The reaction of an autoxidized lipid with proteins

Andrews, Fred A.; Bjorksten, Johan; Trenk, F.B.; Henick, A. S.; Koch, Rainer

doi:10.1007/bf02631862

Cited by 56 publications

(19 citation statements)

References 7 publications

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“…Only a few research studies on model systems have investigated changes in protein after oxidation of proteinlipid systems (Narayan et al, 1958(Narayan et al, , 1963(Narayan et al, , 1964Nishida et al, 1960;Desai et al, 1963 ;Andrews et al, 1965 ;Roubal et al, 1966a,b). With the exception of the study of Andrews et al (1965)) the model systems in these studies had high moisture conten&.…”

Section: Oxidationmentioning

confidence: 96%

Oxidation Effects in a Freeze‐Dried Gelatin‐Methyl Linoleate System

Zirlin

Karel

1969

Journal of Food Science

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SUMMARY– We studied oxidation of a freeze‐dried model system consisting of methyl linoleate and gelatin by incubating the model system in air at 50°C for up to 10 days in the dry state or at controlled relative humidities. Incubation for 5‐10 days caused a drop in the viscosity of gelatin solutions, an increase in the solubility of gelatin in ethanol‐rich solvent mixtures, an increase in the retention time of gelatin on a Sephadex G‐150 column, and a reduction in the melting point of a standard gelatin gel. There were no such changes in the viscosity and solubility properties of gelatin when incubation was at a relative humidity of approximately 60%. In some instances, incubation at high relative humidity led to partial insolubilization of gelatin in water or in acetate buffer. The oxidation effects in the dry state were consistent with the hypothesis that gelatin undergoes oxidative degradation. The effects of oxidation showed similarities to effects of ionizing radiations.

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Section: Oxidationmentioning

confidence: 96%

Oxidation Effects in a Freeze‐Dried Gelatin‐Methyl Linoleate System

Zirlin

Karel

1969

Journal of Food Science

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“…Because of the bifunctionality of this aldehyde, cross-linking between free amino groups of proteins is possible. Andrews et al (1965) demonstrated that mixtures of gelatin and peroxidized methyl linoleate led to cross-linked gelatin. Bisulfite, which forms adducts with aldehydes, prevented the cross-links.…”

Section: Oxidized Lipid/protein Reactionsmentioning

confidence: 99%

The role of lipids in nonenzymatic browning

Hidalgo¹,

Zamora²

2000

Grasas y Aceites

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RESUMEN El papel de los lípidos en el pardeamiento no enzimáticoEn este trabajo se hace una revisión del papel de los lípidos en el pardeamiento no enzimático de alimentos mediante el estudio de las reacciones proteína/lípido oxidado en comparación con otras reacciones donde ocurre también este oscurecimiento: la reacción de Maillard, el pardeamiento producido por el ácido ascórbico, y las reacciones de las quinonas con los grupos amino. Los mecanismos propuestos para estas reacciones de producción de color y fluorescencia, así como la formación de melanoidinas, lipofuscinas y productos coloreados de bajo peso molecular son discutidos de forma comparada, concluyendo que el papel de los lípidos en estas reacciones no parece ser muy diferente del papel de los carbohidratos en el Maillard o de los fenoles en el pardeamiento enzimático. Estas reacciones carbonil-amino parecen ser un grupo de reacciones secundarias que ocurren de forma gradual, son parcialmente reversibles, son universales e inevitables y ocurren en alimentos y en sistemas biológicos. Sin embargo, la mayoría de estos resultados han sido obtenidos en sistemas modelo y estudios adicionales deberían ser abordados en sistemas más cercanos a los alimentos y a lo seres vivos, lo que debería repercutir en un mejor entendimiento del pardeamiento no enzimático y, en definitiva, nos daría una visión más completa de la bioquímica de los alimentos y de los seres vivos. PALABRAS-CLAVE: Interacciones proteína-lípido oxidado Pardeamiento no enzimático Reacción de MaillardReacciones amino-carbonilo. SUMMARY The role of lipids in nonenzymatic browningThe role of lipids in nonenzymatic browning is studied by reviewing oxidized lipid/protein reactions in comparison with other reactions where the production of browning is known: the Maillard reaction, the ascorbic acid browning, and the quinone/amine reactions. The mechanisms proposed in these reactions for production of color and fluorescence, as well as the formation of melanoidins, lipofuscins, and low molecular weight colored products are discussed comparatively, concluding that the role of lipids in these reactions does not seem to be very different to the role of carbohydrates in the Maillard reaction or the phenols in the enzymatic browning. These carbonyl-amine reactions seem to be a group of gradual, partially reversible, universal, and inevitable side reactions in both food and biological systems. However, most of these results were obtained in model systems and additional studies should be carried out in systems closer to real foods or living beings, which should provide a more complete understanding of nonenzymatic browning, and, therefore, to afford a much more comprehensive knowledge of food and human biochemistry. KEY-WORDS: Amino-carbonyl reactions Maillard reactionNonenzymatic browning Oxidized lipid-protein interactions.

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“…One would expect the molecule to autoxidize in the presence of air (either under anhydrous or solvated conditions) with the formation of free radicals, hydroperoxides, peroxides, oxiranes, and carbonyl compounds, as is typical of unsaturated lipids (19). Formation of these highly reactive intermediates would not only reduce the effective drug concentration in solution but would also quite likely contribute to its toxicity, as has been shown for a number of unsaturated lipids (2,8,9,12,15,18).…”

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confidence: 97%

Influence of Antioxidants on the Bioactivity of Amphotericin B

Andrews

Beggs

Sarosi

1977

Antimicrob Agents Chemother

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Four antioxidants, propyl gallate, butylated hydroxyanisole, butylated hydroxytoluene, and D-a-tocopherol acid succinate were found to stabilize amphotericin B and to prolong its antifungal activity against Candida albicans. Although each of the antioxidants was effective in this respect, propyl gallate and butylated hydroxyanisole were better than butylated hydroxytoluene and a-tocopherol acid succinate. None of the antioxidants alone adversely affected normal cell growth. It is suggested that amphotericin B instability is due, at least in part, to lability of the carbon-carbon double bonds of the polyene moiety toward autoxidation. By protecting the drug molecule with an antioxidant, it is possible to significantly lower the quantity of AB necessary to obtain particular antifungal effects.

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The reaction of an autoxidized lipid with proteins

Cited by 56 publications

References 7 publications

Oxidation Effects in a Freeze‐Dried Gelatin‐Methyl Linoleate System

Oxidation Effects in a Freeze‐Dried Gelatin‐Methyl Linoleate System

The role of lipids in nonenzymatic browning

Influence of Antioxidants on the Bioactivity of Amphotericin B

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