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Phenolic compounds from virgin olive oil obtained by natural deep eutectic solvent (NADES): effect of the extraction and recovery conditions.

ABSTRACT: Environmentally friendly natural deep eutectic solvents (NADES) have been shown to efficiently extract a wide range of phenolic compounds from virgin olive oil (VOO). The objective of this work was to optimize the yield of olive oil phenols extracted by NADES based on xylitol/choline choride (Xyl/ChCl). Different extraction and recovery conditions were investigated, including the effect of different extraction operating parameters (temperature, time, VOO:NADES ratio) and subsequent recovery conditions (XAD resin height, wash-water and eluent volume and pH). The highest concentration of phenols (555.36 mg/kg VOO) was obtained from extraction at 40 °C for 1 h, with a 1:1 ratio, using an adsorption resin XAD-16 with bed height of 10 cm, 250 mL acidified wash-water and 300 mL EtOH 100% as eluent. No statistically significant loss of the sum of phenolic compounds was observed when compared with the concentration values obtained by direct analysis in HPLC without the elimination of NADES. Additionally, a sequential desorption with different concentration of ethanol was used to determine the effect of the solvent concentration on polyphenol yield. Polar compounds, such as hydroxytyrosol and tyrosol, were recovered at 81.7% and 83.6%, respectively with 50 and 80% ethanol; however, 100% ethanol was required for the complete elution of oleacein (3,4-DHPEA-EDA) and oleocanthal (p-HPEA-EDA). In this paper we present an effective process for the extraction of polyphenols from VOO by NADES for direct analysis in HPLC and for the recovery and concentration of polyphenols by removing the solvent (NADES) with no losses of yield and solvent recycling.

SUBMITTER: Rodriguez-Juan E

PROVIDER: S-EPMC7847883 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Extraction of phenolic compounds from extra virgin olive oil by a natural deep eutectic solvent: Data on UV absorption of the extracts.

Project description:This data article refers to the paper "Towards green analysis of virgin olive oil phenolic compounds: extraction by a natural deep eutectic solvent and direct spectrophotometric detection" [1]. A deep eutectic solvent (DES) based on lactic acid and glucose was used as green solvent for phenolic compounds. Eight standard phenolic compounds were solubilized in the DES. Then, a set of extra virgin olive oil (EVOO) samples (n=65) were submitted to liquid-liquid extraction by the DES. The standard solutions and the extracts were analyzed by UV spectrophotometry. This article reports the spectral data of both the standard solutions and the 65 extracts, as well as the total phenolic content of the corresponding oils, assessed by the Folin-Ciocalteu assay.

| S-EPMC4961719 | biostudies-literature

Natural Deep Eutectic Solvent as Extraction Media for the Main Phenolic Compounds from Olive Oil Processing Wastes.

Project description:In this new century, sustainable development challenges chemical sciences to develop new and clean technological processes. The agri-food industry produces significant quantities of waste, raising significant economic and environmental concerns. Food waste valorization using environmentally friendly procedures is of increasing importance. This study describes the use of several Natural Deep Eutectic Solvents (NADESs) for the microwave-assisted extraction (MAE) of valuable bioactive phenolic compounds from olive oil processing wastes. The extracted samples were characterized by liquid chromatography electrospray ionization quadrupole time-of-flight mass spectrometry (LC-ESI-QTOF/MS) analysis and the quantification of the phenolic compounds was performed by HPLC analysis. The obtained data were compared with those obtained using water as the solvent in the same extraction conditions. The extraction process is nontoxic, simple and selective and meets most of the criteria to be considered as a sustainable process, with the solvents arising directly from nature.

| S-EPMC7346206 | biostudies-literature

Antique Traditional Practice: Phenolic Profile of Virgin Olive Oil Obtained from Fruits Stored in Seawater.

Project description:Virgin olive oil (VOO) is a functional food specific to the Mediterranean diet and related to human health, especially as a protector of cardiovascular health, in the prevention of several types of cancers, and in modification of immune and inflammatory response. Phenolic compounds have central importance for these extraordinary health benefits. In the production of high-quality olive oils, it is very important to process freshly picked olives and avoid any storage of fruits. However, in Croatia there is a very traditional and environmentally friendly method of olive oil production, where olive fruits are stored in seawater for some time prior to processing. This practice is also notable nowadays since there are people who prefer the characteristic flavor of the "seawater olive oil", although some people argue against its quality and biomedical relevance. In this study, the phenolic contents of VOO prepared from the immediately processed fresh olives and olives processed after storage in seawater were compared with the use of high-performance liquid chromatography-mass spectrometry (HPLC-MS) and spectrophotometric analysis. The results suggest that "seawater olive oil" should be considered as a safe food of biomedical relevance, as it still contains a significant proportion of important phenolics like hydroxytyrosol, tyrosol and oleacein (e.g., 63.2% of total phenols in comparison to VOO).

| S-EPMC7598162 | biostudies-literature

An Oleuropein ?-Glucosidase from Olive Fruit Is Involved in Determining the Phenolic Composition of Virgin Olive Oil.

Project description:Phenolic composition of virgin olive oil is determined by the enzymatic and/or chemical reactions that take place during olive fruit processing. Of these enzymes, ?-glucosidase activity plays a relevant role in the transformation of the phenolic glycosides present in the olive fruit, generating different secoiridoid derivatives. The main goal of the present study was to characterize olive fruit ?-glucosidase genes and enzymes responsible for the phenolic composition of virgin olive oil. To achieve that, we have isolated an olive ?-glucosidase gene from cultivar Picual (OepGLU), expressed in Nicotiana benthamiana leaves and purified its corresponding recombinant enzyme. Western blot analysis showed that recombinant OepGLU protein is detected by an antibody raised against the purified native olive mesocarp ?-glucosidase enzyme, and exhibits a deduced molecular mass of 65.0 kDa. The recombinant OepGLU enzyme showed activity on the major olive phenolic glycosides, with the highest levels with respect to oleuropein, followed by ligstroside and demethyloleuropein. In addition, expression analysis showed that olive GLU transcript level in olive fruit is spatially and temporally regulated in a cultivar-dependent manner. Furthermore, temperature, light and water regime regulate olive GLU gene expression in olive fruit mesocarp. All these data are consistent with the involvement of OepGLU enzyme in the formation of the major phenolic compounds present in virgin olive oil.

| S-EPMC5682033 | biostudies-literature

Nutri-Epigenetic Effects of Phenolic Compounds from Extra Virgin Olive Oil: A Systematic Review.

Project description:Dietary components can induce epigenetic changes through DNA methylation, histone modification, and regulation of microRNAs (miRNAs). Studies of diet-induced epigenetic regulation can inform anticipatory trials and fine-tune public health guidelines. We systematically reviewed data on the effect of extra virgin olive oil (EVOO) and its phenolic compounds (OOPCs) on the epigenetic landscape. We conducted a literature search using PubMed, Scopus, and Web of Science databases and scrutinized published evidence. After applying selection criteria (e.g., inclusion of in vitro, animal, or human studies supplemented with EVOO or its OOPCs), we thoroughly reviewed 51 articles, and the quality assessment was performed using the revised Cochrane risk of bias tool. The results show that both EVOO and its OOPCs can promote epigenetic changes capable of regulating the expression of genes and molecular targets involved in different metabolic processes. For example, oleuropein (OL) may be an epigenetic regulator in cancer, and hydroxytyrosol (HT) modulates the expression of miRNAs involved in the development of cancer, cardiovascular, and neurodegenerative diseases. We conclude that EVOO and its OOPCs can regulate gene expression by modifying epigenetic mechanisms that impact human pathophysiology. A full elucidation of the epigenetic effects of EVOO and its OOPCs may contribute to developing different pharma-nutritional strategies that exploit them as epigenetic agents. This study was registered in the International Prospective Register of Systematic Reviews (PROSPERO) as CRD42022320316.

| S-EPMC9526845 | biostudies-literature

Extra Virgin Olive Oil Contains a Phenolic Inhibitor of the Histone Demethylase LSD1/KDM1A.

Project description:The lysine-specific histone demethylase 1A (LSD1) also known as lysine (K)-specific demethylase 1A (KDM1A) is a central epigenetic regulator of metabolic reprogramming in obesity-associated diseases, neurological disorders, and cancer. Here, we evaluated the ability of oleacein, a biophenol secoiridoid naturally present in extra virgin olive oil (EVOO), to target LSD1. Molecular docking and dynamic simulation approaches revealed that oleacein could target the binding site of the LSD1 cofactor flavin adenosine dinucleotide with high affinity and at low concentrations. At higher concentrations, oleacein was predicted to target the interaction of LSD1 with histone H3 and the LSD1 co-repressor (RCOR1/CoREST), likely disturbing the anchorage of LSD1 to chromatin. AlphaScreen-based in vitro assays confirmed the ability of oleacein to act as a direct inhibitor of recombinant LSD1, with an IC50 as low as 2.5 μmol/L. Further, oleacein fully suppressed the expression of the transcription factor SOX2 (SEX determining Region Y-box 2) in cancer stem-like and induced pluripotent stem (iPS) cells, which specifically occurs under the control of an LSD1-targeted distal enhancer. Conversely, oleacein failed to modify ectopic SOX2 overexpression driven by a constitutive promoter. Overall, our findings provide the first evidence that EVOO contains a naturally occurring phenolic inhibitor of LSD1, and support the use of oleacein as a template to design new secoiridoid-based LSD1 inhibitors.

| S-EPMC6683035 | biostudies-literature

Proteomics of extra virgin olive oil (EVOO)

Project description:Proteins and peptides are minor components of vegetal oils. The presence of these compounds in virgin olive oil was first reported in 2001, but the nature of the olive oil proteome is still a puzzling question for food science researchers. In this project, we have compiled for a first time a comprehensive proteomic dataset of olive fruit and fungal proteins that are present at low but measurable concentrations in a vegetable oil from a crop of great agronomical relevance as olive (Olea europaea L.). Accurate mass nLC-MS data were collected in high definition direct data analysis (HD-DDA) mode using the ion mobility separation step. Protein identification was performed using the Mascot Server v2.2.07 software (Matrix Science) against an ad hoc database made of olive protein entries. Starting from this proteomic record, the impact of these proteins on olive oil stability and quality could be tested. Moreover, the effect of olive oil proteins on human health and their potential use as functional food components could be also evaluated. In addition, this dataset provides a resource for use in further functional comparisons across other vegetable oils, and also expands the proteomic resources to non-model species, thus also allowing further comparative inter-species studies.

2020-09-29 | PXD019894 | Pride

Structure-Biological Activity Relationships of Extra-Virgin Olive Oil Phenolic Compounds: Health Properties and Bioavailability.

Project description:Extra-virgin olive oil is regarded as functional food since epidemiological studies and multidisciplinary research have reported convincing evidence that its intake affects beneficially one or more target functions in the body, improves health, and reduces the risk of disease. Its health properties have been related to the major and minor fractions of extra-virgin olive oil. Among olive oil chemical composition, the phenolic fraction has received considerable attention due to its bioactivity in different chronic diseases. The bioactivity of the phenolic compounds could be related to different properties such as antioxidant and anti-inflammatory, although the molecular mechanism of these compounds in relation to many diseases could have different cellular targets. The aim of this review is focused on the extra-virgin olive oil phenolic fraction with particular emphasis on (a) biosynthesis, chemical structure, and influence factors on the final extra-virgin olive oil phenolic composition; (b) structure-antioxidant activity relationships and other molecular mechanisms in relation to many diseases; (c) bioavailability and controlled delivery strategies; (d) alternative sources of olive biophenols. To achieve this goal, a comprehensive review was developed, with particular emphasis on in vitro and in vivo assays as well as clinical trials. This report provides an overview of extra-virgin olive oil phenolic compounds as a tool for functional food, nutraceutical, and pharmaceutical applications.

| S-EPMC7464770 | biostudies-literature

Bone Protective Effect of Extra-Virgin Olive Oil Phenolic Compounds by Modulating Osteoblast Gene Expression.

Project description:The phenolic compounds of extra-virgin olive oil can act at various levels to protect individuals against cardiovascular and neurodegenerative diseases, cancer, and osteoporosis, among others. Polyphenols in extra-virgin olive oil can stimulate the proliferation of osteoblasts, modify their antigen profile, and promote alkaline phosphatase synthesis. The objective of this work was to determine the effect of different extra-virgin olive oil phenolic compounds on the gene expression of osteoblast-related markers. The cells of the MG63 osteoblast line were cultured for 24 h with 10-6 M of the phenolic compounds ferulic acid, caffeic acid, coumaric acid, apigenin, or luteolin. The expression of studied markers was quantified using quantitative real-time polymerase chain reaction (q-RT-PCR). The expression by MG63 osteoblasts of growth and differentiation/maturation markers was modified after 24 h of treatment with 10-6 M of the phenolic compounds under study, most of which increased the gene expression of the transforming growth factor ?1 (TGF-?1), TGF-? receptor 1,2 and 3 (TGF-?R1, TGF-?R2, TGF-?R3), bone morphogenetic protein 2 and 7 (BMP2, BMP7), run-related transcription factor 2 (RUNX-2), Alkaline phosphatase (ALP), Osteocalcin (OSC), Osterix (OSX), Collagen type I (Col-I) and osteoprotegerin (OPN). The extra-virgin olive oil phenolic compounds may have a beneficial effect on bone by modulating osteoblast physiology, which would support their protective effect against bone pathologies.

| S-EPMC6722737 | biostudies-literature

Effect of phenolic extracts from different extra-virgin olive oil varieties on osteoblast-like cells.

Project description:The reported incidence of osteoporosis is lower in countries in which the Mediterranean diet predominates, and this apparent relationship may be mediated by the phenolic compounds present in olive oil. The objective of this study was to determine the effect of phenolic extracts from different varieties of extra-virgin olive oil (Picual, Arbequina, Picudo, and Hojiblanca) on the differentiation, antigenic expression, and phagocytic capacity of osteoblast-like MG-63 cells. At 24 h of treatment a significant increase in phosphatase alkaline activity and significant reductions in CD54, CD80, and HLA-DR expression and in phagocytic activity were observed in comparison to untreated controls. The in vitro study performed has demonstrated that phenolic compounds from different extra virgin olive oil varieties can modulate different parameters related to osteoblast differentiation and function.

| S-EPMC5919649 | biostudies-literature

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