CN108948143A - Tripeptides and its application with ACE inhibitory activity - Google Patents

Tripeptides and its application with ACE inhibitory activity Download PDF

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Publication number
CN108948143A
CN108948143A CN201810881779.0A CN201810881779A CN108948143A CN 108948143 A CN108948143 A CN 108948143A CN 201810881779 A CN201810881779 A CN 201810881779A CN 108948143 A CN108948143 A CN 108948143A
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tripeptides
ace
ace inhibitory
activity
inhibitory activity
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CN108948143B (en
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于志鹏
武思佳
赵文竹
邱卓楠
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Bohai University
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    • 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
    • C07K5/08—Tripeptides
    • C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
    • 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
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/17—Amino acids, peptides or proteins
    • A23L33/18—Peptides; Protein hydrolysates
    • 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
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • 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
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/0808—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
    • 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
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0812—Tripeptides with the first amino acid being neutral and aromatic or cycloaliphatic
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Abstract

The invention discloses with ACE inhibitory activity tripeptides and its application.ACE inhibitory tripeptides, amino acid sequence are respectively HGR, WAK, CMK, AMR, LEW and FPK, and molecular weight is respectively 368.40,403.49,380.52,376.48,446.51,390.49 Da.Ace inhibitory peptide provided by the present invention has significant inhibitory effect to ACE, and there is safe without toxic side effect, it is easy to the features such as absorbing, can be used as functional component for being with a wide range of applications and highly important meaning in food, health care product and decompression drug.

Description

Tripeptides and its application with ACE inhibitory activity
Technical field
The invention belongs to field of biotechnology, and in particular to tripeptides and its application with ACE inhibitory activity.
Background technique
Angiotensin-Converting (ACE) is the key enzyme for adjusting blood pressure, in renin-angiotensin-aldosterone system It plays a key effect in kallikrein kinin system.It can be by angiotensin I (the ANG I of inactive form；Asp- Arg-Val-Tyr-Ile-His-Pro-Phe-His-Leu it) is converted into the active Angiotensin II (ANG of vasoconstriction II；Asp-Arg-Val-Tyr-Ile-His-Pro-Phe) and lead to the degradation of bradykinin.Currently, clinically having used card Top's benefit, enalapril and lisinopril etc. synthesize the Vel-Tyr-Pro-Trp-Thr-Gln-Arg-Phe of class to treat hypertension.But synthesize the Vel-Tyr-Pro-Trp-Thr-Gln-Arg-Phe of class It can cause potential health hazard.Therefore, natural Vel-Tyr-Pro-Trp-Thr-Gln-Arg-Phe receives more and more attention recently.
Biologically active peptide is that cracking comes out and have the segment of physiological activity from protein sequence, is mainly derived from dynamic Vegetable protein hydrolysis or microbial fermentation, while the convenience of chemical synthesis and chemical modification is had both, attract more and more Food Science, biology, chemistry and its research interest of crossing domain researcher, have been widely used in food and medicine row Industry.Angiotensin converting enzyme (angiotensin converting-Ienzyme, ACE) peptide for inhibiting is a kind of important function Active peptide is one of the emphasis of biologically active peptide research field, can inhibit internal ACE activity and plays significant blood pressure lowering and make With.Food-borne biologically active peptide is usually safer and more selective.The separation preparation tool ace inhibitory peptide from food-borne protein As research hotspot.As people study the raising of the marine resources level of understanding and modern biotechnology in marine drug In application.Currently, ace inhibitory peptide is found in a variety of foods such as egg, casein, wheat.Marine protein matter Amino acid composition or sequence be very different with terrestrial life albumen.Functional protein and active material have been asked for ocean An important content as coastal state's ocean development.In the recent period, many to study the ACE inhibition for also highlighting fish protein hydrolyzate Activity.
It is mostly to be obtained from mixed-matrix by conventional bio-chemistry separation means at present for the research of ace inhibitory peptide The active active peptide of ACE can obviously be inhibited.But it separates and purifies from protein hydrolysate and obtain high-purity and high activity Biologically active peptide is complicated and difficult.In recent years, continuous with the rapid development of molecular biology and peptide omics technology It is perfect, retrieved with the database in peptide group, the research method screened using Target discovery and primer gradually at For the important trend of active peptide research.
Summary of the invention
The object of the present invention is to provide preparations simply and with ACE inhibitory tripeptides, and can be by the ace inhibitory peptide application In food, health care product and field of biological pharmacy.
Tripeptides with ACE inhibitory activity of the invention, amino acid sequence are respectively His-Gly-Arg, Trp-Ala- Lys, Cys-Met-Lys, Ala-Met-Arg, Leu-Glu-Trp and Phe-Pro-Lys, with single-letter be expressed as HGR, WAK, CMK, AMR, LEW and FPK, ESI-MS measure molecular weight 368.40,403.49,380.52,376.48,446.51,390.49Da.
Ace inhibitory peptide of the invention has good ACE inhibitory effect, IC50Value for be respectively 106,400.35, 190.78、697.25、193.36、426.83μM。
The purpose of the present invention is achieved through the following technical solutions:
(1) the virtual enzymatic hydrolysis and virtual screening of protein sequence
The present invention is by ExPASy PeptideCutter (http://web.expasy.org/peptide_cutter/) This online virtual digestion tool carries out virtual digestion, the tripeptide sequence and BIOPEP that will be generated after digestion to Fish protein sequence (http://www.uwm.edu.pl/biochemia/index.php/en/biopep) and AHTPDB (http: // Crdd.osdd.net) known ace inhibitory peptide is compared in database, and screening acquires the tripeptides without report.By The Line tool ToxinPred, peptide property calculator, PeptideRanker and admetSAR are to without report Tripeptide sequence carry out toxicity, water solubility, bioactivity and ADME (absorb, distribution, metabolism, excretion) prediction of property.Screening Obtain Activity Score higher than 0.5, nontoxic, dissolubility is good and has the tripeptides of good small intestine permeability.
(2) targeting screening
From the crystal knot for obtaining the people ACE compound with that sharp Puli in PDB database (http://www.rcsb.org/) Structure (1086), and as protein target, pass through the CDOCKER journey of 2017 client software of Discovery Studio (DS) Sequence carries out molecular docking to screen the tripeptides that can be combined closely with ACE.It is obtained in conjunction with ' CDOCKER-INTERACTION-ENERGY ' Divide, form the number of hydrogen bond and the key amino acid of effect, the tripeptides with potential ACE inhibitory activity on screening theory.
(3) external ACE inhibitory activity measurement
It is verified by activity of the high performance liquid chromatography to these tripeptides.Take hippuroyl-histamine acyl-leucine (HHL) substrate solution, is added HGR solution and is uniformly mixed, 3~5min is preheated in 37 DEG C of waters bath with thermostatic control, and ACE liquid is then added and fills Divide and mix, after 37 DEG C of heat preservation 30min, the 1mol/L HCl added terminates reaction, obtains reaction solution.Borate buffer is used simultaneously Inhibitor solution is substituted as blank control group.The reaction solution is directly analyzed with HPLC system.
Chromatographic condition: 25 DEG C of column temperature, flow velocity 0.5mL/min, mobile phase acetonitrile/water is 25: 75 isocratic elutions, Detection wavelength 228nm。
Compared with prior art, the present invention having the advantages that are as follows:
1. this screening from Fish protein for the first time obtained effectively inhibiting the active tripeptides HGR, WAK of ACE, CMK, AMR, LEW and FPK, and specify the structure of tripeptides HGR, WAK, CMK, AMR, LEW and FPK；Simultaneously HGR, WAK, CMK, AMR, LEW and FPK has many advantages, such as safe without toxic side effect, can overcome pipe intestinal digesting and be easy to absorb, thus as function at Divide in food, health care product and decompression drug, to there is good potentiality and application prospect.
Detailed description of the invention
6 width of attached drawing of the present invention, in which:
Fig. 1 HGR schemes with the 3D for docking result of ACE；
Fig. 2 WAK schemes with the 3D for docking result of ACE；
Fig. 3 CMK schemes with the 3D for docking result of ACE；
Fig. 4 AMR schemes with the 3D for docking result of ACE；
Fig. 5 LEW schemes with the 3D for docking result of ACE；
Fig. 6 FPK schemes with the 3D for docking result of ACE；
Specific embodiment
The invention will be further elaborated in a manner of specific embodiment below.
The virtual screening of 1 Larimichthys crocea nebulin ace inhibitory peptide of embodiment and activity verifying
Based in sequence of threads ExPASy PeptideCutter, three kinds of typical pipe intestinal digesting protease, that is, stomach eggs are used White enzyme (EC 3.4.23.1), trypsase (EC 3.4.21.4) and chymotrypsin (EC 3.4.21.1) are to Larimichthys crocea companion Actin (Accession of NCBI:KKF11904.1) carries out simulation enzymatic hydrolysis.By online tool ToxinPred, Peptide property calculator, PeptideRanker and admetSAR carry out poison to the tripeptide sequence without report The prediction of property, water solubility, bioactivity and ADME property.Screening obtain nontoxic, dissolubility is good, Activity Score be higher than 0.5 and have There is the tripeptides of good small intestine permeability, and is that protein target is carried out further by molecular docking with ACE (PDB ID:1O86) Screening.The key amino acid for scoring and acting in conjunction with CDOCKER, screening have obtained theoretically having potential ACE inhibitory activity Tripeptides HGR.The result shows that HGR can be with key residues, that is, His353, Glu384, Ala354, His513, Tyr523 of ACE (Fig. 1) is combined with Lys511.Tripeptides HER is synthesized, ESI-MS measure molecular weight be 368.40Da ([M+H]+ 369.00Da.Its activity is verified by high performance liquid chromatography.The result shows that the activity of ACE can be effectively suppressed in HGR, IC50Value is 106 μM.
The virtual screening of 2 Larimichthys crocea moesin ace inhibitory peptide of embodiment and activity verifying
Based on ExPASy PeptideCutter, this online virtual digestion tool, uses pepsin (EC 3.4.23.1) and trypsase (EC 3.4.21.4) is to Larimichthys crocea moesin (Accession of NCBI:KKF16686) Carry out virtual digestion, and by online tool ToxinPred, peptide property calculator, PeptideRanker and admetSAR carries out toxicity, water solubility, bioactivity and ADME property to the tripeptide sequence without report Prediction.Screening obtain nontoxic, dissolubility is good, Activity Score be higher than 0.5 and with good small intestine permeability tripeptides, and with ACE (PDB ID:1O86) is that protein target is further screened by molecular docking.It scores and acts in conjunction with CDOCKER Key amino acid, screening obtained theoretically with potential ACE inhibitory activity tripeptides WAK and CMK.The result shows that WAK can With with ACE residue, that is, His353, Ala354, His513, Lys511, Tyr520, Thr282, Glu384, Glu376, Asp453, Glu411 and Lys511 combine (Fig. 2), CMK can with residue, that is, His513, Lys511 of ACE, Tyr520, His353, Glu384, Ala354, Glu376 and Asp453 combine (Fig. 3).Tripeptides WAK and CMK are synthesized, ESI-MS is surveyed Determining molecular weight is respectively 403.49Da ([M+H]+404.00Da) and 380.52Da ([M+H]+380.00Da).Pass through efficient liquid phase Chromatography verifies its activity.The result shows that the activity of ACE, IC can be effectively suppressed in tripeptides WAK and CMK50Value is respectively 400.35 with 190.78 μM.
The virtual screening of 3 rheum officinale Isin glue collagen ace inhibitory peptide of embodiment and activity verifying
Based on ExPASy PeptideCutter virtual digestion tool online, three kinds of typical pipe intestinal digesting albumen are used Enzyme, that is, pepsin (EC 3.4.23.1), trypsase (EC 3.4.21.4) and chymotrypsin (EC 3.4.21.1) are right Rheum officinale Isin glue collagen (Accession of NCBI:KKF14511) carries out virtual digestion, and passes through online tool ToxinPred, peptide property calculator, PeptideRanker and admetSAR are to the tripeptides without report The prediction of sequence progress toxicity, water solubility, bioactivity and ADME property.Screening obtains that nontoxic, dissolubility is good, Activity Score is high In 0.5 and with good small intestine permeability tripeptides, and with ACE (PDB ID:1O86) be protein target pass through molecular docking Further screened.The key amino acid for scoring and acting in conjunction with CDOCKER, screening have obtained theoretically having potential The tripeptides AMR and LEW of ACE inhibitory activity.The result shows that AMR can with residue, that is, Tyr523, His513 of ACE, Glu411, His353, Glu384, Ala354, His387, Ala356, Glu162, Val379 and Val380 combine (Fig. 4), and LEW can be with The residue of ACE, that is, Tyr520, Val518, Lys511, His353, Ala354, Val380, Ser355 and Ala356 combines (Fig. 5). Tripeptides AMR and LEW are synthesized, ESI-MS measurement molecular weight be respectively 376.48Da ([M+H]+376.95Da) and 446.51Da([M+H]+447.05Da).Its activity is verified by high performance liquid chromatography.The result shows that tripeptides AMR and The activity of ACE, IC can be effectively suppressed in LEW50Value is respectively 697.25 and 193.36 μM.
The virtual screening of 4 carp myosin ace inhibitory peptide of embodiment and activity verifying
Based on ExPASy PeptideCutter, this online virtual digestion tool, uses trypsase (EC 3.4.21.4) and chymotrypsin (EC 3.4.21.1) to carp myosin (Accession of NCBI: BAE16584) carry out virtual digestion, and by online tool ToxinPred, peptide property calculator, PeptideRanker and admetSAR carries out toxicity, water solubility, bioactivity and ADME property to the tripeptide sequence without report Prediction.Screening obtain nontoxic, dissolubility is good, Activity Score be higher than 0.5 and with good small intestine permeability tripeptides, and with ACE (PDB ID:1O86) is that protein target is further screened by molecular docking.It scores and acts in conjunction with CDOCKER Key amino acid, screening obtained theoretically with potential ACE inhibitory activity tripeptides FPK.The result shows that FPK can be with Residue, that is, Tyr520, His513, Lys511, His353, Glu384, Ala354, His383, Glu376, Thr282 of ACE and Asp453 combines (Fig. 6).Tripeptides FPK is synthesized, it is 390.49Da ([M+H]+391.4Da) that ESI-MS, which measures molecular weight,. Its activity is verified by high performance liquid chromatography.The result shows that the activity of ACE, IC can be effectively suppressed in tripeptides FPK50Value It is 426.83 μM.
Technical solution of the present invention is described in detail in embodiment described above, it should be understood that the above is only For specific embodiments of the present invention, it is not intended to restrict the invention, it should be pointed out that: for those skilled in the art For, it under the premise without departing from the spirit and scope of the present invention, can also make a variety of changes and modification, these variations and become Type also should be regarded as protection scope of the present invention.

Claims (3)

1. with ACE inhibitory activity tripeptides, which is characterized in that the tripeptide amino acid sequence be respectively HGR, WAK, CMK, AMR, LEW and FPK, ESI-MS measurement molecular weight is respectively 368.40,403.49,380.52,376.48,446.51, 390.49Da, IC50Value is respectively 106,400.35,190.78,697.25,193.36,426.83 μM.
2. the tripeptides according to claim 1 with ACE inhibitory activity, including using the ACE inhibitory tripeptides sequence as core The heart, any corresponding adjustment or modification that it is carried out.
3. a kind of active food of inhibition ACE, which is characterized in that containing the tripeptides with ACE inhibitory activity, described has The tripeptides of ACE inhibitory activity, amino acid sequence HGR, WAK, CMK, AMR, LEW and FPK.
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