Natural antioxidants produced in oxidized lipid/amino acid browning reactions

Alaiz, Manuel; Zamora, Rosario; Hidalgo, Francisco J.

doi:10.1007/bf02577856

Cited by 23 publications

(17 citation statements)

References 24 publications

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“…Thus, when PE was tested by employing the Rancimat method, carbonyl/amine compounds were produced in situ, and these compounds, which previous studies have shown to have antioxidative properties (10,(42)(43)(44)(45), protected the oil. These results were analogous to those obtained when antioxidative activity of slightly oxidized PE samples was tested by the Schaal oven test (9).…”

Section: Discussionmentioning

confidence: 99%

Antioxidative Activity of Amino Phospholipids and Phospholipid/Amino Acid Mixtures in Edible Oils As Determined by the Rancimat Method

Hidalgo

León

Zamora

2006

J. Agric. Food Chem.

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Phosphatidylethanolamine (PE), phosphatidylcholine (PC), lysine (Lys), and mixtures of them were tested for antioxidative activity in refined olive oil by the Rancimat method to investigate the role of the chemical reactions produced in the Rancimat vessel on the induction periods (IPs) obtained. PE and Lys, but not PC, increased the IPs of the oil when tested alone. In addition, PE/Lys and PC/Lys mixtures, but not PC/PE mixtures, exhibited a synergistic effect. All these results can be understood considering the in situ formation of oxidized lipid/amino compound reaction products with antioxidative activities. Thus, the formation of pyrroles could be detected after derivatization with p-(dimethylamino)benzaldehyde, and some of these compounds could be unambiguously identified by GC-MS after their conversion into volatile derivatives. In addition, the formed products contributed to the color developed, and a correlation was observed between the Rancimat IPs obtained and the yellowness index of the oxidized oils recovered from the Rancimat. Furthermore, the differences observed in the antioxidative activities of PE, PC, Lys, and their mixtures could be explained according to the lipophility and hydrophility of the oxidized lipid/amino compound reaction products formed. All these results suggest that chemical reactions are being produced in the Rancimat vessel and the Rancimat IPs obtained are a consequence of the antioxidative activities of the products formed in these reactions. Furthermore, Rancimat may be a valuable tool for testing antioxidative activities of antioxidants produced during food processing if favorable conditions for antioxidant formation are employed.

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Section: Discussionmentioning

confidence: 99%

Antioxidative Activity of Amino Phospholipids and Phospholipid/Amino Acid Mixtures in Edible Oils As Determined by the Rancimat Method

Hidalgo

León

Zamora

2006

J. Agric. Food Chem.

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“…Oil analysis. Oil stabilities were determined by the Rancimat method as described previously (12). Briefly, oil samples (2.5 g) were heated at 110ºC in a Metrohm Rancimat apparatus (Metrohm AG, Herisau, Switzerland).…”

Section: Methodsmentioning

confidence: 99%

Low molecular weight polypeptides in virgin and refined olive oils

Hidalgo

Alaiz

Zamora

2002

J Americ Oil Chem Soc

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Twenty-eight virgin olive oils-from different regions of Spain and prepared from olive drupes of different varieties-and six refined olive oils were analyzed to determine the presence of proteins in these oils. All oils studied showed the presence of proteins in the range of 7-51 µg/100 g of oil. There were no significant differences in protein content in oils from different varieties or between virgin or refined oils. In addition, all oils exhibited analogous amino acid patterns, suggesting a similarity among protein fractions obtained from different oils. A polypeptide with an apparent M.W. of 4600 Da was common to the isolated protein fractions. These results suggest that this polypeptide is a previously unknown minor component in olive oils. No clear influence of this component on oil stability was observed when oil stabilities were estimated as a function of phenol, tocopherol, phosphorus, and protein contents of the oils.Paper no. J10072 in JAOCS 79, 685-689 (July 2002). KEY WORDS:Amino acid analysis, minor components, oil stability, phenols, proteins, refined olive oil, tocopherols, virgin olive oil.Olive oil is composed primarily by TAG and secondarily (less than 5%) by FFA and some other glyceridic and nonglyceridic constituents (1-3). These minor constituents are important for the stability and flavor of olive oil, and their quantitative analysis is a major determinant defining olive oil genuineness (detection of adulterations with seed oils or solvent-extracted oils) and quality grade (extra virgin, virgin, "lampante," "refined," "pure," etc.) (4,5). The various classes of minor constituents can be divided into two groups. The first group consists of FA derivatives such as MAG and DAG, phosphatides, waxes, and esters of sterols. The second group includes classes of compounds not related chemically to FA, such as hydrocarbons, aliphatic alcohols, free sterols, tocopherols, chlorophylls, carotenoids, and polar phenolic compounds. All these different classes of compounds are present in a broad range of concentrations, and some of them may be reduced or eliminated during refining (1-3).The presence of different enzymes in virgin olive oils has been described as an impurity (6,7). No previous reports have indicated that the proteins are usual components of olive oils. Recent studies from this laboratory have developed a methodology that allows for the determination of peptides and proteins in fats and oils (8). As a continuation of that study, the present investigation was undertaken for the systematic screening of olive oils from different origins and degrees of processing, to analyze if the presence of proteins was accidental in some oils or if proteins should be considered minor components of these oils. In addition, the influence of these compounds on the stability of the oils was also studied. EXPERIMENTAL PROCEDURESMaterials. Twenty-eight virgin olive oils and six refined olive oils were analyzed in this study (Table 1). Virgin olive oil samples were obtained from different olive varieties in differen...

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“…These carbonyl-amine reactions seem to be a group of gradual, partially reversible, universal, and inevitable side reactions in both food and biological systems. In addition, they may be also a protective mechanism by which endogenous antioxidants are generated (Alaiz et al 1995(Alaiz et al , 1996bHayase, 1996;Zamora et al, 1997).…”

Section: Future Trendsmentioning

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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Natural antioxidants produced in oxidized lipid/amino acid browning reactions

Cited by 23 publications

References 24 publications

Antioxidative Activity of Amino Phospholipids and Phospholipid/Amino Acid Mixtures in Edible Oils As Determined by the Rancimat Method

Antioxidative Activity of Amino Phospholipids and Phospholipid/Amino Acid Mixtures in Edible Oils As Determined by the Rancimat Method

Low molecular weight polypeptides in virgin and refined olive oils

The role of lipids in nonenzymatic browning

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