Reaction of oxidized lipids with protein Part 14. Aldolization reactions of lower alkanals in presence of nonlipidic substances

Pokorný, Jan; Janitz, W.; Víden, I.; Velı́šek, J.; Valentová, Helena; Davı́dek, J.

doi:10.1002/food.19870310115

Cited by 19 publications

(13 citation statements)

References 15 publications

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“…In this sense, amine compounds have been mentioned to play a catalytic effect on the condensation reaction between lipid oxidation compounds [45,46], being accorded an important effect of the amine structure on the fluorescent compound formation [47]. Indeed, an interesting relationship has been observed between the formation of interaction compounds during the storage/processing of foods and the pigmented and fluorescent granules found in human and animal tissues (lipofuscin) [48,49].…”

Section: Tab 4 CD (Absorption Coefficient) Formation In Frozen (mentioning

confidence: 94%

Lipid damage during frozen storage of Gadiform species captured in different seasons

Aubourg

Lago

Sayar

et al. 2007

Euro J Lipid Sci & Tech

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Quality loss of two gadiform fish species (blue whiting, Micromesistius poutassou; hake, Merluccius merluccius) during frozen storage (-30 and -10 7C; up to 12 months) was studied. For this, hydrolytic (formation of free fatty acids, FFA) and oxidative (conjugated dienes, peroxide and interaction compound formation) lipid damage were analysed. For both species, individual fishes captured in two different trials (May and November) were considered. Increasing (p ,0.05) lipid hydrolysis and oxidation (peroxide and interaction compound formation) were observed for all kinds of samples throughout the frozen storage. Interaction compound detection by fluorescence analysis showed the best correlation values with storage time. Some higher (p ,0.05) hydrolysis development could be observed in hake captured in May than in its counterpart from the November trial, while frozen blue whiting did not provide definite differences for FFA formation between both trials. Concerning peroxide formation, higher (p ,0.05) values were obtained for individual blue whiting and hake captured in November when compared to their corresponding May fish for both frozen storage conditions. Interaction compound formation was also found to be higher (p ,0.05) for November hake fish than for its counterpart captured in May, while blue whiting did not provide definite differences between trials.

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Section: Tab 4 CD (Absorption Coefficient) Formation In Frozen (mentioning

confidence: 94%

Lipid damage during frozen storage of Gadiform species captured in different seasons

Aubourg

Lago

Sayar

et al. 2007

Euro J Lipid Sci & Tech

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“…It has been reported in the literature that amino acids as well as small peptides can catalyze aldol reactions. [13][14][15] To explain the stereoselectivity obtained in specific cases, a mechanism was proposed in which the ketone donor reacts with the amino acid with the formation of an enamine. Afterward, the acceptor aldehyde reacts with the chiral enamine and, upon hydrolysis, an enantiomerically enriched aldol product can be generated.…”

Section: ' Results and Discussionmentioning

confidence: 99%

Model Studies on the Pattern of Volatiles Generated in Mixtures of Amino Acids, Lipid-Oxidation-Derived Aldehydes, and Glucose

Adams

Kitrytė

Venskutonis

et al. 2011

J. Agric. Food Chem.

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The development of flavor and browning in thermally treated foods results mainly from the Maillard reaction and lipid degradation but also from the interactions between both reaction pathways. To study these interactions, we analyzed the volatile compounds resulting from model reactions of lysine or glycine with aldehydes originating from lipid oxidation [hexanal, (E)-2-hexenal, or (2E,4E)-decadienal] in the presence and absence of glucose. The main reaction products identified in these model mixtures were carbonyl compounds, resulting essentially from amino-acid-catalyzed aldol condensation reactions. Several 2-alkylfurans were detected as well. Only a few azaheterocyclic compounds were identified, in particular 5-butyl-2-propylpyridine from (E)-2-hexenal model systems and 2-pentylpyridine from (2E,4E)-decadienal model reactions. Although few reaction products were found resulting from the condensation of an amino acid with a lipid-derived aldehyde, the amino acid plays an important role in catalyzing the degradation and further reaction of these carbonyl compounds. These results suggest that amino-acidinduced degradations and further reactions of lipid oxidation products may be of considerable importance in thermally processed foods.

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“…In the ciise o f MDA iis only carbonyl compound a lower fluorescence content had been obtained (Kikugawa et al, 1981a), although the same product as that of the reaction in presence of acetaldehyde was detected. Aldolization may be involved in these reactions; it has been observed in the presence of non-lipid compounds such as amines (Pokorny et al, 1987), and condensation of alkanals to give alk-2-enals is catalyzed by amino-containing compounds (Suyama er al., 1981). Kikugawa & Sawamura (1987) generalized this Hantzsch reaction to a wide range of aliphatic aldehydes with methylamine.…”

Section: Lnteraction With Aminesmentioning

confidence: 99%

Interaction of malondialdehyde with biological molecules — new trends about reactivity and significance

Aubourg¹

1993

Int J of Food Sci Tech

128

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Malonyldialdehyde (malondialdehyde, MDA) is one of the most significant of the wide range of metabolic or deteriorative products of lipid damage. Its formation during food processing and storage is widely used in quality control. Its ability to react with -NH2 groups is also of great carcinogenic or mutagenic interest because of its possible interaction with important constituents (e.g. free amino acids, proteins, nucleic acids, and amino phospholipids) of foods during and after processing. Special attention has been given to the role played by MDA in the formation of the age pigments, commonly named as 'lipofuscin'.The present review compiles the general characteristics that have made MDA the most widely studied lipid metabolite, and the progress achieved in knowledge of MDA reactivity with biological molecules. The special stress given to the structural elucidation of the structures of these products have led to a new perspective about the role played by MDA.

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Reaction of oxidized lipids with protein Part 14. Aldolization reactions of lower alkanals in presence of nonlipidic substances

Cited by 19 publications

References 15 publications

Lipid damage during frozen storage of Gadiform species captured in different seasons

Lipid damage during frozen storage of Gadiform species captured in different seasons

Model Studies on the Pattern of Volatiles Generated in Mixtures of Amino Acids, Lipid-Oxidation-Derived Aldehydes, and Glucose

Interaction of malondialdehyde with biological molecules — new trends about reactivity and significance

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