CN110498836A - 6 peptide QYPVEK and purposes with ACE and HMG-CoA reductase inhibitory activity - Google Patents
6 peptide QYPVEK and purposes with ACE and HMG-CoA reductase inhibitory activity Download PDFInfo
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- CN110498836A CN110498836A CN201910699406.6A CN201910699406A CN110498836A CN 110498836 A CN110498836 A CN 110498836A CN 201910699406 A CN201910699406 A CN 201910699406A CN 110498836 A CN110498836 A CN 110498836A
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- peptide
- qypvek
- hmg
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- coa reductase
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Abstract
The invention belongs to field of biotechnology, in particular to one can inhibit its activity, can also inhibit active 6 peptide of 3-hydroxy-3-methylglutaric acid list acyl coenzyme A (HMG-CoA) reductase in conjunction with Angiotensin-Converting.The invention discloses a kind of 6 peptide QYPVEK with ACE and HMG-CoA reductase inhibitory activity, the amino acid sequence of 6 peptide QYPVEK are as follows: Gln-Tyr-Pro-Val-Glu-Lys.The present invention further simultaneously discloses above-mentioned 6 peptide QYPVEK and is preparing the application in ace inhibitory peptide and HMG-CoA reductase peptide for inhibiting.
Description
Technical field
The invention belongs to field of biotechnology, in particular to one can inhibit its work in conjunction with Angiotensin-Converting
Property, it can also inhibit active 6 peptide of 3-hydroxy-3-methylglutaric acid list acyl coenzyme A (HMG-CoA) reductase.
Background technique
Angiotensin-Converting (Angiotensin converting enzyme, ACE, EC3.4.15.1, in document
Former name has kininaseIl, dipeptidyl carboxypeptidase I etc.) it is a kind of two carboxypeptidases, it is to lead to high blood
One key enzyme of pressure, hypertensinⅠ is converted to angiotensin II by hydrolysis by it, and at the same time, ACE may be used also
It is passivated bradykinin, both effects can lead to vessel retraction, so as to cause hypertension.Therefore ACE is considered as drawing
Play a key factor of hypertension.It has been investigated that angiotensin converting enzyme inhibitor (ACEI), it can be by inhibiting ACE's
Activity and have the function that blood pressure lowering.Vel-Tyr-Pro-Trp-Thr-Gln-Arg-Phe is widely used in the diseases such as treatment angiocarpy, hypertension, heart failure, kidney failure
Disease.Vel-Tyr-Pro-Trp-Thr-Gln-Arg-Phe is found from snake venom, then it is found that the ace inhibitory peptide extracted from food material, such as bright
Glue, casein, fish, fig natural gum, α-zein etc. all can be used as the raw material for preparing ace inhibitory peptide.
3-hydroxy-3-methylglutaric acid list acyl coenzyme A (HMG-CoA) reductase is internal catalysis 3- hydroxy-3-methyl penta
Diacid list acyl coenzyme A (HMG-CoA) generates the key enzyme of dimethylol pentanoic acid (MVA), this step is internal synthetic cholesterol
Rate-limiting step, and the target spot of most important hyperlipemia clinical medicine at present.HMG-CoA reductase inhibitor is reducing blood lipid function
Imitate one of ingredient and drug screening main means.
The drug of blood pressure lowering common are:
1. diuretics: representing that drug has hydrogen chlorine to bite throat, phenalgin butterfly suckes, tenth of the twelve Earthly Branches purport etc. in spiral shell.
2. opiate receptor retarding agent: representing drug has Pu Cailuoer, metoprolol, atenolol, Nadolol etc..
3. calcium channel blocker: representing drug has nifedipine, Amlodipine, felodipine, nitrendipine, lacidipine
Deng.
4. angiotensin converting enzyme inhibitor: representing drug has captopril, Benazepril, lisinopril, Yi Napu
Benefit, Cilazapril etc..
5. a- receptor blocker: representing drug has croak throat, special drawing mile prolixity etc..
6. Angiotensin Ⅱ receptor antagonist: represent drug have Losartan, pick Sha Tan, Irbesartan, Candesartan, she
Bei Shatan, Telmisartan etc..
The drug of reducing blood lipid has:
1, fibrate: such drug has fenofibrate, Gemfibrozil Capsules, Bezafibrate etc..Fibrate drug drop
Blood fat is strong, rapid-action, and the effect of triglyceride reducing is stronger than the effect of norcholesterol.
2, trihydroxy methyl glutaryl-CoA-reductase inhibitors: such drug has Lovastatin, simvastatin, general cuts down him
Fourth etc..For such drug based on norcholesterol, effect for reducing fat is strong, rapid-action.
3, niacin class: Acipimox is more common in such drug, reduces the effect of serum levels of triglyceride than reducing cholesterol
By force.
4, polyunsaturated fatty acid class: including various plant seed oils.Such as rubber seed oil, seed of Radix Oenotherae erythrosepalae, milk thistle kind
The oil of son and the preparation of ocean fish.This kind of drug plays the role of reducing blood lipid and reduces blood viscosity, but acts on milder.
5, pantethine: for the derivative of coacetylase, having reduces serum cholesterol, triglyceride and increasing high density rouge egg
The effect of white-cholesterol.
6, sodium alginate (PPS): being using seaweed pinch object as the heparan marine drug of raw material.It is viscous to do the long low blood of blood
The effects of degree, expansion blood vessel and reduction blood lipid.It is mainly used for the prevention and treatment of ischemic angiocardiopathy and cerebrovascular disease.
7, other blood lipid-lowering medicines: such as ginkgo class (Tian Bao Ning) experiments have shown that serum levels of triglyceride (TG) can be made significantly to drop
It is low.
Existing drug report, in addition to Chinese medicine, while having the drug of blood pressure lowering and effect for reducing blood fat rarely found.Because this two
The target that kind medicine is acted on is different.
Summary of the invention
Have blood pressure lowering and reducing blood lipid difunctional the technical problem to be solved in the present invention is to provide a kind of duck protein sources
6 peptide sequence QYPVEK and application thereof.
In order to solve the above technical problem, the present invention provides a kind of 6 with ACE and HMG-CoA reductase inhibitory activity
Peptide QYPVEK, the amino acid sequence of 6 peptide QYPVEK are as follows: Gln-Tyr-Pro-Val-Glu-Lys.
The present invention goes back while providing above-mentioned 6 peptide QYPVEK in preparing ace inhibitory peptide and HMG-CoA reductase peptide for inhibiting
Application.
6 peptide QYPVEK of the invention can be obtained by the synthesis of commission gill biochemistry (Shanghai) Co., Ltd..
6 peptide sequences that the present invention is reported are to all have inhibitory activity for two targets of ACE and HMG-CoA reductase,
To show to have simultaneously blood pressure lowering and the difunctional characteristic of reducing blood lipid.
The potential specific objective active peptide that contains in different peptide section sequences is different, in the same enzyme or the work of enzyme not of the same race
Obtained peptide sequence is different under.The present invention derives from Chinese duck (NCBI Reference Sequence:NP_
001297320.1, Molecular cloning of the perilipin gene and its association with
Carcass and fat traits in Chinese ducks.Genet.Mol.Res.2013,12 (2), 1582-1592) egg
White, the gene and meat quality for expressing the albumen have correlation.The present invention is obtained by the virtual zymolysis technique of area of computer aided
Under the action condition of pepsin (pH≤1.3), gained has ACE inhibitory activity and HMG-CoA reductase inhibitory activity
Peptide.
Items detection method involved in the present invention is specific as follows:
1, the detection method of ACE inhibitory activity:
For ACE at 37 DEG C, the analogies Hippuryl-L- of angiotensin I is catalytically decomposed in pH value under conditions of being 8.3
Histidyl-L-Leucine (HHL) generates hippuric acid (HA), which has characteristic absorption peak at ultraviolet 225nm；When adding
ACE is suppressed the catalyticing decomposition action of HHL when entering Vel-Tyr-Pro-Trp-Thr-Gln-Arg-Phe, and the production quantity of hippuric acid is reduced, by HPLC method,
The variation that the amount of the generated hippuric acid in inhibitor front and back is added in measurement can calculate the size of inhibitory activity.
Reaction system are as follows: be successively separately added into the ACE of 20 μ L 0.1U/mL, 50 μ L ace inhibitory peptides (i.e. QYPVEK6 peptide,
Small peptide inhibitor) in 37 DEG C of warm bath 5min, the catalysis reaction of the HHL substrate starting ACE of 10 μ L 5mM is then added, shakes at 37 DEG C
It swings and the HCl of 250 μ L 1.0moL/L is added after water-bath 30min terminates reaction, system solution carries out RP- after crossing 0.45 μm of filter membrane
HPLC tests and analyzes the content of hippuric acid (HA).Above-mentioned similarity condition, (to contain in the borate buffer of 50 μ L 0.1moL/L
The NaCl of 0.3moL/L, pH=8.3) replace Vel-Tyr-Pro-Trp-Thr-Gln-Arg-Phe as blank reaction system.
Note: above-mentioned ACE, HHL substrate is with the borate buffer of 0.1moL/L (NaCl containing 0.3moL/L, pH=
It 8.3) is solvent.
Ace inhibitory peptide (QYPVEK6 peptide) is dissolved in the borate buffer of 0.1moL/L with various concentration (containing 0.3moL/
The NaCl of L, pH=8.3) in and obtain.
RP-HPLC detection: solvent I is the triethylamine (TTA) of 0.05% (V/V) trifluoroacetic acid (TFA) and 0.05% (v/v)
It is dissolved in deionized water, the chromatographically pure second eyeball that solvent II is 100%.The ratio of solvent I and solvent II is 70%:30% (volume
Than), flow velocity 0.5mL/min, Detection wavelength 225nm, detection column temperature are 30 DEG C.
ACE inhibitory activity calculates according to the following formula:
I%=(A-B)/A × 100%
A: the peak area of hippuric acid when being added without small peptide inhibitor；
B: the peak area of hippuric acid when addition small peptide inhibitor；
ACE:1U unit definition is, under Standard Test Conditions, the catalysis substrate (Hippuryl- in 37 DEG C, the 1min time
L-Histidyl-L-Leucine, HHL), generate the amount of 1 μM of consumed ACE of hippuric acid.That is, being the active unit of ACE.
2, the external detection method of reducing blood lipid peptide activity:
Chromatographic condition
C18Chromatographic column (5 μm, 4.6mm × 250mm).Mobile phase are as follows: V (K2HPO4-KH2PO4): V (methanol)
=85:15, pH 7.2, isocratic elution, flow velocity 1mL/min；Detection wavelength 337nm；20 μ L of sample volume；25 DEG C of column temperature.
Reaction system experimental procedure
200 μ are added in the additional amount of various components and sequence such as table 1,37 DEG C of water-baths of reaction temperature after the reaction was completed in reaction
L 0.5mol/L NaOH solution terminates reaction, by the concentration of NADPH in above-mentioned chromatographic condition measurement sample.Reaction time root
It is determined according to enzyme control group time gradient.
1 reaction system constituent of table
Remarks illustrate: reaction buffer is the kaliumphosphate buffer of 0.1mol/L, and the concentration of HMGR solution is 6.56 μ g/
ML, HMG-CoA solution concentration are 5.23mmol/mL, and NADPH solution concentration is 1mg/mL.
The calculating of experimental result
After inhibitor is added, the activity of HMG-CoA reductase is suppressed, and the amount of substrate reactions is reduced.Therefore, Ke Yili
The variation of reaction front and back NADPH amount is measured with HPLC to evaluate inhibitor to the inhibiting rate of HMG-CoA reductase.Calculation formula
Are as follows:
R=(SInhibitor-SControl)/(SBlank-SControl)×100
In formula, R is inhibiting rate (%)；SBlank、SControlAnd SInhibitorRespectively in blank group, enzyme control group and inhibitor group
The peak area (mAU.min) of NADPH.
The advantages and positive effects of the present invention:
(1) 6 peptide molecule can inhibit the activity of Angiotensin-Converting.
(2) ace inhibitory peptide of the invention (or referred to as 6 peptide QYPVEK) has HMG-CoA reductase inhibitory activity simultaneously.
The usage and dosage of ace inhibitory peptide of the invention and HMG-CoA reductase peptide for inhibiting (or referred to as 6 peptide QYPVEK)
It is as follows:
6 peptides of the invention are oral type, and dosage is oral, each 1.5g, daily 2~3 times.
Specific embodiment
Embodiment 1,
ACE inhibitory activity of the 6 peptide QYPVEK under the concentration of 1.0mg/mL:
Chromatographic condition: solvent I is dissolved in deionized water for the triethylamine (TTA) of 0.05% trifluoroacetic acid (TFA) and 0.05%
In (i.e. the triethylamine of the trifluoroacetic acid containing 0.5mL and 0.5mL in every liter of solvent I), solvent II be 100% chromatographically pure second
Eyeball.The ratio of solvent I and solvent II is 70%:30% (volume ratio), and ultimate3000 wears peace liquid chromatograph, and chromatographic column is
watersSymmetry C185 μm of 4.6 × 250mm, flow velocity 0.5mL/min, sample volume 10 μ L, Detection wavelength 225nm,
Detecting column temperature is 30 DEG C.
Detection method: will obtain this 6 peptide QYPVEK structure by chemical synthesis, and carrying out Activity determination, (detection method is same
On).QYPVEK concentration is 1.0mg/mL at this time.
As a result: ACE inhibitory activity of the 6 peptide QYPVEK in 1.0mg/mL is 83.28%.
HMG-CoA reductase inhibitory activity of the 6 peptide QYPVEK under the concentration of 1.0mg/mL:
Chromatographic condition:C18Chromatographic column (5 μm, 4.6mm × 250mm).Mobile phase are as follows: V (K2HPO4-
KH2PO4): V (methanol)=85:15, pH 7.2, isocratic elution, flow velocity 1mL/min；Detection wavelength 337nm；20 μ L of sample volume；Column
25 DEG C of temperature.
Detection method: will obtain this 6 peptide QYPVEK by chemical synthesis, carry out Activity determination (detection method is same as above).
QYPVEK concentration is 1.0mg/mL at this time.
As a result: HMG-CoA reductase inhibitory activity of the 6 peptide QYPVEK in 1.0mg/mL is 77.35%.
Embodiment 2,
ACE inhibitory activity of the 6 peptide QYPVEK under the concentration of 2.0mg/mL:
Chromatographic condition: solvent I is dissolved in deionized water for the triethylamine (TTA) of 0.05% trifluoroacetic acid (TFA) and 0.05%
In；The chromatographically pure second eyeball that solvent II is 100%.The ratio of solvent I and solvent II is 70%:30%, and ultimate3000 wears peace
Liquid chromatograph, chromatographic column are waters Symmetry C185 μm of 4.6 × 250mm, flow velocity 0.5mL/min, sample volume 10
μ L, Detection wavelength 225nm, detection column temperature are 30 DEG C.
Detection method: will obtain this 6 peptide by chemical synthesis, carry out Activity determination (detection method is same as above).DA at this time
Concentration is 2.0mg/mL.
As a result: ACE inhibitory activity of the 6 peptide QYPVEK in 2.0mg/mL is 93.14%.
HMG-CoA reductase inhibitory activity of the 6 peptide QYPVEK under the concentration of 2.0mg/mL:
Chromatographic condition:C18Chromatographic column (5 μm, 4.6mm × 250mm).Mobile phase are as follows: V (K2HPO4-
KH2PO4): V (methanol)=85:15, pH 7.2, isocratic elution, flow velocity 1mL/min；Detection wavelength 337nm；20 μ L of sample volume；Column
25 DEG C of temperature.
Detection method: will obtain this 6 peptide QYPVEK by chemical synthesis, carry out Activity determination (detection method is same as above).
QYPVEK concentration is 2.0mg/mL at this time.
As a result: HMG-CoA reductase inhibitory activity of the 6 peptide QYPVEK in 2.0mg/mL is 90.06%.
By the inhibition concentration and activity data in embodiment 1 and embodiment 2, illustrate the activity and concentration of this 6 peptide structure
There are dose-effect relationship, there is this 6 peptide structure ACE inhibitory activity and HMG-CoA reductase inhibition to have not been reported simultaneously, belong to new
Have both the bifunctional peptide of ACE inhibitory activity and HMG-CoA reductase inhibitory activity.
The above list is only a few specific embodiments of the present invention for finally, it should also be noted that.Obviously, this hair
Bright to be not limited to above embodiments, acceptable there are many deformations, such as the QYPVEK knot that different proteins source is degraded separating obtained
Structure and its derivatization structure.The institute that those skilled in the art directly can export or associate from present disclosure
There is deformation, is considered as protection scope of the present invention.
Sequence table
<110>Zhejiang Academy of Agricultural Science
<120>with the 6 peptide QYPVEK and purposes of ACE and HMG-CoA reductase inhibitory activity
<160> 1
<170> SIPOSequenceListing 1.0
<210> 1
<211> 6
<212> PRT
<213>artificial sequence (Artificial Sequence)
<400> 1
Gln Tyr Pro Val Glu Lys
1 5
Claims (2)
1. the 6 peptide QYPVEK with ACE and HMG-CoA reductase inhibitory activity, it is characterized in that: the amino of the 6 peptide QYPVEK
Acid sequence are as follows: Gln-Tyr-Pro-Val-Glu-Lys.
2. 6 peptide QYPVEK as described in claim 1 is preparing the application in ace inhibitory peptide and HMG-CoA reductase peptide for inhibiting.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201910699406.6A CN110498836A (en) | 2019-07-31 | 2019-07-31 | 6 peptide QYPVEK and purposes with ACE and HMG-CoA reductase inhibitory activity |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201910699406.6A CN110498836A (en) | 2019-07-31 | 2019-07-31 | 6 peptide QYPVEK and purposes with ACE and HMG-CoA reductase inhibitory activity |
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| Publication Number | Publication Date |
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| CN110498836A true CN110498836A (en) | 2019-11-26 |
Family
ID=68586829
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| CN201910699406.6A Withdrawn CN110498836A (en) | 2019-07-31 | 2019-07-31 | 6 peptide QYPVEK and purposes with ACE and HMG-CoA reductase inhibitory activity |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101557726A (en) * | 2006-11-02 | 2009-10-14 | 可口可乐公司 | High-potency sweetener composition with Rubisco protein, Rubiscolin, Rubiscolin derivatives, ACE inhibitory peptides, and combinations thereof, and compositions sweetened therewith |
| CN103755783A (en) * | 2013-12-30 | 2014-04-30 | 浙江省农业科学院 | Dipeptide QD with double functions of lowering blood pressure and lowering blood fat and application thereof |
| CN105002250A (en) * | 2015-08-14 | 2015-10-28 | 重庆都好生物科技有限公司 | Method for preparing ACEIP (angiotensin converting enzyme inhibitory peptide) by using duck bones |
-
2019
- 2019-07-31 CN CN201910699406.6A patent/CN110498836A/en not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101557726A (en) * | 2006-11-02 | 2009-10-14 | 可口可乐公司 | High-potency sweetener composition with Rubisco protein, Rubiscolin, Rubiscolin derivatives, ACE inhibitory peptides, and combinations thereof, and compositions sweetened therewith |
| CN103755783A (en) * | 2013-12-30 | 2014-04-30 | 浙江省农业科学院 | Dipeptide QD with double functions of lowering blood pressure and lowering blood fat and application thereof |
| CN105002250A (en) * | 2015-08-14 | 2015-10-28 | 重庆都好生物科技有限公司 | Method for preparing ACEIP (angiotensin converting enzyme inhibitory peptide) by using duck bones |
Non-Patent Citations (6)
| Title |
|---|
| GRIET HERREGODS等: "Angiotensin I-converting enzyme inhibitory activity of gelatin hydrolysates and identification of bioactive peptides", 《J AGRIC FOOD CHEM》 * |
| MARTA GALLEGO等: ""The relevance of dipeptides and tripeptides in the bioactivity and taste of dry-cured ham", 《FOOD PRODUCTION, PROCESSING AND NUTRITION》 * |
| 于志鹏等: "肽组学在食源性活性肽研究中应用的进展", 《于志鹏等》 * |
| 吴杲等主编: "《科学合理用药》", 31 January 2013, 科学技术文献出版社 * |
| 崔春编著: "《食物蛋白质控制酶解技术》", 30 June 2018, 中国轻工业出版社 * |
| 王晓丹等: "ACE抑制肽构效关系研究进展", 《食品科学》 * |
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