CN114409730A - Active peptide, active peptide composition and application of active peptide composition in preparation of product with anti-aging effect - Google Patents
Active peptide, active peptide composition and application of active peptide composition in preparation of product with anti-aging effect Download PDFInfo
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Images
Classifications
-
- 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/08—Peptides having 5 to 11 amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- 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 relates to the technical field of biological medicines, and particularly discloses an active peptide, an active peptide composition and application thereof in preparation of a product with an anti-aging effect. The active peptide composition comprises any two or three of active peptides with structures shown in formula I, formula II and formula III. The active peptide or the composition thereof can relieve oxidative aging caused by environmental pollutants (benzopyrene), has excellent activity of delaying aging, and can reduce the generation of lipofuscin. The active peptide or the composition thereof has wide application prospect in preparing cosmetics, foods, dietary supplements or medicines with the activity of delaying senility.
Description
Technical Field
The invention relates to the technical field of biological medicines, in particular to an active peptide, an active peptide composition and application thereof in preparing a product with an anti-aging effect.
Background
Polycyclic aromatic hydrocarbons are one of the major environmental pollutants produced by forest fires, volcanic eruptions, fossil fuel combustion, and industry. Benzopyrene (BaP) is a polycyclic aromatic hydrocarbon, and cigarette smoke and automobile exhaust contain benzopyrene, and the lipophilicity of benzopyrene enables benzopyrene to easily permeate biological membranes and be absorbed through different metabolic pathways. Numerous studies have found that exposure to BaP induces oxidative stress, inflammatory injury, pulmonary toxicity, and the like in bronchial epithelial cells. Oxidative stress is caused by a disruption in the balance between the oxidative and antioxidant systems that can enhance oxidative stress by producing oxygen metabolites, including superoxide anion radicals, hydroxyl radicals and hydrogen peroxide, lipid peroxides and nitrogen oxides. BaP is metabolized to B [ alpha ] P-7, 8-diol-9, 10-epoxide (BPDE) or o-quinone, and forms a large amount of Reactive Oxygen Species (ROS). Reactive oxygen species (e.g., hydroxyl radicals, superoxide anions, and hydrogen peroxide) can react with various biological macromolecules (e.g., DNA, proteins, and lipids) to cause cellular damage and thus accelerate cellular senescence. However, there is currently no therapeutic product for aging caused by benzopyrene, an environmental pollutant.
Disclosure of Invention
In order to overcome at least one of the technical problems of the prior art, the present invention firstly provides an active peptide.
The detailed technical scheme of the invention is as follows:
the invention firstly provides an active peptide, which has a structure shown in a formula I, a formula II or a formula III:
the inventor surprisingly found in the research that: the active peptides with the structures shown in the formula I, the formula II and the formula III have excellent effect of delaying senility; especially has excellent effect of delaying environmental pollutants and aging caused by pyrene.
Wherein the amino acid sequence of the active peptide with the structure shown in the formula I is Leu-Trp-Glu-His-Ser-His, which is abbreviated as BLO-1 below; the amino acid sequence of the active peptide with the structure shown in the formula II is Tyr-Ser-Leu-His-Leu-His-Gly, which is abbreviated as BLO-2 in the following; the amino acid sequence of the active peptide with the structure shown in the formula III is Lys-Tyr-Gly-His-Glu-His-Ser, and is abbreviated as BLO-3 in the following.
The invention also provides an active peptide composition which comprises any two or three of the active peptides with the structures shown in the formulas I, II and III.
Preferably, the active peptide composition comprises active peptides with the structures shown in formula I, formula II and formula III;
wherein the molar ratio of the active peptides with the structures shown in the formula I, the formula II and the formula III is 1-10: 1-10.
Furthermore, the research of the inventor shows that the anti-aging effect of the active peptide with the structure shown in the formula I, the formula II and the formula III, especially the anti-aging effect caused by benzopyrene serving as an environmental pollutant, is better than that of the active peptide with the structure shown in any one of the formula I, the formula II or the formula III.
More preferably, the molar ratio of the active peptides with the structures shown in the formula I, the formula II and the formula III is 1-5: 1-5.
Preferably, the molar ratio of the active peptides having the structures shown in formula I, formula II and formula III is 1:1: 1.
The invention also provides application of the active peptide or the active peptide composition in preparing cosmetics, foods, dietary supplements or medicines.
Preferably, the cosmetic, food, dietary supplement or medicine is a cosmetic, food, dietary supplement or medicine with the effect of delaying aging.
Further preferably, the aging is aging caused by environmental pollutants.
Most preferably, the aging is caused by benzopyrene, an environmental pollutant.
The active peptide and the active peptide composition have excellent aging delaying effect, particularly have excellent aging delaying effect caused by environmental pollutant benzopyrene; therefore, the compound can be used as an active ingredient for preparing food, dietary supplements or medicaments with the effect of delaying senescence, particularly the effect of delaying senescence caused by environmental pollutants benzopyrene.
Preferably, the cosmetic, food, dietary supplement or pharmaceutical product is a cosmetic, food, dietary supplement or pharmaceutical product having a lipofuscin production inhibiting effect.
Further, the present investigators have also found that the active peptides and active peptide compositions also inhibit lipofuscin production; therefore, the active peptide or active peptide composition of the present invention can be used for preparing cosmetics, foods, dietary supplements or medicines having the effect of inhibiting the production of lipofuscin.
Has the advantages that: (1) the active peptide or the composition thereof provided by the invention has excellent anti-aging activity and has wide application prospect in cosmetics, foods, dietary supplements or medicines. (2) The active peptide with the anti-aging activity is an active molecular compound, has simple preparation process and convenient operation, and is beneficial to the application of the active peptide in cosmetics, foods, dietary supplements or medicines.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only drawings of some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to these drawings without creative efforts.
FIG. 1 is a mass spectrum of BLO-1.
FIG. 2 is a graph showing the results of high performance liquid chromatography measurement of BLO-1.
FIG. 3 is a mass spectrum of BLO-2.
FIG. 4 is a graph showing the results of high performance liquid chromatography measurement of BLO-2.
FIG. 5 is a mass spectrum of BLO-3.
FIG. 6 is a graph showing the results of high performance liquid chromatography measurement of BLO-3.
FIG. 7 is a graph showing experimental results of the effects of BLO-1, BLO-2, BLO-3 and combinations thereof on the reduction of the motility of C.elegans induced by BaP exposure.
FIG. 8 is a graph showing the experimental results of the effect of Bifidobacterium longum oligopeptide or its composition on the MDA, SOD activity and ROS content of C.elegans induced by BaP exposure.
Detailed Description
The technical solution of the present invention will be clearly and completely described with reference to the following examples. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
EXAMPLE 1 preparation of active peptides
(1) 200mg of Fmoc-His Wang Resin is put in a solid phase synthesis tube, N-Dimethylformamide (DMF) is added, then the mixture is kept stand for 40 minutes to fully swell the Resin, the solvent is filtered out, piperidine DMF solution is added, and the solvent is filtered out after oscillation. Dissolving Fmoc-Ser-OH, 1-hydroxybenzotriazole and O-benzotriazol-tetramethylurea hexafluorophosphate in DMF, adding N, N-diisopropylethylamine, uniformly mixing, protecting from light, activating, adding into resin, stirring for 2 hours at 25 ℃ under the action of nitrogen blowing, carrying out suction filtration, washing with DMF and dichloromethane in sequence, and drying the solvent. And repeating the steps, sequentially adding activated Fmoc-His-OH, Fmoc-Glu-OH, Fmoc-Trp-OH and Fmoc-Leu-OH into the resin, blowing nitrogen at 25 ℃ and stirring, washing the resin after complete reaction, performing rotary evaporation on the obtained filtrate to obtain a precipitate, and performing freeze drying to obtain the BLO-1.
(2) Placing 200mg Fmoc-Gly Wang Resin in a solid phase synthesis tube, adding N, N-Dimethylformamide (DMF), standing for 40 min to fully swell the Resin, filtering to remove the solvent, adding piperidine DMF solution, oscillating, and filtering to remove the solvent. Dissolving Fmoc-His-OH, 1-hydroxybenzotriazole and O-benzotriazol-tetramethylurea hexafluorophosphate in DMF, adding N, N-diisopropylethylamine, uniformly mixing, protecting from light, activating, adding into resin, stirring for 2 hours at 25 ℃ under the action of nitrogen blowing, carrying out suction filtration, washing with DMF and dichloromethane in sequence, and drying the solvent. And repeating the steps, sequentially adding activated Fmoc-Leu-OH, Fmoc-His-OH, Fmoc-Leu-OH, Fmoc-Ser-OH and Fmoc-Tyr-OH into the resin, stirring by blowing nitrogen at 25 ℃, washing the resin after complete reaction, performing rotary evaporation on the obtained filtrate to obtain a precipitate, and freeze-drying to obtain the BLO-2.
(3) 200mg of Fmoc-Lys Wang Resin is put into a solid phase synthesis tube, N-Dimethylformamide (DMF) is added, the mixture is kept stand for 40 minutes to fully swell the Resin, the solvent is filtered out, piperidine DMF solution is added, and the solvent is filtered out after oscillation. Dissolving Fmoc-Ser-OH, 1-hydroxybenzotriazole and O-benzotriazol-tetramethylurea hexafluorophosphate in DMF, adding N, N-diisopropylethylamine, uniformly mixing, protecting from light, activating, adding into resin, stirring for 2 hours at 25 ℃ under the action of nitrogen blowing, carrying out suction filtration, washing with DMF and dichloromethane in sequence, and drying the solvent. And repeating the steps, sequentially adding activated Fmoc-His-OH, Fmoc-Glu-OH, Fmoc-His-OH, Fmoc-Gly-OH, Fmoc-Tyr-OH and Fmoc-Lys-OH into the resin, blowing nitrogen at 25 ℃ for stirring, washing the resin after complete reaction, performing rotary evaporation on the obtained filtrate to obtain a precipitate, and performing freeze drying to obtain the BLO-3.
Structural analysis and molecular weight determination of active peptides: electrospray ionization mass spectrometry (HPLC-ESI-MS) was performed on a SCIEX X500R quadrupole time-of-flight (Q-TOF) mass spectrometer. The mass range is set to be m/z 50-1500. Obtaining Q-TOF mass spectrum data in a positive mode, wherein the mass spectrum analysis conditions are as follows: CAD gas flow, 7L/min; the temperature of the drying gas is 550 ℃; ion spraying voltage, 5500V; and a deaggregation potential, 80V.
The analysis of BLO-1 is as follows: based on mass spectrum data analysis, the following results are obtained: 808.3743 is [ M + H]+Ion, 790.3669 is [ M-H2O+H]+Ion, 653.3066 is y5 ion, 566.2742 is y4 ion, 509.2111 is b4 ion, 380.1681 is b3 ion, 225.0982 is b3-b1, ion 110.0709 is [ His-COOH + H]+Ions. Finally, according to the mass spectrum data, the amino acid sequence of BLO-1 is Leu-Trp-Glu-His-Ser-His, namely the active peptide with the structure shown in the formula I.
The analysis of BLO-2 is as follows: 826.4213 is [ M + H ] based on analysis of mass spectrometry data2O+H]+Ion, 751.3910 is the y6 ion, 614.3317 is the y5 ion, 501.2470 is the y4 ion, 463.2436 is the b4 ion, 251.1508 is the y2 ion, 213.0988 is the b2 ion, 110.0712 is [ His-COOH + H]+Ions; finally, according to the mass spectrum data, the amino acid sequence of BLO-2 can be determined to be Tyr-Ser-Leu-His-Leu-His-Gly, namely the active peptide with the structure shown in the formula II.
The analysis of BLO-3 is as follows: based on mass spectrum data analysis, the following results are obtained: 857.3913 is [ M + H]+Ion, 839.3836 is [ M-H2O+H]+The ion, 752.3515 is the y6 ion, 615.2899 is the y5 ion, 486.2475 is the y4 ion, 324.1320 is the b5-b2 ion, 243.1092 is the b2 ion. Finally, according to the mass spectrum data, the amino acid sequence of BLO-3 can be determined to be Lys-Tyr-Gly-His-Glu-His-Ser, namely the active peptide with the structure shown in the formula III.
Examples of the experiments
In order to evaluate the biological activity of BLO-1, BLO-2, BLO-3 and active peptide compositions (compositions consisting of BLO-1, BLO-2 and BLO-3 in a molar ratio of 1:1:1, abbreviated as TBLO) prepared in example 1 of the present invention, the following effect test examples were conducted. BaP in the following experimental examples was benzo [ a ] pyrene.
(1) 10 adult nematodes were placed on NGM plates, inoculated with E.coli strain OP50 and laid eggs for about 5 hours to obtain a synchronized population. Then, L4 larval nematodes were used to evaluate the ability of BLO-1, BLO-2, BLO-3, TBLO to enhance the nematode's antioxidant stress at 20 ℃. Nematodes were incubated for 1 day on treated plates containing 0.10mM BaP and then transferred to NGM/OP50 plates containing 5mg/mL BLO-1 or BLO-2 or BLO-3 or TBLO.
(2) Locomotor ability was assessed at 20 ℃ using 1 day old adult caenorhabditis elegans. Caenorhabditis elegans were cultured for 1 day on treated plates containing 0.10mM BaP and transferred to NGM/OP50 plates containing 5mg/mL BLO-1 or BLO-2 or BLO-3 or TBLO. Caenorhabditis elegans was observed on days 6, 9 and 13. A type: the nematodes spontaneously and stably move, and sinusoidal symmetrical tracks are left; class C: caenorhabditis elegans moves the head or tail only when poked with a flexible wire; b type: caenorhabditis elegans stands for a and C. Each behavior class between N is more than or equal to 60 nematodes in each group.
(3) 3-day-old C.elegans were incubated with 0.10mM BaP for 12h and then transferred to freshly prepared NGM/OP50 plates containing 5mg/mL BLO-1 or BLO-2 or BLO-3 or TBLO for 24 h. All nematodes were then collected and washed 3 times with PBS. Then, the SOD activity and Malondialdehyde (MDA) content were determined using the kit. And (3) measuring the content of the active oxygen in the cells by using an active oxygen specific fluorescent probe DCFH-DA.
The experimental results are as follows:
as shown in table 1: BaP exposure significantly shortens nematode life; and TBLO can inhibit the life shortening of the nematode caused by BaP exposure and improve the average life of the caenorhabditis elegans. Active peptide composition TBLO has better protective activity than active peptide BLO-1 or BLO-2 or BLO-3 alone. This indicates that the active peptide has the function of delaying senility; wherein the active peptide composition obtained by combining BLO-1, BLO-2 and BLO-3 has the best effect of delaying aging.
TABLE 1 active peptides and compositions thereof against BaP-induced Life-reducing Activity
Furthermore, as shown in fig. 7, BaP exposure significantly reduced nematode motility; TBLO can inhibit nematode motility reduction caused by BaP exposure; active peptide composition TBLO has better protective activity than active peptide BLO-1 or BLO-2 or BLO-3.
As shown in fig. 8, TBLO was able to inhibit ROS production in c.elegans (fig. 8A), increase SOD activity (fig. 8B), and decrease MDA content (fig. 8C). Meanwhile, the research finds that the active peptide composition TBLO has better protective activity compared with the single action of BLO-1, BLO-2 or BLO-3.
While the invention has been described with reference to a preferred embodiment, it will be understood by those skilled in the art that various changes in form and detail may be made therein without departing from the spirit and scope of the invention.
Claims (10)
1. An active peptide having a structure of formula i, formula ii or formula iii:
2. an active peptide composition comprising a combination of any two or three of the active peptides having the structures shown in formula I, formula II and formula III.
3. The active peptide composition of claim 2, comprising active peptides having the structures of formula i, formula ii, and formula iii;
wherein the molar ratio of the active peptides with the structures shown in the formula I, the formula II and the formula III is 1-10: 1-10.
4. The active peptide composition of claim 3, wherein the molar ratio of the active peptides having the structures shown in formula I, formula II and formula III is 1-5: 1-5.
5. The active peptide composition of claim 4, wherein the molar ratio of active peptides having the structure of formula I, formula II, and formula III is 1:1: 1.
6. Use of an active peptide or active peptide composition according to any one of claims 1 to 5 for the preparation of a cosmetic, food, dietary supplement or pharmaceutical product.
7. The use according to claim 6, wherein the cosmetic, food, dietary supplement or pharmaceutical product is a cosmetic, food, dietary supplement or pharmaceutical product having an anti-aging effect.
8. The use of claim 6, wherein said aging is caused by environmental pollutants.
9. The use of claim 6, wherein the aging is caused by benzopyrene, an environmental pollutant.
10. The use according to claim 6, wherein the cosmetic, food, dietary supplement or pharmaceutical product is a cosmetic, food, dietary supplement or pharmaceutical product having a lipofuscin production inhibiting effect.
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