expression, whereas tyrosol and hydroxytyrosol did not have effect. The current study provides in vitro evidence for new potential clinical applications of EVOO extracts and/or single oil-derived compounds in the prevention and treatment of non-melanoma skin cancers., (Copyright © 2018 Elsevier Ltd. All rights reserved.)

To investigate if the anecdotal varietal typicity concepts for two monovarietal virgin olive oils (VOO) can be scientifically supported and explained, VOO samples were sorted according to typicity grade and related to sensory and compositional data for volatiles and phenols. Clear inter-varietal, as well as intra-varietal boundaries between more and less typical samples were established by univariate and multivariate statistics. A variety-typical complex odor was related to a complex VOO volatile composition with relatively high amounts of lipoxygenase-derived compounds, accompanied by hydrocarbons, terpenes, and benzenoids. A simpler odor, described mostly as green and typical for the other monovarietal VOO, coincided with the lower amounts of the same volatiles. The intensity of bitterness and pungency was mostly in correlation with the amount of major phenols. Two monovarietal VOOs were clearly distinguished with respect to their variety-typical expression of pungency: the one described as gradually increasing was tentatively related to pinoresinol, while the other, described as immediately strong and burning, was assumed to originate mainly from p-HPEA-EDA. Intra-varietal typicity grades correlated with hedonic liking, as well as with general VOO positive sensory attributes related to key volatiles and phenols., (Copyright © 2018 Elsevier Ltd. All rights reserved.)

The broad number of health benefits which can be obtained from the long-term consumption of olive oil are attributed mainly to its phenolic fraction. Many olive oil phenolics have been studied deeply since their discovery due to their bioactivity properties, such as Hydroxytyrosol. Similarly, in the last decade, the special attention of researchers has been addressed to Oleocanthal (OC). This olive oil phenolic compound has recently emerged as a potential therapeutic agent against a variety of diseases, including cancer, inflammation, and neurodegenerative and cardiovascular diseases. Recently, different underlying mechanisms of OC against these diseases have been explored. This review summarizes the current literature on OC to date, and focuses on its promising bioactivities against different disease-targets.

The aim of the present work was to evaluate the phenolic profile of the 'Brava' extra virgin olive oil and assess its potential as a "natural adjuvant" in combination with chemotherapy treatment. The total phenol content of the phenolic extracts was 764 mg gallic acid equivalents/kg and the total antioxidant capacity was 2309, 1881 and 2088 μM trolox equivalents/kg determined by Diphenyl-1-picrylhydrazyl free radical method, Ferric Reducing Antioxidant Power and Trolox Equivalent Antioxidant Capacity assay, respectively. Secoiridoids comprised 83% of the total phenolic compounds. The main secoiridoid from oleuropein was the main isomer of oleuropein aglycone (74 mg/kg). The main secoiridoid from ligstroside was the main isomer of ligstroside aglycone (214 mg/kg). These phenolic extracts showed a significant decrease in cell viability on MCF-7 breast cancer cells in a dose and time dependent manner. 48 h-treatments with different concentrations of the extracts induced intracellular ROS generation and cell death., (Copyright © 2018 Elsevier Ltd. All rights reserved.)

Non-communicable diseases (NCDs) have become the largest contributor to worldwide morbidity and mortality. Among them, cancer and cardiovascular diseases (CVDs) are responsible for a 47% of worldwide mortality. In general, preventive approaches modifying lifestyle are more cost-effective than treatments after disease onset. In this sense, a healthy diet could help a range of NCDs, such as cancer and CVDs. Traditional Mediterranean Diet (MD) is associated by the low-prevalence of certain types of cancers and CVDs, where olive oil plays an important role. In fact, different epidemiological studies suggest that olive oil consumption prevents some cancers, as well as coronary heart diseases and stroke incidence and mortality. Historically, the beneficial health effects of virgin olive oil (VOO) intake were first attributed to the high concentration of monounsaturated fatty acids. Nowadays, many studies indicate that phenolic compounds contained in olive oil have positive effects on different biomarkers related to health. Among them, phenolic compounds would be partially responsible for health benefits. The present work aims to explore, in studies published during the last five years, the effects of the main phenolic compounds isolated from olive oil on different cancer or CVD aspects, in order to clarify which compounds have more potential to be used as nutraceuticals with preventive or even therapeutic properties., Competing Interests: The authors declare no conflicts of interest.

Crushing is a key step during olive oil extraction. Among commercial crushers, the hammer mill is the most widely used due to its robustness and high throughput. In the present work, the impact of hammer mill rotor speed on extraction yield and overall quality of super-high-density Arbosana olive oils were assessed in an industrial facility. Our results show that increasing the rotor speed from 2400rpm to 3600rpm led to a rise in oil yield of 1.2%, while conserving quality parameters. Sensory analysis showed more pungency with increased rotation speed, while others attributes were unaffected. Volatile compounds showed little variation with the differences in crusher speed; however, total phenols content, two relevant secoiridoids, and triterpenoids levels increased with rotor speed. Hammer mill rotor speed is a processing variable that can be tuned to increase the extraction efficiency and modulate the chemical composition of extra virgin olive oil., (Copyright © 2017 Elsevier Ltd. All rights reserved.)

Background and Objective: The preventive effects of olive oil against different diseases have been attributed to its high phenolic compound content. The objective of this study was to examine available scientific evidence on the beneficial effects against chronic diseases of olive oil phenolic compounds., Method: This article examines recently published data on olive oil phenolic compounds and their potential benefits in the prevention of cardiovascular disease, cancer, neurodegenerative disease, and osteoporosis., Results: The antioxidant, anti-proliferative, pro-apoptotic, and anti-inflammatory activities of olive oil phenolic compounds have preventive effects against heart disease and cancer. These compounds also exert neuroprotective and neuromodulator effects against neurodegenerative disease, inhibiting the development of amyloid plaques. Finally, they are known to protect against osteoporosis, favoring bone regeneration., Conclusion: Dietary intake of olive oil can be recommended by healthcare professionals as an important source of phenolic compounds that play a role in the prevention of chronic disease and the consequent improvement in quality of life., (Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.)

Neurological disorders such as stroke, Alzheimer's and Parkinson's diseases are associated with high morbidity and mortality, and few or no effective options are available for their treatment. These disorders share common pathological characteristics like the induction of oxidative stress, abnormal protein aggregation, perturbed Ca 2+ homeostasis, excitotoxicity, inflammation and apoptosis. A large body of evidence supports the beneficial effects of the Mediterranean diet in preventing neurodegeneration. As the Mediterranean diet is characterized by a high consumption of extra-virgin olive oil it has been hypothesized that olive oil, and in particular its phenols, could be responsible for the beneficial effect of the Mediterranean diet. This review provides an updated vision of the beneficial properties of olive oil and olive oil phenols in preventing/counteracting both acute and chronic neurodegenerative diseases., Competing Interests: The authors declare no conflict of interest.

Scope: Low paraoxonase (PON)1 activities, and high PON1 and low PON3 protein levels are characteristic of cardiovascular disease. Our aim was to assess short- and long-term effects of virgin olive oils (VOO), enriched with their own phenolic compounds (PC; FVOO) or with them plus complementary PC from thyme (FVOOT), on PON-related variables and the mechanisms involved., Methods and Results: Two randomized, controlled, double-blind, and crossover interventions were conducted. In an acute intake study, participants ingested three FVOOs differing in PC content. In a sustained intake study, participants ingested a control VOO and two different FVOOs with the same PC content but differing in PC source. Acute and sustained intake of VOO and FVOO decreased PON1 protein and increased PON1-associated specific activities, while FVOOT yielded opposite results. PON3 protein levels increased only after sustained consumption of VOO. Mechanistic studies performed in rat livers showed that intake of isolated PC from VOO and from thyme modulate mitogen-activated protein kinases and peroxisome proliferator-activated receptors regulating PON synthesis, while a combination of these PCs cancels such regulation., Conclusion: This study reveals that the intake of phenol-enriched FVOOs modulates oxidative balance by modifying PON-related variables according to PC content and source, and this modulation can be perceived as beneficial., (© 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

The interactive effects of ripening degree, malaxation duration and temperature on Oblica cv. (Olea europaea L.) virgin olive oil phenols, volatiles, and sensory quality were investigated. Olives were picked at three ripening degrees with International Olive Council indices of 0.68, 2.48 and 4.10, and processed by malaxation at 22 and 30°C, and at both temperatures for 30 and 60min. Ripening exhibited the strongest effect, and malaxation duration the weakest. Phenols were generally found to decrease during ripening; however 3,4-DHPEA-EDA and p-HPEA-EDA increased. Similar behaviour was observed for (E)-2-hexenal. Higher malaxation temperature induced an increase in particular important phenols and C6 alcohols, while C6 aldehydes mostly decreased. Interactions between the factors were established, mostly between ripening degree and malaxation temperature: the effect of the latter was most pronounced for ripe olives, especially for 3,4-DHPEA-EDA, p-HPEA-EDA and C6 volatiles. Sensory attributes were generally in agreement with the chemical composition., (Copyright © 2017 Elsevier Ltd. All rights reserved.)

Coronary artery disease (CAD) is responsible for more than 7 million deaths worldwide. In the early stages of the development of atherosclerotic plaques, cardiovascular risk factors stimulate vascular endothelial cells, initiating an inflammatory process, fundamental in the pathogenesis of CAD. The inclusion of potentially cardioprotective foods, such as olive oil, to the diet, may aid in the control of these risk factors, and in the reduction of cytokines and inflammatory markers. The present review aims to address the interaction between phenolic compounds present in olive oil, and inflammation, in the prevention and treatment of CAD. In vitro and in vivo studies suggest that phenolic compounds, such as hydroxytyrosol, tyrosol, and their secoiridoid derivatives, may reduce the expression of adhesion molecules and consequent migration of immune cells, modify the signaling cascade and the transcription network (blocking the signal and expression of the nuclear factor kappa B), inhibit the action of enzymes responsible for the production of eicosanoids, and consequently, decrease circulating levels of inflammatory markers. Daily consumption of olive oil seems to modulate cytokines and inflammatory markers related to CAD in individuals at risk for cardiovascular diseases. However, clinical studies that have evaluated the effects of olive oil and its phenolic compounds on individuals with CAD are still scarce.

A LC-MS method involving direct injection of extra-virgin olive oil (EVOO) - after a simple dilution - for determining its phenolic compounds has been developed. Optimization of the most appropriate solvent for sample dilution, selection of the optimum oil/solvent ratio, and establishment of column cleaning strategy and maximum number of injections were some of the most relevant steps. Then, the analytical parameters of the method were evaluated, establishing LOD (from 3.3 to 31.6µg/L) and LOQ, precision (RSD values for inter-day repeatability were found between 3.49 and 6.12%), and trueness (within the range 89.9-102.3% for 1.0mg/L) and checking possible matrix effect (which was no significant). Three kinds of calibration were used: external standard, standard addition and calibration in a phenols-free matrix, which was subsequently applied to quantify the phenolic compounds in 16 EVOOs (from 6 cultivars). A total of 21 compounds were determined without the need of using any extraction protocol., (Copyright © 2017 Elsevier Ltd. All rights reserved.)

Scope: Systemic lupus erythematosus (SLE) is a chronic multiorgan autoimmune disease characterized by immune deregulation, which involves altered T-cell response and imbalance of cytokine production. The phenolic fraction (PE) of extra virgin olive oil (EVOO) possesses anti-inflammatory and immunomodulatory properties and exerts preventive effects in murine models of immune-inflammatory diseases, such as SLE. The present study was designed to determine the in vitro effects of the PE from EVOO on peripheral blood mononuclear cells (PBMC) from inactive patients with SLE and healthy donors., Methods and Results: T-cell phenotype was investigated by flow cytometry, cytokine levels were determined by ELISA, and protein expression was detected by Western blot. The PE of EVOO decreased the frequency of CD69 + cells and the secretion of IFN-γ, TNF-α, IL-6, IL-1β, and IL-10. Moreover, PE increased the expression of I-kappa-B-α and decreased extracellular signal regulated kinase phosphorylation on PBMC from patients with SLE and healthy donors., Conclusion: PE modulates cytokine production and attenuates induced T-cell activation, probably through NF-κB signaling pathway, providing the first evidence that PE from EVOO has an anti-inflammatory and immunomodulatory role in SLE patients and it might therefore be considered as a dietary complement in SLE management., (© 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

The use of bisphenol A (BPA) in packaging has grown over the past 50 years despite concerns of its migration into packaged food and beverages, resulting in human exposure. Many studies have reported tumorigenic effects and endocrine alterations associated with BPA in animal models. This study aims at assessing human exposure to BPA from olive oil. A total of 27 olive oil samples were collected from mills and local villagers in the Hasbaya District, a major olive oil harvesting region in Lebanon. Information on storage conditions was also collected. BPA was extracted and quantified by HPLC. Results showed significantly higher BPA levels in olive oil samples stored in plastic vs. non-plastic packaging (mean = 333 vs. 150 μg/kg, p value = 0.006), samples with a plastic storage duration of >1 year compared to those with a storage duration of <1 year (mean = 452 vs. 288 μg/kg, p value = 0.008), and oil samples sourced from locals compared to oil mills (mean = 376 vs. 228 μg/kg, p value = 0.022). Statistically significant higher BPA levels remained for samples stored in plastic vs. non-plastic packaging in the bootstrap multivariable linear regression (B = 121.56, 95% CI 53.44-194.39, p value = 0.009). This is the first report on BPA levels in Mediterranean olive oil. The estimated exposure was 1.38% of the EFSA tolerable daily intake, hence there are no concerns about potential health risks from olive oil consumption.

A novel dynamic method for the investigation of the phenols activity in early stage oxidation of edible oils based on the formation of α-tocopheryl radicals initiated by oil-soluble vanadium complexes is developed. Two new vanadium complexes in oxidation states V and IV were synthesized by reacting 2,2'-((2-hydroxyoctadecyl)azanediyl)bis(ethan-1-ol) (C18DEA) with [VO(acac) 2 ] and 1-(bis(pyridin-2-ylmethyl)amino)octadecan-2-ol (C18DPA) with VOCl 2 . Addition of a solution of either complex in edible oils resulted in the formation of α-tocopheryl radical, which was monitored by electron paramagnetic resonance (EPR) spectroscopy. The intensity of the α-tocopheryl signal in the EPR spectra was measured versus time. It was found that the profile of the intensity of the α-tocopheryl signal versus time depends on the type of oil, the phenolic content, and the storage time of the oil. The time interval until the occurrence of maximum peak intensity be reached (t m ), the height of the maximum intensity, and the rate of the quenching of the α-tocopheryl radical were used for the investigation of the mechanism of the edible oils oxidation. 19 F NMR of the 19 F labeled phenolic compounds (through trifluoroacetate esters) and radical trap experiments showed that the vanadium complexes in edible oil activate the one electron reduction of dioxygen to superperoxide radical. Superperoxide reacts with the lipids to form alkoperoxyl and alkoxyl lipid radicals, and all these radicals react with the phenols contained in oils.