Light-induced changes in bottled white wine and underlying photochemical mechanisms

Bottled white wine may be exposed to UV-visible light for considerable periods of time before it is consumed. Light exposure may induce an off-flavor known as “sunlight” flavor, bleach the color of the wine, and/or increase browning and deplete sulfur dioxide. The changes that occur in bottled white wine exposed to light depend on the wine composition, the irradiation conditions, and the light exposure time. The light-induced changes in the aroma, volatile composition, color, and concentrations of oxygen and sulfur dioxide in bottled white wine are reviewed. In addition, the photochemical reactions thought to have a role in these changes are described. These include the riboflavin-sensitized oxidation of methionine, resulting in the formation of methanethiol and dimethyl disulfide, and the photodegradation of iron(III) tartrate, which gives rise to glyoxylic acid, an aldehyde known to react with flavan-3-ols to form yellow xanthylium cation pigments.     

Trichloroethylene transformation by natural mineral pyrite: the deciding role of oxygen

The transformation of trichloroethylene (TCE) in natural mineral iron disulfide (pyrite) aqueous suspension under different oxygen conditions was investigated in laboratory batch experiments. TCE transformation was pursued by monitoring its disappearance and products released with time. The effect of oxygen was studied by varying the initial dissolved oxygen concentration (DO(i)) inside each reactor. Transformation rates depended strongly on DO(i) in the system. In anaerobic pyrite suspension, TCE did not transform as it did under aerobic conditions. The transformation rate increased with an increase in DO(i). The TCE transformation kinetics was fitted to a pseudo-first-order reaction with a rate constant k (h(-1)) varying from 0.004 to 0.013 for closed systems with DO(i) varying from 0.017 to 0.268 mmol/L under the experimental conditions. In the aerobic systems, TCE transformed to several organic acids including dichloroacetic acid, glyoxylic acid, oxalic acid, formic acid, and finally to CO2 and chloride ion. Dichloroacetic acid was the only chlorinated intermediate found. Both TCE and the pyrite surface were oxidized in the presence of O2. Oxygen consumption profiles showed O2 was the common oxidant in both TCE and pyrite oxidation reactions. Ferric ion cannot be used as an alternative oxidant to oxygen for TCE transformation.     

Influence of light exposure, ethanol and copper(II) on the formation of a precursor for xanthylium cations from tartaric acid

The production of xanthylium cation pigments was greatly increased when an aged, tartaric acid buffered, 12% (v/v) aqueous ethanol solution was used in a model white wine system. This suggested the formation of a precursor to the pigments during the ageing of the tartaric acid solution. On examining factors responsible for the generation of tartaric acid oxidation products in wine-like solutions it was observed that on exposure of samples to sunlight, glyoxylic acid, a known precursor to xanthylium cations, was produced. The production of glyoxylic acid was achieved in both the absence and presence of ethanol and copper(II). Hydrogen peroxide was also detected in these solutions. The results were consistent with the presence of glyoxylic acid in the aged tartaric acid buffered, 12% (v/v) aqueous ethanol solution that had frequent aeration and periodic exposure to sunlight throughout its storage. Studies on the role of hydrogen peroxide in the production of glyoxylic acid were also investigated. On the addition of hydrogen peroxide to tartaric acid solutions, with heating at 45°C in darkness, glyoxylic acid was only determined in solutions without ethanol.     

Examination of the sulfur dioxide–ascorbic acid anti‐oxidant system in a model white wine matrix

The effectiveness of sulfur dioxide in inhibiting the ascorbic acid induced oxidation of (+)‐catechin in a matrix simulating white wine was investigated. At a sulfur dioxide:ascorbic acid mole ratio of 0.8:1.0, sulfur dioxide extended the delay prior to the onset of (+)‐catechin browning as measured by the increase in absorbance at 440 nm from 2 to 4 days post reaction initiation. The lengthening of the pre‐browning period was correlated with an increase in the time required to oxidise ascorbic acid completely, the sequence of events being loss of sulfur dioxide (day 3), loss of ascorbic acid (day 4) and on‐set of (+)‐catechin browning (day 4). Increasing the sulfur dioxide to ascorbic acid mole ratio to 3.0:1.0 inhibited the onset of (+)‐catechin browning over the 14‐day reaction period. This inhibition was achieved at considerable cost to the sulfur dioxide concentration, with the ratio of sulfur dioxide consumed to ascorbic acid oxidised being 1.7 compared with the expected fraction of 1.0. Reasons for the enhanced consumption of sulfur dioxide and the implications of this study for maintenance of quality in white wine production are discussed. Copyright © 2004 Society of Chemical Industry     

Effect of copper on oxidation of (+)-catechin in a model solution system

Summary Autoxidation of ( +)‐catechin in a model solution system, containing cupric ions, was monitored by high‐performance liquid chromatography with diode array detection. The rate of (+)‐catechin oxidation and the extent of browning increased with the copper concentration, showing an effect of copper on browning of flavanols. The progression of the reaction showed that the appearance of new compounds, which were initially absent in the mixture, was concomitant with (+)‐catechin decrease. Numerous reaction products, including both colourless compounds and pigments absorbing at 440, 460 and 550 nm, were detected. Among the colourless derivatives, four dimeric compounds, consisting of two catechin units linked by a carboxymethine bridge, were detected. Their formation involved the condensation of flavanols, mediated by glyoxylic acid, following a mechanism similar to that previously observed with iron. The yellowish compounds that were detected were identified as xanthylium salts and their corresponding esters, showing absorption maxima at 440 and 460 nm, respectively. Comparison of the results obtained with those reported with iron showed that copper ions play similar roles in enhancing the oxidation rate of (+)‐catechin and flavanols.     

Factors influencing the production and stability of xanthylium cation pigments in a model white wine system

The influence of various wine parameters on the production and stability of xanthylium cation pigments in a wine-like medium is reported. The xanthylium pigments have an absorbance maximum in the visible region at 440 nm that is close to the measured absorbance used by the wine industry to indicate the browning of wine (i.e. 420 nm). The results of this study show that iron is more efficient than copper in both the colouration and production of xanthylium cation pigments in wine-like solutions of tartaric acid and (+)-catechin. The non-flavonoid caffeic acid can inhibit the accumulation of the xanthylium cation pigments, despite the presence of metal ions, and also influence the stability of the pigment. Sunlight leads to a decrease in the concentration of xanthylium cation pigments while a temperature difference of 20 ^oC in the absence of light was observed to have little influence on concentration. The results suggest that the xanthylium cations are more likely to be a transitory species during white wine oxidation rather than accumulating pigments based on their instability with caffeic acid.     

Impact of the condition of storage of tartaric acid solutions on the production and stability of glyoxylic acid

The production and stability of glyoxylic acid was followed during the storage of tartaric acid solutions under various conditions. The solutions were prepared both with and without ethanol. Quantification of glyoxylic acid and other oxidation products, including hydrogen peroxide and formic acid, were performed using ion exclusion chromatography. Glyoxylic acid was only detected in tartaric acid samples that had been stored outdoors and sunlight was identified as the critical component of outdoor storage that allowed its formation. The hydrogen peroxide and glyoxylic acid generated under these conditions were of limited stability due to their reaction with each other to produce formic acid. The concentration of the glyoxylic acid was greatly increased when ethanol was omitted from the sample matrix. Copper(II) enhanced the stability of glyoxylic acid but slowed its production. The reaction pathway responsible for the sunlight-induced production and subsequent stability of glyoxylic acid is discussed.     

Interaction between Maillard reaction products and lipid oxidation in starch‐based model systems

The effect of Maillard reaction products (MRPs) on the kinetics of lipid oxidation in intermediate‐moisture model systems containing pregelatinised starch, glucose, lysine and soybean oil has been studied. The samples, either containing all components or excluding one or more of them, were heated at 100 °C for different times. Lipid oxidation and browning indices were measured and the results confirmed the ability of MRPs to retard peroxide formation. Under the conditions adopted, the rate of the Maillard reaction was increased by the presence of the oil and its oxidation products. The antioxidant action of MRPs was also evaluated using a peroxide‐scavenging test based on crocin bleaching. The results demonstrated that antioxidant activity developed with increased browning of the samples. © 2000 Society of Chemical Industry     

葡萄汁过量氧化研究进展

葡萄汁过量氧化是白葡萄酒酿造中的一项新技术，并逐渐引起了酿酒师的广泛重视。探讨了葡萄酒中类黄酮及其褐变机理；论述了过量氧化在实际应用中所涉及的工艺措施，如氧气供给数量、供给方式、分析控制以及SO2的添加等；讨论了过量氧化对葡萄酒微生物及其品质，如风味、色度及其香气等方面的影响；同时阐述了过量氧化存在的一些问题及其应用前景。     

Interactions between yeast, oxygen and polyphenols during alcoholic fermentations: Practical implications

During alcoholic fermentation, even when Saccharomyces cerevisiae cells have used the required oxygen for lipid synthesis, they can consume much more oxygen with no detrimental effect on the fermentation process. Under these conditions, most of the superfluous oxygen is consumed by yeasts by the partial functioning of several nonrespiratory oxygen consumption pathways, which are characterized by the production of reactive oxygen species (ROS). When excess oxygen is added to yeast cells, cell sterol content decreases, following the strong oxidation of intracellular sterols. During aging of fermented products in the presence of nonviable yeast lees (harvested at the end of alcoholic fermentation), the lees can consume oxygen for at least 3 years of the aging process. This oxygen consumption by yeast lees is related to moderate oxidation of yeast membrane lipids by the action of free radicals, strongly decreasing sterols in the yeast lees. The biochemical reactions involved in the oxygen consumption pathways during alcoholic fermentation may be the same as those responsible for oxygen consumption observed in yeast lees. Therefore, the cross-reactivity of complex plant polyphenols, tannins and yeast towards oxygen can easily occur during technological processes (alcoholic fermentation and wine aging). The micro-oxygenation of yeasts releases ROS during alcoholic fermentation and may favour the oxidation of wine phenolic compounds. As yeasts have much higher affinities for oxygen than plant polyphenols, viable yeast and yeast lees compete with phenolic compounds and then hinder the wine aging process. Also, the partial adsorption of plant polyphenols on yeast occurs during alcoholic fermentation, which modifies the overall reactivity of yeast and polyphenols towards oxygen.     

Phenolic colorants obtained by enzymatic synthesis using a fungal laccase in a hydro-organic biphasic system

The oxidation of ferulic acid by laccase from Myceliophthora thermophila was followed with high performance liquid chromatography (HPLC) in aqueous and hydro-organic medium. Results achieved in this study showed that the enzymatic activity and the stability of the products greatly varied depending on the nature of the reaction medium.The oxidation of ferulic acid in a biphasic hydro-organic system (perfectly mixed) consisting of ethyl acetate and sodium–phosphate buffer resulted in intermediate stable yellow products. The organic solvent which decreased the activity of the laccase and the rate of non-enzymatic reactions led to the stability of these intermediate products. Compared to the aqueous medium, the biphasic hydro-organic medium presents significant advantages such as increased effectiveness in the prevention of browning and an increased solubility of the resulting colored products. Thereby, the biphasic medium facilitates the separation of these products which were soluble only in the organic phase of this system.     

Kinetics of the inhibition of ascorbic acid browning by sulphite.

Despite differences in the structures of aldoses and ascorbic acid, ASA, the non-enzymic browning of the latter involves intermediates similar to those found in Maillard browning. The kinetics of the sulphite-inhibited browning of ASA suggest that, under anaerobic conditions, the rate of reaction of sulphite species, S(IV), is of first order with respect to S(IV). The possibility that S(IV) could catalyse the hydrolysis of the lactone ring of ASA is considered by reference to D-glucono-delta-lactone. Evidence is presented to suggest that, under aerobic conditions, autoxidation of ASA leads to the oxidation of S(IV). The composition of melanoidins from ASA-glycine mixtures is compared with that from arabinose-glycine; the former contain 2 x 5 times more ASA-derived residues per glycine molecule than arabinose-derived residues per glycine molecule in the latter. The implications of these findings to the mechanism of ASA browning are discussed.     

Nonenzymic browning of cauliflower on storage.

The nonenzymic browning of cauliflower homogenate was evaluated during storage at temperatures ranging between 40 degrees and 80 degrees C. In these accelerated tests, the reflectometric measurement was more sensitive and more reliable than the measurement of colour intensity of ethanolic extracts. The browning followed the kinetics of a first order reaction at higher temperatures and that of a zero order reaction at lower temperatures. The activation energy depended considerably on the reaction temperature. The rate of browning was only slightly affected by the addition of ferrous ions both in the absence and in the presence of oxygen. Results of model experiments show that the most important reaction under experimental conditions was probably the reaction of free amino-acids and other amine derivatives with quinones produced by oxidation of natural polyphenolic compounds. Red primary condensation products were transformed into brown pigments by subsequent secondary reactions.     

GROWTH OF AEROBIC WILD YEASTS

Wild yeasts of the genera Debaryomyces, Hansenula and Pichia are commonly considered to be associated with spoilage only under aerobic conditions. However, in pure cultures in either wort or a synthetic medium of yeast nitrogen base + 10% glucose, yeasts of these genera grew as well as a brewing strain of Saccharomyces cerevisiae under anaerobic conditions. Growth of S. cerevisiae was increased by the addition of unsaturated fatty acid (Tween 80) or ergosterol to the medium for anaerobic culture. No equivalent requirement was observed for the wild yeasts examined. Indeed, growth of the wild yeasts was often reduced by the addition of Tween 80, which as a surfactant prevented formation of the surface film of growth. Even under anaerobic conditions, these yeasts grew best with a surface pellicle. Although capable of good anaerobic growth in pure culture, growth of the wild yeasts was suppressed under anaerobic conditions in mixed culture with S. cerevisiae, simulating a contaminated brewery fermentation. However, the contaminants competed successfully with S. cerevisiae under aerobic conditions. There was no evidence of a “killer” effect, but prevention of pellicle formation, or production of inhibitory levels of pH or ethanol under anaerobic conditions could explain the suppression of wild yeasts under anaerobic fermentation conditions.     

Use of Active Packaging for Increasing Ascorbic Acid Retention in Food Beverages

ABSTRACT: A study on the influence of the type of container and storage temperature on ascorbic acid degradation and browning in a model system simulating a citrus juice is presented. The model system was packaged in glass jars, polyethylene terephthalate (PET) bottles, bottles of PET containing different percentages of oxygen scavengers, and bottles of PET blended with 6% nylon. Samples were stored at 5 °C to simulate the usual storage condition and at 35 °C to simulate a temperature abuse. The slowest ascorbic acid degradation and browning were obtained with PET + 3% oxygen scavengers. Glass and PET gave the worst results: the 1st due to the presence of pro-oxidants and the latter due to the oxygen permeability. In particular, concerning ascorbic acid degradation in glass containers at 35 °C, it was hypothesized that there are 2 simultaneously occurring reactions: the 1st directly related to aerobic oxidation and the 2nd primarily due to the anaerobic consumption of ascorbic acid, which becomes predominant when oxygen is totally exhausted. Results also demonstrated the possible replacement of the glass containers with polymeric ones in the beverage industry.     

Phospholipid oxidation and nonenzymatic browning development in phosphatidylethanolamine/ribose/lysine model systems

Fatty acid losses, lipid oxidation, pyrrole formation, and browning and fluorescence development were determined in four mixtures of phosphatidylethanolamine (PE), ribose (RI), and/or lysine (lys) incubated at 37 °C to study the influence of lipid oxidation on the Maillard reaction and vice versa. Under the conditions assayed, the amino group of PE was preferentially damaged compared with the amino group of lys. In addition, oxidized lipid/amino acid reactions produced more pyrrolization, browning and fluorescence than carbohydrate/amino acid reactions, but both oxidized lipid/amino acid and sugar/amino acid reactions were produced in the PE/RI/lys system and both of them were inhibited by the presence of the other. Thus, fewer RI/lys reaction products were produced in the PE/RI/lys system than in an analogous system with no PE added. All these results confirm that there is an interaction between lipid oxidation and the Maillard reaction, and both of them should be considered simultaneously to understand their consequences on foods when lipids, carbohydrates, and amino acids or proteins are present.     

贮藏过程中溶解氧对荔枝汁非酶褐变的影响

本文研究了荔枝汁在不同初始溶解氧浓度及有顶空氧存在的贮藏条件下的非酶褐变情况,采用PLSR进行分析揭示不同溶解氧浓度对荔枝汁非酶褐变的影响规律。结果表明:在0~3 d的贮藏期内,随着DOC的快速下降,低溶解氧和中溶解氧荔枝汁的L-AA进行有氧降解;在3 d~17 w的贮藏期内,DOC下降缓慢,趋于稳定,L-AA进行有氧降解和无氧降解,并以无氧降解为主。随着贮藏前期DOC和顶空氧浓度的快速下降,高溶解氧荔枝汁的L-AA持续进行有氧降解并在第4 w时基本全部降解完毕。三种溶解氧浓度的荔枝汁中的蔗糖均不断降解,但果糖和葡萄糖含量呈现先快速增加后减少的趋势。5-HMF和褐变指数不断地增加,溶解氧浓度越高,增加的越快。表儿茶素不断的降解,而芦丁含量比较稳定。在不同溶解氧浓度下,荔枝汁的非酶褐变是以L-AA降解及酚类物质氧化聚合为主,美拉德反应为辅。     

Copper(II)-mediated oxidation of (+)-catechin in a model white wine system

This study was undertaken to establish the role played by copper(II) in enhancing the rate of oxidation of flavanols. A model white wine system consisting of 12% (v/v) aqueous ethanol saturated with potassium hydrogen tartrate and adjusted to pH 3.2 was used to allow experimentation under well-defined conditions. (+)-Catechin was the oxidisable substrate and copper(II) concentrations up to 0.6 mg/L were employed. The model white wines were maintained at 45C to induce the browning process. Under these conditions an increase in absorbance at 440 nm occurred provided the copper(II) concentration was 0.3 mg/L or greater. The coloured species responsible for the increase in absorbance were identified as xanthylium cations, formed by linkage of two (+)-catechin molecules. Glyoxylic acid acted as the bridge between the phloroglucinol-type moiety of the (+)-catechin molecules. The production of the xanthylium cations was inhibited by ethanol and also by mannitol and the implications of these observations for a free-radical induced mechanism are discussed.     

Nonenzymatic Browning in Aseptically Packaged Orange Juice and Orange Drinks. Effect of Amino Acids, Deaeration, and Anaerobic Storage

Single strength orange juice and synthetic orange drinks containing 10% (v/v) orange juice and 0.4 and 0.8% w/w concentrations of each amino acid, aspartic acid, arginine, and 4-aminobutyric acid were aseptically packaged using 250 mL Tetra Brik Packs. Samples were stored at 24°C for 16 wk under anaerobic and aerobic conditions, and were tested every 4 wk for nonenzymatic browning, ascorbic acid (AA) retention, dehydroascorbic acid (DHAA) formation, and sensory changes. Deaeration and anaerobic storage resulted in increased retention of ascorbic acid. However, there was very little change in the flavor score, browning, color or change in the amino acid content of the different samples during the entire storage period.     

The impact of oxygen availability on stress survival and radical formation of Bacillus cereus

Both the growth and stress survival of two model Bacillus cereus strains, ATCC 14579 and ATCC 10987, were tested in three different conditions varying in oxygen availability, i.e., aerobic, microaerobic and anaerobic conditions. Both B. cereus strains displayed highest growth rates and yields under aerobic conditions, whereas the microaerobic and anaerobic cultures showed similar reduced growth performances. The cells grown and exposed microaerobically and anaerobically were more resistant to heat and acid than cells that were cultured and exposed aerobically. On the other hand, the anaerobically grown cells were more sensitive to hydrogen peroxide compared to the (micro)aerobically grown cells. The increased heat- and acid-induced inactivation in aerobic conditions appeared to be associated with intracellular accumulation of excess hydroxyl and/or peroxynitrite radicals, as determined by flow cytometry in combination with the fluorescent reporter dye 3′-(p-hydroxyphenyl) fluorescein. This suggests that radical formation may contribute to inactivation of bacteria in the presence of oxygen, such as in aerobic and microaerobic conditions. No evidence was found for radical formation upon exposure to salt and hydrogen peroxide. The increased resistance to heat and acid in microaerobic and anaerobic conditions shows that oxygen availability should be taken into account when behavior of bacteria, such as B. cereus, in food industry related conditions is investigated, because oxygen availability may affect the efficiency of food preservation conditions.