Nonenzymic browning. VIII. Autoxidation and browning reactions of phosphatidylethanolamine

Pokorný, Jan; Tai, Phan-trong; Janícék, G.

doi:10.1007/bf01140366

Cited by 13 publications

(6 citation statements)

References 18 publications

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“…Such an acid would be eluted only with a mixture of chloroform, methanol ayd ammonia (fraction No. 8 in Table z), however, it is probable that the corresponding ammonium salt has been formed during the passage through the column so that the isolated fraction had the phosphorus : nitrogen ration equal to I : I. In agreement with previous results [14], only polyenoic and partially, dienoic acids of phosphatidylethanolamine were destroyed during the autoxidation at room temperature ( Table I) The spectral evidence of conjugated unsaturated imines suggests the mechanism (11).…”

supporting

confidence: 88%

Lipid Oxidation. Part 3. Oxidation of Egg Phosphatidylethanolamine

Pokorný

Tai

Janícék

1976

Nahrung

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Phosphatidylamine isolated from egg yolk phospholipids was autoxidized at 60 degrees C. Oxidation products were separated by thin layer chromatography on silica gel and by column chromatography of DEAE-cellulose. The fractions were characterized by UV and IR spectra and by chemical analysis. Polyunsaturated fatty acids were destroyed during the oxidation, the content of primary amino groups decreased and imine derivatives appeared.

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supporting

confidence: 88%

Lipid Oxidation. Part 3. Oxidation of Egg Phosphatidylethanolamine

Pokorný

Tai

Janícék

1976

Nahrung

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“…The reaction between cdrbonyl compounds and ethanolamine has also been shown to give browning (Suyama and Adachi 1979;Husain et af 1986). It has been suggested that the ethanolamine group may react with either the hydroperoxides themselves or with aldehydes derived from them to give unstable Schiff bases which react further to give brown pigments by polycondensation reactions with aldehydes (Pokorny et al 1973(Pokorny et al , 1990Tai rt al 1974).…”

Section: Volatiles From the Degradation Of Lipids Heated Alonementioning

confidence: 99%

Effect of cysteine and ribose on the volatile thermal degradation products of a triglyceride and three phospholipids

Farmer¹,

Mottram

1992

J Sci Food Agric

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Abstract:The effect of the Maillard reaction on the volatile products of the degradation of lipids was investigated using an aqueous model system. This paper reports the changes in amounts of selected aliphatic oxidation products formed when beef triglyceride, beef phospholipid, egg phosphatidylcholine and egg phosphatidylethanolamine were heated with cysteine and ribose. The thermal degradation products of these lipids were modified considerably in the presence of cysteine and ribose. The most pronounced alteration was a reduction in the amounts of aldehydes detected, especially unsaturated aldehydes. However, this does not appear to constitute an overall antioxidative effect as ketones, also derived from the oxidation of lipid. showed little change. The I-alcohols and 2-alkylfurans were increased when cysteine and ribose were heated with phosphatidylcholine, but not with the other lipids. While the effect on alcohols and furans is not fully understood, the depletion of aldehydes is thought to be caused by reactions with the amino or thiol groups of the amino acid. Reactions with amino groups are also believed responsible for the lower levels of unsaturated aldehydes formed from phospholipids containing the ethanolamine moiety.

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“…Indeed, the most remarkable difference between PC and PE is not the fatty acid composition, but the polar moiety, which can be involved in chemical reactions. For example, the primary amino group of PE may react with either the hydroperoxides or the aldehydes derived from them to give unstable Schiff bases, which may further react to give brown pigments ( − ). As a result, such secondary reactions could contribute to degradation of odorants formed and, thus, affect the final levels of odorants.…”

Section: Discussionmentioning

confidence: 99%

A New Insight into the Formation of Odor Active Carbonyls by Thermally-Induced Degradation of Phospholipids in Self-Assembly Structures

Lin

Leser

Löliger

et al. 2004

J. Agric. Food Chem.

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The role of molecular organization in heated aqueous dispersions of egg phosphatidylcholine (PC) and egg phosphatidylethanolamine (PE) was studied with respect to the formation of key odorants. Evidence was found for the crucial role of self-assembly structures adopted by phospholipid molecules on the quantitative composition of volatile constituents. The concentrations of seven aldehydes and one vinyl ketone were determined by isotope dilution assay in heated aqueous dispersions of PC and PE present in various ratios. Addition of PE to PC drastically decreased the amount of (E,E)-2,4-decadienal formed, which cannot be explained by the differences in the fatty acid composition of PC and PE. The free amino group in PE does not explain this phenomenon either, as replacing PE by phosphatidic acid distearylester also reduced the amounts of (E,E)-2,4-decadienal. We suggest that the type of self-assembly structure adopted by phospholipids in water significantly influences the reaction yields. However, the mechanisms leading to the preferred formation of phospholipid-derived odorants in a lamellar phase, as compared to the reversed hexagonal phase, remain unknown.

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Nonenzymic browning. VIII. Autoxidation and browning reactions of phosphatidylethanolamine

Cited by 13 publications

References 18 publications

Lipid Oxidation. Part 3. Oxidation of Egg Phosphatidylethanolamine

Lipid Oxidation. Part 3. Oxidation of Egg Phosphatidylethanolamine

Effect of cysteine and ribose on the volatile thermal degradation products of a triglyceride and three phospholipids

A New Insight into the Formation of Odor Active Carbonyls by Thermally-Induced Degradation of Phospholipids in Self-Assembly Structures

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