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Antioxidants
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Lipophilic Derivative as Antioxidants
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Lipophilic Derivative as Antioxidants

A special issue of Antioxidants (ISSN 2076-3921). This special issue belongs to the section "Natural and Synthetic Antioxidants".

Deadline for manuscript submissions: closed (30 April 2021) | Viewed by 26390

Special Issue Editors

Prof. Dr. Pierluigi Stipa

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Guest Editor
Department S.I.M.A.U.–Chemistry Division, Università Politecnica delle Marche, Via Brecce Bianche, 60131 Ancona, Italy
Interests: antioxidants; free radicals; nitroxide radicals; spin trapping; electron paramagnetic resonance (EPR); DFT calculations
Prof. Dr. Giovanna Mobbili

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Guest Editor
Department of Life and Environmental Sciences, Università Politecnica delle Marche, via Brecce Bianche, 60131 Ancona, Italy
Interests: antioxidants; drug delivery; organic synthesis; liposomes; nanocomposites; dynamic light scattering
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Antioxidants play a crucial role in the prevention and treatment of many diseases by reducing the concentration of species involved in oxidative stress, such as free radicals and reactive oxygen, as well as nitrogen species (ROS, NOS), originating from various environmental stimuli or during normal cellular metabolism. When an unbalance between the activity of these species and the fighting ability of the antioxidant system occurs, exogenous antioxidants could represent a promising therapeutic approach in many inflammatory and/or degenerative processes, including neurodegenerative and cardiovascular diseases, skin cancer, chronic inflammatory disorders, and several retinal degenerative diseases. However, some physicochemical properties of exogenous antioxidants can limit their diffusion in specific biological compartments, hence invalidating their efficacy. In this context, in order to modulate their distribution, the use of suitable formulations, as well as the modification of the structure of natural antioxidants, represents an interesting approach. In this Special Issue of Antioxidants, expert researchers are invited to present original papers or review articles considering any advances in lipophilic derivatives as antioxidants.

Potential topics include, without being limited to, the following:

  • Lipophilization of natural antioxidants with the introduction of long alkyl chain or fluorine atoms by covalent bonds;
  • Structure–activity relationships (SARs) for the design of compounds with antioxidant properties;
  • Synthesis of new endogenous-like derivatives as possible antioxidants;
  • Studies of the antioxidant mechanisms of lipophilic derivatives, experimentally as well as by computational methods;
  • In silico studies of the inhibitory effect of enzymes potentially generating ROS;
  • Employment of lipophilic antioxidant derivatives in nanostructured lipid nanocarriers.

Submissions of manuscripts from different fields of research are strongly encouraged.

Prof. Dr. Pierluigi Stipa
Dr. Giovanna Mobbili
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Antioxidants is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2900 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Antioxidants
  • Lipophilization
  • Chemical modification
  • Oxidative stress
  • Free radicals
  • Reactive oxygen species (ROS)
  • Reactive nitrogen species (NOS)

Published Papers (7 papers)

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Research

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13 pages, 2247 KiB  
Article
Identification and Antioxidant Abilities of Enzymatic-Transesterification (−)-Epigallocatechin-3-O-gallate Stearyl Derivatives in Non-Aqueous Systems
by Chengyu Jiang, Li Wang, Xin Huang, Song Zhu, Chaoyang Ma and Hongxin Wang
Antioxidants 2021, 10(8), 1282; https://doi.org/10.3390/antiox10081282 - 13 Aug 2021
Cited by 10 | Viewed by 2272
Abstract
Vinyl stearate was added to enzymatic transesterification of (−)-Epigallocatechin-3-O-gallate (EGCG) to enhance its lipophilicity and antioxidant ability in a non-aqueous system. The lipase DF “Amano” 15 was used as the catalyst. The optimal reaction conditions were: acetonitrile as the solvent, the [...] Read more.
Vinyl stearate was added to enzymatic transesterification of (−)-Epigallocatechin-3-O-gallate (EGCG) to enhance its lipophilicity and antioxidant ability in a non-aqueous system. The lipase DF “Amano” 15 was used as the catalyst. The optimal reaction conditions were: acetonitrile as the solvent, the molar ratio of vinyl stearate: EGCG as 3:1, an enzyme amount of 4.0% (ratio of substrate mass), and a reaction temperature and time of 50 °C and 96 h, respectively, achieving 65.2% EGCG conversion. HPLC–MS and NMR were used to determine the structure of EGCG stearyl derivative (3″,5″-2-O-stearyl-EGCG). The lipophilicity of EGCG stearyl derivatives (3.49 ± 0.34) was higher (5.06 times) than that of the parent EGCG (0.69 ± 0.08). Furthermore, EGCG stearyl derivatives had excellent lipid oxidation compared with BHT, BHA, and parent EGCG. The POVs of soybean oil with EGCG stearyl derivatives (18.17 ± 0.92 mEq/kg) were significantly reduced (by 62.5%) at 21 d compared with those of EGCG (48.50 ± 1.23 mEq/kg). These results indicate that EGCG derivatives have broad antioxidant application prospects in lipophilic environments/high-fat food. Full article
(This article belongs to the Special Issue Lipophilic Derivative as Antioxidants)
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10 pages, 1383 KiB  
Article
Amidinoquinoxaline-Based Nitrones as Lipophilic Antioxidants
by Nadia Gruber, Liliana Orelli, Cristina Minnelli, Luca Mangano, Emiliano Laudadio, Giovanna Mobbili and Pierluigi Stipa
Antioxidants 2021, 10(8), 1185; https://doi.org/10.3390/antiox10081185 - 26 Jul 2021
Cited by 3 | Viewed by 1712
Abstract
The potential of nitrones (N-oxides) as therapeutic antioxidants is due to their ability to counteract oxidative stress, mainly attributed to their action as radical scavengers toward C- and O-centered radicals. Among them, nitrones from the amidinoquinoxaline series resulted in interesting derivatives, due to [...] Read more.
The potential of nitrones (N-oxides) as therapeutic antioxidants is due to their ability to counteract oxidative stress, mainly attributed to their action as radical scavengers toward C- and O-centered radicals. Among them, nitrones from the amidinoquinoxaline series resulted in interesting derivatives, due to the ease with which it is possible to introduce proper substituents within their structure in order to modulate their lipophilicity. The goal is to obtain lipophilic antioxidants that are able to interact with cell membranes and, at the same time, enough hydrophilic to neutralize those radicals present in a water compartment. In this work, the antioxidant efficacy of a series of amidinoquinoxaline nitrones has been evaluated regarding the oxidation of 2-deoxyribose and lipid peroxidation. The results have been rationalized on the basis of the different possible mechanisms involved, depending on some of their properties, such as lipophilicity, the ability to scavenge free radicals, and to undergo single electron transfer (SET) reactions. Full article
(This article belongs to the Special Issue Lipophilic Derivative as Antioxidants)
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12 pages, 2329 KiB  
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 8 | Viewed by 2908
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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23 pages, 12566 KiB  
Article
Improving the Antioxidant Properties of Calophyllum inophyllum Seed Oil from French Polynesia: Development and Biological Applications of Resinous Ethanol-Soluble Extracts
by Mathieu Cassien, Anne Mercier, Sophie Thétiot-Laurent, Marcel Culcasi, Emilie Ricquebourg, Alice Asteian, Gaëtan Herbette, Jean-Pierre Bianchini, Phila Raharivelomanana and Sylvia Pietri
Antioxidants 2021, 10(2), 199; https://doi.org/10.3390/antiox10020199 - 30 Jan 2021
Cited by 17 | Viewed by 5350
Abstract
Tamanu oil from Calophyllum inophyllum L. has long been used in traditional medicine. Ethanol extraction was found the best strategy for recovering bioactive compounds from the resin part of Tamanu oil, yielding two neutral and acidic resins fractions with high phenolics, flavonoids and [...] Read more.
Tamanu oil from Calophyllum inophyllum L. has long been used in traditional medicine. Ethanol extraction was found the best strategy for recovering bioactive compounds from the resin part of Tamanu oil, yielding two neutral and acidic resins fractions with high phenolics, flavonoids and pyranocoumarins concentrations. A further cascade of LPLC/HPLC separations of neutral and acidic resin fractions allowed identifying fifteen metabolites, and among them, calanolide D and 12-oxocalanolide A (both in neutral fraction) were first identified from a natural source. All these extracts, subfractions and isolated metabolites demonstrated increased free radical scavenging, antioxidant, anti-inflammatory, antimicrobial and antimycobacterial activity compared to Tamanu oil and its de-resinated lipid phase. Overall, these results could promote resinous ethanol-soluble Tamanu oil extracts as a useful multifaceted and renewable medicinal resource. Full article
(This article belongs to the Special Issue Lipophilic Derivative as Antioxidants)
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27 pages, 2085 KiB  
Article
Positive Associations of Dietary Intake and Plasma Concentrations of Vitamin E with Skeletal Muscle Mass, Heel Bone Ultrasound Attenuation and Fracture Risk in the EPIC-Norfolk Cohort
by Angela A. Mulligan, Richard P. G. Hayhoe, Robert N. Luben and Ailsa A. Welch
Antioxidants 2021, 10(2), 159; https://doi.org/10.3390/antiox10020159 - 22 Jan 2021
Cited by 11 | Viewed by 3121
Abstract
The prevalence of sarcopenia, frailty and fractures is increasing. Prevention options are limited, but dietary factors including vitamin E have the potential to confer some protection. This study investigated cross-sectional associations between dietary and plasma concentrations of vitamin E with indices of skeletal [...] Read more.
The prevalence of sarcopenia, frailty and fractures is increasing. Prevention options are limited, but dietary factors including vitamin E have the potential to confer some protection. This study investigated cross-sectional associations between dietary and plasma concentrations of vitamin E with indices of skeletal muscle mass (SMM) (n = 14,179 and 4283, respectively) and bone density (n = 14,694 and 4457, respectively) and longitudinal fracture risk (n = 25,223 and 7291, respectively) in European Prospective Investigation Into Cancer and Nutrition (EPIC)-Norfolk participants, aged 39–79 years at baseline. Participants completed a health and lifestyle questionnaire, a 7-day diet diary (7dDD) and had anthropometric measurements taken. Fat-free mass (as a SMM proxy) was measured using bioimpedance and bone density was measured using calcaneal broadband ultrasound attenuation (BUA) and incident fractures over 18.5 years of follow-up. Associations between indices of SMM, BUA and fracture risk were investigated by quintiles of dietary vitamin E intake or plasma concentrations. Positive trends in SMM indices and BUA were apparent across dietary quintiles for both sexes, with interquintile differences of 0.88–1.91% (p < 0.001), and protective trends for total and hip fracture risk. Circulating plasma α- and γ-tocopherol results matched the overall dietary findings. Dietary vitamin E may be important for musculoskeletal health but further investigation is required to fully understand the relationships of plasma tocopherols. Full article
(This article belongs to the Special Issue Lipophilic Derivative as Antioxidants)
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Review

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39 pages, 7417 KiB  
Review
Recent Advances on Nanoparticle Based Strategies for Improving Carotenoid Stability and Biological Activity
by Kandi Sridhar, Baskaran Stephen Inbaraj and Bing-Huei Chen
Antioxidants 2021, 10(5), 713; https://doi.org/10.3390/antiox10050713 - 30 Apr 2021
Cited by 23 | Viewed by 4991
Abstract
Carotenoids are natural pigments widely used in food industries due to their health-promoting properties. However, the presence of long-chain conjugated double bonds are responsible for chemical instability, poor water solubility, low bioavailability and high susceptibility to oxidation. The application of a nanoencapsulation technique [...] Read more.
Carotenoids are natural pigments widely used in food industries due to their health-promoting properties. However, the presence of long-chain conjugated double bonds are responsible for chemical instability, poor water solubility, low bioavailability and high susceptibility to oxidation. The application of a nanoencapsulation technique has thus become a vital means to enhance stability of carotenoids under physiological conditions due to their small particle size, high aqueous solubility and improved bioavailability. This review intends to overview the advances in preparation, characterization, biocompatibility and application of nanocarotenoids reported in research/review papers published in peer-reviewed journals over the last five years. More specifically, nanocarotenoids were prepared from both carotenoid extracts and standards by employing various preparation techniques to yield different nanostructures including nanoemulsions, nanoliposomes, polymeric/biopolymeric nanoparticles, solid lipid nanoparticles, nanostructured lipid nanoparticles, supercritical fluid-based nanoparticles and metal/metal oxide nanoparticles. Stability studies involved evaluation of physical stability and/or chemical stability under different storage conditions and heating temperatures for varied lengths of time, while the release behavior and bioaccessibility were determined by various in vitro digestion and absorption models as well as bioavailability through elucidating pharmacokinetics in an animal model. Moreover, application of nanocarotenoids for various biological applications including antioxidant, anticancer, antibacterial, antiaging, cosmetics, diabetic wound healing and hepatic steatosis were summarized. Full article
(This article belongs to the Special Issue Lipophilic Derivative as Antioxidants)
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20 pages, 843 KiB  
Review
The Multifaced Actions of Curcumin in Pregnancy Outcome
by Giovanni Tossetta, Sonia Fantone, Stefano Raffaele Giannubilo and Daniela Marzioni
Antioxidants 2021, 10(1), 126; https://doi.org/10.3390/antiox10010126 - 17 Jan 2021
Cited by 41 | Viewed by 4946
Abstract
Curcumin, also known as diferuloylmethane, is the main polyphenolic substance present in the rhizomes of Curcuma longa L. This plant showed many beneficial effects and has been used since ancient times for both food and pharmaceutical purposes. Due to its pleiotropic functions, [...] Read more.
Curcumin, also known as diferuloylmethane, is the main polyphenolic substance present in the rhizomes of Curcuma longa L. This plant showed many beneficial effects and has been used since ancient times for both food and pharmaceutical purposes. Due to its pleiotropic functions, curcumin consumption in the human diet has become very common thanks also to the fact that this natural compound is considered quite safe as it does not have serious side effects. Its functions as an anti-inflammatory, anti-oxidant, neuroprotective, immunomodulatory, anti-toxicant, anti-apoptotic, and anti-diabetic compound are already known and widely demonstrated. There are numerous studies concerning its effects on various human pathologies including cancer, diabetes and arthritis while the studies on curcumin during pregnancy have been performed only in animal models. Data concerning the role of curcumin as anti-inflammatory compound suggest a possible use of curcumin in managing pregnancy complications such as Preeclampsia (PE), Gestational Diabetes Mellitus (GDM), Fetal Growth Restriction (FGR), PreTerm Birth (PTB), and exposure to toxic agents and pathogens. The aim of this review is to present data to support the possible use of curcumin in clinical trials on human gestation complications. Full article
(This article belongs to the Special Issue Lipophilic Derivative as Antioxidants)
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