The detection of ?-dicarbonyl compounds in wine by formation of quinoxaline derivatives

Revel, Gilles de; Pripis-Nicolau, L.; Barbe, Jean‐Christophe; Bertrand, Alain

doi:10.1002/(sici)1097-0010(20000101)80:1<102::aid-jsfa493>3.0.co;2-y

Cited by 89 publications

(100 citation statements)

References 12 publications

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“…In foods, α-DCs have been identified in lactose-hydrolyzed ultra-high-temperature milk, honey, beer, wine, coffee, and soft drinks [16][17][18][19][20][21][22]. Lo et al identified and quantified glyoxal (GO), methylglyoxal (MGO), and 3-deoxy-D-erythro-hexos-2-ulose (3-deoxyglucosone (3-DG)) in several HFCS samples [20].…”

Section: Introductionmentioning

confidence: 99%

Identification and quantification of six major α-dicarbonyl process contaminants in high-fructose corn syrup

et al. 2012

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High-fructose corn syrup (HFCS) is a widely used liquid sweetener produced from corn starch by hydrolysis and partial isomerization of glucose to fructose. During these processing steps, sugars can be considerably degraded, leading, for example, to the formation of reactive α-dicarbonyl compounds (α-DCs). The present study performed targeted screening to identify the major α-DCs in HFCS. For this purpose, α-DCs were selectively converted with o-phenylendiamine to the corresponding quinoxaline derivatives, which were analyzed by liquid chromatography with hyphenated diode array-tandem mass spectrometry (LC-DAD-MS/MS) detection. 3-Deoxy-D-erythro-hexos-2-ulose (3-deoxyglucosone), D-lyxo-hexos-2-ulose (glucosone), 3-deoxy-D-threo-hexos-2-ulose (3-deoxygalactosone), 1-deoxy-D-erythro-hexos-2,3-diulose (1-deoxyglucosone), 3,4-dideoxyglucosone-3-ene, methylglyoxal, and glyoxal were identified by enhanced mass spectra as well as MS/MS product ion spectra using the synthesized standards as reference. Addition of diethylene triamine pentaacetic acid and adjustment of the derivatization conditions ensured complete derivatization without de novo formation for all identified α-DCs in HFCS matrix except for glyoxal. Subsequently, a ultra-high performance LC-DAD-MS/MS method was established to quantify 3-deoxyglucosone, glucosone, 3-deoxygalactosone, 1-deoxyglucosone, 3,4-dideoxyglucosone-3-ene, and methylglyoxal in HFCS. Depending on the α-DC compound and concentration, the recovery ranged between 89.2% and 105.8% with a relative standard deviation between 1.9% and 6.5%. Subsequently, the α-DC profiles of 14 commercial HFCS samples were recorded. 3-Deoxyglucosone was identified as the major α-DC with concentrations up to 730 μg/mL HFCS. The total α-DC content ranged from 293 μg/mL to 1,130 μg/mL HFCS. Significantly different α-DC levels were not detected between different HFCS specifications, but between samples of various manufacturers indicating that the α-DC load is influenced by the production procedures.

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Section: Introductionmentioning

confidence: 99%

Identification and quantification of six major α-dicarbonyl process contaminants in high-fructose corn syrup

et al. 2012

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“…Headspace SPME (HS-SPME) [1,61] is an eVective and solventless sampling technique especially suitable for quantiWcation of volatile analytes, because it reduces interferences from other, non-volatile, wine constituents. Hayasaka et al [26] described a simple and eVective method for quantiWcation of diacetyl by use of HS-SPME coupled to GC-MS. Other workers have described methods for the quantiWcation of diacetyl and other dicarbonyl compounds [14], and several aldehydes [20,21,59], by use of derivatisation procedures before chromatographic analysis. Because the eVects of MLF on aldehydes have not yet been characterised, mainly because of a lack of analytical data, a robust method for simultaneous determination of diacetyl and aldehydes in wine would provide insight into changes associated with LAB during MLF.…”

Section: Introductionmentioning

confidence: 99%

Comparative metabolic profiling to investigate the contribution ofO. oeniMLF starter cultures to red wine composition

Malherbe

Tredoux

Nieuwoudt

et al. 2012

Journal of Industrial Microbiology and Biotechnology

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In this research work we investigated changes in volatile aroma composition associated with four commercial Oenococcus oeni malolactic fermentation (MLF) starter cultures in South African Shiraz and Pinotage red wines. A control wine in which MLF was suppressed was included. The MLF progress was monitored by use of infrared spectroscopy. Gas chromatographic analysis and capillary electrophoresis were used to evaluate the volatile aroma composition and organic acid profiles, respectively. Significant strain-specific variations were observed in the degradation of citric acid and production of lactic acid during MLF. Subsequently, compounds directly and indirectly resulting from citric acid metabolism, namely diacetyl, acetic acid, acetoin, and ethyl lactate, were also affected depending on the bacterial strain used for MLF. Bacterial metabolic activity increased concentrations of the higher alcohols, fatty acids, and total esters, with a larger increase in ethyl esters than in acetate esters. Ethyl lactate, diethyl succinate, ethyl octanoate, ethyl 2-methylpropanoate, and ethyl propionate concentrations were increased by MLF. In contrast, levels of hexyl acetate, isoamyl acetate, 2-phenylethyl acetate, and ethyl acetate were reduced or remained unchanged, depending on the strain and cultivar evaluated. Formation of ethyl butyrate, ethyl propionate, ethyl 2-methylbutryate, and ethyl isovalerate was related to specific bacterial strains used, indicating possible differences in esterase activity. A strain-specific tendency to reduce total aldehyde concentrations was found at the completion of MLF, although further investigation is needed in this regard. This study provided insight into metabolism in O. oeni starter cultures during MLF in red wine.

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“…The glyoxal and methylglyoxal in the oak-powder extracts were measured by gas chromatography-mass spectrometry by the method developed by De Revel et al 21) Water (15 mL) and the internal standards, 1.2 g/L of 2,3-hexanedione in 50% aqueous ethanol (25 mL) and 6.5 g/L of o-phenylenediamine (2.5 mL), were added to the oakpowder extract (10 mL), and the pH was adjusted to pH8 using a sodium hydroxide aqueous solution. The solution was heated for 3 h at 60 C, and cooled to room temperature, after which a 1-mL sample was loaded onto a diatomite column and eluted using 5 mL of dichloromethane.…”

Section: Methodsmentioning

confidence: 99%

Lignin Is Linked to Ethyl-Carbamate Formation inUme(Prunus mume) Liqueur

Hashiguchi

Izu

Sudo

2012

Bioscience, Biotechnology, and Biochemistry

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The detection of ?-dicarbonyl compounds in wine by formation of quinoxaline derivatives

Cited by 89 publications

References 12 publications

Identification and quantification of six major α-dicarbonyl process contaminants in high-fructose corn syrup

Identification and quantification of six major α-dicarbonyl process contaminants in high-fructose corn syrup

Comparative metabolic profiling to investigate the contribution ofO. oeniMLF starter cultures to red wine composition

Lignin Is Linked to Ethyl-Carbamate Formation inUme(Prunus mume) Liqueur

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