Electrochemistry of flavonoids

Hodnick, William F.; Milosavljević, Emil B.; Nelson, John H.; Pardini, Ronald S.

doi:10.1016/0006-2952(88)90253-5

Cited by 196 publications

(60 citation statements)

References 21 publications

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“…The redox potentials of flavonoids have also been reported in several studies. 11,13,[15][16][17] Our relative values of oxidation potential of the flavonoids are in agreement with the data in these studies. The high reactivity of flavonoids with O 2 · Ϫ is likely to be dependent on their high susceptibility to rapid oxidation.…”

Section: Resultssupporting

confidence: 91%

“…high electrochemical oxidizability), are good O 2 · Ϫ scavengers. 11,13,[15][16][17] We measured the oxidation of flavonoids by their ability to reduce Cu …”

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confidence: 99%

“…high electrochemical oxidizability), are good O 2 · Ϫ scavengers. 11,13,[15][16][17] We measured the oxidation of flavonoids by their ability to reduce Cu 2ϩ ion, in addition to their electrochemical redox potential. The ability of flavonoids and aromatics which are flavonoidal components to scavenge O 2 · Ϫ radicals was more in accord with their Cu 2ϩ -reducing ability than their redox potential.…”

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confidence: 99%

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The Contribution of the Pyrogallol Moiety to the Superoxide Radical Scavenging Activity of Flavonoids.

Furuno

Akasako

Sugihara

2002

Biological & Pharmaceutical Bulletin

130

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The daily intake of flavonoids, widespread in the plant kingdom, is believed to play a preventive role in the development of certain diseases associated with free radical-induced damage in the body. [1][2][3] The high sensitivity of flavonoids to react with free radicals makes them pharmacological effective. Flavonoids and their ability to inactivate superoxide anion radicals (O 2 · Ϫ ) have been studied for about a decade. [4][5][6][7][8] Flavonoids are most likely to react with O 2 · Ϫ via one electron transfer, in which the former are converted to aroxyl radicals in the B-ring and the latter to hydroxyl peroxide. [9][10][11] It is assumed that the O 2 · Ϫ scavenging activity of flavonoids is associated with their ability to form stable aroxyl radicals.12,13) The combination of the 3Ј,4Ј-dihydroxyl substitution (catechol moiety) in the B-ring with a double bond at C2-3 and C4-carbonyl moiety is considered to be an essential structural requirement for flavonoidal aroxyl radical stabilization. [12][13][14] Thus, the most common flavonoid, quercetin, is generally regarded as having the most favorable structure for effective O 2 · Ϫ scavenging potency. However, there is little systematic work reported on the structure-activity relationships governing the O 2 · Ϫ scavenging activity of flavonoids. There are also inconsistencies regarding the relative O 2 · Ϫ scavenging activity of flavonoids in previous reports. [4][5][6][7][8] We have demonstrated that pyrogallol moiety is an important component of flavonoids, making them efficient O 2 · Ϫ radical scavengers. The high O 2 · Ϫ scavenging activity of flavonoids is likely to reflect their high susceptibility to oxidation. 9-13) Thus, the electrochemical oxidizability of flavonoids has been used as a model for O 2 · Ϫ scavenging ability. There are several reports suggesting that flavonoids with low redox potential, (i.e. high electrochemical oxidizability), are good O 2 · Ϫ scavengers. 11,13,[15][16][17] We measured the oxidation of flavonoids by their ability to reduce Cu MATERIALS AND METHODS MaterialsThe chemical reagents used were obtained from the following companies: flavonoids from Funakoshi Co. (Tokyo, Japan); gallic acid, gallic acid n-propyl ester, pyrogallol, pyrogallol 1-monomethyl ether and catechol from Tokyo Kasei Co. (Tokyo, Japan); NADH, HEPES, nitro blue tetrazolium chloride (NBT), phenazine methosulfate (PMS), dimethyl sulfoxide (DMSO), CuSO 4 · 5H 2 O, cuproine, hydroxylamine hydrochloride, isoamyl alcohol and xanthinoxidase from Wako Pure Chemical Ind. (Osaka, Japan). All chemicals used were of the highest quality available.Superoxide Radical Scavenging Activity (SRSA) For the enzymatic system, 10-25 ml of antioxidant DMSO solution was added to 2.5 ml of 20 mM HEPES buffer at pH 7.2 containing 400 mM xanthin and 100 mM NBT in a 4.5 ml glass cubic cell. To the mixture, 20 ml of 5.0 u/ml xanthinoxidase was added to initiate the generation of O 2 · Ϫ . The mixture was incubated at 25°C for 5 min and read at 560 nm against blank samples which did not...

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Section: Resultssupporting

confidence: 91%

“…high electrochemical oxidizability), are good O 2 · Ϫ scavengers. 11,13,[15][16][17] We measured the oxidation of flavonoids by their ability to reduce Cu …”

mentioning

confidence: 99%

mentioning

confidence: 99%

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The Contribution of the Pyrogallol Moiety to the Superoxide Radical Scavenging Activity of Flavonoids.

Furuno

Akasako

Sugihara

2002

Biological & Pharmaceutical Bulletin

130

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“…For that reason, novel highthroughput methods employ mitochondria as a bio marker for drug safety in pharmaceutical industry drug research (Dykens & Will, 2007). Furthermore, previous studies report the inhibitory effect of flavonoids on mitochondrial respiration (Dorta et al, 2005;Elingold et al, 2008).The respiratory chain inhibition promoted by several flavonoids has been frequently associated with the oxidation potentials of these compounds, which are commonly located in similar range as the mitochondrial redox centers (Firuzi, Lacanna, Petrucci, Marrosu, & Saso, 2005;Hodnick, Mllosavljevic, Nelson, & Pardini, 1988).…”

Section: Discussionmentioning

confidence: 99%

Antioxidant capacity and toxicological evaluation ofPterospartum tridentatumflower extracts

Ferreira

Dinis

Azedo

et al. 2012

CyTA - Journal of Food

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Pterospartum tridentatum Willk. (prickled broom) is an autochthonous plant, common in Portuguese territory. The yellow flowers are used in traditional medicine, as a potential cure for all body illnesses, mainly to treat throat irritations or for diabetes, hypertension and hypercholesterolemia therapy. Despite its traditional use, no toxicological assessment has been performed to our knowledge. A high antioxidant activity of P. tridentatum flower water extract was found, in good agreement with its electrospray ionisation-mass spectroscopy (ESI-MS) spectrum which revealed the presence of several flavonoids, such as luteolin-O-(O-acetyl)-glucuronide, luteolin-Oglucuronide or isorhamnetin-O-hexoside. Mitocondrial respiratory rates (state 4, state 3 and FCCP-stimulated respiration) and respiratory indexes (respiratory control and P/O ratios) showed no consistent decrease of respiratory and phosphorylative efficiencies for the concentrations tested (up to 500 mg.mL 71 ). Cytotoxicity evaluation, using MTT assay, was in agreement with the previous results. In conclusion, for the concentration range commonly used, P. tridentatum flower usage can be regarded as harmless and credible.Keywords: antioxidant capacity; cytotoxicity; oxidative phosphorylation; phytotherapy; Pterospartum tridentatum (L.); Willk.; toxicologic evaluation Pterospartum tridentatum Willk. es una planta auto´ctona comu´n en el territorio portugue´s. Las flores amarillas se usan en medicina tradicional como cura potencial para todas las enfermedades, especialmente para tratamientos de irritacio´n de garganta o para tratamientos contra diabetes, hipertensio´n o hipercolesterolemia. A pesar de su uso tradicional, ninguna evaluacio´n toxicolo´gica se ha llevado a cabo. Se encontro´una alta actividad antioxidante de extracto acuoso de flor de P. Tridentatum, concordando con su espectro ESI-MS, el cual revelo´la presencia de varios flavonoides, como luteolina O-(O-acetil)-glucuro´nido, luteolina-Oglucuro´nido o isorramntina-O-hexo´sido. Las frecuencias respiratorias mitocondriales (estado 4, estado 3 y respiracio´n estimulada por FCCP) mostraron un descenso no consistente de eficiencia respiratoria y fosforilativa para las concentraciones analizadas (hasta 500 mg.mL -1 ). La evaluacio´n de citotoxicidad, usando ensayo MTT, coincidio´con los resultados previos. En conclusio´n, para las concentraciones comu´nmente empleadas, el uso de las flores de P. tridentatum se puede considerar inocuo y verosı´mil.Palabras claves: capacidad antioxidante; citotoxicidad; fosforilacio´n oxidativa; fitoterapia; Pterospartum tridentatum (L.) Willk; evaluacio´n toxicolo´gica Abbreviations: ESI, electrospray ionization; FCCP, carbonyl cyanide p-trifluoromethoxyphenylhydrazone; HepG2, a human hepatoma cell line; MS, mass spectrometry; MTT, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide; P/O ratio, ratio of ADP molecules phosphorylated to atoms of oxygen consumed; RCR, respiratory control ratio (state 3 respiratory rate/state 4 respiratory rate)

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“…2004) phenolic acids and phenolic diterpenes (Pietta et al, 1998) that have different antioxidant (Shahidi et al, 1992) and (Vinson et al, 1997). Studies by Hodnick et al (1988) Showed that flavonoids with hydroxyl groups have been most easily oxidized. The differences in the antioxidant activities depend primarily structural differences of the degree of hydroxylation and methylation of compounds.…”

Section: Journal Of Biology and Life Sciencementioning

confidence: 99%

Dietary Gum Arabic Supplementation Alter Plasma and Tissue Antioxidant and Free Radical Scavenging Activities in Sprague Dawley Male Rats

Kassem

Abdullah

2015

JBLS

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The aim of this study was to determine the antioxidant activities of dietary Gum Arabic supplemented in male rat model. In this study, the Sprague Dawley rats were separated into two groups as follows: the normal control group (NC) and Gum Arabic group (GA). At the end of eight weeks of treatment, the Ferric Reducing Antioxidant Power (FRAP) , 1, 1-Diphenyl-2-picryl-hydrazyl (DPPH) levels, and the total phenol content of the GA extracts, plasma and liver tissue were evaluated. The results showed an increased of plasma and liver antioxidant activates in the GA groups as compared to the NC group. Administration of dietary GA reduced the FRAP and TPC concentration in the plasma and in the liver the GA group. Based on these results, it can be concluded that GA supplemented is the natural antioxidants, especially phenolic compounds, which may act both by reducing the content of toxic compounds in foods and by supplying the human body with exogenous antioxidant.

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Electrochemistry of flavonoids

Cited by 196 publications

References 21 publications

The Contribution of the Pyrogallol Moiety to the Superoxide Radical Scavenging Activity of Flavonoids.

The Contribution of the Pyrogallol Moiety to the Superoxide Radical Scavenging Activity of Flavonoids.

Antioxidant capacity and toxicological evaluation ofPterospartum tridentatumflower extracts

Dietary Gum Arabic Supplementation Alter Plasma and Tissue Antioxidant and Free Radical Scavenging Activities in Sprague Dawley Male Rats

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