CN104762358A - Rapid preparation method of mussel protein antihypertensive peptide - Google Patents
Rapid preparation method of mussel protein antihypertensive peptide Download PDFInfo
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Abstract
The invention discloses a rapid preparation method of a mussel protein antihypertensive peptide. The antihypertensive peptide is characterized in that an amino acid sequence of the antihypertensive peptide is Val-Ser-Trp-Pro-Cys-Arg-Trp(VSWPCRW); the molecular weight determined by ESI-MS (electrospray ionization mass spectrometry) is 935.07Da. The active peptide Val-Ser-Trp-Pro-Cys-Arg-Trp is obtained by shelling mussels, taking the meat of the mussels, carrying out enzymolysis on the meat, carrying out ultrafiltration on the enzymatic hydrolysate, adsorbing the enzymatic hydrolysate with an agarose magnetic microsphere immobilized ACE (angiotensin converting enzyme) and carrying out purification by RP-HPLC (reversed-phase high-performance liquid chromatography). The active peptide prepared by the invention has obvious ACE inhibitory activity and can be used in hypertension treatment related drugs.
Description
Technical field
The invention belongs to technical field of bioengineering, be specifically related to a kind of fast preparation method of mussel protein Antihypertensive Peptides.
Background technology
Angiotensin-converting enzyme (ACE) is also called peptidyl-carboxypeptidase or kininaseⅡ, and molecular weight is 150,000 Da, belongs to endothelial cellular membrane desmoenzyme.The angiotensinⅠ of decapeptide can be hydrolyzed into the angiotensinⅡ of octapeptide by ACE, impels blood vessel to shrink further, causes elevation of blood pressure.Meanwhile, ACE also promotes the secretion of aldosterone by acting on adrenal cortex.Therefore, ACE is the important component of Re-A-A (RAS).In addition, ACE catalysis can also have the bradykinin hydrolysis of hypotensive effect and makes it lose activity.Therefore, find the material of ACE activity in suitable suppression body, just can reach the object reducing or control blood pressure.
Angiotensin-convertion enzyme inhibitor (ACEI) is that a class develops antihypertensive drug rapidly, it is mainly through suppressing ACE active, cause angiotensinⅠ not to be converted to angiotensinⅡ, suppress ACE to the deactivation of bradykinin simultaneously, thus produce pressure reduction effect.Conventional angiotensin-convertion enzyme inhibitor (ACEI) mostly is chemicals, as captopril (Captopril), alacepril (Alacepril), lisinopril (Lisinopril) and fosinopril (Fosinopril) etc. clinically.But, there is more side effect in this type of chemical synthetic drug process of clinical application, as granulocytopenia, cough, fash, heating and parageusia etc., bring certain misery to patient.
At present, ACE inhibitory activity peptide (ACEP) is subject to extensive concern due to its significant physiologically active, compared with the ACEI of chemosynthesis, the advantage of ACEP is mainly reflected in: (1) adopts food grade protease hydrolysis to prepare, security is high, toxic side effect is little, and multiple ACEP experimentation on animals and clinical test results, do not observe obvious toxic-side effects; (2) food protein raw material sources are wide, and enzyme-squash techniqued mild condition, is easy to industrialization; (3) ACEP antihypertensive effect is single-minded, and low being easier to of molecular weight is digested and assimilated.Therefore, research and develop out the bioactive peptide food or medicine with hypotensive activity, become an important channel of fishery products efficiency utilization.
In recent years, magnetic microsphere causes extensive attention as the research of fixed enzyme vector.And adopting " emulsification compounding technology " to carry out modification to agarose, the Agarose Magnetic Microsphere of preparation has following remarkable advantage: (1) has magnetic, can be separated rapidly under the action of a magnetic field; (2) good biocompatibility; (3) surface is containing a large amount of functional group, high adsorption capacity; (4) dispersed and good stability.Adopt Agarose Magnetic Microsphere do carrier, the magnetic microsphere immobilized ACE of preparation, in the solution can with ACEP specific adsorption, can be separated with enzymolysis solution rapidly again under the action of a magnetic field.But investigator finds not yet there is the research utilizing this technology to prepare Antihypertensive Peptides from mussel zymolyte at present.
Based on this, the present invention adopts zymolysis technique degraded mussel protein, and utilize ultrafiltration, magnetic microsphere immobilized ACE adsorbs and high-efficient liquid phase chromatogram technology prepares Antihypertensive Peptides, the higher value application for mussel provides a new approach.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of fast preparation method angiotensin-converting enzyme (ACE) to significant inhibiting mussel protein Antihypertensive Peptides.
The present invention for solving the problems of the technologies described above taked technical scheme is: the fast preparation method of mussel protein Antihypertensive Peptides, and it comprises the following steps:
1) preparation of Agarose Magnetic Microsphere and activation:according to weightmeasurement ratio 1 ~ 1.5g: 30 mL, agarose is added to the water, jointly boils and dissolve completely to agarose, add 1 ml Fe
3o
4magnetic fluid, vortex mixer fully mixes; Under agitation mixed solution is added dropwise in the organic phase (Span-80: whiteruss=1g:25mL) of 80 DEG C, and reacts 15 ~ 20 min at 80 DEG C; In 250 rpm rotating speed mechanical stirring 10 ~ 15 min, microballoon is shaped after organic phase is cooled to 40 DEG C, and is separated in magnetic field, obtained microballoon uses sherwood oil and washed with de-ionized water 3 times respectively, to remove remaining organic phase, obtains Agarose Magnetic Microsphere; By NaBH
4join in NaOH solution (0.8 ~ 1.0 mol/L) according to weightmeasurement ratio 2 ~ 3mg: 1mL, then epoxy chloropropane is joined in NaOH solution (0.8 ~ 1.0 mol/L) according to volume ratio 0.5 ~ 0.7: 1 again, finally according to weightmeasurement ratio 2 ~ 3 g: 1 mL, Agarose Magnetic Microsphere is joined in NaOH solution (0.8 ~ 1.0 mol/L), at 40 DEG C, stir 3 ~ 5 h, obtain activated agarose magnetic microsphere.
) ACE fixing:according to mass ratio 1 ~ 1.5: 10, the Agarose Magnetic Microsphere of angiotensin-converting enzyme (ACE) and activation is added in borate buffer solution (0.1 mol/L), after 40 ~ 50 DEG C of vibration 2 ~ 3 h, magnetic field put into by mixed solution, Agarose Magnetic Microsphere is separated, and fully wash with distilled water, until washed out without zymoprotein, vacuum lyophilization obtains Agarose Magnetic Microsphere Immobilized ACE.
) enzymolysis of mussel protein and ultrafiltration:mussel is shelled, mussel meat mixes according to the weightmeasurement ratio of 1g:3 ~ 5mL with glycine-NaOH buffer, homogenate, regulate pH value to 9.5 ~ 10, obtain mixed solution; Mixed solution temperature regulating to 45 ~ 55 DEG C, add Sumizyme MP (2.0 × 10 according to 0.5 ~ 0.8% of mussel meat quality
5u/g), enzymolysis 4 ~ 6 h; Enzymolysis solution is warming up to 90 ~ 95 DEG C, and after this temperature keeps 10 ~ 15min; Temperature regulating to 35 ~ 40 DEG C, adjust pH to 8.5 ~ 9.0 with 1 mol/LNaOH solution, add trypsin 1.9 × 10 according to 0.8 ~ 1.0% of mussel meat quality
4u/g), after enzymolysis 4 ~ 6 h, adopted by enzymolysis solution 1 kDa ultra-filtration membrane to carry out uf processing, collect molecular weight and be less than 1 kDa part, freeze-drying, be ultrafiltration zymolyte.
) preparation of mussel protein Antihypertensive Peptides:by ultrafiltration zymolyte successively through the absorption of Agarose Magnetic Microsphere Immobilized ACE and RPLC (RP-HPLC) purifying, obtain Antihypertensive Peptides.
As preferably, the mussel in described step 3) be Mytilus crassitesta Lischke (
mytilus coruscus).
As improvement, the Agarose Magnetic Microsphere Immobilized ACE absorption in described step 4) and RP-HPLC purifying are:
The absorption of Agarose Magnetic Microsphere Immobilized ACE: to borate buffer solution (0.1 mol/L, pH 7.8) to add NaCl to concentration be 0.2 mol/L, then adding ultrafiltration zymolyte to concentration is 5 ~ 8 mg/mL, finally add Agarose Magnetic Microsphere Immobilized ACE according to 30 ~ 50 times of zymolyte weight in solution, after adsorbing 45 min, utilize magnetic field by magnetic microsphere and solution separating, with borate buffer solution repetitive scrubbing microballoon to washings 220 nm and 280 nm without after uv-absorbing, by magnetic microsphere desorption in the NaCl solution of 1.0 mol/L, utilize magnetic field by magnetic microsphere and solution separating, solution freeze-drying, obtain Antihypertensive Peptides mixture.
RP-HPLC purifying: Antihypertensive Peptides mixture is made into 45 ~ 55 μ g/mL solution, utilizes RP-HPLC to carry out purifying, according to the inhibit activities to ACE Antihypertensive Peptides Val-Ser-Trp-Pro-Cys-Arg-Trp(VSWPCRW).
Preferably, described RP-HPLC condition is: sample size is 19 ~ 21 μ L; Chromatographic column is Zorbax C18(250 × 4.6mm, 5 μm); Moving phase is 40% acetonitrile; Elution speed is 1.0 mL/min; Ultraviolet detection wavelength is 220 nm.
Enzymolysis mussel protein of the present invention prepares the method for Antihypertensive Peptides, and tool has the following advantages:
What the present invention adopted is a kind of biological enzyme, easily by the monitoring to enzymolysis process, ACEP is farthest discharged, and improves the utilization ratio of raw material.Prepared ACEP is that mussel meat obtains through enzymic hydrolysis, and safely, have no side effect, ACE inhibitory activity is remarkable, has hypotensive effect to hyperpietic.
Product of the present invention can as medicine and protective foods etc., and craft science is reasonable, simple to operate, has stronger industrial implementation.Than existing preparation method, enzymolysis, ultrafiltration, the absorption of magnetic microsphere immobilized enzyme and RP-HPLC multiple means have been merged in the present invention simultaneously, and method is more perfect, and the Antihypertensive Peptides obtained has higher activity.
Accompanying drawing explanation
Fig. 1 is the color atlas that embodiment of the present invention Zorbax C18 post obtains when carrying out chromatography.
Embodiment
Below in conjunction with accompanying drawing embodiment, the present invention is described in further detail.
Embodiment:
A fast preparation method for mussel protein Antihypertensive Peptides, preparation flow is as follows: absorption " RP-HPLC purifying " Antihypertensive Peptides of mussel meat " historrhexis " enzymolysis " ultrafiltration " Agarose Magnetic Microsphere Immobilized ACE.
) preparation of Agarose Magnetic Microsphere and activation:according to weightmeasurement ratio 1.5g: 30 mL, agarose is added to the water, jointly boils and dissolve completely to agarose, add 1 ml Fe
3o
4magnetic fluid, vortex mixer fully mixes; Under agitation mixed solution is added dropwise in the organic phase (Span-80: whiteruss=1g:25mL) of 80 DEG C, and reacts 20 min at 80 DEG C; Organic phase is cooled to 40 DEG C makes microballoon be shaped in 250 rpm rotating speed mechanical stirring 15 min, and is separated in magnetic field, and obtained microballoon uses sherwood oil and washed with de-ionized water 3 times respectively, to remove remaining organic phase, obtains Agarose Magnetic Microsphere; By NaBH
4join in NaOH solution (0.8 mol/L) according to weightmeasurement ratio 2mg: 1mL, then epoxy chloropropane is joined in NaOH solution (0.8 mol/L) according to volume ratio 0.5: 1 again, finally according to weightmeasurement ratio 3 g: 1 mL, Agarose Magnetic Microsphere is joined in NaOH solution (0.8 mol/L), at 40 DEG C, stir 3 h, obtain activated agarose magnetic microsphere.
) ACE fixing:according to mass ratio 1.5: 10, the Agarose Magnetic Microsphere of angiotensin-converting enzyme (ACE) and activation is added in borate buffer solution (0.1 mol/L), after 50 DEG C of vibration 3 h, magnetic field put into by mixed solution, be separated Agarose Magnetic Microsphere, and fully wash with distilled water, until washed out without zymoprotein, vacuum lyophilization obtains Agarose Magnetic Microsphere Immobilized ACE.
) enzymolysis of mussel protein and ultrafiltration:by Mytilus crassitesta Lischke (
mytilus coruscus) shell, mussel meat mixes according to the weightmeasurement ratio of 1g:4 mL with glycine-NaOH buffer, homogenate, regulates pH value to 9. 5, obtains mixed solution; Mixed solution temperature regulating to 50 DEG C, then adds Sumizyme MP (2.0 × 10 according to 0.8% of mussel meat quality
5u/g), enzymolysis 5 h; Enzymolysis solution is warming up to 95 DEG C, and after this temperature keeps 10 min; Temperature regulating to 37 DEG C, adjusts pH to 8.6 by 1 mol/L NaOH solution, adds trypsin 1.9 × 10 according to 1.0% of mussel meat quality
4u/g), after enzymolysis 6 h, adopted by enzymolysis solution 1 kDa ultra-filtration membrane to carry out uf processing, collect molecular weight and be less than 1 kDa part, freeze-drying, be ultrafiltration zymolyte.
) preparation of mussel protein Antihypertensive Peptides:by ultrafiltration zymolyte successively through the absorption of Agarose Magnetic Microsphere Immobilized ACE and RPLC system (RP-HPLC) purifying, obtain Antihypertensive Peptides.
1. the absorption of Agarose Magnetic Microsphere Immobilized ACE: to borate buffer solution (0.1 mol/L, pH 7.8) to add NaCl to concentration be 0.2 mol/L, then adding ultrafiltration zymolyte to concentration is 6 mg/mL, finally add Agarose Magnetic Microsphere Immobilized ACE according to 40 times of zymolyte weight in solution, after adsorbing 45 min, utilize magnetic field by magnetic microsphere and solution separating, with borate buffer solution repetitive scrubbing microballoon to washings 220 nm and 280 nm without after uv-absorbing, then by magnetic microsphere desorption in the NaCl solution of 1.0 mol/L, utilize magnetic field by magnetic microsphere and solution separating, solution freeze-drying, obtain Antihypertensive Peptides mixture.
2. RP-HPLC purifying: Antihypertensive Peptides mixture is made into 45 μ g/mL solution, utilizes RP-HPLC(condition: sample size is 20 μ L; Chromatographic column is Zorbax C18(250 × 4.6mm, 5 μm); Moving phase is 40% acetonitrile; Elution speed is 1.0 mL/min; Ultraviolet detection wavelength is 220 nm) carry out purifying, according to the inhibit activities of ACE being obtained to a high reactivity Antihypertensive Peptides (see figure 1).
3. structure detection: collecting the highest active Antihypertensive Peptides is simple spike after testing, utilizing protein/polypeptide sequenator to measure aminoacid sequence is Val-Ser-Trp-Pro-Cys-Arg-Trp(VSWPCRW), ESI/MS detection molecules amount is 935.07 Da.
By above-mentioned obtained mussel protein Antihypertensive Peptides Val-Ser-Trp-Pro-Cys-Arg-Trp(VSWPCRW) carry out ACE inhibitory activity experiment.Experimental result shows: the half inhibiting rate (IC of this polypeptide
50) be 37.53 ± 1.09 μMs.
Finally, it is also to be noted that what enumerate above is only a specific embodiment of the present invention.Obviously, the invention is not restricted to above embodiment, many distortion can also be had.All distortion that those of ordinary skill in the art can directly derive from content disclosed by the invention or associate, all should think protection scope of the present invention.
SEQUENCE LISTING
<110> Oceanography Institute Of Zhejiang
The fast preparation method of <120> mussel protein Antihypertensive Peptides
<130> zjou-wb-201504-4
<160> 1
<170> PatentIn version 3.5
<210> 1
<211> 7
<212> PRT
<213> synthetic
<400> 1
Val Ser Trp Pro Cys Arg Trp
1 5
Claims (6)
1. the fast preparation method of mussel protein Antihypertensive Peptides, is characterized in that comprising the following steps:
1) preparation of Agarose Magnetic Microsphere and activation:according to weightmeasurement ratio 1 ~ 1.5g: 30 mL, agarose is added to the water, jointly boils and dissolve completely to agarose, add 1 ml Fe
3o
4magnetic fluid, vortex mixer fully mixes; Under agitation mixed solution is added dropwise in the organic phase of 80 DEG C, and reacts 15 ~ 20 min at 80 DEG C; Organic phase is cooled to 40 DEG C makes microballoon be shaped in 250 rpm rotating speed mechanical stirring 10 ~ 15 min, and is separated in magnetic field, and obtained microballoon uses sherwood oil and washed with de-ionized water 3 times respectively, to remove remaining organic phase, obtains Agarose Magnetic Microsphere; By NaBH
4join in the NaOH solution of 0.8 ~ 1.0 mol/L according to weightmeasurement ratio 2 ~ 3mg: 1mL, then epoxy chloropropane is joined according to volume ratio 0.5 ~ 0.7: 1 in the NaOH solution of 0.8 ~ 1.0 mol/L again, finally according to weightmeasurement ratio 2 ~ 3 g: 1 mL, Agarose Magnetic Microsphere is joined in the NaOH solution of 0.8 ~ 1.0 mol/L, at 40 DEG C, stir 3 ~ 5 h, obtain activated agarose magnetic microsphere;
2) ACE's is fixing:according to mass ratio 1 ~ 1.5: 10, the Agarose Magnetic Microsphere of angiotensin-converting enzyme and activation is added in the borate buffer solution of 0.1 mol/L, after 40 ~ 50 DEG C of vibration 2 ~ 3 h, magnetic field put into by mixed solution, Agarose Magnetic Microsphere is separated, and fully wash with distilled water, until washed out without zymoprotein, vacuum lyophilization obtains Agarose Magnetic Microsphere Immobilized ACE;
3) enzymolysis of mussel protein and ultrafiltration:mussel is shelled, mussel meat mixes according to the weightmeasurement ratio of 1g:3mL ~ 1g:5mL with glycine-NaOH buffer, homogenate, regulate pH value to 9. 5 ~ 10, obtain mixed solution; By described mixed solution temperature regulating to 45 ~ 55 DEG C, add Sumizyme MP according to 0.5 ~ 0.8% of mussel meat quality, enzymolysis 4 ~ 6 h; Then enzymolysis solution is warming up to 90 ~ 95 DEG C, and keeps 10 ~ 15min; By enzymolysis solution temperature regulating to 35 ~ 40 DEG C, pH to 8.5 ~ 9.0 are adjusted by 0.1 mol/L NaOH solution, trypsinase is added according to 0.8 ~ 1.0% of mussel meat quality, after enzymolysis 4 ~ 6 h, 1 kDa ultra-filtration membrane is adopted by enzymolysis solution to carry out uf processing, collect molecular weight and be less than 1 kDa part, freeze-drying, be ultrafiltration zymolyte;
4) preparation of mussel protein Antihypertensive Peptides:by ultrafiltration zymolyte successively through the absorption of Agarose Magnetic Microsphere Immobilized ACE and RPLC purifying, obtain Antihypertensive Peptides.
2. preparation method according to claim 1, is characterized in that in described step 1), organic phase is Span-80: the solid-to-liquid ratio of whiteruss is 1g:25mL.
3. preparation method according to claim 1, the mussel that it is characterized in that in described step 3) be Mytilus crassitesta Lischke namely
mytilus coruscus.
4. preparation method according to claim 1, is characterized in that the Agarose Magnetic Microsphere Immobilized ACE absorption of described step 4) and the detailed process of RP-HPLC purifying are:
The absorption of Agarose Magnetic Microsphere Immobilized ACE: it is 0.2 mol/L that the borate buffer solution to concentration 0.1 mol/L, pH 7.8 adds NaCl to concentration, then adding ultrafiltration zymolyte to concentration is 5 ~ 8 mg/mL, finally add Agarose Magnetic Microsphere Immobilized ACE according to 30 ~ 50 times of zymolyte weight in solution, after adsorbing 45 min, utilize magnetic field by magnetic microsphere and solution separating, with borate buffer solution repetitive scrubbing magnetic microsphere to washings 220 nm and 280 nm without uv-absorbing; Finally by magnetic microsphere desorption in the NaCl solution of 1.0 mol/L, utilize magnetic field by magnetic microsphere and solution separating, solution freeze-drying, obtain Antihypertensive Peptides mixture;
RPLC purifying: Antihypertensive Peptides mixture is made into 45 ~ 55 μ g/mL solution, utilizes RPLC to carry out purifying, according to the inhibit activities to ACE Antihypertensive Peptides Val-Ser-Trp-Pro-Cys-Arg-Trp.
5. preparation method according to claim 1, is characterized in that the condition of described RPLC is: sample size 19 ~ 21 μ L; Chromatographic column is specification is 250 mm × 4.6mm, the Zorbax C18 of 5 μm; Moving phase is 40% acetonitrile; Elution speed 1.0 mL/min; Ultraviolet detection wavelength 220 nm.
6. preparation method according to claim 1, is characterized in that the half inhibiting rate of prepared Antihypertensive Peptides Val-Ser-Trp-Pro-Cys-Arg-Trp to ACE is 37.53 ± 1.09 μMs.
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106834399A (en) * | 2016-12-30 | 2017-06-13 | 浙江海洋大学 | A kind of Antihypertensive Peptides from Trachyostracous mussel closed shell flesh |
| CN107365818A (en) * | 2017-07-07 | 2017-11-21 | 浙江海润达科技有限公司 | A kind of preparation method of mussel protein small peptide and its preparation method of respective combination chewable tablets |
| CN107383168A (en) * | 2017-09-11 | 2017-11-24 | 浙江海洋大学 | A kind of Trachyostracous mussel Antihypertensive Peptides |
| CN107955068A (en) * | 2017-09-29 | 2018-04-24 | 浙江海洋大学 | A kind of Trachyostracous mussel closed shell creatase demodulates fat pentapeptide |
| CN109485700A (en) * | 2018-12-05 | 2019-03-19 | 广西大学 | A kind of angiotensin converting enzyme ace inhibitory peptide and preparation method thereof |
| CN112940079A (en) * | 2021-03-19 | 2021-06-11 | 广州明创生物科技有限公司 | Rice antihypertensive peptide and enzymolysis preparation method thereof |
| CN113617060A (en) * | 2021-08-09 | 2021-11-09 | 福建省水产研究所（福建水产病害防治中心） | Immobilized enzyme gel affinity adsorption column preparation method and method for extracting active peptide from puffer fish |
| CN114044807A (en) * | 2021-11-19 | 2022-02-15 | 浙江海洋大学 | Mussel blood fat reducing oligopeptide for treating hyperlipidemia |
| CN117169393A (en) * | 2023-11-03 | 2023-12-05 | 杭州湃肽生化科技有限公司 | Method for detecting cyclic peptide in plant tissue |
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Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106834399A (en) * | 2016-12-30 | 2017-06-13 | 浙江海洋大学 | A kind of Antihypertensive Peptides from Trachyostracous mussel closed shell flesh |
| CN107365818A (en) * | 2017-07-07 | 2017-11-21 | 浙江海润达科技有限公司 | A kind of preparation method of mussel protein small peptide and its preparation method of respective combination chewable tablets |
| CN107383168A (en) * | 2017-09-11 | 2017-11-24 | 浙江海洋大学 | A kind of Trachyostracous mussel Antihypertensive Peptides |
| CN107955068A (en) * | 2017-09-29 | 2018-04-24 | 浙江海洋大学 | A kind of Trachyostracous mussel closed shell creatase demodulates fat pentapeptide |
| CN109485700B (en) * | 2018-12-05 | 2021-08-17 | 广西大学 | Angiotensin converting enzyme ACE inhibitory peptide and preparation method thereof |
| CN109485700A (en) * | 2018-12-05 | 2019-03-19 | 广西大学 | A kind of angiotensin converting enzyme ace inhibitory peptide and preparation method thereof |
| CN112940079A (en) * | 2021-03-19 | 2021-06-11 | 广州明创生物科技有限公司 | Rice antihypertensive peptide and enzymolysis preparation method thereof |
| CN112940079B (en) * | 2021-03-19 | 2022-09-09 | 广州明创生物科技有限公司 | Rice antihypertensive peptide and enzymolysis preparation method thereof |
| CN113617060A (en) * | 2021-08-09 | 2021-11-09 | 福建省水产研究所（福建水产病害防治中心） | Immobilized enzyme gel affinity adsorption column preparation method and method for extracting active peptide from puffer fish |
| CN113617060B (en) * | 2021-08-09 | 2023-02-10 | 福建省水产研究所（福建水产病害防治中心） | Immobilized enzyme gel affinity adsorption column preparation method and method for extracting active peptide from puffer fish |
| CN114044807A (en) * | 2021-11-19 | 2022-02-15 | 浙江海洋大学 | Mussel blood fat reducing oligopeptide for treating hyperlipidemia |
| CN114044807B (en) * | 2021-11-19 | 2023-08-22 | 浙江海洋大学 | Mussel hypolipidemic oligopeptide for treating hyperlipidemia |
| CN117169393A (en) * | 2023-11-03 | 2023-12-05 | 杭州湃肽生化科技有限公司 | Method for detecting cyclic peptide in plant tissue |
| CN117169393B (en) * | 2023-11-03 | 2024-03-19 | 杭州湃肽生化科技有限公司 | Method for detecting cyclic peptide in plant tissue |
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