The structure-antioxidant activity relationship of dehydrodiferulates

Jia, Yuan; He, Ying; Lu, Fachuang

doi:10.1016/j.foodchem.2018.07.038

Cited by 47 publications

(42 citation statements)

References 30 publications

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“…These accurate and reliable analyses clearly demonstrate the butein dimer as one of antioxidant products of butein. The dimer formation supports the HAT mechanism for the antioxidant process, similar to reports from the literature [55,71,72]. Similar to butein, (S)-butin was also observed to yield a dimer by UPLC-ESI-Q-TOF-MS analysis ( Figure 2).…”

Section: Resultssupporting

confidence: 87%

Simultaneous Study of Anti-Ferroptosis and Antioxidant Mechanisms of Butein and (S)-Butin

Liu

Cai

et al. 2020

Molecules

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To elucidate the mechanism of anti-ferroptosis and examine structural optimization in natural phenolics, cellular and chemical assays were performed with 2′-hydroxy chalcone butein and dihydroflavone (S)-butin. C11-BODIPY staining and flow cytometric assays suggest that butein more effectively inhibits ferroptosis in erastin-treated bone marrow-derived mesenchymal stem cells than (S)-butin. Butein also exhibited higher antioxidant percentages than (S)-butin in five antioxidant assays: linoleic acid emulsion assay, Fe3+-reducing antioxidant power assay, Cu2+-reducing antioxidant power assay, 2-phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide radical (PTIO•)-trapping assay, and α,α-diphenyl-β-picrylhydrazyl radical (DPPH•)-trapping assay. Their reaction products with DPPH• were further analyzed using ultra-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UPLC-ESI-Q-TOF-MS). Butein and (S)-butin produced a butein 5,5-dimer (m/z 542, 271, 253, 225, 135, and 91) and a (S)-butin 5′,5′-dimer (m/z 542, 389, 269, 253, and 151), respectively. Interestingly, butein forms a cross dimer with (S)-butin (m/z 542, 523, 433, 419, 415, 406, and 375). Therefore, we conclude that butein and (S)-butin exert anti-ferroptotic action via an antioxidant pathway (especially the hydrogen atom transfer pathway). Following this pathway, butein and (S)-butin yield both self-dimers and cross dimers. Butein displays superior antioxidant or anti-ferroptosis action to (S)-butin. This can be attributed the decrease in π-π conjugation in butein due to saturation of its α,β-double bond and loss of its 2′-hydroxy group upon biocatalytical isomerization.

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Section: Resultssupporting

confidence: 87%

Simultaneous Study of Anti-Ferroptosis and Antioxidant Mechanisms of Butein and (S)-Butin

Liu

Cai

et al. 2020

Molecules

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“…It has been previously reported that ABTS is an unstable radical cation that reacts with antioxidants to generate compounds with antioxidant activity, thus leading to the overestimation of the antioxidant activity in a sample. In contrast, the relatively stable radical DPPH can be easily reduced by extracting hydrogen from hydrogen donors [35]. The results show that the partial deferuloylation of AXs reduced their antioxidant activity by 36% and 42% using the DPPH and ABTS methods, respectively.…”

Section: Ax and Fax Gelling And Antioxidant Propertiesmentioning

confidence: 92%

Feruloylated Arabinoxylans from Maize Distiller’s Dried Grains with Solubles: Effect of Feruloyl Esterase on their Macromolecular Characteristics, Gelling, and Antioxidant Properties

Márquez-Escalante

Carvajal-Millán

2019

Sustainability

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Distiller’s dried grains with solubles (DDGS) are co-products of the maize ethanol industry. DDGS contains feruloylated arabinoxylans (AXs), which can present gelling, antioxidant, and health-promoting effects. However, AXs presenting high ferulic acid (FA) content can exhibit delayed fermentation by the colonic microbiota. Therefore, partial deferuloylation of AXs from DDGS while preserving the polysaccharide gelling and antioxidant properties could add value and favor the sustainable development of bioethanol plants. The aim of this work was to partially deferuloylated AXs from DDGS using feruloyl esterase and to evaluate the polysaccharide macromolecular characteristics, gelling, and antioxidant properties. The AXs presented FA and FA dimer contents of 3.27 and 0.30 µg/mg polysaccharide, respectively, which decreased to 1.26 and 0.20 µg/mg polysaccharide, respectively, in feruloyl esterase-treated AXs (FAXs). The molecular weight and intrinsic viscosity of FAXs were slightly less than those of AXs. The Fourier transform infrared spectroscopy data of AXs and FAXs were similar, confirming that the enzyme did not modify the polysaccharide molecular identity. FAX gels (2% w/v) exhibited a decrease in elasticity by 43% in relation to that of AXs gels. The antioxidant capacity of FAXs was reduced by 32% and 43% (DPPH and ABTS method, respectively), compared with that of AXs. The FAX gelling and antioxidant properties were -comparable to those reported for other AXs in the literature. Feruloyl esterase may offer an interesting approach for the design of functional FAXs as value-added products recovered from DDGS.

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“…The presence of a carboxy group in the molecule of para ‐coumaric acid and its analogs allows to synthesize various derivatives, e. g., esters and amides. It is known that para ‐coumaric acids, their N‐ and/or O ‐containing derivatives, as well as hybrid molecules based on them, have a wide range of activities and exhibit antioxidant (AO), antimicrobial, antifungal, antitumor, and other properties . Thus, artepillin C and some of its derivatives are inhibitors of oxidative processes on in vitro models, and the activity and bioaccessibility of individual compounds based on them are caused, inter alia, by the presence of lipophilic terpenic fragments …”

Section: Introductionmentioning

confidence: 99%

“…It is known that para-coumaric acids, their N-and/or O-Supporting information for this article is available on the WWW under https://doi.org/10.1002/cbdv.201900362 containing derivatives, as well as hybrid molecules based on them, have a wide range of activities and exhibit antioxidant (AO), antimicrobial, antifungal, antitumor, and other properties 1 . [1,[10][11][12][13][14][15][16] Thus, artepillin C and some of its derivatives are inhibitors of oxidative processes on in vitro models, [7 -9] and the activity and bioaccessibility of individual compounds based on them are caused, inter alia, by the presence of lipophilic terpenic fragments. [7] para-Coumaric acids are often present in natural sources only in small amounts, so synthesis of such acids and/or their analogs not found in nature, as well as their derivatives, is a justified way to obtain products of this class of compounds.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antioxidant Ability of Novel Derivatives Based on para‐Coumaric Acid Containing Isobornyl Groups

Буравлев

Dvornikova

Schevchenko

et al. 2019

Chemistry & Biodiversity

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A series of novel esters and amides was synthesized on the basis of para‐coumaric acid containing isobornyl groups in ortho‐positions relative to the phenolic hydroxy group. Antioxidant properties of the obtained compounds were evaluated and compared on in vitro models: radical‐scavenging ability, antioxidant activity on a substrate containing the lipids of animal brain, cytotoxicity of red blood cells, antioxidant and membrane‐protective properties on the model of oxidative red blood cells hemolysis. Statistically significant relationship was established between the antioxidant activity of the studied compounds in model system containing animal lipids and the parameters reflecting their antioxidant properties on the model of H2O2‐induced hemolysis of red blood cells. It was determined that an amide with a morpholine fragment has the highest antioxidant activity. The specified derivative significantly surpassed the reference substances (parent acid, BHT) and was not inferior to the effective antioxidant 2,6‐diisobornyl‐4‐methylphenol in terms of its properties.

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The structure-antioxidant activity relationship of dehydrodiferulates

Cited by 47 publications

References 30 publications

Simultaneous Study of Anti-Ferroptosis and Antioxidant Mechanisms of Butein and (S)-Butin

Simultaneous Study of Anti-Ferroptosis and Antioxidant Mechanisms of Butein and (S)-Butin

Feruloylated Arabinoxylans from Maize Distiller’s Dried Grains with Solubles: Effect of Feruloyl Esterase on their Macromolecular Characteristics, Gelling, and Antioxidant Properties

Synthesis and Antioxidant Ability of Novel Derivatives Based on para‐Coumaric Acid Containing Isobornyl Groups

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