Identification of Two New Taste-Active Compounds in Oak Wood: Structural Elucidation of Potential ß-Methyl-γ-octalactone Precursors and Quantification in Spirits.

Barrel aging is a crucial stage that influences the taste of wines and spirits, particularly increasing their sweetness and bitterness. This increase is caused by nonvolatile compounds released from oak wood. To search for such molecules, we performed a taste-guided inductive fractionation protocol using several analytical techniques. By using HRMS and NMR, two new galloylated derivatives were elucidated. Their enzymatic hydrolysis revealed the formation of ß-methyl-γ-octalactone, indicating that they are potential precursors. The taste properties of these isomers revealed a sweet and bitter taste for P-WL-1 and P-WL-2, respectively. An LC-HRMS quantification method was performed to evaluate the influence of aging parameters such as botanical origin and toasting process on their concentrations. Several spirits were also analyzed to confirm their presence in this matrix. These results improve the understanding of the molecular markers responsible for the taste of beverages.

Effect of fermentation containers on the taste characteristics and microbiota succession of soy sauce.

Modernization of the traditional fermentation industry has been a major trend recently, such as the upgrading of fermentation containers. This study investigated the taste differences and their material basis of soy sauce fermented in tank and pond (SSFT and SSFP), and further explore the key influencing factors of taste. The intensities of umami, kokumi and sour taste in SSFT were weaker than SSFP, which were associated with 9 basic taste-active compounds, including acetic acid, lactic acid, propanedioic acid, citric acid, glutamic acid, alanine, tyrosine, d-galactose and erythritol. Moreover, 270 peptides and amino acid derivatives were potential compounds for taste difference, of which 78 % were more abundant in SSFP. Five bacterial genera (Kocuria, Tetragenococcus, Pediococcus, Staphylococcus, Weissella) and 4 fungal genera (Wickerhamiella, Millerozyma, Candida, Zygosaccharomyces) may be the functional core microbe for flavor differences in SSFT and SSFP. This study will provide theoretical value for quality improvement in the modern large-scale production of soy sauce.

A review on natural sweeteners, sweet taste modulators and bitter masking compounds: structure-activity strategies for the discovery of novel taste molecules.

Growing demand for the tasty and healthy food has driven the development of low-calorie sweeteners, sweet taste modulators, and bitter masking compounds originated from natural sources. With the discovery of human taste receptors, increasing numbers of sweet taste modulators have been identified through human taste response and molecular docking techniques. However, the discovery of novel taste-active molecules in nature can be accelerated by using advanced spectrometry technologies based on structure-activity relationships (SARs). SARs explain why structurally similar compounds can elicit similar taste qualities. Given the characterization of structural information from reported data, strategies employing SAR techniques to find structurally similar compounds become an innovative approach to expand knowledge of sweeteners. This review aims to summarize the structural patterns of known natural non-nutritive sweeteners, sweet taste enhancers, and bitter masking compounds. Innovative SAR-based approaches to explore sweetener derivatives are also discussed. Most sweet-tasting flavonoids belong to either the flavanonols or the dihydrochalcones and known bitter masking molecules are flavanones. Based on SAR findings that structural similarities are related to the sensory properties, innovative methodologies described in this paper can be applied to screen and discover the derivatives of taste-active compounds or potential taste modulators.

Regulating effects of low salt dry-curing pre-treatment on microbiota, biochemical changes and flavour precursors of grass carp (Ctenopharyngodon idella) fillets during storage at 4 °C.

Low salt dry-curing (LSD), as a healthier pre-treatment for the preservation of fishery products, is a potential technique substitute for excessively salty curing. The regulatory effects of 2 % and 3 % LSD on the quality evolution through an intrinsic correlation between microbiota succession and flavour precursors of refrigerated grass carp fillets were investigated in this study. The results showed that the LSD pre-treatment was effective in promoting proteolysis, free amino acid and fatty acid metabolism with the microbiota succession and quality evolution. Compared with unpre-treated samples, the 3 % LSD pre-treatment effectively extended the shelf life by 10 days within the acceptable quality attributes. Not only did the LSD pre-treatment lead to catalytic microbiota succession and inhibitive spoilage substance production but it also improved the flavour precursors, which are taste-active amino acids and polyunsaturated fatty acids (PUFAs). Moreover, considerable correlations between quality attributes, taste-active amino acids, PUFAs and microbiota were obtained.

Evaluation of the differences between low-salt solid-state fermented soy sauce and high-salt diluted-state fermented soy sauce in China: from taste-active compounds and aroma-active compounds to sensory characteristics.

BACKGROUND: The present study aimed to determine the components related to sensory properties in soy sauce and to characterize the differences between low-salt solid-state fermented soy sauce (LSFSS) and high-salt diluted-state fermented soy sauce (HDFSS). The taste and aroma active components of 18 commercially available soy sauces (eight types of LSFSS and 10 types of HDFSS) were characterized. The relationship between these compounds, soy sauce samples, and sensory properties was modeled by partial least squares regression. RESULTS: The analysis showed that the 11 taste-active components, including glutamic acid, glycine, alanine, threonine, malic acid, citric acid, tartaric acid, acetic acid, lactic acid, reducing sugar and salt, contributed greatly to the taste of soy sauce. In addition, umami, saltiness and sweetness are the characteristic tastes of HDFSS, whereas sourness and bitterness were the characteristic tastes of LSFSS. At the same time, seven aroma-active compounds, namely 4-ethyl-2-methoxyphenol, ethanol, 3-methyl-1-butanol, ethyl acetate, 2-phenethyl alcohol, 3-methyl thiopropanol and 2-ethyl-4-hydroxy-5-methylfuran-3-one, played a decisive role in the flavor of soy sauce. In addition, HDFSS presented the aroma attributes of smoky, alcoholic, floral, fruity and caramel-like, whereas LSFSS mainly presented sour and malty aroma attributes. CONCLUSION: The present study reveals new insight into the relationship between the chemical composition and sensory characteristics of soy sauce, which is of great significance for developing an objective measurement system and providing a theoretical basis to improve the sensory quality of soy sauce. © 2023 Society of Chemical Industry.

Estimating the sensory-associated metabolites profiling of matcha based on PDO attributes as elucidated by NIRS and MS approaches.

Matcha has been globally valued by consumers for its distinctive fragrance and flavor since ancient times. Currently, the protected designation of origin (PDO) certified matcha, characterized by unique sensory attributes, has garnered renewed interest from consumers and the industry. Given the challenges associated with assessing sensory perceptions, the origin of PDO-certified matcha samples from Guizhou was determined using NIRS and LC-MS platforms. Notably, the accuracy of our established attribute models, based on informative wavelengths selected by the CARS-PLS method, exceeds 0.9 for five sensory attributes, particularly the particle homogeneity attribute (with a validation correlation coefficient of 0.9668). Moreover, an LC-MS method was utilized to analyze non-target matcha metabolites to identify the primary flavor compounds associated with each flavor attribute and to pinpoint the key constituents responsible for variations in grade and flavor intensity. Additionally, high three-way intercorrelations between descriptive sensory attributes, metabolites, and the selected informative wavelengths were observed through network analysis, with correlation coefficients calculated to quantify these relationships. In this research, the integration of matcha chemical composition and sensory panel data was utilized to develop predictive models for assessing the flavor profile of matcha based on its chemical properties.

Changes in extractive components and bacterial flora in live mussels Mytilus galloprovincialis during storage at different temperatures.

To estimate the quality of mussels during storage, the mortality, succinate dehydrogenase (SDH) activity, extractive components, viable bacterial count (VBC), and bacterial flora of live mussels were investigated. The hierarchical cluster analysis, based on extractive components and VBC, taste active value (TAV), and equivalent umami concentration (EUC), suggested that metabolite composition, bacterial, and taste changing patterns of samples stored at 5 and 10°C differed from those stored at 0°C. The mortality of mussels stored at 5 and 10°C was lower than those at 0°C. The gills of live mussels stored at 0°C for more than 7 days exhibited significantly lower SDH activity than those stored at 5 and 10°C. There was no significant difference in EUC among the samples stored at different temperatures, but a significantly higher TAV of Ala and succinic acid was observed in live mussels after 12 days of storage at 5 and 10°C than in those stored at 0°C. Next-generation sequencing analysis showed that samples stored at 5 and 10°C lost bacterial diversity, and their bacterial flora changed compared to that before storage. Considering these results, the most suitable storage condition to maintain high quality for live mussels is 5°C for less than 7 days.

Characterization of non-volatile and volatile flavor profiles of Coregonus peled meat cooked by different methods.

This study investigated the effects of different cooking methods on non-volatile flavor (free amino acids, 5'-nucleotides, and organic acids, etc.) of Coregonus peled meat. The volatile flavor characteristics were also analyzed by electric nose and gas chromatography-ion migration spectrometry (GC-IMS). The results indicated that the content of flavor substances in C. peled meat varied significantly. The electronic tongue results indicated that the richness and umami aftertaste of roasting were significantly greater. The content of sweet free amino acids, 5'-nucleotides, and organic acids was also higher in roasting group. Electronic nose principal component analysis can distinguish C. peled meat cooked (the first two components accounted for 98.50% and 0.97%, respectively). A total of 36 volatile flavor compounds were identified among different groups, including 16 aldehydes, 7 olefine aldehydes, 6 alcohols, 4 ketones, and 3 furans. In general, roasting was recommended and gave more flavor substances in C. peled meat.

Study on the taste active compounds in Douchi using metabolomics method.

Douchi is a traditional famous seasoning in China. This study adopted electronic tongue and metabolomics to analyze the taste characteristics and taste active compounds of 12 samples from three most famous types of Douchi (Liuyang Douchi, Yangjiang Douchi, Yongchuan Douchi). Thirty-six differential metabolites mainly enriched from the arginine biosynthesis were identified among these Douchis. Umami and bitterness are considered as two taste that bring positive and negative perceptions for Douchi. The succinic acid was found to be responsible for the umami in LY, YJ and YC Douchi, with the TAVs of 2054, 643, 174, respectively, rather than the glutamic acid and aspartic acid. The leucine was identified as the main metabolite for bitterness, with the TAVs of 9, 9, 7 respectively. KEGG enrichment analysis found that the umami, sourness and saltiness might be related to alanine, aspartate and glutamate metabolism and the bitterness might be related to aminoacyl-tRNA biosynthesis pathway.

The effect of aging on beef taste, aroma and texture, and the role of microorganisms: a review.

The present review summarizes the advantages and disadvantages of three different aging methods (traditional dry aging, wet aging in vacuum shrink pack and dry aging in a highly moisture-permeable bag), discusses the effects of aging on beef which focus on the formation of taste-active compounds and aroma-active compounds and texture changes, and speculates the role of microbes. All these three aging methods can improve the aroma, flavor and texture of beef to varying degrees. It is concluded that the improvement in the taste during aging may be attributed to the following three aspects: First, the release of reducing sugars from the transition of glycogen and ATP; Second, the formation of free amino acids (FAAs) and peptides through proteolysis; Third, IMP, GMP, inosine and hypoxanthine which are produced by the degradation of nucleotides. The improvement of aroma is related to the volatile aroma-active components, which are produced by the thermal oxidation/degradation of fatty acids and the Maillard reaction between amino acids and reducing sugars during aging. And the change of texture is mainly owing to the degradation of cytoskeletal myofibrin and collagen with intramural connective tissue in meat by the endogenous proteolysis system. The role of microorganism in aging will be the main direction of further research.

Effects of High Hydrostatic Pressure and Storage Temperature on Fatty Acids and Non-Volatile Taste Active Compounds in Red Claw Crayfish (Cherax quadricarinatus).

The effects of high hydrostatic pressure (treated with 200, 400 and 600 MPa) and storage temperatures (4 °C and −20 °C) on the fatty acids and flavor compounds of red claw crayfish were studied. HHP decreased the PUFA, GMP, IMP and AMP, citric and lactic acids, and PO43− contents, but the FAA, Ca2+ and Cl− contents increased in HHP-treated crayfish compared to untreated crayfish at 0 d. Storage at −20 °C could restrain the fatty acids and flavor contents compared to those stored at 4 °C. The GMP, AMP, citric acid and PO43− contents decreased, and Ca2+ and Cl− contents increased after storage at 4 °C for 15 d (p < 0.05). HHP at 200 and 400 MPa increased EUC on 0 d. No significant changes in EUC were observed after storage at −20 °C for 15 d, significant decreases were noted at 4 °C than the crayfish stored for 0 d (p < 0.05), except for the untreated group. Generally, HHP at 200 or 400 MPa, and storage at −20 °C is beneficial according to the shelling rates and EUC of crayfish.

Comparison of Biochemical Composition and Non-Volatile Taste Active Compounds of Back and Abdominal Muscles in Three Marine Perciform Fishes, Chromileptes altivelis, Epinephelus akaara and Acanthopagrus schlegelii.

Humpback grouper Chromileptes altivelis (HG), red-spotted grouper Epinephelus akaara (RG) and black seabream Acanthopagrus schlegelii (BS) are three popular perciform fishes with an increasingly important farming industry. The prices of BS are much lower than other grouper species; however, the differences in the nutritive values of these three perciform fishes with commercial specifications have not been reported. In this study, the biochemical composition and non-volatile taste active compounds of adult HG, RG and BS were investigated. Moisture contents in BS were significantly higher than in HG and RG (p < 0.05), and relatively lower crude protein contents in BS were observed. Lipid contents of back muscle were lower than that of abdomen muscle in the three fish species. C22:6n-3 (DHA) was the major poly-unsaturated fatty acid (PUFA) in HG and BS, while the main PUFA in RG was C18:2n-6. The total healthy omega-3 fatty acid (Σn-3) profiles in HG were the highest (24.08−24.59%), followed by RG (18.24−19.06%) and BS (13.63−15.91%) (p < 0.05). Glycine was the most abundant free amino acid (FAA) in HG and RG, while lysine was the major FAA in BS. Equivalent umami concentration (EUC) values in BS were the highest, followed by HG and RG (p < 0.05). Lactic acid and PO43− were the major organic acids and inorganic ions, respectively. In conclusion, HG and RG provided more protein and healthy omega-3 fatty acids than BS, while BS had a stronger umami taste according to the EUC values.

Fish proteins as potential precursors of taste-active compounds: an in silico study.

BACKGROUND: Fish protein is a good source of amino acids and peptides with sensory properties. Theoretically, the type of protein affects the taste quality of the protein hydrolysates. To better use fish protein in the food ingredients industry, an in silico approach was adopted to evaluate the potential of fish protein to release taste-active compounds. RESULTS: Six types of protein from seven commercial fishes were screened from the Uniprot knowledge base. The results showed that a remarkable number of umami fragments presented in myosin and parvalbumin (PB), such as glutamic acid (Glu), aspartic acid (Asp), and Asp- and Glu- containing peptides, whereas sweet amino acids and bitter peptides (e.g., Pro- and Gly- containing peptides) were mainly found in collagen (CGI) in all fish samples. After the in silico proteolysis by papain, a difference in the profile of taste-active fragments was observed among the six types of proteins. Amino acids were the main hydrolysis products of these proteins, especially umami, sweet, and bitter amino acids, significantly contributing to the taste formation of protein hydrolysates. Besides, the myosin and CGI hydrolysates were abundant in taste active peptides both in types and quantities. CONCLUSION: Myosin is a promising protein source for producing umami fragments, and CGI seems to be a good precursor of sweet and bitter fragments. Different types of protein have an essential effect on the taste of protein hydrolysates. © 2022 Society of Chemical Industry.

Changes in the free amino acid profile of pickling cucumber during lactic acid fermentation.

Free amino acid (FAA) profiles of fresh, acidified, naturally fermented, and starter culture fermented cucumbers were analyzed by liquid chromatography triple quadrupole mass spectrometry. Fermented cucumbers contained more total FAA than acidified cucumbers (1,302 ± 102 mg/kg and 635 ± 35 mg/kg, respectively). Total FAA content of fermented cucumber was similar regardless of brine salt levels (2-6% NaCl) and starter culture addition. Glutamine (1491.4 ± 69.3 mg/kg), γ-aminobutyric acid (GABA, 269.6 ± 21.4 mg/kg), asparagine (113.0 ± 6.4 mg/kg), and citrulline (110.3 ± 8.5 mg/kg) were the most abundant FAA in fresh pickling cucumber, whereas GABA (181.3 ± 21.5 mg/kg), isoleucine (165.2 ± 11.2 mg/kg), leucine (129.8 ± 10.9 mg/kg), and lysine (110.9 ± 5.0 mg/kg) were the most abundant in fermented cucumber. GABA and ornithine were produced during fermentation, indicating glutamate decarboxylase and arginine deiminase activities. Notably, ornithine was significantly higher in natural (63.3 ± 31.5 mg/kg) versus starter culture fermented cucumbers (3.0 ± 0.7 mg/kg). This new information on FAA composition of fresh and fermented pickling cucumbers shows the impact of fermentation conditions on cucumber amino acid profiles while providing insight for manipulating fermentations for health promotion and consumer acceptance. PRACTICAL APPLICATION: This study reports changes in the free amino acid profiles of raw, fermented and acidified cucumbers, which may be valuable for understanding the impact of these foods on human health and nutrition. This information is useful for food microbiologists studying the metabolism of lactic acid bacteria during fermentation and/or designing starter cultures and could contribute to the development of novel fermented cucumber pickle products with enhanced nutritional value.

Isolation of a new taste-active brandy tannin A: Structural elucidation, quantitation and sensory assessment.

Enjoying a glass of spirits can be one of the delights of life. While it is well known that their taste improves during barrel aging, the molecular explanations of this phenomenon remain largely unknown. The present work aimed at searching for taste-active compounds formed in spirits during aging. An untargeted metabolomic approach using HRMS was applied on "eau-de-vie" of cognac. A fractionation protocol was then performed on brandies to isolate a targeted compound. By using HRMS and NMR, its structure was elucidated for the first time. This new ellagitannin, called brandy tannin A, considerably increased the sweetness of spirits at 2 mg/L. After development of an LC-HRMS quantitation method, it was assayed in various spirits and was detected mainly in cognacs up to 7 mg/L. These findings demonstrate the sensory contribution of this compound and more generally the relevance of combining metabolomics and separative techniques to purify new taste-active compounds.

Effects of high hydrostatic pressure (HHP) and storage temperature on bacterial counts, color change, fatty acids and non-volatile taste active compounds of oysters (Crassostrea ariakensis).

The effects of HHP and storage temperature on bacterial counts, color, fatty acids and flavor compounds of oysters Crassostrea ariakensis were investigated. Counts of Vibrio vulnificus and Vibrio parahaemolyticus decreased to undetectable levels in ≥ 400 MPa-treated oysters. Storage at -20 °C significantly restrained microbial growth compared to 4 °C (P < 0.05). L* values of HHP-treated oysters significantly increased compared to raw oysters (P < 0.05). Storage slightly affected the color according to total color difference (ΔE*) values. Fatty acid profiles and betaine contents in 400 and 600 MPa-treated oysters at 0 and 15 d were almost the same as raw samples. Contents of total free amino acids (FAAs), Na+ and Ca2+ were significantly higher in 400 and 600 MPa-treated oysters than those in raw oysters at 0 d (P < 0.05), while the opposite results were observed in 5'-adenosine monophosphate (AMP), 5'-guanosine monophosphate (GMP), citric acid, succinic acid, K+ and PO43- (P < 0.05). At 400 and 600 MPa, FAAs significantly decreased after 15-d storage at 4 °C and -20 °C (P < 0.05), while no significant changes were observed in nucleotides, organic acids and inorganic ions.

Taste and stability characteristics of two key umami peptides from pufferfish (Takifugu obscurus).

Takifugu obscurus (T. obscurus) is known for its umami taste. Two taste-active peptides, Pro-Val-Ala-Arg-Met-Cys-Arg (PR-7) and Tyr-Gly-Gly-Thr-Pro-Pro-Phe-Val (YV-8), were proved as key compounds that contributed to the typical taste of T. obscurus. However, whether these peptides have the potential as umami supplements is unknown. The purpose of this study was to investigate the taste characteristics of PR-7 and YV-8, as well as stability at different pH values by sensory evaluation, instrumental analysis and quantum chemical calculation. The results indicated that PR-7 and YV-8 presented umami taste at near neutral pH (6.5-8.0) and had umami-enhancing effects. PR-7 also exhibited significant kokumi activity. Additionally, two peptides showed remarkable stability after different pH treatments, especially YV-8; this may be related to its stable structural property. All the results suggest that both peptides have great potential to be applied in complex foods to provide desirable taste, and act as a feasible alternative to monosodium l-glutamate.

Taste-Active and Nutritional Components of Thai Native Chicken Meat: A Perspective of Consumer Satisfaction.

The taste-active and nutritional components of Thai native, broilers, black-boned, and spent hen chickens were analyzed. The amounts of tasty amino acids especially glutamic acid were the highest in Thai native chicken. The black-boned chicken had the highest arginine content, related to the least amount of consumer satisfaction. Concerning nutritional quality, choline, and taurine were deemed important for brain function. The black-boned chicken showed the highest choline and taurine contents, unlike that of the spent hens. In contrast, broilers presented the highest betaine content, which might be attributed to their lipid metabolism. L-carnitine content was abundant in black-boned and Thai native chickens. Moreover, the amounts of essential amino acids were high in Thai native chicken. In conclusion, black-boned chicken proved to be an excellent nutritional source for health-conscience consumers, whereas the Thai native chickens were flavourful and delicious.

Untargeted LC-HRMS profiling followed by targeted fractionation to discover new taste-active compounds in spirits.

Taste is a key driver of food and beverage acceptability due to its role in consumers' pleasure. The great interest that natural food and beverages now arouse lies notably in the complexity of their taste, which in turn is related to a wide range of taste-active compounds. Going beyond the classic divide between targeted and untargeted strategies, an integrative methodology to spirits was applied. Untargeted profiling of several cognac spirits was implemented by LC-HRMS to identify compounds of interest among hundreds of ions. A targeted fractionation protocol was then developed. By using HRMS and NMR, dihydrodehydrodiconiferyl alcohol was identified and described for the first time in spirits and oak wood. It was characterized as sweet at 2 mg/L in two matrices and was quantified in spirits up to 4 mg/L. These findings demonstrated how this methodology is relevant and effective to discover new taste-active compounds.

Objective measures of greengage wine quality: From taste-active compound and aroma-active compound to sensory profiles.

This study is sought to identify the components in greengage wine that predict the sensory properties. Taste-active compounds and aroma-active compounds of 20 commercially available greengage wines from different regions were characterized. The relationship between these compounds, wine samples and sensory attributes was modeled by partial least squares regression. The regression analysis indicated the taste-active compounds, alanine, leucine, proline, glutamic acid, lysine, malic acid, citric acid, sucrose, glucose, gallic acid, caffeic acid and tannin made a great contribution to the characteristic taste or mouthfeel of greengage wine. Meanwhile, the aroma-active compounds, including ethyl acetate, ethyl butanoate, ethyl hexanoate, ethyl octanoate, ethyl decanoate, 3-methylbutanol, 5-hydroxymethylfurfural, octanoic acid and benzaldehyde, modeled well with the flavor characteristic of greengage wine. The study revealed new insights into the relationship between chemistry and wine sensory characters, which has implications for developing an objective measurement system for determining greengage wine quality.