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The Antioxidant Capacities of Natural Products 2020

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

Deadline for manuscript submissions: closed (31 December 2020) | Viewed by 47703

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Dr. Susana M. Cardoso

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LAQV-REQUIMTE, Department of Chemistry, Universidade de Aveiro, 3810-193 Aveiro, Portugal
Interests: natural products; structural analysis; nutrients and bioactive compounds; liquid chromatography; mass spectrometry; antioxidant; bioactivity; bioaccessibility and bioavailability; added-value products
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Dr. Olívia R. Pereira

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Co-Guest Editor

CIMO (Centro de Investigação de Montanha), Instituto Politecnico de Braganca, 5300-253 Braganca, Portugal
Interests: natural products; bioactive compounds; polyphenols; biological activity; pharmacological activity; drug discovery; cosmetics
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Antioxidant abilities are one of the main pursued bioactive mechanisms, due to their role in the prevention of oxidative-stress events and their related diseases, such as inflammation, cardiovascular diseases, aging-related disorders, and cancer, among others. This perception, along with general consumers’ acceptance of natural products, makes antioxidants of natural origin very attractive to be used as health-promoting agents in a variety of products, including functional foods, supplements, cosmetics, and pharmaceuticals.
Contributions for this Special Issue, both in the form of original research and review articles, may cover all aspects of antioxidants from natural products, including their extraction by conventional and nonconventional methods; purification and structural characterization of new compounds; in vitro and in vivo biological activities of extracts, isolated compounds or new formulated products; structure–bioactive relations; interaction with other substances in the formulated matrices; bioavailability and innovative delivery systems for antioxidants; and safety and stability of new formulated products.

Dr. Susana M. Cardoso
Dr. Olivia Pereira
Guest Editors

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Keywords

Natural products
Antioxidants
Bioactive effects
Structure–bioactivity relations
New functional products
Bioavailability
Delivery systems
Safety

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Published Papers (11 papers)

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Research

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16 pages, 2890 KiB

Open AccessArticle

Bio-Guided Fractionation of Retama raetam (Forssk.) Webb & Berthel Polar Extracts

by Mariem Saada, Hanen Wasli, Inès Jallali, Rim Kboubi, Karl Girard-Lalancette, Vakhtang Mshvildadze, Riadh Ksouri, Jean Legault and Susana M. Cardoso

Molecules 2021, 26(19), 5800; https://doi.org/10.3390/molecules26195800 - 24 Sep 2021

Cited by 5 | Viewed by 2262

Abstract

The fractionation of the methanolic extract (MeOH-E) of Retama raetam (Forssk.) Webb & Berthel and further analysis by thin layer chromatography resulted in four fractions (F1, F2, F3 and F4) that, in parallel with the MeOH-E, were screened for antioxidant, cytotoxic, antidiabetic and antibacterial properties. In addition, chemical characterization of their bioactive molecules was performed using LC-DAD-ESI/MSⁿ. The results indicated that F3 was the most promising regarding antioxidant and cytotoxicity abilities, possibly due to its richness in flavonoids class, particularly isoflavones. In turn, F1 was characterized by the presence of the most polar compounds from MeOH-E (organic acids and piscidic acid) and showed promising abilities to inhibit α-amylase, while F4, which contained prenylated flavonoids and furanoflavonoids, was the most active against the tested bacteria. The gathered results emphasize the distinct biological potentials of purified fractions of Retama raetam. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2020)

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18 pages, 2104 KiB

Open AccessArticle

Effect of AuNPs and AgNPs on the Antioxidant System and Antioxidant Activity of Lavender (Lavandula angustifolia Mill.) from In Vitro Cultures

by Paula Jadczak, Danuta Kulpa, Radosław Drozd, Włodzimierz Przewodowski and Agnieszka Przewodowska

Molecules 2020, 25(23), 5511; https://doi.org/10.3390/molecules25235511 - 25 Nov 2020

Cited by 33 | Viewed by 3838

Abstract

The aim of this study was to determine the effect of gold and silver nanoparticles on the activity of antioxidant enzymes (ascorbate peroxidase (APX), superoxide dismutase (SOD), guaiacol peroxidase (POX), and catalase (CAT)), the free radical scavenging capacity, and the total polyphenol capacity of lavender (Lavandula angustifolia Mill.) cultivar “Munstead” propagated in vitro. In the experiment, fragments of lavender plants were cultivated in vitro on medium with the addition of 1, 2, 5, 10, 20, and 50 mg∙dm⁻³ of AgNPs or AuNPs (particle sizes 24.2 ± 2.4 and 27.5 ± 4.8 nm, respectively). It was found that the nanoparticles increase the activity of the antioxidant enzymes APX and SOD; however, the reaction depends on the NP concentration. The highest APX activity is found in plants propagated on media with 2 and 5 mg∙dm⁻³ of AgNPs. AuNPs significantly increase the APX activity when added to media with a concentration of 10 mg∙dm⁻³. The highest SOD activity is recorded at 2 and 5 mg∙dm⁻³ AgNP and AuNP concentrations. The addition of higher concentrations of nanoparticles to culture media results in a decrease in the APX and SOD activity. The addition of AuNPs to culture media at concentrations from 2 to 50 mg∙dm⁻³ increases the POX activity in comparison to its activity when AgNPs are added to the culture media. No significant influence of NPs on the increase in CAT activity was demonstrated. AgNPs and AuNPs increased the free radical scavenging capacity (ABTS^•+). The addition of NPs at concentrations of 2 and 5 mg∙dm⁻³ increased the production of polyphenols; however, in lower concentrations it decreased their content in lavender tissues. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2020)

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12 pages, 1502 KiB

Open AccessArticle

Evaluation of Antioxidant and Anti-α-glucosidase Activities of Various Solvent Extracts and Major Bioactive Components from the Seeds of Myristica fragrans

by Cai-Wei Li, Yi-Cheng Chu, Chun-Yi Huang, Shu-Ling Fu and Jih-Jung Chen

Molecules 2020, 25(21), 5198; https://doi.org/10.3390/molecules25215198 - 8 Nov 2020

Cited by 23 | Viewed by 3531

Abstract

Myristica fragrans is a well-known species for flavoring many food products and for formulation of perfume and medicated balm. It is also used to treat indigestion, stomach ulcers, liver disorders, and, as emmenagogue, diaphoretic, diuretic, nervine, and aphrodisiac. We examined antioxidant properties and bioactive compounds in various solvent extracts from the seeds of M. fragrans. Methanol, ethanol, and acetone extracts exhibited relatively strong antioxidant activities by 2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl (DPPH), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), superoxide radical, and hydroxyl radical scavenging tests. Furthermore, methanol extracts also displayed significant anti-α-glucosidase activity. Examined and compared to the various solvent extracts for their chemical compositions using HPLC analysis, we isolated the ten higher content compounds and analyzed antioxidant and anti-α-glucosidase activities. Among the isolates, dehydrodiisoeugenol, malabaricone B and malabaricone C were main antioxidant components in seeds of M. fragrans. Malabaricone C exhibited stronger antioxidant capacities than others based on lower half inhibitory concentration (IC₅₀) values in DPPH and ABTS radical scavenging assays, and it also showed significant inhibition of α-glucosidase. These results shown that methanol was found to be the most efficient solvent for extracting the active components from the seeds of M. fragrans, and this material is a potential good source of natural antioxidant and α-glucosidase inhibitor. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2020)

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16 pages, 1916 KiB

Open AccessArticle

Phytochemical Analysis and Antioxidant and Anti-Inflammatory Capacity of the Extracts of Fruits of the Sechium Hybrid

by Itzen Aguiñiga-Sánchez, Marcos Soto-Hernández, Jorge Cadena-Iñiguez, Mario Suwalsky, José R. Colina, Ivan Castillo, Juana Rosado-Pérez, Víctor M. Mendoza-Núñez and Edelmiro Santiago-Osorio

Molecules 2020, 25(20), 4637; https://doi.org/10.3390/molecules25204637 - 12 Oct 2020

Cited by 9 | Viewed by 3375

Abstract

In addition to their own antioxidants, human cells feed on external antioxidants, such as the phenolic compounds of fruits and vegetables, which work together to keep oxidative stress in check. Sechium edule, an edible species of chayote, has phenolic compounds with antioxidant activity and antineoplastic activity. A Sechium hybrid shows one thousand times greater antineoplastic activity than edible species, but its antioxidant and anti-inflammatory activities and the content of phenolic compounds are unknown. The aim of this study was to determine the antioxidant and anti-inflammatory capacity of the extract of fruits of the Sechium hybrid in vitro and in vivo. Phytochemical analysis using HPLC showed that the extract of the Sechium hybrid has at least 16 phenolic compounds; galangin, naringenin, phloretin and chlorogenic acid are the most abundant. In an in vitro assay, this extract inhibited 2,2-diphenyl-L-picrylhydrazyl (DPPH) activity and protected the dimyristoylphosphatidylethanolamine (DMPE) phospholipid model cell membrane from oxidation mediated by hypochlorous acid (HClO). In vivo, it was identified that the most abundant metabolites in the extract enter the bloodstream of the treated mice. On the other hand, the extract reduces the levels of tumor necrosis factor alpha (TNFα), interferon gamma (IFNγ), and interleukin-6 (IL-6) but increases interleukin-10 (IL-10) and glutathione peroxidase levels. Our findings indicate that intake of the fruits of the Sechium hybrid leads to antioxidant and anti-inflammatory effects in a mouse model. Therefore, these results support the possibility of exploring the clinical effect of this hybrid in humans. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2020)

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18 pages, 5381 KiB

Open AccessArticle

Consumption of Anacardium occidentale L. (Cashew Nuts) Inhibits Oxidative Stress through Modulation of the Nrf2/HO−1 and NF-kB Pathways

by Roberta Fusco, Marika Cordaro, Rosalba Siracusa, Alessio Filippo Peritore, Enrico Gugliandolo, Tiziana Genovese, Ramona D’Amico, Rosalia Crupi, Antonella Smeriglio, Giuseppina Mandalari, Daniela Impellizzeri, Salvatore Cuzzocrea and Rosanna Di Paola

Molecules 2020, 25(19), 4426; https://doi.org/10.3390/molecules25194426 - 26 Sep 2020

Cited by 55 | Viewed by 3627

Abstract

Ischemia/reperfusion injury is a severe disorder associated with a high mortality. Several antioxidant and pharmacological properties of cashew nuts (Anacardium occidentale L.) and its metabolites from different countries have recently been described. It is a medicinal plant with important therapeutic effects. This study aimed to verify the effect of an oral administration of cashew nuts in a rat model of ischemia/reperfusion (I/R). Adult male rats were subjected to intestinal I/R injury by clamping the superior mesenteric artery for 30 min and then allowing animals to 1 h of reperfusion. Rats subjected to I/R of the gut showed a significant increase in different biochemical markers. In particular, we evaluated lipid peroxidation, tissue myeloperoxidase activity, protein carbonyl content, reactive oxygen species generation and decreased antioxidant enzyme activities. Western blot analysis showed the activation of the NRF2 and NF-kB pathways. Increased immunoreactivity to nitrotyrosine, PARP, P-selectin, and ICAM-1 was observed in the ileum of rats subjected to I/R. Administration of cashew nuts (100 mg/kg) significantly reduced the mortality rate, the fall in arterial blood pressure, and oxidative stress and restored the antioxidant enzyme activities by a mechanism involving both NRF2 and NF-kB pathways. Cashew nuts treatments reduced cytokines plasma levels, nitrotyrosine, and PARP expression as well as adhesion molecules expressions. Additionally, cashew nuts decreased the intestinal barrier dysfunction and mucosal damage, the translocation of toxins and bacteria, which leads to systemic inflammation and associated organs injuries in particular of liver and kidney. Our study demonstrates that cashew nuts administration exerts antioxidant and pharmacological protective effects in superior mesenteric artery occlusion–reperfusion shock. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2020)

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15 pages, 3062 KiB

Open AccessArticle

Xanthine Oxidase Inhibition and Anti-LDL Oxidation by Prenylated Isoflavones from Flemingia philippinensis Root

by Jeong Yoon Kim, Yan Wang, Zuo Peng Li, Aizhamal Baiseitova, Yeong Jun Ban and Ki Hun Park

Molecules 2020, 25(13), 3074; https://doi.org/10.3390/molecules25133074 - 6 Jul 2020

Cited by 13 | Viewed by 2735

Abstract

Xanthine oxidase is a frontier enzyme to produce oxidants, which leads to inflammation in the blood. Prenylated isoflavones from Flemingia philippinensis were found to display potent inhibition against xanthine oxidase (XO). All isolates (1–9) inhibited XO enzyme with IC₅₀ ranging 7.8~36.4 μM. The most active isoflavones (2–5, IC₅₀ = 7.8~14.8 μM) have the structural feature of a catechol motif in B-ring. Inhibitory behaviors were disclosed as a mixed type I mode of inhibition with K_I < K_IS. Binding affinities to XO enzyme were evaluated. Fluorescence quenching effects agreed with inhibitory potencies (IC₅₀s). The compounds (2–5) also showed potent anti-LDL oxidation effects in the thiobarbituric acid-reactive substances (TBARS) assay, the lag time of conjugated diene formation, relative electrophoretic mobility (REM), and fragmentation of apoB-100 on copper-mediated LDL oxidation. The compound 4 protected LDL oxidation with 0.7 μM in TBARS assay, which was 40-fold more active than genistein (IC₅₀ = 30.4 μM). Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2020)

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15 pages, 1788 KiB

Open AccessArticle

Antioxidant Sulfated Polysaccharide from Edible Red Seaweed Gracilaria birdiae is an Inhibitor of Calcium Oxalate Crystal Formation

by Leticia Castelo Branco Peroba Oliveira, Moacir Fernandes Queiroz, Gabriel Pereira Fidelis, Karoline Rachel Teodosio Melo, Rafael Barros Gomes Câmara, Monique Gabriela Chagas Faustino Alves, Leandro Silva Costa, Dárlio Inácio Alves Teixeira, Raniere Fagundes Melo-Silveira and Hugo Alexandre Oliveira Rocha

Molecules 2020, 25(9), 2055; https://doi.org/10.3390/molecules25092055 - 28 Apr 2020

Cited by 10 | Viewed by 3420

Abstract

The genus Gracilaria synthesizes sulfated polysaccharides (SPs). Many of these SPs, including those synthesized by the edible seaweed Gracilaria birdiae, have not yet been adequately investigated for their use as potential pharmaceutical compounds. Previous studies have demonstrated the immunomodulatory effects of sulfated galactans from G. birdiae. In this study, a galactan (GB) was extracted from G. birdiae and evaluated by cell proliferation and antioxidant tests. GB showed no radical hydroxyl (OH) and superoxide (O₂⁻) scavenging ability. However, GB was able to donate electrons in two further different assays and presented iron- and copper-chelating activity. Urolithiasis affects approximately 10% of the world’s population and is strongly associated with calcium oxalate (CaOx) crystals. No efficient compound is currently available for the treatment of this disease. GB appeared to interact with and stabilize calcium oxalate dihydrate crystals, leading to the modification of their morphology, size, and surface charge. These crystals then acquired the same characteristics as those found in healthy individuals. In addition, GB showed no cytotoxic effect against human kidney cells (HEK-293). Taken together, our current findings highlight the potential application of GB as an antiurolithic agent. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2020)

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20 pages, 952 KiB

Open AccessArticle

Antioxidants and Health-Beneficial Nutrients in Fruits of Eighteen Cucurbita Cultivars: Analysis of Diversity and Dietary Implications

by Anna Kostecka-Gugała, Michał Kruczek, Iwona Ledwożyw-Smoleń and Paweł Kaszycki

Molecules 2020, 25(8), 1792; https://doi.org/10.3390/molecules25081792 - 14 Apr 2020

Cited by 36 | Viewed by 4952

Abstract

Aging is accompanied by gradual accumulation of molecular damage within cells in response to oxidative stress resulting from adverse environmental factors, inappropriate lifestyle, and numerous diseases. Adequate antioxidant intake is a key factor of proper diet. The study aimed to assess the antioxidant/antiradical capacities of Cucurbita fruits (18 cultivars of the species: C. maxima Duch., C. moschata Duch., C. pepo L., and C. ficifolia Bouché) grown in central Europe. The analyses were based on the FRAP (ferric reducing antioxidant power), CUPRAC (cupric ion reducing antioxidant capacity), and DPPH (2,2-diphenyl-1-picrylhydrazyl radical) assays. The content of phenolic compounds and β-carotene was evaluated with HPLC (high performance liquid chromatography), while the main macro- and micronutrients by ICP-OES (inductively coupled plasma mass spectrometry). The results revealed high intraspecies variability within the Cucurbita genus. The Japanese ‘Kogigu’ fruits were distinguished as extraordinary sources of phenolic compounds, including syringic and protocatechuic acids, catechin, and kaempferol. Another popular cultivar ‘Hokkaido’ exhibited the highest antioxidant and antiradical capacities. Most of the fruits proved to be rich sources of zinc and copper. The obtained data are discussed in the context of optimized nutrition of the elderly and suggest that Cucurbita fruits should become daily components of their diet. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2020)

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15 pages, 4862 KiB

Open AccessArticle

Protective Effect of Astaxanthin on Ochratoxin A-Induced Kidney Injury to Mice by Regulating Oxidative Stress-Related NRF2/KEAP1 Pathway

by Lin Li, Yueli Chen, Danyang Jiao, Shuhua Yang, Lin Li and Peng Li

Molecules 2020, 25(6), 1386; https://doi.org/10.3390/molecules25061386 - 18 Mar 2020

Cited by 54 | Viewed by 3987

Abstract

The present study aimed to investigate the effects of astaxanthin (ASX) on ochratoxin A (OTA)-induced renal oxidative stress and its mechanism of action. Serum kidney markers, histomorphology, ultrastructural observation, and oxidative stress indicators were assessed. Meanwhile, quantitative real-time reverse transcription PCR and western blotting detection of NRF2 (encoding nuclear factor, erythroid 2 like) and members of the NRF2/KEAP1 signaling pathway (KEAP1 (encoding Kelch-like ECH-associated protein), NQO1 (encoding NAD(P)H quinone dehydrogenase), HO-1 (encoding heme oxygenase 1), γ-GCS (gamma-glutamylcysteine synthetase), and GSH-Px (glutathione peroxidase 1)) were performed. Compared with the control group, the OTA-treated group showed significantly increased levels of serum UA (uric acid) and BUN (blood urea nitrogen), tubular epithelial cells were swollen and degenerated, and the levels of antioxidant enzymes decreased significantly, and the expression of NRF2 (cytoplasm), NQO1, HO-1, γ-GCS, and GSH-Px decreased significantly. More importantly, after ASX pretreatment, compared with the OTA group, serum markers were decreased, epithelial cells appeared normal; the expression of antioxidant enzymes increased significantly, NQO1, HO-1, γ-GCS and GSH-Px levels increased significantly, and ASX promoted the transfer of NRF2 from the cytoplasm to the nucleus. These results highlight the protective ability of ASX in renal injury caused by OTA exposure, and provide theoretical support for ASX’s role in other mycotoxin-induced damage. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2020)

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Review

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20 pages, 1712 KiB

Open AccessReview

Recent Advances in the Production and Applications of Ellagic Acid and Its Derivatives. A Review

by Dmitry D. Evtyugin, Sandra Magina and Dmitry V. Evtuguin

Molecules 2020, 25(12), 2745; https://doi.org/10.3390/molecules25122745 - 13 Jun 2020

Cited by 122 | Viewed by 8419

Abstract

Ellagitannins (ETs), characterized by their diversity and chemical complexity, belong to the class of hydrolysable tannins that, via hydrolysis under acidic or alkaline conditions, can yield ellagic acid (EA). They are mostly found as a part of extractives in angiosperms. As known antioxidants and chelators, EA and EA derivatives are drawing an increasing interest towards extensive technical and biomedical applications. The latter ones include possible antibacterial, antifungal, antiviral, anti-inflammatory, hepato- and cardioprotective, chemopreventive, neuroprotective, anti-diabetic, gastroprotective, antihyperlipidemic, and antidepressant-like activities, among others. EA’s synthesis and production challenges prompt further research on new methods and alternative sources. Conventional and prospective methods and raw materials for the production of EA and its derivatives are reviewed. Among the potential sources of EA, the residues and industrial streams of the pulp industry have been highlighted and considered as an alluring alternative in terms of commercial exploitation. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2020)

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20 pages, 4157 KiB

Open AccessReview

Biological Activity of Some Aromatic Plants and Their Metabolites, with an Emphasis on Health-Promoting Properties

by Marek Kieliszek, Amr Edris, Anna Maria Kot and Kamil Piwowarek

Molecules 2020, 25(11), 2478; https://doi.org/10.3390/molecules25112478 - 27 May 2020

Cited by 31 | Viewed by 6626

Abstract

The biological activities of four aromatic plants, namely frankincense, myrrh, ginger, and turmeric, were reviewed in the current study. The volatile fraction (essential oil) as well as the nonvolatile fraction of these four plants showed different promising biological activities that are displayed in detail. These activities can include protection from and/or alleviation of some ailment, which is supported with different proposed mechanisms of action. This review aimed to finally help researchers to get a handle on the importance of considering these selected aromatic plants, which have not been thoroughly reviewed before, as a potential adjuvant to classical synthetic drugs to enhance their efficiency. Moreover, the results elicited in this review encourage the consumption of these medicinal plants as an integrated part of the diet to boost the body’s overall health based on scientific evidence. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2020)

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