A new vitamin E analogue more active than α‐tocopherol in the rat curative myopathy bioassay

Ingold, K. U.; Burton, Graham W.; Foster, David O.; Zuker, Michael; Hughes, L.; Lacelle, Suzanne; Lusztyk, E.; Slabý, Martin

doi:10.1016/0014-5793(86)80877-8

Cited by 46 publications

(35 citation statements)

References 9 publications

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“…The hydroxyl group in C-6 of the chromanol ring is very important for the radical-scavenging activity, as known from other phenols [11]. The phenolic hydrogen is donated to lipophilic free radicals [45,46]. Hence, by esterification the antioxidant activity gets almost lost [47].…”

Section: Antioxidant Activity Of Tocopherols and Tocotrienolsmentioning

confidence: 98%

In vitro antioxidant activity of tocopherols and tocotrienols and comparison of vitamin E concentration and lipophilic antioxidant capacity in human plasma

Müller

Theile

Böhm

2010

Molecular Nutrition Food Res

173

112

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A comparative study investigated four tocopherols, four tocotrienols, and alpha-tocopheryl acetate on their antioxidative activities in five different popular assays, which were adapted to non-polar antioxidants. alpha-Tocopherol, used as calibration standard, showed the highest ferric reducing antioxidant power. Greater ring methyl substitution not only led to an increase of scavenging activity against the stable 2,2-diphenyl-1-picrylhydrazyl radical, but also to a decrease in oxygen radical absorbance capacity. Regarding alpha-tocopherol equivalent antioxidant capacity no significant differences in the antioxidant activity of all vitamin E isoforms were found. In contrast, a significantly lower peroxyl radical-scavenging activity of alpha-tocochromanols was determined in a chemiluminescence assay. Except oxygen radical absorbance capacity, no significant differences of the antioxidant activity related to the side chain could be detected. The data show that the reducing ability and radical chain-breaking activity of the several vitamin E forms depends on the circumstances under which the assays are performed. In our opinion, the used lipophilic methods can be useful for estimating the antioxidant activity of strong non-polar antioxidants, e.g. carotenoids, too. Furthermore, we could show a significant correlation between the total tocopherol content in human plasma and the lipophilic antioxidant capacity measured by alpha-tocopherol equivalent antioxidant capacity and 2,2-diphenyl-1-picrylhydrazyl.

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Section: Antioxidant Activity Of Tocopherols and Tocotrienolsmentioning

confidence: 98%

In vitro antioxidant activity of tocopherols and tocotrienols and comparison of vitamin E concentration and lipophilic antioxidant capacity in human plasma

Müller

Theile

Böhm

2010

Molecular Nutrition Food Res

173

112

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“…We wanted a unique combination of characteristics: (i) high reactivity against lipoprotein oxidation and (ii) localization inside the hydrophobic core of the LDL particle. The high reactivity is rationally designed by lowering the dissociation energy of the phenolic OOH bond, that is, the oxygen atom located para to the phenolic hydroxyl group can stabilize the phenoxyl radical potently when it belongs to a 5-membered ring, as described by Ingold et al (17). Thus, we designed a hydroxybenzofuran structure to achieve the former characteristics.…”

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confidence: 99%

Antiatherogenic effects of the antioxidant BO-653 in three different animal models

Cynshi

Kawabe

Suzuki

et al. 1998

Proc. Natl. Acad. Sci. U.S.A.

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Antioxidants have been proposed to have antiatherogenic potential by their inhibition of low density lipoprotein (LDL) oxidation. Here, we report an antioxidant, BO-653 (2,3-dihydro-5-hydroxy-2,2-dipentyl-4,6-di-tert-butylbenzofuran), designed to exhibit antioxidative potency comparable to that of ␣-tocopherol, but yet possess a high degree of lipophilicity comparable to that of probucol. BO-653 exhibits a high affinity for LDL and is well distributed in aortic vessels in vivo. In atherosclerosis models of rabbits and mice, BO-653 has been shown to be able to suppress the formation of atherosclerotic lesions without untoward side effects. Specifically, there was no reduction of high density lipoprotein levels. This antioxidant provides additional evidence in support of the oxidized-LDL hypothesis, and itself is a promising candidate antioxidant for clinical use.

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“…In recent years a number of pharmacological antioxidant strategies have been developed aimed at blocking ROS production and lipid peroxidation (15,16). In order to develop novel antioxidants better than vitamin E, several attempts to synthesize vitamin E analogues have been reported (40)(41)(42)(43)(44)(45). Recently, we reported a new synthetic analogue of α-tocopherol (compound 1) which was more effective than α-tocopherol as scavenger of reactive oxygen species in glutathione-depleted leukemia CEM cells and prevented lipid peroxidation in mitochondrial membranes (24).…”

Section: Discussionmentioning

confidence: 97%

An Acetate Prodrug of a Pyridinol-Based Vitamin E Analogue

Khdour

Hecht

2011

Pharm Res

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A new vitamin E analogue more active than α‐tocopherol in the rat curative myopathy bioassay

Cited by 46 publications

References 9 publications

In vitro antioxidant activity of tocopherols and tocotrienols and comparison of vitamin E concentration and lipophilic antioxidant capacity in human plasma

In vitro antioxidant activity of tocopherols and tocotrienols and comparison of vitamin E concentration and lipophilic antioxidant capacity in human plasma

Antiatherogenic effects of the antioxidant BO-653 in three different animal models

An Acetate Prodrug of a Pyridinol-Based Vitamin E Analogue

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