PEPTIDE COMPOUNDS FOR FLAVOR MODULATING
20240315296 ยท 2024-09-26
Assignee
Inventors
- Ji Hyun Kang (Seoul, KR)
- Mikyoung CHAE (Seoul, KR)
- Eunyong LEE (Seoul, KR)
- Thomas HOFMANN (Freising, DE)
- Corinna DAWID (Freising, DE)
- Verena Karolin MITTERMEIER KLESSINGER (Freising, DE)
- Manon JUENGER (Freising, DE)
Cpc classification
A23L27/31
HUMAN NECESSITIES
International classification
A23L27/00
HUMAN NECESSITIES
Abstract
The present application investigates a new flavor modulating compound having a flavor modulating effect in Korean food which is based on fermentation techniques, and thus shows excellent effects of modulating the flavor of food.
Claims
1. A method for flavor modulating, comprising applying a composition for flavor modulating to a food, wherein the composition comprises: (1) (i) at least one arginyl-dipeptide selected from the group consisting of Arg-Ala, Ala-Arg, Arg-Asp, Asp-Arg, Arg-Gln, Gln-Arg, Arg-Gly, Gly-Arg, Arg-Leu, Leu-Arg, Arg-Lys, Lys-Arg, Arg-Pro, Pro-Arg, Arg-Ser, Ser-Arg, Arg-Val, and Val-Arg, (ii) at least one prolyl-dipeptide selected from the group consisting of Pro-Ala, Ala-Pro, Pro-Arg, Arg-Pro, Pro-Asn, Asn-Pro, Pro-Asp, Asp-Pro, Pro-Cys, Cys-Pro, Pro-Gln, Gln-Pro, Pro-Gly, Gly-Pro, Pro-His, His-Pro, Pro-Ile, Ile-Pro, Pro-Leu, Leu-Pro, Pro-Lys, Lys-Pro, Pro-Met, Met-Pro, Pro-Phe, Phe-Pro, Pro-Pro, Pro-Ser, Ser-Pro, Pro-Thr, Thr-Pro, Pro-Trp, Trp-Pro, Pro-Val, Val-Pro, Pro-Tyr, and Tyr-Pro, or (iii) a combination thereof; (2) at least one selected from long chain peptides comprising amino acid sequences of ALDPLPT (SEQ ID NO: 1), DGFP (SEQ ID NO: 2), DGML (SEQ ID NO: 3), DNEDTP (SEQ ID NO: 4), DTDEPN (SEQ ID NO: 5), EEL (SEQ ID NO: 6), EEV (SEQ ID NO: 7), EEY (SEQ ID NO: 8), ESLPALP (SEQ ID NO: 9), EVGYGY (SEQ ID NO: 10), LDYY (SEQ ID NO: 11), LPPP (SEQ ID NO: 12), MTTFTW (SEQ ID NO: 13), PPPP (SEQ ID NO: 14), PPPPP (SEQ ID NO: 15), DAPL (SEQ ID NO: 16), DVL (SEQ ID NO: 17), GGPF (SEQ ID NO: 18), GNPF (SEQ ID NO: 19), EVLK (SEQ ID NO: 20), FADSL (SEQ ID NO: 21), LAL (SEQ ID NO: 22), LLL (SEQ ID NO: 23), LLQ (SEQ ID NO: 24), LPL (SEQ ID NO: 25), PLL (SEQ ID NO: 26), TPL (SEQ ID NO: 27), and VLL (SEQ ID NO: 28); or (3) a combination thereof.
2. The method according to claim 1, wherein the composition comprises: (1) (i) at least one selected from arginyl-dipeptides consisting of Arg-Gly and Gly-Arg, (ii) at least one selected from prolyl-dipeptides consisting of Pro-Pro, Pro-Glu, Pro-Ala, Pro-Lys, Pro-Ser, Pro-Val, Arg-Pro, Lys-Pro, Ser-Pro, and Val-Pro, (iii) or a combination thereof; (2) at least one selected from long chain peptides comprising amino acid sequences of ALDPLPT (SEQ ID NO: 1), DGFP (SEQ ID NO: 2), DGML (SEQ ID NO: 3), DNEDTP (SEQ ID NO: 4), DTDEPN (SEQ ID NO: 5), EEL (SEQ ID NO: 6), EEV (SEQ ID NO: 7), EEY (SEQ ID NO: 8), ESLPALP (SEQ ID NO: 9), EVGYGY (SEQ ID NO: 10), LDYY (SEQ ID NO: 11), LPPP (SEQ ID NO: 12), MTTFTW (SEQ ID NO: 13), PPPP (SEQ ID NO: 14), PPPPP (SEQ ID NO: 15), DAPL (SEQ ID NO: 16), DVL (SEQ ID NO: 17), GGPF (SEQ ID NO: 18), GNPF (SEQ ID NO: 19), EVLK (SEQ ID NO: 20), FADSL (SEQ ID NO: 21), LAL (SEQ ID NO: 22), LLL (SEQ ID NO: 23), LLQ (SEQ ID NO: 24), LPL (SEQ ID NO: 25), PLL (SEQ ID NO: 26), TPL (SEQ ID NO: 27), and VLL (SEQ ID NO: 28); or (3) a combination thereof.
3. The method according to claim 1, wherein the composition comprises: (1) at least one selected from dipeptides consisting of Pro-Pro, Pro-Val, Arg-Pro, Ser-Pro, Val-Pro, Arg-Gly, and Gly-Arg; (2) at least one selected from long chain peptides comprising amino acid sequences of DGML (SEQ ID NO: 3), DNEDTP (SEQ ID NO: 4), LPPP (SEQ ID NO: 12), PPPP (SEQ ID NO: 14), PPPPP (SEQ ID NO: 15), DAPL (SEQ ID NO: 16), DVL (SEQ ID NO: 17), GGPF (SEQ ID NO: 18), LAL (SEQ ID NO: 22), LLL (SEQ ID NO: 23), PLL (SEQ ID NO: 26), and TPL (SEQ ID NO: 27); or (3) a combination thereof.
4. The method according to claim 1, wherein the composition comprises: (1) at least one selected from dipeptides consisting of Pro-Glu, Pro-Ala, Pro-Lys, Pro-Ser, and Lys-Pro; (2) at least one selected from long chain peptides comprising amino acid sequences of ALDPLPT (SEQ ID NO: 1), DGFP (SEQ ID NO: 2), EEL (SEQ ID NO: 6), EEV (SEQ ID NO: 7), EEY (SEQ ID NO: 8), ESLPALP (SEQ ID NO: 9), EVGYGY (SEQ ID NO: 10), LDYY (SEQ ID NO: 11), MTTFTW (SEQ ID NO: 13), EVLK (SEQ ID NO: 20), FADSL (SEQ ID NO: 21), LLQ (SEQ ID NO: 24), LPL (SEQ ID NO: 25), and VLL (SEQ ID NO: 28); or (3) a combination thereof.
5. The method according to claim 1, wherein the composition comprises: (1) (1-i) at least one selected from dipeptides consisting of Pro-Pro, Pro-Glu, Pro-Ser, Pro-Val, Arg-Pro, Ser-Pro, Val-Pro, Arg-Gly, and Gly-Arg; (1-ii) at least one selected from dipeptides consisting of Pro-Pro, Pro-Ala, Pro-Lys, Pro-Val, Arg-Pro, Ser-Pro, Val-Pro, Arg-Gly, and Gly-Arg; or (1-iii) at least one selected from dipeptides consisting of Pro-Pro, Pro-Ala, Pro-Lys, Pro-Ser, Pro-Val, Arg-Pro, Ser-Pro, Val-Pro, Arg-Gly, and Gly-Arg; (2) (2-i) at least one selected from long chain peptides comprising amino acids of ALDPLPT (SEQ ID NO: 1), DGML (SEQ ID NO: 3), DNEDTP (SEQ ID NO: 4), EEL (SEQ ID NO: 6), EEV (SEQ ID NO: 7), EEY (SEQ ID NO: 8), ESLPALP (SEQ ID NO: 9), EVGYGY (SEQ ID NO: 10), LDYY (SEQ ID NO: 11), LPPP (SEQ ID NO: 12), MTTFTW (SEQ ID NO: 13), PPPP (SEQ ID NO: 14), PPPPP (SEQ ID NO: 15), DAPL (SEQ ID NO: 16), DVL (SEQ ID NO: 17), GGPF (SEQ ID NO: 18), LAL (SEQ ID NO: 22), LLL (SEQ ID NO: 23), LLQ (SEQ ID NO: 24), PLL (SEQ ID NO: 26), and TPL (SEQ ID NO: 27); (2-ii) at least one selected from long chain peptides comprising amino acids of ALDPLPT (SEQ ID NO: 1), DGFP (SEQ ID NO: 2), DGML (SEQ ID NO: 3), DNEDTP (SEQ ID NO: 4), EEL (SEQ ID NO: 6), EEV (SEQ ID NO: 7), EEY (SEQ ID NO: 8), EVGYGY (SEQ ID NO: 10), LDYY (SEQ ID NO: 11), LPPP (SEQ ID NO: 12), MTTFTW (SEQ ID NO: 13), PPPP (SEQ ID NO: 14), PPPPP (SEQ ID NO: 15), DAPL (SEQ ID NO: 16), DVL (SEQ ID NO: 17), GGPF (SEQ ID NO: 18), LAL (SEQ ID NO: 22), LLL (SEQ ID NO: 23), PLL (SEQ ID NO: 26), and TPL (SEQ ID NO: 27), (2-iii) at least one selected from long chain peptides comprising amino acids of DGML (SEQ ID NO: 3), DNEDTP (SEQ ID NO: 4), LPPP (SEQ ID NO: 12), PPPP (SEQ ID NO: 14), PPPPP (SEQ ID NO: 15), DAPL (SEQ ID NO: 16), DVL (SEQ ID NO: 17), GGPF (SEQ ID NO: 18), EVLK (SEQ ID NO: 20), LAL (SEQ ID NO: 22), LLL (SEQ ID NO: 23), LLQ (SEQ ID NO: 24), LPL (SEQ ID NO: 25), PLL (SEQ ID NO: 26), TPL (SEQ ID NO: 27), and VLL (SEQ ID NO: 28); or (2-iv) at least one selected from long chain peptides comprising amino acids of DGFP (SEQ ID NO: 2), DGML (SEQ ID NO: 3), DNEDTP (SEQ ID NO: 4), LDYY (SEQ ID NO: 11), LPPP (SEQ ID NO: 12), PPPP (SEQ ID NO: 14), PPPPP (SEQ ID NO: 15), DAPL (SEQ ID NO: 16), DVL (SEQ ID NO: 17), GGPF (SEQ ID NO: 18), EVLK (SEQ ID NO: 20), FADSL (SEQ ID NO: 21), LAL (SEQ ID NO: 22), LLL (SEQ ID NO: 23), LLQ (SEQ ID NO: 24), LPL (SEQ ID NO: 25), PLL (SEQ ID NO: 26), TPL (SEQ ID NO: 27), and VLL (SEQ ID NO: 28); or (3) a combination thereof.
6. The method according to claim 1, wherein the composition further comprises a glutamyl dipeptide.
7. The method according to claim 6, wherein the composition further comprises at least one selected from glutamyl-dipeptides consisting of ?-Glu-Gly, ?-Glu-Glu, ?-Glu-Gln, ?-Glu-Leu, ?-Glu-Met, ?-Glu-His, ?-Glu-Ala, pyroGlu-Pro, pyroGlu-Glu, pyroGlu-Gln, and pyroGlu-Ser.
8. The method according to claim 6, wherein the composition further comprises at least one selected from dipeptides consisting of ?-Glu-Gly, ?-Glu-Leu, ?-Glu-Met, ?-Glu-His, pyroGlu-Glu, and pyroGlu-Gln.
9. The method according to claim 8, wherein the composition further comprises at least one selected from dipeptides consisting of ?-Glu-Glu, ?-Glu-Gln, ?-Glu-Ala, pyroGlu-Pro, and pyroGlu-Ser.
10. The method according to claim 6, wherein the composition comprises: (i) comprises at least one selected from the group consisting of ?-Glu-Gly, ?-Glu-Glu, ?-Glu-Gln, ?-Glu-Leu, ?-Glu-Met, ?-Glu-His, ?-Glu-Ala, pyroGlu-Pro, pyroGlu-Glu, and pyroGlu-Gln, or (ii) comprises at least one selected from the group consisting of ?-Glu-Gly, ?-Glu-Leu, ?-Glu-Met, ?-Glu-His, pyroGlu-Glu, pyroGlu-Gln, and pyroGlu-Ser.
11. The method according to claim 6, wherein the composition comprises: (1) Pro-Pro, Pro-Glu, Pro-Ser, Pro-Val, Arg-Pro, Ser-Pro, Val-Pro, Arg-Gly, Gly-Arg, ?-Glu-Gly, ?-Glu-Glu, ?-Glu-Gln, ?-Glu-Leu, ?-Glu-Met, ?-Glu-His, ?-Glu-Ala, pyroGlu-Pro, pyroGlu-Glu, pyroGlu-Gln, long chain peptides comprising amino acid sequences of ALDPLPT (SEQ ID NO: 1), DGML (SEQ ID NO: 3), DNEDTP (SEQ ID NO: 4), EEL (SEQ ID NO: 6), EEV (SEQ ID NO: 7), EEY (SEQ ID NO: 8), ESLPALP (SEQ ID NO: 9), EVGYGY (SEQ ID NO: 10), LDYY (SEQ ID NO: 11), LPPP (SEQ ID NO: 12), MTTFTW (SEQ ID NO: 13), PPPP (SEQ ID NO: 14), PPPPP (SEQ ID NO: 15), DAPL (SEQ ID NO: 16), DVL (SEQ ID NO: 17), GGPF (SEQ ID NO: 18), LAL (SEQ ID NO: 22), LLL (SEQ ID NO: 23), LLQ (SEQ ID NO: 24), PLL (SEQ ID NO: 26), and TPL (SEQ ID NO: 27); (2) Pro-Pro, Pro-Glu, Pro-Ser, Pro-Val, Arg-Pro, Ser-Pro, Val-Pro, Arg-Gly, Gly-Arg, ?-Glu-Gly, ?-Glu-Glu, ?-Glu-Gln, ?-Glu-Leu, ?-Glu-Met, ?-Glu-His, ?-Glu-Ala, pyroGlu-Pro, pyroGlu-Glu, pyroGlu-Gln, long chain peptides comprising amino acid sequences of ALDPLPT (SEQ ID NO: 1), DGFP (SEQ ID NO: 2), DGML (SEQ ID NO: 3), DNEDTP (SEQ ID NO: 4), EEL (SEQ ID NO: 6), EEV (SEQ ID NO: 7), EEY (SEQ ID NO: 8), EVGYGY (SEQ ID NO: 10), LDYY (SEQ ID NO: 11), LPPP (SEQ ID NO: 12), MTTFTW (SEQ ID NO: 13), PPPP (SEQ ID NO: 14), PPPPP (SEQ ID NO: 15), DAPL (SEQ ID NO: 16), DVL (SEQ ID NO: 17), GGPF (SEQ ID NO: 18), LAL (SEQ ID NO: 22), LLL (SEQ ID NO: 23), PLL (SEQ ID NO: 26), and TPL (SEQ ID NO: 27); (3) Pro-Pro, Pro-Ala, Pro-Lys, Pro-Ser, Pro-Val, Arg-Pro, Ser-Pro, Val-Pro, Arg-Gly, Gly-Arg, ?-Glu-Gly, ?-Glu-Leu, ?-Glu-Met, ?-Glu-His, pyroGlu-Glu, pyroGlu-GIn, long chain peptides comprising amino acid sequences of DGML (SEQ ID NO: 3), DNEDTP (SEQ ID NO: 4), LPPP (SEQ ID NO: 12), PPPP (SEQ ID NO: 14), PPPPP (SEQ ID NO: 15), DAPL (SEQ ID NO: 16), DVL (SEQ ID NO: 17), GGPF (SEQ ID NO: 18), EVLK (SEQ ID NO: 20), LAL (SEQ ID NO: 22), LLL (SEQ ID NO: 23), LLQ (SEQ ID NO: 24), LPL (SEQ ID NO: 25), PLL (SEQ ID NO: 26), TPL (SEQ ID NO: 27), and VLL (SEQ ID NO: 28); or (4) Pro-Pro, Pro-Ala, Pro-Lys, Pro-Ser, Pro-Val, Arg-Pro, Ser-Pro, Val-Pro, Arg-Gly, Gly-Arg, ?-Glu-Gly, ?-Glu-Leu, ?-Glu-Met, ?-Glu-His, pyroGlu-Glu, pyroGlu-Gln, pyroGlu-Ser, long chain peptides comprising amino acid sequences of DGFP (SEQ ID NO: 2), DGML (SEQ ID NO: 3), DNEDTP (SEQ ID NO: 4), LDYY (SEQ ID NO: 11), LPPP (SEQ ID NO: 12), PPPP (SEQ ID NO: 14), PPPPP (SEQ ID NO: 15), DAPL (SEQ ID NO: 16), DVL (SEQ ID NO: 17), GGPF (SEQ ID NO: 18), EVLK (SEQ ID NO: 20), FADSL (SEQ ID NO: 21), LAL (SEQ ID NO: 22), LLL (SEQ ID NO: 23), LLQ (SEQ ID NO: 24), LPL (SEQ ID NO: 25), PLL (SEQ ID NO: 26), TPL (SEQ ID NO: 27), and VLL (SEQ ID NO: 28).
12. The method according to claim 1, comprising applying the composition for flavor modulating to fermented food.
13. The method according to claim 1, comprising applying the composition for flavor modulating to a fermented rice paste, a fermented soybean paste, a fermented wheat paste, soy sauce, kimchi, soybean paste, or fish sauce.
14. (canceled)
15. (canceled)
Description
BRIEF DESCRIPTION OF THE DRAWINGS
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MODE FOR INVENTION
[0186] Hereinafter, the present invention will be described in more detail by the following examples. However, they are intended to illustrate the present invention only, but the scope of the present invention is not limited by these examples.
EXAMPLE 1. Sensory Evaluation of Various Korean Fermented Foods
[0187] Sensory evaluation was conducted by preparing samples of 25 kinds of various Korean fermented foods (3 kinds of fermented rice paste (FRP), 5 kinds of fermented soybean paste (FSP), 2 kinds of fermented wheat paste (FWP), 6 kinds of fish sauce (FS), 1 kind of liquid kimchi (LK), 6 kinds of soy sauce (SS), 2 kinds of yeast extract (YE)). The food samples were acquired from CJ CheilJedang, or used by directly preparing.
[0188] For objective taste evaluation, all the samples were under a desalination process, and the schematic diagram of the desalination process and method for preparing samples for sensory evaluation is as shown in
[0189] Specifically, the samples were homogenized, and then extracted with hot water of 80?100? C., and then lyophilized. After that, after desalination with methanol solution of 70%(v/v), the solution was removed and lyophilized again to prepare desalinated samples for sensory evaluation.
[0190] All the prepared samples for sensory evaluation were prepared as liquid samples at the same concentration (that is, mixed at a weight ratio of sample:water=1:3), and the sensory evaluation condition was same as Table 15 below.
TABLE-US-00015 TABLE 15 Sample 25 Panel 27 people (23~31-aged male/female, panels trained in sensory evaluation for at least 2 years) Sensory evaluation 6 taste attributes (sour taste, salty taste, sweet item/scale taste, bitter taste, umami taste, kokumi taste)/ 5-point scale Sensory evaluation Bottle water (Evian, low mineralization, 500 mg/L) standard product sucrose (50 mmol/L) lactic acid (20 mmol/L) NaCl (12 mmol/L) caffeine (1 mmol/L) sodium L-glutamate (8 mmol/L, pH 5.7) model broth* spiked with glutathione (5 mmol/L) Sample preparation pH 5.7. sample:water = 1:3 (weight ratio) Note Using a nose clamp to minimize an effect by scent *model broth: NaCl 2.9 g/L, MSG 1.9 g/L, YE (Gistex XII LS) 2.1 g/L, Maltodextrin 6.4 g/L
[0191] The sensory evaluation result of 25 kinds of the samples progressed by the above method was shown in Table 16 below. Six of the taste attributes (sweet taste, sour taste, bitter taste, kokumi taste, salty taste, umami taste) of each sample were shown with a 5-point scale.
TABLE-US-00016 TABLE 16 Sweet Sour Bitter Kokumi Salty Umami No. Sample taste taste taste taste taste taste 1 SS1 0.8824 0.9014 1.409 1.14 2.913 2.006 2 SS2 0.7591 0.7181 1.706 1.326 3.016 2.239 3 SS3 0.8136 0.8062 2.104 1.329 2.442 2.23 4 SS4 1.08 1.105 1.402 1.437 2.909 2.343 5 SS5 0.803 1.252 1.932 1.637 3.159 2.569 6 SS6 1.226 1.202 1.719 1.654 2.906 2.699 7 FS1 0.6134 1.424 2.394 0.9387 2.898 1.696 8 FS2 0.7519 2.228 0.9752 1.354 2.771 1.811 9 FS3 0.8827 1.401 2.252 1.416 2.628 1.719 10 FS4 0.8557 1.244 1.457 1.17 2.369 1.655 11 FS5 0.7807 1.088 1.119 1.236 2.36 1.846 12 FS6 0.8213 0.9848 1.135 1.524 2.866 2.305 13 FSP1 0.4432 1.041 0.1981 0.4277 2.205 1.027 14 FSP2 0.6391 1.195 0.8022 0.7485 2.73 1.502 15 FSP3 0.4391 1.045 2.161 0.6694 2.172 1.377 16 FSP4 0.9819 0.9463 0.6738 0.8334 1.787 1.53 17 FSP5 1.253 0.788 0.628 1.042 2.128 1.805 18 FWP1 1.15 1.099 0.198 0.9664 2.208 1.798 19 FWP2 1.356 0.7987 0.2547 1.11 1.668 1.664 20 FRP1 1.898 0.6261 0.1501 1.17 1.776 1.573 21 FRP2 1.753 0.8951 0.4055 1.357 3.021 1.723 22 FRP3 2.223 1.06 0.2298 1.281 2.821 2 23 LK1 1.431 0.6325 0.5127 0.8738 1.156 1.182 24 YE1 1.199 1.175 0.9413 1.527 1.449 2.324 25 YE2 0.9094 1.136 0.6627 1.688 2.109 2.539
EXAMPLE 2. Sensory Evaluation of Fractions of Korean Fermented Foods
Sensory Evaluation
[0192] In order to identify unknown taste components, which was not comprised in Korean fermented foods, sensory evaluation for the fractions of Korean fermented foods was performed.
[0193] Sensory evaluation of the fractions is an experiment of confirming the minimal cognitive concentration of taste by continuously diluting fractions of food samples, and this experiment is known as Taste Dilution Analysis (TDA), Comparative Taste Dilution Analysis (cTDA) (J. Agric. Food Chem. 2003, 51, 1035-1041). The fractionized samples were pretreated using SPE (Solid Phase Extraction), and recombinants using basic taste components were used during dilution. For each sample, all the 6 sensory evaluation items were evaluated, and it was diluted at a ratio of 1:2 (volume ratio) in the basic concentration sample during dilution. The initial concentration began at 1 mmol/L, and in order to confirm the minimal cognitive concentration, TDA, cTDA methods were used. All the samples were corrected using formic acid 1%(v/v) solution at pH 5.4, and they were diluted at a ratio of 1:2 in stages.
Quantitative Analysis
[0194] Quantitative analysis of the taste components comprised in the samples of 25 kinds of the Korean fermented foods of Example 1 was performed. Items of the taste components were ions (cations, anions), free amino acids, nucleic acids, organic acids, saccharides (monosaccharides, disaccharides), and dipeptides. For all the samples for quantitative analysis, the desalination process was progressed and lyophilized by the same method as Example 1.
[0195] Ion (cation, anion) analysis was analyzed based on the external standard product using high performance ion chromatography (HP-IC).
[0196] The free amino acids and nucleic acids, and dipeptides were analyzed using liquid chromatography-mass/mass spectrometer (LC-MS/MS), and all were under quantitative analysis using an isotopically labeled internal standard substance.
[0197] Organic acids and saccharides were analyzed using internal analysis database using quantitative nuclear magnetic resonance spectroscopy (q-NMR).
[0198] Detailed analysis items and analysis equipment, conditions were described in Table 17 below.
TABLE-US-00017 TABLE 17 Analysis item Equipment Analysis condition Cations HP-IC Dionex lonPac CS19 Dionex ICS-2000 (250 ? 2.0 mm) 0.25 mL/min 2 mM methanesulfonic acid Anions HP-IC Dionex lonPac AS11-HC-4 ?m Dionex ICS-5000 (250 ? 2.0 mm) 0.015 mL/min 1 mM potassium hydroxide (KOH) Organic acids/ 500 MHz ultrashield plus Avance D.sub.2O saccharides III NMR Free amino API 4000 QTRAP mass XBridge Amide (2.1 ? 150 mm, acids spectrometer 5 ?m) acetonitrile/aqueous ammonium acetate (pH 3.0. 5 mmol/L) Nucleic acids API 4000 QTRAP system XBridge Amide column (2.1 ? 150 mm, 5 ?m) acetonitrile/ammonium acetate (pH 9.0. 5 mmol/L) Peptides API 4000 QTRAP mass Acquity UPLC BEH Amide column (Glutamyl) spectrometer (2.1 ? 150 mm, 1.7 ?m) acetonitrile/ammonium acetate (pH 2.0. 5 mmol/L)
[0199] The result of the taste component analysis result of the 25 samples was schematized and shown in
[0200] In other words,
EXAMPLE 3. Sensory Evaluation of Soy Sauce and Fermented Rice Paste Recombinant Samples
[0201] Using substances confirmed through the taste component quantitative analysis of the samples, recombinant samples for 2 kinds of soy sauce (SS) and 2 kinds of fermented rice paste (FRP) were prepared (soy sauce recombinant samples: SS5-BR, SS6-BR, fermented rice paste recombinant samples: FRP2-BR, FRP3-BR).
[0202] The taste component compositions of the recombinant samples were shown in Table 18 below. The unit was expressed by g, and the ratio of the taste components to the total weight of the recombinant samples was expressed as %(w/w) in parentheses.
TABLE-US-00018 TABLE 18 SS5-BR SS6-BR FRP2-BR FRP3-BR Glutamic acid 4.2 (12.84%) 4.5 (12.36%) 0.1 (0.64%) 0.1 (0.55%) Aspartic acid 0.7 (2.14%) 0.8 (2.20%) 0.07 (0.45%) 0.07 (0.38%) Glucose 3.9 (24.89%) 5.7 (31.20%) Alanine 3.3 (10.09%) 2.8 (7.69%) Valine 2.9 (8.87%) 3.7 (10.16%) Proline 2.7 (8.26%) 3.2 (8.79%) Leucine 4.4 (13.46%) 6.1 (16.76%) Isoleucine 3.1 (9.48%) 4.2 (11.54%) Sodium 8.1 (24.77%) 7.6 (20.88%) 10.7 (68.28%) 11.7 (64.04%) Potassium 3.1 (9.48%) 3.1 (8.52%) 0.7 (4.47%) 0.6 (3.28%) Magnesium 0.2 (0.61%) 0.4 (1.10%) 0.2 (1.28%) 0.1 (0.55%) Total 32.7 (100%).sup. 36.4 (100%).sup. 15.67 (100%) 18.27 (100%)
[0203] Sensory evaluation of 4 kinds of the recombinant samples was performed by the same method as Example 1, and the result of comparing the sensory evaluation result of the soy sauce samples (SS5, SS6) and fermented rice paste samples (FRP2, FRP3) of Example 1 and the sensory evaluation result of the recombinant samples was shown in
[0204] As could be confirmed in
[0205] Such a result indicates that another taste component other than the taste components comprised in the soy sauce and fermented rice paste recombinant samples is additionally required in order to embody the taste of the soy sauce and fermented rice paste samples.
EXAMPLE 4. Analysis of Taste Components in Soy Sauce and Fermented Rice Paste Samples I
[0206] As it was confirmed that the sensory evaluation results of the soy sauce and fermented rice paste samples were different in Example 3, an additional experiment to identify a substance having a special effect of umami taste modulating in the soy sauce and fermented rice paste samples was performed. After passing through a desalination process of 4 kinds of the soy sauce and fermented rice pastes samples (soy sauce samples: SS5, SS6 of Table 20, fermented rice paste samples: FRP2, FRP3 of Table 20), they were separated and fractionized using a chromatography method (Solid-Phase Extraction, SPE), and sensory characteristics were confirmed by each separated section. This chromatography can be performed using not only SPE but also various methods such as MPLC (Medium pressure liquid chromatography), FPLC (Fast protein liquid chromatography) and the like.
[0207] Specifically, the SPE chromatography was performed by the following process.
[0208] In order to activate the cartridge of SPE, methanol of 60?70 mL was flowed. After that, it was washed with distilled water 2?3 times, and then the prepared samples were loaded. After completing sample loading, all liquid was drained, and the samples were adsorbed to the cartridge and then extracted using an appropriate solvent. The solvent used in the present application was as follows, and methanol, ethanol and water were used at various composition ratios (v/v).
[0209] The experimental result of confirming separation/fractionization and taste characteristics for the soy sauce samples (SS5, SS6) was shown in
[0211] Taste components comprised in the obtained fractions of 4 kinds of the soy sauce and fermented rice paste samples were analyzed. In order to identify substances having an effect of modulating umami taste unknown in Korean fermented foods, a trace component analysis experiment was conducted for the fractions. For analysis of peptides comprised in the fractions, using LC-QTrap-MS, peptide analysis was performed. A specific experimental method was same as Table 19 below.
TABLE-US-00019 TABLE 19 Analysis item Equipment Analysis condition Peptide 6500 + Q-Trap ACQITY UPLC? BEH (Prolyl. Mass Amide 1.7 ?m (2.1 ? 100 mm Arginyl) Spectrometer 0.4 mL/min A: 5 mM NH4Ac-Puffer aq., pH 2 B: Acetonitrile/H2O (v/v, 95/5), 5 mM NH4Ac-Puffer, pH 2
[0212] As the result of peptide analysis, the main substances detected from the fraction were dipeptide compounds (prolyl peptides and arginyl peptides), and specifically, the detected dipeptide compounds were described in Table 20 below.
TABLE-US-00020 TABLE 20 No Dipeptide 1 L-prolyl-L-alanine, Pro-Ala 2 L-alanyl-L-proline, Ala-Pro 3 L-prolyl-L-arginine, Pro-Arg 4 L-arginyl-L-proline, Arg-Pro 5 L-prolyl-L-asparagine, Pro-Asn 6 L-asparaginyl-L-proline, Asn-Pro 7 L-prolyl-L-aspartic acid, Pro-Asp 8 L-aspartyl-L-proline, Asp-Pro 9 L-prolyl-L-cysteine, Pro-Cys 10 L-cysteinyl-L-proline, Cys-Pro 11 L-prolyl-L-glutamine, Pro-Gln 12 L-glutaminyl-proline, Gln-Pro 13 L-prolyl-L-glutamic acid, Pro-Glu 14 L-glutamyl-L-proline, Glu-Pro 15 L-prolyl-L-glycine, Pro-Gly 16 L-glycyl-L-proline, Gly-Pro 17 L-prolyl-L-histidine, Pro-His 18 L-histidyl-L-proline, His-Pro 19 L-prolyl-L-isoleucine, Pro-Ile 20 L-isoleucyl-L-proline, Ile-Pro 21 L-prolyl-L-leucine, Pro-Leu 22 L-leucyl-L-proline, Leu-Pro 23 L-prolyl-L-lysine, Pro-Lys 24 L-lysyl-L-proline, Lys-Pro 25 L-prolyl-L-methionine, Pro-Met 26 L-methionyl-L-proline, Met-Pro 27 L-prolyl-L-phenylalanine, Pro-Phe 28 L-phenylalanyl-L-proline, Phe-Pro 29 L-prolyl-L-proline, Pro-Pro 30 L-prolyl-L-serine, Pro-Ser 31 L-seryl-L-proline, Ser-Pro 32 L-prolyl-L-threonine, Pro-Thr 33 L-threonyl-L-proline, Thr-Pro 34 L-prolyl-L-tryptophane, Pro-Trp 35 L-tryptophyl-L-proline, Trp-Pro 36 L-prolyl-L-tyrosine, Pro-Tyr 37 L-tyrosyl-L-proline, Tyr-Pro 38 L-prolyl-L-valine, Pro-Val 39 L-valyl-L-proline, Val-Pro 40 D-Pro-L-Pro 41 Gly-Arg 42 Arg-Gly
[0213] Taste characteristics of each of the newly analyzed dipeptide compounds from the soy sauce and fermented rice paste samples were confirmed through Taste Dilution Analysis (TDA), Comparative Taste Dilution Analysis (cTDA) experiments, and it was confirmed that the dipeptide had an effect of increasing the salty taste and umami taste.
EXAMPLE 5. Sensory Evaluation of Soy Sauce and Fermented Rice Paste Recombinant Sample Comprising Newly Identified Dipeptides
[0214] By adding newly identified dipeptide compounds in Table 20 and the to the recombinant sample prepared in Example 3, recombinant sample 1 (R1-recombinant1) of the soy sauce and fermented soy paste was prepared. In Table 21 to Table 29 below, the compositions of the recombinant sample 1 of soy sauce and fermented rice paste were shown. The values of Table 21 to Table 29 mean concentrations (umol/L) of each component, and the relative standard deviation (RSD(%)) was described after the numerical value. When preparing the recombinant sample 1, after confirming the quantitative analysis result and the cognitive threshold concentration of each component, it was prepared with substances selected according to the standard of Dot factor (a value calculated by dividing each component present in the sample with DoT)>0.1 in consideration of DoT (Does of Threshold).
TABLE-US-00021 TABLE 21 Group 1: Umami SS5-R1 SS6-R1 FRP2-R1 FRP3-R1 L-Asparagine 176 (?8) 182 (?4.7) 26 (?2.0) 79 (?2.2) L-Aspartic acid 5267 (?2.7) 6445 (?8.5) 515 (?6.5) 498 (?2.5) L-Glutamine 13773 (?2.5) 17403 (?6.3) 930 (?3.6) 564 (?2.3) L-Glutamic acid 28973 (?3.0) 30617 (?4.2) 904 (?4.6) 708 (?1.9) Succinic acid 2604 2331
TABLE-US-00022 TABLE 22 Group 2: Sweet SS5-R1 SS6-R1 FRP2-R1 FRP3-R1 L-Alanine 37304 (?6.8) 31397 (?4.5) 986 (?3.8) 1001 (?0.3) L-Proline 23275 (?3.4) 27988 (?6.0) 355 (?5.7) 297 (?3.5) L-Threonine 17393 (?3.7) 17278 (?7.5) 339 (?4.3) 351 (?2.2) L-Serine 12320 (?4.0) 14346 (?6.8) 527 (?4.1) 617 (?7.5) Glycine 14232 (?5.8) 15556 (?6.5) 479 (?5.4) 484 (?0.2) Glucose 7367 10009 325754 330817 Betaine 766 981
TABLE-US-00023 TABLE 23 Group 3: Bitter SS5-R1 SS6-R1 FRP2-R1 FRP3-R1 L-Arginine 6415 (?2.1) 5463 (?6.1) 583 (?5.2) 623 (?0.4) L-Histidine 2065 (?2.7) 2842 (?9.7) 161 (?0.5) 128 (?0.6) L-Isoleucine 23692 (?18.6) 32358 (?8.2) 579 (?3.5) 458 (?3.2) L-Leucine 33898 (?19.5) 46673 (?9.0) 1046 (?4.0) 918 (?2.0) L-Lysine 11174 (?7.9) 14418 (?6.9) 720 (?5.8) 476 (?0.3) L-Methionine 2201 (?16.0) 3514 (?14.6) 170 (?4.3) 108 (?7.9) L-Phenylalanine 15152 (?14.6) 19238 (?8.5) 560 (?3.0) 473 (?2.5) L-Tryptophane 249 (?3.7) 394 (?4.8) 115 (?6.0) 68 (?1.6) L-Tyrosine 2207 (?3.7) 2274 (?9.9) 472 (?2.2) 400 (?0.8) L-Valine 25227 (?12.3) 31515 (?8.3) 755 (?4.2) 637 (?1.8) Inosine 22 (?21.1) Hypoxanthine 269 (?1.8) 315 (?4.5) 50 (?2.5) 58 (?14.4) Xanthine 161 (?4.8) 151 (?3.1) 13 (?9.5)
TABLE-US-00024 TABLE 24 Group 4: Salty SS5-R1 SS6-R1 FRP2-R1 FRP3-R1 Ammonium 148786 (?8.9) 165144 (?11.7) 88008 (?12.6) 76594 (?7.4) Potassium 78205 (?8.4) 79848 (?11.6) 18838 (?7.3) 16148 (?17.8) Magnesium 9071 (?5.5) 17127 (?3.5) 6087 (?0.8) 5646 (?5.9) Sodium 351936 (?2.2) 332739 (?12.0) 465401 (?7.3) 510141 (?8.8) Chloride 31481 303800 322708 348660
TABLE-US-00025 TABLE 25 Group 5: Sour SS5-R1 SS6-R1 FRP2-R1 FRP3-R1 Acetic acid 4596 2699 L-Lactic acid 15319 6869
TABLE-US-00026 TABLE 26 Group 6: Kokumi SS5-R1 SS6-R1 FRP2-R1 FRP3-R1 ?-Glu-Gly 37 (?6.5) 76 (?3.0) 7 (?1.4) 7 (?0.3) ?-Glu-Glu 82 (?3.2) 76 (?2.7) ?-Glu-Gln 63 (?5.8) 24 (?8.1) ?-Glu-Leu 146 (?5.9) 252 (?4.6) 0.2 (?6.9) 0.2 (?6.6) ?-Glu-Met 7 (?15.7) 17 (?10.1) 0.1 (?41.8)) 0.1 (?73.6)) ?-Glu-His 11 (?5.3) 37 (?5.1) 4 (?2.3) 4 (?0.1)
TABLE-US-00027 TABLE 27 Group 7: Astringent SS5-R1 SS6-R1 FRP2-R1 FRP3-R1 ?-Glu-Ala 132 (?5.2) 94 (?3.5)
TABLE-US-00028 TABLE 28 Group 8: Umami-enhancing substances SS5-R1 SS6-R1 FRP2-R1 FRP3-R1 pyroGlu-Pro 2355 (?3.4) 1344 (?9.8) pyroGlu-Glu 332 (?1.1) 404 (?9.2) 2.6 (?17.5) 9.8 (?10.6) pyroGlu-Gln 67 (?8.2) 170 (?15.2) 2 (?6.2) 12.3 (?5.4) pyroGlu-Ser 2.6 (?3.5) Pro-Pro 447 (?6.1) 288 (?14.1) 6.8 (?7.8) 3.5 (?9.1) Pro-Glu 265 (?2.1) 262 (?13.5)
TABLE-US-00029 TABLE 29 Group 9: Salt-enhancing substances SS5-R1 SS6-R1 FRP2-R1 FRP3-R1 Pro-Ala 4.4 (?18.2) 16.4 (?3.6) Pro-Lys 2.4 (?3.5) 2.3 (?6.4) Pro-Ser 124 (?1.1) 78 (?13.8) 7.8 (?1.4) Pro-Val 73 (?7.9) 63 (?18.5) 2.6 (?6.5) 11.0 (?4.3) Arg-Pro 75 (?4.5) 13 (?26.2) 11.0 (?9.2) 3.5 (?3.5) Lys-Pro 2.7 (?16.3) Ser-Pro 253 (?2.7) 141 (?13.8) 35.6 (?3.0) 20.7 (?5.1) Val-Pro 303 (?3.9) 104 (?13.2) 13.9 (?3.5) 8.4 (?0.9) Arg-Gly 10 (?10.9) 4 (?24.5) 4.2 (?1.5) 5.7 (?0.6) Gly-Arg 16 (?8.9) 16 (?11.1) 11.4 (?10.6) 19.8 (?5.0)
[0215] The sensory evaluation of the 4 kinds of the recombinant sample 1 (SS5-R1, SS6-R1, FRP2-R1, FRP3-R1) was performed by the same method as Example 1, and the result of comparing the sensory evaluation result of the soy sauce samples (SS5, SS6) and fermented rice paste samples (FRP2, FRP3) of Example 1 and the sensory evaluation result of the recombinant sample 1 was shown in
[0216] As could be confirmed in
EXAMPLE 6. Analysis of Taste Components in Soy Sauce and Fermented Rice Paste Samples II
[0217] As it was expected that there were additional taste components related to umami taste (umami taste, kokumi taste) and salty taste largely affecting umami taste in the soy sauce and fermented rice paste samples, an additional verification experiment for unknown substances was performed.
[0218] In order to find a long chain peptide compound, longer than dipeptide, having taste activity, a sensoproteomics approach method was used. Such a method is a method of combining a sensory evaluation method for confirming taste characteristics to proteomics method widely used in the life science field (J. Agric. Food Chem. 2018, 66, 42, 11092-11104).
[0219] In order to identify unknown long chain peptide compounds, they were analyzed using Ultra-High Performance Liquid Chromatography-Time-Of-Flight-Mass Spectrometry (UHPLC-Tof-MS) and De Novo Sequencing. The specific experimental method was described in Table 30 below.
TABLE-US-00030 TABLE 30 Analysis item Equipment Analysis condition Peptide Triple TOF 6600 mass Kinetex C18 column, 150 ? (Untargeted long spectrometer with 2 mm, 1.7 ?m; chain peptide) Shimadzu Nexera X2 Phenomenex) system 0.3 mL/min A: 1% Formic acid/H2O B: 1% Formic acid/ Acetonitrile Peptide 5500 + QTrap Mass Kinetex, 1.7 ?m C8, 100 ? (Targeted long Spectroeter (2.1 ? 100 mm; chain peptide) Phenomenex) 0.3 mL/min A: 1% Formic acid/H2O B: 1% Formic acid/ Acetonitrile
[0220] As the result of analysis, the newly identified long chain peptides were described in Table 31 below.
TABLE-US-00031 TABLE31 Longchain SEQID No peptide NO: 1 ALDPLPT 1 2 DGFP 2 3 DGML 3 4 DNEDTP 4 5 DTDEPN 5 6 EEL 6 7 EEV 7 8 EEY 8 9 ESLPALP 9 10 EVGYGY 10 11 LDYY 11 12 LPPP 12 13 MTTFTW 13 14 PPPP 14 15 PPPPP 15 16 DAPL 16 17 DVL 17 18 GGPF 18 19 GNPF 19 20 EVLK 20 21 FADSL 21 22 LAL 22 23 LLL 23 24 LLQ 24 25 LPL 25 26 PLL 26 27 TPL 27 28 VLL 28
[0221] Each taste characteristic of the long chain peptide compounds newly analyzed from the soy sauce and fermented rice paste samples was confirmed through Taste Dilution Analysis (TDA), Comparative Taste Dilution Analysis (cTDA) experiments, and it was confirmed that they mostly enhanced umami taste, kokumi taste, and salty taste related to umami taste. The threshold values sensed sensually of each long chain peptide compounds were confirmed, and the result was shown in
[0222]
[0223] In
[0224] In addition, the minimal concentration at which such a taste can be sensed (Threshold) was lower than the case in which the long chain peptide was comprised in the recombinant sample in which other taste components were comprised (mTC), and the case in which it was comprised in water (iTC), so it was confirmed that when the long chain peptide was comprised in the recombinant sample in which other taste components were comprised, even if it was comprised in a trace amount, the taste related to flavor modulating could be expressed.
EXAMPLE 7. Sensory Evaluation of Soy Sauce and Fermented Rice Paste Recombinant Sample Comprising Newly Identified Dipeptides and Long Chain Peptides
[0225] By adding newly identified dipeptide compounds in Table 20 and newly identified long chain peptide compounds in Table 31 to the recombinant sample prepared in Example 3, recombinant sample 2 (R1-recombinant2) of the soy sauce and fermented soy paste was prepared. In other words, the recombinant sample 2 of soy sauce and fermented rice paste below comprise the long chain peptide compounds of Table 32 below, in addition to the recombinant sample 1 having the compositions of Table 21 to Table 29. The values of Table 32 mean concentrations (umol/L) of each component, and the relative standard deviation (RSD(%)) was described after the numerical value.
TABLE-US-00032 TABLE32 Long chain SEQ peptide IDNO SS5-R2 SS6-R2 FRP2-R2 FRP3-R2 ALDPLPT 1 0.58(?12.9) 0.06(?8.7) DGFP 2 0.09(?5.0) 0.01(?10.0) DGML 3 0.51(?5.9) 8.91(?10.7) 0.03(?12.5) 0.13(?5.4) DNEDTP 4 3.33(?8.3) 1.17(?13.6) 1.17(?13.7) 0.006(?20.3) EEL 6 1.91(?49.3) 2.9(?47.8) EEV 7 1.37(?29.9) 3.05(?26.1) EEY 8 0.35(?16.4) 0.64(?31.1) ESLPALP 9 0.52(?17.1) EVGYGY 10 0.77(?11.7) 0.08(?12.7) 0.002 LDYY 11 3.52(?8.4) 0.6(?3.7) 0.003 0.013(?18.3) LPPP 12 1.87(?2.2) 1.34(?2.4) 0.35(?17.6) 0.15(?3.3) MTTFTW 13 1.23(?4.9) 0.65(?3.8) PPPP 14 1.78(?36) 3.33(?2.9) 0.1(?7.4) 0.02(?4.2) PPPPP 15 1.08(?3.8) 0.61(?1.4) 0.04(?6.7) 0.006(?1.9) DAPL 16 0.03(?9.5) 0.02(?1.0) 0.23(?11.9) 0.09(?2.7) DVL 17 0.54(?50.9) 0.71(?31.8) 0.33(?27.5) 0.96(?10.5) GGPF 18 0.04(?52.3) 0.01(?41.0) 0.02(?37.7) 0.06(?9.8) EVLK 20 0.9(?28.3) 0.09(?4.8) FADSL 21 <0.001(?1.4) LAL 22 0.21(?9.5) 0.04(?7.0) 0.6(?30.1) 0.02(?11.4) LLL 23 0.06(?0.8) 0.02(?0.6) 0.01(?21.6) 0.01(?0.8) LLQ 24 0.03(?19.4) 0.08(?60.2) 0.14(?18.3) LPL 25 0.03(?6.4) 0.2(?3.5) PLL 26 0.09(?9.4) 0.09(?9.4) 0.03(?12.2) 0.06(?2.0) TPL 27 0.39(?4.1) 0.15(?14.6) 0.15(?44.4) 1.9(?19.0) VLL 28 0.04(?24.2) 0.05(?4.2)
[0226] The sensory evaluation of 4 kinds of the recombinant sample 2 (SS5-R2, SS6-R2, FRP2-R2, FRP3-R2) was performed by the same method as Example 1, and the result of comparing the sensory evaluation result of 4 kinds of the recombinant sample 1 (SS5-R1, SS6-R1, FRP2-R1, FRP3-R1) and the sensory evaluation result of the recombinant sample 2 of Example 5 was shown in
[0227] The sensory evaluation result of the soy sauce and fermented rice paste samples (SS5, SS6, FRP2, FRP3, Control group 1 to control group 4, respectively) and each of the recombinant samples (Example 3, SS5-BR, SS6-BR, FRP2-BR, FRP3-BR, Experimental groups 1-1, 2-1, 3-1, 4-1, respectively), recombinant sample 1 (Example 5, SS5-R1, SS6-R1, FRP2-R1, FR3-R1, Experimental groups 1-2, 2-2, 3-2, 4-2, respectively), recombinant sample 2 (Example 7, SS5-R2, SS6-R2, FRP2-R2, FRP3-R2, Experimental groups 1-3, 2-3, 3-3, 4-3, respectively) were summarized in Table 33 to Table 36 below. Values of measuring 6 taste attributes (sour taste, salty taste, sweet taste, bitter taste, umami tastes, kokumi taste) with a 5-point index were described, and the difference between the experimental group value and the control group value was described in parentheses after each of the experimental group values.
TABLE-US-00033 TABLE 33 SS5 SS5-BR SS5-R1 SS5-R2 (Control (Experimental Experimental (Experimental group 1) group 1-1) group 1-2) group 1-3) Sour 1.3 1.0 (?0.3) 1.3 (0) 1.3 (0) taste Salty 3.4 2.2 (?1.2) 3.4 (0) 3.3 (?0.1) taste Sweet 0.7 0.8 (0.1) 0.7 (0) 0.7 (0) taste Bitter 2.0 1.8 (?0.2) 2.0 (0) 1.7 (?0.3) taste Umami 2.6 2.4 (?0.2) 2.7 (0.1) 2.9 (0.3) Kokumi 1.6 1.7 (0.1) 1.7 (0.1) 1.8 (0.2)
TABLE-US-00034 TABLE 34 SS6 SS6-BR SS6-R1 SS6-R2 (Control (Experimental (Experimental (Experimental group 2) group 2-1) group 2-2) group 2-3) Sour 1.2 1.0 (?0.2) 1.3 (0.1) 1.2 (0) taste Salty 3.1 2.0 (?1.1) 3.1 (0) 3.1 (0) taste Sweet 1.2 1.3 (0.1) 1.1 (?0.1) 1.4 (0.2) taste Bitter 1.8 1.5 (?0.3) 1.8 (0) 1.4 (?0.4) taste Umami 2.7 2.4 (?0.3) 2.8 (0.1) 2.9 (0.2) Kokumi 1.7 1.3 (?0.4) 1.7 (0) 1.8 (0.1)
TABLE-US-00035 TABLE 35 FRP2 FRP2-BR FRP2-R1 FRP2-R2 (Control (Experimental (Experimental (Experimental group 3) group 3-1) group 3-2) group 3-3) Sour 0.9 0.8 (?0.1) 0.8 (?0.1) 0.8 (?0.1) taste Salty 3.0 2.2 (?0.8) 2.7 (?0.3) 2.7 (?0.3) taste Sweet 1.8 2.3 (0.5) 1.8 (0) 2 (0.2) taste Bitter 0.4 0.3 (?0.1) 0.5 (0.1) 0.6 (0.2) taste Umami 1.8 1.4 (?0.4) 1.6 (?0.2) 1.7 (?0.1) Kokumi 1.4 0.9 (?0.5) 1.3 (?0.1) 1.5 (0.1)
TABLE-US-00036 TABLE 36 FRP3 FRP3-BR FRP3-R1 FRP3-R2 (Control (Experimental (Experimental (Experimental group 4) group 4-1) group 4-2) group 4-3) Sour 1.0 0.8 (?0.2) 0.9 (?0.1) 0.9 (?0.1) taste Salty 2.8 2 (?0.8) 2.5 (?0.3) 2.6 (?0.2) taste Sweet 2.1 2.5 (0.4) 2.0 (?0.1) 2.2 (0.1) taste Bitter 0.3 0.5 (0.2) 0.4 (0.1) 0.3 (0) taste Umami 2.0 1.4 (?0.6) 1.8 (?0.2) 1.9 (?0.1) Kokumi 1.2 0.6 (?0.6) 1.0 (?0.2) 1.1 (?0.1)
[0228] As could be confirmed in Table 33 to Table 36 above, when 6 taste attributes were compared, samples comprising common taste components that account for most (95% or more) of the taste components of the food samples (experimental groups 1-1, 2-1, 3-1, 4-1) had a very significant difference in the sensory evaluation result with the food samples (control groups 1, 2, 3, 4).
[0229] It was confirmed that taste characteristics became similar to the food sample, when trace substances (dipeptide compound, or dipeptide compound and long chain peptide compound) among the total taste components, and it was confirmed that these trace components are important components exhibiting an umami taste in the soy sauce and fermented rice paste.
Newly Identified Dipeptide and Long Chain Peptide Compounds
[0230] The taste active compounds and taste modulation compounds newly identified in the present application were summarized in Table 37 below, and total 127 compounds were newly identified.
TABLE-US-00037 TABLE37 Dipeptide andlong SEQ No Compoundgroup chainpeptide IDNO: 1 Prolylpeptides Pro-Ala 2 Prolylpeptides Pro-Asn 3 Prolylpeptides Pro-Glu 4 Prolylpeptides Pro-Gln 5 Prolylpeptides Pro-His 6 Prolylpeptides Pro-Ile 7 Prolylpeptides Pro-Leu 8 Prolylpeptides Pro-Met 9 Prolylpeptides Pro-Pro 10 Prolylpeptides Pro-Phe 11 Prolylpeptides Pro-Ser 12 Prolylpeptides Pro-Thr 13 Prolylpeptides Pro-Val 14 Prolylpeptides Ala-Pro 15 Prolylpeptides Pro-Gly 16 Prolylpeptides Arg-Pro 17 Prolylpeptides Asn-Pro 18 Prolylpeptides Asp-Pro 19 Prolylpeptides Thr-Pro 20 Prolylpeptides His-Pro 21 Prolylpeptides Ile-Pro 22 Prolylpeptides Leu-Pro 23 Prolylpeptides Ser-Pro 24 Prolylpeptides Gly-Pro 25 Prolylpeptides Tyr-Pro 26 Prolylpeptides Val-Pro 27 Prolylpeptides Glu-Pro 28 Prolylpeptides Pro-Tyr 29 Prolylpeptides Pro-Asp 30 Prolylpeptides Pro-Cys 31 Prolylpeptides Cys-Pro 32 Prolylpeptides Gln-Pro 33 Prolylpeptides Pro-Lys 34 Prolylpeptides Lys-Pro 35 Prolylpeptides Met-Pro 36 Prolylpeptides Phe-Pro 37 Prolylpeptides Pro-Trp 38 Prolylpeptides Trp-Pro 39 Prolylpeptides D-Pro-L-Pro 40 Arginylpeptides Arg-Ala 41 Arginylpeptides Arg-Gly 42 Arginylpeptides Arg-Gln 43 Arginylpeptides Gly-Arg 44 Arginylpeptides Val-Arg 45 Arginylpeptides Arg-Val 46 Arginylpeptides Ala-Arg 47 Arginylpeptides Pro-Arg 48 Arginylpeptides Arg-Ser 49 Arginylpeptides Asp-Arg 50 Arginylpeptides Arg-Asp 51 Arginylpeptides Arg-Leu 52 Arginylpeptides Lys-Arg 53 Arginylpeptides Glu-Arg 54 ?-Glutamylpeptides ?-Glu-Ala 55 ?-Glutamylpeptides ?-Glu-Gly 56 ?-Glutamylpeptides ?-Glu-Ser 57 ?-Glutamylpeptides ?-Glu-Val 58 ?-Glutamylpeptides ?-Glu-The 59 ?-Glutamylpeptides ?-Glu-Pro 60 ?-Glutamylpeptides ?-Glu-Leu 61 ?-Glutamylpeptides ?-Glu-Ile 62 ?-Glutamylpeptides ?-Glu-Lys 63 ?-Glutamylpeptides ?-Glu-Glu 64 ?-Glutamylpeptides ?-Glu-Gln 65 ?-Glutamylpeptides ?-Glu-His 66 ?-Glutamylpeptides ?-Glu-Phe 67 ?-Glutamylpeptides ?-Glu-Tyr 68 ?-Glutamylpeptides ?-Glu-Asp 69 ?-Glutamylpeptides ?-Glu-Arg 70 ?-Glutamylpeptides ?-Glu-Trp 71 ?-Glutamylpeptides ?-Glu-Gly 72 ?-Glutamylpeptides ?-Glu-Ala 73 ?-Glutamylpeptides ?-Glu-Pro 74 ?-Glutamylpeptides ?-Glu-Val 75 ?-Glutamylpeptides ?-Glu-Ser 76 ?-Glutamylpeptides ?-Glu-Ile 77 ?-Glutamylpeptides ?-Glu-Thr 78 ?-Glutamylpeptides ?-Glu-Leu 79 ?-Glutamylpeptides ?-Glu-Asn 80 ?-Glutamylpeptides ?-Glu-Lys 81 ?-Glutamylpeptides ?-Glu-Glu 82 ?-Glutamylpeptides ?-Glu-His 83 ?-Glutamylpeptides ?-Glu-Trp 84 ?-Glutamylpeptides ?-Glu-Asp 85 ?-Glutamylpeptides ?-Glu-Tyr 86 ?-Glutamylpeptides ?-Glu-Arg 87 Glutamylpeptides Ala-Glu 88 Glutamylpeptides Asn-Glu 89 Glutamylpeptides His-Glu 90 Glutamylpeptides Asp-Glu 91 Glutamylpeptides Phe-Glu 92 Glutamylpeptides Tyr-Glu 93 Glutamylpeptides Ile-Glu 94 Glutamylpeptides Val-Glu 95 Glutamylpeptides Ser-Glu 96 Glutamylpeptides Pro-Glu 97 Glutamylpeptides Thr-Glu 98 Glutamylpeptides Met-Glu 99 Glutamylpeptides Leu-Glu 100 Longchainpeptides ALDPLPT 1 101 Longchainpeptides DGFP 2 102 Longchainpeptides DGML 3 103 Longchainpeptides DNEDTP 4 104 Longchainpeptides DTDEPN 5 105 Longchainpeptides EEL 6 106 Longchainpeptides EEV 7 107 Longchainpeptides EEY 8 108 Longchainpeptides ESLPALP 9 109 Longchainpeptides EVGYGY 10 110 Longchainpeptides LDYY 11 111 Longchainpeptides LPPP 12 112 Longchainpeptides MTTFTW 13 113 Longchainpeptides PPPP 14 114 Longchainpeptides PPPPP 15 115 Longchainpeptides DAPL 16 116 Longchainpeptides DVL 17 117 Longchainpeptides GGPF 18 118 Longchainpeptides GNPF 19 119 Longchainpeptides EVLK 20 120 Longchainpeptides FADSL 21 121 Longchainpeptides LAL 22 122 Longchainpeptides LLL 23 123 Longchainpeptides LLQ 24 124 Longchainpeptides LPL 25 125 Longchainpeptides PLL 26 126 Longchainpeptides TPL 27 127 Longchainpeptides VLL 28
[0231] From the above description, those skilled in the art to which the present invention pertains will understand that the present invention can be implemented in other specific forms without changing its technical spirit or essential features. In this regard, the examples described above should be understood as illustrative and not restrictive in all aspects. The scope of the present invention should be interpreted as all changed or modified forms derived from the meaning and scope of the claims described below and equivalent concepts thereof are included in the scope of the present invention.