Effect of phospholipid on the formation of volatile heterocyclic compounds in heated aqueous solutions of amino acids and ribose

Abstract

The concentrations of 68 heterocyclic compounds produced by heating a series of amino acid-ribose and lecithin-amino acid-ribose reaction mixtures at 140°C for 1 h were measured, after headspace collection on Tenax GC, by capillary gas chromatography-mass spectrometry. The amino acids studied were glycine, lysine and cysteine, and the classes of heterocyclic compounds quantified were pyrazines (14), pyridines (7), jkrans (14), thiophenes (26) and thiazoles (7). The studies showed that the addition of lecithin to the simple Maillard reaction mixtures led to a reduction in the concentrations of many of the heterocyclic compounds formed in these reactions. These findings support an earlier observation that phospholipids in foodstuffs, such as meat products, could exert a quenching effect on the amount of heterocyclic compounds formed in Maillard reactions during the cooking of food. A number of volatile compounds formed by the reaction of lipid degradation products with Maillard reaction intermediates were also identified.

The role of sulfur chemistry in thermal generation of aroma

“…These disulfides exhibit, in general, meaty, roasted aromas and their formation is influenced by phospholipids. Other heterocyclic compounds are quenched, too, by the presence of lecithin in the Maillard reaction (Whitfield et al, 1988). Also, unsaturated fatty acids or fatty acid esters impeded the formation of many volatiles including 2-methyl-3-furanthiol and 2-furanmethanethiol in a heated aqueous L-cysteine/ribose system .…”

The effect of pH on the formation of volatile compounds produced by heating a model system containing 5’-Imp and cysteine

“…2,3-dihydro-6-methylthieno [2,3c] 41 found that concentrations of nitrogen-containing heterocyclic compounds were reduced in systems containing cysteine and ribose, compared with other amino acids. Five thiazoles, including a series of acylthiazoles [16,42,44, 53] and a benzothiazole [75], were generated in the 5'-IMP/cysteine mixtures.…”

“…Four alkylfurans containing chains of C1-C5 [18,24,41,45], together with two furylketones [34,51] and two acylfurans [27,39] were formed. Another group of furans identified were furfural [15] and its derivatives [30,32,48, 64] and 4-hydroxy-5-methyl-3(2H)-furanone [21].…”

Effects of ribose to cysteine ratios on the formation of volatile compounds from the Maillard reaction in supercritical carbon dioxide

“…Furfural, an important intermediate in Maillard reaction, can be formed from ribose following a pathway involving the elimination of a hydroxyl group from the 1, 2-enediol form of the Amadori rearrangement product (ARP) to give 3-deoxypentose which yields furfural through dehydration and cyclisation (Whitfield et al, 1988). Furfural can also be derived from ribose directly via two steps of dehydration in acidic systems.…”

“…3-Mercapto-2-pentanone and 2-mercapto-3-pentanone are reduction products from 2, 3-pentanedione, which is the degradation product from HMF (Whitfield, Mottram, Brock, Puckey, & Salter, 1988). As shown in Table 2, 3-mercapto-2-pentanone favoured in SC-CO 2 and large amount of ribose presented, while the formation of 2-mercapto-3-pentanone was inhibited in SC-CO 2 -treated mixtures at reactant ratios of 3:1 and 1:1.…”