Oleuropein Aglycone

Antioxidant and anti-ageing effects of oleuropein aglycone in canine skeletal muscle cells.[Pubmed:38555794]

Tissue Cell. 2024 Mar 29;88:102369.

Reactive oxygen species (ROS) are normally produced in skeletal muscle. However, an imbalance in their regulatory systems can lead to their accumulation and ultimately to oxidative stress, which is one of the causes of the ageing process. Companion dogs share the same environment and lifestyle as humans, making them an excellent comparative model for the study of ageing, as well as they constitute a growing market for bioactive molecules that improve the quality of life of pets. The anti-ageing properties of Oleuropein Aglycone (OLE), a bioactive compound from olive leaves known for its antioxidant properties, were investigated in Myok9 canine muscle cell model. After incubation with OLE, senescence was induced in the canine cellular model by hydrogen peroxide (H(2)O(2)). Analyses were performed on cells after seven days of differentiation. The oxidative stress induced by H(2)O(2) treatment on differentiated canine muscle cells led to a significant increase in ROS formation, which was reduced by OLE pretreatment alone or in combination with H(2)O(2) by about 34% and 32%, respectively. Cells treated with H(2)O(2) showed a 48% increase the area of senescent cells stained by SA-beta-gal, while OLE significantly reduced the coloured area by 52%. OLE, alone or in combination with H(2)O(2), showed a significant antioxidant activity, possibly through autophagy activation, as indicated by the expression of autophagic markers.

Storage Effects on Bioactive Phenols in Calabrian Monovarietal Extra Virgin Olive Oils Based on the EFSA Health Claim.[Pubmed:37893692]

Foods. 2023 Oct 17;12(20):3799.

The beneficial properties of extra virgin olive oil (EVOO) on lipids blood levels were recognized by the European Food Safety Authority (EFSA) with a health claim, specifically referring to EVOOs containing at least 5 mg of hydroxytyrosol and its secoiridoids derivatives per 20 g of oil. The main purpose of the work was to characterize the phenolic profile of two commercially available Calabrian monovarietal EVOOs (Nocellara del Belice, VN; Dolce di Rossano, VDR), and to study the effect of one-year storage on secoiridoids composition, by monthly controls. A new UHPLC-ESI-HRMS method was developed and validated, thus facilitating the EFSA claim application and allowing producers to valorize their products. Seven biologically active compounds were chosen: tyrosol, hydroxytyrosol, oleocanthal, oleacein, Oleuropein Aglycone, verbascoside, and oleuropein. LODs and LOQs were 0.001-0.02 mg g(-1) and 0.002-0.08 mg g(-1), respectively. The variation coefficients were

The Protective Role of Oleuropein Aglycone against Pesticide-Induced Toxicity in a Human Keratinocytes Cell Model.[Pubmed:37834001]

Int J Mol Sci. 2023 Sep 26;24(19):14553.

The extensive use of agricultural pesticides to improve crop quality and yield significantly increased the risk to the public of exposure to small but repeated doses of pesticides over time through various routes, including skin, by increasing the risk of disease outbreaks. Although much work was conducted to reduce the use of pesticides in agriculture, little attention was paid to prevention, which could reduce the toxicity of pesticide exposure by reducing its impact on human health. Extra virgin olive oil (EVOO), a major component of the Mediterranean diet, exerts numerous health-promoting properties, many of which are attributed to Oleuropein Aglycone (OleA), the deglycosylated form of oleuropein, which is the main polyphenolic component of EVOO. In this work, three pesticides with different physicochemical and biological properties, namely oxadiazon (OXA), imidacloprid (IMID), and glyphosate (GLYPHO), were compared in terms of metabolic activity, mitochondrial function and epigenetic modulation in an in vitro cellular model of human HaCaT keratinocytes to mimic the pathway of dermal exposure. The potential protective effect of OleA against pesticide-induced cellular toxicity was then evaluated in a cell pre-treatment condition. This study showed that sub-lethal doses of OXA and IMID reduced the metabolic activity and mitochondrial functionality of HaCaT cells by inducing oxidative stress and altering intracellular calcium flux and caused epigenetic modification by reducing histone acetylation H3 and H4. GLYPHO, on the other hand, showed no evidence of cellular toxicity at the doses tested. Pretreatment of cells with OleA was able to protect cells from the damaging effects of the pesticides OXA and IMID by maintaining metabolic activity and mitochondrial function at a controlled level and preventing acetylation reduction, particularly of histone H3. In conclusion, the bioactive properties of OleA reported here could be of great pharmaceutical and health interest, as they could be further studied to design new formulations for the prevention of toxicity from exposure to pesticide use.

Maturity impact on physicochemical composition and polyphenol properties of extra virgin olive oils obtained from Manzanilla, Arbequina, and Koroneiki varieties in Iran.[Pubmed:37701214]

Food Sci Nutr. 2023 Jun 16;11(9):5396-5408.

This study investigated the physicochemical properties and polyphenol composition of extra virgin olive oils (EVOOs) extracted from three olive cultivars. The investigated cultivars were Arbequina, Koroneiki, and Manzanilla, grown in Olive Research Station in Rudbar county, Gilan province, Iran, at three ripening stages. Several parameters were analyzed, including peroxide and acidity values, unsaponifiable matter, oxidative stability, total aliphatic alcohols, fatty acids (FAs), sterols, and triacylglycerol composition. The results showed that as maturity increased, parameters such as oil content, acidity value, and iodine value, rise, while parameters including peroxide value, oxidative stability, aliphatic alcohols, and unsaponifiable matter decreased (p < .05). The saponification value was slightly reduced in the developing ripening process (p > .05). The MUFA/PUFA ratio and total sterol content declined during the olive ripening stages (p < .05). The triterpenes decreased in Arbequina and Koroneiki cultivars but increased in Manzanilla cultivar during the maturity stages. According to the data, oleuropein decreased while Oleuropein Aglycone, oxidized aldehyde, and hydroxylic form of oleuropein increased for all EVOOs during maturation. Apigenin, quercetin, ligstroside aglycone, aldehyde and hydroxylic form, ferulic acid, caffeic acid, and catechin decreased during the ripening of fruits (p < .05). The main triglycerides were triolein (OOO), palmitodiolein (POO), dioleolinolein (OOL), and palmitooleolinolein (PLO) in all EVOOs. In addition, the olive cultivar and harvesting date influence the physicochemical properties and polyphenol composition of EVOOs extracted from olive varieties grown in one region. In conclusion, the results can present helpful information to determine the optimum maturity stage for the investigated olive cultivars.

Targeted metabolic profiling of the revived ancient 'Corbella' olive cultivar during early maturation.[Pubmed:37527576]

Food Chem. 2024 Jan 1;430:137024.

'Corbella' is an ancient olive cultivar whose cultivation has recently been revived and hence little is known about its composition. This is the first work studying the metabolic profile of 'Corbella' olives during early maturation. Olives with a ripening index (RI) < 1 yielded considerably less oil content (<40%) but had more concentration of phenolic compounds (148.41-219.70 mg/kg), carotenoids (9.61-14.94 mg/kg) and squalene (521.41-624.40 mg/kg). Contrarily, the levels of alpha-tocopherol were higher at the RI of 1.08 and 1.96 (64.57 and 57.75 mg/kg, respectively). The most abundant phenolic compound was Oleuropein Aglycone (>50% of the phenolic composition), suggesting a high hydrolytic activity of beta-glucosidase in the fruit. The antioxidant capacity was barely affected, while oleic/linoleic ratio reached its highest at RI of 1.96. Therefore, olives with an RI below 2 could be good candidates to produce high-quality olive oils with good level of stability.

EVOO Polyphenols Exert Anti-Inflammatory Effects on the Microglia Cell through TREM2 Signaling Pathway.[Pubmed:37513845]

Pharmaceuticals (Basel). 2023 Jun 27;16(7):933.

In Alzheimer's disease (AD), microglia, brain resident immune cells, become chronically inflammatory and neurotoxic. In recent years, neuroinflammation has attracted particular interest in the scientific community. The genetic variants of molecules associated with ''microgliopathies'', including the triggering receptor expressed in myeloid cells-2 (TREM2), result in increased risk of developing AD and cognitive decline. We performed a set of in vitro assays using human neuronal (SH-SY5Y) and microglial (BV2 and C13NJ) cell models. Cells were differentially treated with extra virgin olive oil (EVOO) polyphenols, Oleuropein Aglycone (OleA) and hydroxytyrosol (HT) before adding LPS. We evaluated the protective effects of these EVOO products by a set of biochemical and cell biology assays, including ELISA, MTT, ROS detection, Western blotting and immunofluorescence. Our results provide an integrated understanding of the neuroprotection exerted by polyphenols in terms of: (i) reduction of pro-inflammatory cytokines release (IL-6, IL-8, IP-10 and RANTES); (ii) activation of the TREM2-dependent anti-inflammatory pathway; (iii) enhancement of protective microglial activity favoring the M2 polarization phenotype. Such findings provide new and important insights into the mechanisms by which the dietary olive polyphenols exert beneficial properties against neuroinflammation and neuronal impairment.

Comparison of Drying Techniques for Extraction of Bioactive Compounds from Olive-Tree Materials.[Pubmed:37509775]

Foods. 2023 Jul 12;12(14):2684.

Olive tree vegetal materials are considered a powerful source for the isolation of bioactive compounds-mainly phenols and triterpenic acids. However, the high humidity content of them reduces their preservation and extractability to a liquid solvent. Accordingly, a drying step is crucial to homogenize the material and to obtain an efficient extraction. We studied the influence of the drying process on the extraction efficiency of bioactive compounds from olive vegetal material. For this purpose, we evaluated the effects of four drying processes on the solid-liquid extraction of bioactive compounds from two by-products, olive leaves and pomace, and olive fruits harvested from two cultivars, Alfafara and Koroneiki. Infrared-assisted drying (IAD) was the most suited approach to obtain extracts enriched in oleuropein from leaves (28.5 and 22.2% dry weight in Alfafara and Koroneiki, respectively). In the case of pomace, lyophilization and microwave-assisted drying led to extracts concentrated in oleacein and Oleuropein Aglycone, whereas IAD and oven-drying led to extracts with enhanced contents of hydroxytyrosol glucoside and hydroxytyrosol, respectively. The drying process considerably affected the chemical composition of extracts obtained from fruits. Changes in the composition of the extracts were explained essentially by the drying process conditions using auxiliary energies, temperature, and time, which promoted chemical alterations and increased the extractability of the compounds. Therefore, the drying protocol should be selected depending on the phenolic content and initial raw material.

A Systematic Ex-Vivo Study of the Anti-Proliferative/Cytotoxic Bioactivity of Major Olive Secoiridoids' Double Combinations and of Total Olive Oil Phenolic Extracts on Multiple Cell-Culture Based Cancer Models Highlights Synergistic Effects.[Pubmed:37299499]

Nutrients. 2023 May 29;15(11):2538.

Several individual olive oil phenols (OOPs) and their secoiridoid derivatives have been shown to exert anti-proliferative and pro-apoptotic activity in treatments of human cancer cell lines originating from several tissues. This study evaluated the synergistic anti-proliferative/cytotoxic effects of five olive secoiridoid derivatives (oleocanthal, oleacein, Oleuropein Aglycone, ligstroside aglycone and oleomissional) in all possible double combinations and of total phenolic extracts (TPEs) on eleven human cancer cell lines representing eight cell-culture-based cancer models. Individual OOPs were used to treat cells for 72 h in half of their EC(50) values for each cell line and their synergistic, additive or antagonistic interactions were evaluated by calculating the coefficient for drug interactions (CDI) for each double combination of OOPs. Olive oil TPEs of determined OOPs' content, originating from three different harvests of autochthonous olive cultivars in Greece, were evaluated as an attempt to investigate the efficacy of OOPs to reduce cancer cell numbers as part of olive oil consumption. Most combinations of OOPs showed strong synergistic effect (CDIs < 0.9) in their efficacy, whereas TPEs strongly impaired cancer cell viability, better than most individual OOPs tested herein, including the most resistant cancer cell lines evaluated.

Oleuropein: Chemistry, extraction techniques and nutraceutical perspectives-An update.[Pubmed:37272499]

Crit Rev Food Sci Nutr. 2023 Jun 5:1-22.

Olive family (Oleaceae) contains several species among which Olea europaea L. is mostly used for production of olive oils. Various parts of olive tree are rich source of diverse bioactive compounds such as Apigenin, elenolic acid, Hydroxytyrosol, Ligstroside, Oleoside, Oleuropein, Oleuropein Aglycone, Tyrosol, etc. Among these, oleuropein, a secoiridoid is predominantly found in olive leaves and young olive fruits of different species of Oleaceae family. Scientists have adopted numerous extraction methods (conventional & latest) to increase the yield of oleuropein. Among these techniques, maceration, soxhlet, microwave-assisted, ultrasonication, and supercritical fluid methods are most commonly employed for extraction of oleuropein. Evidently, this review emphasizes on various in-vitro and in-vivo studies focusing on nutraceutical properties of oleuropein. Available literature highlights the pharmaceutical potential of oleuropein against various diseases such as obesity, diabetes, cardiovascular complications, neurodegenerative diseases, cancer, inflammation, microbial infections, and oxidation. This review will benefit the scientific community as it narrates comprehensive literature regarding absorption, metabolism, bioavailability, extraction techniques, and nutraceutical perspectives associated with oleuropein.

Storage Stability of Arauco Virgin Olive Oil: Evolution of Its Quality Parameters and Phenolic and Triterpenic Compounds under Different Conservation Conditions.[Pubmed:37176884]

Plants (Basel). 2023 Apr 29;12(9):1826.

The storage conditions are very critical to minimize hydrolytic and oxidative reactions of virgin olive oils (VOOs). These reactions are logically influenced by the composition of the VOO, so that each variety may have a specific behavior. The aim of this study was to evaluate changes in quality parameters and in the phenolic and triterpenic profile of Arauco VOOs, a unique local variety from Argentina, after storage under different conditions. The effects of exposure to light (darkness and light), temperature (24 and 40 degrees C), packaging material (polyethylene (PET) and dark glass), and headspace (air and N(2) atmosphere) were investigated for 76 days. A reduction in total phenolic compounds was observed after storage treatments, but all samples still complied with the EFSA health claim after the different handlings. Overall, the results revealed that the preservation of the oils in PET appears adequate, with improved stability when N(2) was used in the headspace, along with darkness and low temperature. The study of phenolic profiles showed that substances previously reported as possible markers of olive oil aging, such as hydroxytyrosol and an isomer of decarboxymethyl Oleuropein Aglycone, also have a similar behavior during the aging of Arauco variety oil. Interestingly, some evidence was found that another oleuropein-derived compound (Oleuropein Aglycone isomer 3) could also be used as an aging marker.

Effect of micronization on olive pomace biotransformation in the static model of colonic fermentation.[Pubmed:36996652]

Food Chem. 2023 Aug 30;418:135921.

The effect of granulometric fractionation and micronization of olive pomace (OP) on the biotransformation of phenolic compounds by intestinal microbiota was investigated in vitro. Three types of powdered OP samples were incubated with human feces to simulate colonic fermentation, after a sequential static digestion: non-fractionated OP (NF), granulometrically fractionated OP (GF) and granulometrically fractionated and micronized OP (GFM). GF and GFM favored the release of hydroxytyrosol, Oleuropein Aglycone, apigenin and phenolic acid metabolites in the first hours of colonic fermentation compared to NF (up to 41-fold higher). GFM caused higher release of hydroxytyrosol than GF. GFM was the only sample to release tyrosol and sustained tyrosol levels up to 24 h of fermentation. Micronization associated with granulometric fractionation was more efficient than granulometric fractionation alone to increase the release of phenolic compounds from the OP matrix during simulated colonic fermentation and can be further studied for nutraceutical purposes.

New Affordable Methods for Large-Scale Isolation of Major Olive Secoiridoids and Systematic Comparative Study of Their Antiproliferative/Cytotoxic Effect on Multiple Cancer Cell Lines of Different Cancer Origins.[Pubmed:36613449]

Int J Mol Sci. 2022 Dec 20;24(1):3.

Olive oil phenols (OOPs) are associated with the prevention of many human cancers. Some of these have been shown to inhibit cell proliferation and induce apoptosis. However, no systematic comparative study exists for all the investigated compounds under the same conditions, due to difficulties in their isolation or synthesis. Herein are presented innovative methods for large-scale selective extraction of six major secoiridoids from olive oil or leaves enabling their detailed investigation. The cytotoxic/antiproliferative bioactivity of these six compounds was evaluated on sixteen human cancer cell lines originating from eight different tissues. Cell viability with half-maximal effective concentrations (EC50) was evaluated after 72 h treatments. Antiproliferative and pro-apoptotic effects were also assessed for the most bioactive compounds (EC50 Oleuropein Aglycone (3a,b) > ligstroside aglycone (4a,b) > oleacein (2) > oleomissional (6a,b,c) > oleocanthalic acid (7). This is the first detailed study comparing the bioactivity of six OOPs in such a wide array of cancer cell lines, providing a reference for their relative antiproliferative/cytotoxic effect in the investigated cancers.

Hydroxytyrosol oleate: A promising neuroprotective nanocarrier delivery system of oleuropein and derivatives.[Pubmed:36535454]

Int J Pharm. 2023 Jan 25;631:122498.

Olive Phenols (OPs) are known to be potent antioxidants and possess various bioactivities and health benefits. Epidemiological studies suggested that consumption of olive oil reduces the risk of different diseases exerting a protective effect against certain malignant tumors (prostate, breast, digestive tract, endothelium, etc.). However, extremely low absorption rate of olive phenolic compounds restricts their bioactivity. In this context, solid lipid nanoparticles (SLNs) are a promising solution because they provide higher drug stability and can incorporate both lipophilic and hydrophilic drugs. Interesting experimental results have been obtained using hydroxytyrosol oleate (HtyOle) as a main component of a nanoparticle delivery system containing oleuropein (OL), Oleuropein Aglycone (3,4-DHPEA-EA), or hydroxytyrosol itself (Hty). In this work, hydroxytyrosol oleate (HtyOle) and hydroxytyrosol oleate (HtyOle)-based solid lipid nanoparticles were prepared and characterized. In addition, we evaluatedin vitro their antioxidant activity by DPPH assays and by ROS formation using the SH-SY5Y cell line.