The Photoperoxidation of Unsaturated Organic Molecules—ix. Lipoic Acid Inhibition of Rubrene Autoperoxidation

Stevens, B.; Perez, Steven R.; Small, R. D.

doi:10.1111/j.1751-1097.1974.tb06517.x

Cited by 19 publications

(3 citation statements)

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“…We have been interested in the possible role of singlet oxygen in the photodynamic effect.19 •20 In particular, we have been studying the reactions of singlet oxygen with di-sulfides as models for biological substrates containing the cysteine residue or other disulfide linkage. [21][22][23][24][25] As part of this study we have oxidized dl--lipoic acid under singlet oxygen conditions as well as with other oxidants.…”

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confidence: 99%

Oxidation of .alpha.-lipoic acid

Stary¹,

Jindal²,

Murray³

1975

J. Org. Chem.

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confidence: 99%

Oxidation of .alpha.-lipoic acid

Stary¹,

Jindal²,

Murray³

1975

J. Org. Chem.

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“…Zootec., 45(3): [113][114][115][116][117][118][119][120]2016 as antioxidants in free-radical quenching, metal chelation, antioxidant recycling, and gene expressing (Packer et al, 1995). Likewise, ALA had the scavenging ability directly against the hydroxyl radical, the hypochlorous radical, and singlet oxygen, but not against the superoxide radical and the peroxyl radical (Suzuki et al, 1991;Scott et al, 1994;Kagan et al, 1992;Stevens et al, 1974). However, DHLA, known to rapidly convert into ALA, is capable of quenching the oxidants that cannot be scavenged by ALA (Kagan et al, 1992).…”

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Growth performance, intestinal morphology, and meat quality in relation to alpha-lipoic acid associated with vitamin C and E in broiler chickens under tropical conditions

Yoo

Koo

et al. 2016

R. Bras. Zootec.

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-This study was conducted to examine the effect of alpha-lipoic acid with vitamin C and E on growth performance, intestinal morphology, and meat quality in broiler chickens under tropical conditions. A total of 288 one-day-old male ROSS 308 chicks (40±0.1 g) were used in a completely randomized design and allotted to one of six dietary treatments to form sixe replicates per treatment (eight birds per cage). The six dietary treatments were: a corn-soybean meal-based diet (NC; no antimicrobial compounds added) with 8 ppm alpha-lipoic acid (ALA); 150 ppm vitamin C and 75 ppm vitamin E (E-75); E-75 plus ALA (E-75-ALA); 150 ppm vitamin C and 50 ppm vitamin E (E-50) plus ALA (E-50-ALA); and 150 ppm vitamin C and 25 ppm vitamin E (E-25) plus ALA (E-25-ALA). All dietary treatments were continuously provided in liquid form, dissolved in water. Birds were housed in a battery cage (n = 36), and were offered dietary treatments on an ad libitum basis. The ambient temperature was maintained at 32±1 ºC for the first three weeks and reduced gradually to 28 ºC by the end of the experiment (day 35) to induce moderate tropical condition. One bird per pen (n = 6), and another bird per pen (n = 6) were euthanized via cervical dislocation to obtain terminal ileum to measure villus height and crypt depth at day 21, and to harvest breast meat and drumsticks to evaluate meat quality traits at day 35, respectively. Dietary treatment E-75-ALA improved body weight and average daily gain compared with birds fed other dietary treatments from day 1 to day 35. Birds fed dietary treatment E-75-ALA and E-50-ALA had higher villus height than those fed the other dietary treatments at day 21. Dietary treatments E-75-ALA and E-50-ALA reduced thiobarbituric acid reactive substance (TBARS) in drumsticks compared with other dietary treatments, but only treatment E-75-ALA decreased TBARS in breast meat at day 35. Liquid form of antioxidant compounds such as E-75-ALA can improve growth performance, histology of terminal ileum, and meat quality traits in broiler chickens under moderate tropical condition for 35 days.

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“…There has been much recent interest in ␣-lipoic acid as a powerful antioxidant in animals based primarily on observations that it or its reduced form, dihydrolipoic acid, scavenges hydroxyl radical (1-3), superoxide (2), singlet oxygen (4,5), and hypochlorous acid (1,6,7). In addition, lipoic acid recycles the well known antioxidants ascorbate, glutathione, and vitamin E by reducing their radical form back to the parent compound (8 -11).…”

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Sulfur-centered Radical Formation from the Antioxidant Dihydrolipoic Acid

Mottley¹,

Mason²

2001

Journal of Biological Chemistry

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Lipoic acid and its reduced form, dihydrolipoic acid, are thought to be strong antioxidants. There are also reports of dihydrolipoic acid acting as a pro-oxidant under certain circumstances. This article reports the direct observation by ESR spectrometry of the disulfide radical anion and the spin trapping of the primary thiyl radical formed from the oxidation of dihydrolipoic acid through thiol pumping with phenol and horseradish peroxidase. The disulfide radical anion reacts rapidly with oxygen to form the reactive radical superoxide, which is also trapped. The radical species formed show a potential for pro-oxidant activity of this compound. Although antioxidants, in general, have been shown to have pro-oxidant potential, the pro-oxidant chemistry of dihydrolipoic acid has not been well characterized.There has been much recent interest in ␣-lipoic acid as a powerful antioxidant in animals based primarily on observations that it or its reduced form, dihydrolipoic acid, scavenges hydroxyl radical (1-3), superoxide (2), singlet oxygen (4, 5), and hypochlorous acid (1, 6, 7). In addition, lipoic acid recycles the well known antioxidants ascorbate, glutathione, and vitamin E by reducing their radical form back to the parent compound (8 -11). The antioxidant properties have been reviewed in several papers (12, 13) and so will not be extensively discussed here. Lipoic acid is used to treat toxicities in which free radicalinduced peroxidation of membrane phospholipids is thought to be important (14 -16) and, with vitamin E, has been shown to improve cardiac function after ischemia in rats (17).On the other hand, there are a limited number of reports describing potential pro-oxidant effects of dihydrolipoic acid such as releasing iron from ferritin (18), reducing Fe 3ϩ to Fe 2ϩ in microsomes (19), accelerating deoxyribose degradation by FeCl 3 -EDTA and H 2 O 2 (1), peroxidation of oxidized brain phospholipid liposomes in the presence of Fe 3ϩ (1), accelerating ␣ 1 -antiproteinase inactivation (1), and accelerating the loss of creatine kinase activity in plasma exposed to gas-phase cigarette smoke (1).The oxidation of thiols involves quite complicated chemistry and a number of free radical species (20 -28), each of which has the potential for causing damage in a biological system. It is possible to initiate this oxidation through a process referred to as "thiol pumping" in which a compound, typically a phenol, is metabolized to a reactive free radical by one of a number of peroxidase enzymes, and the radicals so formed are reduced by a thiol, forming a very reactive thiyl radical (29 -36). Thiyl and superoxide radicals produced in this manner from glutathione have been observed by spin trapping (29,31,33,34) while the glutathione disulfide radical anion has been observed directly with ESR (30).Investigators have, until now, been unable to detect sulfurcentered radicals from dihydrolipoic acid in such a system (31, 33) although superoxide production and cycling of the phenoxyl radical back to phenol indicate that the d...

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The Photoperoxidation of Unsaturated Organic Molecules—ix. Lipoic Acid Inhibition of Rubrene Autoperoxidation

Cited by 19 publications

References 4 publications

Oxidation of .alpha.-lipoic acid

Oxidation of .alpha.-lipoic acid

Growth performance, intestinal morphology, and meat quality in relation to alpha-lipoic acid associated with vitamin C and E in broiler chickens under tropical conditions

Sulfur-centered Radical Formation from the Antioxidant Dihydrolipoic Acid

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