Recently, we identified hydroxytyrosyl oleate (HtyOle) in the by-products of olive oil, pomace and olive mill waste water (OMWW). Herein, we report that HtyOle is more accurately quantified by extracting the phenolic fraction from both matrices by using aqueous methanol (80%). By applying this method, HtyOle was also detected in extra virgin olive oil (EVOO). Since olive oil is used in the preparation of many cosmetic formulations, we explored the antioxidant capacity of HtyOle in human keratinocytes. Formation of reactive oxygen species (ROS) and malondialdehyde (MDA), as well as activity of Glutathione-S-transferase (GST) and superoxide dismutase (SOD) were decreased by HtyOle. In addition to that, microRNAs (miRs) involved in both redox status balance and skin regeneration potential were also tested. The following miRs, hsa-miR-21 and hsa-miR-29a, were increased while has-miR-34a was not affected by HtyOle.
Olive tree (Olea europaea L.) leaf, a waste by-product of the olive oil industry, is an inexpensive and abundant source of biophenols of great interest for various industrial applications in the food supplement, cosmetic, and pharmaceutical industries. In this work, the aqueous extraction of high-added value compounds from olive leaves by using microfiltered (MF), ultrapure (U), and osmosis-treated (O) water was investigated. The extraction of target compounds, including oleuropein (Olp), hydroxytyrosol (HyTyr), tyrosol (Tyr), verbascoside (Ver), lutein (Lut), and rutin (Rut), was significantly affected by the characteristics of the water used. Indeed, according to the results of liquid chromatography tandem mass spectrometry, the extracting power of microfiltered water towards rutin resulted very poor, while a moderate extraction was observed for oleuropein, verbascoside, and lutein. On the other hand, high concentrations of hydroxytyrosol were detected in the aqueous extracts produced with microfiltered water. The extraction power of ultrapure and osmosis-treated water proved to be very similar for the bio-active compounds oleuropein, verbascoside, lutein, and rutin. The results clearly provide evidence of the possibility of devising new eco-friendly strategies based on the use of green solvents which can be applied to recover bioactive compounds from olive leaves.
Lipophenols are an emerging subclass of phenolic compounds characterized by the presence of a lipid moiety. Recently, hydroxytyrosyl oleate (HtyOle), a derivative of hydroxytyrosol, has been identified in olive oil and by-products. Furthermore, HtyOle possesses anti-inflammatory, antioxidant, and tissue regenerating properties. In this work, the potential occurrence of tyrosyl oleate (TyOle) in olive oil was investigated based on the hypothesis that its precursors tyrosol and oleic acid, both present in relatively high amount can be coupled together. Moreover, TyOle effects have been investigated in human keratinocytes to verify its proliferative and antioxidant properties. The quantitative determination of TyOle was carried out by the external standard method in liquid chromatography coupled with mass spectrometry (LC/MS), in negative mode using multiple reaction monitoring (MRM). The proliferative properties of TyOle on immortalized human keratinocytes (HaCat) were evaluated by 3-(4,5-dimethylthiasol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Morphological changes were observed by fluorescent staining with phalloidin (for F-actin) or 4,6-diamidino-2-phenylindole (DAPI, for chromatin) dye. The antioxidant activity was assessed at the level of production of mitochondrial reactive oxygen species (ROS) induced with UV exposure. TyOle was identified in all the oil samples investigated. Interestingly, TyOle concentration was higher in defective or low-quality oils than in extra virgin oils. The formation of TyOle likely occurs during the crushing and kneading processes and its concentration is related to the increase of rancidity and of the concentration of free precursors. Herein we show that TyOle induced an increase in the viability of HaCat cells and cytoskeletal remodeling.
Date palm (Phoenix dactylifera L.) trees are largely cultivated across the Algerian oases; they are principal sources of remuneration and the economic basis for residents of these areas. Date palm fruits are rich sources of essential nutrients, vitamins, minerals, and dietary fibers, with many potential health benefits, yet there are few studies on the chemical composition and biological properties of date palm seed oil. In this study, we present an in-depth characterization of the biochemical composition and antioxidant properties of date palm seed oil (DPSO) produced in Algeria. DPSOs of eight Algerian cultivars, Arechti, Degla-Baida, Deglet-Nour, Ghars, Haloua, Itima, Mech-Degla, and Tentbouchet, were investigated to determine their biochemical compositions and antioxidant properties. The results highlight the potential of DPSO as an alternative food and a natural resource, thanks to several important compounds having high antioxidant capacity. In particular, fatty acids and triacylglycerol (TAGs) analyses showed that oleic (42.74–50.19%), lauric (18.40–22.2%), and myristic (8.83–10.17%) were the major fatty acids, while 1-myristoyl 2-oleoyl 3-linoleoyl glycerol, 1-linolenoyl 2-oleoyl 3-linoleoyl glycerol, 1-2-linolenoyl 3-linoleoyl glycerol, and 1-linolenoyl 2-myristoyl 3-linoleoyl glycerol were the major TAGs. Biophenols and tocopherols analyses revealed the presence of important compounds, such as catechin (22.04–24.92 mg/kg), vanillin (10.67–23.98 mg/kg), and α-tocopherol (443.59 mg/kg), at high remarkable levels. Therefore, a comparison with the literature data concerning other seed oils, including olive oil, confirms that DPSO can be considered a high-quality oil, from a biochemical and biological point of view.
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