Assaying α-Dicarbonyl Compounds in Wine: A Complementary GC–MS, HPLC, and Visible Spectrophotometric Analysis

Abstract

We used a facile, aqueous reaction coupled with gas chromatography–mass spectrometry (GC–MS), visible spectrophotometry, and high performance liquid chromatography (HPLC) to quantify the amounts of α-dicarbonyl compounds in wine samples. The aqueous reaction between an α-dicarbonyl compound and o-phenylenediamine yields a highly stable quinoxaline molecule with an absorbance maximum of 315 nm. GC–MS is used to identify each quinoxaline via mass. Likewise, owing to the similar absorption properties of the quinoxaline products, visible spectrometry is not useful for quantitation although it reveals the absorbance maximum to use for optical detection of the quinoxalines by HPLC. The analytical techniques used in this experiment complement each other since visible spectrophotometry is needed to determine the absorption wavelength, which is used for HPLC analysis; and HPLC is used for quantitation, while GC–MS is used to confirm the identities of the reaction products.

Capillary gas chromatographic determination of methylglyoxal from serum of diabetic patients by precolumn derivatization with 1,2-diamonopropane

“…Recently, stilbenediamine (1,2-diamino-1,2-diphenylethane) has been used as a derivatizing reagent for HPLC determination of MGo using UV detection with detection limit of 76 ng/ml [24]. The gas chromatographic determination of MGo and (DMGo) involve mainly o- (2,3,4,5,6-pentafluorobenzyl) hydroxylamine hydrochloride [14,25,26], cystamine [27], o-phenylenediamine [28], or 4,5-dichloro-1,2-phenylenediamine as a derivatizing reagents [29]. The determination is based on mass spectroscopic, thermoionic or electron capture detections.…”

Rapid analysis of α‐dicarbonyl compounds by laser desorption/ionization mass spectrometry using 9‐(3,4‐diaminophenyl)acridine (DAA) as a reactive matrix

“…While there is significant error in the values reported due to the relative irreproducibility of MALDI MS irrespective of the target surface, it can be concluded that the hydrophobic plate does not significantly improve the sensitivity or shot‐to‐shot reproducibility of this method and, thus, a regular low‐cost stainless steel MALDI target is sufficient for the analysis. It is crucial to note that the DLs reported here for α ‐dicarbonyls are still lower than those obtained by other techniques, such as CE with diode‐array detection and, hence, use of the modified plate might be favorable for certain applications 2–4…”

“…α ‐Dicarbonyls are a commonly occurring class of compounds that, because of their implications for human health, have attracted the attention of researchers from diverse scientific disciplines such as water quality chemistry, food chemistry, and medical research 1–6. Pyruvic aldehyde (methylglyoxal) has been identified as a priority and potentially harmful disinfection by‐product in ozonated drinking water 1.…”

“…Pyruvic aldehyde (methylglyoxal) has been identified as a priority and potentially harmful disinfection by‐product in ozonated drinking water 1. Methylglyoxal and glyoxal are reactive intermediates produced from non‐enzymatic glycation (Maillard reaction) and are clinically significant compounds since they are known to react with proteins, basic phospholipids and nucleotides to form advanced glycation end products, which are possible indicators of chronic and age‐related diseases, such as diabetes mellitus and Alzheimer's disease 2–4. Dicarbonyl compounds have also been found among the large number of toxic compounds present in cigarette smoke and are, thus, considered important by environmental toxicologists 5.…”

“…Analysis of these compounds has traditionally been accomplished by reaction of the α ‐dicarbonyls with o ‐phenylenediamine to form stable UV‐active quinoxalines (with a notable absorbance maximum of 315 nm), which are separated by high‐performance liquid chromatography (HPLC) or capillary electrophoresis (CE) and detected by UV spectrophotometry 2–6. Current trends in chemical analysis, however, demand high sensitivity and high sample throughput methods, especially in clinical applications where numerous samples must be analyzed in a short period of time.…”