Precursors of damascenone in fruit juices

Skouroumounis, George K.; Massy‐Westropp, Ralph A.; Sefton, Mark A.; Williams, Patrick J.

doi:10.1016/s0040-4039(00)92682-0

Cited by 65 publications

(75 citation statements)

References 8 publications

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“…This powerful odorant is known to derive from the hydrolytic breakdown of several C 13 -norisoprenoidic polyols, which can occur in wines either as free volatiles or glycosides. 7,8,28 Levels of the glycosidic forms of one of these possible precursors, 3-hydoxy-7,8-dehydro-β-ionol, were found to decrease with MLF, suggesting a possible involvement of bacteria-mediated hydrolysis of this glycoside in the rate of formation of β-damascenone during our study. It should be noted that the analysis of a sample of experimental wine stored at −20 • C at the beginning of the experiment gave β-damascenone concentrations similar to the control (5 µg L −1 ), indicating that the possible influence of higher SO 2 levels in control wine on the evolution of β-damascenone in the course of the experiment 29 was negligible under our experimental conditions.…”

Section: Influence Of Mlf and O Oeni Strain On The Glycoside-relatedmentioning

confidence: 52%

The influence of malolactic fermentation and Oenococcus oeni strain on glycosidic aroma precursors and related volatile compounds of red wine

Ugliano

Moio

2006

J Sci Food Agric

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Free and glycosidically bound volatile compounds of red wine were measured after malolactic fermentation (MLF) with four different commercial starter cultures of Oenococcus oeni. MLF resulted in a significant decrease in the concentration of total glycosides, expressed as phenol-free glycosyl glucose. Gas chromatographic analyses of wine enzyme hydrolysates showed that the extent of hydrolysis of glycosides during MLF was dependent on both bacterial strain and chemical structure of the substrate. The highest decrease was observed for glycosidic precursors of primary terpene alcohols. Glycoside-related aroma compounds such as linalool, farnesol, and β-damascenone were increased after MLF with all the bacterial strains tested. Two of the strains were also able to release significant amounts of vinylphenols during MLF.

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Section: Influence Of Mlf and O Oeni Strain On The Glycoside-relatedmentioning

confidence: 52%

The influence of malolactic fermentation and Oenococcus oeni strain on glycosidic aroma precursors and related volatile compounds of red wine

Ugliano

Moio

2006

J Sci Food Agric

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“…In bacteria, Hasegawa et al (1984) have shown a metabolization of abscisic acid into dehydrovomifoliol, with vomifoliol as intermediate. Moreover, vomifoliol is present in grape as well, being one of the most abundant norisoprenoid (Skouroumounis et al 1992;Baumes et al 1994). Some metabolites detected under glycosylated form in this experiment were detected under free form as well when the cell suspension culture was supplemented with ß-ionone.…”

Section: Biotransformation Of Dehydrovomifoliolmentioning

confidence: 56%

Biotransformation of C13-norisoprenoids and monoterpenes by a cell suspension culture of cv. Gamay (Vitis vinifera)

Mathieu¹,

Wirth²,

Sauvage³

et al. 2009

Plant Cell Tiss Organ Cult

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A cell suspension culture of cv. Gamay was studied for its ability to metabolize two different C 13 -norisoprenoidic volatiles, b-ionone and dehydrovomifoliol, together with monoterpenes, geraniol and linalool, biogenetically common pathways sharing compounds. b-Ionone was totally metabolized leading to fourteen norisoprenoidic volatiles oxygenated mainly at carbons 3 or 4 of the cyclohexane ring or reduced at side chain. The biotransformation of dehydrovomifoliol was at a lesser extent, giving rise to oxygenated and reduced derivatives. The norisoprenoidic metabolites were present both under free and glycosylated forms. Geraniol and linalool were also metabolized, leading to several free and glycosylated compounds.

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“…This demonstrates that the b-D-glucosyl moiety at the C-3 position results in higher dehydration rates from 1 to 2 than the transformation of 1 with sugar residues at C-9 position. As suggested by Skouroumounis et al (1992), megastigma-4,6,7-triene-3,9-diol (3) and megastigma-3,5-dien-7-yn-9-ol (4) were identified as two intermediates in the transformation of 1 to damascenone. The glycoconjugates of 3 (3a and 3b), and 4 (4a) or the aglycon 4 were hypothetically proposed as intermediates involved in the pathways leading from the glycoconjugates of 1 (1a and 1b) to damascenone (Fig.…”

Section: Proposed Pathways For the Transformation Of Glycosidic Precumentioning

confidence: 92%

“…The two pathways suggest that megastigma-6,7-dien-3,5,9-triol (1) is a key intermediate in the formation of bdamasceone. Another important polyol, 3-hydroxy-7,8-didehydro-b-ionol (2), also has been determined as an important precursor of damascenone in wines (Skouroumounis, Massy-Westropp, Sefton, & Williams, 1992), and black teas (Kumazawa & Masuda, 2001). It was suggested by Puglisi, Elsey, Prager, Skouroumounis, and Sefton (2001) that 1 was quite labile to form 2 at room temperature and at pH 3.0 in an aqueous environment.…”

Section: Proposed Pathways For the Transformation Of Glycosidic Precumentioning

confidence: 99%

Formation of damascenone derived from glycosidically bound precursors in green tea infusions

et al. 2010

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a b s t r a c tDamascenone is well-known for its potent flavour with an extremely low odour threshold. Several glycosidically bound precursors of damascenone have been isolated from several plants, but little is known about their occurrences in green tea infusions. In this work, three major glycosidic precursors of damascenone, 9-O-b-D-glucopyranosyl-megastigma-6,7-dien-3,5,9-triol were isolated and identified in green tea infusions, and the stereochemistries at C-3 and C-9 positions of aglycone parts of the three glycosidic precursors were determined as (3S, 9R)-1a, (3R, 9R)-2a, and (3R, 9R)-2b, respectively. Compounds 1a, 2a, and 2b as well as 3-O-b-D-glucopyranosyl-megastigma-6,7-dien-3,5,9-triol (1b) were hydrolysed to form damascenone in a model system with strong acidic conditions (pH 2.0) and at high temperature (90°C). In contrast to hydrolysis of 2a and 2b, more damascenone was transformed from 1a and 1b. Furthermore, the b-D-glucosyl moiety at the C-3 position gave a higher dehydration rate from megastigma-6,7-dien-3,5,9-triol to 3-hydroxy-7,8-didehydro-b-ionol than compound 1a carrying the sugar residue at C-9 position. Interestingly, the four glycosidic precursors of damascenone were not hydrolysed to give damascenone under slightly acidic conditions (pH 5.4 and 120°C for 10 min), but they could be transformed to damascenone in the presence of green tea infusions even under the equal conditions.

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Precursors of damascenone in fruit juices

Cited by 65 publications

References 8 publications

The influence of malolactic fermentation and Oenococcus oeni strain on glycosidic aroma precursors and related volatile compounds of red wine

The influence of malolactic fermentation and Oenococcus oeni strain on glycosidic aroma precursors and related volatile compounds of red wine

Biotransformation of C13-norisoprenoids and monoterpenes by a cell suspension culture of cv. Gamay (Vitis vinifera)

Formation of damascenone derived from glycosidically bound precursors in green tea infusions

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