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Keywords = phenolipids

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25 pages, 1655 KB  
Review
Hydroxytyrosol Bioavailability: Unraveling Influencing Factors and Optimization Strategies for Dietary Supplements
by Marta Jordán, Natalia García-Acosta, José Luis Espartero, Luis Goya and Raquel Mateos
Nutrients 2025, 17(18), 2937; https://doi.org/10.3390/nu17182937 - 12 Sep 2025
Viewed by 663
Abstract
Hydroxytyrosol (HT) is a major phenolic compound in olives and extra virgin olive oil (EVOO), known for its antioxidant, anti-inflammatory, and cardiometabolic properties. The European Food Safety Authority (EFSA) has approved a health claim for the protection of LDL particles from oxidative damage [...] Read more.
Hydroxytyrosol (HT) is a major phenolic compound in olives and extra virgin olive oil (EVOO), known for its antioxidant, anti-inflammatory, and cardiometabolic properties. The European Food Safety Authority (EFSA) has approved a health claim for the protection of LDL particles from oxidative damage only when HT is consumed within EVOO, which limits its direct use in supplements or functional foods. Since its biological effects depend on absorption, distribution, metabolism, and excretion (ADME), understanding how formulation and delivery strategies influence bioavailability is essential. HT is mainly present as secoiridoid derivatives in EVOO, whereas in supplements, it often appears in its free form, potentially affecting its metabolic fate. This review summarizes human studies on HT bioavailability from EVOO, isolated supplements, and enriched foods, and examines how matrix type, chemical modifications of HT, and advanced delivery systems, such as emulsions, encapsulation, and vesicular carriers, modulate absorption and metabolism. The gut microbiota is highlighted as an emerging factor in HT biotransformation, although its role remains underexplored. Further well-designed human studies are needed to guide the development of nutraceutical formulations capable of replicating the health benefits of EVOO beyond its natural matrix. Full article
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19 pages, 2623 KB  
Article
Phytyl Phenolipids: Structurally Modified Antioxidants with Superior Lipid Membrane Interaction
by Vânia Costa, Marlene Costa, Rute Rebelo, Francisca Arques, Mariana Ferreira, Paula Gameiro, Tomás Barros, Dulce Geraldo, Luís S. Monteiro and Fátima Paiva-Martins
Molecules 2025, 30(10), 2193; https://doi.org/10.3390/molecules30102193 - 17 May 2025
Cited by 1 | Viewed by 672
Abstract
A set of procedures was developed for the simple synthesis of phytyl phenolipids, which resulted in high yields (70–95%) of phytyl esters of caffeic, protocatechuic, homoprotocatechuic, and dihydrocaffeic acids. Initial characterization revealed that these new compounds exhibited similar radical scavenging activity and liposolubility [...] Read more.
A set of procedures was developed for the simple synthesis of phytyl phenolipids, which resulted in high yields (70–95%) of phytyl esters of caffeic, protocatechuic, homoprotocatechuic, and dihydrocaffeic acids. Initial characterization revealed that these new compounds exhibited similar radical scavenging activity and liposolubility to α-tocopherol, a key antioxidant present in membranes. Cyclic voltammetry analysis indicated that the phytyl derivatives had lower anodic peak potentials compared to the original phenolic acids, with electron transfer following an adsorption-controlled mechanism. In phosphatidylcholine large unilamellar vesicles (LUVs), phytyl esters demonstrated remarkable efficiency in preventing liposome autoxidation when compared to α-tocopherol. Despite their strong radical scavenging capacity and membrane penetration ability, the antioxidant effectiveness of the phytyl esters in liposomes was influenced by the structure of their polyphenolic moiety. These new compounds are considered promising candidates for future pharmacological applications against oxidative stress in lipoproteins and cells, warranting further evaluation of their antioxidant and anti-inflammatory effects in cellular models and in vivo. Full article
(This article belongs to the Section Macromolecular Chemistry)
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17 pages, 2050 KB  
Article
Cholesteryl Phenolipids as Potential Biomembrane Antioxidants
by Vânia Costa, Marlene Costa, Francisca Arques, Mariana Ferreira, Paula Gameiro, Dulce Geraldo, Luís S. Monteiro and Fátima Paiva-Martins
Molecules 2024, 29(20), 4959; https://doi.org/10.3390/molecules29204959 - 20 Oct 2024
Cited by 1 | Viewed by 1324
Abstract
The lipophilization of polyphenols (phenolipids) may increase their affinity for membranes, leading to better antioxidant protection. Cholesteryl esters of caffeic, dihydrocaffeic, homoprotocatechuic and protocatechuic acids were synthetized in a one-step procedure with good to excellent yields of ~50–95%. After evaluation of their radical [...] Read more.
The lipophilization of polyphenols (phenolipids) may increase their affinity for membranes, leading to better antioxidant protection. Cholesteryl esters of caffeic, dihydrocaffeic, homoprotocatechuic and protocatechuic acids were synthetized in a one-step procedure with good to excellent yields of ~50–95%. After evaluation of their radical scavenging capacity by the DPPH method and establishing the anodic peak potential by cyclic voltammetry, their antioxidant capacity against AAPH-induced oxidative stress in soybean PC liposomes was determined. Their interaction with the liposomal membrane was studied with the aid of three fluorescence probes located at different depths in the membrane. The cholesteryl esters showed a better or similar radical scavenging capacity to that of α-tocopherol and a lower anodic peak potential than the corresponding parental phenolic acids. Cholesteryl esters were able to protect liposomes to a similar or greater extent than α-tocopherol. However, despite their antiradical capacity and being able to penetrate and orientate in the membrane in a parallel position to phospholipids, the antioxidant efficiency of cholesteryl esters was deeply dependent on the phenolipid polyphenolic moiety structure. When incorporated during liposome preparation, cholesteryl protocatechuate and caffeate showed more than double the activity of α-tocopherol. Thus, cholesteryl phenolipids may protect biomembranes against oxidative stress to a greater extent than α-tocopherol. Full article
(This article belongs to the Special Issue Research Progress of Surfactants)
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22 pages, 3039 KB  
Review
Unlocking the Potential of Hydroxycinnamic Acid Bioconjugates: Tailored Derivatives for Biomedical, Cosmetic, and Food Applications
by José C. J. M. D. S. Menezes and Vinícius R. Campos
Compounds 2024, 4(4), 604-625; https://doi.org/10.3390/compounds4040037 - 10 Oct 2024
Cited by 5 | Viewed by 3135
Abstract
This review discusses the development and applications of bioconjugates derived from natural hydroxycinnamic acids (HCA), such as coumaric, sinapic, ferulic, and caffeic acids, combined with various biomaterials. These bioconjugates offer a range of benefits including antioxidant properties, UV protection, customized hydrophilic–lipophilic balance, improved [...] Read more.
This review discusses the development and applications of bioconjugates derived from natural hydroxycinnamic acids (HCA), such as coumaric, sinapic, ferulic, and caffeic acids, combined with various biomaterials. These bioconjugates offer a range of benefits including antioxidant properties, UV protection, customized hydrophilic–lipophilic balance, improved safety, solubility, emolliency, biocompatibility, biodegradability, and targeted delivery for biomedical, cosmetic, and food applications. The increasing demand for natural products in the biomedical, cosmetic, and food industries has led to the exploration of these hydroxycinnamic acids and their derivatives. We discuss the synthesis and modification of hydroxycinnamic acids with biomaterials such as ω-hydroxy fatty acids, castor and lesquerella oils, glycerol, isosorbides, and synthetic polyethylene glycol to form functional phenolipids for biomedical, sunscreen, and skincare applications. Encapsulation techniques with β-cyclodextrins and modification of polymeric supports like polysaccharides and starch are discussed for enhancing bioavailability and solubility and targeted delivery. The fine-tuned development of bioconjugates from hydroxycinnamic acids using glycerol to modify the hydrophilic–lipophilic balance, substitution by water-soluble carboxylic acid groups, vegetable oil-based phenolipids, polysaccharides, and PEGylation provide enhanced dual functionalities and offer a promising avenue for creating effective products across various applications. Full article
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11 pages, 1463 KB  
Article
Rapid Assessment of Metabolomic Fingerprinting of Recycled Sunflower By-Products via DART-HRMS
by Carmela Zacometti, Anna Lante, Miluska Cisneros, Andrea Massaro, Dasha Mihaylova, Vesela Chalova, Albert Krastanov, Hristo Kalaydzhiev, Giorgia Riuzzi, Alessandra Tata and Severino Segato
Molecules 2024, 29(17), 4092; https://doi.org/10.3390/molecules29174092 - 29 Aug 2024
Cited by 3 | Viewed by 1196
Abstract
To comply with a more circular and environmentally friendly European common agricultural policy, while also valorising sunflower by-products, an ultrasound assisted extraction (UAE) was tested to optimise ethanol-wash solutes (EWS). Furthermore, the capabilities of DART-HRMS as a rapid and cost-effective tool for determining [...] Read more.
To comply with a more circular and environmentally friendly European common agricultural policy, while also valorising sunflower by-products, an ultrasound assisted extraction (UAE) was tested to optimise ethanol-wash solutes (EWS). Furthermore, the capabilities of DART-HRMS as a rapid and cost-effective tool for determining the biochemical changes after valorisation of these defatted sunflower EWS were investigated. Three batches of EWS were doubly processed into optimised EWS (OEWS) samples, which were analysed via DART-HRMS. Then, the metabolic profiles were submitted to a univariate analysis followed by a partial least square discriminant analysis (PLS-DA) allowing the identification of the 15 most informative ions. The assessment of the metabolomic fingerprinting characterising EWS and OEWS resulted in an accurate and well-defined spatial clusterization based on the retrieved pool of informative ions. The outcomes highlighted a significantly higher relative abundance of phenolipid hydroxycinnamoyl-glyceric acid and a lower incidence of free fatty acids and diglycerides due to the ultrasound treatment. These resulting biochemical changes might turn OEWS into a natural antioxidant supplement useful for controlling lipid oxidation and to prolong the shelf-life of foods and feeds. A standardised processing leading to a selective concentration of the desirable bioactive compounds is also advisable. Full article
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18 pages, 2198 KB  
Article
Effect of Alkylresorcinols Isolated from Wheat Bran on the Oxidative Stability of Minced-Meat Models as Related to Storage
by Carolina Cantele, Giulia Potenziani, Ambra Bonciolini, Marta Bertolino and Vladimiro Cardenia
Antioxidants 2024, 13(8), 930; https://doi.org/10.3390/antiox13080930 - 30 Jul 2024
Cited by 3 | Viewed by 1428
Abstract
Due to their antioxidant activity, alkylresorcinols (ARs) extracted from by-products could represent promising natural and innovative antioxidants for the food industry. This study tested the ability of ARs isolated from wheat bran to increase the shelf-life of minced-meat models stored at 4 °C [...] Read more.
Due to their antioxidant activity, alkylresorcinols (ARs) extracted from by-products could represent promising natural and innovative antioxidants for the food industry. This study tested the ability of ARs isolated from wheat bran to increase the shelf-life of minced-meat models stored at 4 °C for 9 days. Fifteen alk(en)ylresorcinols (C17–C25) were recognized by GC/MS, showing good radical-scavenging (200.70 ± 1.33 μmolTE/g extract) and metal-chelating (1.38 ± 0.30 mgEDTAE/g extract) activities. Two ARs concentrations (0.01% and 0.02%) were compared to sodium ascorbate (0.01% and 0.10%) on color (CIELAB values L*, a*, b*, chroma, and hue) and oxidative stability (lipid hydroperoxides, thiobarbituric acid reactive substances (TBARS), and volatile organic compounds (VOCs)) of minced-beef samples. ARs-treated samples were oxidatively more stable than those formulated with sodium ascorbate and the negative control, with significantly lower contents of hydroperoxides and VOCs (hexanal, 1-hexanol, and 1-octen-3-ol) throughout the experiment (p < 0.001). However, no effect on color stability was observed (p > 0.05). Since 0.01% of ARs was equally or more effective than 0.10% sodium ascorbate, those results carry important implications for the food industry, which could reduce antioxidant amounts by ten times and replace synthetic antioxidants with natural ones. Full article
(This article belongs to the Special Issue Phenolic Antioxidants)
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16 pages, 2707 KB  
Article
Enzymatic Modification of Pomace Olive Oil with Natural Antioxidants: Effect on Oxidative Stability
by Renia Fotiadou, Dimitrios Lefas, Despina Vougiouklaki, Aliki Tsakni, Dimitra Houhoula and Haralambos Stamatis
Biomolecules 2023, 13(7), 1034; https://doi.org/10.3390/biom13071034 - 23 Jun 2023
Cited by 8 | Viewed by 2437
Abstract
Enzymatic lipophilization has been proposed as a cost-effective strategy to produce new liposoluble antioxidant compounds. In this study, modified oils rich in structured phenolipids were prepared via one-pot enzymatic acylation of hydroxytyrosol (HTYR), vanillyl alcohol (VA) and homovanillyl alcohol (HVA) with pomace olive [...] Read more.
Enzymatic lipophilization has been proposed as a cost-effective strategy to produce new liposoluble antioxidant compounds. In this study, modified oils rich in structured phenolipids were prepared via one-pot enzymatic acylation of hydroxytyrosol (HTYR), vanillyl alcohol (VA) and homovanillyl alcohol (HVA) with pomace olive oil (POO) in solvent-free conditions using immobilized lipase on biogenic nanoparticles. The effect of temperature (30–70 °C) and enzyme concentration (0.1–1%, w/w) on the efficiency of the bioprocess as well as the reusability of the nanobiocatalyst were thoroughly investigated. The modified oils exhibited increased antioxidant activity compared to the control oil according to DPPH and CUPRAC assays (p < 0.05). The oxidative stability of pomace olive oil was also significantly enhanced after modification, as depicted by the K232 values and TBARS contents under accelerated oxidation at 60 °C (p < 0.05). Moreover, a fortified mayonnaise containing modified oil with HTYR was prepared that was noticeably stable compared to the control mayonnaise at 28 °C for 5 months (p < 0.05). Enzymatically modified oils have great potential for application in the nutraceutical and food industry, encouraging the exploitation of immobilized lipases as effective and green catalytic tools. Full article
(This article belongs to the Topic Antioxidant Activity of Natural Products)
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19 pages, 1215 KB  
Review
Phenolipids, Amphipilic Phenolic Antioxidants with Modified Properties and Their Spectrum of Applications in Development: A Review
by Silvia Ivonne Arzola-Rodríguez, Laila-Nayzzel Muñoz-Castellanos, César López-Camarillo and Erika Salas
Biomolecules 2022, 12(12), 1897; https://doi.org/10.3390/biom12121897 - 17 Dec 2022
Cited by 28 | Viewed by 4547
Abstract
Polyphenols, as secondary metabolites from plants, possess a natural antioxidant capacity and biological activities attributed to their chemical and structural characteristics. Due to their mostly polar character, polyphenols present a low solubility in less polar environments or hydrophobic matrices. However, in order to [...] Read more.
Polyphenols, as secondary metabolites from plants, possess a natural antioxidant capacity and biological activities attributed to their chemical and structural characteristics. Due to their mostly polar character, polyphenols present a low solubility in less polar environments or hydrophobic matrices. However, in order to make polyphenols able to incorporate in oils and fats, a transformation strategy is necessary. For the above, the functionalization of polyphenols through chemical or enzymatic lipophilization has allowed the synthesis of phenolipids. These are amphipilic molecules that preserve the natural phenolic core to which an aliphatic motif is attached by esterification or transesterification reactions. The length of the aliphatic chain in phenolipids allows them to interact with different systems (such as emulsions, oily molecules, micelles and cellular membranes), which would favor their use in processed foods, as vehicles for drugs, antimicrobial agents, antioxidants in the cosmetic industry and even in the treatment of degenerative diseases related to oxidative stress Full article
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14 pages, 3042 KB  
Article
Gastrointestinal Digestion and Microbial Hydrolysis of Alkyl Gallates: Potential Sustained Release of Gallic Acid
by Xinmiao Wang, Qian Wang, Yuanyuan Hu, Fawen Yin, Xiaoyang Liu and Dayong Zhou
Foods 2022, 11(23), 3936; https://doi.org/10.3390/foods11233936 - 6 Dec 2022
Cited by 8 | Viewed by 2616
Abstract
Phenolipids such as alkyl gallates (A-GAs) have been approved by the food industry as non-toxic antioxidant additives, which are also regarded as an emerging source of functional food ingredients. However, comprehensive understanding of their digestive absorption is needed. Thus, the models of live [...] Read more.
Phenolipids such as alkyl gallates (A-GAs) have been approved by the food industry as non-toxic antioxidant additives, which are also regarded as an emerging source of functional food ingredients. However, comprehensive understanding of their digestive absorption is needed. Thus, the models of live mice and anaerobic fermentation were used to clarify the distribution and microbial hydrolysis characteristics of A-GAs in the gastrointestinal tract. HPLC-UV results demonstrated that A-GAs could be hydrolyzed by intestinal lipases and gut microorganisms including Lactobacillus to produce free gallic acid (GA). Through regulating the chain length of the lipid part in A-GAs, the sustained and controllable release of the GA can be easily achieved. Furthermore, A-GAs were also able to reach the colon and the cecum, which would lead to potential gastrointestinal protective effects. Therefore, A-GAs may be applied as possible ingredient for functional foods. Full article
(This article belongs to the Special Issue Advanced Researches on Functional Lipids)
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4 pages, 367 KB  
Proceeding Paper
Structure-Property Influence on the Amphiphilicity of Phenolipids
by Dobrochna Rabiej-Kozioł, Natalia Kryska and Aleksandra Szydłowska-Czerniak
Chem. Proc. 2022, 12(1), 17; https://doi.org/10.3390/ecsoc-26-13533 - 14 Nov 2022
Cited by 1 | Viewed by 1372
Abstract
In recent years, increasing interest has been observed in phenolipids used for enhancing the quality of products containing lipids in the food, pharmaceutical and cosmetic industries. A better understanding of the physicochemical properties of these amphiphilic compounds is crucial to maximizing their antioxidant [...] Read more.
In recent years, increasing interest has been observed in phenolipids used for enhancing the quality of products containing lipids in the food, pharmaceutical and cosmetic industries. A better understanding of the physicochemical properties of these amphiphilic compounds is crucial to maximizing their antioxidant and antiproliferation properties. Therefore, certain p-hydroxycinnamic acid derivatives were synthesized and their lipophilicity expressed as a partition coefficient (Log P) was measured using the shake-flask method. Additionally, the obtained results were compared with the calculated data in ALOGPS 2.1. An increase in lipophilicity was observed along with an increased alkyl chain length. Moreover, hydrophilic/hydrophobic properties are closely related with the number of substituents, especially the hydroxyl group, in aromatic rings. Full article
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16 pages, 3343 KB  
Article
Unexpected Antioxidant Efficiency of Chlorogenic Acid Phenolipids in Fish Oil-in-Water Nanoemulsions: An Example of How Relatively Low Interfacial Concentrations Can Make Antioxidants to Be Inefficient
by Marlene Costa, Sonia Losada-Barreiro, António Vicente, Carlos Bravo-Díaz and Fátima Paiva-Martins
Molecules 2022, 27(3), 861; https://doi.org/10.3390/molecules27030861 - 27 Jan 2022
Cited by 6 | Viewed by 2911
Abstract
Selecting effective antioxidants is challenging since their efficiency in inhibiting lipid oxidation depends on the rate constants of the chemical reactions involved and their concentration at the reaction site, i.e., at the interfacial region. Accumulation of antioxidants at the interface of emulsions is [...] Read more.
Selecting effective antioxidants is challenging since their efficiency in inhibiting lipid oxidation depends on the rate constants of the chemical reactions involved and their concentration at the reaction site, i.e., at the interfacial region. Accumulation of antioxidants at the interface of emulsions is key to modulate their efficiency in inhibiting lipid oxidation but its control was not well understood, especially in emulsions. It can be optimized by modifying the physicochemical properties of antioxidants or the environmental conditions. In this work, we analyze the effects of surfactant concentration, droplet size, and oil to water ratio on the effective interfacial concentration of a set of chlorogenic acid (CGA) esters in fish oil-in-water (O/W) emulsions and nanoemulsions and on their antioxidant efficiency. A well-established pseudophase kinetic model is used to determine in the intact emulsified systems the effective concentrations of the antioxidants (AOs). The relative oxidative stability of the emulsions is assessed by monitoring the formation of primary oxidation products with time. Results show that the concentration of all AOs at the interfacial region is much higher (20–90 fold) than the stoichiometric one but is much lower than those of other phenolipid series such as caffeic or hydroxytyrosol derivatives. The main parameter controlling the interfacial concentration of antioxidants is the surfactant volume fraction, ΦI, followed by the O/W ratio. Changes in the droplet sizes (emulsions and nanoemulsions) have no influence on the interfacial concentrations. Despite the high radical scavenging capacity of CGA derivatives and their being concentrated at the interfacial region, the investigated AOs do not show a significant effect in inhibiting lipid oxidation in contrast with what is observed using other series of homologous antioxidants with similar reactivity. Results are tentatively interpreted in terms of the relatively low interfacial concentrations of the antioxidants, which may not be high enough to make the rate of the inhibition reaction faster than the rate of radical propagation. Full article
(This article belongs to the Special Issue Antioxidants in Multiphase Systems)
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5 pages, 233 KB  
Proceeding Paper
Bioavailability of Rapeseed Oil Fortified with Ethyl Sinapate
by Dobrochna Rabiej-Kozioł, Marek P. Krzemiński, Iwona Wiśniewska and Aleksandra Szydłowska-Czerniak
Chem. Proc. 2022, 8(1), 26; https://doi.org/10.3390/ecsoc-25-11725 - 14 Nov 2021
Viewed by 1147
Abstract
In recent years, phenolic acid esters have been proposed as valuable additives in the food and cosmetic industries. Therefore, ethyl sinapate (ESA) was synthesized using an enzymatic approach. Hence, the bioaccessibility of antioxidant compounds after the in vitro digestion process of rapeseed oil [...] Read more.
In recent years, phenolic acid esters have been proposed as valuable additives in the food and cosmetic industries. Therefore, ethyl sinapate (ESA) was synthesized using an enzymatic approach. Hence, the bioaccessibility of antioxidant compounds after the in vitro digestion process of rapeseed oil fortified with ESA was evaluated. The antioxidant activity (AA) of the oil samples before and after digestion was analyzed using three spectrophotometric methods. The addition of synthesized ESA at concentrations of 0.02 and 0.5% caused a two- to ten-fold increase in the AA of the rapeseed oils. Therefore, the obtained phenolipid can be used as an efficient antioxidant in the oil industry. Full article
12 pages, 2329 KB  
Article
Identification of Tyrosyl Oleate as a Novel Olive Oil Lipophenol with Proliferative and Antioxidant Properties in Human Keratinocytes
by Cinzia Benincasa, Chiara La Torre, Alessia Fazio, Enzo Perri, Maria Cristina Caroleo, Pierluigi Plastina and Erika Cione
Antioxidants 2021, 10(7), 1051; https://doi.org/10.3390/antiox10071051 - 29 Jun 2021
Cited by 14 | Viewed by 4126
Abstract
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Lipophilic Derivative as Antioxidants)
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16 pages, 4489 KB  
Article
Effects of the Reactive Moiety of Phenolipids on Their Antioxidant Efficiency in Model Emulsified Systems
by Marlene Costa, Sonia Losada-Barreiro, Júlia Magalhães, Luís S. Monteiro, Carlos Bravo-Díaz and Fátima Paiva-Martins
Foods 2021, 10(5), 1028; https://doi.org/10.3390/foods10051028 - 10 May 2021
Cited by 9 | Viewed by 2606
Abstract
Our previous research was focused on the effects of hydrophobicity on the antioxidant (AO) efficiency of series of homologous antioxidants with the same reactive moieties. In this work we evaluate the antioxidant efficiency of hydrophobic phenolipids in 4:6 olive oil-in-water emulsions, with different [...] Read more.
Our previous research was focused on the effects of hydrophobicity on the antioxidant (AO) efficiency of series of homologous antioxidants with the same reactive moieties. In this work we evaluate the antioxidant efficiency of hydrophobic phenolipids in 4:6 olive oil-in-water emulsions, with different phenolic moieties (derived from caffeic, 4-hydroxycinnamic, dihydrocaffeic acids, tyrosol and hydroxytyrosol), with alkyl chains of 8 and 16 carbons, and compare the antioxidant efficiency with that of the parent compounds. All catecholic phenolipids, in particular the C8 derivatives, have proven to be better antioxidants for the oxidative protection of emulsions than their parental compounds with octyl dihydrocafffeate being the most efficient (16-fold increase in relation to the control). To understand the importance of some factors on the antioxidant efficiency of compounds in emulsions, Pearson’s correlation analysis was carried out between antioxidant activity and the first anodic potential (Epa), reducing capacity (FRAP value), DPPH radical scavenging activity (EC50) and the concentration of antioxidants in each region of the emulsified system. Results confirm the importance of the effective concentration of AOs in the interfacial region (AOI) (ρ = 0.820) and of the Epa (ρ = −0.677) in predicting their antioxidant efficiency in olive oil-in-water emulsions. Full article
(This article belongs to the Special Issue Study on Stability and Lipid Oxidation Inhibition in Emulsified Food)
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23 pages, 3061 KB  
Article
Bis-allylic Deuterated DHA Alleviates Oxidative Stress in Retinal Epithelial Cells
by Mélissa Rosell, Martin Giera, Philippe Brabet, Mikhail S. Shchepinov, Michel Guichardant, Thierry Durand, Joseph Vercauteren, Jean-Marie Galano and Céline Crauste
Antioxidants 2019, 8(10), 447; https://doi.org/10.3390/antiox8100447 - 1 Oct 2019
Cited by 13 | Viewed by 5672
Abstract
Oxidative stress plays a crucial role in developing and accelerating retinal diseases including age-related macular degeneration (AMD). Docosahexaenoic acid (DHA, C22:6, n-3), the main lipid constituent of retinal epithelial cell membranes, is highly prone to radical and enzymatic oxidation leading to deleterious or [...] Read more.
Oxidative stress plays a crucial role in developing and accelerating retinal diseases including age-related macular degeneration (AMD). Docosahexaenoic acid (DHA, C22:6, n-3), the main lipid constituent of retinal epithelial cell membranes, is highly prone to radical and enzymatic oxidation leading to deleterious or beneficial metabolites for retinal tissue. To inhibit radical oxidation while preserving enzymatic metabolism, deuterium was incorporated at specific positions of DHA, resulting in D2-DHA when incorporated at position 6 and D4-DHA when incorporated at the 6,9 bis-allylic positions. Both derivatives were able to decrease DHAs’ toxicity and free radical processes involved in lipid peroxidation, in ARPE-19 cells (Adult Retinal Pigment Epithelial cell line), under pro-oxidant conditions. Our positive results encouraged us to prepare lipophenolic-deuterated-DHA conjugates as possible drug candidates for AMD treatment. These novel derivatives proved efficient in limiting lipid peroxidation in ARPE-19 cells. Finally, we evaluated the underlying mechanisms and the enzymatic conversion of both deuterated DHA. While radical abstraction was affected at the deuterium incorporation sites, enzymatic conversion by the lipoxygenase 15s-LOX was not impacted. Our results suggest that site-specifically deuterated DHA could be used in the development of DHA conjugates for treatment of oxidative stress driven diseases, or as biological tools to study the roles, activities and mechanisms of DHA metabolites. Full article
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