CN107903322B - Method for preparing antibacterial collagen based on safrole epoxidation modification - Google Patents
Method for preparing antibacterial collagen based on safrole epoxidation modification Download PDFInfo
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- CN107903322B CN107903322B CN201710927960.6A CN201710927960A CN107903322B CN 107903322 B CN107903322 B CN 107903322B CN 201710927960 A CN201710927960 A CN 201710927960A CN 107903322 B CN107903322 B CN 107903322B
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- ZMQAAUBTXCXRIC-UHFFFAOYSA-N safrole Chemical compound C=CCC1=CC=C2OCOC2=C1 ZMQAAUBTXCXRIC-UHFFFAOYSA-N 0.000 title claims abstract description 93
- 102000008186 Collagen Human genes 0.000 title claims abstract description 71
- 108010035532 Collagen Proteins 0.000 title claims abstract description 71
- 229920001436 collagen Polymers 0.000 title claims abstract description 71
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000006735 epoxidation reaction Methods 0.000 title claims abstract description 19
- 230000004048 modification Effects 0.000 title claims abstract description 16
- 238000012986 modification Methods 0.000 title claims abstract description 16
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 15
- 239000000463 material Substances 0.000 claims abstract description 11
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000012528 membrane Substances 0.000 claims description 14
- 239000008367 deionised water Substances 0.000 claims description 10
- 229910021641 deionized water Inorganic materials 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 6
- 230000002829 reductive effect Effects 0.000 claims description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 238000002791 soaking Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 3
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 3
- JYJVVHFRSFVEJM-UHFFFAOYSA-N iodosobenzene Chemical compound O=IC1=CC=CC=C1 JYJVVHFRSFVEJM-UHFFFAOYSA-N 0.000 claims description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 125000003277 amino group Chemical group 0.000 abstract description 2
- 125000003700 epoxy group Chemical group 0.000 abstract description 2
- 238000002715 modification method Methods 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- 244000005700 microbiome Species 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 238000002983 circular dichroism Methods 0.000 description 3
- 230000003013 cytotoxicity Effects 0.000 description 3
- 231100000135 cytotoxicity Toxicity 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 231100000820 toxicity test Toxicity 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 210000004204 blood vessel Anatomy 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 230000002459 sustained effect Effects 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- ZHTRFSJGUKYTPR-UHFFFAOYSA-N 2-octyl-1,2-thiazolidin-4-one Chemical compound CCCCCCCCN1CC(=O)CS1 ZHTRFSJGUKYTPR-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 101710172711 Structural protein Proteins 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000002473 artificial blood Substances 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 210000000845 cartilage Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- 230000002439 hemostatic effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 210000003041 ligament Anatomy 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 229940070805 p-chloro-m-cresol Drugs 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 210000000515 tooth Anatomy 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/78—Connective tissue peptides, e.g. collagen, elastin, laminin, fibronectin, vitronectin or cold insoluble globulin [CIG]
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Gastroenterology & Hepatology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Zoology (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Toxicology (AREA)
- Materials For Medical Uses (AREA)
- Peptides Or Proteins (AREA)
Abstract
The invention discloses a method for preparing antibacterial collagen based on safrole epoxidation modification. According to the method, a weak epoxidation reagent is used for modifying safrole, and then covalent reaction of an epoxy group and an amino group on a macromolecular side chain of collagen is utilized to covalently introduce the safrole into the collagen, so that a collagen substrate is endowed with good antibacterial activity. The collagen material obtained by the modification method has a long-acting antibacterial function, the triple helix structure of the collagen base material is not damaged, the inherent biocompatibility of the collagen base material can be completely reserved, and the collagen base material has a wide application prospect in the field of collagen base biomedical materials.
Description
Technical Field
The invention relates to a method for preparing antibacterial collagen based on safrole epoxidation modification, and belongs to the field of biomass materials.
Background
Collagen is the most important structural protein of connective tissues of higher vertebrates, widely exists in animal tissues in the forms of skin, bones, tendons, ligaments, nerves, blood vessels, teeth and the like, and plays roles of supporting organs and protecting organisms. Collagen, the most abundant protein in mammals, accounts for about 25-33% of the total protein in the body of the mammal. The collagen has special triple helix conformation, endows a plurality of excellent biological properties such as degradability, hemostatic property, histocompatibility and the like, so that the collagen is widely applied to tissue engineering such as skin substitutes, artificial cartilages, artificial blood vessels and the like, and various aspects such as medical health care, beauty and cosmetics, new functional materials and the like.
However, natural collagen is very vulnerable to microbial attack such as bacteria due to its own structural factors. During the growth and reproduction of the microorganisms, the collagen is subjected to enzymolysis to generate impurities, the quality of the collagen product is reduced, and the collagen is inactivated. In addition to this, the constant proliferation and metabolism of microorganisms leads to an increase in the endotoxin content of microorganisms in collagen preparations. Therefore, collagen-based products, especially collagen products for biomedical applications, must be treated to provide antimicrobial properties.
For a long time, it has proved to be an effective method to significantly improve the antibacterial and antiseptic properties of collagen products by adding small-molecule antibacterial agents (such as p-chloro-m-cresol, N-octyl isothiazolinone, paraben, etc.). However, this preservative strategy, which relies solely on the sustained dissolution of the antimicrobial agent, has the following drawbacks. First, the sustained dissolution antimicrobial mode necessarily lacks long-lasting efficacy. Secondly, many conventional antibacterial agents exhibit physiological toxicity to mammals while effectively killing harmful microorganisms such as bacteria, and the addition of such agents affects the inherent biocompatibility of natural collagen.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a method for preparing antibacterial collagen based on safrole epoxidation modification, which is characterized in that the method comprises the following process steps and conditions, and the parts of the used materials are all in parts by weight:
(1) performing epoxidation modification on safrole:
dissolving 12-20 parts of weak epoxidation reagent in 100-200 parts of solvent, adding 8-12 parts of safrole, and stirring at 20-30 ℃ for 12-24 hours; then washing the product with 2-7% alkali water solution for 3-5 times, and then washing with deionized water for 3-5 times; finally, drying the oil layer by anhydrous magnesium sulfate, filtering and then distilling under reduced pressure to obtain the epoxy safrole;
(2) epoxidized safrole graft modified collagen:
dissolving 10-20 parts of collagen in 0.2-0.5mol/L acetic acid aqueous solution, coating the mixture to form a film, and drying at 20-25 ℃ to constant weight; soaking the collagen membrane in water solution with pH of 7-9 and epoxy safrole concentration of 3-10%; and after 12-48 hours, taking out the collagen membrane, and washing the collagen membrane for 3-5 times by using deionized water to obtain the epoxidized safrole grafted and modified collagen.
In the above method, the weak epoxidation reagent in step (1) is one or more of m-chloroperoxybenzoic acid, iodosobenzene, and tert-butyl peroxide.
In the above method, the solvent in step (1) is one or more of dichloromethane, chloroform and carbon tetrachloride.
In the above method, the alkali in step (1) is one or more of sodium hydroxide, potassium hydroxide and sodium bicarbonate.
Compared with the prior art, the invention has the following positive effects:
1. according to the invention, the safrole is modified by adopting a weak epoxidation reagent, and the epoxidation reaction only acts on allyl in the safrole molecule and does not affect the remaining structure domain with the antibacterial effect, so that the antibacterial activity of the epoxidized and modified safrole is retained.
2. After the safrole is subjected to epoxidation modification, the epoxy group of the safrole can react with the amino group on the collagen macromolecular chain, so that the safrole is covalently fixed on the collagen material, and the antibacterial function of the collagen material has long-acting property.
3. The reaction conditions of the epoxidized safrole and the collagen are very mild, so that the antibacterial collagen prepared by adopting the technical route of the invention does not damage the inherent triple helix structure and biocompatibility of the collagen material.
Drawings
Fig. 1 is a preparation route of the epoxidized safrole according to the present invention.
Fig. 2 is a schematic diagram of the covalent reaction between the epoxidized safrole and collagen macromolecules according to the present invention.
Detailed Description
The invention is described in detail below with reference to examples, which are intended to be illustrative only and not to be construed as limiting the scope of the invention, and many insubstantial modifications and variations of the invention can be made by an engineer skilled in the art based on the teachings of the invention.
Example 1:
(1) performing epoxidation modification on safrole:
dissolving 12 parts of m-chloroperoxybenzoic acid in 100 parts of dichloromethane, adding 8 parts of safrole, and stirring at 20 ℃ for 24 hours; thereafter, the product was washed 3 times with 2% aqueous sodium hydroxide solution and then 3 times with deionized water; finally, drying the oil layer by anhydrous magnesium sulfate, filtering and then distilling under reduced pressure to obtain the epoxy safrole;
(2) epoxidized safrole graft modified collagen:
dissolving 10 parts of collagen in 0.2mol/L acetic acid aqueous solution, coating the mixture to form a film, and drying at 20 ℃ to constant weight; soaking the collagen membrane in water solution with pH of 7 and epoxidized safrole concentration of 3%; after 12 hours, the collagen membrane is taken out and washed by deionized water for 3 times to obtain the epoxidized safrole graft modified collagen.
The results of infrared spectroscopy and circular dichroism experiments show that the three-strand helical structure of the collagen is not damaged by the modification; toxicity experiments show that the LD50 value of the product is more than 55g/kg, the cytotoxicity grade is 0 grade (ISO10993-5), so the product can be regarded as safe and nontoxic; the modified collagen obtained by the method has the bacteriostasis rate of more than 90.2 percent on staphylococcus aureus, escherichia coli and pseudomonas aeruginosa (a plate counting method).
Example 2:
(1) performing epoxidation modification on safrole:
dissolving 15 parts of iodosobenzene in 150 parts of chloroform, adding 10 parts of safrole, and stirring at 25 ℃ for 20 hours; thereafter, the product was washed 4 times with 5% aqueous potassium hydroxide solution and 5 times with deionized water; finally, drying the oil layer by anhydrous magnesium sulfate, filtering and then distilling under reduced pressure to obtain the epoxy safrole;
(2) epoxidized safrole graft modified collagen:
dissolving 15 parts of collagen in 0.4mol/L acetic acid aqueous solution, coating the mixture to form a film, and drying at 22 ℃ to constant weight; soaking the collagen membrane in water solution with pH of 8 and epoxidized safrole concentration of 7%; and after 24 hours, taking out the collagen membrane, and washing the collagen membrane for 4 times by using deionized water to obtain the epoxidized safrole grafted and modified collagen.
The results of infrared spectroscopy and circular dichroism experiments show that the three-strand helical structure of the collagen is not damaged by the modification; toxicity experiments show that the LD50 value of the product is more than 60g/kg, the cytotoxicity grade is 0 grade (ISO10993-5), so the product can be regarded as safe and nontoxic; the modified collagen obtained by the method has the bacteriostasis rate of more than 91.6 percent on staphylococcus aureus, escherichia coli and pseudomonas aeruginosa (a plate counting method).
Example 3:
(1) performing epoxidation modification on safrole:
dissolving 20 parts of tert-butyl peroxide in 200 parts of carbon tetrachloride, adding 12 parts of safrole, and stirring at 30 ℃ for 12 hours; thereafter, the product was washed 5 times with 7% aqueous sodium bicarbonate solution and 5 times with deionized water; finally, drying the oil layer by anhydrous magnesium sulfate, filtering and then distilling under reduced pressure to obtain the epoxy safrole;
(2) epoxidized safrole graft modified collagen:
dissolving 20 parts of collagen in 0.5mol/L acetic acid aqueous solution, coating the mixture to form a film, and drying at 25 ℃ to constant weight; soaking the collagen membrane in an aqueous solution with the pH value of 9 and the concentration of the epoxidized safrole of 10 percent; and after 48 hours, taking out the collagen membrane, and washing the collagen membrane for 5 times by using deionized water to obtain the epoxidized safrole grafted and modified collagen.
The results of infrared spectroscopy and circular dichroism experiments show that the three-strand helical structure of the collagen is not damaged by the modification; toxicity experiments show that the LD50 value of the product is more than 60g/kg, the cytotoxicity grade is 0 grade (ISO10993-5), so the product can be regarded as safe and nontoxic; the modified collagen obtained by the method has the bacteriostasis rate of more than 91.2 percent on staphylococcus aureus, escherichia coli and pseudomonas aeruginosa (a plate counting method).
Claims (3)
1. A method for preparing antibacterial collagen based on safrole epoxidation modification is characterized in that the method comprises the following process steps and conditions, and the parts of the used materials are the parts by weight:
(1) performing epoxidation modification on safrole:
dissolving 12-20 parts of weak epoxidation reagent in 100-200 parts of solvent, adding 8-12 parts of safrole, and stirring at 20-30 ℃ for 12-24 hours; then washing the product with 2-7% alkali water solution for 3-5 times, and then washing with deionized water for 3-5 times; finally, drying the oil layer by anhydrous magnesium sulfate, filtering and then distilling under reduced pressure to obtain the epoxy safrole; the weak epoxidation reagent is one or more of m-chloroperoxybenzoic acid, iodosobenzene and tert-butyl peroxide;
(2) epoxidized safrole graft modified collagen:
dissolving 10-20 parts of collagen in 0.2-0.5mol/L acetic acid aqueous solution, coating the above collagen-acetic acid aqueous solution mixture to form a film, and drying at 20-25 deg.C to constant weight; soaking the collagen membrane in an aqueous solution prepared from the epoxidized safrole obtained in the step (1) and having a pH value of 7-9 and a concentration of 3-10%; and after 12-48 hours, taking out the collagen membrane, and washing the collagen membrane for 3-5 times by using deionized water to obtain the epoxidized safrole grafted and modified collagen.
2. The method for preparing antibacterial collagen according to claim 1, wherein the solvent in step (1) is one or more of dichloromethane, chloroform and carbon tetrachloride.
3. The method for preparing antibacterial collagen according to claim 1, wherein the alkali in step (1) is one or more of sodium hydroxide, potassium hydroxide and sodium bicarbonate.
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| CN103505759A (en) * | 2013-07-04 | 2014-01-15 | 四川大学 | Method used for modifying collagen with epoxy quaternary ammonium salt |
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| CN106349718A (en) * | 2016-10-25 | 2017-01-25 | 齐鲁工业大学 | Preparation method for antibacterial collagen |
| CN107011683A (en) * | 2017-04-17 | 2017-08-04 | 四川大学 | A kind of antibacterial and antioxidative edible gelatin composite film and preparation method thereof |
| WO2017192923A1 (en) * | 2016-05-05 | 2017-11-09 | Monosol Rx, Llc | Pharmaceutical compositions with enhanced permeation |
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2017
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Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007042037A1 (en) * | 2005-10-07 | 2007-04-19 | Lifecycle Pharma A/S | Tacrolimus combination products |
| CN103505759A (en) * | 2013-07-04 | 2014-01-15 | 四川大学 | Method used for modifying collagen with epoxy quaternary ammonium salt |
| CN104013995A (en) * | 2014-06-26 | 2014-09-03 | 四川大学 | Oxidation chitosan graft modified porcine dermal collagen micro-nano fiber membrane and preparation method thereof |
| WO2017192923A1 (en) * | 2016-05-05 | 2017-11-09 | Monosol Rx, Llc | Pharmaceutical compositions with enhanced permeation |
| CN106349718A (en) * | 2016-10-25 | 2017-01-25 | 齐鲁工业大学 | Preparation method for antibacterial collagen |
| CN107011683A (en) * | 2017-04-17 | 2017-08-04 | 四川大学 | A kind of antibacterial and antioxidative edible gelatin composite film and preparation method thereof |
Non-Patent Citations (3)
| Title |
|---|
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| Effects of arecoline, safrole, and nicotine on collagen phagocytosis by human buccal mucosal fibroblasts as a possible mechanism for oral submucous fibrosis in Taiwan;Dean-Hwa Shieh;《Oral Pathol Med》;20041231;第33卷;第581-587页 * |
| 芳樟油对大肠杆菌气相杀菌机制研究;吴克刚;《广东省食品学会第六次会员大会暨学术研讨会论文集》;20121231;第47-56页 * |
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