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Journal articles on the topic 'Oleocanthal'

Author: Grafiati

Published: 14 March 2023

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1

Esposito Salsano, Jasmine, Maria Digiacomo, Doretta Cuffaro, Simone Bertini, and Marco Macchia. "Content Variations in Oleocanthalic Acid and Other Phenolic Compounds in Extra-Virgin Olive Oil during Storage." Foods 11, no. 9 (May 6, 2022): 1354. http://dx.doi.org/10.3390/foods11091354.

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The health benefits of extra-virgin olive oil (EVOO) are strictly linked to the presence of phenolic compounds, which exhibit numerous nutraceutical properties. In EVOO, the most important class of phenolic compounds is represented by secoiridoids (oleacein and oleocanthal). EVOO is constantly subjected to degradation processes, including hydrolytic and oxidative reactions that influence its phenolic composition. In particular, the hydrolytic reactions determine the transformation of oleocanthal and oleacein into the corresponding phenyl-alcohols, tyrosol, and hydroxytyrosol. Furthermore, oleocanthal by oxidation processes can be converted to oleocanthalic acid. In this study, we evaluated the phenolic composition of three EVOO samples kept at different storage conditions for 15 months, focusing on the variation of oleocanthalic acid content. Specifically, the samples were stored at 4 °C in darkness and at 25 °C with light exposure. The results of our analyses highlighted that in EVOOs exposed to light and maintained at 25 °C, the degradation was more marked than in EVOO stored in dark and at 4 °C, due to the greater influence of external factors on storage conditions. Although chemical–physical characteristics of EVOOs are slightly different depending on provenience and treatment time, the results of this study reveal that storage conditions are fundamental to controlling phenol concentration.

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2

Liu, Xiuye, Lijuan Yang, Li Wang, and Qiongmei Guo. "Oleocanthal protects against neuronal inflammation and cardiopulmonary bypass surgery-induced brain injury in rats by regulating the NLRP3 pathway." Restorative Neurology and Neuroscience 39, no. 1 (February 26, 2021): 39–44. http://dx.doi.org/10.3233/rnn-201073.

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Background: Open heart surgery is performed with the aid of cardiopulmonary bypass (CPB) techniques that may cause neuronal injuries. Objective: This study investigated the potential protective effect of oleocanthal pre-treatment against CPB-induced cerebral injury. Methods: Oleocanthal 30 mg/kg i.p. was administered 3 h before CPB induction in the treated group. Behavioral neurological scores and cerebral injury were assessed to determine the effects of oleocanthal, based on oxidative stress and serum mediators of inflammation by enzyme-linked immunosorbent assay (ELISA). Quantitative Polymerase Chain Reaction (qRT-PCR) was used to estimate the mRNA expression of Toll-like receptor 4 (TLR4) and Interleukin 1 Receptor Associated Kinase 4 (IRAK4) proteins in the cerebral tissue of rats CPB-induced injury. Western blot assay and histopathology were also performed. Results: The findings suggest that pre-treatment with oleocanthal reduced neurological dysfunction and cerebral injury. Parameters of oxidative stress and cytokine levels were reduced in the serum of the oleocanthal treated group compared with the CPB-only group. Pre-treatment with oleocanthal ameliorated the expression of TLR-4, IRAK4, and Zonula occludens-1 (ZO-1) proteins in the cerebral tissue of the CPB-injured rats. Conclusions: The results revealed that treatment with oleocanthal protected against cerebral damage by controlling microglia inflammation through the TLR-4 pathway.

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3

Giusti, Laura, Cristina Angeloni, Maria Barbalace, Serena Lacerenza, Federica Ciregia, Maurizio Ronci, Andrea Urbani, et al. "A Proteomic Approach to Uncover Neuroprotective Mechanisms of Oleocanthal against Oxidative Stress." International Journal of Molecular Sciences 19, no. 8 (August 8, 2018): 2329. http://dx.doi.org/10.3390/ijms19082329.

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Neurodegenerative diseases represent a heterogeneous group of disorders that share common features like abnormal protein aggregation, perturbed Ca2+ homeostasis, excitotoxicity, impairment of mitochondrial functions, apoptosis, inflammation, and oxidative stress. Despite recent advances in the research of biomarkers, early diagnosis, and pharmacotherapy, there are no treatments that can halt the progression of these age-associated neurodegenerative diseases. Numerous epidemiological studies indicate that long-term intake of a Mediterranean diet, characterized by a high consumption of extra virgin olive oil, correlates with better cognition in aged populations. Olive oil phenolic compounds have been demonstrated to have different biological activities like antioxidant, antithrombotic, and anti-inflammatory activities. Oleocanthal, a phenolic component of extra virgin olive oil, is getting more and more scientific attention due to its interesting biological activities. The aim of this research was to characterize the neuroprotective effects of oleocanthal against H2O2-induced oxidative stress in neuron-like SH-SY5Y cells. Moreover, protein expression profiling, combined with pathways analyses, was used to investigate the molecular events related to the protective effects. Oleocanthal was demonstrated to counteract oxidative stress, increasing cell viability, reducing reactive oxygen species (ROS) production, and increasing reduced glutathione (GSH) intracellular level. Proteomic analysis revealed that oleocanthal significantly modulates 19 proteins in the presence of H2O2. In particular, oleocanthal up-regulated proteins related to the proteasome, the chaperone heat shock protein 90, the glycolytic enzyme pyruvate kinase, and the antioxidant enzyme peroxiredoxin 1. Moreover, oleocanthal protection seems to be mediated by Akt activation. These data offer new insights into the molecular mechanisms behind oleocanthal protection against oxidative stress.

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4

Cassiano, Chiara, Agostino Casapullo, Alessandra Tosco, Maria Chiara Monti, and Raffaele Riccio. "In Cell Interactome of Oleocanthal, an Extra Virgin Olive Oil Bioactive Component." Natural Product Communications 10, no. 6 (June 2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000654.

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A copper-(I)-catalyzed variation of the Huisgen 1,3-dipolar cycloaddition has been applied to lead the in living-cell mass-spectrometry based identification of protein targets of oleocanthal, a natural metabolite daily ingested by millions of people. Chemical proteomics revealed heat-shock proteins, HSP70 and HSP90, as main oleocanthal interactors in living systems. These two proteins are involved in cancer development and, thus, our findings could have important outcomes for a deep evaluation of the bio-pharmacological significance of oleocanthal.

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5

Papakonstantinou, Aikaterini, Petrina Koumarianou, Aimilia Rigakou, Panagiotis Diamantakos, Efseveia Frakolaki, Niki Vassilaki, Evangelia Chavdoula, Eleni Melliou, Prokopios Magiatis, and Haralabia Boleti. "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." International Journal of Molecular Sciences 24, no. 1 (December 20, 2022): 3. http://dx.doi.org/10.3390/ijms24010003.

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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 ≤ 50 μΜ). Oleocanthal (1) showed the strongest antiproliferative/cytotoxic activity in most cancer cell lines (EC50: 9–20 μΜ). The relative effectiveness of the six OOPs was: oleocanthal (1) > 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.

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6

Goren, Limor, George Zhang, Susmita Kaushik, Paul A. S. Breslin, Yi-Chieh Nancy Du, and David A. Foster. "(-)-Oleocanthal and (-)-oleocanthal-rich olive oils induce lysosomal membrane permeabilization in cancer cells." PLOS ONE 14, no. 8 (August 14, 2019): e0216024. http://dx.doi.org/10.1371/journal.pone.0216024.

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7

El Haouari, Mohammed, Juan E. Quintero, and Juan A. Rosado. "Anticancer molecular mechanisms of oleocanthal." Phytotherapy Research 34, no. 11 (May 24, 2020): 2820–34. http://dx.doi.org/10.1002/ptr.6722.

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8

De Stefanis, Scimè, Accomazzo, Catti, Occhipinti, Bertea, and Costelli. "Anti-Proliferative Effects of an Extra-Virgin Olive Oil Extract Enriched in Ligstroside Aglycone and Oleocanthal on Human Liver Cancer Cell Lines." Cancers 11, no. 11 (October 24, 2019): 1640. http://dx.doi.org/10.3390/cancers11111640.

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Oleocanthal and ligstroside aglycone are olive oil-derived polyphenols. The former interferes with tumor growth with minor or no cytotoxicity on non-tumorigenic primary cell lines. The information about the bioactivity of ligstroside aglycone are scanty, with the exception of a known antioxidant power. Hepatocellular carcinoma is a malignant tumor with high mortality rates. Systemic chemotherapy is only marginally effective and is frequently complicated by toxicity. Previous observations have shown that hepatocellular carcinoma cell lines become more sensitive to taxol when it is combined with Tumor Necrosis Factor α (TNFα). The present work aimed to assess the effects of a polyphenolic extract containing both oleocanthal and ligstroside aglycone on proliferation and/or death in three liver cancer cell lines (HepG2, Huh7 and Hep3B). The possibility to enhance such effect by the addition of TNFα was also investigated. Both cell proliferation and death were enhanced by the exposure to the polyphenolic extract. Such effect was associated with induction of autophagy and could be potentiated by TNFα. The presence of ligstroside aglycone in the extract lowered the oleocanthal concentration required for cytotoxicity. These results show for the first time that the effects of a polyphenol extract can be potentiated by TNFα and that modulation of autophagy likely account for these effects.

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9

Monti, Maria Chiara, Luigi Margarucci, Raffaele Riccio, and Agostino Casapullo. "Modulation of Tau Protein Fibrillization by Oleocanthal." Journal of Natural Products 75, no. 9 (September 18, 2012): 1584–88. http://dx.doi.org/10.1021/np300384h.

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10

Cicerale, S., X. A. Conlan, N. W. Barnett, and R. S. J. Keast. "The concentration of oleocanthal in olive oil waste." Natural Product Research 25, no. 5 (March 2011): 542–48. http://dx.doi.org/10.1080/14786419.2010.511214.

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11

Valli, Matteo, Elena Giulia Peviani, Alessio Porta, Alessandro D'Alfonso, Giuseppe Zanoni, and Giovanni Vidari. "A Concise and Efficient Total Synthesis of Oleocanthal." European Journal of Organic Chemistry 2013, no. 20 (May 23, 2013): 4332–36. http://dx.doi.org/10.1002/ejoc.201300324.

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12

Fogliano, Vincenzo, and Raffaele Sacchi. "Oleocanthal in olive oil: Between myth and reality." Molecular Nutrition & Food Research 50, no. 1 (January 2006): 5–6. http://dx.doi.org/10.1002/mnfr.200690002.

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13

Montoya, Tatiana, Catalina Alarcón-de-la-Lastra, María Luisa Castejón, Juan Ortega-Vidal, Joaquín Altarejos, and Marina Sánchez-Hidalgo. "(−)-Methyl-Oleocanthal, a New Oleocanthal Metabolite Reduces LPS-Induced Inflammatory and Oxidative Response: Molecular Signaling Pathways and Histones Epigenetic Modulation." Antioxidants 11, no. 1 (December 27, 2021): 56. http://dx.doi.org/10.3390/antiox11010056.

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The antioxidant and anti-inflammatory responses of (−)-methyl-oleocanthal (met-OLE), a new metabolite of the extra virgin olive oil (EVOO) phenolic oleocanthal (OLE), were explored in lipopolysaccharide (LPS)-induced murine peritoneal macrophages. Possible signaling pathways and epigenetic modulation of histones were studied. Met-OLE inhibited LPS-induced intracellular reactive oxygen species (ROS) and nitrite (NO) production and decreased the overexpression of the pro-inflammatory enzymes COX-2, mPGES-1 and iNOS in murine macrophages. In addition, met-OLE was able to significantly decrease the activation of p38, JNK, and ERK mitogen-activated protein kinases (MAPKs) and blocked canonical and non-canonical inflammasome signaling pathways. On the contrary, met-OLE upregulated haem oxigenase 1 (HO-1) and nuclear factor (erythroid-derived 2)-like 2 (Nrf-2) expression in treated cells. Finally, met-OLE pretreated spleen cells counteracted LPS induction, preventing H3K18 acetylation or H3K9 and H3K27 demethylation. Overall, these results provide novel mechanistic insights into the beneficial effects of met-OLE regarding the regulation of the immune–inflammatory response through epigenetic changes in histone markers. This revealing evidence suggests that the methylated metabolite of OLE may contribute significantly to the beneficial effects that are associated with the secoiridoid-related compound and the usual consumption of EVOO.

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14

Abdallah, Ihab M., Kamal M. Al-Shami, Amer E. Alkhalifa, Nour F. Al-Ghraiybah, Claudia Guillaume, and Amal Kaddoumi. "Comparison of Oleocanthal-Low EVOO and Oleocanthal against Amyloid-β and Related Pathology in a Mouse Model of Alzheimer’s Disease." Molecules 28, no. 3 (January 27, 2023): 1249. http://dx.doi.org/10.3390/molecules28031249.

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Alzheimer’s disease (AD) is characterized by several pathological hallmarks, including the deposition of amyloid-β (Aβ) plaques, neurofibrillary tangles, blood–brain barrier (BBB) dysfunction, and neuroinflammation. Growing evidence support the neuroprotective effects of extra-virgin olive oil (EVOO) and oleocanthal (OC). In this work, we aimed to evaluate and compare the beneficial effects of equivalent doses of OC-low EVOO (0.5 mg total phenolic content/kg) and OC (0.5 mg OC/kg) on Aβ and related pathology and to assess their effect on neuroinflammation in a 5xFAD mouse model with advanced pathology. Homozygous 5xFAD mice were fed with refined olive oil (ROO), OC-low EVOO, or OC for 3 months starting at the age of 3 months. Our findings demonstrated that a low dose of 0.5 mg/kg EVOO-phenols and OC reduced brain Aβ levels and neuroinflammation by suppressing the nuclear factor-κB (NF-κB) pathway and reducing the activation of NOD-, LRR- and pyrin domain-containing protein 3 (NLRP3) inflammasomes. On the other hand, only OC suppressed the receptor for advanced glycation endproducts/high-mobility group box 1 (RAGE/HMGB1) pathway. In conclusion, our results indicated that while OC-low EVOO demonstrated a beneficial effect against Aβ-related pathology in 5xFAD mice, EVOO rich with OC could provide a higher anti-inflammatory effect by targeting multiple mechanisms. Collectively, diet supplementation with EVOO or OC could prevent, halt progression, and treat AD.

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15

Li, Xueqi, Grant C. Bremer, Kristen N. Connell, Courtney Ngai, Quyen Anh T. Pham, Shengling Wang, Mary Flynn, et al. "Changes in Chemical Compositions of Olive Oil under Different Heating Temperatures Similar to Home Cooking." Journal of Food Chemistry and Nutrition 4, no. 1 (June 15, 2016): 07–15. http://dx.doi.org/10.33687/jfcn.004.01.1532.

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Four olive oils with varying amounts of total phenols were exposed to four different heating conditions. Chemical parameters such as free fatty acid, peroxide values, UV absorbency, total phenols, individual phenols, α-tocopherol, squalene, oleocanthal, fatty acid profile and smoke point were measured before and after heating to evaluate the impact of heating conditions on the oils. We found olive oils have reasonably high smoke point that is suitable for typical home-cooking conditions and fresh olive oil with low FFA and high phenolics are important for the conservation of olive oil quality and health benefits. A larger degree of oxidation occurred as with increase of heating time and temperature, oils with high level of phenols produced less polar compounds than oils with lower levels of phenols, including refined oils. A significant amount of total phenols and individual phenols such as oleocanthal remained after heating at 121 °C for 10 and 20 minutes, most of squalene stay intact even after heating at 220 °C.

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16

Francioso, Antonio, Rodolfo Federico, Anna Maggiore, Mario Fontana, Alberto Boffi, Maria D’Erme, and Luciana Mosca. "Green Route for the Isolation and Purification of Hyrdoxytyrosol, Tyrosol, Oleacein and Oleocanthal from Extra Virgin Olive Oil." Molecules 25, no. 16 (August 11, 2020): 3654. http://dx.doi.org/10.3390/molecules25163654.

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Extra virgin olive oil (EVOO) phenols represent a significant part of the intake of antioxidants and bioactive compounds in the Mediterranean diet. In particular, hydroxytyrosol (HTyr), tyrosol (Tyr), and the secoiridoids oleacein and oleocanthal play central roles as anti-inflammatory, neuro-protective and anti-cancer agents. These compounds cannot be easily obtained via chemical synthesis, and their isolation and purification from EVOO is cumbersome. Indeed, both processes involve the use of large volumes of organic solvents, hazardous reagents and several chromatographic steps. In this work we propose a novel optimized procedure for the green extraction, isolation and purification of HTyr, Tyr, oleacein and oleocanthal directly from EVOO, by using a Natural Deep Eutectic Solvent (NaDES) as an extracting phase, coupled with preparative high-performance liquid chromatography. This purification method allows the total recovery of the four components as single pure compounds directly from EVOO, in a rapid, economic and ecologically sustainable way, which utilizes biocompatible reagents and strongly limits the use or generation of hazardous substances.

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17

Starec, Martina, Antonella Calabretti, Federico Berti, and Cristina Forzato. "Oleocanthal Quantification Using 1H NMR Spectroscopy and Polyphenols HPLC Analysis of Olive Oil from the Bianchera/Belica Cultivar." Molecules 26, no. 1 (January 5, 2021): 242. http://dx.doi.org/10.3390/molecules26010242.

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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 1H NMR (qNMR) and HPLC analyses, where qNMR 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.

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18

Olmo-Cunillera, Alexandra, Julián Lozano-Castellón, Maria Pérez, Eleftherios Miliarakis, Anna Tresserra-Rimbau, Antònia Ninot, Agustí Romero-Aroca, Rosa Maria Lamuela-Raventós, and Anna Vallverdú-Queralt. "Optimizing the Malaxation Conditions to Produce an Arbequina EVOO with High Content of Bioactive Compounds." Antioxidants 10, no. 11 (November 17, 2021): 1819. http://dx.doi.org/10.3390/antiox10111819.

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To meet the growing demand for high-quality extra-virgin olive oil (EVOO) with health-promoting properties and pleasant sensory properties, studies are needed to establish optimal production parameters. Bioactive components of EVOO, including phenolic compounds, carotenoids, chlorophylls, tocopherols, and squalene, contribute to its organoleptic properties and beneficial health effects. The aim of this study was to develop an Arbequina EVOO with high phenol content, particularly oleocanthal and oleacein, on a laboratory scale by analyzing the effects of different temperatures (20, 25, and 30 °C) and times (30 and 45 min) of malaxation. Higher temperatures decreased the levels of the phenolic compounds, secoiridoids, tocopherols, and squalene, but increased the pigments. EVOO with the highest quality was produced using malaxation parameters of 20 °C and 30 min, although oleocanthal and oleacein were higher at 30 and 25 °C, respectively. Overall, 20 °C and 30 min were the processing conditions that most favored the physiological and chemical processes that contribute to higher levels of bioactive compounds in the oil and diminished their degradation and oxidation processes.

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19

Pang, Kok-Lun, and Kok-Yong Chin. "The Biological Activities of Oleocanthal from a Molecular Perspective." Nutrients 10, no. 5 (May 6, 2018): 570. http://dx.doi.org/10.3390/nu10050570.

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20

López-Yerena, Vallverdú-Queralt, Mols, Augustijns, Lamuela-Raventós, and Escribano-Ferrer. "Absorption and Intestinal Metabolic Profile of Oleocanthal in Rats." Pharmaceutics 12, no. 2 (February 5, 2020): 134. http://dx.doi.org/10.3390/pharmaceutics12020134.

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Oleocanthal (OLC), a phenolic compound of extra virgin olive oil (EVOO), has emerged as a potential therapeutic agent against a variety of diseases due to its anti-inflammatory activity. The aim of the present study is to explore its in vivo intestinal absorption and metabolism. An in situ perfusion technique in rats was used, involving simultaneous sampling from the luminal perfusate and mesenteric blood. Samples were analysed by UHPLC–MS–MS for the presence of oleocanthal (OLC) and its metabolites. OLC was mostly metabolized by phase I metabolism, undergoing hydration, hydrogenation and hydroxylation. Phase II reactions (glucuronidation of hydrogenated OLC and hydrated metabolites) were observed in plasma samples. OLC was poorly absorbed in the intestine, as indicated by the low effective permeability coefficient (2.23 ± 3.16 × 10−5 cm/s) and apparent permeability coefficient (4.12 ± 2.33 × 10−6 cm/s) obtained relative to the values of the highly permeable reference compound levofloxacin (LEV). The extent of OLC absorption reflected by the area under the mesenteric blood-time curve normalized by the inlet concentration (AUC) was also lower than that of LEV (0.25 ± 0.04 vs. 0.64 ± 0.03, respectively). These results, together with the observed intestinal metabolism, suggest that OLC has a moderate-to-low oral absorption; but higher levels of OLC are expected to reach human plasma vs. rat plasma.

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21

Qusa, Mohammed H., Khaldoun S. Abdelwahed, Ronald A. Hill, and Khalid A. El El Sayed. "S-(-)-Oleocanthal Ex Vivo Modulatory Effects on Gut Microbiota." Nutrients 15, no. 3 (January 25, 2023): 618. http://dx.doi.org/10.3390/nu15030618.

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Compelling evidence points to the critical role of bioactive extra-virgin olive oil (EVOO) phenolics and gut microbiota (GM) interplay, but reliable models for studying the consequences thereof remain to be developed. Herein, we report an optimized ex vivo fecal anaerobic fermentation model to study the modulation of GM by the most bioactive EVOO phenolic S-(−)-oleocanthal (OC), and impacts therefrom, focusing on OC biotransformation in the gut. This model will also be applicable for characterization of GM interactions with other EVOO phenolics, and moreover, for a broadly diverse range of bioactive natural products. The fecal fermentation media and time, and mouse type and gender, were the major factors varied and optimized to provide better understanding of GM-OC interplay. A novel resin entrapment technique (solid-phase extraction) served to selectively entrap OC metabolites, degradation products, and any remaining fraction of OC while excluding interfering complex fecal medium constituents. The effects of OC on GM compositions were investigated via shallow shotgun DNA sequencing. Robust metabolome analyses identified GM bacterial species selectively altered (population numbers/fraction) by OC. Finally, the topmost OC-affected gut bacterial species of the studied mice were compared with those known to be extant in humans and distributions of these bacteria at different human body sites. OC intake caused significant quantitative and qualitative changes to mice GM, which was also comparable with human GM. Results clearly highlight the potential positive health outcomes of OC as a prospective nutraceutical.

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22

Segura-Carretero, Antonio, and Jose Curiel. "Current Disease-Targets for Oleocanthal as Promising Natural Therapeutic Agent." International Journal of Molecular Sciences 19, no. 10 (September 24, 2018): 2899. http://dx.doi.org/10.3390/ijms19102899.

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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.

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23

Keiler, Annekathrin, Sefirin Djiogue, Tino Ehrhardt, Oliver Zierau, Leandros Skaltsounis, Maria Halabalaki, and Günter Vollmer. "Oleocanthal Modulates Estradiol-Induced Gene Expression Involving Estrogen Receptor α." Planta Medica 81, no. 14 (July 10, 2015): 1263–69. http://dx.doi.org/10.1055/s-0035-1546194.

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24

Gu, Yanli, Jing Wang, and Lixin Peng. "(−)-Oleocanthal exerts anti-melanoma activities and inhibits STAT3 signaling pathway." Oncology Reports 37, no. 1 (November 23, 2016): 483–91. http://dx.doi.org/10.3892/or.2016.5270.

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25

Margarucci, Luigi, Maria Chiara Monti, Chiara Cassiano, Matteo Mozzicafreddo, Mauro Angeletti, Raffaele Riccio, Alessandra Tosco, and Agostino Casapullo. "Chemical proteomics-driven discovery of oleocanthal as an Hsp90 inhibitor." Chemical Communications 49, no. 52 (2013): 5844. http://dx.doi.org/10.1039/c3cc41858h.

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26

Losito, Ilario, Ramona Abbattista, Cristina De Ceglie, Andrea Castellaneta, Cosima Damiana Calvano, and Tommaso R. I. Cataldi. "Bioactive Secoiridoids in Italian Extra-Virgin Olive Oils: Impact of Olive Plant Cultivars, Cultivation Regions and Processing." Molecules 26, no. 3 (January 31, 2021): 743. http://dx.doi.org/10.3390/molecules26030743.

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In the last two decades, phenolic compounds occurring in olive oils known as secoiridoids have attracted a great interest for their bioactivity. Four major olive oil secoiridoids, i.e., oleuropein and ligstroside aglycones, oleacin and oleocanthal, were previously characterized in our laboratory using reversed-phase liquid chromatography with electrospray ionization-Fourier transform-mass spectrometry (RPLC-ESI-FTMS). The same analytical approach, followed by multivariate statistical analysis (i.e., Principal Component Analysis), was applied here to a set of 60 Italian extra-virgin olive oils (EVOO). The aim was to assess the secoiridoid contents as a function of olive cultivars, place of cultivation (i.e., different Italian regions) and olive oil processing, in particular two- vs. three-phase horizontal centrifugation. As expected, higher secoiridoid contents were generally found in olive oils produced by two-phase horizontal centrifugation. Moreover, some region/cultivar-related trends were evidenced, as oleuropein and ligstroside aglycones prevailed in olive oils produced in Apulia (Southern Italy), whereas the contents of oleacin and oleocanthal were relatively higher in EVOO produced in Central Italy (Tuscany, Lazio and Umbria). A lower content of all the four secoiridoids was generally found in EVOO produced in Sicily (Southern Italy) due to the intrinsic low abundance of these bioactive compounds in cultivars typical of that region.

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27

Abbattista, Ramona, Ilario Losito, Graziana Basile, Andrea Castellaneta, Giovanni Ventura, Cosima Damiana Calvano, and Tommaso R. I. Cataldi. "Hydrogen/Deuterium Exchange Mass Spectrometry for Probing the Isomeric Forms of Oleocanthal and Oleacin in Extra Virgin Olive Oils." Molecules 28, no. 5 (February 22, 2023): 2066. http://dx.doi.org/10.3390/molecules28052066.

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Reversed-phase liquid chromatography and electrospray ionization with Fourier-transform single and tandem mass spectrometry (RPLC-ESI-FTMS and FTMS/MS) were employed for the structural characterization of oleocanthal (OLEO) and oleacin (OLEA), two of the most important bioactive secoiridoids occurring in extra virgin olive oils (EVOOs). The existence of several isoforms of OLEO and OLEA was inferred from the chromatographic separation, accompanied, in the case of OLEA, by minor peaks due to oxidized OLEO recognized as oleocanthalic acid isoforms. The detailed analysis of the product ion tandem MS spectra of deprotonated molecules ([M-H]−) was unable to clarify the correlation between chromatographic peaks and specific OLEO/OLEA isoforms, including two types of predominant dialdehydic compounds, named Open Forms II, containing a double bond between carbon atoms C8 and C10, and a group of diasteroisomeric closed-structure (i.e., cyclic) isoforms, named Closed Forms I. This issue was addressed by H/D exchange (HDX) experiments on labile H atoms of OLEO and OLEA isoforms, performed using deuterated water as a co-solvent in the mobile phase. HDX unveiled the presence of stable di-enolic tautomers, in turn providing key evidence for the occurrence, as prevailing isoforms, of Open Forms II of OLEO and OLEA, different from those usually considered so far as the main isoforms of both secoiridoids (having a C=C bond between C8 and C9). It is expected that the new structural details inferred for the prevailing isoforms of OLEO and OLEA will help in understanding the remarkable bioactivity exhibited by the two compounds.

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Cicerale, Sara, and Russell S.J. Keast. "Oleocanthal, a Natural anti-Inflammatory Compound in Extra Virgin Olive Oil." Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry 9, no. 2 (June 1, 2010): 94–100. http://dx.doi.org/10.2174/187152310791110607.

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Casapullo, Agostino, Federica Del Gaudio, Angela Capolupo, Chiara Cassiano, and Maria Chiara Monti. "Multi-Target Profile of Oleocanthal, An Extra-Virgin Olive Oil Component." Current Bioactive Compounds 12, no. 1 (April 1, 2016): 3–9. http://dx.doi.org/10.2174/1573407212666151231184806.

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Mohyeldin, Mohamed M., Mohamed R. Akl, Hassan Y. Ebrahim, Ana Maria Dragoi, Samantha Dykes, James A. Cardelli, and Khalid A. El Sayed. "The oleocanthal-based homovanillyl sinapate as a novel c-Met inhibitor." Oncotarget 7, no. 22 (April 11, 2016): 32247–73. http://dx.doi.org/10.18632/oncotarget.8681.

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Francisco, Vera, Clara Ruiz-Fernández, Vicente Lahera, Francisca Lago, Jesús Pino, Leandros Skaltsounis, Miguel Angel González-Gay, et al. "Natural Molecules for Healthy Lifestyles: Oleocanthal from Extra Virgin Olive Oil." Journal of Agricultural and Food Chemistry 67, no. 14 (March 15, 2019): 3845–53. http://dx.doi.org/10.1021/acs.jafc.8b06723.

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English, Brandon J., and Robert M. Williams. "Synthesis of (±)-oleocanthal via a tandem intramolecular Michael cyclization–HWE olefination." Tetrahedron Letters 50, no. 23 (June 2009): 2713–15. http://dx.doi.org/10.1016/j.tetlet.2009.03.145.

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Ünsal, Ülkün Ünlü, Mesut Mete, Işil Aydemir, Yusuf Kurtuluş Duransoy, Ahmet Şükrü Umur, and Mehmet Ibrahim Tuglu. "Inhibiting effect of oleocanthal on neuroblastoma cancer cell proliferation in culture." Biotechnic & Histochemistry 95, no. 3 (November 6, 2019): 233–41. http://dx.doi.org/10.1080/10520295.2019.1674919.

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Chiang, Yi-Fen, Hui-Chih Hung, Hsin-Yuan Chen, Ko-Chieh Huang, Po-Han Lin, Jen-Yun Chang, Tsui-Chin Huang, and Shih-Min Hsia. "The Inhibitory Effect of Extra Virgin Olive Oil and Its Active Compound Oleocanthal on Prostaglandin-Induced Uterine Hypercontraction and Pain—Ex Vivo and In Vivo Study." Nutrients 12, no. 10 (September 30, 2020): 3012. http://dx.doi.org/10.3390/nu12103012.

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Primary dysmenorrhea is a common occurrence in adolescent women and is a type of chronic inflammation. Dysmenorrhea is due to an increase in oxidative stress, which increases cyclooxygenase-2 (COX-2) expression, increases the concentration of prostaglandin F2α (PGF2α), and increases the calcium concentration in uterine smooth muscle, causing excessive uterine contractions and pain. The polyphenolic compound oleocanthal (OC) in extra virgin olive oil (EVOO) has been shown to have an anti-inflammatory and antioxidant effect. This study aimed to investigate the inhibitory effect of extra virgin olive oil and its active ingredient oleocanthal (OC) on prostaglandin-induced uterine hyper-contraction, its antioxidant ability, and related mechanisms. We used force-displacement transducers to calculate uterine contraction in an ex vivo study. To analyze the analgesic effect, in an in vivo study, we used an acetic acid/oxytocin-induced mice writhing model and determined uterus contraction-related signaling protein expression. The active compound OC inhibited calcium/PGF2α-induced uterine hyper-contraction. In the acetic acid and oxytocin-induced mice writhing model, the intervention of the EVOO acetonitrile layer extraction inhibited pain by inhibiting oxidative stress and the phosphorylation of the protein kinase C (PKC)/extracellular signal-regulated kinases (ERK)/ myosin light chain (MLC) signaling pathway. These findings supported the idea that EVOO and its active ingredient, OC, can effectively decrease oxidative stress and PGF2α-induced uterine hyper-contraction, representing a further treatment for dysmenorrhea.

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López-Yerena, Anallely, Anna Vallverdú-Queralt, Raf Mols, Patrick Augustijns, Rosa M. Lamuela-Raventós, and Elvira Escribano-Ferrer. "Reply to “Comment on López-Yerena et al. ‘Absorption and Intestinal Metabolic Profile of Oleocanthal in Rats’ Pharmaceutics 2020, 12, 134”." Pharmaceutics 12, no. 12 (December 17, 2020): 1221. http://dx.doi.org/10.3390/pharmaceutics12121221.

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Recently, in February 2020, we published a study exploring the intestinal absorption and metabolism of oleocanthal (OLC) in rats. A single-pass intestinal perfusion technique (SPIP) was used, involving simultaneous sampling from the luminal perfusate and mesenteric blood. Later, comments on our published paper were released, requesting clarification of specific data. In this detailed reply, we hope to have addressed and clarified all the concerns of A. Kaddoumi and K. El Sayed and that the scientific community will benefit from both the study and the comments it has generated.

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López-Yerena, Anallely, Anna Vallverdú-Queralt, Olga Jáuregui, Xavier Garcia-Sala, Rosa M. Lamuela-Raventós, and Elvira Escribano-Ferrer. "Tissue Distribution of Oleocanthal and Its Metabolites after Oral Ingestion in Rats." Antioxidants 10, no. 5 (April 27, 2021): 688. http://dx.doi.org/10.3390/antiox10050688.

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Claims for the potential health benefits of oleocanthal (OLC), a dietary phenolic compound found in olive oil, are based mainly on in vitro studies. Little is known about the tissue availability of OLC, which is rapidly metabolized after ingestion. In this study, the distribution of OLC and its metabolites in rat plasma and tissues (stomach, intestine, liver, kidney, spleen, lungs, heart, brain, thyroid and skin) at 1, 2 and 4.5 h after the acute intake of a refined olive oil containing 0.3 mg/mL of OLC was examined by LC-ESI-LTQ-Orbitrap-MS. OLC was only detected in the stomach and intestine samples. Moreover, at 2 and 4.5 h, the concentration in the stomach decreased by 36% and 74%, respectively, and in the intestine by 16% and 33%, respectively. Ten OLC metabolites arising from phase I and phase II reactions were identified. The metabolites were widely distributed in rat tissues, and the most important metabolizing organs were the small intestine and liver. The two main circulating metabolites were the conjugates OLC + OH + CH3 and OLC + H2O + glucuronic acid, which may significantly contribute to the beneficial health effects associated with the regular consumption of extra virgin olive oil. However, more studies are necessary to determine the concentrations and molecular structures of OLC metabolites in human plasma and tissues when consumed with the presence of other phenolic compunds present in EVOO.

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LeGendre, Onica, Paul AS Breslin, and David A. Foster. "(-)-Oleocanthal rapidly and selectively induces cancer cell death via lysosomal membrane permeabilization." Molecular & Cellular Oncology 2, no. 4 (January 23, 2015): e1006077. http://dx.doi.org/10.1080/23723556.2015.1006077.

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Adhami, Hamid-Reza, Martin Zehl, Christina Dangl, Dominic Dorfmeister, Marco Stadler, Ernst Urban, Peter Hewitson, Svetlana Ignatova, and Liselotte Krenn. "Preparative isolation of oleocanthal, tyrosol, and hydroxytyrosol from olive oil by HPCCC." Food Chemistry 170 (March 2015): 154–59. http://dx.doi.org/10.1016/j.foodchem.2014.08.079.

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Bouymajane, Aziz, Yassine Oulad El Majdoub, Francesco Cacciola, Marina Russo, Fabio Salafia, Alessandra Trozzi, Fouzia Rhazi Filali, Paola Dugo, and Luigi Mondello. "Characterization of Phenolic Compounds, Vitamin E and Fatty Acids from Monovarietal Virgin Olive Oils of “Picholine marocaine” Cultivar." Molecules 25, no. 22 (November 19, 2020): 5428. http://dx.doi.org/10.3390/molecules25225428.

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Olive oil is an important product in the Mediterranean diet, due to its health benefits and sensorial characteristics. Picholine marocaine is the most cultivated variety in Morocco. The present research aims to evaluate the phenolic compounds, vitamin E and fatty acids of commercial Picholine marocaine virgin olive oils (VOOs) from five different North Moroccan provinces (Chefchaouen, Taounate, Errachidia, Beni Mellal and Taza), using HPLC-photodiode array (PDA)/electrospray ionization (ESI)-MS, normal phase (NP)-HPLC/ fluorescence detector (FLD) and GC-flame ionization detector (FID)/MS, respectively. The obtained results showed an average content of 130.0 mg kg−1 of secoiridoids (oleuropein aglycone, 10-hydroxy-oleuropein aglycone and ligstroside aglycone, oleocanthal and oleacein), 108.1 mg kg−1 of phenolic alcohols (tyrosol and hydroxytyrosol), 34.7 mg kg−1 of phenolic acids (caffeic acid, ferulic acid and elenolic acid), and 8.24 mg kg−1 of flavonoids (luteolin, luteolin glucoside, apigenin). With regard to vitamin E, α-tocopherol was the most abundant vitamin E (57.9 mg kg−1), followed by α-tocotrienol (2.5 mg kg−1), γ-tocopherol (4.5 mg kg−1) and β-tocopherol (1.9 mg kg−1), while δ-tocopherol was not detected. Moreover, 14 fatty acids were found and, among them, oleic acid (76.1%), linoleic acid (8.1%) palmitic acid (8.7%) and stearic acid (2.5%) were the major fatty acids detected. Finally, heat map and principal component analysis allowed us to classify the studied provinces in terms of VOO chemical composition: Chefchaouen (tyrosol and hydroxytyrosol), Taounate (oleuropein aglycone), Errachidia (ferulic acid, w-3 and w-6), Beni Mellal (oleocanthal) and Taza (luteolin and oleic acid).

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Scotece, Morena, Javier Conde, Vanessa Abella, Veronica López, Vera Francisco, Clara Ruiz, Victor Campos, et al. "Oleocanthal Inhibits Catabolic and Inflammatory Mediators in LPS-Activated Human Primary Osteoarthritis (OA) Chondrocytes Through MAPKs/NF-κB Pathways." Cellular Physiology and Biochemistry 49, no. 6 (2018): 2414–26. http://dx.doi.org/10.1159/000493840.

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Background/Aims: Oleocanthal (OC), a phenolic compound present in extra virgin olive oil (EVOO), has attracted attention since its discovery for its relevant pharmacological properties in different pathogenic processes, including inflammation. Here, we investigated the involvement of OC in LPS-activated osteoarthritis (OA) human primary chondrocytes. Methods: Human primary chondrocytes were harvested from articular cartilage samples obtained from OA patients. The effects of OC on the viability of chondrocytes were tested by MTT assay. Protein and mRNA expression of several catabolic and pro-inflammatory factors after OC treatment were measured by RT-qPCR and western blot respectively. Moreover, we analysed the NO production by Griess reaction. Finally, several pathways mediators were analysed by western blot. Results: We demonstrated that OC did not have any cytotoxic effect. Oleocanthal inhibited NO production and strongly decreased NOS2 and COX-2 protein and mRNA expression in LPS-activated human primary OA chondrocytes. Interestingly, OC also inhibits MMP-13 and ADAMTS-5. In addition, OC downregulates several pro-inflammatory factors, such as IL-6, IL-8, CCL3, LCN2 and TNF-α induced by LPS in human primary OA chondrocytes. Finally, we demonstrated that OC exerts its effects through the MAPK/P38/NF-kB pathways. Conclusion: These data show that OC is able to block LPS-mediated inflammatory response and MMP-13 and ADAMTS-5 induction in human primary OA chondrocytes via MAPKs/NF-kB pathways, suggesting that OC may be a promising agent for the treatment of inflammation in cartilage and a potential molecule to prevent disease progression by inhibiting metalloproteases and aggrecanases.

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P, Koteswari, Gowthami P, Deepika Y, and Abhishek Kumar G. "A Novel Structured Emulsion Containing Oleocanthal Enriched Extra Virgin Olive oil and Curcumin." American Journal of PharmTech Research 9, no. 6 (December 8, 2019): 201–12. http://dx.doi.org/10.46624/ajptr.2019.v9.i6.017.

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Siddique, Abu Bakar, Hassan Y. Ebrahim, Afsana Tajmim, Judy Ann King, Khaldoun S. Abdelwahed, Zakaria Y. Abd Elmageed, and Khalid A. El Sayed. "Oleocanthal Attenuates Metastatic Castration-Resistant Prostate Cancer Progression and Recurrence by Targeting SMYD2." Cancers 14, no. 14 (July 21, 2022): 3542. http://dx.doi.org/10.3390/cancers14143542.

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Metastatic castration-resistant prostate cancer (mCRPC) is the most aggressive prostate cancer (PC) phenotype. Cellular lysine methylation is driven by protein lysine methyltransferases (PKMTs), such as those in the SET- and MYND-containing protein (SMYD) family, including SMYD2 methylate, and several histone and non-histone proteins. SMYD2 is dysregulated in metastatic PC patients with high Gleason score and shorter survival. The Mediterranean, extra-virgin-olive-oil-rich diet ingredient S-(-)-oleocanthal (OC) inhibited SMYD2 in biochemical assays and suppressed viability, migration, invasion, and colony formation of PC-3, CWR-R1ca, PC-3M, and DU-145 PC cell lines with IC50 range from high nM to low µM. OC’s in vitro antiproliferative effect was comparable to standard anti-PC chemotherapies or hormone therapies. A daily, oral 10 mg/kg dose of OC for 11 days effectively suppressed the progression of the mCRPC CWR-R1ca cells engrafted into male nude mice. Daily, oral OC treatment for 30 days suppressed tumor locoregional and distant recurrences after the primary tumors’ surgical excision. Collected OC-treated animal tumors showed marked SMYD2 reduction. OC-treated mice showed significant serum PSA reduction. For the first time, this study showed SMYD2 as novel molecular target in mCRPC, and OC emerged as a specific SMYD2 lead inhibitor. OC prevailed over previously reported SMYD2 inhibitors, with validated in vivo potency and high safety profile, and, therefore, is proposed as a novel nutraceutical for mCRPC progression and recurrence control.

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Li, Wenjun, Maria Chountoulesi, Lemonia Antoniadi, Apostolis Angelis, Jiandu Lei, Maria Halabalaki, Costas Demetzos, Sofia Mitakou, Leandros A. Skaltsounis, and Chengzhang Wang. "Development and physicochemical characterization of nanoliposomes with incorporated oleocanthal, oleacein, oleuropein and hydroxytyrosol." Food Chemistry 384 (August 2022): 132470. http://dx.doi.org/10.1016/j.foodchem.2022.132470.

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Özkut, Mahmud, Gülşah Albayrak, Pınar Kılıçaslan Sönmez, Büşra Şen, Pelin Toros, Şamil Öztürk, Fatih Çöllü, Sevinç İnan, and Mehmet İbrahim Tuğlu. "Anticancer Effects of Oleocanthal and Pinus Pinaster on Breast Cancer Cell in Culture." Proceedings 1, no. 10 (November 17, 2017): 1020. http://dx.doi.org/10.3390/proceedings1101020.

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45

Scotece, M., R. Gomez, J. Conde, V. Lopez, J. J. Gomez-Reino, F. Lago, A. B. Smith III, and O. Gualillo. "Oleocanthal Inhibits Proliferation and MIP-1α Expression in Human Multiple Myeloma Cells." Current Medicinal Chemistry 20, no. 19 (April 1, 2013): 2467–75. http://dx.doi.org/10.2174/0929867311320190006.

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Fogli, Stefano, Chiara Arena, Sara Carpi, Beatrice Polini, Simone Bertini, Maria Digiacomo, Francesca Gado, et al. "Cytotoxic Activity of Oleocanthal Isolated from Virgin Olive Oil on Human Melanoma Cells." Nutrition and Cancer 68, no. 5 (June 7, 2016): 873–77. http://dx.doi.org/10.1080/01635581.2016.1180407.

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Diamantakos, Panagiotis, Triada Giannara, Maria Skarkou, Eleni Melliou, and Prokopios Magiatis. "Influence of Harvest Time and Malaxation Conditions on the Concentration of Individual Phenols in Extra Virgin Olive Oil Related to Its Healthy Properties." Molecules 25, no. 10 (May 24, 2020): 2449. http://dx.doi.org/10.3390/molecules25102449.

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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.

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De La Cruz Cortés, José Pedro, Inmaculada Pérez de Algaba, Esther Martín-Aurioles, María Monsalud Arrebola, Laura Ortega-Hombrados, María Dolores Rodríguez-Pérez, María África Fernández-Prior, Alejandra Bermúdez-Oria, Cristina Verdugo, and José Antonio González-Correa. "Extra Virgin Oil Polyphenols Improve the Protective Effects of Hydroxytyrosol in an In Vitro Model of Hypoxia-Reoxygenation of Rat Brain." Brain Sciences 11, no. 9 (August 26, 2021): 1133. http://dx.doi.org/10.3390/brainsci11091133.

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Hydroxytyrosol (HT) is the component primarily responsible for the neuroprotective effect of extra virgin olive oil (EVOO). However, it is less effective on its own than the demonstrated neuroprotective effect of EVOO, and for this reason, it can be postulated that there is an interaction between several of the polyphenols of EVOO. The objective of the study was to assess the possible interaction of four EVOO polyphenols (HT, tyrosol, dihydroxyphenylglycol, and oleocanthal) in an experimental model of hypoxia-reoxygenation in rat brain slices. The lactate dehydrogenase (LDH) efflux, lipid peroxidation, and peroxynitrite production were determined as measures of cell death, oxidative stress, and nitrosative stress, respectively. First, the polyphenols were incubated with the brain slices in the same proportions that exist in EVOO, comparing their effects with those of HT. In all cases, the cytoprotective and antioxidant effects of the combination were greater than those of HT alone. Second, we calculated the concentration–effect curves for HT in the absence or presence of each polyphenol. Tyrosol did not significantly modify any of the variables inhibited by HT. Dihydroxyphenylglycol only increased the cytoprotective effect of HT at 10 µM, while it increased its antioxidant effect at 50 and 100 µM and its inhibitory effect on peroxynitrite formation at all the concentrations tested. Oleocanthal increased the cytoprotective and antioxidant effects of HT but did not modify its inhibitory effect on nitrosative stress. The results of this study show that the EVOO polyphenols DHPG and OLC increase the cytoprotective effect of HT in an experimental model of hypoxia-reoxygenation in rat brain slices, mainly due to a possibly synergistic effect on HT’s antioxidant action. These results could explain the greater neuroprotective effect of EVOO than of the polyphenols alone.

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Montoya, Tatiana, Marina Sánchez-Hidalgo, María Luisa Castejón, María Ángeles Rosillo, Alejandro González-Benjumea, and Catalina Alarcón-de-la-Lastra. "Dietary Oleocanthal Supplementation Prevents Inflammation and Oxidative Stress in Collagen-Induced Arthritis in Mice." Antioxidants 10, no. 5 (April 23, 2021): 650. http://dx.doi.org/10.3390/antiox10050650.

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Oleocanthal (OLE), a characteristic and exclusive secoiridoid of Oleoaceae family, is mainly found in extra virgin olive oil (EVOO). Previous studies have reported its antioxidant, anti-inflammatory, antimicrobial, anticancer and neuroprotective effects. Since the pathogenesis of rheumatoid arthritis (RA) involves inflammatory and oxidative components, this study was designed to evaluate the preventive role of dietary OLE-supplemented effects in collagen-induced arthritis (CIA) murine model. Animals were fed with a preventive OLE-enriched dietary during 6 weeks previous to CIA induction and until the end of experiment time. At day 43 after first immunization, mice were sacrificed: blood was recollected and paws were histological and biochemically processed. Dietary OLE prevented bone, joint and cartilage rheumatic affections induced by collagen. Levels of circulatory matrix metalloproteinase (MMP)-3 and pro-inflammatory cytokines (IL-6, IL-1β, TNF-α, IL-17, IFN-γ) were significantly decreased in secoiridoid fed animals. Besides, dietary OLE was able to diminish COX-2, mPGES-1 and iNOS protein expressions and, also, PGE2 levels. The mechanisms underlying these protective effects could be related to Nrf-2/HO-1 axis activation and the inhibition of relevant signaling pathways including JAK-STAT, MAPKs and NF-κB, thus controlling the production of inflammatory and oxidative mediators. Overall, our results exhibit preliminary evidences about OLE, as a novel dietary tool for the prevention of autoimmune and inflammatory disorders, such as RA.

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Siddique, Abu Bakar, Phillip C. S. R. Kilgore, Afsana Tajmim, Sitanshu S. Singh, Sharon A. Meyer, Seetharama D. Jois, Urska Cvek, Marjan Trutschl, and Khalid A. El Sayed. "(−)-Oleocanthal as a Dual c-MET-COX2 Inhibitor for the Control of Lung Cancer." Nutrients 12, no. 6 (June 11, 2020): 1749. http://dx.doi.org/10.3390/nu12061749.

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Lung cancer (LC) represents the topmost mortality-causing cancer in the U.S. LC patients have overall poor survival rate with limited available treatment options. Dysregulation of the mesenchymal epithelial transition factor (c-MET) and cyclooxygenase 2 (COX2) initiates aggressive LC profile in a subset of patients. The Mediterranean extra-virgin olive oil (EVOO)-rich diet already documented to reduce multiple malignancies incidence. (-)-Oleocanthal (OC) is a naturally occurring phenolic secoiridoid exclusively occurring in EVOO and showed documented anti-breast and other cancer activities via targeting c-MET. This study shows the novel ability of OC to suppress LC progression and metastasis through dual targeting of c-MET and COX-2. Western blot analysis and COX enzymatic assay showed significant reduction in the total and activated c-MET levels and inhibition of COX1/2 activity in the lung adenocarcinoma cells A549 and NCI-H322M, in vitro. In addition, OC treatment caused a dose-dependent inhibition of the HGF-induced LC cells migration. Daily oral treatment with 10 mg/kg OC for 8 weeks significantly suppressed the LC A549-Luc progression and prevented metastasis to brain and other organs in a nude mouse tail vein injection model. Further, microarray data of OC-treated lung tumors showed a distinct gene signature that confirmed the dual targeting of c-MET and COX2. Thus, the EVOO-based OC is an effective lead with translational potential for use as a prospective nutraceutical to control LC progression and metastasis.

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