Antioxidant Properties of Natural and Synthetic Chromanol Derivatives:  Study by Fast Kinetics and Electron Spin Resonance Spectroscopy

Gregor, Wolfgang; Grabner, Gottfried; Adelwöhrer, Christian; Rosenau, Thomas; Gille, Lars

doi:10.1021/jo047927s

Cited by 66 publications

(56 citation statements)

References 71 publications

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“…Furthermore, compared to trolox (one hydroxyl) and a-tocopherol (one hydroxyl), the bichromanol 3 (2 hydroxyls) exhibited a significantly higher radical scavenging activity (P B 0.001). In agreement with the present result, a novel dimeric antioxidant containing two hydroxyl groups in fused double chromanol rings has been reported to possess better DPPH radical scavenging activity and provide double reducing power compared to a-tocopherol, [24,25]. It is well established that phenolic compounds scavenge radicals by proton donation [6].…”

Section: Dpph Assaysupporting

confidence: 90%

Radical Scavenging Activity and Performance of Novel Phenolic Antioxidants in Oils During Storage and Frying

Catel

Aladedunye

Przybylski

2011

J Americ Oil Chem Soc

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Novel phenolic antioxidants: 2a (6 0 -hydroxy-2 0 , 5 0 ,7 0 ,8 0 -tetramethylchroman-2 0 -yl)methyl 3-methoxy-4-hydroxycinnamate, 2b (6 0 -hydroxy-2 0 ,5 0 ,7 0 ,8 0 -tetramethylchroman-2 0 -yl)methyl 3,5-dimethoxy-4-hydroxycinnamate, 2c (6 0 -hydroxy-2 0 ,5 0 ,7 0 ,8 0 -tetramethylchroman-2 0 -yl)methyl 3,4-dihydroxycinnamate, and 3 (6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methyl (6 0 -hydroxy-2 0 ,5 0 ,7 0 ,8 0 -tetramethylchroman-2 0 -carboxylate) have been prepared in good yields and fully characterized by 1 H and 13 C NMR, and HRMS. Their radical scavenging activities have been evaluated by DPPH and ORAC assays. Each of the synthesized antioxidants exhibited significantly higher radical scavenging activities than trolox and a-tocopherol. These novel antioxidants efficiently protected canola oil triacylglycerides (CTG) during accelerated storage and frying. Compounds 2c and 3 were significantly more efficient than a-tocopherol protecting CTG under accelerated storage. All new antioxidants were more efficient than a-tocopherol under frying conditions and present significantly higher thermal stability.

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Section: Dpph Assaysupporting

confidence: 90%

Radical Scavenging Activity and Performance of Novel Phenolic Antioxidants in Oils During Storage and Frying

Catel

Aladedunye

Przybylski

2011

J Americ Oil Chem Soc

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“…Since its discovery in 1922,132 vitamin E has received considerable attention from chemists, biologists, and clinicians, among others 110. Due to its insolubility in water, several small water soluble analogs such as Trolox C ((±)-6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid) and HPMC (6-hydroxy-2,2-5,7,8-pentamethylchroman) have been developed (Scheme 8; see references 133 and 134). As shown in Table 4, these three phenols show similar thermochemistry in the same solvent.…”

Section: Thermochemistry Of Pcet Reagentsmentioning

confidence: 99%

Thermochemistry of Proton-Coupled Electron Transfer Reagents and its Implications

2010

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“…Vitamin E consists of a head (chroman ring) which carries the active antioxidant group, and a phytyl tail. Chromanol-type compounds act as an antioxidant in biological systems by reduction of oxygen-centered radicals (Gregor et al , 2005, Tyurina et al , 1995). The chroman ring (Figure 1), 2,2,5,7,8-pentamethyl-6-chromanol (PMCol), has shown antiandrogen activity in prostate carcinoma cells and is thus considered a potent chemopreventive agent of androgen dependent cancers such as prostate cancer (Thompson and Wilding, 2003).…”

Section: Introductionmentioning

confidence: 99%

Assessment of oral toxicity and safety of pentamethylchromanol (PMCol), a potential chemopreventative agent, in rats and dogs

Lindeblad¹,

Kapetanović²,

Kabirov³

et al. 2010

Toxicology

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2,2,5,7, was administered by gavage in rats for 28 days at dose levels of 0, 100, 500, and 2000 mg/kg/day. PMCol administration induced decreases in body weight gains and food consumption, hepatotoxicity (increased TBILI, ALB, ALT, TP; increased relative liver weights; increased T4 and TSH), nephrotoxicity (increased BUN and BUN/CREAT, histopathology lesions), effect on lipid metabolism (increased CHOL), anemia, increase in WBC counts (total and differential), coagulation (FBGN↑and PT↓) and hyperkeratosis of the nonglandular stomach in the 2000 mg/kg/day dose group (in one or both sexes). In the 500 mg/kg/ day dose group, toxicity was seen to a lesser extent. In the 100 mg/kg/day dose group, only increased CHOL (females) was observed. To assess the toxicity of PMCol in male dogs it was administered orally by capsule administration for 28 days at dose levels of 0, 50, 200 and 800 mg/ kg/day (4 male dogs/dose group). PMCol treatment at 800 mg/kg/day resulted in pronounced toxicity to the male dogs. Target organs of toxicity were liver and thymus. Treatment at 200 mg/ kg/day resulted in toxicity consistent with slight adverse effect on the liver only. The results of the safety pharmacology study indicate that doses of 0, 50, 200 and 800 mg/kg administered orally did not have an effect on the QT interval, blood pressures and body temperatures following dosing over a 24-hour recording period. Under the conditions of this study, the no-observed-adverse effect level (NOAEL) for daily oral administration of PMCol by gavage for 28 days to male rats was 100 mg/kg/day and 50 mg/kg in male dogs. In female rats, the NOAEL was not established due to statistically significant and biologically meaningful increases in CHOL level seen in the 100 mg/kg/day dose group. The results of these studies indicated that administration of PMCol at higher dose levels resulted in severe toxicity in dogs and moderate toxicity in rats, however, administration at lower levels is considered to be less likely to result in toxicity following 28 days of exposure. Sex-related differences were seen in rats. Male rats appeared to have greater Publisher's Disclaimer: This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final citable form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. NIH Public Access Author ManuscriptToxicology. Author manuscript; available in PMC 2011 June 29. NIH-PA Author ManuscriptNIH-PA Author Manuscript NIH-PA Author Manuscript sensitivity to nephrotoxicity, while female animals had a greater incidence of hepatoxicity and changes in hematological parameters evaluated, especially at a dose of 500 mg/kg/day, which correlated to the higher plasma drug levels in female rats. I...

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Antioxidant Properties of Natural and Synthetic Chromanol Derivatives: Study by Fast Kinetics and Electron Spin Resonance Spectroscopy

Cited by 66 publications

References 71 publications

Radical Scavenging Activity and Performance of Novel Phenolic Antioxidants in Oils During Storage and Frying

Radical Scavenging Activity and Performance of Novel Phenolic Antioxidants in Oils During Storage and Frying

Thermochemistry of Proton-Coupled Electron Transfer Reagents and its Implications

Assessment of oral toxicity and safety of pentamethylchromanol (PMCol), a potential chemopreventative agent, in rats and dogs

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