CN110484582A - Savoury peptide and preparation method thereof in soy sauce - Google Patents
Savoury peptide and preparation method thereof in soy sauce Download PDFInfo
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- CN110484582A CN110484582A CN201910736864.2A CN201910736864A CN110484582A CN 110484582 A CN110484582 A CN 110484582A CN 201910736864 A CN201910736864 A CN 201910736864A CN 110484582 A CN110484582 A CN 110484582A
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- soy sauce
- savoury
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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
-
- 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
- A23L27/50—Soya sauce
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/14—Extraction; Separation; Purification
- C07K1/16—Extraction; Separation; Purification by chromatography
- C07K1/18—Ion-exchange chromatography
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/14—Extraction; Separation; Purification
- C07K1/34—Extraction; Separation; Purification by filtration, ultrafiltration or reverse osmosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/14—Extraction; Separation; Purification
- C07K1/36—Extraction; Separation; Purification by a combination of two or more processes of different types
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1021—Tetrapeptides with the first amino acid being acidic
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P21/00—Preparation of peptides or proteins
- C12P21/02—Preparation of peptides or proteins having a known sequence of two or more amino acids, e.g. glutathione
Abstract
The present invention relates to the preparation method and applications of savoury peptide in soy sauce.The present invention, by koji-making, fermentation, obtains soy sauce crude oil using dregs of beans and wheat flour as raw material, then soy sauce crude oil is crossed the ultrafiltration membrane that molecular weight is 5000Da, takes permeate.It to permeate using the savoury peptide in Oasis MAX mixed type anion solid-phase extraction column enrichment soy sample, is identified by UPLC-MS/MS, amino acid sequence is γ-Glu-Ser-Ala-Tyr.The savoury peptide has preferable flavor intensity, the savoury of food is remarkably improved under the concentration of 300ppm, therefore can be widely applied to the fields such as food and flavouring.
Description
Technical field
The present invention relates to the use of dregs of beans and wheat flour preparation has the savoury peptide and purposes of obvious savoury, belongs to food
Field of biotechnology.
Background technique
It makes soy sauce and is not only a kind of liquid flavoring that color is various, and a kind of large albumen full of nutrition
Fermented food.In soy sauce, containing there are many nutrition such as amino acid, organic acid, sugar, minerals, vitamin necessary to human body
Substance, there are also flavor abundant, fragrance and coloring matters.Not a kind of single substance of soy sauce, the change of hundreds of complexity
It learns material mixing to form, there is special, various flavor.Due to fermentation raw material, raw material proportioning, strain, zymotechnique and condition
Difference, the ingredient in soy sauce has very big difference, to influence the quality of soy sauce.
Savoury peptide in soy sauce is mainly derived from the product of soybean protein and wheat gluten synthesis and decomposition, can be effective
Improve the small molecule peptide matters (usually less than 5kDa) of flavour of food products, including sweet taste peptide, bitter peptides, tart flavour peptide, saline taste
Peptide, delicate flavour peptide and savoury peptide etc..Wherein, delicate flavour peptide is important one of savoury peptide, is widely present in vegetable food, animality
Food, fermented product such as soy sauce, beans sauce, shrimp paste, ham, in peanut food, have significant fresh adding, flavouring effect at fermented bean curd.
As people's living standard improves, extensively to the concern of flavor and research, Japanese scholars propose it is a kind of it is new, different from traditional
The sense of taste " kokumi ", i.e. savoury, for describing the dense sense of food, persistence, complicated rich, plentiful mouthfeel etc..20th century
The nineties, Japanology scholar Ueda etc., which is separated and identified from the water extract of garlic and onion, can increase dense sense and hold
The key substance γ-Glutamyl Peptide spent long.Savoury peptide can be with other 5 kinds of basic tastes in coordination food system, significant increasing
Add the dense sense of food, complexity etc..
In fact, all containing in the foods such as cheese, onion, garlic, scallop, soy sauce, fish sauce, mung bean, Kidney bean or fermented food
There is dense sense peptide, and content distribution is also different in different food products.Kuroda etc. passes through high performance liquid chromatography-tandem mass (LC/
MS/MS) and Derivative is to γ-Glu-Val-Gly in commercially available 6 kinds dark soy sauce, 2 kinds of light soy sauce and a kind of white soy sauce
Content studied, the results showed that γ-Glu-Val-Gly is widely present in soy sauce, and content is in 0.15~0.61mg/dL
In range.Kuroda etc. also found dense sense peptide γ-Glu-Val-Gly in Vietnam, Thailand, China, South Korea, Japan and meaning
The commodity fish sauce of big benefit different sources is widely present, and content is about 0.04~1.26mg/dL.Identification is separated in yeast extract
Dense sense peptide γ-Glu-Cys and Glu-Cys-Gly out, content is respectively 3.29~50.20mg/g and 0.57~5.00mg/g.
For Toelstede etc. in terms of dry mass, research finds that γ-Glutamyl Peptide total content is about 89.36 μm of ol/kg in up to cheese, and
The total content of γ-Glutamyl Peptide can reach 3.59mmol/kg in blue cheese.
With the taste compound of other in food system synergistic function can occur for dense sense peptide.By γ-glutamyl peptide
It is added in delicate flavour solution, various tastes can be coordinated, significantly increase dense sense, the complexity of system, while is substantially reduced γ-
The threshold value of glutamyl peptide.In addition, pH value also has an impact to the intensity of dense peptide.The different pH value of the research such as Toelstede (4.7,
5.7,6.7,7.7) influence for feeling intensity dense to γ-Glutamyl Peptide, the results showed that the intensity of dense sense peptide is in near-neutral pH 6.7
When it is most strong, take second place in faintly acid pH5.7, it is most weak in acid (pH4.7) and alkalescent (pH7.7).The calcium of γ-Glutamyl Peptide
Quick receptor (CaSR) and the intensity of dense sense peptide are positively correlated.The specific inhibitor of the researchs such as Kuroda discovery addition CaSR
(NPS-2143) the dense sense intensity of glutamyl peptide (Glu-Cys-Gly and γ-Glu-Val-Gly) can be significantly reduced, as a result
Show that CaSR receptor participates in the perception of dense sense peptide.
However, so far, there is not yet from soy sauce, hydrolysate of soybean protein product, wheat or wheat gluten protein hydrolysate,
Separation identifies the savoury with amino acid sequence γ-Glu-Ser-Ala-Tyr in wheat or wheat gluten protein tunning
The report of peptide.
Summary of the invention
The purpose of the present invention is to provide a kind of savoury peptide (γ-from soy sauce with stronger savoury humidification
Glu-Ser-Ala-Tyr preparation method and applications).
Inventor is found to have the savoury peptide from soy sauce of γ-Glu-Ser-Ala-Tyr primary structure in 200mg/
The savoury of food is remarkably improved under the concentration of kg.
A kind of preparation method of savoury peptide, it is characterised in that the method steps are as follows:
(1) it after dregs of beans and wheat flour mix, is handled through extrusion, is inoculated with dregs of beans and wheat flour weight after cooling
The song essence of 0.02%-0.20% (w/w), koji-making obtain into song；
(2) yeast and 2-3 times of salt water are mixed, is fermented using high-salt dilute soy brewing method (GB18186-2000)
After -90 days 60 days, glutaminase is added, continues fermentation to -30 days 10 days, heat treatment, squeezing, filtering obtain soy sauce original
Liquid.
(3) soy sauce stoste is crossed into the ultrafiltration membrane that molecular weight is 5000Da, takes permeate；
(4) it will transmit through liquid by OasisMAX mixed type anion solid-phase extraction column, successively use deionized water and acetic acid
Eluent takes acetic acid eluent, obtains the tunning rich in γ-Glu-Ser-Ala-Tyr.
Qu Jingwei described in step (1) derives from aspergillus oryzae or Aspergillus sojae.
The weight ratio of dregs of beans described in step (1) and wheat is 4:1-1:1.
In step (1), the koji-making condition are as follows: the temperature of culture is 28 DEG C~35 DEG C, and humidity is 70%~90%, training
Supporting the time is 42h~72h.
In step (1), the pressurization swelling temperature is 140 DEG C~150 DEG C.
In step (2), the addition quality of the glutaminase is the 0.002%-0.05% (g/ of soy sauce crude oil volume
mL)。
90~100 DEG C of 10~30min of enzyme deactivation of heat treatment condition described in step (2).
In step (4), acetic acid concentration is 5%-10% (g/100mL) in the acetic acid eluent
The application of savoury peptide γ-Glu-Ser-Ala-Tyr and its salt in flavouring, frozen food, instant food.
Savoury peptide concentration in food is 200mg/kg or more to improve food savoury, reduces saline taste.
Compared with the prior art, the invention has the following advantages:
(1) the flavor intensity of savoury peptide provided by the invention is higher, is remarkably improved food in the concentration of 200mg/kg
Savoury can be widely applied in flavouring, dilated food and frozen food；
(2) primary structure of savoury peptide γ-Glu-Ser-Ala-Tyr is to report for the first time.
Detailed description of the invention
Fig. 1 is the mass spectrogram of γ-Glu-Ser-Ala-Tyr.
Fig. 2 is the appearance time comparison diagram of γ-Glu-Ser-Ala-Tyr and Glu-Ser-Ala-Tyr in the liquid phase.
Specific embodiment
Embodiment 1
(1) after dregs of beans and wheat flour are mixed by weight 1:1, through handling in 140 DEG C of extrusions, dregs of beans is inoculated with after cooling
With the bent essence of aspergillus oryzae of wheat flour weight 0.02% (w/w), the temperature of culture is 28 DEG C, humidity 70%, incubation time 42h
Koji-making obtains into song；
(2) yeast and 2 times of salt water are mixed, using high-salt dilute soy brewing method (GB18186-2000) fermentation 60
After it, the glutaminase of 0.002% (g/mL) is added, continues fermentation to 30 days, heat treatment, squeezing, filtering obtain soy sauce original
Liquid.
(3) soy sauce stoste is crossed into the ultrafiltration membrane that molecular weight is 5000Da, takes permeate；
(4) it will transmit through liquid by OasisMAX mixed type anion solid-phase extraction column, successively use deionized water and 5%
(g/100mL) acetic acid eluent takes acetic acid eluent, obtains the tunning rich in γ-Glu-Ser-Ala-Tyr.
Qualitative and quantitative detection is carried out to the tunning that will be enriched in γ-Glu-Ser-Ala-Tyr using UPLC-MS/MS method,
Analysis condition is as follows: using 1290 type superelevation phase liquid chromatograph of Agilent series connection Brooker maXis type second order ms instrument to each
A reaction solution is analyzed.Select Agilent ZORBAXRRHDSB-C18 column (2.1mm × 50mm, 1.8 μm, 30 DEG C) to product
It is separated, mobile phase is 0.1% formic acid-acetonitrile solution (A) and 0.1% formic acid-aqueous solution (B), gradient elution program are as follows: first
First A:B=100:0 continues 5min, becomes A:B=90:10, continues 5min, and become A:B=85:15；Continue 2min, finally
A:B=100:0 is returned to, sample volume is 5 μ L.Mass Spectrometry Conditions: high-resolution connect quadrupole rod mass spectrometer, electron spray (ESI) from
Component, positive ion mode, full wavelength scanner, range
For 50~1500m/z；Electron spray voltage (IS): 4500V；Capillary temperature: 180 DEG C；Atomization pressure: 0.3bar.
The mass spectrogram of γ-Glu-Ser-Ala-Tyr is shown in Fig. 1.Since UPLC-MS/MS method can not judge the connection of savoury peptide
Mode, therefore the structure of Fig. 1 may be γ-Glu-Ser-Ala-Tyr or Glu-Ser-Ala-Tyr.Utilize synthesis in solid state
Method has manually been respectively synthesized the γ-Glu-Ser-Ala-Tyr and Glu-Ser-Ala-Tyr that 1g purity is 99%.Compare γ-
The appearance time of Glu-Ser-Ala-Tyr and Glu-Ser-Ala-Tyr in the liquid phase confirms the savoury that this assessment of result comes out
Peptide is γ-Glu-Ser-Ala-Tyr, sees Fig. 2.
Embodiment 2
(1) after dregs of beans and wheat flour are mixed by weight 4:1, through handling in 150 DEG C of extrusions, dregs of beans is inoculated with after cooling
With the bent essence of aspergillus oryzae of wheat flour weight 0.2% (w/w), the temperature of culture is 30 DEG C, humidity 90%, incubation time 72h
Koji-making obtains into song；
(2) yeast and 3 times of salt water are mixed, using high-salt dilute soy brewing method (GB18186-2000) fermentation 90
After it, the glutaminase of 0.05% (g/mL) is added, continues fermentation to 20 days, heat treatment, squeezing, filtering obtain soy sauce original
Liquid.
(3) soy sauce stoste is crossed into the ultrafiltration membrane that molecular weight is 5000Da, takes permeate；
(4) it will transmit through liquid by OasisMAX mixed type anion solid-phase extraction column, successively use deionized water and 8%
(g/100mL) acetic acid eluent takes acetic acid eluent, obtains the tunning rich in γ-Glu-Ser-Ala-Tyr.
Embodiment 3
(1) after dregs of beans and wheat flour are mixed by weight 2:1, through handling in 160 DEG C of extrusions, dregs of beans is inoculated with after cooling
With the bent essence of aspergillus oryzae of wheat flour weight 0.02% (w/w), the temperature of culture is 32 DEG C, humidity 80%, incubation time 42h
Koji-making obtains into song；
(2) yeast and 2.5 times of salt water are mixed, using high-salt dilute soy brewing method
(GB18186-2000) after fermenting 80 days, the glutaminase of 0.01% (g/mL) is added, is continued to ferment to 10 days,
Heat treatment, squeezing, filtering, obtain soy sauce stoste.
(3) soy sauce stoste is crossed into the ultrafiltration membrane that molecular weight is 5000Da, takes permeate；
(4) it will transmit through liquid by OasisMAX mixed type anion solid-phase extraction column, successively use deionized water and 10%
(g/100mL) acetic acid eluent takes acetic acid eluent, obtains the tunning rich in γ-Glu-Ser-Ala-Tyr.
Embodiment 4
The flavor effect assessment of savoury peptide γ-Glu-Ser-Ala-Tyr
Sensory evaluation is used for using the γ-Glu-Ser-Ala-Tyr that solid-phase synthesis synthesis purity is 99%.
Fresh Grade Breast is blended, is put into 12 times of weight clear water, 30min is kept the temperature after boiling, freezing dispels chicken fat, filters clearly
Chicken soup.The salt of chicken soup quality 0.5% is added, the γ-of 100mg/kg, 200mg/kg and 400mg/kg are added in chicken soup
Glu-Ser-Ala-Tyr is tasted in room temperature.Sensory evaluation experiment by have within 28-42 year old 8 males of sensory evaluation experience with
9 women compositions.Analyses Methods for Sensory Evaluation Results shows: the savoury for adding the chicken soup of the γ-Glu-Ser-Ala-Tyr of 200mg/kg is obvious
It improves.
Add 0.3% (m/v) monosodium glutamate, 100mg/kg, 200mg/ respectively in the salt solution of 0.5% (m/v)
The savoury peptide of kg400mg/kg synthesis, the γ-Glu-Ser-Ala-Tyr for studying synthesis analyze the flavor characteristic of its savoury peptide.Knot
Fruit shows the γ-Glu-Ser-Ala-Tyr of synthesis when 200mg/L γ-Glu-Ser-Ala-Tyr coexists with monosodium glutamate, salt
When, show apparent savoury humidification.
Embodiment 5
The sensory effects of the inhibition saline taste of savoury peptide γ-Glu-Ser-Ala-Tyr are evaluated
Sensory evaluation is used for using the γ-Glu-Ser-Ala-Tyr that solid-phase synthesis synthesis purity is 99%.Soy sauce crude oil
It is provided by Foshan Haitian seasonings Food Co, salt content 17.8g/100g, ammonia nitrogen content 1.02g/
100g, total nitrogen content 1.52g/100g, content of reducing sugar 3.45g/100g, total acid content 1.2g/100g.
γ-the Glu- of 100mg/kg, 200mg/kg, 300mg/kg and 400mg/kg synthesis is added in 100g soy sauce respectively
Ser-Ala-Tyr taste in room temperature the saline taste and delicate flavour of soy sauce.The sensory evaluation of saline taste and delicate flavour was tested by 28-42 years old
It is made of 8 males and 9 women of sensory evaluation experience.Analyses Methods for Sensory Evaluation Results shows: the γ-of addition 300mg/kg synthesis
After Glu-Ser-Ala-Tyr, the saline taste of soy sauce is substantially reduced, and delicate flavour improves.
Claims (10)
1. a kind of preparation method of savoury peptide, it is characterised in that the method steps are as follows:
(1) it after dregs of beans and wheat flour mix, is handled through extrusion, is inoculated with dregs of beans and wheat flour weight 0.02%- after cooling
The song essence of 0.20% (w/w), koji-making obtain into song；
(2) yeast and 2-3 times of salt water are mixed, using high-salt dilute soy brewing method (GB18186-2000) fermentation 60 days-
After 90 days, glutaminase is added, continues fermentation to -30 days 10 days, heat treatment, squeezing, filtering obtain soy sauce stoste.
(3) soy sauce stoste is crossed into the ultrafiltration membrane that molecular weight is 5000Da, takes permeate；
(4) it will transmit through liquid by Oasis MAX mixed type anion solid-phase extraction column, successively eluted using deionized water and acetic acid
Liquid takes acetic acid eluent, obtains the tunning rich in γ-Glu-Ser-Ala-Tyr.
2. a kind of preparation method of soy sauce described in claim 1, it is characterised in that dregs of beans described in step (1) and wheat
Weight ratio is 4:1-1:1.
3. a kind of preparation method of soy sauce described in claim 1, it is characterised in that Qu Jingwei described in step (1) is derived from
Aspergillus oryzae or Aspergillus sojae.
4. a kind of preparation method of soy sauce according to claim 1, which is characterized in that in step (1), the koji-making condition
Are as follows: the temperature of culture is 28 DEG C~35 DEG C, and humidity is 70%~90%, and incubation time is 42h~72h.
5. a kind of preparation method of soy sauce according to claim 1, which is characterized in that in step (1), the pressurization extruding
Temperature is 140 DEG C~150 DEG C.
6. a kind of preparation method of savoury peptide according to claim 1, which is characterized in that in step (2), the glutamy
The addition quality of amine enzyme is the 0.002%-0.05% (g/mL) of soy sauce crude oil volume.
7. 90~100 DEG C of 10~30min of enzyme deactivation of heat treatment condition described in claim 3 step (2).
8. a kind of preparation method of savoury peptide according to claim 1, which is characterized in that in step (4), the acetic acid is washed
Acetic acid concentration is 5%-10% (g/100mL) in de- liquid.
9. the application of savoury peptide γ-Glu-Ser-Ala-Tyr and its salt in flavouring, frozen food, instant food.
10. the concentration in food of savoury peptide described in claim 1 is 200mg/kg or more to improve food savoury, saline taste is reduced.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113632963A (en) * | 2021-07-09 | 2021-11-12 | 佛山市海天(高明)调味食品有限公司 | Thick soy sauce and preparation method thereof |
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| CN113632963A (en) * | 2021-07-09 | 2021-11-12 | 佛山市海天(高明)调味食品有限公司 | Thick soy sauce and preparation method thereof |
| CN113632963B (en) * | 2021-07-09 | 2023-06-27 | 佛山市海天(高明)调味食品有限公司 | Concentrated soy sauce and preparation method thereof |
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