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A special issue of Antioxidants (ISSN 2076-3921). This special issue belongs to the section "Extraction and Industrial Applications of Antioxidants".

Deadline for manuscript submissions: 30 November 2024 | Viewed by 10439

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Dr. Adriano Costa de Camargo

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Nutrition and Food Technology Institute, University of Chile, Santiago 7830490, Chile
Interests: food chemistry; functional foods; nutraceuticals; lipids; phenolics; non-communicable diseases; food irradiation; ultrasound; oxidative stress; antioxidants
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Prof. Dr. Fereidoon Shahidi

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Guest Editor

Department of Biochemistry, Memorial University of Newfoundland, St. John’s, NL A1C 5S7, Canada
Interests: antioxidants; radical scavenging; phenolic and polyphenolic compounds; oxidation control; disease risk reduction; bioactivity; health benefits; action mechanism
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Phenolic compounds include tocopherols and tocotrienols, collectively known as tocols, with vitamin E activity, as well as secondary plant metabolites (i.e., phenolic acids, flavonoids, stilbenes, coumarins, lignans, and tannins). Phenolic compounds protect plants and plant foods from biotic and abiotic oxidative stress as well as herbivory. This property is therefore important until the post-harvest time. From the food processing standpoint, lipid oxidation is a most important deterioration problem faced by the food industry. The consequence of lipid oxidation is noted mainly by the negative changes found in terms of nutritional quality, food safety, and sensory characteristics of food. Therefore, natural antioxidants are also crucial ingredients employed by the food industry to decrease and/or prevent lipid oxidation. However, phenolic compounds are not only good for plant health, but also render a myriad of other bioactivities. The health benefits of phenolic compounds, in vitro and in vivo, are supported by both epidemiological and animal and human studies. Phenolics may act as free radical terminators, metal chelators, but their antioxidant properties are also important to overcome inflammatory responses caused by different factors including exposure to xenobiotics and pathogenic microorganisms.

This Special Issue invites contributions addressing the antioxidant properties of phenolic compounds in plants, plant foods, and by-products thereof as well as their metabolites and derivatives. Original articles or review papers focusing on phenolic antioxidants and their impact on agronomical/plant science, food science, nutrition and health will be considered.

Dr. Adriano Costa de Camargo
Prof. Dr. Fereidoon Shahidi
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.

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Published Papers (10 papers)

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Research

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12 pages, 1039 KiB

Open AccessArticle

Cold-Pressed Aristotelia chilensis (Mol.) Stuntz Seed Oil Prevents Metabolic-Dysfunction-Associated Steatotic Liver Disease (MASLD) in a High-Fat-Diet-Induced Obesity Murine Model

by Benjamín Claria, Alejandra Espinosa, Alicia Rodríguez, Gretel Dovale-Rosabal, José Luis Bucarey, María Elsa Pando, Nalda Romero, Francisca Reinoso, Camila Sánchez, Rodrigo Valenzuela, Carolina H. Ribeiro and Santiago P. Aubourg

Antioxidants 2024, 13(11), 1384; https://doi.org/10.3390/antiox13111384 - 13 Nov 2024

Viewed by 417

Abstract

This study evaluated the effects of cold-pressed maqui (Aristotelia chilensis (Mol.) Stuntz) seed oil (MO) on liver metabolism and biochemical markers in a high-fat diet (HFD) murine model. In it, the fatty acid profile, tocopherol and tocotrienol contents, and antioxidant capacity of MO were analyzed. Male C57BL/6 mice were divided into four groups (i.e., a, b, c, and d groups) and supplemented for 12 weeks according to the following distribution: (a) control diet (CD)-sunflower oil (SO), (b) CD+MO, (c) HFD+SO, and (d) HFD+MO. Total body and organ weights, serum markers, and liver fat infiltration were assessed. MO contained 32.31% oleic acid, 46.41% linoleic acid, and 10.83% α-linolenic acid; additionally, α- and γ-tocopherol levels were 339.09 ± 5.15 and 135.52 ± 38.03 mg/kg, respectively, while β-, δ-tocopherol, and α-tocotrienol were present in trace amounts and the antioxidant capacity measured was 6.66 ± 0.19 μmol Trolox equivalent/g. MO supplementation significantly reduced the visceral fat (0.76 ± 0.06 g vs. 1.32 ± 0.04 g) and GPT (glutamate pyruvate transaminase) levels (71.8 ± 5.0 vs. 35.2 ± 2.6 U/L), and the liver fat infiltration score (6 vs. 3) in the HFD+MO group compared to HFD+SO. It is suggested that MO may effectively prevent fatty liver disease, warranting further research on its potential benefits for human health. Full article

(This article belongs to the Special Issue Phenolic Antioxidants)

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15 pages, 1289 KiB

Open AccessArticle

Facile One-Pot Conversion of (poly)phenols to Diverse (hetero)aryl Compounds by Suzuki Coupling Reaction: A Modified Approach for the Synthesis of Coumarin- and Equol-Based Compounds as Potential Antioxidants

by Muthipeedika Nibin Joy, Igor S. Kovalev, Olga V. Shabunina, Sougata Santra and Grigory V. Zyryanov

Antioxidants 2024, 13(10), 1198; https://doi.org/10.3390/antiox13101198 - 3 Oct 2024

Viewed by 590

Abstract

A series of 16 (hetero)aryl compounds based on coumarin and equol has been efficiently synthesized by exploring the palladium-catalyzed Suzuki cross-coupling reactions. Polyphenol based on coumarin (4-methyl-7-hydroxy coumarin) was initially converted to corresponding coumarin imidazylate and then subjected to Suzuki coupling reaction with 4-methoxyphenylboronic acid to obtain the coupled product. This modified approach was later developed into a one-pot methodology by directly reacting the polyphenol with 1,1-sulfonyldiimidazole (SDI) and boronic acid in situ to obtain the Suzuki coupled product in one step. Moreover, an array of (poly)phenols based on coumarin and equol were later converted to diverse (hetero)aryl compounds by this optimized step-economic protocol. The synthesized compounds were then subjected to the screening of their potential antioxidant activities by 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. In our investigation, the compounds 4ah, 4eh, 4gh and 4hh exhibited promising antioxidant potential when compared to the reference standard, butylated hydroxytoluene (BHT). Structure activity relationship (SAR) studies revealed the importance of the presence of electron-donating substituents in enhancing the antioxidant activity of the synthesized compounds. Full article

(This article belongs to the Special Issue Phenolic Antioxidants)

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13 pages, 3181 KiB

Open AccessArticle

Comparative Study of Flavonoid Profiles, Antioxidant, and Antiproliferative Activities in Hot-Air and Vacuum Drying of Different Parts of Pitaya (Hylocereus undatus Britt) Flowers

by Caifeng Shi, Huaqian Long, Jia Hu and Xinbo Guo

Antioxidants 2024, 13(8), 956; https://doi.org/10.3390/antiox13080956 - 7 Aug 2024

Viewed by 904

Abstract

Pitaya flower, a medicinal and edible plant commonly used in tropical and subtropical regions, was the focus of this study, which compared the effects of hot-air drying (HAD) and vacuum drying (VD) on phytochemical profiles and biological activities of its four parts: calyx, petals, stamens, and pistils. Both drying methods significantly increased the total phenolic content (TPC) of pitaya flowers, with values ranging from 1.86 to 3.24 times higher than those of fresh samples. Twelve flavonoid compounds were identified in pitaya flowers, with the glycoside derivatives of three flavonols (kaempferol, isorhamnetin, and quercetin) being the most abundant. VD resulted in 1.15 times higher total flavonoid glycoside content than HAD, whereas in petals, HAD yielded a total flavonoid glycoside content 1.21 times higher than VD. Both HAD and VD effectively increased the antioxidant capacities of pitaya flowers, though the difference between the two methods was not significant. Additionally, both drying methods enhanced the antiproliferative activity of pitaya flowers, with HAD showing a more significant effect than VD. The present study emphasized the efficacy of drying methods for enhancing flavonoids in pitaya flowers and provided insights for functional products’ innovation with different parts of pitaya flowers. Full article

(This article belongs to the Special Issue Phenolic Antioxidants)

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23 pages, 6407 KiB

Open AccessArticle

Synthesis, Cytotoxicity and Antioxidant Activity Evaluation of Some Thiazolyl–Catechol Compounds

by Alexandra Cătălina Cornea, Gabriel Marc, Ioana Ionuț, Cristina Moldovan, Ionel Fizeșan, Andreea-Elena Petru, Ionuț-Valentin Creștin, Adrian Pîrnău, Laurian Vlase and Ovidiu Oniga

Antioxidants 2024, 13(8), 937; https://doi.org/10.3390/antiox13080937 - 1 Aug 2024

Viewed by 863

Abstract

A series of thiazolyl–catechol compounds with antioxidant and cytotoxic activities were synthesized by a Hantzsch heterocyclization, using diverse thioamides as the thiocarbonyl component and 4-chloroacetyl-catechol as haloketone. These compounds were characterized by MS, IR spectroscopy, and NMR. Their antioxidant potential was evaluated by antiradical, electron transfer, and ferrous ion chelation assays using ascorbic acid, Trolox, and EDTA-Na₂ as references. The cytotoxicity of the synthesized compounds was evaluated on two different cell types, normal human foreskin fibroblasts (BJ) and human pulmonary malignant cells (A549), using gefitinib as a reference anticancer drug. The results obtained from the tests highlighted compounds 3g and 3h with significant antioxidant activities. The highest cytotoxic potency against A549 cells was exhibited by compounds 3i and 3j, while compound 3g demonstrated exceptional selectivity on malignant cells compared to gefitinib. These promising results encourage further investigation into targeted modifications on position 2 of the thiazole ring, in order to develop novel therapeutic agents. Full article

(This article belongs to the Special Issue Phenolic Antioxidants)

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18 pages, 2198 KiB

Open AccessArticle

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 1 | Viewed by 780

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 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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14 pages, 2594 KiB

Open AccessArticle

Optimizing Cellulase—Limosilactobacillus fermentum ZC529 Synergy Fermentation for Preserving Macadamia integrifolia Pericarp’s Potential Use as Antioxidants

by Chen Zhang, Haibo Huang, Bifan Liu, Xiongzhuo Tang, Bi’e Tan, Qian Jiang and Yulong Yin

Antioxidants 2024, 13(7), 783; https://doi.org/10.3390/antiox13070783 - 27 Jun 2024

Viewed by 837

Abstract

Macadamia integrifolia pericarps (MIP) are byproducts of nut production which are rich in natural antioxidant compounds, making them an excellent source for extracting bioactive compounds. However, the antioxidant compounds in MIP are easily oxidized under natural storage conditions, resulting in significant biomass loss and resource wastage. To preserve the potential of MIP to be used as an antioxidant product, we employed cellulase and Limosilactobacillus fermentum ZC529 (L.f ZC529) fermentation and utilized response surface methodology to optimize the fermentation parameters for mitigating the antioxidant loss. Total antioxidant capacity (T-AOC) was used as the response variable. The fermented MIP water extract (FMIPE) was obtained via ultrasound-assisted extraction, and its biological activity was evaluated to optimize the best fermentation conditions. Results indicated that a cellulase dosage of 0.9%, an L.f ZC529 inoculation size of 4 mL/100 g, and a fermentation time of 7 days were the optimal conditions for MIP fermentation. Compared to spontaneous fermentation, these optimal conditions significantly increased the total phenolic and total flavonoid contents (p < 0.05). T-AOC was 160.72% increased by this optimal fermentation (p < 0.05). Additionally, supplementation with varying concentrations of FMIPE (6.25%, 12.5%, and 25%) increased the T-AOC, SOD activity, and GSH content, and reduced MDA levels of the oxidative-stressed Drosophila melanogaster (p < 0.05). Moreover, 12.5% and 25% of FMIPE treatments elevated CAT activity in the Drosophila melanogaster (p < 0.05). The effects of FMIPE on GSH and MDA in Drosophila melanogaster were equivalent to the 0.5% vitamin C (Vc) treatment. In summary, synergistic fermentation using cellulase and L.f ZC529 effectively preserves the antioxidant activity of the MIP, offering a simple, eco-friendly method to promote the utilization of MIP resources. Full article

(This article belongs to the Special Issue Phenolic Antioxidants)

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23 pages, 7982 KiB

Open AccessArticle

The Management of Irrigation and Potassium Fertilization to Mitigate the Effect of Light Frosts on the Phenolic and Volatile Compounds in Virgin Olive Oils

by Suony Antonelli, Sebastián Pozas, Jorge Saavedra-Torrico, Mauricio Donders, Chris Bustamante, Betsabet Sepúlveda, Francisco Tapia, Diego L. García-González and Nalda Romero

Antioxidants 2024, 13(5), 559; https://doi.org/10.3390/antiox13050559 - 1 May 2024

Viewed by 1365

Abstract

The frequency of early frosts has increased in recent years, which are injurious to olive growing, causing losses in the yield and quality of virgin olive oil. In this research, it was studied how the management of agronomic factors mitigates frost damage in Arbequina olives, minimizing the loss of phenols and volatiles in virgin olive oil, at different fruit ripening stages. A Box–Behnken design and multivariate analysis were performed, with three levels of irrigation, potassium fertilization, and foliar copper application (15 treatments). Virgin olive oil was extracted from fresh and frozen olives. Light frost caused a significant decrease in the total phenols and secoiridoid compounds in and the antioxidant capacity of the frost-affected oils, which were perceived as more pungent and had the slight defect of “frostbitten olives”. According to the Box–Behnken design, an 86% reference evapotranspiration (ET₀) or higher with 100 potassium oxide units (UK₂O) and a 100% ET₀ or higher with 250 UK₂O would be required to minimize the effect of light frost on phenols and volatiles. Partial Least Squares Regression–Discriminant Analysis (PLS-DA) differentiated the virgin olive oils according to their ripening stage and fresh and frost conditions. Moreover, PLS-DA positively correlated a 75–100% ET₀ and 0 Uk₂O with the dialdehydic form of the decarboxymethyl ligstroside aglycone (p-HPEA-EDA), the dialdehydic form of the decarboxymethyl oleuropein aglycone (3,4-DHPEA-EDA), the dialdehydic form of the ligstroside aglycone (p-HPEA-EDA-DLA), and with fruity, pungent, and bitter attributes. Precision agronomic management based on the needs of the crop itself would avoid unnecessary stress on olive trees and oil damage. Full article

(This article belongs to the Special Issue Phenolic Antioxidants)

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14 pages, 2226 KiB

Open AccessArticle

Accumulation Patterns of Metabolites Responsible for the Functional Quality of Virgin Olive Oil during Olive Fruit Ontogeny

by Pilar Luaces, Jesús Expósito, Paula Benabal, Mar Pascual, Carlos Sanz and Ana G. Pérez

Antioxidants 2024, 13(1), 12; https://doi.org/10.3390/antiox13010012 - 20 Dec 2023

Cited by 5 | Viewed by 1406

Abstract

The health-promoting antioxidant properties of virgin olive oil (VOO) are today considered priority targets in the new olive breeding programs. Given that these properties depend mainly on its phenolic fraction, whose origin lies in the phenolic compounds present in olive fruit, the objective of this study was to provide further insight into the accumulation dynamics of the main antioxidant compounds, including both polar phenolics and lipophilic tocopherols, during the ontogeny of the olive fruit. Data obtained show that, albeit with significant differences, all the studied genotypes share just after fruit set an intense increase in the synthesis of tyrosol and hydroxytyrosol derivatives, by far the main phenolic compounds of the olive fruit, and a subsequent steady decrease along fruit development and ripening. The accumulation dynamics of flavonoids and tocopherols were different from those of tyrosol and hydroxytyrosol derivatives, presenting a peak of synthesis just before the onset of fruit ripening, and then in general, their content decreases throughout the ripening phase. In the case of flavonoids, all genotypes also share a strong increase in the accumulation of anthocyanins in the final stages of fruit ripening, coinciding with the change in fruit color. Furthermore, the results during the fruit ripening process evidenced that the content of tyrosol and hydroxytyrosol derivatives and tocopherols in the fruit largely determines the content of these groups of compounds in the oil. The information acquired could be useful for the selection of the most suitable moment in the ontogeny of the olive fruit for the search for key genes in the biosynthesis of phenolic compounds. Full article

(This article belongs to the Special Issue Phenolic Antioxidants)

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Review

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31 pages, 1613 KiB

Open AccessReview

Fruits, Spices and Honey Phenolic Compounds: A Comprehensive Review on Their Origin, Methods of Extraction and Beneficial Health Properties

by Dimitrios G. Lazaridis, Apostolos-Panagiotis Kitsios, Antonios S. Koutoulis, Olga Malisova and Ioannis K. Karabagias

Antioxidants 2024, 13(11), 1335; https://doi.org/10.3390/antiox13111335 - 31 Oct 2024

Viewed by 921

Abstract

Numerous health benefits have been attributed in the last decades to the regular consumption of fruits, vegetables, herbs and spices, along with honey, in a balanced diet. In this context, the aim of the present review was to provide the literature with the most relevant studies focusing on the determination protocols of these polyphenols and other reducing agents in selected fruits (orange, lemon, grapefruit, prunus, apricot, peach, plum, sweet cherry), spices (oregano, cinnamon, clove, saffron, turmeric) and honey of different botanical origin (nectar or honeydew). In addition, the content and the extraction methods of these compounds, along with their metabolic pathway, have been critically evaluated and discussed. Results showed that all fruits, spices and honey exhibit a considerably high antioxidant activity, which is mainly owed to their phytochemical content. Therefore, a balanced diet consisting of the combination of the foods studied herein may comprise a shield against chronic and other pathophysiological disorders and may be achieved through consecutive educational programs for consumers at an international level. Full article

(This article belongs to the Special Issue Phenolic Antioxidants)

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18 pages, 1009 KiB

Open AccessReview

The Role of Rosmarinic Acid in Cancer Prevention and Therapy: Mechanisms of Antioxidant and Anticancer Activity

by Adam Kowalczyk, Carlo Ignazio Giovanni Tuberoso and Igor Jerković

Antioxidants 2024, 13(11), 1313; https://doi.org/10.3390/antiox13111313 - 28 Oct 2024

Viewed by 855

Abstract

Rosmarinic acid (RA), a polyphenolic compound found in herbs, such as rosemary, basil, and mint, has garnered significant attention due to its potent antioxidant and anticancer properties. This review examined the molecular mechanisms underlying these properties and their potential application in cancer prevention and therapy. It focuses specifically on RA’s role in modulating cancer-related pathways and presents a detailed analysis of recent advancements in this area. A systematic review of PubMed, Scopus, and Web of Science databases was conducted in accordance with PRISMA (Reporting Items for Systematic Reviews and Meta-Analysis) guidelines, focusing on studies published between 2019 and 2024. A total of 25 articles providing evidence from in vitro, in vivo, and in silico studies were selected. These findings elucidate the role of RA in inhibiting tumor cell proliferation, inducing apoptosis, and preventing metastasis in various types of cancer through diverse mechanisms, including its antioxidant properties. Despite these promising results, RA’s bioavailability challenges limit its therapeutic efficacy, underscoring the necessity for improved delivery methods. This review concludes that RA exhibits significant potential as a natural agent for cancer prevention and treatment, although further clinical trials are warranted. Full article

(This article belongs to the Special Issue Phenolic Antioxidants)

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