CN114223786A - Application of nerolidol modified oligosaccharide as feed additive - Google Patents
Application of nerolidol modified oligosaccharide as feed additive Download PDFInfo
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- CN114223786A CN114223786A CN202111652148.XA CN202111652148A CN114223786A CN 114223786 A CN114223786 A CN 114223786A CN 202111652148 A CN202111652148 A CN 202111652148A CN 114223786 A CN114223786 A CN 114223786A
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/163—Sugars; Polysaccharides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
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Abstract
The invention discloses application of nerolidol modified oligosaccharide as a feed additive, wherein the modified oligosaccharide is prepared by carrying out modification reaction on chitosan oligosaccharide and trans-nerolidol in the presence of a mixed solvent containing pyridine and a palladium-containing catalyst. The nerolidol modified oligosaccharide has improved antibacterial property against Escherichia coli and Staphylococcus aureus; and the growth promoting effect is further improved.
Description
Technical Field
The invention belongs to the technical field of anti-substitution additives, and particularly relates to an application of nerolidol modified oligosaccharide as a feed additive.
Background
With the continuous improvement of the development level of the economic society, large-scale intensification becomes the main direction of the development of the animal husbandry in China. Since the antibiotics are widely used as the growth-promoting feed additive, obvious economic benefits are created for the breeding industry. However, the use of feeding antibiotics in a sub-dosage for a long time has been proved by many researches to form a source of drug resistance of various pathogenic bacteria and cause endogenous infection and superinfection of livestock, so that the health condition of the livestock is seriously influenced. The drug residue in the livestock and poultry product not only influences the quality of the livestock and poultry product, but also can cause pathogenic bacteria in human bodies to generate drug resistance to the residual antibiotics, thereby directly threatening the health of human beings.
For the healthy development of the feed industry and the livestock breeding industry, people have more healthy thinking, antibiotics are cautiously used or even forbidden, and the active development and use of safe, nontoxic and harmless green feed additives are urgent. The green feed additives which are researched more by people at present comprise: oligosaccharide, prebiotics, enzyme preparation, acidifier, antibacterial peptide and Chinese herbal medicine.
Among these, oligosaccharides are a more interesting class of additives. Researches show that the oligosaccharide has the effects of inhibiting the growth of harmful bacteria, promoting the absorption and utilization of trace elements of iron and calcium, improving the production performance and the immune function of animals, strengthening the state of intestinal tissues and regulating the microbial ecology, has the capability of replacing part of antibiotics in animal feed, and provides practical basis for antibiotic-free, green and sustainable culture.
However, when either animal-derived oligosaccharides or plant-derived oligosaccharides are used directly as feed additives, they are often unsatisfactory in bacteriostatic properties due to solubility and group limitations. For this reason, a large number of researchers have been working on improving the antibacterial properties of oligosaccharides by chemical modification. The common idea of chemical modification is to introduce natural molecules, such as polyphenols, polypeptides, organic acids and organic alcohols, etc., on the amino group at position 2 and the hydroxyl groups at positions 3 and 6.
Lin Yue et al prepared geraniol-modified chitosan oligosaccharide derivatives by substitution reaction. In the reaction process, the amino group of the chitosan oligosaccharide is protected and deprotected in sequence, and finally geraniol is introduced into the hydroxyl group of the chitosan oligosaccharide. The results show that the oligosaccharide derivative has good solubility, thermal stability and antibacterial property. However, the modified chitosan oligosaccharide has complicated reaction steps and low reaction yield, and the antibacterial performance of the modified chitosan oligosaccharide against escherichia coli and staphylococcus aureus still needs to be improved.
On the other hand, related researches show that the oligosaccharide can regulate the intestinal microflora of animals, improve the intestinal mucosa structure of cultured animals, improve the functions of digestive organs, promote the absorption of nutrient substances and the growth of the cultured animals, improve the weight gain rate of the cultured animals, and can be used as a growth promoter to replace part of antibiotics.
Chinese patent application publication CN112586611A discloses the use of a modified oligosaccharide as a feed additive, wherein the modified oligosaccharide is obtained by taking chitosan oligosaccharide and 3-bromo-3, 7-dimethyl-1, 6-octadiene as raw materials through modification reaction, purification steps and freeze drying. The modified oligosaccharide additive has better antibacterial performance against escherichia coli and staphylococcus aureus; but also has better growth promoting effect.
However, the antibacterial properties against escherichia coli and staphylococcus aureus and the growth promoting effect as an alternative additive of the aforementioned modified oligosaccharides still remain to be further improved.
Disclosure of Invention
The invention aims to provide application of nerolidol modified oligosaccharide as a feed additive.
In order to solve the technical problems, the invention adopts the following technical scheme: the application of nerolidol modified oligosaccharide as a feed additive is characterized in that the modified oligosaccharide is prepared by carrying out modification reaction on chitosan oligosaccharide and trans-nerolidol in the presence of a mixed solvent containing pyridine and a palladium-containing catalyst.
The use according to the invention, wherein the modified oligosaccharide is added in an amount of 50-400mg/kg, calculated on the weight of the basal feed.
The use of the invention, wherein the mixed solvent is prepared by mixing the following components in a volume ratio of 1: 1 DMSO and pyridine.
The use according to the present invention, wherein the average molecular weight of the chitosan oligosaccharide is = 1000-; the deacetylation degree is more than or equal to 95 percent.
The application of the invention is characterized in that the molar ratio of trans-nerolidol to chitosan oligosaccharide is (2-2.8): 1.
the use according to the invention, wherein the palladium-containing catalyst is selected from bis (di-tert-butyl (4-dimethylaminophenyl) phosphine) palladium dichloride.
The use according to the invention, wherein the palladium-containing catalyst is used in an amount corresponding to 0.1-1mol% of the amount of chitosan oligosaccharide.
The application of the invention, wherein the modification reaction temperature is 40-60 ℃; the reaction time is 3-9 h.
The use according to the invention further comprises the purification steps of soxhlet extraction of petroleum ether and dialysis against distilled water.
The use according to the invention, wherein the dialysis uses dialysis bags with a molecular weight cut-off of 1000.
Compared with the prior art, the nerolidol modified oligosaccharide is used as a feed additive, and the antibacterial performance of escherichia coli and staphylococcus aureus is further improved; and the growth promoting effect is further improved.
Detailed Description
The invention will be further illustrated with reference to specific embodiments.
It should be understood that the detailed description of the invention is merely illustrative of the spirit and principles of the invention and is not intended to limit the scope of the invention. Furthermore, it should be understood that various changes, substitutions, deletions, modifications or adjustments may be made by those skilled in the art after reading the disclosure of the present invention, and such equivalents are also within the scope of the invention as defined in the appended claims.
In the present invention, all parts are parts by weight unless otherwise specified.
Example 1
Chitooligosaccharides (average molecular weight =1500 daltons; degree of deacetylation = 97%) were dissolved in a volume ratio of 1: 1 in a mixed solvent composed of DMSO and pyridine, and stirring until the solution is clear and transparent. Adding trans-nerolidol (available from Shanghai Ruiz Biotech Co., Ltd., CAS: 40716-66-3) to the mixture; the molar ratio of the trans-nerolidol to the chitosan oligosaccharide is 2.4: 1. then, bis (di-tert-butyl (4-dimethylaminophenyl) phosphine) palladium dichloride (available from Merck chemical, China Co., CAS: 887919-35-9) was added in an amount of 0.3mol% based on the amount of chitosan oligosaccharide. Carrying out modification reaction under the conditions of stirring and 50 ℃; the reaction time was 6 h. And after the modification reaction is finished, cooling to room temperature, adding acetone to separate out a precipitate, standing, centrifuging, collecting the precipitate, and drying in vacuum at 40 ℃ for 3 hours to obtain a crude product. The crude product is further purified; the purification conditions are as follows: soxhlet extraction with petroleum ether for 12h, and vacuum drying at 40 deg.C for 3 h; and (3) putting the dried product into a dialysis bag with the molecular weight cutoff of 1000, dialyzing distilled water for 36h, adding acetone to separate out a precipitate when the product is concentrated to 1/5 volume, and performing vacuum drying at 40 ℃ for 3h to obtain the nerolidol modified oligosaccharide.
Compared with unmodified chitosan oligosaccharide, in an IR spectrum, the carbonyl stretching vibration peak of nerolidol modified oligosaccharide is shifted to 1638cm-1(ii) a And 1515cm-1The peak of the amino group stretching vibration of (2) is weakened. In that1In an H NMR spectrum, the nerolidol modified oligosaccharide increases the C = C-H chemical shift values of 5.17ppm, 5.19ppm, 5.21ppm, 5.23ppm and 5.82 ppm.
According to the plate diffusion method disclosed in the embodiment of Chinese patent application publication CN112521527A, the bacteriostatic performance of nerolidol modified oligosaccharide on escherichia coli and staphylococcus aureus is studied. The diameters of the bacteriostatic circle of the nerolidol modified oligosaccharide on escherichia coli and staphylococcus aureus are respectively 13.6 +/-0.2 mm and 17.1 +/-0.2 mm.
Animal testing
24 female Kunming mice with the age of 4 weeks who just had broken breast were randomly divided into 3 groups of 8 mice each. The 3 groups of basic feeds are the same and are all experimental rat growth and reproduction feeds of cooperative medical and biological engineering Limited liability company of Jiangsu province, and the feeds do not contain antibiotics. 200mg/kg of nerolidol-modified oligosaccharide additive of example 1 (test group I), 0mg/kg of modified oligosaccharide additive of example 1 (control group I), and 200mg/kg of unmodified oligosaccharide of example 1 (control group II) were added to the basal diet, respectively, and fed continuously for 4 weeks. The average daily gain (g/d) was calculated for each group and was 0.77 + -0.14 g/d, 0.51 + -0.11 g/d and 0.62 + -0.17 g/d for test group I, control group I and control group II, respectively.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention shall fall within the protection scope of the present invention.
Claims (10)
1. The application of nerolidol modified oligosaccharide as a feed additive is characterized in that the modified oligosaccharide is prepared by carrying out modification reaction on chitosan oligosaccharide and trans-nerolidol in the presence of a mixed solvent containing pyridine and a palladium-containing catalyst.
2. Use according to claim 1, wherein the modified oligosaccharide is added in an amount of 50-400mg/kg, calculated on the weight of the basal feed.
3. The use according to claim 1, wherein the mixed solvent is a mixture of solvents in a volume ratio of 1: 1 DMSO and pyridine.
4. The use according to claim 1, wherein the average molecular weight of the chitosan oligosaccharide is =1000 and 2000 daltons; the deacetylation degree is more than or equal to 95 percent.
5. The use according to claim 1, wherein the molar ratio of trans-nerolidol to chitosan oligosaccharide is (2-2.8): 1.
6. use according to claim 1, wherein the palladium-containing catalyst is selected from bis (di-tert-butyl (4-dimethylaminophenyl) phosphine) palladium dichloride.
7. Use according to claim 1, wherein the palladium-containing catalyst is used in an amount corresponding to 0.1-1mol% of the amount of chitosan oligosaccharide.
8. Use according to claim 1, wherein the modification reaction temperature is 40-60 ℃; the reaction time is 3-9 h.
9. The use according to claim 1, further comprising the purification steps of soxhlet extraction of petroleum ether and dialysis against distilled water.
10. Use according to claim 1, wherein the dialysis uses dialysis bags with a molecular weight cut-off of 1000.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202111652148.XA CN114223786A (en) | 2021-12-31 | 2021-12-31 | Application of nerolidol modified oligosaccharide as feed additive |
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| CN202111652148.XA CN114223786A (en) | 2021-12-31 | 2021-12-31 | Application of nerolidol modified oligosaccharide as feed additive |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103083368A (en) * | 2013-02-05 | 2013-05-08 | 中国林业科学研究院林产化学工业研究所 | Preparation method of ginkgo leaf lipoid components having antibacterial activities |
| CN111333750A (en) * | 2020-03-24 | 2020-06-26 | 江南大学 | Chitosan oligosaccharide-N-geraniol derivative and preparation method and application thereof |
| CN111620966A (en) * | 2020-06-23 | 2020-09-04 | 江南大学 | Chitosan oligosaccharide-N-linalool copolymer and preparation method and application thereof |
| CN111732674A (en) * | 2020-07-31 | 2020-10-02 | 江南大学 | Chitosan oligosaccharide-M-cinnamyl alcohol derivative, preparation method and application thereof |
| CN112521527A (en) * | 2020-12-30 | 2021-03-19 | 重庆市六九畜牧科技股份有限公司 | Modified oligosaccharide and preparation method thereof |
| CN112586611A (en) * | 2020-12-30 | 2021-04-02 | 重庆市六九畜牧科技股份有限公司 | Application of modified oligosaccharide as feed additive |
-
2021
- 2021-12-31 CN CN202111652148.XA patent/CN114223786A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103083368A (en) * | 2013-02-05 | 2013-05-08 | 中国林业科学研究院林产化学工业研究所 | Preparation method of ginkgo leaf lipoid components having antibacterial activities |
| CN111333750A (en) * | 2020-03-24 | 2020-06-26 | 江南大学 | Chitosan oligosaccharide-N-geraniol derivative and preparation method and application thereof |
| CN111620966A (en) * | 2020-06-23 | 2020-09-04 | 江南大学 | Chitosan oligosaccharide-N-linalool copolymer and preparation method and application thereof |
| CN111732674A (en) * | 2020-07-31 | 2020-10-02 | 江南大学 | Chitosan oligosaccharide-M-cinnamyl alcohol derivative, preparation method and application thereof |
| CN112521527A (en) * | 2020-12-30 | 2021-03-19 | 重庆市六九畜牧科技股份有限公司 | Modified oligosaccharide and preparation method thereof |
| CN112586611A (en) * | 2020-12-30 | 2021-04-02 | 重庆市六九畜牧科技股份有限公司 | Application of modified oligosaccharide as feed additive |
Non-Patent Citations (1)
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| 陶冉;王成章;孔振武;: "银杏叶类脂成分与聚戊烯醇的协同抑菌作用", 中国实验方剂学杂志, vol. 19, no. 17, pages 203 * |
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