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16 pages, 2581 KiB

Open AccessArticle

Neuroprotective Efficacy of a Nanomicellar Complex of Carnosine and Lipoic Acid in a Rat Model of Rotenone-Induced Parkinson’s Disease

by Olga Kulikova, Dmitry Troshev, Daniil Berezhnoy, Sergey Stvolinsky, Yulia Timoshina, Denis Abaimov, Olga Muzychuk, Alexander Latanov and Tatiana Fedorova

Antioxidants 2023, 12(6), 1215; https://doi.org/10.3390/antiox12061215 - 4 Jun 2023

Cited by 1 | Viewed by 1383

Abstract

Oxidative stress, accompanied by mitochondrial dysfunction, is a key mechanism involved in the pathogenesis of Parkinson’s disease (PD). Both carnosine and lipoic acid are potent antioxidants, the applicability of which in therapy is hindered by their limited bioavailability. This study aimed to evaluate [...] Read more.

Oxidative stress, accompanied by mitochondrial dysfunction, is a key mechanism involved in the pathogenesis of Parkinson’s disease (PD). Both carnosine and lipoic acid are potent antioxidants, the applicability of which in therapy is hindered by their limited bioavailability. This study aimed to evaluate the neuroprotective properties of a nanomicellar complex of carnosine and lipoic acid (CLA) in a rotenone-induced rat model of PD. Parkinsonism was induced via the administration of 2 mg/kg rotenone over the course of 18 days. Two doses of intraperitoneal CLA (25 mg/kg and 50 mg/kg) were administered alongside rotenone to assess its neuroprotective effect. At 25 mg/kg CLA decreased muscle rigidity and partially restored locomotor activity in animals that received rotenone. Furthermore, it caused an overall increase in brain tissue antioxidant activity, accompanied by a 19% increase in neuron density in the substantia nigra and increased dopamine levels in the striatum relative to animals that only received rotenone. Based on the acquired results, it may be concluded that CLA have neuroprotective properties and could potentially be beneficial in PD treatment when used in conjunction with the base therapy. Full article

(This article belongs to the Special Issue Natural Antioxidants: Characterization, Synthetic Analogues and Potential Applications)

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19 pages, 7894 KiB

Open AccessArticle

The Role of Fucoxanthin as a Potent Nrf2 Activator via Akt/GSK-3β/Fyn Axis against Amyloid-β Peptide-Induced Oxidative Damage

by Nayoung Lee, Kumju Youn, Jeong-Hyun Yoon, Bokyung Lee, Dong Hyun Kim and Mira Jun

Antioxidants 2023, 12(3), 629; https://doi.org/10.3390/antiox12030629 - 3 Mar 2023

Cited by 5 | Viewed by 2462

Abstract

Increasing evidence is suggesting that amyloid-β peptide (Aβ), a characteristic of Alzheimer’s disease (AD), induces oxidative stress and mitochondrial dysfunction, leading to neuronal death. This study aimed to demonstrate the antioxidant and anti-apoptotic effects of fucoxanthin, a major marine carotenoid found in brown [...] Read more.

Increasing evidence is suggesting that amyloid-β peptide (Aβ), a characteristic of Alzheimer’s disease (AD), induces oxidative stress and mitochondrial dysfunction, leading to neuronal death. This study aimed to demonstrate the antioxidant and anti-apoptotic effects of fucoxanthin, a major marine carotenoid found in brown algae, against neuronal injury caused by Aβ. Non-toxic dose range of fucoxanthin (0.1–5 µM) were selected for the neuroprotective study against Aβ_25–35. The PC12 cells were pretreated with different concentrations of fucoxanthin for 1 h before being exposed to 10 µM Aβ_25–35 for another 24 h. The present results showed that fucoxanthin inhibited Aβ_25-35-induced cell death by recovering cell cycle arrest and decreasing intracellular reactive oxygen species (ROS) level. The compound enhanced mitochondrial recovery and regulated apoptosis related proteins including B-cell lymphoma 2 (Bcl-2) and Bcl-2-associated X protein (Bax) from Aβ_25-35-induced oxidative stress. Concomitantly, fucoxanthin increased the expression of nuclear factor E2-related factor 2 (Nrf2) and its downstream phase II detoxifying enzymes including NADPH: quinone oxidoreductase-1 (NQO-1), glutamate cysteine ligase modifier subunit (GCLm), and thioredoxin reductase 1 (TrxR1), whereas it decreased the expression of cytoplasmic Kelch-like ECH-associated protein 1 (Keap1). Moreover, pretreatment of fucoxanthin reduced Fyn phosphorylation via protein kinase B (Akt)-mediated inhibition of glycogen synthase kinase-3β (GSK-3β), which increased the nuclear localization of Nrf2, suggesting that the compound enhanced Nrf2 expression by the activation of upstream kinase as well as the dissociation of the Nrf2-Keap1 complex. Further validation with a specific phosphatidylinositol 3-kinase (PI3K) inhibitor LY294002 demonstrated that the fucoxanthin-mediated Nrf2 antioxidant defense system was directly associated with the Akt/GSK-3β/Fyn signaling pathway. In silico simulation revealed that the oxygen groups of fucoxanthin participated in potent interactions with target markers in the Nrf2 signaling pathway, which may affect the biological activity of target markers. Taken together, the present results demonstrated that the preventive role of fucoxanthin on Aβ-stimulated oxidative injury and apoptosis via Akt/GSK-3β/Fyn signaling pathway. This study would provide a useful approach for potential intervention for AD prevention. Full article

(This article belongs to the Special Issue Natural Antioxidants: Characterization, Synthetic Analogues and Potential Applications)

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13 pages, 1949 KiB

Open AccessArticle

3D-Printed, Liquid-Filled Capsules of Concentrated and Stabilized Polyphenol Epigallocatechin Gallate, Developed in a Clinical Trial

by Philippe-Henri Secretan, Victoire Vieillard, Olivier Thirion, Maxime Annereau, Hassane Sadou Yayé, Alain Astier, Muriel Paul, Thibaud Damy and Bernard Do

Antioxidants 2023, 12(2), 424; https://doi.org/10.3390/antiox12020424 - 9 Feb 2023

Cited by 1 | Viewed by 1747

Abstract

In vitro studies have shown that epigallocatechin gallate (EGCG), the most potent antioxidant of the green tea polyphenol catechins, is able to effectively prevent the formation of amyloid plaques and induce their clearance. However, its high chemical reactivity promotes high chemical instability, which [...] Read more.

In vitro studies have shown that epigallocatechin gallate (EGCG), the most potent antioxidant of the green tea polyphenol catechins, is able to effectively prevent the formation of amyloid plaques and induce their clearance. However, its high chemical reactivity promotes high chemical instability, which represents a major obstacle for the development of pharmaceutical forms containing solubilized EGCG, an essential condition for a better systemic passage via the oral route. After discovering that EGCG forms a deep eutectic with choline chloride, we exploited this property to formulate and patent liquid-filled capsules containing 200–800 mg of soluble EGCG in easy-to-administer sizes. The gelatin envelopes used are of the conventional type and their filling has been achieved using 3D printing technology. Not only did the EGCG-choline complex allow the formulation of hydrophilic solutions with a high concentration of active substance but it also contributed significantly to its chemical stability, since after at least 18 months of storage at 25 °C/60% RH and one year at 40 °C/75% RH, the capsules show unchanged hardness, chromatographic profiles and antioxidant activity compared to T0. Preclinical studies in monkeys showed that bioavailability was increased by a factor of 10 compared to marketed capsules comprising EGCG powder. This pharmaceutical development was conducted in the context of upcoming clinical trials to evaluate EGCG alone or in combination when treating transthyretin and light-chain cardiac amyloidosis. Full article

(This article belongs to the Special Issue Natural Antioxidants: Characterization, Synthetic Analogues and Potential Applications)

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16 pages, 1899 KiB

Open AccessArticle

Comprehensive Characterization of Chemical Composition and Antioxidant Activity of Lignan-Rich Coniferous Knotwood Extractives

by Nikolay V. Ul’yanovskii, Aleksandra A. Onuchina, Anna V. Faleva, Natalia S. Gorbova and Dmitry S. Kosyakov

Antioxidants 2022, 11(12), 2338; https://doi.org/10.3390/antiox11122338 - 25 Nov 2022

Cited by 5 | Viewed by 1560

Abstract

A knotwood of coniferous trees containing large amounts of polyphenolic extractives is considered a promising industrial-scale source of lignans possessing antioxidant properties and other bioactivities. The present study is aimed at a detailed characterization of the chemical composition and antioxidant activity of lignan-rich [...] Read more.

A knotwood of coniferous trees containing large amounts of polyphenolic extractives is considered a promising industrial-scale source of lignans possessing antioxidant properties and other bioactivities. The present study is aimed at a detailed characterization of the chemical composition and antioxidant activity of lignan-rich extractives obtained from the knotwood of the Norway spruce, Scotch pine, Siberian fir, and Siberian larch growing in the European North of Russia as a region with a highly developed forest industry. To achieve this, a comprehensive approach based on a combination of two-dimensional NMR spectroscopy with high-performance liquid chromatography—high-resolution Orbitrap mass spectrometry, and the determination of antioxidant activity by the three complementary methods were proposed. The studied knotwood samples contained from 3.9 to 17% of extractive substances and were comparable to Trolox’s antioxidant activity in the single-electron transfer processes and superoxide radical scavenging, which is associated with the predominance of polyphenolic compounds. The latter was represented by 12 tentatively identified monolignans and 27 oligolignans containing 3–5 phenylpropane units in their structure. The extracts were characterized by an identical set of lignans and differed only in the ratios of their individual compounds. Other components of the knotwood were flavonoids taxifolin, quercetin (Siberian larch), and three stilbenes (pinosylvin, its methyl ester, and pterostilbene), which were identified in the Scotch pine extractives. Sesquiterpene juvabione and its derivatives were found in extracts of Siberian larch knotwood. Full article

(This article belongs to the Special Issue Natural Antioxidants: Characterization, Synthetic Analogues and Potential Applications)

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16 pages, 1417 KiB

Open AccessArticle

Impact of Phenol-Enriched Olive Oils on Serum Metabonome and Its Relationship with Cardiometabolic Parameters: A Randomized, Double-Blind, Cross-Over, Controlled Trial

by Marta Farràs, Jonathan Richard Swann, Ian Rowland, Laura Rubió, Isaac Subirana, Úrsula Catalán, Maria José Motilva, Rosa Solà, Maria Isabel Covas, Francisco Blanco-Vaca, Montserrat Fitó and Jordi Mayneris-Perxachs

Antioxidants 2022, 11(10), 1964; https://doi.org/10.3390/antiox11101964 - 30 Sep 2022

Cited by 2 | Viewed by 1907

Abstract

Phenol-rich foods consumption such as virgin olive oil (VOO) has been shown to have beneficial effects on cardiovascular diseases. The broader biochemical impact of VOO and phenol-enriched OOs remains, however, unclear. A randomized, double-blind, cross-over, controlled trial was performed with thirty-three hypercholesterolemic individuals [...] Read more.

Phenol-rich foods consumption such as virgin olive oil (VOO) has been shown to have beneficial effects on cardiovascular diseases. The broader biochemical impact of VOO and phenol-enriched OOs remains, however, unclear. A randomized, double-blind, cross-over, controlled trial was performed with thirty-three hypercholesterolemic individuals who ingested for 3-weeks (25 mL/day): (1) an OO enriched with its own olive oil phenolic compounds (PCs) (500 ppm; FOO); (2) an OO enriched with its own olive oil PCs (250 ppm) plus thyme PCs (250 ppm; FOOT); and (3) a VOO with low phenolic content (80 ppm). Serum lipid and glycemic profiles, serum ¹H-NMR spectroscopy-based metabolomics, endothelial function, blood pressure, and cardiovascular risk were measured. We combined OPLS-DA with machine learning modelling to identify metabolites discrimination of the treatment groups. Both phenol-enriched OO interventions decreased the levels of glutamine, creatinine, creatine, dimethylamine, and histidine in comparison to VOO one. In addition, FOOT decreased the plasma levels of glycine and DMSO2 compared to VOO, while FOO decreased the circulating alanine concentrations but increased the plasma levels of acetone and 3-HB compared to VOO. Based on these findings, phenol-enriched OOs were shown to result in a favorable shift in the circulating metabolic phenotype, inducing a reduction in metabolites associated with cardiometabolic diseases. Full article

(This article belongs to the Special Issue Natural Antioxidants: Characterization, Synthetic Analogues and Potential Applications)

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14 pages, 1298 KiB

Open AccessArticle

Inhibitory Effect on Nitric Oxide Release in LPS-Stimulated Macrophages and Free Radical Scavenging Activity of Croton linearis Jacq. Leaves

by Jesús García Díaz, Rosalia González Fernández, Julio César Escalona Arranz, Gabriel Llauradó Maury, Daniel Méndez Rodríguez, Linda De Vooght, Enrique Molina, Emmy Tuenter, Luc Pieters and Paul Cos

Antioxidants 2022, 11(10), 1915; https://doi.org/10.3390/antiox11101915 - 27 Sep 2022

Cited by 1 | Viewed by 1795

Abstract

Oxidative stress is an important component of many diseases including cancer, along with inflammatory and neurodegenerative processes. Natural antioxidants have emerged as promising substances to protect the human body against reactive oxygen and nitrogen species. The present study evaluates the inhibition of nitric [...] Read more.

Oxidative stress is an important component of many diseases including cancer, along with inflammatory and neurodegenerative processes. Natural antioxidants have emerged as promising substances to protect the human body against reactive oxygen and nitrogen species. The present study evaluates the inhibition of nitric oxide (NO) production in LPS-stimulated RAW 264.7 murine macrophages and the free radical scavenging activity of Croton linearis Jacq. leaves. UPLC-QTOF-MS analysis identified 18 compounds: nine alkaloids with a morphinane, benzylisoquinoline or aporphine nucleus, and nine O-glycosylated-flavonoids with quercetin, kaempferol and isorhamnetin as the aglycones. The crude extract (IC₅₀ 21.59 µg/mL) and the n-hexane fraction (IC₅₀ 4.88 µg/mL) significantly reduced the NO production in LPS-stimulated macrophages but with relatively high cytotoxicity (CC₅₀ 75.30 and CC₅₀ 70.12 µg/mL, respectively), while the ethyl acetate fraction also showed good activity (IC₅₀ 40.03 µg/mL) without affecting the RAW 264.7 cell viability. On the other hand, the crude extract, as well as the dichloromethane and ethyl acetate fractions, showed better DPPH and ABTS free radical scavenging activities. Considering the chemical composition and the activity observed for Croton linearis leaves, they may be considered a good source of antioxidants to combat oxidative damage-related diseases. Full article

(This article belongs to the Special Issue Natural Antioxidants: Characterization, Synthetic Analogues and Potential Applications)

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16 pages, 1842 KiB

Open AccessArticle

Structural Characterization of Peripolin and Study of Antioxidant Activity of HMG Flavonoids from Bergamot Fruit

by Lucia Bartella, Fabio Mazzotti, Ines Rosita Talarico, Giuseppina De Luca, Ilaria Santoro, Mario Prejanò, Costanza Riccioni, Tiziana Marino and Leonardo Di Donna

Antioxidants 2022, 11(10), 1847; https://doi.org/10.3390/antiox11101847 - 20 Sep 2022

Cited by 8 | Viewed by 1874

Abstract

The structural characterization of a new flavonoid from bergamot fruit (Citrus bergamia Risso) carrying the 3-hydroxy-3-methyl glutaryl (HMG) ester moiety has been accomplished, and its antioxidant ability was tested from a chemical point of view. The peculiarity of the new molecule, named peripolin, [...] Read more.

The structural characterization of a new flavonoid from bergamot fruit (Citrus bergamia Risso) carrying the 3-hydroxy-3-methyl glutaryl (HMG) ester moiety has been accomplished, and its antioxidant ability was tested from a chemical point of view. The peculiarity of the new molecule, named peripolin, relies on the presence of the HMG chemical group linked to the sugar portion of neoeriocitrin; the structure was elucidated using both high-resolution mass spectrometry and nuclear magnetic resonance experiments performed on the purified molecule extracted from the fruit. The antioxidant ability of the new molecule was tested by classical chemical approaches, such as DPPH, ABTS and FRAP assays, and from a theoretical point of view. ¹H and ¹³C NMR experiments and HR-ESI-MS/MS experiments show unequivocally that the HMG moiety is linked to the primary position of the glucose unit of neohesperidose, while the chemical tests and the computational results show that peripolin possesses strong antioxidant behavior, similar to that of neoeriocitrin and remarkably higher respect to the other flavonoids present in the fruit. Furthermore, the quantitative assays carried out by UPLC-MS/MS showed that its amount in the fruit is similar to that of the other main flavonoids. Furthermore, molecular dynamics simulations allowed us to investigate the possible conformations adopted by the antioxidants in the presence of water molecules. In particular, the switch of open-closed conformations of HMG-containing species was evidenced. As far as the reaction with DPPH, the calculation of ΔG_rea supported the experimental outcomes regarding the peripolin and neoeriocitrin activity. In conclusion, bergamot fruit, already known for its potential to lower the level of blood cholesterol, has been proven to contain molecules such as neoeriocitrin and the newly characterized peripolin, which could have important in-vivo antioxidant characteristics. Full article

(This article belongs to the Special Issue Natural Antioxidants: Characterization, Synthetic Analogues and Potential Applications)

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15 pages, 1401 KiB

Open AccessArticle

Oxo-Carotenoids as Efficient Superoxide Radical Scavengers

by Gaosheng Shi, Hyein Kim and Sangho Koo

Antioxidants 2022, 11(8), 1525; https://doi.org/10.3390/antiox11081525 - 5 Aug 2022

Cited by 4 | Viewed by 1800

Abstract

Oxo-carotenoids containing conjugated carbonyl groups in their chains were designed to be more efficient superoxide radical scavengers than natural carotenoids, β-carotene and canthaxanthin. A practical chain-extension method for polyene dials (e.g., crocetin dial) was also proposed based on Horner–Wadsworth–Emmons olefination. Double aldol condensation [...] Read more.

Oxo-carotenoids containing conjugated carbonyl groups in their chains were designed to be more efficient superoxide radical scavengers than natural carotenoids, β-carotene and canthaxanthin. A practical chain-extension method for polyene dials (e.g., crocetin dial) was also proposed based on Horner–Wadsworth–Emmons olefination. Double aldol condensation between polyene dials and acetophenones with ring substituents produced oxo-carotenoids with substituted benzene rings. The antioxidant activity of oxo-carotenoids was measured using DPPH (radical) and ABTS (cationic radical) scavenging assays and compared with the analysis with the superoxide (anionic radical) probe. An effective conjugation length by carbon–carbon double bonds is important to provide superior antioxidant activity for oxo-carotenoids, regardless of the type of radical probe used in the assay. Increasing electron density is favorable to strong antioxidant activity in DPPH, and the phenol group is favored in ABTS, whereas electron deficient oxo-carotenoids are very potent in the superoxide radical assay. All oxo-carotenoids exhibited 105~151% better superoxide radical scavenging activity compared to beta-carotene (100%), whereas 38~155% in DPPH and 16~96% in ABTS radical scavenging activities were observed. Full article

(This article belongs to the Special Issue Natural Antioxidants: Characterization, Synthetic Analogues and Potential Applications)

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21 pages, 2123 KiB

Open AccessArticle

Scutellaria petiolata Hemsl. ex Lace & Prain (Lamiaceae).: A New Insight in Biomedical Therapies

by Sidra Mubin, Najeeb Ur Rehman, Waheed Murad, Muddaser Shah, Ahmed Al-Harrasi and Rabia Afza

Antioxidants 2022, 11(8), 1446; https://doi.org/10.3390/antiox11081446 - 26 Jul 2022

Cited by 5 | Viewed by 1627

Abstract

The recent investigation was designed to explore Scutellaria petiolata Hemsl. ex Lace & Prain (Lamiaceae) whole plant in various extracts (methanol (SPM), dichloromethane (SPDCM), n-Hexane (SPNH), and aqueous (SPAQ) for a phytochemicals assessment, ESI-LC-MS chemical analysis, in vitro antimicrobials, and antioxidants and in [...] Read more.

The recent investigation was designed to explore Scutellaria petiolata Hemsl. ex Lace & Prain (Lamiaceae) whole plant in various extracts (methanol (SPM), dichloromethane (SPDCM), n-Hexane (SPNH), and aqueous (SPAQ) for a phytochemicals assessment, ESI-LC-MS chemical analysis, in vitro antimicrobials, and antioxidants and in vivo anti-inflammatory and analgesic potential. The qualitative detection shows that all the representative groups were present in the analyzed samples. The examined samples display the greatest amount of total flavonoid content (TFC, 78.2 ± 0.22 mg QE/mg) and total phenolic contents (TPC, 66.2 ± 0.33 mg GAE/g) in the SPM extract. The SPM extract proceeded to the ESI-LC-MS to identify the chemical constituents that presented nineteen bioactive ingredients, depicted for the first time from S. petiolata mainly contributed by flavonoids. The analyzed samples produced considerable capability to defy the microbes. The SPM extract was observed effective and offered an appreciable zone of inhibition (ZOI), 17.8 ± 0.04 mm against the bacterial strain Salmonellatyphi and 18.8 ± 0.04 mm against Klebsiella pneumonia. Moreover, the SPM extract also exhibited 19.4 ± 0.01 mm against the bacterial strains Bacillus atrophaeus and 18.8 ± 0.04 mm against Bacillus subtilis in comparison to the standard levofloxacin (Gram-negative) and erythromycin (Gram-positive) bacterial strains that displayed 23.6 ± 0.02 mm and 23.2 ± 0.05 mm ZOI, correspondingly. In addition to that, the SPD fraction was noticed efficiently against the fungal strains used with ZOI 19.07 ± 0.02 mm against Aspergillus parasiticus and 18.87 ± 0.04 mm against the Aspergillus niger as equated to the standard with 21.5 ± 0.02 mm ZOI. In the DPPH (2,2-diphenyl-1-picrylhydrazyl) analysis, the SPM extract had the maximum scavenging capacity with IC₅₀ of 78.75 ± 0.19 µg/mL succeeded by the SPDCM fraction with an IC₅₀ of 140.50 ± 0.20 µg/mL free radicals scavenging potential. Through the ABTS (2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) assay, the similar extract (SPM) presented an IC₅₀ = 85.91 ± 0.24 µg/mL followed by the SPDCM fractions with IC₅₀ = 182.50 ± 0.35 µg/mL, and n-Hexane fractions were reported to be the least active between the tested samples in comparison to ascorbic acid of IC₅₀ = 67.14 ± 0.25 µg/mL for DPPH and IC₅₀ of 69.96 ± 0.18 µg/mL for ABTS assay. In the in vivo activities, the SPM extract was the most effective with 55.14% inhibition as compared to diclofenac sodium with 70.58% inhibition against animals. The same SPM crude extract with 50.88% inhibition had the most analgesic efficacy as compared to aspirin having 62.19% inhibition. Hence, it was assumed from our results that all the tested samples, especially the SPM and SPDCM extracts, have significant capabilities for the investigated activities that could be due to the presence of the bioactive compounds. Further research is needed to isolate the responsible chemical constituents to produce innovative medications. Full article

(This article belongs to the Special Issue Natural Antioxidants: Characterization, Synthetic Analogues and Potential Applications)

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21 pages, 1695 KiB

Open AccessArticle

Total Phenolic Content, Biomass Composition, and Antioxidant Activity of Selected Marine Microalgal Species with Potential as Aquaculture Feed

by Vasilis Andriopoulos, Maria D. Gkioni, Eleni Koutra, Savvas G. Mastropetros, Fotini N. Lamari, Sophia Hatziantoniou and Michael Kornaros

Antioxidants 2022, 11(7), 1320; https://doi.org/10.3390/antiox11071320 - 4 Jul 2022

Cited by 19 | Viewed by 3631

Abstract

There has been growing interest in microalgal biomolecules for health and cosmetics, as well as in the use of microalgae as aquaculture feed due to the need to replace fishmeal and fish oil with sustainable yet equally nutritious alternatives. Aim of this study [...] Read more.

There has been growing interest in microalgal biomolecules for health and cosmetics, as well as in the use of microalgae as aquaculture feed due to the need to replace fishmeal and fish oil with sustainable yet equally nutritious alternatives. Aim of this study is to evaluate the potential of five marine microalgal species, namely Chlorella minutissima, Dunaliella salina, Isochrysis galbana, Nannochloropsis oculata and Tisochrysis lutea, for the co-production of antioxidants and aquaculture feed. Batch cultivation was performed under saturating light intensity and continuous aeration. Freeze-dried biomass was extracted sequentially with water and methanol and evaluated for phenolic content and antioxidant activity, as well as proximate composition and fatty acid profile. Methanolic extracts of C. minutissima presented the highest phenolic content, measured with the Folin–Ciocalteu assay, and antioxidant activity. However, HPLC and LC-MS showed the presence of non-pigment compounds only in T. lutea. Total phenolic content and antioxidant activity were correlated to chlorophyll content. N. oculata and T. lutea were rich in eicosapentaenoic acid and docosahexaenoic acid, respectively, as well as in protein. In conclusion, N. oculata and T. lutea are suitable candidates for further optimization, while the data presented suggest that pigment effects on the Folin–Ciocalteu method require reconsideration. Full article

(This article belongs to the Special Issue Natural Antioxidants: Characterization, Synthetic Analogues and Potential Applications)

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16 pages, 3510 KiB

Open AccessArticle

An In Vitro and In Silico Study of Antioxidant Properties of Curcuminoid N-alkylpyridinium Salts: Initial Assessment of Their Antitumoral Properties

by Oscar Forero-Doria, Luis Guzmán, Felipe Jiménez-Aspee, Javier Echeverría, Sergio Wehinger, Claudio Valenzuela, Ramiro Araya-Maturana and Maximiliano Martínez-Cifuentes

Antioxidants 2022, 11(6), 1104; https://doi.org/10.3390/antiox11061104 - 1 Jun 2022

Cited by 6 | Viewed by 2509

Abstract

In this work, we report the synthesis of curcuminoids with ionic liquid characteristics, obtained by incorporating alkyl-substituted pyridinium moiety rather than one phenyl group through a two-step process. The antioxidant capacity of the obtained compounds was evaluated in vitro by 1,1-diphenyl-picrylhydrazyl (DPPH) free [...] Read more.

In this work, we report the synthesis of curcuminoids with ionic liquid characteristics, obtained by incorporating alkyl-substituted pyridinium moiety rather than one phenyl group through a two-step process. The antioxidant capacity of the obtained compounds was evaluated in vitro by 1,1-diphenyl-picrylhydrazyl (DPPH) free radical scavenging and ferric reducing antioxidant power (FRAP) assays, showing that some derivatives are more potent than curcumin. Pyridine curcuminoids (group 4) and curcuminoid N-alkylpyridinium salts with two methoxyl groups in the phenyl ring (group 7), presented the best antioxidant capacity. The experimental results were rationalized by density functional theory (DFT) calculations of the bond dissociation enthalpy (BDE) for O–H in each compound. The computational calculations allowed for insight into the structural–antioxidant properties relationship in these series of compounds. BDEs, obtained in the gas phase and water, showed a notable impact of water solvation on the stabilization of some radicals. The lower values of BDEs in the water solution correspond to the structurally related compounds curcuminoid-pyridine 4c and curcuminoid pyridinium salt 7a, which is consistent with the experimental results. Additionally, an assessment of cell viability and cell migration assays was performed for human colon cancer (HT29), human breast cancer (MCF7) cells, in addition to NIH3T3 murine fibroblast, as a model of non-cancer cell type. These compounds mainly cause inhibition of the cell migration observed in MCF7 cancer cells without affecting the non-tumoral NIH3T3 cell line: Neither in viability nor in migration. Full article

(This article belongs to the Special Issue Natural Antioxidants: Characterization, Synthetic Analogues and Potential Applications)

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19 pages, 1146 KiB

Open AccessArticle

Ultrasound-Assisted Extraction of Nannochloropsis oculata with Ethanol and Betaine: 1,2-Propanediol Eutectic Solvent for Antioxidant Pigment-Rich Extracts Retaining Nutritious the Residual Biomass

by Maria D. Gkioni, Vasilis Andriopoulos, Eleni Koutra, Sophia Hatziantoniou, Michael Kornaros and Fotini N. Lamari

Antioxidants 2022, 11(6), 1103; https://doi.org/10.3390/antiox11061103 - 31 May 2022

Cited by 13 | Viewed by 3379

Abstract

The aim of this study was the development of an efficient “green” extraction method of Nannochloropsis oculata to produce antioxidant extracts and nutritious residual biomass. Twenty-one extraction methods were evaluated by measuring the reactivity with the Folin–Ciocalteu reagent: ultrasonication or maceration at different [...] Read more.

The aim of this study was the development of an efficient “green” extraction method of Nannochloropsis oculata to produce antioxidant extracts and nutritious residual biomass. Twenty-one extraction methods were evaluated by measuring the reactivity with the Folin–Ciocalteu reagent: ultrasonication or maceration at different temperatures with different organic solvents, extraction at different pH values, enzyme-assisted extraction, encapsulation with β-cyclodextrin, and the use of natural deep eutectic solvents. Ultrasound-assisted extraction with ethanol or betaine: 1,2-propanediol in a molar ratio of 2:5 (BP) had optimal extractive capacity. Both extracts were evaluated with antioxidant assays and the ethanol extract exhibited significantly higher (at least twofold) values. The determination of carotenoids by LC-MS and HPLC-DAD revealed the dominance of violaxanthin and antheraxanthin and their fourfold higher concentrations in the ethanol extract. The ¹H-NMR characterization of the ethanol extract confirmed the results of the colorimetric and chromatographic assays. The microalgal biomass was characterized before and after the extraction in terms of humidity, ash, carbohydrates, proteins, chlorophyll-a, carotenoids, and lipids; the identity and content of the latter were determined with gas chromatography. BP caused a smaller depletion of the lipids from the biomass compared to ethanol, but proteins, carbohydrates, and ash were at a higher content in the biomass obtained after ethanol extraction, whereas the biomass was dry and easy to handle. Although further optimization may take place for the scale-up of those procedures, our study paves the way for a green strategy for the valorization of microalgae in cosmetics without generating waste, since the remaining biomass can be used for aquafeed. Full article

(This article belongs to the Special Issue Natural Antioxidants: Characterization, Synthetic Analogues and Potential Applications)

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19 pages, 4309 KiB

Open AccessArticle

High-Yield Production of a Rich-in-Hydroxytyrosol Extract from Olive (Olea europaea) Leaves

by Costas S. Papageorgiou, Paraskevi Lyri, Ioanna Xintaropoulou, Ioannis Diamantopoulos, Dimitris P. Zagklis and Christakis A. Paraskeva

Antioxidants 2022, 11(6), 1042; https://doi.org/10.3390/antiox11061042 - 24 May 2022

Cited by 10 | Viewed by 2228

Abstract

The aim of the present study was to explore the high-yield production of hydroxytyrosol, a phenolic compound with very high antioxidant capacity. Olea europaea leaves were chosen as feedstock as they contain significant amounts of oleuropein, which can be hydrolyzed to hydroxytyrosol. The [...] Read more.

The aim of the present study was to explore the high-yield production of hydroxytyrosol, a phenolic compound with very high antioxidant capacity. Olea europaea leaves were chosen as feedstock as they contain significant amounts of oleuropein, which can be hydrolyzed to hydroxytyrosol. The chosen techniques are widely used in the industry and can be easily scaled up. Olive leaves underwent drying and mechanical pretreatment and extractives were transported to a solvent by solid–liquid extraction using water–ethanol mixtures. The use of approximately 60–80% ethanol showed an almost 2-fold increase in extracted phenolics compared to pure water, to approximately 45 g/kg of dry leaves. Extracted oleuropein was hydrolyzed with hydrochloric acid and the hydrolysate was extracted with ethyl acetate after pH adjustment. This step led to a hydroxytorosol content increase from less than 4% to approximately 60% w/w of dry extract, or 10–15 g of hydroxytyrosol recovery per kg of dry leaves. Full article

(This article belongs to the Special Issue Natural Antioxidants: Characterization, Synthetic Analogues and Potential Applications)

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Algal Metabolites Can Be an Immune Booster against COVID-19 Pandemic

by Ajay Kumar, Rahul Prasad Singh, Indrajeet Kumar, Priya Yadav, Sandeep Kumar Singh, Kaushalendra, Prashant Kumar Singh, Rajan Kumar Gupta, Shiv Mohan Singh, Mahipal Singh Kesawat, Ganesh Dattatraya Saratale, Sang-Min Chung and Manu Kumar

Antioxidants 2022, 11(3), 452; https://doi.org/10.3390/antiox11030452 - 24 Feb 2022

Cited by 9 | Viewed by 4705

Abstract

The world has faced the challenges of Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2) for the last two years, first diagnosed at the end of 2019 in Wuhan and widely distributed worldwide. As a result, the WHO has proclaimed the illness brought on [...] Read more.

The world has faced the challenges of Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2) for the last two years, first diagnosed at the end of 2019 in Wuhan and widely distributed worldwide. As a result, the WHO has proclaimed the illness brought on by this virus to be a global pandemic. To combat COVID-19, researcher communities continuously develop and implement rapid diagnoses, safe and effective vaccinations and other alternative therapeutic procedures. However, synthetic drug-related side effects and high costs have piqued scientists’ interest in natural product-based therapies and medicines. In this regard, antiviral substances derived from natural resources and some medicines have seen a boom in popularity. For instance, algae are a rich source of compounds such as lectins and sulfated polysaccharides, which have potent antiviral and immunity-boosting properties. Moreover, Algae-derived compounds or metabolites can be used as antibodies and vaccine raw materials against COVID-19. Furthermore, some algal species can boost immunity, reduce viral activity in humans and be recommended for usage as a COVID-19 preventative measure. However, this field of study is still in its early stages of development. Therefore, this review addresses critical characteristics of algal metabolites, their antioxidant potential and therapeutic potential in COVID-19. Full article

(This article belongs to the Special Issue Natural Antioxidants: Characterization, Synthetic Analogues and Potential Applications)

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