Assessment of Changes in Sensory Characteristics of Strawberries during 5-Day Storage through Correlation between Human Senses and Electronic Senses.

In the last decade, significant efforts have been made to predict sensory characteristics using electronic senses, such as the electronic nose (e-nose) and the electronic tongue (e-tongue), and discuss their relationship to the eating quality evaluated by human panels. This study was conducted (1) to characterize the aroma and taste profiles of strawberries over a 5-day storage period (4 °C) using both electronic senses and human panels and (2) to correlate the electronic sense data with human panel data. A total of 10 sensory attributes of strawberries, including 7 aroma and 3 taste attributes, were analyzed by a descriptive sensory panel (n = 16) over the five days. Although the human panel did not find significant differences in the intensities of the strawberry attributes over the five days, the intensity ratings showed an increasing or decreasing trend over the storage period. However, the e-nose and the e-tongue discriminated each of the storage days of the strawberry samples. Furthermore, the partial least square regression coefficients of determination (R2) indicated that the e-nose and the e-tongue were highly predictive in their evaluation of the intensities of all the descriptive sensory attributes. Lastly, the concentrations of furaneol, one of the key volatiles imparting a distinct ripe strawberry aroma, were determined using an e-nose to correlate with the intensities of aroma attributes evaluated by the panel. A significant positive Pearson's correlation coefficient was found with the intensities of overripe aroma. The findings indicate the potential of electronic senses to determine sensory characteristics and their excellent capability to predict the eating quality of strawberries.

Results of patch testing with five fragrance materials hitherto not tested: A dose-finding study in the clinical population.

BACKGROUND: Quantitative risk assessment (QRA) for skin sensitization is used to derive safe use levels of sensitising fragrance ingredients in products. Post-marketing surveillance of the prevalence of contact allergy to these ingredients provides relevant data to help evaluate the performance of these measures. OBJECTIVES: To determine a suitable patch test concentration for five fragrance materials that had hitherto not been tested on a regular basis. These concentrations are then to be used in a surveillance study with patch testing consecutive patients over an extended monitoring period. MATERIALS AND METHODS: Furaneol, CAS.3658-77-3; trans-2-hexenal, CAS.6728-26-3; 4,8-dimethyl-4,9-decadienal, CAS.71077-31-1; longifolene, CAS.475-20-7; benzaldehyde, CAS.10052-7, were patch tested with other fragrance allergens in four clinics. Patch testing was conducted in three rounds, starting with the lowest concentrations of the five ingredients. The doses were increased in the subsequent rounds if no late-appearing positive reactions and virtually no irritant reactions were reported. RESULTS: Overall, 373 patients were tested. No positive allergic reaction was reported to the five ingredients. Patch test results of other fragrance allergens are reported. CONCLUSIONS: The highest test concentrations are each considered safe for patch testing consecutive patients. Further surveillance based on these preparations will evaluate the hypothesis that QRA-driven consumer product levels of these fragrances can prevent sensitization.

Plant-based meat substitute analysis using microextraction with deep eutectic solvent followed by LC-MS/MS to determine acrylamide, 5-hydroxymethylfurfural and furaneol.

For the analysis of plant-based meat substitutes and the determination of Maillard reaction products such as acrylamide, 5-hydroxymethylfurfural and furaneol, a novel and effective procedure based on hydrophobic natural deep eutectic solvent and liquid chromatography coupled with tandem mass spectrometry was developed for the first time. The 49 compositions of the deep eutectic solvents were designed and screened to select the most suitable option. The terpenoids eugenol and thymol in a molar ratio of 2:1 were selected as precursors for solvent formation, allowing effective extraction of the target analytes. The developed procedure comprised two main steps: extraction - in which the analytes are isolated from the solid sample due to the salting-out effect and pre-concentrated in the deep eutectic solvent, and back-extraction - in which the analytes are re-extracted into the formic acid solution for subsequent mass spectrometric detection. As the density of the aqueous phases changed during the extraction and back-extraction steps, the phenomenon of inversion of the coalesced organic phase was observed, which simplified the withdrawing of the phases. The linear range was 1-50 ng/mL for acrylamide, 10-1000 ng/mL for 5-hydroxymethylfurfural and 200-1000 ng/mL for furaneol with coefficients of determination above 0.9952. The developed method was fully validated and found recoveries were in the range 83-120%, with CVs not exceeding 4.9%. The method was applied to real sample analysis of pea-based meat substitutes.

Identification of ethyl vanillin in strawberry (Fragaria × ananassa) using a targeted metabolomics strategy: From artificial to natural.

Improving flavor can be an important goal of strawberry through breeding that is enhanced through the accurate identification and quantification of flavor compounds. Herein, a targeted metabolomics strategy was developed using liquid-liquid extraction, an in-house standard database, and GC-MS/MS analysis. The database consisted of key food odorants (KFOs), artificial flavor compounds (AFCs) and volatiles. A total of 131 flavor compounds were accurately identified in Medallion® 'FL 16.30-128' strawberry. Importantly, ethyl vanillin was identified for the first time in natural food. Multiple techniques, including GC-MS, GC-MS/MS and UPLC-MS/MS were applied to ensure the identification. The ethyl vanillin in the Medallion® samples were determined in a range of concentrations from 0.070 ± 0.0006 µg/kg to 0.1372 ± 0.0014 µg/kg by using stable isotope dilution analysis. The identification of ethyl vanillin in strawberry implys the future commercial use a natural flavor compound and the potential to identify genes and proteins associated with its biosynthesis.

Identification of dominant functional microbes that contribute to the characteristic aroma of Msalais, traditional wine fermented from boiled local grape juice in China.

Msalais is a traditional wine produced from naturally fermented boiled local grape juice in China. It has characteristic dried fruit and caramel odors, mainly attributed to aromatic compounds, such as furaneol and 5-methylfurfural. However, it is unclear how microbes involved in the natural fermentation of Msalais contribute to this characteristic aroma. Here, we analyzed the Msalais-fermenting microbes and aromatic compounds formed during natural Msalais fermentation by using high-throughput sequencing and gas chromatography-mass spectrometry, respectively. The analysis revealed that Saccharomyces cerevisiae, Kazachstania humilis, Lactobacillus plantarum, and Lactobacillus farraginis are the dominant and key functional species that produce high amounts of furaneol and 5-methylfurfural during Msalais fermentation. Of these, K. humilis and L. farraginis are rarely detected during regular wine fermentation. The identified functional species could be used to control typical aromatic characteristics of Msalais.

Optimization and Validation of a Method to Determine Enolones and Vanillin Derivatives in Wines-Occurrence in Spanish Red Wines and Mistelles.

Understanding the chemical nature of wine aroma demands accurate quantitative determinations of different odor-active compounds. Quantitative determinations of enolones (maltol, furaneol, homofuraneol, and sotolon) and vanillin derivatives (vanillin, methyl vanillate, ethyl vanillate, and acetovanillone) at low concentrations are complicated due to their high polarity. For this reason, this paper presents an improved and automated version for the accurate measure of these common trace wine polar compounds (enolones and vanillin derivatives). As a result, a faster and more user-friendly method with a reduction of organic solvents and resins was developed and validated. The optimization of some stages of the solid phase extraction (SPE) process, such as washing with an aqueous solution containing 1% NaHCO3 at pH 8, led to cleaner extracts and solved interference problems. Due to the polarity of these type of compounds, an optimization of the large volume injection was also carried out. Finally, a programmable temperature vaporization (PTV) quartz glass inlet liner without wool was used. The injector temperature was raised to 300 °C in addition to applying a pressure pulse of 180 kPa for 4 min. Matrix effects were solved by the use of adequate internal standards, such as ethyl maltol and 3',4'-(methylenedioxy)acetophenone. Method figures of merit were highly satisfactory: good linearity (r2 > 0.98), precision (relative standard deviation, RSD < 10%), high recovery (RSD > 89%), and low detection limits (<0.7 µg/L). Enolones and vanillin derivatives are associated with wine aging. For this reason, the methodology was successfully applied to the quantification of these compounds in 16 Spanish red wines and 12 mistelles. Odor activity values (OAV) indicate that furaneol should be considered an aroma impact odorant in red wines and mistelles (OAV > 1) while homofuraneol and sotolon could also produce changes in their aroma perceptions (0.1 < OAV < 1).

Molecularly Imprinted Chemiresistive Sensor for Specific Recognition of Furaneol as a Biomarker of Strawberry Flavor Conditions.

This work introduces the concept of a molecularly imprinted gas sensor to monitor the condition of naturally ripened strawberries. Furaneol, 2,5-dimethyl-4-hydroxy-3(2H)-furanone, is considered as an important biomarker related to the strawberry flavor. Identification of furaneol concentration is still a challenge because of its weak adsorption, nonpolar, and unreactive properties. Therefore, no study has been reported yet to measure furaneol gases via a simple chemiresistive mechanism. Herein, we demonstrate the sensor based on molecularly imprinted polymer (MIP)-based polyaniline (PANI). The sensitive and selective detection of furaneol gas with a MIP-PANI gas sensor was observed at room temperature and under different humidity conditions. The comparison between MIP and the nonimprinted (NIP)-based PANI shows a strong interaction between furaneol and the molecularly imprinted polymer. The furaneol gas sensing mechanism is explained based on the interaction between the gas molecules and the charge carriers of MIP-PANI, which results in the functional group change in the carboxylic group. Furthermore, the developed MIP-chemiresistive sensor for real strawberries was compared with a commercial e-nose system. The results show the potential to offer a rapid and cost-effective platform for specific recognition of furaneol.

Aromatic characterization of traditional Chinese wine Msalais by partial least-square regression analysis based on sensory quantitative descriptive and odor active values, aroma extract dilution analysis, and aroma recombination and omission tests.

Msalais is produced from local grape juice in southern Xinjiang (China), by concentration and natural fermentation. In the current study, we combined partial least-square regression analysis based on sensory quantitative descriptive and odor active values (OAVs), aroma extract dilution analysis, and aroma recombination and omission tests to delineate the unique aromatic characteristics of traditional Msalais. Msalais has strong dried fruit, fruit jam, and fruity odors, intermediate-strength caramel and baked odors, and weak floral and herbaceous odors, attributed to 24 key aromatic compounds with OAV ≥1 or flavor dilution ≥4. Furaneol, methionol, and 5-methylfurfural greatly contribute to the dried fruit, fruit jam, and caramel odors, respectively. ß-Phenylethyl alcohol mostly contributes to fruit jam odor. ß -Damascenone has a complicated effect on dried fruit, fruit jam, and floral odors. Fruity esters contribute to fruity odor. Floral odor is attributed to terpenes. These findings allow precise improvement of the variable quality of traditional Msalais.

Characterization of the potent odorants in Tibetan Qingke Jiu by sensory analysis, aroma extract dilution analysis, quantitative analysis and odor activity values.

Tibetan Qingke Jiu is the most important alcoholic beverage in the daily life of Tibetan people due to its unique flavor and rich nutrients. In this study, the aromatic characteristics of Qingke Jiu were studied by sensory analysis, aroma extract dilution analysis (AEDA), quantitative analysis, and odor activity values (OAVs). Sensory evaluation demonstrated that Qingke Jiu had fruity, cooked potato, honey, sour, sweet, and caramel-like aroma. A total of 66 aroma compounds were identified by AEDA and gas chromatography-mass spectrometry, with flavor dilution (FD) factors ranging from 4 to 2048. Among them, methional, acetic acid, ethyl butanoate, phenylacetaldehyde and ß-phenylethanol appeared with the highest FD factors. The concentration of these aroma-active compounds was further quantitated by combination of four different quantitative measurements, and 17 odorants had concentrations higher than their odor thresholds. Based on the OAVs, phenylacetaldehyde, ß-phenylethanol, ethyl phenylacetate, sotolon, furaneol, methional, methionol, γ-nonalactone, ethyl 2-methylbutanoate, ß-damascenone, ethyl 3-methylbutanoate, ethyl acetate, ethyl butanoate, and acetic acid could be potentially important to the overall aroma profile of Qingke Jiu.

Flexible Screen Printed Aptasensor for Rapid Detection of Furaneol: A Comparison of CNTs and AgNPs Effect on Aptasensor Performance.

Furaneol is a widely used flavoring agent, which can be naturally found in different products, such as strawberries or thermally processed foods. This is why it is extremely important to detect furaneol in the food industry using ultra-sensitive, stable, and selective sensors. In this context, electrochemical biosensors are particularly attractive as they provide a cheap and reliable alternative measurement device. Carbon nanotubes (CNTs) and silver nanoparticles (AgNPs) have been extensively investigated as suitable materials to effectively increase the sensitivity of the biosensors. However, a comparison of the performance of biosensors employing CNTs and AgNPs is still missing. Herein, the effect of CNTs and AgNPs on the biosensor performance has been thoughtfully analyzed. Therefore, disposable flexible and screen printed electrochemical aptasensor modified with CNTs (CNT-ME), or AgNPs (AgNP-ME) have been developed. Under optimized conditions, CNT-MEs showed better performance compared to AgNP-ME, yielding a linear range of detection over a dynamic concentration range of 1 fM-35 µM and 2 pM-200 nM, respectively, as well as high selectivity towards furaneol. Finally, our aptasensor was tested in a real sample (strawberry) and validated with high-performance liquid chromatography (HPLC), showing that it could find an application in the food industry.

Levels of Furaneol in Msalais Wines: A Comprehensive Overview of Multiple Stages and Pathways of Its Formation during Msalais Winemaking.

4-Hydroxy-2,5-dimethyl-3(2H)-furanone (furaneol) is present in food. It has a caramel-like flavor, which affects the quality of food, and is formed via multiple pathways. Msalais is a traditional wine fermented from boiled local grape juice in Xinjiang (China). It has a strong caramel odor, which suggests high furaneol content. Furaneol formation during Msalais-making had not been investigated to date. Here, high-performance liquid chromatography and different fermentation models of Msalais-making were used to investigate the furaneol content and formation during Msalais-making. The furaneol content of Msalais is high, between 27.59 ± 0.493 mg/L and 117.6 ± 0.235 mg/L. It is formed throughout the entire Msalais-making process. The formation pathways include the Maillard reaction and chemical hydrolysis of bound furaneol during grape juice concentration; enzymatic release and/or chemical acidic hydrolysis of furaneol glucosides, and biosynthesis from Maillard products and d-fructose-1,6-diphosphate during fermentation; chemical transformation of Maillard products at room temperature (16-25 °C) and hydrolysis of furaneol glucosides during storage. Importantly, furaneol is formed by an efficient biotransformation of Maillard products. These findings suggest that furaneol content can be used as an important indicator of wine quality, and could be controlled by controlling the grape quality, grape juice concentration, fermentation, and wine storage.

Selection, Characterization, and Application of ssDNA Aptamer against Furaneol.

Furaneol is an aroma compound which occurs naturally in foods and is used as an artificial flavor. Detection of furaneol is required in food science and food processing industry. Capture- Systematic Evolution of Ligands by EXponential enrichment (SELEX) protocol was applied for the isolation of an aptamer binding to furaneol, a small volatile organic substance contributing to the flavor of various products. Thirteen cycles of selection were performed. The resulting DNA pool was cloned, using blunt-end cloning, and ninety-six plasmids were sequenced and analyzed. Eight oligonucleotides were selected as aptamer candidates and screened for the ability to bind to furaneol, using three different methods-magnetic-beads associated elution assay, SYBR Green I assay, and exonuclease protection assay. One of the candidates was further characterized as an aptamer. The apparent equilibrium constant was determined to be (1.1 ± 0.4) µM, by the fluorescent method. The reported aptamer was applied for development of the ion-sensitive field-effect transistor (ISFET)-based biosensor, for the analysis of furaneol, in the concentration range of 0.1⁻10 µM.

Selecting odorant compounds to enhance sweet flavor perception by gas chromatography/olfactometry-associated taste (GC/O-AT).

Gas chromatography/olfactometry-associated taste (GC/O-AT) analysis combined with mass spectrometry allowed identification of odorant compounds associated with taste attributes (sweet, salty, bitter and sour) in a multi-fruit juice. Nine compounds were selected for their odor-associated sweetness enhancement in a multi-fruit juice odor context using Olfactoscan and for their odor-induced sweet taste enhancement in sucrose solution and sugar-reduced fruit juice through sensory tests. Sweetness of the fruit juice odor was significantly enhanced by methyl 2-methylbutanoate, ethyl butanoate, ethyl 2-methylbutanoate and linalool; sweet perception was significantly enhanced in 7% sucrose solution by ethyl 2-methylbutanoate, furaneol and γ-decalactone, and in 32% sugar-reduced fruit juice by ethyl 2-methylbutanoate. GC/O-AT analysis is a novel, efficient approach to select odorants associated with a given taste. The further screening of taste-associated odorants by Olfactoscan helps to identify the most efficient odorants to enhance a target taste perception and may be used to find new ways to modulate taste perception in foods and beverages.

Key volatile aroma compounds of lactic acid fermented malt based beverages - impact of lactic acid bacteria strains.

This study aims to define the aroma composition and key aroma compounds of barley malt wort beverages produced from fermentation using six lactic acid bacteria (LAB) strains. Gas chromatography mass spectrometry-olfactometry and flame ionization detection was employed; key aroma compounds were determined by means of aroma extract dilution analysis. Fifty-six detected volatile compounds were similar among beverages. However, significant differences were observed in the concentration of individual compounds. Key aroma compounds (flavor dilution (FD) factors ≥16) were ß-damascenone, furaneol, phenylacetic acid, 2-phenylethanol, 4-vinylguaiacol, sotolon, methional, vanillin, acetic acid, nor-furaneol, guaiacol and ethyl 2-methylbutanoate. Furthermore, acetaldehyde had the greatest odor activity value of up to 4266. Sensory analyses revealed large differences in the flavor profile. Beverage from L. plantarum Lp. 758 showed the highest FD factors in key aroma compounds and was correlated to fruity flavors. Therefore, we suggest that suitable LAB strain selection may improve the flavor of malt based beverages.

Effect of xanthan gum on the release of strawberry flavor in formulated soy beverage.

The effects of xanthan gum on the release of strawberry flavor compounds in formulated soy protein isolate (SPI) beverage were investigated by headspace gas chromatography (GC). Seven strawberry flavor compounds (limonene, ethyl hexanoate, (Z)-3-hexenyl acetate, ethyl 2-methylbutanoate, ethyl butanoate, (Z)-3-hexen-1-ol and diacetyl) could be detected by GC and hence analyzed the gas-matrix partition coefficients (K). The release of flavor compounds was restrained in SPI and/or xanthan gum solution. The retention of (Z)-3-hexen-1-ol, limonene and diacetyl significantly changed (p<0.05) with increasing xanthan gum concentrations. Presence of any other esters led to suppression of the release of ester compounds in water and SPI solution. The less-volatiles (γ-decalactone, methyl cinnamate, hexanoic acid, 2-methyl butyric acid and furaneol) accelerated the release of ester compounds to some extent in different matrices. The above results demonstrated that presence of SPI and xanthan gum could bring about an imbalance in the strawberry flavor.

Formation of the reduced form of furaneol® (2,5-dimethyl-4-hydroxy-tetrahydrofuran-3-one) during the Maillard reaction through catalysis of amino acid metal salts.

Under pyrolytic conditions the acidity/basicity of Maillard reaction mixtures can be controlled through the use of hydrochloride or sodium salts of amino acids to generate a diversity of products. When the degradation of glucose was studied under pyrolytic conditions using excess sodium glycinate the reaction was found to generate a major unknown peak having a molecular ion at m/z 130. Subsequent in-depth isotope labelling studies indicated that acetol was an important precursor of this compound under pyrolytic and aqueous heating conditions. The dimerisation and cyclisation of acetol into 2,5-dimethyl-4-hydroxy-tetrahydrofuran-3-one was found to be catalysed by amino acid metal salts. Also, ESI/qTOF/MS studies indicated that the unknown peak has expected molecular formula of C6H10O3. Finally, a peak having the same retention time and mass spectrum was also generated pyrolytically when furaneol® was reduced with NaBH4 confirming the initial hypothesis regarding the unknown peak to be the reduced form of furaneol®.

Sensory interactions between six common aroma vectors explain four main red wine aroma nuances.

This work aims at assessing the aromatic sensory dimensions linked to 6 common wine aroma vectors (N, norisoprenoids; A, branched acids; F, enolones; E, branched ethyl esters; L, fusel alcohols, M, wood compounds) varying in their natural range of occurrence. Wine models were built by adding the vectors at two levels (fractional factorial design 2(VI)) to a de-aromatised aged red wine. Twenty other different models were evaluated by descriptive analysis. Red, black and dried fruits and woody notes were satisfactorily reproduced. Individual vectors explained just 15% of the sensory space, mostly dependent on perceptual interactions. N influences dried and black fruits and suppresses red fruits. A suppresses black fruits and enhances red and dried fruits. F exerts a major role on red fruits. E suppresses dried fruits and modulates black fruits. L is revealed as a strong suppressor of red fruits and particularly of woody notes.

Molecular cloning and characterization of UDP-glucose: furaneol glucosyltransferase gene from grapevine cultivar Muscat Bailey A (Vitis labrusca × V. vinifera).

2,5-Dimethyl-4-hydroxy-3(2H)-furanone (furaneol) is an important aroma compound in fruits, such as pineapple and strawberry, and is reported to contribute to the strawberry-like note in some wines. Several grapevine species are used in winemaking, and furaneol is one of the characteristic aroma compounds in wines made from American grape (Vitis labrusca) and its hybrid grape. Furaneol glucoside was recently isolated as an important furaneol derivative from the hybrid grapevine cultivar, Muscat Bailey A (V. labrusca × V. vinifera), and this was followed by its isolation from some fruits such as strawberry and tomato. Furaneol glucoside is a significant 'aroma precursor of wine' because furaneol is liberated from it during alcoholic fermentation. In this study, a glucosyltransferase gene from Muscat Bailey A (UGT85K14), which is responsible for the glucosylation of furaneol was identified. UGT85K14 was expressed in the representative grape cultivars regardless of species, indicating that furaneol glucoside content is regulated by the biosynthesis of furaneol. On the other hand, furaneol glucoside content in Muscat Bailey A berry during maturation might be controlled by the expression of UGT85K14 along with the biosynthesis of furaneol. Recombinant UGT85K14 expressed in Escherichia coli is able to transfer a glucose moiety from UDP-glucose to the hydroxy group of furaneol, indicating that this gene might be UDP-glucose: furaneol glucosyltransferase in Muscat Bailey A.

Structural basis for the enzymatic formation of the key strawberry flavor compound 4-hydroxy-2,5-dimethyl-3(2H)-furanone.

The last step in the biosynthetic route to the key strawberry flavor compound 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF) is catalyzed by Fragaria x ananassa enone oxidoreductase (FaEO), earlier putatively assigned as quinone oxidoreductase (FaQR). The ripening-induced enzyme catalyzes the reduction of the exocyclic double bond of the highly reactive precursor 4-hydroxy-5-methyl-2-methylene-3(2H)-furanone (HMMF) in a NAD(P)H-dependent manner. To elucidate the molecular mechanism of this peculiar reaction, we determined the crystal structure of FaEO in six different states or complexes at resolutions of ≤1.6 Å, including those with HDMF as well as three distinct substrate analogs. Our crystallographic analysis revealed a monomeric enzyme whose active site is largely determined by the bound NAD(P)H cofactor, which is embedded in a Rossmann-fold. Considering that the quasi-symmetric enolic reaction product HDMF is prone to extensive tautomerization, whereas its precursor HMMF is chemically labile in aqueous solution, we used the asymmetric and more stable surrogate product 2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone (EHMF) and the corresponding substrate (2E)-ethylidene-4-hydroxy-5-methyl-3(2H)-furanone (EDHMF) to study their enzyme complexes as well. Together with deuterium-labeling experiments of EDHMF reduction by [4R-(2)H]NADH and chiral-phase analysis of the reaction product EHMF, our data show that the 4R-hydride of NAD(P)H is transferred to the unsaturated exocyclic C6 carbon of HMMF, resulting in a cyclic achiral enolate intermediate that subsequently becomes protonated, eventually leading to HDMF. Apart from elucidating this important reaction of the plant secondary metabolism our study provides a foundation for protein engineering of enone oxidoreductases and their application in biocatalytic processes.