Insights into the Antioxidant/Antiradical Effects and In Vitro Intestinal Permeation of Oleocanthal and Its Metabolites Tyrosol and Oleocanthalic Acid

Abstract

(1) Background: In recent years, numerous studies have highlighted the beneficial effects of extra virgin olive oil (EVOO) as an active ingredient against chronic diseases. The properties of EVOO are due to its peculiar composition, mainly to its rich content of polyphenols. In fact, polyphenols may contribute to counteract oxidative stress, which often accompanies chronic diseases. In this work, the antioxidant effects of high-value polyphenol oleocanthal (OC) and its main metabolites, tyrosol (Tyr) and oleocanthalic acid (OA), respectively, have been investigated along with their impact on cell viability. (2) Methods: OC, Tyr, and OA have been evaluated regarding antiradical properties in term of scavenging capacity towards biologically relevant reactive species, including O2●−, HOCl, and ROO●, as well as their antioxidant/antiradical capacity (FRAP, DPPH●, ABTS●+). Moreover, the ability to permeate the intestinal membrane was assessed by an intestinal co-culture model composed by Caco-2 and HT29-MTX cell lines. (3) Results: The capacity of OC and Tyr as radical oxygen species (ROS) scavengers, particularly regarding HOCl and O2●−, was clearly demonstrated. Furthermore, the ability to permeate the intestinal co-culture model was plainly proved by the good permeations (>50%) achieved by all compounds. (4) Conclusions: OC, OA, and Tyr revealed promising properties against oxidative diseases.

Anti-Cancer, Anti-Angiogenic, and Anti-Atherogenic Potential of Key Phenolic Compounds from Virgin Olive Oil

“…The antioxidant properties of hydroxytyrosol arise from its capacity to function as a potent scavenger of free radicals [44][45][46], its chelating effect on metals-diminishing the production of ROS from derived reactions [47]-and its ability to stimulate various antioxidant systems by promoting the activity of enzymes like catalase (CAT), superoxide dismutase (SOD), and glutathione peroxidase (GPx) [48][49][50][51], or by activating the transcription factor Nrf2 [52,53]. Additionally, (-)-oleocanthal and (-)-oleacein, while not as well studied as hydroxytyrosol for their antioxidant properties, have been shown to act as free radical scavengers [54][55][56].…”

An Appraisal of the Oleocanthal-Rich Extra Virgin Olive Oil (EVOO) and Its Potential Anticancer and Neuroprotective Properties

“…The content of total phenols-expressed as gallic acid equival from 14.80 to 121.20 mg/100 g (mean value: 53.72 mg/100 g) and was mainl to deacetoxyligstroside aglycone, oleuropein aglycone, deacetoxyoleurop and ligstroside aglycone. Trolox equivalent antioxidant capacity (TEAC) a stability were both positively correlated with the phenolic content [26 published study conducted by Cuffaro et al [27] investigated the antioxidan high-value polyphenol oleocanthal and its main metabolites (tyrosol and acid) in terms of scavenging capacity towards biologically relevant rea…”

“…Trolox equivalent antioxidant capacity (TEAC) and oxidative stability were both positively correlated with the phenolic content [26]. A recently published study conducted by Cuffaro et al [27] investigated the antioxidant effects of the high-value polyphenol oleocanthal and its main metabolites (tyrosol and oleocanthalic acid) in terms of scavenging capacity towards biologically relevant reactive oxygen species (ROS). Remarkably, authors demonstrated that oleocanthal and tyrosol act as ROS scavengers, with a pronounced scavenging capacity towards superoxide anion radical (O2 •− ) and hypochlorous acid (HOCl) [27].…”

“…A recently published study conducted by Cuffaro et al [27] investigated the antioxidant effects of the high-value polyphenol oleocanthal and its main metabolites (tyrosol and oleocanthalic acid) in terms of scavenging capacity towards biologically relevant reactive oxygen species (ROS). Remarkably, authors demonstrated that oleocanthal and tyrosol act as ROS scavengers, with a pronounced scavenging capacity towards superoxide anion radical (O2 •− ) and hypochlorous acid (HOCl) [27]. In addition, authors assessed the permeability of oleocanthal, tyrosol and oleocanthalic acid through the intestine in an intestinal co-culture model composed of Caco-2 and HT29-MTX cell lines, proving that such molecules exhibit a good intestinal permeation capacity (≥50% of intestinal permeation) [27].…”

1-Acetoxypinoresinol, a Lignan from Olives: Insight into Its Characterization, Identification, and Nutraceutical Properties

“…Olives and olive-derived products are valuable sources of natural polyphenols, such as secoiridoids (oleocanthal, oleacein), simple phenols (tyrosol and hydroxytyrosol), flavonoids, and lignans. Secoiridoids are the prominent polyphenols present in olive oil, possessing numerous pharmacological properties and conferring the bitterness, pungency, and astringency of olive oil [14][15][16][17][18]. Within its bioactive compounds, olive oil contains lignans, which are the most recently identified phenolic compounds.…”