Modulation of aroma and chemical composition of Albariño semi-synthetic wines by non-wine Saccharomyces yeasts and bottle aging.

Saccharomyces yeasts from different origins and species fermented in a semi-synthetic must containing aroma precursor of cv. Albariño and polyfunctional mercaptans precursors. The resulting wines were subjected to accelerate anoxic aging. Afterward, aroma profiles were analyzed by distinct gas chromatography methodologies. Cryotolerant strains showed better fermentation performances with significant differences in volatile and non-volatile fermentation products than Saccharomyces cerevisiae (S. cerevisiae). We suggested that the highest levels γ-butyrolactone and diethyl succinate in Saccharomyces uvarum (S. uvarum) strains, together with their substantial succinic acid yields, could be related to greater flux through the GABA shunt. These strains also had the highest production of ß-phenylethyl acetate, geraniol, and branched-chain ethyl esters. The latter compounds were highly increased by aging, while acetates and some terpenes decreased. S. kudriavzevii strains showed a remarkable ability to release polyfunctional mercaptans, with SK1 strain yielding up to 47-fold and 8-fold more 4-methyl-4-mercaptopentan-2-one (4MMP) than S. cerevisiae and S. uvarum strains, respectively. The wild S. cerevisiae beer isolate showed a particular aroma profile due to the highest production of ethyl 4-methylvalerate (lactic and fruity notes), γ-octalactone (coconut), and furfurylthiol (roasted coffee). The latter compound is possibly produced from the pentose phosphate pathway (PPP). Since erythritol, another PPP intermediate was largely produced by this strain.

Ultrasonic modification of pectin for enhanced 2-furfurylthiol encapsulation: process optimization and mechanisms.

BACKGROUND: Pectin is an intriguing polymer, which is usually regarded as a byproduct from agricultural and biological processes. In previous studies, ultrasound treatment has been explored to improve the functionality of pectin but most of that work focused on aspects of molecular structure and the chemical properties of pectin. In this study, we utilized ultrasound treatment to modify the physiochemical properties of pectin. Using ultrasound treatment, we evaluated the emulsifying capability of pectin as a function of ultrasonic time and power density, using a response surface approach. A very potent yet unstable coffee-like aroma compound, 2-furfurylthiol, was also used for comparing the encapsulation feasibility of emulsion made with original pectin and ultrasound-treated pectin. RESULTS: Our results showed that the particle size of pectin was highly correlated with power density and ultrasound time. Approximately 370 nm of pectin particle size could be reached at a power density of 1.06 W mL-1 for 40 min. Ultrasound treatment increased emulsion droplet size but significantly improved emulsifying capacities, such as centrifugal stability and surface loading, although it was highly dependent upon the ultrasound treatment condition. When used as the encapsulation wall material, the ultrasound-modified pectin had significantly enhanced performance compared with the original, in terms of flavor retention over time at 45 °C and 65 °C. CONCLUSION: Ultrasound treatment was able to modify the physiochemical properties of pectin, which thus improved emulsification stability and encapsulation feasibility by forming a thicker layer at the oil / water interface to protect the core materials. © 2019 Society of Chemical Industry.

Roles of sulfur-containing compounds in fermented beverages with 2-furfurylthiol as a case example.

Aroma is a critical component of the flavor and quality of beverages. Among the volatile chemicals responsible for fragrance perception, sulfur compounds are unique odorants due to their extremely low odor threshold. Although trace amounts of sulfur compounds can enhance the flavor profile of beverages, they can lead to off-odors. Sulfur compounds can be formed via Maillard reaction and microbial metabolism, imparting coffee aroma and altering the flavor of beverages. In order to increase the understanding of sulfur compounds in the field of food flavor, 2-furfurylthiol (FFT) was chosen as a representative to discuss the current status of their generation, sensory impact, enrichment, analytical methods, formation mechanisms, aroma deterioration, and aroma regulation. FFT is comprehensively reviewed, and the main beverages of interest are typically baijiu, beer, wine, and coffee. Challenges and recommendations for FFT are also discussed, including analytical methods and mechanisms of formation, interactions between FFT and other compounds, and the development of specific materials to extend the duration of aroma after release.

Comprehensive binding analysis of glycated myosin with furan derivatives via glucose by means of multi-spectroscopy techniques and molecular docking simulation.

Myosin is an ideal binding receptor for aroma compounds and its functional properties are easily affected by glucose. The study comprehensively clarified the effects of glucose glycation-induced structural modifications of myosin on its binding ability with furan derivatives, including 2-methylfuran, 2-furfural, and 2-furfurylthiol. The results demonstrated that the binding levels of furan derivatives were obviously affected by the glycation levels of myosin due to the changes of myosin structure and surface. The increased glycation levels caused the unfolding of myosin structure and accelerated the aggregation, as were exhibited by the data of zeta potential, particle size, microstructure, and secondary structure. The glycated myosin with wrinkled surfaces favored the significant increase of hydrophobic interactions (31.59-69.50 µg), the more exposure of amino acid residues (3459-6048), the formation of free sulfhydryl groups (16.37-20.58 mmol/104g) and hydrogen bonds. These key (non)covalent linkages accounted for the generation of glycated myosin-odorants complex, including 2-furfurylthiol (29.17-47.87 %), thus enhancing the resultant binding ability as evidenced by the free furan derivatives concentrations, fluorescence quenching and molecular docking simulation analysis. The glycated myosin for 8 h bound highest concentrations of furan derivatives. The results will provide comprehensive data on the retention of aroma compounds in meat products.

A review on flavor of Baijiu and other world-renowned distilled liquors.

The flavor characteristics of distilled liquors significantly affect consumer acceptance and adoption. Therefore, odorants that contribute to sensory properties have received more attention. The odorants depend on the operating parameters, such as raw materials and ingredients, manufacturing process and maturing circumstances. This review summarized the odorants in the Baijiu and other world-renowned distilled liquors. Especially, the contribution of the odorants to the dominant aroma attributes is given more attention. The variations in the constituents and contents of odorants among the liquors are discussed comprehensively. In general, further research is still needed on the interaction mechanism between the odorants and sensory properties of distilled liquors.

Increasing 2-furfurylthiol content in Chinese sesame-flavored Baijiu via inoculating the producer of precursor l-cysteine in Baijiu fermentation.

2-Furfurylthiol was an important contributor to the flavor of traditional fermented foods including Baijiu. It is essential to increase 2-furfurylthiol concentration to improve the quality of Baijiu. This study aimed to enrich the content of 2-furfurylthiol in Chinese sesame-flavored Baijiu via two strains we isolated from Baijiu fermentation, Bacillus subtilis LBM 10019 and Bacillus vallismortis LBM 10020, which could respectively produce 56.31 mg/L and 42.81 mg/L l-cysteine, the precursor of 2-furfurylthiol, in sorghum extract. After inoculation of these two strains, the maximal relative abundance of Bacillus increased from 7.48% to 40.38%, the final content of l-cysteine increased by 101.44% in Baijiu fermentation. Moreover, the concentration of 2-furfurylthiol increased by 89.15% in the production. This work provides a novel strategy to improve the quality of Chinese sesame-flavored Baijiu.

Enhancement of coffee brew aroma through control of the aroma staling pathway of 2-furfurylthiol.

During storage of coffee, the key aroma 2-furfurylthiol becomes less active, the mechanisms of this loss and ways to mitigate it were investigated. Aroma profiles were analyzed using GC-MS and sensory properties were evaluated by Quantitative Descriptive Analysis. Quinones, as the oxidation products of hydroxydroquinone, was found to actively bind 2-furfurylthiol, which accounted for the loss of 2-furfurylthiol. To mitigate this loss, ingredients were screened for their ability to prevent 2-furfurylthiol from loss. Cysteine had the highest 2-furfurylthiol releasing efficiency and ascorbic acid was also selected due to its 2-furfurylthiol releasing ability in Fenton reaction system. Concentrations were optimized and the addition of 0.045 g/L cysteine and 0.05 g/L ascorbic acid directly protected aroma during storage, these included 2-furfurylthiol, dimethyltrisulfide, methyl furfuryl disulfide, 4-ethylguaiacol and 4-vinylguaiacol. Ultimately, sensory testing showed a direct enhancement in nutty, sulfurous and roasted aroma attributes, an increase in flavour intensity and preference over shelf life.

Optimization of the Maillard reaction of xylose with cysteine for modulating aroma compound formation in fermented tilapia fish head hydrolysate using response surface methodology.

Aroma defects limit the application of fish protein hydrolysates as flavourings. This study aimed to develop a flavour concentrate from fermented tilapia fish head hydrolysate bymaximising the Maillard reaction production of meaty and roasted aroma associated compounds. We studied the optimal conditions of the Maillard reaction of xylose with cysteine to form meat-like odorants using response surface methodology. A 3-factored and 3-leveled Box Behnken design was employed, where the independent variables were cysteine concentration (A, w/v, %), heating temperature (B, °C) and heating time (C, min). 2-Methyl-3-furanthiol and 2-furfurylthiol were used as response factors. The optimal conditions were obtained as follows: A, 0.80%; B, 183.80 °C; C, 89.34 min. Compared with the controls, Maillard reaction products enriched the meaty and roasted aroma associated compounds in the treated hydrolysate. In conclusion, the treated tilapia fish head hydrolysate may be used as a base in development of new fish-based flavourings.

Aroma binding and stability in brewed coffee: A case study of 2-furfurylthiol.

The aroma stability of fresh coffee brew was investigated during storage over 60 min, there was a substantial reduction in available 2-furfurylthiol (2-FFT) (84%), methanethiol (72%), 3-methyl-1H-pyrole (68%) and an increase of 2-pentylfuran (65%). It is proposed that 2-FFT was reduced through reversible chemical binding and irreversible losses. Bound 2-FFT was released after cysteine addition, thereby demonstrating that a reversible binding reaction was the dominant mechanism of 2-FFT loss in natural coffee brew. The reduction in available 2-FFT was investigated at different pH and temperatures. At high pH, the reversible binding of 2-FFT was shown to protect 2-FFT from irreversible losses, while irreversible losses led to the reduction of total 2-FFT at low pH. A model reaction system was developed and a potential conjugate, hydroxyhydroquinone, was reacted with 2-FFT. Hydroxyhydroquinone also showed 2-FFT was released after cysteine addition at high pH.

Characterization of key aroma-active sulfur-containing compounds in Chinese Laobaigan Baijiu by gas chromatography-olfactometry and comprehensive two-dimensional gas chromatography coupled with sulfur chemiluminescence detection.

Volatile sulfur-containing compounds (VSCs) often exist at extremely low concentrations, making them difficult to be determined. The VSCs in Laobaigan (LBG) Baijiu were analyzed by headspace solid-phase microextraction (HS-SPME) coupled with GC × GC-SCD, by which 12 VSCs were identified. Among the 65 odor-active compounds that were determined by GC-O with the aid of aroma extract dilution analysis (AEDA), benzenemethanethiol and 2-methyl-3-furanthiol were found to possess the highest FD values of 6561. The limits of detection (LODs) of the identified VSCs determined by GC × GC-SCD were found to be extremely low at 0.05-1.53 ng/L, with their analytical recoveries from 85% to 116%. The VSCs in the LBG samples were determined in a range of concentrations from 0.77 ±â€¯0.02 µg/L to 60.04 ±â€¯2.32 µg/L. Benzenemethanethiol, dimethyl trisulfide, 2-methyl-3-furanthiol and 2-furfurylthiol exhibited odor activity values (OAVs) > 100 and significantly contributed to the overall aroma of LBG Baijiu.

Chemosensate-Induced Modulation of the Salivary Proteome and Metabolome Alters the Sensory Perception of Salt Taste and Odor-Active Thiols.

Oral stimulation with chemosensates was found to trigger changes in the composition of the salivary proteome and metabolome, which translate into a functional modulation of odor and taste perception. Orosensory intervention with 6-gingerol induced a significant increase in the abundance of salivary sulfhydryl oxidase 1, which was found to catalyze the oxidative decline of odor-active 2-furfurylthiol, thus resulting in a decrease in the odorant levels in exhaled breath, as shown by PTR-MS, and a reduction of the perceived sulfury after-smell. Therefore, sulfhydryl oxidase 1 may be considered as a component of a molecular network triggering oral cleansing mechanisms after food ingestion. Moreover, oral stimulation with citric acid, followed by targeted metabolomics, was found to induce a strong increase in salivary concentrations of minerals and, in particular, sodium ions, whereas the other metabolites were rather unaffected. Because of the elevated basal levels of salivary sodium after citric acid stimulation, NaCl test stimuli were perceived as significantly less salty, most likely due to the decreased sensory contrast. This indicates the modulation of the salivary proteome and metabolome to be a major perireceptor event in fine-tuning odor and taste sensitivity.

Generation of 2-Furfurylthiol by Carbon-Sulfur Lyase from the Baijiu Yeast Saccharomyces cerevisiae G20.

2-Furfurylthiol is the representative aroma compound of Chinese sesame-flavored baijiu. Previous studies demonstrated that baijiu yeasts could generate 2-furfurylthiol using furfural and l-cysteine as precursors and that the Saccharomyces cerevisiae genes STR3 and CYS3 are closely related to 2-furfurylthiol biosynthesis. To confirm the mechanism of the STR3- and CYS3-gene products on 2-furfurylthiol biosynthesis, their encoded proteins were purified, and we confirmed their activities as carbon-sulfur lyases. Str3p and Cys3p were able to cleave the cysteine-furfural conjugate to release 2-furfurylthiol. Moreover, the characterization of the enzymatic properties of the purified proteins shows good thermal stabilities and wide pH tolerances, which enable their strong potential for various applications. These data provide direct evidence that yeast Str3p and Cys3p release 2-furfurylthiol in vitro, which can be applied to improve baijiu flavor.

Structure-Odor Correlations in Homologous Series of Mercapto Furans and Mercapto Thiophenes Synthesized by Changing the Structural Motifs of the Key Coffee Odorant Furan-2-ylmethanethiol.

Furan-2-ylmethanethiol (2-furfurylthiol; 2-FFT, 1) is long-known as a key odorant in roast and ground coffee and was also previously identified in a wide range of thermally treated foods such as meat, bread, and roasted sesame seeds. Its unique coffee-like odor quality elicited at very low concentrations, and the fact that only a very few compounds showing a similar structure have previously been described in foods make 1 a suitable candidate for structure-odor activity studies. To gain insight into the structural features needed to evoke a coffee-like odor at low concentrations, 46 heterocyclic mercaptans and thio ethers were synthesized, 32 of them for the first time, and their odor qualities and odor thresholds were determined. A movement of the mercapto group to the 3-position kept the coffee-like aroma but led to an increase in odor threshold. A separation of the thiol group from the furan ring by an elongation of the carbon side chain caused a loss of the coffee-like odor and also led to an increase in odor thresholds, especially for ω-(furan-2-yl)alkane-1-thiols with six or seven carbon atoms in the side chain. A displacement of the furan ring by a thiophene ring had no significant influence on the odor properties of most of the compounds studied, but the newly synthesized longer-chain 1-(furan-2-yl)- and 1-(thiophene-2-yl)alkane-1-thiols elicited interesting passion fruit-like scents. In total, only 4 out of the 46 compounds also showed a coffee-like odor quality like 1, but none showed a lower odor threshold. Besides the odor attributes, also retention indices, mass spectra, and NMR data of the synthesized compounds were elaborated, which are helpful in possible future identification of these compounds in trace levels in foods or other materials.

Steam pressure treatment of defective Coffea canephora beans improves the volatile profile and sensory acceptance of roasted coffee blends.

Between 15 and 20% of Brazilian coffee production corresponds to defective beans (PVA), which decreases the quality of the coffee brew. Steam treatment has been reported as an alternative to improve the volatile profile and cup quality of coffee. The aim of this study was to propose a steam treatment of defective Coffea canephora beans to improve the volatile profile of the roasted coffee. The sensory impacts of adding steamed coffee (SC) in Coffea arabica blends were evaluated. The steam treatments studied modified the volatile profile of roasted SCs, increasing the contents of acetoin, benzyl alcohol, maltol, 2,6-dimethylpyrazine, 2-furfurylthiol, and 5-methylfurfural and decreasing the contents of 4-ethylguaiacol, isovaleric acid, methional, 2,3-diethyl-5-methylpyrazine, and 3-methoxy-3-methylpyrazine. Among the evaluated parameters, the best condition to maximized the content of the volatiles with a potential positive impact and minimize those with a potential negative impact was 5bar/16min (SC 5). The thresholds of consumer rejection and of detection indicate that up to 30% SC 5 can be added to a high cup quality Coffea arabica coffee without perception or rejection of the coffee brew. A blend of 30% of SC 5 and 70% of Coffea arabica was well accepted.

STR3 and CYS3 Contribute to 2-Furfurylthiol Biosynthesis in Chinese Sesame-Flavored Baijiu Yeast.

2-Furfurylthiol is an important aroma compound with characteristic sesame flavor. It was recently identified as the representative aroma compound of Chinese sesame-flavored Baijiu. But its formation mechanism is unclear. In this study, the dominant yeast species Saccharomyces cerevisiae, Pichia kudriavzevii, and Wickerhamomyces anomalus were isolated from samples of Chinese sesame-flavored fermentation and were screened for the capacity of 2-furfurylthiol biosynthesis. Some isolates were found to be capable of generating 2-furfurylthiol using furfural and l-cysteine as precursors, among which S. cerevisiae G20 exhibited the strongest capacity with a yield of 3.03 mg/L. Furthermore, the genes STR3 and CYS3 from S. cerevisiae were cloned and overexpressed in the reference strain S. cerevisiae S288c and the isolate strain G20, respectively, which resulted in a significant increase in 2-furfurylthiol release in the two strains. Moreover, inactivation of STR3 gene in S288c and G20 led to obvious reduction in 2-furfurylthiol production, demonstrating that STR3 got involved in 2-furfurylthiol biosynthesis in S. cerevisiae. It is the first time that the yeast isolates with high capacity of 2-furfurylthiol biosynthesis were found during Chinese sesame-flavored Baijiu fermentation and confirmed that the genes STR3 and CYS3 were closely relevant to 2-furfurylthiol biosynthesis.

Characterization of the Typical Potent Odorants in Chinese Roasted Sesame-like Flavor Type Liquor by Headspace Solid Phase Microextraction-Aroma Extract Dilution Analysis, with Special Emphasis on Sulfur-Containing Odorants.

The aroma profile of Chinese roasted sesame-like flavor type liquor was investigated by means of headspace solid phase microextraction-aroma extract dilution analysis (HS-SPME-AEDA). Sixty-three odor-active regions were detected by HS-SPME-AEDA with flavor dilution (FD) factors >5, and 58 of these were further identified. Among them, ethyl hexanoate, 2-furfurylthiol, dimethyl trisulfide, 3-methylbutanal, ethyl butanoate, ethyl 2-methylbutanoate, ethyl pentanoate, and ethyl 4-methylpentanoate appeared with the highest FD factors. In particular, eight sulfur-containing odorants were identified to be potentially important to roasted sesame-like flavor type liquor. The concentration of these odor-active compounds was further quantitated by combination of four different quantitative measurements, and 36 odorants had concentrations higher than their corresponding odor thresholds. On the basis of the odor activity values (OAVs), 2-furfurylthiol (OAV 1182), dimethyl trisulfide (OAV 220), ß-damascenone (OAV 116), and methional (OAV 99) could be responsible for the unique aroma of roasted sesame-like flavor type liquor. An aroma recombination model prepared by mixing 36 aroma compounds with OAVs >1 showed a good similarity to the aroma of the original roasted sesame-like flavor type liquor. For the first time, 2-furfurylthiol was determined to be a typical potent odorant in roasted sesame-like flavor type liquor by omission study.

Changes in analytical and volatile compositions of red wines induced by pre-fermentation heat treatment of grapes.

Experiments were carried out on Grenache, Carignan and Fer grapes in order to characterize the changes in nitrogen content of the musts, conventional enological parameters and aroma compounds of the wines induced by pre-fermentation heating of the grapes followed by alcoholic fermentation in liquid phase or in solid phase. In comparison to a standard vinification, we showed that a two-hour heat treatment at 70 °C induced a significant loss in several grape-derived aroma compounds (terpenols, norisoprenoids and some phenols) associated with an increase in α-terpineol, guaiacol and 2,6-dimethoxyphenol, which suggests thermal degradation. A significant increase in most of the ethyl esters, in acetates and in fatty acids were observed in wines fermented in liquid phase, together with a decrease in fusel alcohols. The substantial modification in the amino acid composition of the must seems to be a crucial element for the understanding of these changes.