Approaches to wine aroma: release of aroma compounds from reactions between cysteine and carbonyl compounds in wine

Under conditions close to those of wine, that is, low pH, aqueous medium, and low temperatures, this work examines the role of carbonyl (acetoin and acetol) and dicarbonyl (glyoxal, methylglyoxal, diacetyl, and pentane-2,3-dione) compounds associated with cysteine in the formation of odorous products. In particular, thiazole, 4-methylthiazole, 2-acetylthiazole, and trimethyloxazole and two sulfur and oxygenated heterocyclic compounds, 2-furanmethanethiol and thiophene-2-thiol, are examined. For thiophene-2-thiol, the reactional mechanism is proposed. Attempts were made to detect these compounds in wines from various origins. Certain molecules were identified for the first time in wine.     

Evolution of the aroma profile of sherry wine vinegars during an experimental aging in wood

Changes in the aroma profile of five Sherry wine vinegars submitted to an experimental static aging in wood were followed along 24 months. Eighteen volatile compounds were determined by GC-FID. The results were subjected to multivariate analyses: principal component analysis and linear discriminant analysis. The aroma profile of vinegar can be useful to discriminate vinegars produced from different substrates or with different aging times. During the experimental aging, volatile compounds such as methyl acetate, methanol, diacetyl, and gamma-butyrolactone underwent significant concentration increases. Moreover, the initial ethanol content of vinegars is a factor in the final aromatic richness. The formation of ethyl acetate stood out in samples with an initial ethanol content of approximately 2 alcoholic degrees.     

Reconstitution of the flavor signature of Dornfelder red wine on the basis of the natural concentrations of its key aroma and taste compounds

By application of aroma extract dilution analysis (AEDA) on the volatile fraction isolated from a Dornfelder red wine, 31 odor-active compounds were identified by means of HRGC-MS and comparison with reference compounds. A total of 27 odorants, judged with high FD factors by means of AEDA, was quantitated by means of stable isotope dilution assays, and acetaldehyde was determined enzymatically. In addition, 36 taste-active compounds were analyzed by means of HPLC-UV, HPLC-MS/MS, and ion chromatography. The quantitative data obtained for the identified aroma and taste compounds enabled for the first time the reconstruction of the overall flavor of the red wine. Sensory evaluation of both the aroma and taste profiles of the authentic red wine and the recombinate revealed that Dornfelder red wine was closely mimicked. Moreover, it was demonstrated that the high molecular weight fraction of red wine is essential for its astringent taste impression. By comparison of the overall odor of the aroma recombinate in ethanol with that of the total flavor recombinate containing all tastants, it was shown for the first time that the nonvolatile tastants had a strong influence on the intensity of certain aroma qualities.     

不同酿造工艺对毛葡萄酒香气的影响

为探索酿造工艺对毛葡萄酒风味的影响,利用GC/MS法对秦巴山区野生毛葡萄在两种工艺条件下酿造的葡萄酒的香气成分进行了研究。结果表明：用传统工艺及CO₂浸渍工艺酿造的毛葡萄酒醇类相对含量最高,其中以苯乙醇、戊醇含量最高。在酯类、酮类、酚类方面,两种工艺酿造的原酒比陈酿6个月的酒种类少,相对含量低;而对于其他香气成分,则是原酒高于陈酿6个月的酒。说明一定时间的陈酿对于毛葡萄酒的香气质量有所提高。通过对两种工艺的综合比较发现,传统工艺酿造的原酒香气质量优于CO₂浸渍工艺酿造原酒;但经过6个月的陈酿后,CO₂浸渍工艺酿造酒香气质量却高于传统工艺的酿造酒。     

Orosensory-directed identification of astringent mouthfeel and bitter-tasting compounds in red wine

Application of sequential solvent extraction, followed by HPLC combined with the taste dilution analysis, enabled the localization of the most intense velvety astringent, drying, and puckering astringent, as well as bitter-tasting, compounds in red wine, respectively. Isolation of the taste components involving gel adsorption chromatography, ultrafiltration, and synthesis revealed the identification of 26 sensory-active nonvolatiles, among which several hydroxybenzoic acids, hydroxycinnamic acids, flavon-3-ol glycosides, and dihydroflavon-3-ol rhamnosides as well as a structurally undefined polymeric fraction (>5 kDa) were identified as the key astringent components. In contradiction to literature suggestions, flavan-3-ols were found to be not of major importance for astringency and bitter taste, respectively. Surprisingly, a series of hydroxybenzoic acid ethyl esters and hydroxycinnamic acid ethyl esters were identified as bitter compounds in wine. Taste qualities and taste threshold concentrations of the individual wine components were determined by means of a three-alternative forced-choice test and the half-mouth test, respectively.     

Effect of macerating enzymes on red wine aroma at laboratory scale: exogenous addition or expression by transgenic wine yeasts.

The effects of a Trichoderma longibrachiatum endoglucanase and an Aspergillus nidulans endoxylanase on the concentration of free and bound volatiles, color, and phenolics during maceration in red wine vinification has been studied. Two different approaches have been considered for the utilization of these enzymes: (i) direct addition of the enzymes to must and (ii) inoculation of must with recombinant wine yeasts overexpressing these activities. An experimental design based on a Taguchi orthogonal array was carried out in order to evaluate the effects of the enzymatic treatments. The data show that these fungal activities are able to increase the concentrations of free and glycosidically bound flavor compounds, color, and phenolics to similar or greater extents as compared to a commercial pectolytic enzyme preparation. The effects of the two different ways of addition of the enzymes were not always equivalent. These enzymes could be considered to be of potential application in the red wine maceration process.     

河西走廊产区酒球菌酯酶活性对葡萄酒酯类香气物质的影响

试验以2株本土O.oeni GF-2、ZX-1和商业菌株VP41为供试菌株,在模拟酒中动态监测苹果酸-乳酸发酵过程中菌株的C2、C4、C6酯酶活性,分析比较不同初始pH值、乙醇浓度、SO2添加量和发酵温度对菌株产酶规律的影响;通过微酿试验探讨供试菌株对霞多丽干白葡萄酒香气品质的影响.结果表明,在不同pH值条件下,本土O...     

Retronasal transport of aroma compounds

A comparison was made between the amounts of volatiles in the headspace above a solution and the breath volatile content (exhaled from the nose or mouth) after consumption of the same solution. The amounts of volatiles in the breath were lower than those in the headspace, with breath exhaled via the mouth containing, on average, 8-fold more volatiles than breath exhaled via the nose. Dilution of the sample by saliva in-mouth did not appear to be a major factor affecting volatile delivery. Instead, the rate of in vivo equilibration (mass transfer) appeared to be the most significant factor, principally affecting volatile delivery from the solution to the gas phase. Thereafter, gas-phase dilution of the volatile as it passed through the upper airway resulted in a further decrease in volatile concentration. The final factor affecting the volatile concentration exhaled from the nose was absorption of volatiles to the nasal epithelia, which was greatest for those compounds with the lowest air/water partition coefficients.     

Gas chromatographic-olfactometric characterization of aroma compounds in two types of cashew apple nectar

Cashew apple nectar is a secondary product from the production of cashew nuts and possesses an exotic tropical aroma. Aroma volatiles in pasteurized and reconstituted (from concentrate) Brazilian cashew apple nectars were determined using GC-MS and split, time-intensity GC-olfactometry (GC-O)/GC-FID. Methional, (Z)-1,5-octadien-3-one, (Z)-2-nonenal, (E,Z)-2,4-decadienal, (E,E)-2,4-decadienal, beta-damascenone, and delta-decalactone were identified for the first time in cashew apple products. These compounds plus butyric acid, ethyl 3-methylbutyrate, 2-methylbutyric acid, acetic acid, benzaldehyde, homofuraneol, (E)-2-nonenal, gamma-dodecalactone, and an unknown were the most intense aroma volatiles. Thirty-six aroma volatiles were detected in the reconstituted sample and 41 in the pasteurized sample. Thirty-four aroma active components were common to both samples. Ethyl 3-methylbutyrate and 2-methylbutyric acid were character impact compounds of cashew apple (warm, fruity, tropical, sweaty). Using GC-pFPD, 2-methyl-3-furanthiol and bis(2-methyl-3-furyl) disulfide were identified for the first time in cashew apple. Both were aroma active (meaty).     

干红葡萄酒中白黎芦醇的研究

该文系统研究了葡萄果实中白黎芦醇的分布、工艺条件、产地和年份等因素对葡萄酒中白藜芦醇含量影,结果表明葡萄浆果中的白黎芦醇主要分布在果皮,果肉中的含量最低;发酵温度、酵母菌、乳酸菌种类对葡萄酒中白黎芦醇含量有影响;品种及产地、年份所引起的生态条件的差异是引起葡萄酒中白黎芦醇含量差异的主要原因.     

Retention of aroma compounds in starch matrices: competitions between aroma compounds toward amylose and amylopectin

The retention of three aroma compounds-isoamyl acetate, ethyl hexanoate, and linalool--from starch-containing model food matrices was measured by headspace analysis, under equilibrium conditions. We studied systems containing standard or waxy corn starch with one or two aroma compounds. The three studied aroma compounds interact differently: ethyl hexanoate and linalool form complexes with amylose, and isoamyl acetate cannot. However, in systems containing one aroma compound, we observed with both starches a significant retention of the three molecules. These results indicate that amylopectin could play a role in the retention of aroma. In systems containing two aroma compounds in a blend, the retentions measured for isoamyl acetate and for linalool were either equal to or less than those in systems where they were added alone. This phenomenon was attributed to competition between aroma compounds to bind with starch. The retention of aroma compounds blended in starch-based systems gave us additional information which confirmed that interactions occur not only with amylose but also with amylopectin.     

Characterization of the aroma of a wine from maccabeo. Key role played by compounds with low odor activity values

An extract from a dry young wine from Maccabeo was studied by aroma extract dilution analysis (AEDA), quantitative gas chromatography, and different sensory studies. In a first study, 53 different aroma compounds were quantified and used to prepare aroma models. 2-Methyl-3-furanthiol (FD = 16) and 4-methyl-4-mercaptopentan-2-one (FD = 2), could not be quantified and were not included in those models, which were not very similar to the original wine. Omission tests did not show the existence of impact compounds. In another set of experiments, selected aroma chemicals were added to the original wine, but in only in two cases (isoamyl acetate and gamma-nonalactone) was a positive effect noted, on banana and citric notes, respectively. After these discouraging results, 4-methyl-4-mercaptopentan-2-one and 2-methyl-3-furanthiol were quantified and included in the models. The concentration of the former was as low as 5 ng x L(-)(1) (odor threshold = 0.8 ng x L(-)(1)); however, its inclusion in the synthetic mixture had a significant effect, making it very close to the original wine. Its role was confirmed by omission tests. Results are briefly discussed.     

干白葡萄酒增香酿造工艺参数优化

试验以一种酿酒葡萄为原料,利用顶空固相微萃取/气相色谱-质谱联用技术(HS-SPME/GC-MS)检测了不同可同化氮含量(200、300、400 mg/L)、酵母多糖(150、250、350 mg/L)、发酵温度(14、18、22℃)、初始pH值(3.3、3.5、3.7)和SO2添加量(40、70、100 mg/L)处理发酵酒样中的挥发性香气化合物,探讨了复合酿造因子对贵人香干白葡萄酒主要香气物质含量的影响关系。结果表明,300 mg/L的可同化氮有利于高级醇、酯类、单萜化合物的积累;酵母多糖添加量为250 mg/L时,单萜化合物质量分数达到最大值(198.54μg/L);发酵温度从14℃升高到22℃时,高级醇含量显著升高,酯类和单萜含量显著降低;提高葡萄汁初始pH有利于单萜化合物的积累,不利于高级醇、酯类的生成;添加70 mg/L的SO2时,单萜化合物质量分数最高(181.73μg/L)。正交试验极差分析表明,发酵温度和SO2添加量对高级醇含量影响较大;发酵温度与可同化氮对酯类香气物质含量的影响较大,酵母多糖和pH值对单萜类香气物质含量影响较大。各处理组间的聚类分析可知,可同化氮和酵母多糖对主要香气化合物的影响关联度较高、葡萄汁初始pH值和SO2添加量关联度较高。较低的发酵温度有利于酒样中香叶醇、异戊醇、苯乙醇、辛酸乙酯的生成,添加中等浓度的可同化氮和酵母多糖可促进乙酸异戊酯、乙酸己酯和己酸乙酯的合成,较高的初始pH值有利于芳樟醇、香茅醇和香叶醇的积累。综合分析,发酵温度18℃、初始pH值3.5、70 mg/L SO2、300 mg/L可同化氮、250 mg/L酵母多糖酿造贵人香干白葡萄酒,可有效促进酒样中主要香气化合物的合成释放。     

Antiradical properties of red wine portisins

The free radical chemistry of two polyphenolic pigments from red wine, belonging to the family of portisins, has been investigated after reaction with O(2)(?-) radicals using electron paramagnetic resonance (EPR) spectroscopy. Two portisins derived from malvidin-3-glucoside and cyanidin-3-glucoside were used for this study. Stable free radicals were detected with both portisins and correspond to unpaired electrons localized on the B as well as F rings of the portisins. Interpretations were confirmed by comparison with the spectra of free radicals formed by oxidation of the model compounds cyanidin-3-glucoside, malvidin-3-glucoside, and catechin. These results concur with previous work reporting the higher antiradical properties of these pigments compared to their anthocyanin precursors.     

红葡萄酒颜色研究进展

红葡萄酒色泽是影响葡萄酒感官质量的重要指标之一,如何稳定红葡萄酒的色泽一直是葡萄酒酿造工艺技术关注的的焦点;该文综述了红葡萄酒中花色苷的种类以及影响红葡萄酒色泽的主要因素,包括栽培因素、葡萄酒发酵条件、贮藏陈酿过程中的环境因素和外源添加物应用等.并对我国红葡萄酒生产中存在的问题进行了分析.     

Effect of antioxidant protection of must on volatile compounds and aroma shelf life of Falanghina (Vitis vinifera L.) wine

Two vinification methods involving different degrees of antioxidant protection of Falanghina must during prefermentative steps, and referred as HAMP (high antioxidant must protection) and LAMP (low antioxidant must protection), were compared in terms of fermentation performances of four different yeast strains, composition of the volatile fraction of wines at the end of alcoholic fermentation, and shelf life of wines during storage. The use of HAMP technology resulted in wines with lower volatile acidity and higher concentrations of medium-chain fatty acid ethyl esters, acetates, and volatile fatty acids. For two of the four strains a lower concentration of isoamyl alcohol was also observed. HAMP wines also revealed increased shelf life because of the higher concentration of odor active esters at the end of storage and better preservation of varietal aromas.     

Possible mechanism for involvement of cysteine in aroma production in wine

Under conditions close to those of wine, that is, low pH, aqueous medium, and low temperatures, this work describes N-(2-sulfanylethyl)-2-oxopropanamide (1), a new intermediate in the formation of 2-acetylthiazole from methylglyoxal and cysteine. 1 was characterized by MS, derivatization MS, and (1)H and (13)C NMR and was synthesized from 2-sulfanylethanamine and ethyl pyruvate. A formation pathway for 2-acetylthiazole from methylglyoxal and cysteine is proposed, in which 1 is a new intermediate in Maillard-type reactions in systems under mild conditions.     

Competitive binding of aroma compounds by beta-cyclodextrin.

Retention of six aroma compounds has been studied after dehydration of ternary mixtures of aroma water and beta-cyclodextrin. A maximal retention of a mole of aroma per mole of beta-cyclodextrin has been observed for five of the aroma compounds, whereas retention of benzyl alcohol can be twice as high. Retention of a mixture of aroma compounds has also been studied. It has been noted that when volatile compounds compete for the same binding sites on beta-cyclodextrin, ethyl hexanoate, 2-methylbutyric acid, and benzyl alcohol are, respectively, better retained than ethyl propionate, hexanoic acid, and hexanol. Preferential retention observed with esters can be simply explained by their difference of physicochemical properties, but for the acids and alcohols a study at the molecular scale has been necessary. The better retention of 2-methylbutyric acid can be explained by differences in the nature of interaction between the acids and their carrier. At least selectivity of retention noted for the alcohol could be due to a difference in the location of the guest and also a difference in the number of aroma molecules that can be bound per polysaccharide molecule.