Characterization of the key aroma compounds in soy sauce using approaches of molecular sensory science

Application of aroma extract dilution analysis (AEDA) to the volatiles isolated from a commercial Japanese soy sauce revealed 30 odor-active compounds in the flavor dilution (FD) factor range of 8-4096, among which 2-phenylethanol showed the highest FD factor of 4096, followed by 3-(methylsulfanyl)propanal (methional), the tautomers 4-hydroxy-5-ethyl-2-methyl- and 4-hydroxy-2-ethyl-5-methyl-3(2H)-furanone (4-HEMF), 4-hydroxy-2,5-dimethyl-3(2H)-furanone (4-HDF), and 3-hydroxy-4,5-dimethyl-2(5H)-furanone (sotolone), all showing FD factors of 1024. Thirteen odorants were quantified by stable isotope dilution assays, and their odor activity values (OAVs) were calculated as ratio of their concentrations and odor thresholds in water. Among them, 3-methylbutanal (malty), sotolone (seasoning-like), 4-HEMF (caramel-like), 2-methylbutanal (malty), methional (cooked potato), ethanol (alcoholic), and ethyl 2-methylpropanoate (fruity) showed the highest OAVs (>200). An aqueous model aroma mixture containing 13 odorants, which had been identified with the highest OAVs, in concentrations that occur in the soy sauce showed a good similarity with the overall aroma of the soy sauce itself. Heat treatment of the soy sauce resulted in a clear change of the overall aroma. Quantitation of selected odorants revealed a significant decrease in sotolone and, in particular, increases in 2-acetyl-1-pyrroline, 4-HDMF, and 4-HEMF induced by heating.     

Characteristics and use of okara, the soybean residue from soy milk production--a review

Large quantities of okara produced annually pose a significant disposal problem. It contains mostly crude fiber composed of cellulose, hemicellulose, and lignin, about 25% protein, 10-15% oil, but little starch or simple carbohydrates. It is a suitable dietary additive in biscuits and snacks because it reduces calorie intake and increases dietary fiber. The high-quality protein fraction has good water holding and emulsifying qualities and contains a peptide with anti-hypertension effects. The pectic polysaccharides fraction is suitable for thickening acid milk products. Okara fermented with Actinomucor elegans (meitauza), Aspergillus oryzae (koji), Neurospora intermedia (ontjom), and Rhizopus oligosporus (tempe), on consumption, reduces cholesterol level and contains substances that counteract dietary free radicals. Unique and useful products produced by Bacillus subtilis and Penicillium simplicissimum on okara include surfactin and iturin A (fungicidal), okaramines A, B, D-F (D is insecticidal), an oleanane triterpene, and two dihydroquinolinones (one toxic for Artemia salina). Okara has been used as silkworm food and in the production of ceramics.     

Comparison of key aroma compounds in cooked brown rice varieties based on aroma extract dilution analyses

The aroma compounds present in cooked brown rice of the three varieties Improved Malagkit Sungsong (IMS), Basmati 370 (B 370), and Khaskhani (KK), and of the variety Indica (German supermarket sample), were identified on the basis of aroma extract dilution analyses (AEDA). A total of 41 odor-active compounds were identified, of which eleven are reported for the first time as rice constituents. 2-Amino acetophenone (medicinal, phenolic), which was up to now unknown in rice aroma, exhibited the highest flavor dilution (FD) factor among the 30 to 39 odor-active compounds detected in all four varieties. 2-Acetyl-1-pyrroline, exhibiting an intense popcorn-like aroma-note, was confirmed as a further key aroma constituent in IMS, B 370, and KK, but was not important in Indica. Differences in the FD factors between the varieties were found for the previously unknown rice aroma compound 3-hydroxy-4,5-dimethyl-2(5H)-furanone (Sotolon; seasoning-like), which was higher in B 370 than in IMS and KK. In IMS, a yet unknown, spicy smelling component with a very high FD factor could be detected, which contributed with lower FD factors to the overall aromas of B 370 and KK, and was not present in Indica. The latter variety, which was available on the German market, differed most in its overall aroma from the three Asian brown rices.     

Volatile compounds from three cultivars of Olea europaea from Italy.

The chemical compositions of the volatile fractions from three Olea europaea L. cultivars (Leccino, Frantoio, and Cipressino) were examined by GC and GC-MS. The results showed that the cultivars can be distinguished on the basis of the volatile fraction compositions.     

Identification of the key aroma compounds in cocoa powder based on molecular sensory correlations

Isolation of the volatile fraction from cocoa powder (50 g; 20% fat content) by a careful extraction/distillation process followed by application of an aroma extract dilution analysis revealed 35 odor-active constituents in the flavor dilution (FD) factor range of 8-4096. Among them, 4-hydroxy-2,5-dimethyl-3(2H)-furanone (caramel-like), 2- and 3-methylbutanoic acid (sweaty, rancid), dimethyl trisulfide (cooked cabbage), 2-ethyl-3,5-dimethylpyrazine (potato-chip-like), and phenylacetaldehyde (honey-like) showed the highest FD factors. Quantitation of 31 key odorants by means of stable isotope dilution assays, followed by a calculation of their odor activity values (OAVs) (ratio of concentration to odor threshold) revealed OAVs>100 for the five odorants acetic acid (sour), 3-methylbutanal (malty), 3-methylbutanoic acid, phenylacetaldehyde, and 2-methylbutanal (malty). In addition, another 19 aroma compounds showed OAVs>1. To establish their contribution to the overall aroma of the cocoa powder, these 24 compounds were added to a reconstructed cocoa matrix in exactly the same concentrations as they occurred in the cocoa powder. The matrix was prepared from deodorized cocoa powder, which was adjusted to 20% fat content using deodorized cocoa butter. The overall sensory evaluation of this aroma recombinate versus the cocoa powder clearly indicated that the 24 compounds represented the typical sweet, cocoa-like odor of the real sample.     

不同品种大豆加工豆浆的品质分析及评价模型

东北是中国大豆的主产区,也是传统豆制品的重要原料生产基地。为明确该产区大豆原料与其加工制得豆浆的品质、特点,该研究选取47个东北大豆品种为原料,分析其大豆粗脂肪、粗蛋白、钙、磷含量等理化指标,比较其加工豆浆的蛋白浓度、总固形物含量、感官评价、风味物质含量等品质差异。结果得到豆浆质量得率、动力粘度、总固形物、非豆腥味活性与豆腥味活性比值最高的品种分别是吉育102、吉92、吉育70、吉小8号、吉青3号。大豆籽粒理化指标分析结果显示,粗蛋白、粗脂肪、钙、磷含量最高的品种分别为垦丰17、GY07Y16、吉82、杂交豆3号。豆浆的豆腥味与脂肪氧化酶活性、油酸、亚油酸、亚麻酸含量呈显著正相关,脂肪含量与风味活性比呈负相关。利用因子分析法提取出4个因子方程,确定豆浆各项指标在综合品质中所占比重,进一步建立了豆浆品质评价模型,模型系数可以根据加工目的进行相应调整。综合得分最高的5个品种为吉45(9.52)、吉育70(9.43)、吉青1号(9.28)、吉育66(9.27)、吉育102(9.21)。结合对应的大豆理化指标排序发现,豆浆品质是大豆理化成分综合作用的结果,并非蛋白含量越高所得产品越好,脂肪含量高的品种并不适宜加工豆浆。该研究为用于加工豆浆的东北大豆品种分级提供了参考,实现了豆浆品质的综合判别及大豆加工基础数据的分析、整合。     

Formation of sulfur aroma compounds in reaction mixtures containing cysteine and three different forms of ribose

The headspace volatiles produced from buffered and unbuffered cysteine model systems, containing inosine 5'-monophosphate, ribose 5-phosphate, or ribose, were examined by GC-MS. Sulfur compounds dominated the volatiles of all systems and included mercaptoketones, furanthiols, and disulfides. The inosine monophosphate systems produced much lower quantities of volatiles than ribose phosphate or ribose systems. In the systems buffered with phosphate or phthalate buffers, both ribose and ribose phosphate systems gave similar quantities of sulfur volatiles. However, in the absence of buffer, the ribose system was relatively unreactive, especially for volatiles formed via the 2,3-enolization route in the Maillard reaction, where 4-hydroxy-5-methyl-3(2H)-furanone is a key intermediate. A number of keto-enol tautomerisms, which are known to be acid-base-catalyzed, occur in the 2,3-enolization route. This may explain the catalysis of the ribose systems by the buffers. In the ribose phosphate systems, however, Maillard mechanisms probably played a less important role, because ribose 5-phosphate readily dephosphorylated to give 4-hydroxy-5-methyl-3(2H)-furanone on heating and thus provided an easier route to aroma compounds than the Maillard reaction.     

Changes in key aroma compounds of Criollo cocoa beans during roasting

Application of a comparative aroma extraction dilution analysis on unroasted and roasted Criollo cocoa beans revealed 42 aroma compounds in the flavor dilution (FD) factor range of 1-4096 for the unroasted and 4-8192 for the roasted cocoa beans. While the same compounds were present in the unroasted and roasted cocoa beans, respectively, these clearly differed in their intensity. For example, 2- and 3-methylbutanoic acid (rancid) and acetic acid (sour) showed the highest FD factors in the unroasted beans, while 3-methylbutanal (malty), 4-hydroxy-2,5-dimethyl-3(2H)-furanone (caramel-like), and 2- and 3-methylbutanoic acid (sweaty) were detected with the highest FD factors in the roasted seeds. Quantitation of 30 odorants by means of stable isotope dilution assays followed by a calculation of odor activity values (ratio of the concentration/odor threshold) revealed concentrations above the odor threshold for 22 compounds in the unroasted and 27 compounds in the roasted cocoa beans, respectively. In particular, a strong increase in the concentrations of the Strecker aldehydes 3-methylbutanal and phenylacetaldehyde as well as 4-hydroxy-2,5-dimethyl-3(2H)-furanone was measured, suggesting that these odorants should contribute most to the changes in the overall aroma after roasting. Various compounds contributing to the aroma of roasted cocoa beans, such as 3-methylbutanoic acid, ethyl 2-methylbutanoate, and 2-phenylethanol, were already present in unroasted, fermented cocoa beans and were not increased during roasting.     

Magnesium-manganese interaction in soybean cultivars with different nutritional requirements

Manganese (Mn) deficiency in soybean has occurred mainly in soils with surface dolomite lime application, which increases pH and the magnesium (Mg) concentration in the surface layer. The objective of this study was to investigate the influence of Mg on the Mn uptake in four soybean cultivars with different nutritional requirements. The experiment was conducted under greenhouse conditions in a completely randomized design, in 4 × 2 × 4 factorial scheme [four soybean cultivars, two Mg rates (0.1 and 1.0 mmol L^?1) and four Mn rates (0.0, 1.0, 2.0, and 5.0 µmol L^?1)], with four replicates. The cultivars used in the experiment were: IAC 17 and FT Estrela (for soils fertility or high nutritional demand) and IAC 15–1 and DM Nobre (for soils partially corrected or medium nutritional demand). The root dry weight (RDW), shoot dry weight (SDW), SDW/RDW ratio, chlorophyll content, seed yield and foliar concentrations of nitrogen (N), phosphorus (P), potassium (K), Mg, calcium (Ca), iron (Fe), Mn, and zinc (Zn) were determined. The application of the highest Mg rate increased seed yield. This was also observed with a Mn rate up to 3.0 μmol L^?1. There was an interaction of Mg and Mn in the plant, and it was found that the IAC 17 cultivar was the most sensitive to Mn, while FT Estrela had the lowest performance. N, P, K, and Zn concentrations were significantly influenced by Mn rates. The Mg and Mn rates had a significant effect on Mg foliar concentrations. The rate of 1.0 mmol L^?1 of Mg provided the lowest levels of nutrients to the plant and increased SDW and seed yield, regardless of the nutritional requirement of each cultivar.     

Characterization of the key aroma compounds in cooked grey mullet (Mugil cephalus) by application of aroma extract dilution analysis

Aroma and aroma-active compounds of wild grey mullet ( Mugil cephalus ) were analyzed by gas chromatography-mass spectrometry-olfactometry (GC-MS-O). According to sensory analysis, the aromatic extract obtained by simultaneous distillation and extraction (SDE) was representative of grey mullet odor. A total of 50 aroma compounds were identified and quantified in grey mullet. Aldehydes were qualitatively and quantitatively the most dominant volatiles in grey mullet. Aroma extract dilution analysis (AEDA) was used for the determination of aroma-active compounds of fish sample. A total of 29 aroma-active compounds were detected in aromatic extract of grey mullet, of which 24 were identified. On the basis of the flavor dilution (FD) factor, the most powerful aroma active compounds identified in the extract were (Z)-4-heptenal and nonanal, which were described as the strong cooked fish and green-fruity odor, respectively.     

Characterization of the key aroma compounds in an american bourbon whisky by quantitative measurements, aroma recombination, and omission studies

Thirty-one of the 45 odor-active compounds previously identified by us in an American Bourbon whisky were quantified by stable isotope dilution assays. Also for this purpose, new synthetic pathways were developed for the synthesis of the deuterium-labeled whisky lactone as well as for gamma-nona- and gamma-decalactone. To obtain the odor activity values (OAVs), the concentrations measured were divided by the odor thresholds of the odorants determined in water/ethanol (6:4 by vol.). Twenty-six aroma compounds showed OAVs >1, among which ethanol, ethyl (S)-2-methylbutanoate, 3-methylbutanal, 4-hydroxy-3-methoxybenzaldehyde, (E)-beta-damascenone, ethyl hexanoate, ethyl butanoate, ethyl octanoate, 2-methylpropanal, (3S,4S)- cis-whiskylactone, (E, E)-2,4-decadienal, 4-allyl-2-methoxyphenol, ethyl-3-methylbutanoate, and ethyl 2-methylpropanoate showed the highest values. The overall aroma of the Bourbon whisky could be mimicked by an aroma recombinate consisting of the 26 key odorants in their actual concentrations in whisky using water/ethanol (6:4 by vol.) as the matrix. Omission experiments corroborated the importance of, in particular, 4-hydroxy-3-methoxybenzaldehyde, (3S,4S)-cis-whiskylactone, ethanol, and the entire group of esters for the overall aroma of the Bourbon whisky.     

Diffusion of aroma compounds in stirred yogurts with different complex viscosities

To better understand aroma release in relation to yogurt structure and perception, the apparent diffusivity of aroma compounds within complex dairy gels was determined using an experimental diffusion cell. Apparent diffusion coefficients of four aroma compounds (diacetyl, ethyl acetate, ethyl hexanoate, and linalool) at 7 degrees C in yogurts (varying in composition and structure) ranged from 0.07 x 10 (-10) to 8.91 x 10 (-10) m (2) s (-1), depending on aroma compounds and on product structure. The strong effect of yogurt fat content on the apparent diffusivity of hydrophobic compounds was revealed (15-fold and 50-fold decreases in the apparent diffusion coefficient of linalool and ethyl hexanoate, respectively). Protein composition seemed to have a greater effect than that of mechanical treatment. However, variations in the apparent diffusion coefficient for the considered products remained limited and cannot completely explain differences in flavor release and in perception that were previously observed.     

Comparison of accelerated methods for the extraction of phenolic compounds from different vine-shoot cultivars

Most research on the extraction of high-priced compounds from vineyard/wine byproducts has traditionally been focused on grape seeds and skins as raw materials. Vine-shoots can represent an additional source to those materials, the characteristics of which could depend on the cultivar. A comparative study of hydroalcoholic extracts from 18 different vineyard cultivars obtained by superheated liquid extraction (SHLE), microwave-assisted extraction (MAE), and ultrasound-assisted extraction (USAE) is here presented. The optimal working conditions for each type of extraction have been investigated by using multivariate experimental designs to maximize the yield of total phenolic compounds, measured by the Folin-Ciocalteu method, and control hydroxymethylfurfural because of the organoleptic properties of furanic derivatives and toxicity at given levels. The best values found for the influential variables on each extraction method were 80% (v/v) aqueous ethanol at pH 3, 180 °C, and 60 min for SHLE; 140 W and 5 min microwave irradiation for MAE; and 280 W, 50% duty cycle, and 7.5 min extraction for USAE. SHLE reported better extraction efficiencies as compared to the other two approaches, supporting the utility of SHLE for scaling-up the process. The extracts were dried in a rotary evaporator, reconstituted in 5 mL of methanol, and finally subjected to liquid-liquid extraction with n-hexane to remove nonpolar compounds that could complicate chromatographic separation. The methanolic fractions were analyzed by both LC-DAD and LC-TOF/MS, and the differences in composition according to the extraction conditions were studied. Compounds usually present in commercial wood extracts (mainly benzoic and hydroxycinnamic acids and aldehydes) were detected in vine-shoot extracts.     

Polyphenolic content in different plant parts of soy cultivars grown under natural conditions

Roots, cotyledons, leaves, stems, pods, and seeds of three soy cultivars were analyzed for their content of isoflavones, flavonols, coumarins, and phenolic acid derivatives with three samplings during a three-month period. The extracts were analyzed by HPLC/DAD and HPLC/MS, allowing us to confirm the presence of daidzein and genistein derivatives as the major isoflavones and to characterize coumarins, most flavonols and phenolic acid derivatives. Seeds exhibited the highest content of isoflavones: 12.61 g/kg of dry weight (DW) in cv. Emiliana; 8.97 g/kg of DW in cv. Elvir; 4.49 g/kg of DW in cv. Kure, and roots are the only part with coumarins, ranging from 4.08 g/kg of DW (cv. Emiliana) to 1.29 g/kg of DW (cv. Elvir) for the longest sampling period. Leaves, pods, and stems have flavonols, and in particular leaves showed: 7.28 g/kg of DW in cv. Emiliana; 6.57 g/kg of DW in cv. Elvir; 7.08 g/kg of DW in cv. Kure. The high content of isoflavones found in the seeds could be ascribed to the natural conditions under which the soy plants were grown.     

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.     

In vivo aroma release of milk gels of different hardnesses: inter-individual differences and their consequences on aroma perception

The effect of textural modifications of solid milk gels on in vivo aroma release and aroma perception was investigated with a panel of 14 subjects. Great inter-individual differences were observed on aroma-release data, and the consequences of these differences on aroma perception were studied. From a hierarchical cluster analysis performed with several parameters extracted from release curves, the subjects were gathered into two groups, and a specific aroma-release profile was identified for each one. Then, by using a sensory profile, we showed that the intensity of the aroma perception was dependent on the release profile presented by the panelist. Second, we observed that, during the chewing phase, the aroma was perceived as more intense for the firmer gel and for panelists for whom the aroma release begins during the chewing of the product.     

Olfactory and quantitative analysis of aroma compounds in elder flower (Sambucus nigra L.) drink processed from five cultivars

Fresh elder flowers (Sambucus nigra L.) were extracted with an aqueous solution containing sucrose, peeled lemon slices, tartaric acid, and sodium benzoate to make elder flower syrup. Aroma compounds emitted from the elder flower syrup were collected by the dynamic headspace technique and analyzed by GC-FID and GC-MS. A total of 59 compounds were identified, 18 of which have not previously been detected in elder flower products. The concentrations of the identified volatiles were measured in five elder cultivars, Allesoe, Donau, Sambu, Sampo, and Samyl, and significant differences were detected among cultivars in the concentration levels of 48 compounds. The odor of the volatiles was evaluated by the GC-sniffing technique. cis-Rose oxide, nerol oxide, hotrienol, and nonanal contributed to the characteristic elder flower odor, whereas linalool, alpha-terpineol, 4-methyl-3-penten-2-one, and (Z)-beta-ocimene contributed with floral notes. Fruity odors were associated with pentanal, heptanal, and beta-damascenone. Fresh and grassy odors were primarily correlated with hexanal, hexanol, and (Z)-3-hexenol.     

Characterization of the key aroma compounds in rape honey by means of the molecular sensory science concept

By application of aroma extract dilution analysis (AEDA) on the volatile fraction isolated by solvent extraction and solvent-assisted flavor evaporation (SAFE) from unifloral rape honey harvested in July 2009, 28 odor-active areas could be detected within a flavor dilution factor (FD) range of 4-2048. The highest FD factors were found for (E)-β-damascenone (cooked apple-like), phenylacetic acid (honey-like), 4-methoxybenzaldehyde (aniseed-like), 3-phenylpropanoic acid (flowery, waxy), and 2-methoxy-4-vinylphenol (clove-like). Twenty-three odorants were then quantitated by application of stable isotope dilution assays, and their odor activity values (OAV, ratio of concentration to odor threshold) were calculated on the basis of newly determined odor thresholds in an aqueous fructose-glucose solution. The highest OAVs were calculated for (E)-β-damascenone, 3-phenylpropanoic acid, phenylacetic acid, dimethyl trisulfide, and phenylacetaldehyde. Quantitative measurements on a rape honey produced in 2011 confirmed the results. A model mixture containing the 12 odorants showing an OAV ≥ 1 at the same concentrations as they occurred in the rape honey was able to mimick the aroma impression of the original honey. The characterization of the key odorants in rape flowers from the same field suggested 3-phenylpropanoic acid, phenylacetic acid, and three further odorants to be transferred via the bees into the honey.     

Characterization of the key aroma compounds in the beverage prepared from Darjeeling black tea: quantitative differences between tea leaves and infusion

By application of the aroma extract dilution analysis on the volatile fraction isolated from a black tea infusion (Darjeeling Gold Selection), vanillin (vanilla-like), 4-hydroxy-2,5-dimethyl-3(2H)-furanone (caramel), 2-phenylethanol (flowery), and (E,E,Z)-2,4,6-nonatrienal (oat-flake-like) were identified with the highest flavor dilution (FD) factors among the 24 odor-active compounds detected in the FD factor range of 4-128. Quantitative measurements performed by means of stable isotope dilution assays and a calculation of odor activity values (OAVs; ratio of concentration to odor threshold in water) revealed, in particular, the previously unknown tea constituent (E,E,Z)-2,4,6-nonatrienal as a key odorant in the infusion and confirmed the important role of linalool and geraniol for the tea aroma. An aroma recombinate performed by the 18 odorants for which OAVs > 1 were determined in their "natural" concentrations matched the overall aroma of the tea beverage. In the black tea leaves, a total of 42 odorants were identified, most of which were identical with those in the beverage prepared thereof. However, quantitative measurements indicated that, in particular, geraniol, but also eight further odorants were significantly increased in the infusion as compared to their concentration in the leaves.