CN107114752A - Savoury peptide, dense taste imparting agent, flavoring and preparation method thereof - Google Patents
Savoury peptide, dense taste imparting agent, flavoring and preparation method thereof Download PDFInfo
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- CN107114752A CN107114752A CN201710210276.6A CN201710210276A CN107114752A CN 107114752 A CN107114752 A CN 107114752A CN 201710210276 A CN201710210276 A CN 201710210276A CN 107114752 A CN107114752 A CN 107114752A
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids
- A23L27/22—Synthetic spices, flavouring agents or condiments containing amino acids containing glutamic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/02—Linear peptides containing at least one abnormal peptide link
Abstract
The invention discloses savoury peptide, dense taste imparting agent, flavoring and preparation method thereof.The savoury peptide of the present invention（γ‑Glu‑γ‑Glu‑γ‑Glu‑γ‑Glu‑val）With good stability, the savoury of food particularly flavouring is remarkably improved under 20 100mg/kg concentration.Specifically preparation process is：It is soluble in water after glutamine is mixed with valine, add solution quality 0.001 0.4%（w/w）Glutaminase or γ-glutamate transpeptidase, the pH to 8.0 10.0 of solution is adjusted with 10 mol/l sodium hydroxide solution, is reacted 3 12 hours at 25 50 DEG C, between the rear pH to 6 ~ 7 with 4 mol/L hydrochloric acid readjustment, 90 DEG C of min of enzyme 10 that go out.
Description
Technical field
The present invention relates to peptide with flavor effect and preparation method thereof, and in particular to the γ-Glutamyl Peptide with savoury
And preparation method thereof.
Background technology
γ-Glutamyl Peptide is deposited with a variety of animals and plants and fermented food, being that a kind of safety is natural extensively, safety food into
Point.Its primary structure of common glutathione is γ-Glu-Cys-Gly, is a kind of typical γ-Glutamyl Peptide.Modern study
Show that γ-Glutamyl Peptide is relevant with the metabolic activity and physiological function of organism, most of γ-Glutamyl Peptide has calm in addition
Depressurize, fatigue of releiving, anticancer removing toxic substances, complexation heavy metal ion, maintain cellular metal ions balance etc. physiological function.
In recent years, it has been found that γ-Glutamyl Peptide also has stronger flavor characteristic.Japanese aginomoto strain formula meeting in 2002
Society is disclosed by exploring the diversified compound with CaSR agonist activities, finds to assign with more excellent dense taste
Effect, the dense taste imparting effect particularly with preceding taste type, and with excellent stability, can be easy and produce at low cost
The material for being capable of imparting body taste with other there is CaSR to swash there is provided the dense taste imparting agent comprising the material, and by the material
The combinations of substances of dynamic agent activity using compound dense taste imparting agent.Include γ-Glu-Abu (L- gamma-glutamyl-L-2- ammonia
Base butyric acid) dense taste imparting agent, and the material with other have the combinations of substances of CaSR agonist activities using answer
Close dense taste imparting agent (number of patent application 201080024054.1).
Most of γ-Glutamyl Peptide under low consistency conditions has slight astringent taste, with the raising of concentration, γ-paddy ammonia
Acyl peptide starts that primary taste is presented.Such as γ-Glu-Glu have delicate flavour, γ-Glu-tyr bitter taste when concentration is 10mmol/L
Threshold value is twice of its astringent taste threshold value.In delicate flavour solution, γ-Glutamyl Peptide has savoury, and threshold value is also being decreased obviously.With
People further appreciate that scholar has found that γ-Glutamyl Peptide has the feature of savoury material to flavor peptide：1. base in aqueous
This insipidness or only slight taste (astringent taste or tart flavour)；2. increasing can be cooperateed with other taste compounds in system
Effect is acted on, and is added in the solution system containing delicate flavour material, will not change the basic taste sensation intensity of solution, but can coordinate each
Taste is planted, dense sense (kokumi) is dramatically increased；3. compared with pure water solution, threshold value is decreased obviously in delicate flavour solution.
Table 1 has reported γ-Glutamyl Peptide flavor characteristic and threshold value list
So far, there is not yet γ-Glu- γ-Glu- γ-Glu- γ-Glu-val have the report of dense taste.
The content of the invention
It is an object of the invention to overcome deficiencies of the prior art, there is provided one kind utilization glutamine enzymatic synthesis
The preparation method of γ-Glutamyl Peptide.
The purpose of the present invention is achieved through the following technical solutions.
A kind of savoury peptide, its amino acid sequence is γ-Glu- γ-Glu- γ-Glu- γ-Glu-val.
A kind of dense taste imparting agent, it is combined by the oligopeptides and more than one following peptide：γ-Glu-X-Gly
(X represents amino acid or amino acid derivativges), γ-Glu-Val-Y (Y represents amino acid or amino acid derivativges), γ-Glu-
Abu、γ-Glu-Ala、γ-Glu-Gly、γ-Glu-Cys、γ-Glu-Met、γ-Glu-Thr、γ-Glu-Val、γ-Glu-
Orn、Asp-Gly、Cys-Gly、Cys-Met、Glu-Cys、Gly-Cys、Leu-Asp、D-Cys、γ-Glu-Met(O)、γ-
Glu-γ-Glu-Val、γ-Glu-Val-NH2、γ-Glu-Val-ol、γ-Glu-Ser、γ-Glu-Tau、γ-Glu-Cys
(S-Me) (O), γ-Glu-Leu, γ-Glu-Ile, γ-Glu-t-Leu and γ-Glu-Cys (S-Me).
A kind of flavoring containing the oligopeptides, its contain more than 500 weight mg/kg γ-Glu- γ-Glu- γ-
Glu-γ-Glu-val。
A kind of flavoring containing the oligopeptides, its contain more than 1500 weight mg/kg γ-Glu- γ-Glu- γ-
Glu-γ-Glu-val。
The application of described flavoring, be specifically：Added in raw-food material outside the flavoring, also add glutamic acid, breast
At least one of acid, citric acid, malic acid and butanedioic acid organic acid or its salt make it in food added to raw-food material
Concentration be 0.005~0.1 weight %.
The method for preparing a kind of savoury peptide, be specifically, glutamine and free valine, mol ratio is 1-2:1, it is molten
Yu Shuizhong obtains solution, and regulation reaction pH is 8.0-10.0, and addition glutaminase or gamma-glutamyl amine transpeptidase are solution quality
0.02-1% (w/w), reacts 3-12 hours at 25-50 DEG C, between the rear pH to 6~7 with 4mol/L hydrochloric acid readjustment, 90 DEG C of enzymes that go out
10min, obtains-Glu- γ-Glu- γ-Glu- γ-Glu-val the reaction solutions of γ containing oligopeptides.With 5 μm of XSelect HSS T3
4.6x 250mm analytical columns, mobile phase A liquid is 0.1% (V/V) formic acid-aqueous solution；Mobile phase B liquid be 0.1% (V/V) formic acid-
Acetonitrile solution, column temperature is 40 DEG C, and flow velocity is 1mL/min, the μ L of sample size 10 of reaction solution, using high performance liquid chromatography to reaction solution
Gradient elution is carried out, the 7th peak is oligopeptides γ-Glu- γ-Glu- γ-Glu- γ-Glu-val.
Further, the concentration of solution GLN and free valine is in 400-1000mmol/L.
The present invention compared with prior art, has the following advantages that：
1) there is savoury characteristic present invention firstly discloses γ-Glu- γ-Glu- γ-Glu- γ-Glu-val.
2) make public for the first time and utilize glutaminase or gamma-glutamyl amine transpeptidase catalytic preparation of gamma-Glu- γ-Glu-
γ-Glu-γ-Glu-val。
Brief description of the drawings
Fig. 1 is the disparity map that valine adds the no flavor characteristic of enzyme with glutamine mixture；
Fig. 2 is the liquid chromatogram of mixture after reaction；
Fig. 3 γ-Glu- γ-Glu- γ-Glu- γ-GluVal second order mses figure；
Fig. 4 is γ-Glu- γ-Glu- γ-Glu- γ-Glu-val flavor specificity analysis figure；
Fig. 5 a~Fig. 5 b are respectively mixed system to steamed beef soup and the flavor improvement comparison diagram of bone soup.
Embodiment
Work further citing, but implementation of the invention and guarantor are specifically implemented to the present invention below in conjunction with accompanying drawing and example
Protect not limited to this.
Embodiment 1
300mM glutamine and 300mM valines are dissolved in 100g water, the pH value of solution is adjusted to 10.0, adds
0.4g glutaminases (Japanese Tian Ye Co., Ltd., vigor is 100GTU/g), 12h is reacted at 37 DEG C respectively, after use 4mol/L
After hydrochloric acid readjustment pH to 7.0,90 DEG C of enzyme 10min that go out carry out sensory evaluation to product flavor characteristic, flavor characteristic before and after it reacts
Such as Fig. 1.
As seen from Figure 1, after reaction terminates, savoury, delicate flavour and the saline taste of reaction solution are all significantly improved.
HPLC liquid phases carry out quantitative analysis to reaction product：Analytical column：XSelect HSS T35μm 4.6x 250mm；Stream
Dynamic phase：A liquid：0.1% (V/V) formic acid-aqueous solution；B liquid：0.1% (V/V) formic acid-acetonitrile solution；Column temperature：40 DEG C, flow velocity：
1mL/min.The μ L of sample size 10.Its liquid chromatogram is shown in Fig. 4.It is as shown in table 2 that mobile phase carries out graded.
Table 2
| Time/min | 0 | 5 | 10 | 15 | 20 |
| A/% | 90 | 85 | 20 | 90 | 90 |
In Fig. 2, appearance time is that 5.619 corresponding peaks 7 are γ-glu- γ-glu- γ-glu- γ-glu-val, to peak 7
It is collected, freeze-drying obtains γ-glu- γ-glu- γ-glu- γ-glu-val, and carries out sensory evaluation.
UPLC-MS/MS carries out qualitative analysis to reaction product：Including：An Agilent 1290series UPLC
System (Agilent Technologies) is used to separate each γ-Glu-peptides, with an elec-trospray
Ionization (ESI) mass spectrometer system (Q-TOF MS/MS, Bruker Daltonics) carries out qualitative analysis.Chromatographic column is：
Agilent ZORBAX RRHD SB-C18(2.1x 50mm,1.8μm).Sample size is 5 μ L.Liquid-phase condition is：Solution A is
0.1% formic acid-the aqueous solution, and solution B are 0.1% formic acid-acetonitrile solution, and gradient elution program is：0-10%B, 0-5.0min；
10-15%B, 5.0-10.0min；Then 100%B, 10.0-12.0min.MS conditions：Ionization (ionization)：Cation
Pattern；Drying gas (dry gas)：10L/min at 350 DEG C；Nebulizer (nebulizer pressure)：25psig；
Fragmentor (capillary voltage)：30V.Using UPLC-MS/MS to peak 7, its testing result such as Fig. 3.From the figure 3, it may be seen that one
Level structure is γ-glu- γ-glu- γ-glu- γ-glu-val.
0.01g γ-glu- γ-glu- γ-glu- γ-glu-val, and 0.5g salt and 0.3g monosodium glutamates are weighed, is dissolved
Sensory evaluation is carried out in 100g water, and with blank sample (0.5g salt and 0.3g monosodium glutamates are dissolved in 100g water).Sensory evaluation is real
Test and be made up of by 30-41 Sui 7 males and 9 women of sensory evaluation experience, Analyses Methods for Sensory Evaluation Results is shown in Fig. 4.
From fig. 4, it can be seen that addition 0.01g γ-glu- γ-glu- γ-glu- γ-glu-val sample is compared with the control, it is molten
The delicate flavour and saline taste of liquid are significantly improved.
Embodiment 2
Fresh Grade Breast and beef are respectively put into 15 times of weight clear water, 25min is incubated after boiling, noodle soup oil is dispelled in freezing
Fat, filters to obtain chicken soup and steamed beef soup.Add the salt of soup quality 0.5% (% is to account for soup quality meter, similarly hereinafter), addition 0.01%
γ-glu- γ-glu- γ-glu- γ-glu-val evaluate its flavor characteristic variations in chicken soup and steamed beef soup.Sensory evaluation is real
Test and be made up of by 30-41 Sui 7 males and 9 women of sensory evaluation experience, Analyses Methods for Sensory Evaluation Results such as Fig. 5 a- Fig. 5 b.
From Fig. 5 a-5b, 0.01% γ-glu- γ-glu- γ-glu- γ-glu-val chicken soup and beef is added
Soup, its delicate flavour and savoury are respectively provided with and significantly improved.
From table 3, γ-γ-glu- γ-glu- γ-glu- γ-glu-val and lactic acid have stronger flavor phase interaction
With addition monosodium glutamate and lactic acid can obviously reduce this γ-glu- γ-glu- γ-glu- γ-glu-val stimulation in taste threshold value.
Table 3 (% is the mass percent for accounting for water)
a:Tart flavour (mg/L), b:Savoury solution ph is transferred to 6.5
Embodiment 3
By bacillus amyloliquefaciens (Bacillus amyloliquefaciens) SWJS22 (Chinese microorganism strain preservations
Administration committee's common micro-organisms center, deposit number is CGMCC No.8425) fermented and cultured is inoculated in 1% inoculum concentration
(composition of fermentation medium is base：4% dregs of beans, 2% wheat bran, 2% corn flour) in, 37~39 DEG C of fermented and cultured 30h.Will fermentation
Liquid is in 4 DEG C, high speed centrifugation 10min under the conditions of 10000r/min, filters to obtain supernatant, i.e. glutaminase crude enzyme liquid.
600mM glutamine and 300mM valines are dissolved in 100g water, the pH value of solution is adjusted respectively to 9.0, is added
1g crude enzyme liquids, 40 DEG C respectively reaction 12h after, with 4mol/L hydrochloric acid adjust back pH to 7.0 after, 90 DEG C of enzyme 10min that go out, obtain γ-
Glu- γ-glu- γ-glu- γ-glu-val reaction solution.Using 5 μm of 4.6x250mm analytical columns of XSelect HSS T3,
Mobile phase A liquid is 0.1% (V/V) formic acid-aqueous solution；Mobile phase B liquid is 0.1% (V/V) formic acid-acetonitrile solution, and column temperature is 40
DEG C, flow velocity is 1mL/min, the μ L of sample size 10 of reaction solution, and gradient elution, the 7th are carried out to reaction solution using high performance liquid chromatography
Individual peak is oligopeptides γ-Glu- γ-Glu- γ-Glu- γ-Glu-Val.
Embodiment 4
Bacillus subtillis ATCC 6633 is inoculated in the fermentation medium (composition of fermentation medium with 1% inoculum concentration
For：4% dregs of beans, 2% wheat bran, 2% corn flour) in, 37~39 DEG C of fermented and cultured 48h.By zymotic fluid in 4 DEG C, 10000r/min
Under the conditions of high speed centrifugation 10min, filter to obtain supernatant, i.e. gamma-glutamyl amine transpeptidase crude enzyme liquid.
600mM glutamine and 400mM valines are dissolved in 100g water, the pH value of solution is adjusted respectively to 8.0, is added
1g gamma-glutamyl amine transpeptidase crude enzyme liquids, after 40 DEG C respectively reaction 6h, are adjusted back after pH to 7.0,90 DEG C go out with 4mol/L hydrochloric acid
Enzyme 10min, obtains the reaction solution containing γ-Glu- γ-Glu- γ-Glu-Val.Using 5 μm of 4.6x of XSelect HSS T3
250mm analytical columns, mobile phase A liquid is 0.1% (V/V) formic acid-aqueous solution；Mobile phase B liquid is that 0.1% (V/V) formic acid-acetonitrile is molten
Liquid, column temperature is 40 DEG C, and flow velocity is 1mL/min, the μ L of sample size 10 of reaction solution, and ladder is carried out to reaction solution using high performance liquid chromatography
Degree elution, the 7th peak is oligopeptides γ-Glu- γ-Glu- γ-Glu- γ-Glu-Val.
Claims (8)
1. a kind of savoury peptide, it is characterised in that amino acid sequence is γ-Glu- γ-Glu- γ-Glu- γ-Glu-val.
2. a kind of dense taste imparting agent, it is characterised in that combined by oligopeptides described in claim 1 and more than one following peptide and
Into：γ-Glu-X-Gly、γ-Glu-Val-Y、γ-Glu-Abu、γ-Glu-Ala、γ-Glu-Gly、γ-Glu-Cys、γ-
Glu-Met、γ-Glu-Thr、γ-Glu-Val、γ-Glu-Orn、Asp-Gly、Cys-Gly、Cys-Met、Glu-Cys、Gly-
Cys、Leu-Asp、D-Cys、γ-Glu-Met(O)、γ-Glu-γ-Glu-Val、γ-Glu-Val-NH2、γ-Glu-Val-
ol、γ-Glu-Ser、γ-Glu-Tau、γ-Glu-Cys(S-Me)(O)、γ-Glu-Leu、γ-Glu-Ile、γ-Glu-t-
Leu and γ-Glu-Cys (S-Me)；X, Y represent amino acid or amino acid derivativges.
3. a kind of flavoring containing oligopeptides described in claim 1, it is characterised in that the γ containing more than 500 weight mg/kg-
Glu-γ-Glu-γ-Glu-γ-Glu-val。
4. flavoring according to claim 3, it is characterised in that the γ-Glu- γ containing more than 1500 weight mg/kg-
Glu-γ-Glu-γ-Glu-val。
5. the application of the flavoring described in claim 3, it is characterised in that add outside the flavoring, also add in raw-food material
At least one of glutamic acid, lactic acid, citric acid, malic acid and butanedioic acid organic acid or its salt make it added to raw-food material
Concentration in food is 0.005~0.1 weight %.
6. prepare a kind of method of savoury peptide described in claim 1, it is characterised in that glutamine and free valine, mole
Than for 1-2:1, soluble in water to obtain solution, regulation reaction pH is 8.0-10.0, and addition glutaminase or gamma-glutamyl amine turn peptide
Enzyme is solution quality 0.02-1%（w/w）, reacted 3-12 hour at 25-50 DEG C, it is rear with 4 mol/L hydrochloric acid readjustment pH to 6 ~ 7 it
Between, 90 DEG C of min of enzyme 10 that go out obtain-Glu- γ-Glu- γ-Glu- γ-Glu-val the reaction solutions of γ containing oligopeptides.
7. preparation method according to claim 6, it is characterised in that：Using 5 μm of 4.6x of XSelect HSS T3
250mm analytical columns, mobile phase A liquid is 0.1%（V/V）Formic acid-the aqueous solution；Mobile phase B liquid is 0.1% (V/V) formic acid-second
Nitrile solution, column temperature is 40 DEG C, and flow velocity is 1 mL/min, the μ L of sample size 10 of reaction solution, using high performance liquid chromatography to reaction
Liquid carries out gradient elution, and the 7th peak is oligopeptides γ-Glu- γ-Glu- γ-Glu- γ-Glu-val.
8. preparation method according to claim 6, it is characterised in that the concentration of solution GLN and free valine
In 400-1000mmol/L.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107365356A (en) * | 2017-08-25 | 2017-11-21 | 广东真美食品股份有限公司 | Meat products water conservation peptide and its application |
| CN108623660A (en) * | 2018-05-10 | 2018-10-09 | 华南理工大学 | A kind of delicate flavour tetradecapeptide and its maillard reaction product and purposes |
| CN108715597A (en) * | 2018-04-16 | 2018-10-30 | 广东环境保护工程职业学院 | Sweet taste peptide γ-L-Glu-D-Val and the preparation method and application thereof |
| US11659854B2 (en) | 2017-07-13 | 2023-05-30 | Fuji Oil Holdings Inc. | Method for imparting body taste to food |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11659854B2 (en) | 2017-07-13 | 2023-05-30 | Fuji Oil Holdings Inc. | Method for imparting body taste to food |
| CN107365356A (en) * | 2017-08-25 | 2017-11-21 | 广东真美食品股份有限公司 | Meat products water conservation peptide and its application |
| CN108715597A (en) * | 2018-04-16 | 2018-10-30 | 广东环境保护工程职业学院 | Sweet taste peptide γ-L-Glu-D-Val and the preparation method and application thereof |
| CN108623660A (en) * | 2018-05-10 | 2018-10-09 | 华南理工大学 | A kind of delicate flavour tetradecapeptide and its maillard reaction product and purposes |
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Application publication date: 20170901 |
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