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4 pages, 210 KiB

Open AccessEditorial

The Antioxidant Capacities of Natural Products 2019

by Susana M. Cardoso and Alessia Fazio

Molecules 2020, 25(23), 5676; https://doi.org/10.3390/molecules25235676 - 1 Dec 2020

Cited by 8 | Viewed by 2120

Abstract

The search for new natural antioxidants is a growing area of research due to the broad spectrum of their biological properties, which are associated with the prevention of chronic diseases that originate in oxidative stress [...] Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

Research

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14 pages, 1275 KiB

Open AccessArticle

Characterization and Antioxidant Activity Determination of Neutral and Acidic Polysaccharides from Panax Ginseng C. A. Meyer

by Hyung Min Kim, Yanxue Song, Gyu Hwan Hyun, Nguyen Phuoc Long, Jeong Hill Park, Yves S.Y. Hsieh and Sung Won Kwon

Molecules 2020, 25(4), 791; https://doi.org/10.3390/molecules25040791 - 12 Feb 2020

Cited by 44 | Viewed by 5126

Abstract

Panax ginseng (P. ginseng) is the most widely consumed herbal plant in Asia and is well-known for its various pharmacological properties. Many studies have been devoted to this natural product. However, polysaccharide’s components of ginseng and their biological effects have not [...] Read more.

Panax ginseng (P. ginseng) is the most widely consumed herbal plant in Asia and is well-known for its various pharmacological properties. Many studies have been devoted to this natural product. However, polysaccharide’s components of ginseng and their biological effects have not been widely studied. In this study, white ginseng neutral polysaccharide (WGNP) and white ginseng acidic polysaccharide (WGAP) fractions were purified from P. ginseng roots. The chemical properties of WGNP and WGAP were investigated using various chromatography and spectroscopy techniques, including high-performance gel permeation chromatography, Fourier-transform infrared spectroscopy, and high-performance liquid chromatography with an ultra-violet detector. The antioxidant, anti-radical, and hydrogen peroxide scavenging activities were evaluated in vitro and in vivo using Caenorhabditis elegans as the model organism. Our in vitro data by ABTS (2,2′-azino-bis-(3-ethylbenzothiazoline-6-sulfonic acid), reducing power, ferrous ion chelating, and hydroxyl radical scavenging activity suggested that the WGAP with significantly higher uronic acid content and higher molecular weight exhibits a much stronger antioxidant effect as compared to that of WGNP. Similar antioxidant activity of WGAP was also confirmed in vivo by evaluating internal reactive oxygen species (ROS) concentration and lipid peroxidation. In conclusion, WGAP may be used as a natural antioxidant with potent scavenging and metal chelation properties. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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28 pages, 373 KiB

Open AccessFeature PaperArticle

The Effects of Biostimulants, Biofertilizers and Water-Stress on Nutritional Value and Chemical Composition of Two Spinach Genotypes (Spinacia oleracea L.)

by Carla Pereira, Maria Inês Dias, Spyridon A. Petropoulos, Sofia Plexida, Antonios Chrysargyris, Nikos Tzortzakis, Ricardo C. Calhelha, Marija Ivanov, Dejan Stojković, Marina Soković, Lillian Barros and Isabel C.F.R. Ferreira

Molecules 2019, 24(24), 4494; https://doi.org/10.3390/molecules24244494 - 8 Dec 2019

Cited by 43 | Viewed by 5836

Abstract

In the present study, the effect of biostimulants application on the nutritional quality and bioactive properties of spinach cultivated in protected environment under water stress conditions was evaluated. For this purpose, four commercially available biostimulant products (Megafol (MEG), Aminovert (AM), Veramin Ca (V), [...] Read more.

In the present study, the effect of biostimulants application on the nutritional quality and bioactive properties of spinach cultivated in protected environment under water stress conditions was evaluated. For this purpose, four commercially available biostimulant products (Megafol (MEG), Aminovert (AM), Veramin Ca (V), Twin Antistress (TA), and two spinach genotypes (Fuji F1 and Viroflay) were tested under two irrigation regimes (normal irrigation (W+), and water-holding (W–). Fat and carbohydrates content was favored by water stress when Megafol (MEGW+) and Veramin (VW+) were applied on Fuji plants, while calorific value was also increased by MEGW+ treatment. In contrast, protein and ash content increased when AMW– and TAW+ were applied on Viroflay plants. Raffinose and glucose were the most abundant sugars, followed by sucrose and fructose, with the highest contents recorded for Fuji plants when AMW+ (fructose, glucose and total carbohydrates), CW– (sucrose), and TAW– (raffinose) treatments were applied. Regarding organic acids, oxalic and malic acid which had the highest contents for the TAW– (Viroflay plants) and AMW– (Fuji plants) treatments, respectively. α- and γ-tocopherol were the only isoforms detected with MEGW– and VW– inducing the biosynthesis of α-tocopherol, while AMW+ increased γ-tocopherol content in Fuji plants. The main fatty acids were α-linolenic and linoleic acids which were detected in the highest amounts in AMW–, AMW+, and TAW+ the former and in AMW–, VW–, and CW+ the latter. Regarding phenolic compounds content, peak 12 (5,3′,4′-Trihydroxy-3-methoxy-6:7-methylenedioxyflavone-4′-glucuronide) was the most abundant compound, especially in Viroflay plants under normal irrigation and no biostimulants added (CW–). The antioxidant and cytotoxic activity of the tested samples did not show promising results when compared with the positive controls, while a variable antibacterial activity was recorded depending on the tested biostimulant, irrigation regime and genotype. In conclusion, a variable effect of the tested biostimulants and irrigation regimes was observed on bioactive properties and chemical composition of both spinach genotypes which highlights the need for further research in order to make profound conclusions regarding the positive effects of biostimulants under water stress conditions. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

13 pages, 609 KiB

Open AccessArticle

Phytochemical Composition and Bioactive Effects of Salvia africana, Salvia officinalis ‘Icterina’ and Salvia mexicana Aqueous Extracts

by Andrea F. Afonso, Olívia R. Pereira, Ângela Fernandes, Ricardo C. Calhelha, Artur M. S. Silva, Isabel C.F.R. Ferreira and Susana M. Cardoso

Molecules 2019, 24(23), 4327; https://doi.org/10.3390/molecules24234327 - 27 Nov 2019

Cited by 59 | Viewed by 6992

Abstract

In the present study, aqueous extracts of Salvia africana, Salvia officinalis ‘Icterina’ and Savia mexicana origin were screened for their phenolic composition and for antibacterial, antioxidant, anti-inflammatory and cytotoxic properties. The three aqueous extracts contained distinct phenolic compounds, with S. africana presenting [...] Read more.

In the present study, aqueous extracts of Salvia africana, Salvia officinalis ‘Icterina’ and Savia mexicana origin were screened for their phenolic composition and for antibacterial, antioxidant, anti-inflammatory and cytotoxic properties. The three aqueous extracts contained distinct phenolic compounds, with S. africana presenting the highest total levels (231.6 ± 7.5 μg/mg). Rosmarinic acid was the dominant phenolic compound in all extracts, yet that of S. africana origin was characterized by the present of yunnaneic acid isomers, which overall accounted for about 40% of total phenolics. In turn, S. officinalis ‘Icterina’ extract presented glycosidic forms of apigenin, luteolin and scuttelarein, and the one obtained from S. mexicana contained several simple caffeic acid derivatives. S. africana aqueous extract exhibited high antioxidant potential in four methods, namely the DPPH^• (2,2-diphenyl-1-picrylhydrazyl) scavenging ability, iron-reducing power, inhibition of β-carotene bleaching and of thiobarbituric acid reactive substances (TBARS), for which EC₅₀ values were equal or only 1.3–3.1 higher than those of the standard compounds. Moreover, this extract was able to lower the levels of nitric oxide (NO) production in lipopolysaccharide (LPS)-activated RAW 264.7 macrophages (EC₅₀ = 47.8 ± 2.1 μg/mL). In addition, the three sage aqueous extracts showed promising cytotoxic effect towards hepatocellular HepG2, cervical HeLa, and breast carcinoma cells MCF-7. Overall this study highlights the potential of three little-exploited Salvia species, with commercial value for applications in food or pharmaceutical industries. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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31 pages, 6764 KiB

Open AccessArticle

Carnosic Acid Attenuates Cadmium Induced Nephrotoxicity by Inhibiting Oxidative Stress, Promoting Nrf2/HO-1 Signalling and Impairing TGF-β1/Smad/Collagen IV Signalling

by Sonjit Das, Saikat Dewanjee, Tarun K. Dua, Swarnalata Joardar, Pratik Chakraborty, Shovonlal Bhowmick, Achintya Saha, Simanta Bhattacharjee and Vincenzo De Feo

Molecules 2019, 24(22), 4176; https://doi.org/10.3390/molecules24224176 - 18 Nov 2019

Cited by 42 | Viewed by 4988

Abstract

Cadmium (Cd) imparts nephrotoxicity via triggering oxidative stress and pathological signal transductions in renal cells. The present study was performed to explore the protective mechanism of carnosic acid (CA), a naturally occurring antioxidant compound, against cadmium chloride (CdCl₂)-provoked nephrotoxicity employing suitable [...] Read more.

Cadmium (Cd) imparts nephrotoxicity via triggering oxidative stress and pathological signal transductions in renal cells. The present study was performed to explore the protective mechanism of carnosic acid (CA), a naturally occurring antioxidant compound, against cadmium chloride (CdCl₂)-provoked nephrotoxicity employing suitable in vitro and in vivo assays. CA (5 µM) exhibited an anti-apoptotic effect against CdCl₂ (40 µM) in normal kidney epithelial (NKE) cells evidenced from cell viability, image, and flow cytometry assays. In this study, CdCl₂ treatment enhanced oxidative stress by triggering free radical production, suppressing the endogenous redox defence system, and inhibiting nuclear factor erythroid 2-related factor 2 (Nrf2) activation in NKE cells and mouse kidneys. Moreover, CdCl₂ treatment significantly endorsed apoptosis and fibrosis via activation of apoptotic and transforming growth factor (TGF)-β1/mothers against decapentaplegic homolog (Smad)/collagen IV signalling pathways, respectively. In contrast, CA treatment significantly attenuated Cd-provoked nephrotoxicity via inhibiting free radicals, endorsing redox defence, suppressing apoptosis, and inhibiting fibrosis in renal cells in both in vitro and in vivo systems. In addition, CA treatment significantly (p < 0.05–0.01) restored blood and urine parameters to near-normal levels in mice. Histological findings further confirmed the protective role of CA against Cd-mediated nephrotoxicity. Molecular docking predicted possible interactions between CA and Nrf2/TGF-β1/Smad/collagen IV. Hence, CA was found to be a potential therapeutic agent to treat Cd-mediated nephrotoxicity. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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18 pages, 4914 KiB

Open AccessArticle

Effect of Methyl Jasmonate on Phenolic Accumulation in Wounded Broccoli

by Yuge Guan, Wenzhong Hu, Aili Jiang, Yongping Xu, Rengaowa Sa, Ke Feng, Manru Zhao, Jiaoxue Yu, Yaru Ji, Mengyang Hou and Xiaozhe Yang

Molecules 2019, 24(19), 3537; https://doi.org/10.3390/molecules24193537 - 30 Sep 2019

Cited by 45 | Viewed by 3995

Abstract

In order to find an efficient way for broccoli to increase the phenolic content, this study intended primarily to elucidate the effect of methyl jasmonate (MeJA) treatment on the phenolic accumulation in broccoli. The optimum concentration of MeJA was studied first, and 10 [...] Read more.

In order to find an efficient way for broccoli to increase the phenolic content, this study intended primarily to elucidate the effect of methyl jasmonate (MeJA) treatment on the phenolic accumulation in broccoli. The optimum concentration of MeJA was studied first, and 10 μM MeJA was chosen as the most effective concentration to improve the phenolic content in wounded broccoli. Furthermore, in order to elucidate the effect of methyl jasmonate (MeJA) treatment on phenolic biosynthesis in broccoli, the key enzyme activities of phenylpropanoid metabolism, the total phenolic content (TPC), individual phenolic compounds (PC), antioxidant activity (AOX) and antioxidant metabolism-associated enzyme activities were investigated. Results show that MeJA treatment stimulated phenylalanine ammonia-lyase (PAL), cinnamate 4-hydroxylase (C4H), and 4-coumarin coenzyme A ligase (4CL) enzymes activities in phenylpropanoid metabolism, and inhibited the activity of polyphenol oxidase (PPO), and further accelerated the accumulation of the wound-induced rutin, caffeic acid, and cinnamic acid accumulation, which contributed to the result of the total phenolic content increasing by 34.8% and ferric reducing antioxidant power increasing by 154.9% in broccoli. These results demonstrate that MeJA in combination with wounding stress can induce phenylpropanoid metabolism for the wound-induced phenolic accumulation in broccoli. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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15 pages, 3707 KiB

Open AccessArticle

Antioxidant Activity of an Aqueous Leaf Extract from Uncaria tomentosa and Its Major Alkaloids Mitraphylline and Isomitraphylline in Caenorhabditis elegans

by Bruna C. Azevedo, Mariana Roxo, Marcos C. Borges, Herbenya Peixoto, Eduardo J. Crevelin, Bianca W. Bertoni, Silvia H. T. Contini, Adriana A. Lopes, Suzelei C. França, Ana M. S. Pereira and Michael Wink

Molecules 2019, 24(18), 3299; https://doi.org/10.3390/molecules24183299 - 10 Sep 2019

Cited by 36 | Viewed by 5696

Abstract

Uncaria tomentosa (Rubiaceae) has a recognized therapeutic potential against various diseases associated with oxidative stress. The aim of this research was to evaluate the antioxidant potential of an aqueous leaf extract (ALE) from U. tomentosa, and its major alkaloids mitraphylline and isomitraphylline. [...] Read more.

Uncaria tomentosa (Rubiaceae) has a recognized therapeutic potential against various diseases associated with oxidative stress. The aim of this research was to evaluate the antioxidant potential of an aqueous leaf extract (ALE) from U. tomentosa, and its major alkaloids mitraphylline and isomitraphylline. The antioxidant activity of ALE was investigated in vitro using standard assays (DPPH, ABTS and FRAP), while the in vivo activity and mode of action were studied using Caenorhabditis elegans as a model organism. The purified alkaloids did not exhibit antioxidant effects in vivo. ALE reduced the accumulation of reactive oxygen species (ROS) in wild-type worms, and was able to rescue the worms from a lethal dose of the pro-oxidant juglone. The ALE treatment led to a decreased expression of the oxidative stress response related genes sod-3, gst-4, and hsp-16.2. The treatment of mutant worms lacking the DAF-16 transcription factor with ALE resulted in a significant reduction of ROS levels. Contrarily, the extract had a pro-oxidant effect in the worms lacking the SKN-1 transcription factor. Our results suggest that the antioxidant activity of ALE in C. elegans is independent of its alkaloid content, and that SKN-1 is required for ALE-mediated stress resistance. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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16 pages, 1744 KiB

Open AccessArticle

Chemical Composition and Antioxidant Properties of Essential Oils from Peppermint, Native Spearmint and Scotch Spearmint

by Zhaohai Wu, Bie Tan, Yanhong Liu, James Dunn, Patricia Martorell Guerola, Marta Tortajada, Zhijun Cao and Peng Ji

Molecules 2019, 24(15), 2825; https://doi.org/10.3390/molecules24152825 - 2 Aug 2019

Cited by 111 | Viewed by 9042

Abstract

Natural antioxidants have drawn growing interest for use in animal feed and the food industry. In the current study, essential oils (EOs) obtained from hydrodistillation of three mentha species, including Mentha piperita (peppermint), Mentha spicata (native spearmint) and Mentha gracilis (Scotch spearmint), harvested [...] Read more.

Natural antioxidants have drawn growing interest for use in animal feed and the food industry. In the current study, essential oils (EOs) obtained from hydrodistillation of three mentha species, including Mentha piperita (peppermint), Mentha spicata (native spearmint) and Mentha gracilis (Scotch spearmint), harvested in the Midwest region in the United States, were analyzed for their chemical composition using gas chromatography-mass spectrometry, and their antioxidant properties were assessed through chemical assays, in vitro cell culture modeling and in Caenorhabditis elegans (C. elegans). The activity of ferric iron reduction and free-radical scavenging capacity were assessed through chemical-based assays, including the reducing power assay, 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay, and Trolox equivalent antioxidant capacity assay (TEAC). Subsequently, the capacity of EOs to mitigate lipid peroxidation was analyzed at various doses using fresh liver homogenates from pigs. A porcine jejunum epithelial cell line (IPEC-J2) was employed as in vitro model to study the cellular antioxidant activity of the mint EOs. Finally, the effectiveness of mint EOs to alleviate acute systemic oxidative damage were evaluated in vivo using C. elegans. Data were analyzed by the MIXED procedure of SAS. Contrast statement was performed to assess linear or quadratic effects of mint EOs given at various doses. All three EOs are mostly composed of monoterpenes and their derivatives (76–90%), but differed in the major compounds, which are menthol and menthone (50%) in peppermint EO and carvone (70%) in spearmint EOs. Three mint EOs demonstrated prominent radical scavenging and Fe³⁺ reducing activity in chemical-based assays. In comparison with native and Scotch spearmint EOs, peppermint EO had the lowest (p < 0.05) half maximal effective concentration (EC50) in DPPH and TEAC assays and higher efficacy in the reducing power assay. All three EOs exhibited equivalent activity in mitigation of chemical-induced lipid peroxidation in liver tissues in a dose-dependent manner (linear, p < 0.001). The maximal cellular antioxidant activity (CAA) was observed at 5 µg/mL for peppermint, and 100 µg/mL for native and Scotch spearmint EOs. The addition of 25 µg/mL of both spearmint EOs increased (p < 0.05) cellular concentrations of glutathione in H₂O₂-treated IPEC-J2 cells, suggesting enhanced endogenous antioxidant defense. Supplementation of 100 µg/mL of peppermint or Scotch spearmint EO significantly increased (p < 0.05) the survival rate of C. elegans in response to H₂O₂-induced oxidative stress. The protective effect is comparable to that of supplementation of 10 µg/mL of ascorbic acid. However native spearmint EO failed to reduce the death rate within the same supplementation dose (10–200 μg/mL). Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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13 pages, 1006 KiB

Open AccessArticle

Sorbus domestica Leaf Extracts and Their Activity Markers: Antioxidant Potential and Synergy Effects in Scavenging Assays of Multiple Oxidants

by Magdalena Rutkowska, Monika Anna Olszewska, Joanna Kolodziejczyk-Czepas, Pawel Nowak and Aleksandra Owczarek

Molecules 2019, 24(12), 2289; https://doi.org/10.3390/molecules24122289 - 20 Jun 2019

Cited by 30 | Viewed by 4013

Abstract

Sorbus domestica leaves are a traditionally used herbal medicine recommended for the treatment of oxidative stress-related diseases. Dry leaf extracts (standardized by LC-MS/MS and LC-PDA) and nine model activity markers (polyphenols), were tested in scavenging assays towards six in vivo-relevant oxidants (O₂ [...] Read more.

Sorbus domestica leaves are a traditionally used herbal medicine recommended for the treatment of oxidative stress-related diseases. Dry leaf extracts (standardized by LC-MS/MS and LC-PDA) and nine model activity markers (polyphenols), were tested in scavenging assays towards six in vivo-relevant oxidants (O₂^•−, OH^•, NO^•, H₂O₂, ONOO⁻, HClO). Ascorbic acid (AA) and Trolox (TX) were used as positive standards. The most active extracts were the diethyl ether and ethyl acetate fractions with activities in the range of 3.61–20.03 µmol AA equivalents/mg, depending on the assay. Among the model compounds, flavonoids were especially effective in OH^• scavenging, while flavan-3-ols were superior in O₂^•− quenching. The most active constituents were quercetin, (−)-epicatechin, procyanidins B2 and C1 (3.94–24.16 µmol AA/mg), but considering their content in the extracts, isoquercitrin, (−)-epicatechin and chlorogenic acid were indicated as having the greatest influence on extract activity. The analysis of the synergistic effects between those three compounds in an O₂^•− scavenging assay demonstrated that the combination of chlorogenic acid and isoquercitrin exerts the greatest influence. The results indicate that the extracts possess a strong and broad spectrum of antioxidant capacity and that their complex composition plays a key role, with various constituents acting complementarily and synergistically. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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16 pages, 3431 KiB

Open AccessArticle

Comparison of Functional Components and Antioxidant Activity of Lycium barbarum L. Fruits from Different Regions in China

by Youyuan Lu, Sheng Guo, Fang Zhang, Hui Yan, Da-Wei Qian, Han-Qing Wang, Ling Jin and Jin-Ao Duan

Molecules 2019, 24(12), 2228; https://doi.org/10.3390/molecules24122228 - 14 Jun 2019

Cited by 67 | Viewed by 4481

Abstract

The fruit of Lycium barbarum L. (FLB) has been used as medicines and functional foods for more than 2000 years in East Asia. In this study, carotenoid, phenolic, flavonoid, and polysaccharide contents as well as the antioxidant activities of FLB from 13 different [...] Read more.

The fruit of Lycium barbarum L. (FLB) has been used as medicines and functional foods for more than 2000 years in East Asia. In this study, carotenoid, phenolic, flavonoid, and polysaccharide contents as well as the antioxidant activities of FLB from 13 different regions in China from a total of 78 samples were analyzed. The results showed that total carotenoid contents ranged from 12.93 to 25.35 mg β-carotene equivalents/g DW. Zeaxanthin dipalmitate was the predominant carotenoid (4.260–10.07 mg/g DW) in FLB. The total phenolic, total flavonoid, and total polysaccharide contents ranged from 6.899 to 8.253 mg gallic acid equivalents/g DW, 3.177 to 6.144 mg rutin equivalents/g DW, and 23.62 to 42.45 mg/g DW, respectively. Rutin content ranged from 0.1812 to 0.4391 mg/g DW, and ferulic acid content ranged from 0.0994 to 0.1726 mg/g DW. All of these FLB could be divided into two clusters with PCA analysis, and both individual carotenoids and total carotenoid contents could be used as markers for regional characterization. The phenolic components were the main substance for the antioxidant activity of FLB. Considering the functional component and antioxidant activities, FLB produced in Guyuan of Ningxia was the closest to Daodi herbs (Zhongwei of Ningxia), which is commercially available high quality FLB. The results of this study could provide guidance for comprehensive applications of FLB production in different regions. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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10 pages, 2373 KiB

Open AccessArticle

3′,8″-Dimerization Enhances the Antioxidant Capacity of Flavonoids: Evidence from Acacetin and Isoginkgetin

by Xican Li, Xiaojian Ouyang, Rongxin Cai and Dongfeng Chen

Molecules 2019, 24(11), 2039; https://doi.org/10.3390/molecules24112039 - 28 May 2019

Cited by 44 | Viewed by 3503

Abstract

To probe the effect of 3′,8″-dimerization on antioxidant flavonoids, acacetin and its 3′,8″-dimer isoginkgetin were comparatively analyzed using three antioxidant assays, namely, the ·O₂⁻ scavenging assay, the Cu²⁺ reducing assay, and the 2,2′-azino bis(3-ethylbenzothiazolin-6-sulfonic acid) radical scavenging assay. In [...] Read more.

To probe the effect of 3′,8″-dimerization on antioxidant flavonoids, acacetin and its 3′,8″-dimer isoginkgetin were comparatively analyzed using three antioxidant assays, namely, the ·O₂⁻ scavenging assay, the Cu²⁺ reducing assay, and the 2,2′-azino bis(3-ethylbenzothiazolin-6-sulfonic acid) radical scavenging assay. In these assays, acacetin had consistently higher IC₅₀ values than isoginkgetin. Subsequently, the acacetin was incubated with 4-methoxy-2,2,6,6-tetramethylpiperidine-1-oxy radicals (4-methoxy-TEMPO) and then analyzed by ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UHPLC−ESI−Q−TOF−MS) technology. The results of the UHPLC−ESI−Q−TOF−MS analysis suggested the presence of a dimer with m/z 565, 550, 413, 389, 374, 345, 330, and 283 peaks. By comparison, standard isoginkgetin yielded peaks at m/z 565, 533, 518, 489, 401, 389, 374, and 151 in the mass spectra. Based on these experimental data, MS interpretation, and the relevant literature, we concluded that isoginkgetin had higher electron transfer potential than its monomer because of the 3′,8″-dimerization. Additionally, acacetin can produce a dimer during its antioxidant process; however, the dimer is not isoginkgetin. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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11 pages, 864 KiB

Open AccessArticle

Target-Guided Isolation of Three Main Antioxidants from Mahonia bealei (Fort.) Carr. Leaves Using HSCCC

by Weicheng Hu, Jing Zhou, Ting Shen and Xinfeng Wang

Molecules 2019, 24(10), 1907; https://doi.org/10.3390/molecules24101907 - 17 May 2019

Cited by 15 | Viewed by 3134

Abstract

Mahonia bealei (Fort.) Carr. is an economically important plant that is widely cultivated in Southwest China. Its leaves are commonly used for tea and contain an abundance of antioxidant compounds. However, methods of the systematic purification of antioxidants from M. bealei are lacking. [...] Read more.

Mahonia bealei (Fort.) Carr. is an economically important plant that is widely cultivated in Southwest China. Its leaves are commonly used for tea and contain an abundance of antioxidant compounds. However, methods of the systematic purification of antioxidants from M. bealei are lacking. In this study, antioxidants from this plant were effectively and rapidly enriched. First, antioxidants were screened using online 1,1-diphenyl-2-picryl-hydrazyl radical (DPPH)–high performance liquid chromatography (HPLC), followed by separation using high-speed countercurrent chromatography with an optical solvent system composed of n-hexane/ethyl acetate/methanol/water (1:5:1:5, v/v/v/v). Three phenolics—chlorogenic acid (1, 8.3 mg), quercetin-3-O-β-d-glucopyranoside (2, 20.5 mg), and isorhamnetin-3-O-β-d-glucopyranoside (3, 28.4 mg)—were obtained from the ethyl acetate-soluble fraction (240 mg) by one-step separation. The chemical structures of the phenolics were characterized by MS and NMR techniques, and the purity of each compound was >92.0% as determined by HPLC. The isolated compounds were assessed by scavenging activities on DPPH and superoxide radicals as well as cytoprotective assays, all of which showed similar trends regarding the antioxidant capacities of the compounds. Moreover, compounds 1–3 significantly attenuated the lipid peroxidation and antioxidant enzyme activities in H₂O₂-treated RAW264.7 cells. Our study demonstrated the efficiency of a newly developed integrative system for the comprehensive characterization of pure compounds from M. bealei, which will allow their use as reference substances. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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13 pages, 1721 KiB

Open AccessArticle

Comparative Study of Phenolic Profiles, Antioxidant and Antiproliferative Activities in Different Vegetative Parts of Ramie (Boehmeria nivea L.)

by Hong Wang, Caisheng Qiu, Ling Chen, Arshad Mehmood Abbasi, Xinbo Guo and Rui Hai Liu

Molecules 2019, 24(8), 1551; https://doi.org/10.3390/molecules24081551 - 19 Apr 2019

Cited by 26 | Viewed by 5658

Abstract

Ramie (Boehmeria nivea L.) is usually cultivated as a fiber crop, but it is also well known for its potential use in animal feeding with viable commercial applications. In this study, the phenolics profile as well as cellular antioxidant and antiproliferative activities [...] Read more.

Ramie (Boehmeria nivea L.) is usually cultivated as a fiber crop, but it is also well known for its potential use in animal feeding with viable commercial applications. In this study, the phenolics profile as well as cellular antioxidant and antiproliferative activities were investigated in free and bound fractions of six different vegetative parts from Boehmeria nivea L. The highest total phenolic content was observed in bud (4585 ± 320 mg GAE/100 g DW), whereas root and petiole had the lowest total phenolic contents, 442.8 ± 9.8 and 630.9 ± 27.0 mg GAE/100 g DW, respectively. Likewise, phloem had the most abundant total flavonoids (2755 ± 184 mg CE/100 g DW), whereas the lowest flavonoid contents was found in root and petiole, 636.9 ± 44.2 and 797.4 ± 87.6 mg CE/100 g DW, respectively. Xylem and bud depicted remarkable antioxidant and antiproliferative activities, which could be explained by their diverse phenolic composition, especially chlorogenic acid and epicatechin. The Boehmeria nivea L. plant might be a valuable resource for high value-added phenolic compounds used in food and non-food industries. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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38 pages, 7071 KiB

Open AccessArticle

Phytochemical Diversity in Rhizomes of Three Reynoutria Species and their Antioxidant Activity Correlations Elucidated by LC-ESI-MS/MS Analysis

by Izabela Nawrot-Hadzik, Sylwester Ślusarczyk, Sebastian Granica, Jakub Hadzik and Adam Matkowski

Molecules 2019, 24(6), 1136; https://doi.org/10.3390/molecules24061136 - 21 Mar 2019

Cited by 44 | Viewed by 5431

Abstract

The rhizome of Reynoutria japonica is a well-known traditional herb (Hu zhang) used in East Asia to treat various inflammatory diseases, infections, skin diseases, scald, and hyperlipidemia. It is also one of the richest natural sources of resveratrol. Although, it has been recently [...] Read more.

The rhizome of Reynoutria japonica is a well-known traditional herb (Hu zhang) used in East Asia to treat various inflammatory diseases, infections, skin diseases, scald, and hyperlipidemia. It is also one of the richest natural sources of resveratrol. Although, it has been recently included in the European Pharmacopoeia, in Europe it is still an untapped resource. Some of the therapeutic effects are likely to be influenced by its antioxidant properties and this in turn is frequently associated with a high stilbene content. However, compounds other than stilbenes may add to the total antioxidant capacity. Hence, the aim of this research was to examine rhizomes of R. japonica and the less studied but morphologically similar species, R. sachalinensis and R. x bohemica for their phytochemical composition and antioxidant activity and to clarify the relationship between the antioxidant activity and the components by statistical methods. HPLC/UV/ESI-MS studies of three Reynoutria species revealed 171 compounds, comprising stilbenes, carbohydrates, procyanidins, flavan-3-ols, anthraquinones, phenylpropanoids, lignin oligomers, hydroxycinnamic acids, naphthalenes and their derivatives. Our studies confirmed the presence of procyanidins with high degree of polymerization, up to decamers, in the rhizomes of R. japonica and provides new data on the presence of these compounds in other Reynoutria species. A procyanidin trimer digallate was described for the first time in, the studied plants. Moreover, we tentatively identified dianthrone glycosides new for these species and previously unrecorded phenylpropanoid disaccharide esters and hydroxycinnamic acid derivatives. Furthermore, compounds tentatively annotated as lignin oligomers were observed for the first time in the studied species. The rhizomes of all Reynoutria species exhibited strong antioxidant activity. Statistical analysis demonstrated that proanthocyanidins should be considered as important contributors to the total antioxidant capacity. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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14 pages, 1145 KiB

Open AccessArticle

Chromatographic Analysis and Anti-Oxidative Property of Naoxinqing Tablet, a Proprietary Preparation of Diospyros Kaki Leaves

by Magdy Kazzem, Yu-Ting Sun, Mitchell Low, Sai Wang Seto, Dennis Chang, Samiuela Lee, Harsha Suresh, Cheang S. Khoo, Alan Bensoussan and Hosen Kiat

Molecules 2019, 24(6), 1101; https://doi.org/10.3390/molecules24061101 - 20 Mar 2019

Cited by 8 | Viewed by 3461

Abstract

The Naoxinqing (NXQ) tablet is a standardised proprietary herbal product containing an extract of persimmon leaves (Diospyros kaki) for the management of cardio- and cerebrovascular diseases. Although previous reports suggested that the efficacy of NXQ is at least partly mediated by [...] Read more.

The Naoxinqing (NXQ) tablet is a standardised proprietary herbal product containing an extract of persimmon leaves (Diospyros kaki) for the management of cardio- and cerebrovascular diseases. Although previous reports suggested that the efficacy of NXQ is at least partly mediated by its anti-oxidative property, the anti-oxidative effect of the major components of NXQ has not been studied systematically. For quality control purposes, only analytical methods limited to 3 marker analytes have been reported, the extent to which the other components affect efficacy has not been explored. In this study, we developed an ultra-performance liquid chromatography-tandem mass spectrometry (UPLC MS/MS) method for the identification of seven analytes (kaempferol-3-O-glucoside (astragalin), quercetin-3-O-galactoside (hypericin), quercetin-3-O-glucoside (isoquercitin), kaempferol, 3,4-dihydroxybenzoic acid (protocatechuic acid), and furan-2-carboxylic acid (pyromucic acid) and quercetin) in the NXQ. This is the first method reported and validated for the quantification of the seven major secondary metabolites in NXQ. The results for the quantified analytes were then compared in 15 different batches of NXQ. The variation observed in the seven components highlights the need to quantify key bioactive components to ensure product consistency. Radical scavenging activity and abundance was used to rank the analytes. The anti-oxidative effects of NXQ were examined using cultured human vascular endothelial cells (EA.hy926). Corrected 2,2-di(4-tert-octylphenyl)-1-picrylhydrazyl (DPPH) activity results revealed that quercetin and kaempferol have the strongest anti-oxidant capacity in the extract. Both quercetin and kaempferol significantly inhibited the hydrogen peroxide (H₂O₂)-induced EA.hy926 cell injury and intracellular reactive oxygen species (ROS) generation. In conclusion, we established and validated an UPLC-MS/MC method for the analysis of major bioactive components in the NXQ and demonstrated that its anti-oxidative property may play a critical role in cerebrovascular protection. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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20 pages, 1914 KiB

Open AccessArticle

Antioxidant Activities of Vaccinium vitis-idaea L. Leaves within Cultivars and Their Phenolic Compounds

by Lina Raudone, Gabriele Vilkickyte, Lina Pitkauskaite, Raimondas Raudonis, Rimanta Vainoriene and Vida Motiekaityte

Molecules 2019, 24(5), 844; https://doi.org/10.3390/molecules24050844 - 27 Feb 2019

Cited by 53 | Viewed by 6619

Abstract

Lingonberry leaves are the subject of numerous studies because of antioxidant properties, positive influence on the health and potential use in the prevention and treatment of chronic diseases. In this work, the radical scavenging, reducing, chelating activities, and phenolic composition of ten lingonberry [...] Read more.

Lingonberry leaves are the subject of numerous studies because of antioxidant properties, positive influence on the health and potential use in the prevention and treatment of chronic diseases. In this work, the radical scavenging, reducing, chelating activities, and phenolic composition of ten lingonberry leaves cultivars, one subspecies, and one variety were investigated. Furthermore, the antioxidant activity of individual phenolic compounds, that can be found in lingonberry leaves, were analyzed, and structure-activity relationship was determined. Wide diversity for phenolic profile and antioxidant properties of lingonberry leaves has been observed in the present material. Cultivars ‘Kostromskaja rozovaja’, ‘Rubin’, and Vaccinium vitis-idaea var. leucocarpum surpassed all others tested cultivars and lower taxa by contents of phenolic compounds and antioxidant activity. Leaves of lingonberry cultivars and lower taxa are rich in arbutin, flavonol glycosides, proanthocyanidins, and the latter were considered to be the major contributor to antioxidant properties of lingonberry leaves. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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13 pages, 1558 KiB

Open AccessArticle

Fish Protein and Lipid Interactions on the Digestibility and Bioavailability of Starch and Protein from Durum Wheat Pasta

by Ajay S. Desai, Margaret A. Brennan, Xinbo Guo, Xin-An Zeng and Charles S. Brennan

Molecules 2019, 24(5), 839; https://doi.org/10.3390/molecules24050839 - 27 Feb 2019

Cited by 15 | Viewed by 4341

Abstract

This research focussed on the utilisation of salmon protein and lipid to manipulate pasta’s glycaemic index and protein digestibility. Salmon fish (Oncorhynchus tschawytscha) powder (SFP) supplemented pasta flour in amounts from 5% to 20% (w/w). Inclusion of [...] Read more.

This research focussed on the utilisation of salmon protein and lipid to manipulate pasta’s glycaemic index and protein digestibility. Salmon fish (Oncorhynchus tschawytscha) powder (SFP) supplemented pasta flour in amounts from 5% to 20% (w/w). Inclusion of SFP lead to a significant reduction in starch digestibility and hence the potential glycaemic values of pasta (experimental pasta being up to 143% lower than control values). SFP addition to pasta increased the release of phenolic compounds from pasta during both gastric digestion (179%) and pancreatic digestion (133%) in comparison to the control sample. At the same time, the antioxidant activity of the digested pasta was increased by up to 263% (gastric) and 190% (pancreatic) in comparison to durum wheat pasta alone. Interestingly, although protein levels increased with incorporation of SFP, the digestibility values of the protein decreased from 86.41% for the control pasta to 81.95% for 20% SFP pasta. This may indicate that there are interactions between phenols and protein in the pasta samples which affect overall protein digestibility levels. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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17 pages, 1817 KiB

Open AccessArticle

Increased Phenolic Content and Enhanced Antioxidant Activity in Fermented Glutinous Rice Supplemented with Fu Brick Tea

by Xiao Xu, Wenxiu Hu, Siduo Zhou, Chuanhai Tu, Xiudong Xia, Juanmei Zhang and Mingsheng Dong

Molecules 2019, 24(4), 671; https://doi.org/10.3390/molecules24040671 - 14 Feb 2019

Cited by 21 | Viewed by 4598

Abstract

Glutinous rice-based foods have a long history are consumed worldwide. They are also in great demand for the pursuit of novel sensory and natural health benefits. In this study, we developed a novel fermented glutinous rice product with the supplementation of Fu brick [...] Read more.

Glutinous rice-based foods have a long history are consumed worldwide. They are also in great demand for the pursuit of novel sensory and natural health benefits. In this study, we developed a novel fermented glutinous rice product with the supplementation of Fu brick tea. Using in vitro antioxidant evaluation and phenolic compounds analysis, fermentation with Fu brick tea increased the total phenolic content and enhanced the antioxidant activity of glutinous rice, including scavenging of 1,1-Diphenyl-2-picryl-hydrazyl (DPPH) radical, 2,2′-azino-bis-3-ethylbenzthiazoline-6-sulphonic acid (ABTS) radical, and hydroxyl radical, ferric-reducing antioxidant power, and ferric ion reducing power and iron chelating capability. Besides, compared with traditional fermented glutinous rice, this novel functional food exhibited a stronger activity for protecting DNA against hydroxyl radical-induced oxidation damage. Quantitative analysis by HPLC identified 14 compounds covering catechins and phenolic acids, which were considered to be positively related to the enhanced antioxidant capability. Furthermore, we found that 80% ethanol was a suitable extract solvent compared with water, because of its higher extraction efficiency and stronger functional activities. Our results suggested that this novel fermented glutinous rice could serve as a nutraceutical food/ingredient with special sensory and functional activities. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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9 pages, 1058 KiB

Open AccessArticle

HPLC Profile of Longan (cv. Shixia) Pericarp-Sourced Phenolics and Their Antioxidant and Cytotoxic Effects

by Xuelian Bai, Rui Pan, Mingzhu Li, Xiuting Li and Huawei Zhang

Molecules 2019, 24(3), 619; https://doi.org/10.3390/molecules24030619 - 11 Feb 2019

Cited by 33 | Viewed by 5103

Abstract

Longan (Dimocarpus longan Lour.) pericarp, the main by-product of aril and pulp processing, is abundant in phenolic compounds and worthy of further utilization. The present work firstly reported HPLC analysis and in vitro antioxidant evaluation of longan (cv. Shixia) pericarp-derived phenolics (LPPs), [...] Read more.

Longan (Dimocarpus longan Lour.) pericarp, the main by-product of aril and pulp processing, is abundant in phenolic compounds and worthy of further utilization. The present work firstly reported HPLC analysis and in vitro antioxidant evaluation of longan (cv. Shixia) pericarp-derived phenolics (LPPs), the purified longan pericarp extract (LPE), as well as their cytotoxic effect on lung cancer cell line, A549. The results indicated that the purified LPE had significant amounts of phenolics, with content of 57.8 ± 0.6 mg of gallic acid equivalents per gram of dry longan pericarp (mg GAE·g⁻¹ DLP), which consisted of six phenolic compounds (A–F), including protocatechuic acid (A), isoscopoletin (B), quercetin (C), ellagic acid (D), corilagin (E), and proanthocyanidins C1 (F). Antioxidant assays showed that LPPs (10 μM) and LPE (1.0 mg·mL⁻¹) had certain antioxidant activities, in which corilagin (E) possessed the best DPPH radical scavenging rate 71.8 ± 0.5% and •OH inhibition rate 75.9 ± 0.3%, and protocatechuic acid (A) exhibited the strongest Fe²⁺ chelating ability 36.4 ± 0.7%. In vitro cytotoxic tests suggested that LPPs had different effect on A549 cell line, in which corilagin (E) exhibited potent cytotoxicity with an IC₅₀ value of 28.8 ± 1.2 μM. These findings were further confirmed by cell staining experiments. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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12 pages, 2298 KiB

Open AccessArticle

Preparation and Evaluation of Novel Transfersomes Combined with the Natural Antioxidant Resveratrol

by Pey-Shiuan Wu, Yu-Syuan Li, Yi-Ching Kuo, Suh-Jen Jane Tsai and Chih-Chien Lin

Molecules 2019, 24(3), 600; https://doi.org/10.3390/molecules24030600 - 8 Feb 2019

Cited by 85 | Viewed by 6450

Abstract

Resveratrol (tran-3,5,4′-trihydroxystibene, RSV) is a kind of polyphenol which has anti-inflammatory, antioxidant, anti-allergy, and anti-cancer properties, as well as being a scavenger of free radicals and preventing cardiovascular diseases. However, it is quite unstable in light, heat, and other conditions, and [...] Read more.

Resveratrol (tran-3,5,4′-trihydroxystibene, RSV) is a kind of polyphenol which has anti-inflammatory, antioxidant, anti-allergy, and anti-cancer properties, as well as being a scavenger of free radicals and preventing cardiovascular diseases. However, it is quite unstable in light, heat, and other conditions, and decays easily due to environmental factors. For these reasons, this study used a new type of carrier, transfersome, to encapsulate RSV. Transfersome consists of phosphatidyl choline (PC) from a liposomal system and non-ionic edge activators (EA). EA are an important ingredient in the formulation of transfersome; they can enhance the flexibility of the lipid bimolecular membrane of transfersome. Due to its ultradeformability, it also allows drugs to penetrate the skin, even through the stratum corneum. We hope that this new encapsulation technique will improve the stability and enhance the permeability of RSV. Concluding all the tested parameters, the best production condition was 5% PC/EA (3:1) and 5% ethanol in distilled water, with an ultrasonic bath and stirring at 500 rpm, followed by high pressure homogenization. The optimal particle size was 40.13 ± 0.51 nm and the entrapment efficiency (EE) was 59.93 ± 0.99%. The results of antioxidant activity analysis showed that transfersomes were comparable to the RSV group (unencapsulated). During in vitro transdermal delivery analysis, after 6 h, D1-20(W) increased 27.59% by accumulation. Cell viability assay showed that the cytotoxicity of D3-80(W) was reduced by 34.45% compared with the same concentration of RSV. Therefore, we successfully prepared RSV transfersomes and also improved the stability, solubility, and safety of RSV. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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17 pages, 1388 KiB

Open AccessArticle

Flowers of Astragalus membranaceus var. mongholicus as a Novel High Potential By-Product: Phytochemical Characterization and Antioxidant Activity

by Yuan Li, Sheng Guo, Yue Zhu, Hui Yan, Da-wei Qian, Han-qing Wang, Jian-qiang Yu and Jin-ao Duan

Molecules 2019, 24(3), 434; https://doi.org/10.3390/molecules24030434 - 25 Jan 2019

Cited by 32 | Viewed by 4245

Abstract

The root of Astragalus membranaceus var. mongholicus is one of the most popular herbal medicines worldwide. In order to increase the yield of underground roots of A. membranaceus var. mongholicus, its flowers (AMF) have often been removed in their flowering stage, which [...] Read more.

The root of Astragalus membranaceus var. mongholicus is one of the most popular herbal medicines worldwide. In order to increase the yield of underground roots of A. membranaceus var. mongholicus, its flowers (AMF) have often been removed in their flowering stage, which produces the flowers as waste being discarded. To explore its phytochemicals and potential value for utilization, the antioxidant activities of extracts from AMF were evaluated by a free radical scavenging assay and reducing power assay. The total phenols and flavonoids, as well as the individual compounds, in different extracts of AMF were also investigated. The results showed that the extract ME obtained from AMF through macroporous resins separation exhibited strong antioxidant activities, which were close to those of positive control BHT. ME was rich in phenolic acids and flavonoids, and the contents reached 108.42 mg gallic acid equivalents/g and 265.70 mg rutin equivalents/g, respectively. A total of 31 compounds, including four phenolic acids, nineteen flavonoids, three isoflavones, two pterocarpans, and three saponins, were identified using UPLC-QTOF-MS in ME. Quantitative analysis of sixteen components in the extracts of AMF showed that flavonoids were the predominant constituents, especially for the compounds of hyperoside, rutin, and isorhamnetin-3-O-β-d-glucoside. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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14 pages, 6025 KiB

Open AccessArticle

Antioxidant Mechanisms of Echinatin and Licochalcone A

by Minshi Liang, Xican Li, Xiaojian Ouyang, Hong Xie and Dongfeng Chen

Molecules 2019, 24(1), 3; https://doi.org/10.3390/molecules24010003 - 20 Dec 2018

Cited by 42 | Viewed by 5630

Abstract

Echinatin and its 1,1-dimethyl-2-propenyl derivative licochalcone A are two chalcones found in the Chinese herbal medicine Gancao. First, their antioxidant mechanisms were investigated using four sets of colorimetric measurements in this study. Three sets were performed in aqueous solution, namely Cu²⁺ [...] Read more.

Echinatin and its 1,1-dimethyl-2-propenyl derivative licochalcone A are two chalcones found in the Chinese herbal medicine Gancao. First, their antioxidant mechanisms were investigated using four sets of colorimetric measurements in this study. Three sets were performed in aqueous solution, namely Cu²⁺-reduction, Fe³⁺-reduction, and 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide radical (PTIO•)-scavenging measurements, while 1,1-diphenyl-2-picrylhydrazyl radical (DPPH•)-scavenging colorimetric measurements were conducted in methanol solution. The four sets of measurements showed that the radical-scavenging (or metal-reduction) percentages for both echinatin and licochalcone A increased dose-dependently. However, echinatin always gave higher IC₅₀ values than licochalcone A. Further, each product of the reactions of the chalcones with DPPH• was determined using electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC-ESI-Q-TOF-MS/MS). The UPLC-ESI-Q-TOF-MS/MS determination for echinatin yielded several echinatin–DPPH adduct peaks (m/z 662, 226, and 196) and dimeric echinatin peaks (m/z 538, 417, and 297). Similarly, that for licochalcone A yielded licochalcone A-DPPH adduct peaks (m/z 730, 226, and 196) and dimeric licochalcone A peaks (m/z 674 and 553). Finally, the above experimental data were analyzed using mass spectrometry data analysis techniques, resonance theory, and ionization constant calculations. It was concluded that, (i) in aqueous solution, both echinatin and licochalcone A may undergo an electron transfer (ET) and a proton transfer (PT) to cause the antioxidant action. In addition, (ii) in alcoholic solution, hydrogen atom transfer (HAT) antioxidant mechanisms may also occur for both. HAT may preferably occur at the 4-OH, rather than the 4′-OH. Accordingly, the oxygen at the 4-position participates in radical adduct formation (RAF). Lastly, (iii) the 1,1-dimethyl-2-propenyl substituent improves the antioxidant action in both aqueous and alcoholic solutions. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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13 pages, 3379 KiB

Open AccessArticle

Dual Effect of Glucuronidation of a Pyrogallol-Type Phytophenol Antioxidant: A Comparison between Scutellarein and Scutellarin

by Qianru Liu, Xican Li, Xiaojian Ouyang and Dongfeng Chen

Molecules 2018, 23(12), 3225; https://doi.org/10.3390/molecules23123225 - 6 Dec 2018

Cited by 29 | Viewed by 6110

Abstract

To explore whether and how glucuronidation affects pyrogallol-type phytophenols, scutellarein and scutellarin (scutellarein-7-O-glucuronide) were comparatively investigated using a set of antioxidant analyses, including spectrophotometric analysis, UV-vis spectra analysis, and ultra-performance liquid chromatography coupled with electrospray ionization-quadrupole time-of-flight tandem mass spectrometry (UPLC-ESI-Q-TOF-MS/MS) [...] Read more.

To explore whether and how glucuronidation affects pyrogallol-type phytophenols, scutellarein and scutellarin (scutellarein-7-O-glucuronide) were comparatively investigated using a set of antioxidant analyses, including spectrophotometric analysis, UV-vis spectra analysis, and ultra-performance liquid chromatography coupled with electrospray ionization-quadrupole time-of-flight tandem mass spectrometry (UPLC-ESI-Q-TOF-MS/MS) analysis. In spectrophotometric analyses of the scavenging of 1,1-diphenyl-2-picrylhydrazyl (DPPH^•), 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS^+•), and 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide radicals (PTIO^•) and the reduction of Cu²⁺ ions, scutellarein showed lower IC₅₀ values than scutellarin. However, in ^•O₂⁻-scavenging spectrophotometric analysis, scutellarein showed higher IC₅₀ value than scutellarin. The analysis of UV-Vis spectra obtained after the Fe²⁺-chelating reaction of scutellarin showed a typical UV-Vis peak (λ_max = 611 nm), while scutellarein showed no typical peak. In UPLC-ESI-Q-TOF-MS/MS analysis, mixing of scutellarein with DPPH^• yielded MS peaks (m/z 678, 632, 615, 450, 420, 381, 329, 300, 288, 227, 196, 182, 161, and 117) corresponding to the scutellarein-DPPH adduct and an MS peak (m/z 570) corresponding to the scutellarein-scutellarein dimer. Scutellarin, however, generated no MS peak. On the basis of these findings, it can be concluded that glucuronidation of pyrogallol-type phytophenol antioxidants has a dual effect. On the one hand, glucuronidation can decrease the antioxidant potentials (except for ^•O₂⁻ scavenging) and further lower the possibility of radical adduct formation (RAF), while on the other hand, it can enhance the ^•O₂⁻-scavenging and Fe²⁺-chelating potentials. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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12 pages, 2776 KiB

Open AccessArticle

A Null B-Ring Improves the Antioxidant Levels of Flavonol: A Comparative Study between Galangin and 3,5,7-Trihydroxychromone

by Xiaojian Ouyang, Xican Li, Wenbiao Lu, Xiaojun Zhao and Dongfeng Chen

Molecules 2018, 23(12), 3083; https://doi.org/10.3390/molecules23123083 - 26 Nov 2018

Cited by 23 | Viewed by 3299

Abstract

To clarify the role of the B-ring in antioxidant flavonols, we performed a comparative study between galangin with a null B-ring and 3,5,7-trihydroxychromone without a B-ring using five spectrophotometric assays, namely, ^•O₂⁻-scavenging, 1,1-diphenyl-2-picrylhydrazyl radical (DPPH^• [...] Read more.

To clarify the role of the B-ring in antioxidant flavonols, we performed a comparative study between galangin with a null B-ring and 3,5,7-trihydroxychromone without a B-ring using five spectrophotometric assays, namely, ^•O₂⁻-scavenging, 1,1-diphenyl-2-picrylhydrazyl radical (DPPH^•)-scavenging, 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide radical-scavenging, 2,2′-azino-bis(3-ethylbenzo-thiazoline-6-sulfonic acid) radical-scavenging, and Fe³⁺-reducing activity. The DPPH^•-scavenging reaction products of these assays were further analyzed by ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC-ESI-Q-TOF-MS/MS) technology. In the five spectrophotometric assays, galangin and 3,5,7-trihydroxychromone dose-dependently increased their radical-scavenging (or Fe³⁺-reducing) percentages. However, galangin always gave lower IC₅₀ values than those of 3,5,7-trihydroxychromone. In the UPLC-ESI-Q-TOF-MS/MS analysis, galangin yielded galangin-DPPH adduct MS peaks (m/z 662, 434, 301, 227,196, and 151) and galangin-galangin dimer MS peaks (m/z 538, 385, 268, 239, 211, 195, and 151). 3,5,7-Trihydroxychromone, however, only generated m/z 3,5,7-trihydroxychromone-DPPH adduct MS peaks (m/z 586, 539, 227, 196, and 136). In conclusion, both galangin and 3,5,7-trihydroxychromone could similarly undergo multiple antioxidant pathways, including redox-dependent pathways (such as electron transfer (ET) and ET plus proton transfer (PT)) and a non-redox-dependent radical adduct formation (RAF) pathway; thus, the null B-ring could hardly change their antioxidant pathways. However, it did improve their antioxidant levels in these pathways. Such improvement of the B-ring toward an antioxidant flavonol is associated with its π-π conjugation, which can provide more resonance forms and bonding sites. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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17 pages, 2640 KiB

Open AccessArticle

Dragon’s Blood Sap: Storage Stability and Antioxidant Activity

by Juan D. Escobar, Cristina Prieto, Maria Pardo-Figuerez and José M. Lagaron

Molecules 2018, 23(10), 2641; https://doi.org/10.3390/molecules23102641 - 15 Oct 2018

Cited by 17 | Viewed by 6530

Abstract

Currently, consumers are demanding additive-free, fresher, and more-natural products. Dragon’s Blood Sap (DBS), the deep red latex of the specie of tree Croton lechleri (Müll. Arg.), contains a high concentration of phenolic compounds of great interest for the food, pharmaceutical, and cosmetic industries. [...] Read more.

Currently, consumers are demanding additive-free, fresher, and more-natural products. Dragon’s Blood Sap (DBS), the deep red latex of the specie of tree Croton lechleri (Müll. Arg.), contains a high concentration of phenolic compounds of great interest for the food, pharmaceutical, and cosmetic industries. These chemical compounds are highly susceptible to degradation. Therefore, DBS storage stability and its photo-oxidation was studied by Fourier transform infrared spectroscopy (FT-IR) and UV-Vis spectrophotometry for 39 days at different temperatures (4–21 °C) and relative humidities (0–56%), as well as under UV light exposure. It was observed that the degradation of phenolic compounds was reduced at 0% relative humidity (RH), not showing a significant effect of temperature in the range studied. UV light irradiation degraded DBS in a 20%. DBS has an exceptional high and stable antioxidant content (≥93% inhibition percentage of DPPH), which makes it a unique property to consider the DBS as an antioxidant agent or ingredient for consumer products formulations. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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18 pages, 1465 KiB

Open AccessArticle

Polyphenol-Rich Extracts from Cotoneaster Leaves Inhibit Pro-Inflammatory Enzymes and Protect Human Plasma Components against Oxidative Stress In Vitro

by Agnieszka Kicel, Joanna Kolodziejczyk-Czepas, Aleksandra Owczarek, Anna Marchelak, Malgorzata Sopinska, Pawel Ciszewski, Pawel Nowak and Monika A. Olszewska

Molecules 2018, 23(10), 2472; https://doi.org/10.3390/molecules23102472 - 26 Sep 2018

Cited by 14 | Viewed by 4417

Abstract

The present study investigated the phenolic profile and biological activity of dry extracts from leaves of C. bullatus, C. zabelii and C. integerrimus—traditional medicinal and dietary plants—and evaluated their potential in adjunctive therapy of cardiovascular diseases. Complementary UHPLC-PDA-ESI-MS³, HPLC-PDA-fingerprint, [...] Read more.

The present study investigated the phenolic profile and biological activity of dry extracts from leaves of C. bullatus, C. zabelii and C. integerrimus—traditional medicinal and dietary plants—and evaluated their potential in adjunctive therapy of cardiovascular diseases. Complementary UHPLC-PDA-ESI-MS³, HPLC-PDA-fingerprint, Folin-Ciocalteu, and n-butanol/HCl assays of the extracts derived by fractionated extraction confirmed that they are rich in structurally diverse polyphenols (47 analytes, content up to 650.8 mg GAE/g dw) with proanthocyanidins (83.3–358.2 mg CYE/g) dominating in C. bullatus and C. zabelii, and flavonoids (53.4–147.8 mg/g) in C. integerrimus. In chemical in vitro tests of pro-inflammatory enzymes (lipoxygenase, hyaluronidase) inhibition and antioxidant activity (DPPH, FRAP), the extracts effects were dose-, phenolic- and extraction solvent-dependent. The most promising polyphenolic extracts were demonstrated to be effective antioxidants in a biological model of human blood plasma—at in vivo-relevant levels (1–5 µg/mL) they normalized/enhanced the non-enzymatic antioxidant capacity of plasma and effectively prevented peroxynitrite-induced oxidative/nitrative damage of plasma proteins and lipids. As demonstrated in cytotoxicity tests, the extracts were safe—they did not affect viability of human peripheral blood mononuclear cells. In conclusion, Cotoneaster leaves may be useful in development of natural-based products, supporting the treatment of oxidative stress/inflammation-related chronic diseases, including cardiovascular disorders. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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12 pages, 2191 KiB

Open AccessArticle

Geographic Variation in the Chemical Composition and Antioxidant Properties of Phenolic Compounds from Cyclocarya paliurus (Batal) Iljinskaja Leaves

by Yang Liu, Pei Chen, Mingming Zhou, Tongli Wang, Shengzuo Fang, Xulan Shang and Xiangxiang Fu

Molecules 2018, 23(10), 2440; https://doi.org/10.3390/molecules23102440 - 24 Sep 2018

Cited by 57 | Viewed by 4625

Abstract

Cyclocarya paliurus has been widely used as an ingredient in functional foods in China. However, the antioxidant properties of phenolic compounds and the effect of the plant origin remain unclear. The present study evaluated the geographical variation of this plant in term of [...] Read more.

Cyclocarya paliurus has been widely used as an ingredient in functional foods in China. However, the antioxidant properties of phenolic compounds and the effect of the plant origin remain unclear. The present study evaluated the geographical variation of this plant in term of its phenolic composition and antioxidant activities based on leaf materials collected from five regions. high-performance liquid chromatography (HPLC) analysis showed that there are three major components, quercetin-3-O-glucuronide, kaempferol-3-O-glucuronide, and kaempferol-3-O-rhamnoside, and their contents varied significantly among sampling locations. The investigated phenolic compounds showed substantial antioxidant activities, both in vitro and in vivo, with the highest capacity observed from Wufeng and Jinzhongshan. Correlation analysis revealed that quercetin and kaempferol glycosides might be responsible for the antioxidant activities. Our results indicate the importance of geographic origin, with sunny hours and temperature as the main drivers affecting the accumulation of C. paliurus phenolics and their antioxidant properties. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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20 pages, 3706 KiB

Open AccessArticle

The Effects of Cold Saponification on the Unsaponified Fatty Acid Composition and Sensory Perception of Commercial Natural Herbal Soaps

by Natalia Prieto Vidal, Oludoyin Adeseun Adigun, Thu Huong Pham, Abira Mumtaz, Charles Manful, Grace Callahan, Peter Stewart, Dwayne Keough and Raymond Horatio Thomas

Molecules 2018, 23(9), 2356; https://doi.org/10.3390/molecules23092356 - 14 Sep 2018

Cited by 31 | Viewed by 21874

Abstract

Saponification is the process in which triglycerides are combined with a strong base to form fatty acid metal salts during the soap-making process. The distribution of unsaturated and saturated fatty acid determines the hardness, aroma, cleansing, lather, and moisturizing abilities of soaps. Plant [...] Read more.

Saponification is the process in which triglycerides are combined with a strong base to form fatty acid metal salts during the soap-making process. The distribution of unsaturated and saturated fatty acid determines the hardness, aroma, cleansing, lather, and moisturizing abilities of soaps. Plant extracts, such as rosemary, vegetable, and essential oils are frequently added to soaps to enhance quality and sensory appeal. Three natural soaps were formulated using cold saponification to produce a base or control bar (BB), hibiscus rosehip bar (H), and a forest grove bar (FG). Rosemary extract (R) or essential oil (A) blends were added as additives to each formulation prior to curing to evaluate the effects of natural plant additives on the lipid composition and sensory characteristics of these natural herbal soaps. A total of seven natural soaps, three without additives (BB, H, FG) and four with additives (BBR, HA, FGR, FGA), were manufactured and studied. The majority (86–99%) of the polyunsaturated fatty acids (5.0–7.0 µg/mg) remained unsaponified in the manufactured natural soaps regardless of feedstock used. Principal component analysis (PCA) analyses showed the unsaponifiable fatty acids were different in the hibiscus bar compared to the other bars. There was a very strong correlation between the content of unsaponified C18:3n3 and C18:1n9 in all natural soaps. These results indicate that unsaponified fatty acids are important contributors to the quality and overall sensory perception and preference of natural herbal soaps following manufacturing by cold saponification. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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14 pages, 4078 KiB

Open AccessArticle

Walnut Protein Hydrolysates Play a Protective Role on Neurotoxicity Induced by d-Galactose and Aluminum Chloride in Mice

by Li Feng, Xiaojing Wang, Fei Peng, Jianqiao Liao, Yifan Nai, Hongjie Lei, Mei Li and Huaide Xu

Molecules 2018, 23(9), 2308; https://doi.org/10.3390/molecules23092308 - 10 Sep 2018

Cited by 34 | Viewed by 5705

Abstract

In recent years, with an increase in the aging population, neurodegenerative diseases have attracted more and more attention. This study aimed to investigate the potential neuroprotective effect of defatted walnut meal protein hydrolysates (DWMPH) on neurotoxicity induced by d-galactose (d-gal) [...] Read more.

In recent years, with an increase in the aging population, neurodegenerative diseases have attracted more and more attention. This study aimed to investigate the potential neuroprotective effect of defatted walnut meal protein hydrolysates (DWMPH) on neurotoxicity induced by d-galactose (d-gal) and aluminum chloride (AlCl₃) in mice. The animal models were established by combining treatments with d-gal (200 mg/kg/day, subcutaneously) and AlCl₃ (100 mg/kg in drinking water) for 90 days. During the 90 days, 1 g/kg of DWMPH was administrated orally every day. The results indicated that DWMPH treatment alleviated oxidative stress, reversed cholinergic dysfunction, and suppressed the release of proinflammatory cytokines in the brains of d-gal + AlCl₃-treated mice, and thus improving the learning and memory functions of these mice, which was closely correlated with the strong antioxidant activity of DWMPH. This finding suggests that DWMPH might be a promising dietary supplement in improving neuronal dysfunctions of the brain. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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Review

Jump to: Editorial, Research

33 pages, 3674 KiB

Open AccessReview

The Antioxidant Activity of Prenylflavonoids

by Clementina M. M. Santos and Artur M. S. Silva

Molecules 2020, 25(3), 696; https://doi.org/10.3390/molecules25030696 - 6 Feb 2020

Cited by 63 | Viewed by 7171

Abstract

Prenylated flavonoids combine the flavonoid moiety and the lipophilic prenyl side-chain. A great number of derivatives belonging to the class of chalcones, flavones, flavanones, isoflavones and other complex structures possessing different prenylation patterns have been studied in the past two decades for their [...] Read more.

Prenylated flavonoids combine the flavonoid moiety and the lipophilic prenyl side-chain. A great number of derivatives belonging to the class of chalcones, flavones, flavanones, isoflavones and other complex structures possessing different prenylation patterns have been studied in the past two decades for their potential as antioxidant agents. In this review, current knowledge on the natural occurrence and structural characteristics of both natural and synthetic derivatives was compiled. An exhaustive survey on the methods used to evaluate the antioxidant potential of these prenylflavonoids and the main results obtained were also presented and discussed. Whenever possible, structure-activity relationships were explored. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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22 pages, 2365 KiB

Open AccessFeature PaperReview

Management of Fruit Industrial By-Products—A Case Study on Circular Economy Approach

by Débora A. Campos, Ricardo Gómez-García, Ana A. Vilas-Boas, Ana Raquel Madureira and Maria Manuela Pintado

Molecules 2020, 25(2), 320; https://doi.org/10.3390/molecules25020320 - 13 Jan 2020

Cited by 216 | Viewed by 14816

Abstract

The management of industrial fruit by-products is important not only to decrease the volume of food waste accumulated in the landfills but also to develop strategies through reuse with the purpose to valorise and add economic value. The disposal of food waste leads [...] Read more.

The management of industrial fruit by-products is important not only to decrease the volume of food waste accumulated in the landfills but also to develop strategies through reuse with the purpose to valorise and add economic value. The disposal of food waste leads to different global issues in different sectors, such as social, environmental and economical. These by-products represent a rich source of valuable compounds (polyphenols) with high antioxidant activity, which can be extracted through biotechnological methodologies for future industrial applications. In this context, the management of fruit by-products is challenged to move from a linear economy to a circular economy. Therefore, the purpose of this review is to provide a critical view of an integrated valorisation of fruit by-products to overcome a global issue, via the production of antioxidant extracts with high economic value. A case study of pineapple processing industrialization in a circular economy is explored and discussed. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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21 pages, 1618 KiB

Open AccessFeature PaperReview

Quercetin, Epigallocatechin Gallate, Curcumin, and Resveratrol: From Dietary Sources to Human MicroRNA Modulation

by Erika Cione, Chiara La Torre, Roberto Cannataro, Maria Cristina Caroleo, Pierluigi Plastina and Luca Gallelli

Molecules 2020, 25(1), 63; https://doi.org/10.3390/molecules25010063 - 23 Dec 2019

Cited by 148 | Viewed by 22161

Abstract

Epidemiologic studies suggest that dietary polyphenol intake is associated with a lower incidence of several non-communicable diseases. Although several foods contain complex mixtures of polyphenols, numerous factors can affect their content. Besides the well-known capability of these molecules to act as antioxidants, they [...] Read more.

Epidemiologic studies suggest that dietary polyphenol intake is associated with a lower incidence of several non-communicable diseases. Although several foods contain complex mixtures of polyphenols, numerous factors can affect their content. Besides the well-known capability of these molecules to act as antioxidants, they are able to interact with cell-signaling pathways, modulating gene expression, influencing the activity of transcription factors, and modulating microRNAs. Here we deeply describe four polyphenols used as nutritional supplements: quercetin, resveratrol, epigallocatechin gallate (ECGC), and curcumin, summarizing the current knowledge about them, spanning from dietary sources to the epigenetic capabilities of these compounds on microRNA modulation. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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20 pages, 1306 KiB

Open AccessFeature PaperReview

Red Wine Consumption and Cardiovascular Health

by Luigi Castaldo, Alfonso Narváez, Luana Izzo, Giulia Graziani, Anna Gaspari, Giovanni Di Minno and Alberto Ritieni

Molecules 2019, 24(19), 3626; https://doi.org/10.3390/molecules24193626 - 8 Oct 2019

Cited by 164 | Viewed by 31933

Abstract

Wine is a popular alcoholic beverage that has been consumed for hundreds of years. Benefits from moderate alcohol consumption have been widely supported by the scientific literature and, in this line, red wine intake has been related to a lesser risk for coronary [...] Read more.

Wine is a popular alcoholic beverage that has been consumed for hundreds of years. Benefits from moderate alcohol consumption have been widely supported by the scientific literature and, in this line, red wine intake has been related to a lesser risk for coronary heart disease (CHD). Experimental studies and meta-analyses have mainly attributed this outcome to the presence in red wine of a great variety of polyphenolic compounds such as resveratrol, catechin, epicatechin, quercetin, and anthocyanin. Resveratrol is considered the most effective wine compound with respect to the prevention of CHD because of its antioxidant properties. The mechanisms responsible for its putative cardioprotective effects would include changes in lipid profiles, reduction of insulin resistance, and decrease in oxidative stress of low-density lipoprotein cholesterol (LDL-C). The aim of this review is to summarize the accumulated evidence correlating moderate red wine consumption with prevention of CHD by focusing on the different mechanisms underlying this relationship. Furthermore, the chemistry of wine as well as chemical factors that influence the composition of the bioactive components of red wine are also discussed. Full article

(This article belongs to the Special Issue The Antioxidant Capacities of Natural Products 2019)

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