Flavor Formation in Meat-Related Maillard Systems Containing Phospholipids

Mottram, Donald S.; Salter, Linda J.

doi:10.1021/bk-1989-0409.ch041

Cited by 17 publications

(13 citation statements)

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“…The detection of long-chain pyridines and pyrroles in the reactions between glycine with ribose and phospholipid, and the additional formation of alkyl and alkenylthiophenes, thiapyrans and alkanethiols in the presence of cysteine have been described previously (Salter et all988; Farmer et a1 1989; Mottram and Salter 1989). The reaction of unsaturated aldehydes with either glycine, cysteine, ammonia or hydrogen sulphide is responsible for the formation of these compounds and must account, in part, for the observed depletion of the aldehydes.…”

Section: A Ldehy Desmentioning

confidence: 96%

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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Section: A Ldehy Desmentioning

confidence: 96%

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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“…However, the relative amounts of the three alkylthiophenes in the PCcontaining runs do not reflect the extreme preponderance of 2,4decadienal over the other dienals. A compound with a mass spectrum very similar to that of 2-hexylthiophene, but with a retention time close to that of 2-heptylthiophene, was tentatively identified as 2-pentylthiapyran (Mottram and Salter 1989). In our previous paper this compound was incorrectly identified as 2-heptylthiophene (Whitfield et al 1988).…”

Section: Compounds Formed Only In the Presence Of Lipid ( A )mentioning

confidence: 99%

Interaction of lipid in the maillard reaction between cysteine and ribose: The effect of a triglyceride and three phospholipids on the volatile products

Farmer¹,

Mottram²

1990

J Sci Food Agric

126

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The inclusion of phospholipid in the Maillard reaction between cysteine and ribose is known to modify the volatile aroma compounds produced. The contributions made to the headspace volatiles by 60 major products of this reaction have been compared for four digerent lipids and their effect on aroma quality noted.The results described demonstrate marked dissimilarities between the behaviour of the four lipids. The most noticeable distinction was between the effect of triglyceride and the three phospholipids, but there were also variations in the way that each of the three phospholipids participated in the Maillard reaction. As well as displaying marked differences in volatile products, reaction mixtures containing the four lipids possessed distinct aroma characteristics; the phospholipids containing phosphatidylethanolamine conferred the most meat-like odour. These differences appear to be caused by the dissimilar fatty acid compositions and polar moieties. Thus this study underlines the importance of lipid interaction in the Maillard reaction for the formation of flavour.

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“…Copyright CRC Press, Inc., Boca Raton, FL. ) and of cysteine/ribose, both in the presence and absence of lecithin (Whitfield et aI., 1988;Mottram and Salter, 1989;Mottram, 1987;Salter et al, 1988). The same overall effect was observed in both cases (i.e.…”

Section: Lipid Oxidation/degradationmentioning

confidence: 77%

“…For example, the reaction of ethane-l,2-dithiolfacetaldehyde/H2S gives rise to 2-methyl-l,3-dithiolane (13) and 3-methyl-l,2,4-trithiane (11) (Tressl et al, 1983). Further examples of Figure 2.1 compounds arising from Maillard type reactions are thiazole (19) from cysteine/pyruvaldehyde (Kato et al, 1973), 2,4,5-trimethyloxazole ~) from cysteine/butanedione (Ho and Hartman, 1982), thiophene-2-carboxaldehyde (ll) (Scanlan et al, 1973), 3-methyl-l,2,4-trithiane (11) and thialdine @) (de Rijke et al, 1981) from cysteine/glucose; 3-methyl-l,2,4-trithiane (11) and 2,4-dimethyl-5-ethylthiazole (W from cysteine/cystine-ribose (Mulders, 1973), 2-methylfuran-3-thiol (1), 2-methyl-3-(methylthio)furan (~ and 2,4-dimethyl-5-ethylthiazole (21) from cysteine/ribose Farmer et ai., 1989;Mottram and Salter, 1989;; Mottram and Leseigneur, 1990), methional (1) and 2-methyl-3-(methylthio)furan (H) from methionine/reducing sugar (Tressl et ai., 1989) and the 2-and 3methylcyclopentanones (~, ~) from cyclotene/H2S/NH3 reaction (Nishimura et al, 1980).…”

Section: Effect Of Heat On Sugars And/or Amino Acidsmentioning

confidence: 99%

“…For some compounds in the cysteine system, e.g. 2-methylfuran-3-thiol (1) and thiophene-2-thiol, the decrease was as much as 65% or more (Mottram and Salter, 1989). This is explained by competition by lecithin degradation products for H2S and NH3 derived from cysteine, and this was proved to occur by the additional presence in the reaction product mixture of some different heterocycles known to arise from such reactions.…”

Section: Lipid Oxidation/degradationmentioning

confidence: 99%

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