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Secondary Metabolites for the Reduction of Oxidative Stress

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Medicinal Chemistry".

Deadline for manuscript submissions: closed (31 March 2023) | Viewed by 38451

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Special Issue Editor

Prof. Dr. Andrea Ragusa

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Department of Biological and Environmental Sciences and Technologies, Campus Ecotekne, University of Salento, Via Monteroni, 73100 Lecce, Italy
Interests: medicinal and pharmaceutical chemistry; supramolecular chemistry; nanomedicine; theranostics; metabolomics; nuclear magnetic resonance; HPLC analysis; nutraceutics
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Dear Colleagues,

Oxidative stress is at the base of several pathological conditions. Reactive oxigen species (ROS) are normally produced inside cells, but their amount is finelly counterbalanced by antioxidant enzymes, e.g., SOD, GPx, and catalase. However, when this homeostasis is interrupted, cells suffer from oxidative stress that can also lead to cardivascular and neurodegenerative diseases, as well as cancer, to name a few.

In order to help cells to fight excess of ROS, esogenous antioxidant molecules can be administered through diet. For example, fruit and vegetables are rich in secondary metabolites with antioxidant properties, as are many bevarages obtained from natural products. Wine is at the base of the Frech paradox, supposedly because of the high amount of polyphenols contained. Olive oil is one of the base components of the Mediterranean diet and strongly contributes to its beneficial health effects.

Several molecules contained in these products, although at low concentration, have already been shown to exert antioxidant activity, among others, both in vitro and in vivo.

This Special Issue of Molecules aims at collecting contributions from original research articles as well as reviews regarding the exploitation of secondary metabolites in natural products (or derived from them) for reducing oxidative stress. Delivery systems involving technological approaches, e.g., co-polymers or nanoparticles, for overcoming biological barriers and improving the efficacy of the formulation are also welcome.

Prof. Dr. Andrea Ragusa
Guest Editor

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Keywords

Polyphenols
Antioxidants
ROS
Neuroprotection
Oxidative stress

Published Papers (12 papers)

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Research

Jump to: Review

16 pages, 4158 KiB

Open AccessArticle

Compound 275# Induces Mitochondria-Mediated Apoptosis and Autophagy Initiation in Colorectal Cancer Cells through an Accumulation of Intracellular ROS

by Dong-Lin Yang, Yong Li, Shui-Qing Ma, Ya-Jun Zhang, Jiu-Hong Huang and Liu-Jun He

Molecules 2023, 28(7), 3211; https://doi.org/10.3390/molecules28073211 - 4 Apr 2023

Viewed by 1248

Abstract

Colorectal cancer (CRC) is the most common intestinal malignancy, and nearly 70% of patients with this cancer develop metastatic disease. In the present study, we synthesized a novel compound, termed N-(3-(5,7-dimethylbenzo [d]oxazol-2-yl)phenyl)-5-nitrofuran-2-carboxamide (compound 275#), and found that it exhibits antiproliferative capability in suppressing the proliferation and growth of CRC cell lines. Furthermore, compound 275# triggered caspase 3-mediated intrinsic apoptosis of mitochondria and autophagy initiation. An investigation of the molecular mechanisms demonstrated that compound 275# induced intrinsic apoptosis, and autophagy initiation was largely mediated by increasing the levels of the intracellular accumulation of reactive oxygen species (ROS) in CRC cells. Taken together, these data suggest that ROS accumulation after treatment with compound 275# leads to mitochondria-mediated apoptosis and autophagy activation, highlighting the potential of compound 275# as a novel therapeutic agent for the treatment of CRC. Full article

(This article belongs to the Special Issue Secondary Metabolites for the Reduction of Oxidative Stress)

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14 pages, 5033 KiB

Open AccessArticle

Humulus lupulus L. Extract Protects against Senior Osteoporosis through Inhibiting Amyloid β Deposition and Oxidative Stress in APP/PS1 Mutated Transgenic Mice and Osteoblasts

by Tianshuang Xia, Jiabao Zhang, Yunxiang Guo, Yiping Jiang, Fangliang Qiao, Kun Li, Nani Wang, Ting Han and Hailiang Xin

Molecules 2023, 28(2), 583; https://doi.org/10.3390/molecules28020583 - 6 Jan 2023

Cited by 4 | Viewed by 1834

Abstract

As aging progresses, β-amyloid (Aβ) deposition and the resulting oxidative damage are key causes of aging diseases such as senior osteoporosis (SOP). Humulus lupulus L. (hops) is an important medicinal plant widely used in the food, beverage and pharmaceutical industries due to its strong antioxidant ability. In this study, APP/PS1 mutated transgenic mice and Aβ-injured osteoblasts were used to evaluate the protective effects of hops extracts (HLE) on SOP. Mice learning and memory levels were assessed by the Morris water maze. Mice femurs were prepared for bone micro-structures and immunohistochemistry experiments. The deposition of Aβ in the hippocampus, cortex and femurs were determined by Congo red staining. Moreover, protein expressions related to antioxidant pathways were evaluated by Western blotting. It was found that HLE markedly improved learning abilities and ameliorated memory impairment of APP/PS1 mice, as well as regulated antioxidant enzymes and bone metabolism proteins in mice serum. Micro-CT tests indicated that HLE enhanced BMD and improved micro-architectural parameters of mice femur. More importantly, it was discovered that HLE significantly reduced Aβ deposition both in the brain and femur. Further in vitro results showed HLE increased the bone mineralization nodule and reduced the ROS level of Aβ-injured osteoblasts. Additionally, HLE increased the expression of antioxidant related proteins Nrf2, HO-1, NQO1, FoxO1 and SOD-2. These results indicated that Humulus lupulus L. extract could protect against senior osteoporosis through inhibiting Aβ deposition and oxidative stress, which provides a reference for the clinical application of hops in the prevention and treatment of SOP. Full article

(This article belongs to the Special Issue Secondary Metabolites for the Reduction of Oxidative Stress)

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11 pages, 1870 KiB

Open AccessArticle

Protective Effect of Flavonoids against Methylglyoxal-Induced Oxidative Stress in PC-12 Neuroblastoma Cells and Its Structure–Activity Relationships

by Danyang Zhang, Xia Li, Xiaoshi He, Yan Xing, Bo Jiang, Zhilong Xiu, Yongming Bao and Yuesheng Dong

Molecules 2022, 27(22), 7804; https://doi.org/10.3390/molecules27227804 - 12 Nov 2022

Cited by 1 | Viewed by 1823

Abstract

Methylglyoxal-induced oxidative stress and cytotoxicity are the main factors causing neuronal death-related, diabetically induced memory impairment. Antioxidant and anti-apoptotic therapy are potential intervention strategies. In this study, 25 flavonoids with different substructures were assayed for protecting PC-12 cells from methylglyoxal-induced damage. A structure–activity relationship (SAR) analysis indicated that the absence of the double bond at C-2 and C-3, substitutions of the gallate group at the 3 position, the pyrogallol group at the B-ring, and the R configuration of the 3 position enhanced the protection of flavan-3-ols, and a hydroxyl substitution at the 4′ and meta-positions were important for the protection of flavonol. These SARs were further confirmed by molecular docking using the active site of the Keap1–Nrf2 complex as the receptor. The mechanistic study demonstrated that EGCG with the lowest EC₅₀ protected the PC-12 cells from methylglyoxal-induced damage by reducing oxidative stress via the Nrf2/Keap1/HO-1 and Bcl-2/Bax signaling pathways. These results suggested that flavan-3-ols might be a potential dietary supplement for protection against diabetic encephalopathy. Full article

(This article belongs to the Special Issue Secondary Metabolites for the Reduction of Oxidative Stress)

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17 pages, 2701 KiB

Open AccessArticle

Potent Activity of a High Concentration of Chemical Ozone against Antibiotic-Resistant Bacteria

by Karyne Rangel, Fellipe O. Cabral, Guilherme C. Lechuga, João P. R. S. Carvalho, Maria H. S. Villas-Bôas, Victor Midlej and Salvatore G. De-Simone

Molecules 2022, 27(13), 3998; https://doi.org/10.3390/molecules27133998 - 22 Jun 2022

Cited by 11 | Viewed by 2403

Abstract

Background: Health care-associated infections (HAIs) are a significant public health problem worldwide, favoring multidrug-resistant (MDR) microorganisms. The SARS-CoV-2 infection was negatively associated with the increase in antimicrobial resistance, and the ESKAPE group had the most significant impact on HAIs. The study evaluated the bactericidal effect of a high concentration of O₃ gas on some reference and ESKAPE bacteria. Material and Methods: Four standard strains and four clinical or environmental MDR strains were exposed to elevated ozone doses at different concentrations and times. Bacterial inactivation (growth and cultivability) was investigated using colony counts and resazurin as metabolic indicators. Scanning electron microscopy (SEM) was performed. Results: The culture exposure to a high level of O₃ inhibited the growth of all bacterial strains tested with a statistically significant reduction in colony count compared to the control group. The cell viability of S. aureus (MRSA) (99.6%) and P. aeruginosa (XDR) (29.2%) was reduced considerably, and SEM showed damage to bacteria after O₃ treatment Conclusion: The impact of HAIs can be easily dampened by the widespread use of ozone in ICUs. This product usually degrades into molecular oxygen and has a low toxicity compared to other sanitization products. However, high doses of ozone were able to interfere with the growth of all strains studied, evidencing that ozone-based decontamination approaches may represent the future of hospital cleaning methods. Full article

(This article belongs to the Special Issue Secondary Metabolites for the Reduction of Oxidative Stress)

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12 pages, 2976 KiB

Open AccessArticle

Antioxidant Assessment of Prenylated Stilbenoid-Rich Extracts from Elicited Hairy Root Cultures of Three Cultivars of Peanut (Arachis hypogaea)

by Gaurav Gajurel, Rokib Hasan and Fabricio Medina-Bolivar

Molecules 2021, 26(22), 6778; https://doi.org/10.3390/molecules26226778 - 10 Nov 2021

Cited by 10 | Viewed by 2925

Abstract

Peanut produces prenylated stilbenoids upon biotic stress. However, the role of these compounds against oxidative stress have not been thoroughly elucidated. To this end, the antioxidant capacity of extracts enriched in prenylated stilbenoids and derivatives was studied. To produce these extracts, hairy root cultures of peanut cultivars Hull, Tifrunner, and Georgia Green were co-treated with methyl jasmonate, cyclodextrin, hydrogen peroxide, and magnesium chloride and then the stilbenoids were extracted from the culture medium. Among the three cultivars, higher levels of the stilbenoid derivatives arachidin-1 and arachidin-6 were detected in cultivar Tifrunner. Upon reaction with 2,2-diphenyl-1picrylhydrazyl, extracts from cultivar Tifrunner showed the highest antioxidant capacity with an IC₅₀ of 6.004 µg/mL. Furthermore, these extracts had significantly higher antioxidant capacity at 6.25 µg/mL and 3.125 µg/mL when compared to extracts from cultivars Hull and Georgia Green. The stilbenoid-rich extracts from peanut hairy roots show high antioxidant capacity and merit further study as potential nutraceuticals to promote human health. Full article

(This article belongs to the Special Issue Secondary Metabolites for the Reduction of Oxidative Stress)

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19 pages, 5876 KiB

Open AccessArticle

Oxidative Stress and Multi-Organel Damage Induced by Two Novel Phytocannabinoids, CBDB and CBDP, in Breast Cancer Cells

by Maria Salbini, Alessandra Quarta, Fabiana Russo, Anna Maria Giudetti, Cinzia Citti, Giuseppe Cannazza, Giuseppe Gigli, Daniele Vergara and Antonio Gaballo

Molecules 2021, 26(18), 5576; https://doi.org/10.3390/molecules26185576 - 14 Sep 2021

Cited by 4 | Viewed by 3172

Abstract

Over the last few years, much attention has been paid to phytocannabinoids derived from Cannabis for their therapeutic potential. Δ⁹-tetrahydrocannabinol (Δ⁹-THC) and cannabidiol (CBD) are the most abundant compounds of the Cannabis sativa L. plant. Recently, novel phytocannabinoids, such as cannabidibutol (CBDB) and cannabidiphorol (CBDP), have been discovered. These new molecules exhibit the same terpenophenolic core of CBD and differ only for the length of the alkyl side chain. Roles of CBD homologs in physiological and pathological processes are emerging but the exact molecular mechanisms remain to be fully elucidated. Here, we investigated the biological effects of the newly discovered CBDB or CBDP, compared to the well-known natural and synthetic CBD (nat CBD and syn CBD) in human breast carcinoma cells that express CB receptors. In detail, our data demonstrated that the treatment of cells with the novel phytocannabinoids affects cell viability, increases the production of reactive oxygen species (ROS) and activates cellular pathways related to ROS signaling, as already demonstrated for natural CBD. Moreover, we observed that the biological activity is significantly increased upon combining CBD homologs with drugs that inhibit the activity of enzymes involved in the metabolism of endocannabinoids, such as the monoacylglycerol lipase (MAGL) inhibitor, or with drugs that induces the activation of cellular stress pathways, such as the phorbol ester 12-myristate 13-acetate (PMA). Full article

(This article belongs to the Special Issue Secondary Metabolites for the Reduction of Oxidative Stress)

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15 pages, 2706 KiB

Open AccessArticle

Therapeutic Effects of Gallic Acid in Regulating Senescence and Diabetes; an In Vitro Study

by Mahban Rahimifard, Maryam Baeeri, Haji Bahadar, Shermineh Moini-Nodeh, Madiha Khalid, Hamed Haghi-Aminjan, Hossein Mohammadian and Mohammad Abdollahi

Molecules 2020, 25(24), 5875; https://doi.org/10.3390/molecules25245875 - 11 Dec 2020

Cited by 37 | Viewed by 3165

Abstract

Gallic acid (GA), a plant-derived ubiquitous secondary polyphenol metabolite, can be a useful dietary supplement. This in vitro study’s primary purpose was to assess the anti-aging properties of GA using rat embryonic fibroblast (REF) cells, antidiabetic effects via pancreatic islet cells, and finally, elucidating the molecular mechanisms of this natural compound. REF and islet cells were isolated from fetuses and pancreas of rats, respectively. Then, several senescence-associated molecular and biochemical parameters, along with antidiabetic markers, were investigated. GA caused a significant decrease in the β-galactosidase activity and reduced inflammatory cytokines and oxidative stress markers in REF cells. GA reduced the G0/G1 phase in senescent REF cells that led cells to G2/M. Besides, GA improved the function of the β cells. Flow cytometry and spectrophotometric analysis showed that it reduces apoptosis via inhibiting caspase-9 activity. Taken together, based on the present findings, this polyphenol metabolite at low doses regulates different pathways of senescence and diabetes through its antioxidative stress potential and modulation of mitochondrial complexes activities. Full article

(This article belongs to the Special Issue Secondary Metabolites for the Reduction of Oxidative Stress)

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13 pages, 3422 KiB

Open AccessArticle

The Effects of Prolonged Storage on ARPE-19 Cells Stored at Three Different Storage Temperatures

by Rakibul Islam, Rima Maria Corraya, Lara Pasovic, Ayyad Zartasht Khan, Hans Christian D. Aass, Jon Roger Eidet and Tor Paaske Utheim

Molecules 2020, 25(24), 5809; https://doi.org/10.3390/molecules25245809 - 9 Dec 2020

Cited by 5 | Viewed by 2537

Abstract

This study aimed to investigate how prolonged storage of adult retinal pigment epithelial (ARPE-19) cell sheets affects cell metabolism, morphology, viability, and phenotype. ARPE-19 cell sheets were stored at three temperatures (4 °C, 16 °C, and 37 °C) for three weeks. Metabolic status and morphology of the cells were monitored by sampling medium and examining cells by phase-contrast microscopy, respectively, throughout the storage period. Cell viability was analyzed by flow cytometry, and phenotype was determined by epifluorescence microscopy after the storage. Lactate production and glucose consumption increased heavily, while pH dropped considerably, through storage at 37 °C compared to 4 °C and 16 °C. During storage, morphology started to deteriorate first at 4 °C, then at 37 °C, and was maintained the longest at 16 °C. Viability of the cells after three weeks of storage was best preserved at 16 °C, while cells stored at 4 °C and 37 °C had reduced viability. Dedifferentiation indicated by reduced expression of retinal pigment epithelium-specific protein 65 (RPE65), zonula occludens protein 1 (ZO-1), and occludin after three weeks of storage was noticed in all experimental groups compared to control. We conclude that storage temperature affects the metabolic status of ARPE-19 cells and that 16 °C reduces metabolic activity while protecting viability and morphology. Full article

(This article belongs to the Special Issue Secondary Metabolites for the Reduction of Oxidative Stress)

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Review

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12 pages, 566 KiB

Open AccessReview

Cystic Fibrosis and Oxidative Stress: The Role of CFTR

by Evelina Moliteo, Monica Sciacca, Antonino Palmeri, Maria Papale, Sara Manti, Giuseppe Fabio Parisi and Salvatore Leonardi

Molecules 2022, 27(16), 5324; https://doi.org/10.3390/molecules27165324 - 21 Aug 2022

Cited by 14 | Viewed by 2481

Abstract

There is substantial evidence in the literature that patients with cystic fibrosis (CF) have higher oxidative stress than patients with other diseases or healthy subjects. This results in an increase in reactive oxygen species (ROS) and in a deficit of antioxidant molecules and plays a fundamental role in the progression of chronic lung damage. Although it is known that recurrent infection–inflammation cycles in CF patients generate a highly oxidative environment, numerous clinical and preclinical studies suggest that the airways of a patient with CF present an inherently abnormal proinflammatory milieu due to elevated oxidative stress and abnormal lipid metabolism even before they become infected. This could be directly related to cystic fibrosis transmembrane conductance regulator (CFTR) deficiency, which appears to produce a redox imbalance in epithelial cells and extracellular fluids. This review aims to summarize the main mechanism by which CFTR deficiency is intrinsically responsible for the proinflammatory environment that characterizes the lung of a patient with CF. Full article

(This article belongs to the Special Issue Secondary Metabolites for the Reduction of Oxidative Stress)

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17 pages, 3759 KiB

Open AccessReview

Recent Overview of Resveratrol’s Beneficial Effects and Its Nano-Delivery Systems

by Raghvendra A. Bohara, Nazish Tabassum, Mohan P. Singh, Giuseppe Gigli, Andrea Ragusa and Stefano Leporatti

Molecules 2022, 27(16), 5154; https://doi.org/10.3390/molecules27165154 - 12 Aug 2022

Cited by 15 | Viewed by 2730

Abstract

Natural polyphenols have a wide variety of biological activities and are taken into account as healthcare materials. Resveratrol is one such natural polyphenol, belonging to a group known as stilbenoids (STBs). Resveratrol (3,5,4′-trihydroxy-trans-stilbene) is mainly found in grapes, wine, nuts, and berries. A wide range of biological activities has been demonstrated by resveratrol, including antimicrobial, antioxidant, antiviral, antifungal, and antiaging effects, and many more are still under research. However, as with many other plant-based polyphenol products, resveratrol suffers from low bioavailability once administered in vivo due to its susceptibility to rapid enzyme degradation by the body’s innate immune system before it can exercise its therapeutic influence. Therefore, it is of the utmost importance to ensure the best use of resveratrol by creating a proper resveratrol delivery system. Nanomedicine and nanodelivery systems utilize nanoscale materials as diagnostic tools or to deliver therapeutic agents in a controlled manner to specifically targeted locations. After a brief introduction about polyphenols, this review overviews the physicochemical characteristics of resveratrol, its beneficial effects, and recent advances on novel nanotechnological approaches for its delivery according to the type of nanocarrier utilized. Furthermore, the article summarizes the different potential applications of resveratrol as, for example, a therapeutic and disease-preventing anticancer and antiviral agent. Full article

(This article belongs to the Special Issue Secondary Metabolites for the Reduction of Oxidative Stress)

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23 pages, 1849 KiB

Open AccessReview

Olive Tree in Circular Economy as a Source of Secondary Metabolites Active for Human and Animal Health Beyond Oxidative Stress and Inflammation

by Rosanna Mallamaci, Roberta Budriesi, Maria Lisa Clodoveo, Giulia Biotti, Matteo Micucci, Andrea Ragusa, Francesca Curci, Marilena Muraglia, Filomena Corbo and Carlo Franchini

Molecules 2021, 26(4), 1072; https://doi.org/10.3390/molecules26041072 - 18 Feb 2021

Cited by 36 | Viewed by 5159

Abstract

Extra-virgin olive oil (EVOO) contains many bioactive compounds with multiple biological activities that make it one of the most important functional foods. Both the constituents of the lipid fraction and that of the unsaponifiable fraction show a clear action in reducing oxidative stress by acting on various body components, at concentrations established by the European Food Safety Authority’s claims. In addition to the main product obtained by the mechanical pressing of the fruit, i.e., the EVOO, the residual by-products of the process also contain significant amounts of antioxidant molecules, thus potentially making the Olea europea L. an excellent example of the circular economy. In fact, the olive mill wastewaters, the leaves, the pomace, and the pits discharged from the EVOO production process are partially recycled in the nutraceutical and cosmeceutical fields also because of their antioxidant effect. This work presents an overview of the biological activities of these by-products, as shown by in vitro and in vivo assays, and also from clinical trials, as well as their main formulations currently available on the market. Full article

(This article belongs to the Special Issue Secondary Metabolites for the Reduction of Oxidative Stress)

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25 pages, 2215 KiB

Open AccessFeature PaperReview

Bioactive Metabolites from Marine Algae as Potent Pharmacophores against Oxidative Stress-Associated Human Diseases: A Comprehensive Review

by Biswajita Pradhan, Rabindra Nayak, Srimanta Patra, Bimal Prasad Jit, Andrea Ragusa and Mrutyunjay Jena

Molecules 2021, 26(1), 37; https://doi.org/10.3390/molecules26010037 - 23 Dec 2020

Cited by 84 | Viewed by 7143

Abstract

In addition to cancer and diabetes, inflammatory and ROS-related diseases represent one of the major health problems worldwide. Currently, several synthetic drugs are used to reduce oxidative stress; nevertheless, these approaches often have side effects. Therefore, to overcome these issues, the search for alternative therapies has gained importance in recent times. Natural bioactive compounds have represented, and they still do, an important source of drugs with high therapeutic efficacy. In the “synthetic” era, terrestrial and aquatic photosynthetic organisms have been shown to be an essential source of natural compounds, some of which might play a leading role in pharmaceutical drug development. Marine organisms constitute nearly half of the worldwide biodiversity. In the marine environment, algae, seaweeds, and seagrasses are the first reported sources of marine natural products for discovering novel pharmacophores. The algal bioactive compounds are a potential source of novel antioxidant and anticancer (through modulation of the cell cycle, metastasis, and apoptosis) compounds. Secondary metabolites in marine Algae, such as phenolic acids, flavonoids, and tannins, could have great therapeutic implications against several diseases. In this context, this review focuses on the diversity of functional compounds extracted from algae and their potential beneficial effects in fighting cancer, diabetes, and inflammatory diseases. Full article

(This article belongs to the Special Issue Secondary Metabolites for the Reduction of Oxidative Stress)

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