5,7,3′,4′-Hydroxy substituted flavonoids reduce the heme of cytochrome c with a range of rate constants

Smith, Montserrat Rabago; Kindl, Evan D.; Williams, Imani R.; Moorman, Veronica R.

doi:10.1016/j.biochi.2019.04.022

Cited by 8 publications

(2 citation statements)

References 50 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The involvement of the PT pathway can be attributed to a fact that phenolics always exhibit weak acidity. In fact, (S)-butin had a pKa value of 7.11 at 3 -OH [50,51]. On the other hand, the PTIO • scavenging reaction in pH 4.5 aqueous solution is indicated as an ET process [49].…”

Section: Resultsmentioning

confidence: 99%

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

Liu

Cai

et al. 2020

Molecules

View full text Add to dashboard Cite

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.

show abstract

Section: Resultsmentioning

confidence: 99%

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

Liu

Cai

et al. 2020

Molecules

View full text Add to dashboard Cite

show abstract

“…Tetrahydroxyflavanones have been shown to reduce the heme group in cytochrome c, which is a necessary component of the electron transport system and is also involved in apoptotic pathways. The oxidation state of the iron in the heme group is crucial to its specific functions [30]. These compounds can be seen as the addition of a phenol group to naringenin, with two being observed in these data: 3 ,4 ,5,7-tetrahydroxyisoflavanone ([2M-H] − , m/z 575.1184, 1.20 min) and eriodictyol ([M-H] − , m/z 287.0554, 2.19 min).…”

Section: Tentative Identification Of Polyphenolsmentioning

confidence: 99%

Polyphenolic Profiling of Green Waste Determined by UPLC-HDMSE

Potter

Jones

2021

Processes

View full text Add to dashboard Cite

Valorising green waste will greatly enhance and promote the sustainable management of this large volume resource. One potential way to achieve this is the extraction of high value human health promoting chemicals (e.g., polyphenols) from this material. Our primary aim was to identify the main polyphenols present in four contrasting green waste feedstocks, namely Smyrnium olusatrum, Urtica dioica, Allium ursinum and Ulex europaeus, using UPLC-HDMSE. Polyphenol-rich Camellia sinensis (green tea) was used as a reference material. Samples were extracted and analysed by UPLC-HDMSE, which was followed by data processing using Progenesis QI and EZ Info. A total of 77 high scoring polyphenolic compounds with reported benefits to human health were tentatively identified in the samples, with abundances varying across the plant types; A. ursinum was seen to be the least abundant in respect to the polyphenols identified, whereas U. europaeus was the most abundant. Important components with a diverse range of bioactivity, such as procyanidins, (−)-epigallocatechin, naringenin, eriodictyol and iso-liquiritigenin, were observed, plus a number of phytoestrogens such as daidzein, glycitin and genistein. This research provides a route to valorise green waste through the creation of nutritional supplements which may aid in the prevention of disease.

show abstract

Polyphenols bind to low density lipoprotein at biologically relevant concentrations that are protective for heart disease

Tung¹,

Rizzo²,

Dabbagh³

et al. 2020

Archives of Biochemistry and Biophysics

View full text Add to dashboard Cite

5,7,3′,4′-Hydroxy substituted flavonoids reduce the heme of cytochrome c with a range of rate constants

Cited by 8 publications

References 50 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

Polyphenolic Profiling of Green Waste Determined by UPLC-HDMSE

Polyphenols bind to low density lipoprotein at biologically relevant concentrations that are protective for heart disease

Contact Info

Product

Resources

About