Shu Kaneko

Studies on the key aroma compounds in raw (unheated) and heated Japanese soy sauce.

An investigation using the aroma extract dilution analysis (AEDA) technique of the aroma concentrate from a raw Japanese soy sauce and the heated soy sauce revealed 40 key aroma compounds including 7 newly identified compounds. Among them, 5(or 2)-ethyl-4-hydroxy-2(or 5)-methyl-3(2H)-furanone and 3-hydroxy-4,5-dimethyl-2(5H)-furanone exhibited the highest flavor dilution (FD) factor of 2048, followed by 3-(methylthio)propanal, 4-ethyl-2-methoxyphenol, and 4-hydroxy-2,5-dimethyl-3(2H)-furanone having FD factors from 128 to 512 in the raw soy sauce. Furthermore, comparative AEDAs, a quantitative analysis, and a sensory analysis demonstrated that whereas most of the key aroma compounds in the raw soy sauce were common in the heated soy sauce, some of the Strecker aldehydes and 4-vinylphenols contributed less to the raw soy sauce aroma. The model decarboxylation reactions of the phenolic acids during heating of the raw soy sauce revealed that although all reactions resulted in low yields, the hydroxycinnamic acid derivatives were much more reactive than the hydroxybenzoic acid derivatives due to the stable reaction intermediates. Besides the quantitative analyses of the soy sauces, the estimation of the reaction yields of the phenolic compounds in the heated soy sauce revealed that although only the 4-vinylphenols increased during heating of the raw soy sauce, they might not mainly be formed as decarboxylation products from the corresponding hydroxycinnamic acids but from the other proposed precursors, such as lignin, shakuchirin, and esters with arabinoxylan.

Isolation and Identification of the Umami Enhancing Compounds in Japanese Soy Sauce

To clarify the key compounds that account for the umami taste of soy sauce, a typical Japanese soy sauce, Koikuchi Shoyu, was separated by preparative chromatography, and the umami enhancing fractions were screened on the basis of an umami intensity of a 6.0 mM monosodium L-glutamate (MSG) solution. Liquid chromatography-time of flight mass spectrometry (LC-TOFMS), 1D/2D nuclear magnetic resonance spectroscopy (NMR) studies of the umami enhancing fractions led to the identification of N-(1-deoxy-D-fructos-1-yl)pyroglutamic acid (Fru-pGlu), N-(1-deoxy-D-fructos-1-yl)valine (Fru-Val), N-(1-deoxy-D-fructos-1-yl)methionine (Fru-Met), pyroglutamylglutamine (pGlu-Gln), and pyroglutamylglycine (pGlu-Gly). Although all the compounds identified were at sub-threshold concentrations in the soy sauce, a taste reconstitution experiment revealed that they contributed part of the umami taste of the soy sauce.

Identification and Characterization of Volatile Components Causing the Characteristic Flavor in Miso (Japanese Fermented Soybean Paste) and Heat-Processed Miso Products

The aroma concentrates of two types of raw miso (traditional Japanese fermented soybean paste) were prepared by combining solid phase extraction (SPE) and solvent-assisted flavor evaporation (SAFE) techniques. The aroma extract dilution analysis (AEDA) applied to the volatile fraction revealed 39 odor-active peaks with FD factors between 4(1) and 4(8). Among the perceived odorants, 32 odorants were identified or tentatively identified from the 39 odor-active peaks, and the newly identified odorants for the miso were half of them. Furthermore, by comparison of the FD factors between the raw miso and heat-processed miso, it was found that one increasing odorant (methional) and three decreasing odorants (1-octen-3-one, (Z)-1,5-octadien-3-one, and trans-4,5-epoxy-(E)-2-decenal) contributed to the flavor change during the heat processing. This finding suggested that the flavor change in the raw miso during heat processing is attributed to relatively few odorant changes. In addition, it was assumed that the amino acids included in the miso have a significant influence on the remarkable disappearance of the three decreasing odorants.

Key aroma compounds in roasted in-shell peanuts.

An investigation by using an aroma extract dilution analysis (AEDA) of the aroma concentrates made from freshly roasted in-shell peanuts and stored peanuts revealed a total of 43 key aroma compounds, including 8 newly identified compounds in peanuts. Among them, 2-isobutyl-3-methoxypyrazine, exhibiting an earthy note, and 4-hydroxy-2,5-dimethyl-3(2H)-furanone, exhibiting a caramel-like note, were detected with the highest flavor dilution (FD) factor of 4096 in the fresh peanuts, followed by 3,5-dimethyl-2-ethylpyrazine, exhibiting a nutty note, as having the next highest FD factor of 1024. A quantitative analysis of the key aroma compounds having high FD factors in the fresh peanuts and stored peanuts revealed that 2-methyl-3-furanthiol, 2-acetyl-1-pyrroline, 2-propionyl-1-pyrroline, and 3,5-dimethyl-2-vinylpyrazine significantly decreased during storage, while methyl 2-methyl-3-furyl disulfide, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, and 2-methoxy-4-vinylphenol significantly increased. The sensory experiments revealed that the fresh peanuts presented strong roasty/meaty, popcorn-like, and nutty notes, as well as moderate spicy/burnt and caramel-like notes, whereas the stored peanuts presented significantly weak roasty/meaty and popcorn-like notes and a significantly strong spicy/burnt note. Based on the comparative AEDAs, the quantitative analysis, and the sensory analysis, it was concluded that the freshly roasted peanut aroma comprised the significant contributions of 2-methyl-3-furanthiol exhibiting a roasty/meaty note, and of 2-acetyl-1-pyrroline and 2-propionyl-1-pyrroline exhibiting a popcorn-like note, and the lesser contribution of 2-methoxy-4-vinylphenol exhibiting a spicy/burnt note. In particular, 2-methyl-3-furanthiol, which was only detected in the freshly roasted peanut aroma concentrate, might be an essential component describing the freshness of the roasted peanut aroma by its diffusive roasty/meaty note.

Aroma compounds in Japanese sweet rice wine (Mirin) screened by aroma extract dilution analysis (AEDA)

Thirty-nine key aroma compounds were newly identified or tentatively identified in the aroma concentrate of Japanese sweet rice wine (Mirin) by an aroma extract dilution analysis technique based on the 68 detected peaks. Among them, 3-(methylthio)propanal, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, 3-methylbutanoic acid, 2-methylbutanoic acid, and 2-methoxy-4-vinylphenol were detected with the highest FD factors in this study.

Sensory and structural characterisation of an umami enhancing compound in green tea (mat-cha)

Aimed at defining the key components for the umami taste of mat-cha a series of analysis were carried out on freshly prepared samples. The analyses included a bioactivity-guided fractionation using solvent extraction, solvent precipitation, preparative chromatographic separations and human psychophysical experiments. The LC-MS/MS and 1D/2D-NMR studies on isolated fractions led to the identification of (1R,2R,3R,5S)-5-carboxy-2,3,5-trihydroxy-cyclohexyl 3,4,5-trihydroxybenzoate known as theogallin, an umami enhancing compound in mat-cha. Sensory analysis showed that this compound can increase the umami intensity of sodium L-glutamate proportionally.

Potent Odorants of Characteristic Floral/Sweet Odor in Chinese Chrysanthemum Flower Tea Infusion

An investigation using the aroma extract dilution analysis (AEDA) technique applied to the aroma concentrates prepared from the tea infusions of two different types of Chinese chrysanthemum flowers (flower buds, blooming flowers) revealed that 29 aroma peaks were detected in the aroma concentrates, and 17 compounds were newly identified or tentatively identified in the chrysanthemum flower tea. AEDA also revealed that the aroma peaks having high flavor dilution factors mainly consisted of a floral/sweet note in addition to metallic and phenol-like/spicy notes. Among them, four aroma peaks having a floral/sweet were identified as verbenone, ethyl 3-phenylpropanoate, propyl 3-phenylpropanoate, and ethyl cinnamate, and a semiquantitative analysis revealed that the flower buds were rich in these compounds. Furthermore, a chiral analysis revealed that (-)-verbenone existed in both flowers at a 3 times higher concentration than (+)-verbenone. Additionally, because the detection threshold of (-)-verbenone was lower than that of the (+)-verbenone, it is concluded that the (-)-isomer was a main contributor of the aroma peak of verbenone in the chrysanthemum flower tea.