CN114052126A - Rumen-bypass coated product containing (1,2,5, 6-O-selenium) -D-ganoderic acid glucose and preparation method thereof - Google Patents
Rumen-bypass coated product containing (1,2,5, 6-O-selenium) -D-ganoderic acid glucose and preparation method thereof Download PDFInfo
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- CN114052126A CN114052126A CN202110995089.XA CN202110995089A CN114052126A CN 114052126 A CN114052126 A CN 114052126A CN 202110995089 A CN202110995089 A CN 202110995089A CN 114052126 A CN114052126 A CN 114052126A
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- 239000011669 selenium Substances 0.000 title claims abstract description 48
- 229910052711 selenium Inorganic materials 0.000 title claims abstract description 44
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 title claims abstract description 36
- 239000008103 glucose Substances 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title claims description 32
- RDMQPKIDHAFXKA-JNORPAGFSA-N Ganoderic Acid Am1 Chemical compound C([C@@]12C)C[C@H](O)C(C)(C)[C@@H]1CC(=O)C1=C2C(=O)C[C@]2(C)[C@@H]([C@@H](CC(=O)CC(C)C(O)=O)C)CC(=O)[C@]21C RDMQPKIDHAFXKA-JNORPAGFSA-N 0.000 claims abstract description 38
- CBOJBBMQJBVCMW-BTVCFUMJSA-N (2r,3r,4s,5r)-2-amino-3,4,5,6-tetrahydroxyhexanal;hydrochloride Chemical compound Cl.O=C[C@H](N)[C@@H](O)[C@H](O)[C@H](O)CO CBOJBBMQJBVCMW-BTVCFUMJSA-N 0.000 claims abstract description 19
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229960001911 glucosamine hydrochloride Drugs 0.000 claims abstract description 19
- 239000011162 core material Substances 0.000 claims abstract description 18
- 210000004767 rumen Anatomy 0.000 claims abstract description 18
- BSEYIQDDZBVTJY-UHFFFAOYSA-N Ganoderic acid A Natural products CC(CC(=O)CCC1CC(O)C2(C)C3=C(C(=O)CC12C)C4(C)CCC(=O)C(C)(C)C4CC3O)C(=O)O BSEYIQDDZBVTJY-UHFFFAOYSA-N 0.000 claims abstract description 16
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 15
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 48
- 239000000243 solution Substances 0.000 claims description 45
- 238000003756 stirring Methods 0.000 claims description 38
- 239000000463 material Substances 0.000 claims description 31
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 229930182735 Ganoderic acid Natural products 0.000 claims description 23
- 239000004925 Acrylic resin Substances 0.000 claims description 16
- 229920000178 Acrylic resin Polymers 0.000 claims description 16
- 239000011248 coating agent Substances 0.000 claims description 16
- 238000000576 coating method Methods 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 16
- 229920001661 Chitosan Polymers 0.000 claims description 14
- 235000019482 Palm oil Nutrition 0.000 claims description 14
- 239000002540 palm oil Substances 0.000 claims description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 235000019441 ethanol Nutrition 0.000 claims description 12
- 238000005303 weighing Methods 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 239000001632 sodium acetate Substances 0.000 claims description 8
- 235000017281 sodium acetate Nutrition 0.000 claims description 8
- 239000000725 suspension Substances 0.000 claims description 8
- 239000011259 mixed solution Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 238000004440 column chromatography Methods 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000000889 atomisation Methods 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 238000007865 diluting Methods 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 238000011049 filling Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 230000002572 peristaltic effect Effects 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000007921 spray Substances 0.000 claims description 4
- 238000005507 spraying Methods 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 229910021642 ultra pure water Inorganic materials 0.000 claims description 4
- 239000012498 ultrapure water Substances 0.000 claims description 4
- 238000001291 vacuum drying Methods 0.000 claims description 4
- 238000010790 dilution Methods 0.000 claims description 3
- 239000012895 dilution Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 2
- 238000000967 suction filtration Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 2
- 241000283690 Bos taurus Species 0.000 abstract description 21
- 239000008267 milk Substances 0.000 abstract description 18
- 235000013336 milk Nutrition 0.000 abstract description 18
- 210000004080 milk Anatomy 0.000 abstract description 18
- 210000005075 mammary gland Anatomy 0.000 abstract description 11
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 abstract description 9
- 239000008101 lactose Substances 0.000 abstract description 9
- 235000013365 dairy product Nutrition 0.000 description 7
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 241000222336 Ganoderma Species 0.000 description 2
- 210000000481 breast Anatomy 0.000 description 2
- 210000003754 fetus Anatomy 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000006651 lactation Effects 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 230000035882 stress Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- 241000005601 Trisetum Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 235000014590 basal diet Nutrition 0.000 description 1
- 230000004637 cellular stress Effects 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000013400 design of experiment Methods 0.000 description 1
- 235000013325 dietary fiber Nutrition 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- -1 ganoderic acid compound Chemical class 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000036542 oxidative stress Effects 0.000 description 1
- 230000003334 potential effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000004460 silage Substances 0.000 description 1
- 235000021195 test diet Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/10—Feeding-stuffs specially adapted for particular animals for ruminants
-
- 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
-
- 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
- A23K20/105—Aliphatic or alicyclic compounds
-
- 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
- A23K20/158—Fatty acids; Fats; Products containing oils or fats
-
- 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
-
- 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
- A23K20/20—Inorganic substances, e.g. oligoelements
- A23K20/30—Oligoelements
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K40/00—Shaping or working-up of animal feeding-stuffs
- A23K40/30—Shaping or working-up of animal feeding-stuffs by encapsulating; by coating
- A23K40/35—Making capsules specially adapted for ruminants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7008—Compounds having an amino group directly attached to a carbon atom of the saccharide radical, e.g. D-galactosamine, ranimustine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/04—Sulfur, selenium or tellurium; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/0068—Rumen, e.g. rumen bolus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/14—Drugs for genital or sexual disorders; Contraceptives for lactation disorders, e.g. galactorrhoea
Abstract
The invention provides a rumen-bypass envelope product containing (1,2,5, 6-O-selenium) -D-ganoderic acid glucose, wherein a core material formula comprises glucosamine hydrochloride, selenium and ganoderic acid A, wherein the weight ratio of the glucosamine hydrochloride, the selenium and the ganoderic acid A is 1:1:2 or 3:3: 4; the rumen bypass envelope product can improve milk yield and lactose synthesis amount of milk cows, improve glucose utilization efficiency of milk cows, and well maintain the health of mammary glands of milk cows.
Description
Technical Field
The invention belongs to the technical field of medicines, and particularly relates to a rumen bypass envelope product which can adjust the utilization efficiency of glucose of high-yield cows and optimize the health of mammary glands.
Background
The elimination of mammary gland metabolic oxidation free radical and the efficient synthesis of lactose are the guarantee for guaranteeing the health and high yield of the dairy cows. At present, substances capable of efficiently removing mammary gland oxidation free radicals and regulating efficient lactose synthesis are newly researched, and earlier researches show that the addition of ganoderic acid A into milk goat cells can improve the proportion of cell glucose for lactose synthesis, and simultaneously reduce intracellular stress parameters (Cai,2020, Faseb Journal) and prompt that the ganoderic acid has the potential effect of maintaining the stable state of mammary glands as an additive. However, we found that the mammary gland metabolic homeostasis, glucose utilization efficiency and cellular stress of cows could not be improved by merely coating ganoderic acid through the rumen or adding uncoated ganoderic acid (not published). Therefore, the synthesis of the ganoderic acid compound and the adjustment of rumen-bypass coating parameters are combined to form a novel rumen-bypass coating yield containing ganoderic acid, and the novel ganoderic acid-bypass coating yield is used as a feed additive for dairy cow production.
Disclosure of Invention
The invention provides a rumen bypass envelope product containing (1,2,5, 6-O-selenium) -D-ganoderic acid glucose and a preparation method thereof, and the rumen bypass envelope product can improve the utilization efficiency of glucose of high-yield cows and optimize the health of mammary glands.
In order to realize the purpose of the invention, the invention adopts the following technical scheme:
the rumen-bypass envelope product containing (1,2,5, 6-O-selenium) -D-ganoderic acid glucose comprises glucosamine hydrochloride, selenium and ganoderic acid A, wherein the weight ratio of the glucosamine hydrochloride, the selenium and the ganoderic acid A is 1:1:2 or 3:3: 4.
The invention also aims to provide a preparation method of the rumen bypass envelope product containing (1,2,5, 6-O-selenium) -D-ganoderic acid glucose, which adopts the following technical scheme:
the preparation method of the rumen bypass envelope product containing (1,2,5, 6-O-selenium) -D-ganoderic acid glucose comprises the following steps:
preparation of a coating film:
1.1 preparation of chitosan wall material solution:
preparing an acetic acid solution; weighing chitosan, adding the chitosan into an acetic acid solution, stirring and dissolving to prepare a wall material preparation solution;
1.2 preparation of palm oil wall material suspension:
weighing palm oil, adding the palm oil into an alcohol solution, stirring and dissolving to prepare palm oil suspension;
1.3 preparation of acrylic resin wall material solution:
weighing acrylic resin, adding the acrylic resin into an alcohol solution, stirring and dissolving to prepare an acrylic resin solution;
1.4 mixing:
the three wall material solutions obtained in the steps 1.1, 1.2 and 1.3 are mixed according to the volume ratio of 2.3-2.7:3.3-3.7: 3.8-4.2; preparing a core material:
2.1 Synthesis of 1,2,5, 6-O-selenium-D-glucosamine
Adding selenium into acetic anhydride, stirring and cooling to 0 ℃, adding glucosamine hydrochloride, slowly dropwise adding concentrated sulfuric acid, stirring overnight (about the phenomenon can not occur, uncertain characters can not appear), then slowly dropwise adding absolute ethyl alcohol, stirring at the temperature of 0 ℃ until white solid is separated out, performing suction filtration, washing the filtered white substance with ethyl acetate until no acid smell exists, performing vacuum drying to obtain a white substance, further dissolving the white substance in ultrapure water, adding sodium acetate while stirring to obtain separated white solid, continuing stirring until the sodium acetate is completely dissolved, extracting with ethyl acetate, and performing reduced pressure concentration to remove a solvent to obtain the white solid: 1,2,5, 6-O-selenium-D-glucosamine;
2.2 Synthesis of (1,2,5, 6-O-Se) -D-Ganoderic acid glucose
Slowly adding aqueous solution of Ganoderma acid dropwise with 1,2,5, 6-O-selenium-D-glucosamine and Ganoderma acid solution at room temperature under nitrogen protection, stirring, distilling under reduced pressure to remove organic solvent, adding ethyl acetate for dilution, and adding NaHCO3Washing with anhydrous MgSO4Drying, distilling under reduced pressure to remove organic solvent to obtain light yellow paste, separating by column chromatography to obtain white solid, and crystallizing with ethanol to obtain white crystal;
preparing a rumen bypass coated ganoderic acid preparation:
firstly, filling the core material (1,2,5, 6-O-selenium) -D-ganoderic acid glucose obtained in the step 2.2 into a coating chamber, then adjusting the atomization pressure and the air inlet temperature to enable the solidified mixture to be in a fluidized state and reach 50 ℃, and then spraying the mixed wall material solution on the core material through a spray gun of the coating chamber by a peristaltic pump to prepare the rumen-protected ganoderic acid product, wherein the volume ratio of the core material to the wall material mixed solution is 43-47: 53-57.
Preferably, the silica gel in column chromatography in step 2.2 is 400-500 mesh, and the mobile phase is ethyl acetate to methanol in a volume ratio of 10: 1.
The rumen bypass envelope product containing (1,2,5, 6-O-selenium) -D-ganoderic acid glucose provided by the invention can improve milk yield and lactose synthesis amount of dairy cows, improve the utilization efficiency of glucose of the dairy cows, and better maintain the health of mammary glands of the dairy cows.
Detailed Description
The present invention is further illustrated by the following specific examples.
Example 1
The preparation method of rumen bypass envelope product containing (1,2,5, 6-O-selenium) -D-ganoderic acid glucose (glucosamine hydrochloride, the weight ratio of selenium to ganoderic acid A is 1:1:2) comprises the following steps:
1. preparation of a coating film:
1.1 preparation of chitosan wall material solution:
preparing 900mL of 3.5% acetic acid solution; weighing 35g of chitosan, adding the chitosan into an acetic acid solution, stirring and dissolving the chitosan in water at 35 ℃ to prepare a wall material preparation solution;
1.2 preparation of palm oil wall material suspension:
weighing 35g of palm oil, adding 900m L90% alcohol solution, stirring to dissolve, and preparing into 3% palm oil suspension;
1.3 preparation of acrylic resin wall material solution:
weighing 35g of acrylic resin, adding 85% alcohol solution, stirring to dissolve the acrylic resin, and preparing acrylic resin solution;
1.4 mixing:
mixing the three wall material solutions obtained in the steps 1,2 and 3 according to the volume ratio of 2.5:3.5:4.0 to prepare a wall material mixed solution;
2. preparing a core material:
2.1 Synthesis of 1,2,5, 6-O-selenium-D-glucosamine
Adding 5g of selenium into 30mL of acetic anhydride in a round-bottom flask, stirring and cooling to 0 ℃, adding 5.5g of glucosamine hydrochloride, slowly dropwise adding 2.5mL of concentrated sulfuric acid, stirring for 10 minutes at about 5 ℃, stirring overnight by using a magnetic stirrer when the temperature of the solution rises to 25 ℃ until the temperature is reduced to 0 ℃, continuously dropwise adding 20mL of absolute ethyl alcohol into the beaker, stirring for 3 hr while maintaining the temperature at 0 deg.C, vacuum filtering to obtain white solid, washing with ethyl acetate until no acid smell is obtained, about 5g of a white substance was obtained by vacuum drying at 25 ℃ for 10 hours, and further dissolved in 25mL of ultrapure water, adding 3.5g of sodium acetate under the action of a magnetic stirrer, obtaining precipitated white solid, continuing stirring until the sodium acetate is completely dissolved, extracting with ethyl acetate, and removing the solvent by concentration under reduced pressure to obtain the white solid: 1,2,5, 6-O-selenium-D-glucosamine.
2.2 Synthesis of (1,2,5, 6-O-Se) -D-Ganoderic acid glucose
Slowly adding 15mL of ganoderic acid aqueous solution (concentration is 1mol/L) dropwise with 1.0g of 1,2,5, 6-O-selenium-D-glucosamine and 5mL of ganoderic acid solution under nitrogen protection at room temperature, stirring for 3 hr, stopping stirring, distilling under reduced pressure to remove organic solvent, adding 50mL of ethyl acetate for dilution, and diluting with 20mL of 10% NaHCO3Washed 3 times and anhydrous MgSO is added4Drying overnight, distilling under reduced pressure the next day to remove organic solvent to obtain light yellow paste, separating by column chromatography (silica gel 400-500 mesh, mobile phase volume ratio of ethyl acetate: methanol 10:1) to obtain white solid, and crystallizing with ethanol to obtain white crystal- (1,2,5, 6-O-selenium) -D-ganoderic acid glucose.
The (1,2,5, 6-O-selenium) -D-ganoderic acid glucose structure is characterized in that:
m/z348[M+H]+,354[M+Na]+,258[M-CH3COO]+,229[M-2CH3COO]+, 152[M-3CH3COO]+；1HNMR(400MHz,DMSO-d8)δH,9.50(s,2H,NH2),6.82(d, J＝3.89Hz,1H,H-1),5.28(dd,J1＝8.64Hz,J2＝10.84Hz,1H,H-3),6.46(t,J＝9.74Hz, 1H,H-4),4.13-4.19(m,2H,H-6a,6b),3.27(dd,J1＝1.32Hz,J2＝11.00Hz,1H,H-5), 3.87(dd,J1＝3.40Hz,J2＝10.54Hz,1H,H-2),2.13,2.16,2.19,2.21(4s,12H,4Ac)； 13CNMR(100MHz,DMSO-d6)δC:165.5,164.9,169.2,170.5(4COAc),90.3(C-1), 92.9(C-5),91.3(C-3),89.9(C-4),69.7(C-6),59.6(C-2),21.3,21.1,20.9, 21.8(4CH3COO)。
3, preparing a rumen bypass coated ganoderic acid preparation:
firstly, filling a core material ((1,2,5, 6-O-selenium) -D-ganoderic acid glucose) into a coating chamber, then adjusting atomization pressure and air inlet temperature to enable the solidified mixture to be in a fluidized state and reach 50 ℃, and then spraying a mixed wall material solution on the core material through a spray gun of the coating chamber by a peristaltic pump to prepare a rumen-protected ganoderic acid product, wherein the volume ratio of the core material to the wall material mixed solution is 46: 54.
Example 2
The preparation method of rumen bypass envelope product containing (1,2,5, 6-O-selenium) -D-ganoderic acid glucose (glucosamine hydrochloride, weight ratio of selenium to ganoderic acid A is 3:3:4) comprises the following steps:
1. preparation of a coating film:
1.1 preparation of chitosan wall material solution:
preparing 900mL of 3.5% acetic acid solution; weighing 35g of chitosan, adding the chitosan into an acetic acid solution, stirring and dissolving the chitosan in water at 35 ℃ to prepare a wall material preparation solution;
1.2 preparation of palm oil wall material suspension:
weighing 35g of palm oil, adding 900m L90% alcohol solution, stirring to dissolve, and preparing into 3% palm oil suspension;
1.3 preparation of acrylic resin wall material solution:
weighing 35g of acrylic resin, adding 85% alcohol solution, stirring to dissolve the acrylic resin, and preparing acrylic resin solution;
1.4 mixing:
mixing the three wall material solutions obtained in the steps 1,2 and 3 according to the volume ratio of 2.5:3.5:4.0 to prepare a wall material mixed solution;
2. preparing a core material:
2.1 Synthesis of 1,2,5, 6-O-selenium-D-glucosamine
Adding 6g of selenium into 30mL of acetic anhydride in a round-bottom flask, stirring and cooling to 0 ℃, adding 6.6g of glucosamine hydrochloride, slowly dropwise adding 2.5mL of concentrated sulfuric acid, stirring for 10 minutes at about 5 ℃, stirring overnight by using a magnetic stirrer when the temperature of the solution rises to 25 ℃ until the temperature is reduced to 0 ℃, continuously dropwise adding 20mL of absolute ethyl alcohol into the beaker, stirring for 3 hr while maintaining the temperature at 0 deg.C, vacuum filtering to obtain white solid, washing with ethyl acetate until no acid smell is obtained, about 5g of a white substance was obtained by vacuum drying at 25 ℃ for 10 hours, and further dissolved in 25mL of ultrapure water, adding 3.5g of sodium acetate under the action of a magnetic stirrer, obtaining precipitated white solid, continuing stirring until the sodium acetate is completely dissolved, extracting with ethyl acetate, and removing the solvent by concentration under reduced pressure to obtain the white solid: 1,2,5, 6-O-selenium-D-glucosamine.
2.2 Synthesis of (1,2,5, 6-O-Se) -D-Ganoderic acid glucose
Slowly adding 12mL of ganoderic acid aqueous solution (concentration 1mol/L) under nitrogen protection, stirring for 3 hr, stopping stirring, distilling under reduced pressure to remove organic solvent, adding 50mL of ethyl acetate, diluting, and diluting with 20mL of 10% NaHCO3Washed 3 times and anhydrous MgSO is added4Drying overnight, distilling under reduced pressure the next day to remove organic solvent to obtain light yellow paste, separating by column chromatography (silica gel 400-500 mesh, mobile phase volume ratio of ethyl acetate: methanol 10:1) to obtain white solid, and crystallizing with ethanol to obtain white crystal- (1,2,5, 6-O-selenium) -D-ganoderic acid glucose.
The (1,2,5, 6-O-selenium) -D-ganoderic acid glucose structure is characterized in that:
m/z348[M+H]+,354[M+Na]+,268[M-CH3COO]+,221[M-2CH3COO]+, 149[M-3CH3COO]+；1HNMR(400MHz,DMSO-d8)δH,9.40(s,2H,NH2),6.79(d, J＝3.89Hz,1H,H-1),5.23(dd,J1＝8.64Hz,J2＝10.84Hz,1H,H-3),6.33(t,J＝9.74Hz, 1H,H-4),4.05-4.09(m,2H,H-6a,6b),3.31(dd,J1＝1.32Hz,J2＝11.00Hz,1H,H-5), 3.74(dd,J1＝3.40Hz,J2＝10.54Hz,1H,H-2),2.05,2.09,2.16,2.19(4s,12H,4Ac)； 13CNMR(100MHz,DMSO-d6)δC:164.9,165.4,168.3,169.3(4COAc),91.2(C-1), 92.6(C-5),90.4(C-3),89.4(C-4),60.2(C-6),59.2(C-2),21.5,21.6,20.8, 22.2(4CH3COO)。
3, preparing a rumen bypass coated ganoderic acid preparation:
firstly, filling a core material ((1,2,5, 6-O-selenium) -D-ganoderic acid glucose) into a coating chamber, then adjusting atomization pressure and air inlet temperature to enable the solidified mixture to be in a fluidized state and reach 50 ℃, and then spraying a mixed wall material solution on the core material through a spray gun of the coating chamber by a peristaltic pump to prepare a rumen-protected ganoderic acid product, wherein the volume ratio of the core material to the wall material mixed solution is 46: 54.
Test 1
The rumen bypass envelope product containing (1,2,5, 6-O-selenium) -D-ganoderic acid glucose obtained in the example was subjected to a potency evaluation test:
1. design of experiments
Selecting 60 healthy Holstein cows in the peak lactation period, randomly distributing 6 groups according to the principle that the number of lactation days (100 +/-10.9 days), the weight (649.7 +/-43.5 kg), the number of fetuses (2.52 +/-0.78 fetuses) and the milk yield (29.4 +/-6.18 kg) are similar, wherein the 6 groups are respectively a control group (basic daily ration +0.8g of ganoderic acid (the content of the ganoderic acid is consistent with that of the five formulas) and five ((1,2,5, 6-O-selenium) -D-ganoderic acid glucose) addition groups with different formulas (3.0 g/head/day of the (1,2,5, 6-O-selenium) -D-ganoderic acid glucose is added on the basic daily ration).
2. Sample collection analysis and test observation index
Daily ration for dairy cow
Basic daily ration is prepared according to standard milk cow feeding standard (NY/T34-2004) in agricultural industry of the people's republic of China. Alfalfa, oat grass and silage corn were the main roughage sources for the test diets, with the feed being based on 10% of the remainder.
The test period is 8 weeks, the milk yield is measured every week, basal diet is fed, and aminovale-selenium 1000 is not fed. And (3) measuring the production performance (milk yield) of the dairy cow, the breast glucose utilization efficiency (lactose and lactic acid content) and the stress index (MDA and ROS) in the milk in the pilot period.
Table 1: influence of rumen-protected ganoderic acid preparation with different formulations on milk cow mammary lactose content
Formula 1, glucosamine hydrochloride, selenium and ganoderic acid A ═ 1:1: 3
Formulation 2 (example 1) glucosamine hydrochloride, selenium and ganoderic acid a ═ 1:1:2
Formulation 3 (example 2) glucosamine hydrochloride, selenium and ganoderic acid a ═ 3:3:4
Formula 4, glucosamine hydrochloride, selenium and ganoderic acid a 3.5: 3.5: 3
Formula 5, glucosamine hydrochloride, selenium and ganoderic acid A ═ 4: 4: 2
The results show that under the conditions of example 1 and example 2, the milk yield and lactose synthesis amount of cows were highest in each group; on the contrary, the milk cow has the lowest lactic acid content under the conditions of the examples 1 and 2, which indicates that the glucose in the mammary gland of the milk cow can be directionally converted into the lactose more efficiently at the moment, so that the utilization efficiency of the glucose of the milk cow is improved. Meanwhile, from two oxidative stress indexes of MDA and ROS, under the conditions of the examples 1 and 2, the MDA and ROS content in milk are the lowest in each group, and the milk cow breast health can be well maintained under the feeding condition.
To summarize, example 1, glucosamine hydrochloride, selenium and ganoderic acid a ratio was 1:1:2 and example 2, i.e. glucosamine hydrochloride, selenium and ganoderic acid a ratio of 3:3:4, the maintenance effect of the ganoderic acid on the conversion efficiency of glucose in mammary gland and the health of mammary gland is superior to that of the common ganoderic acid.
Claims (3)
1. The rumen bypass envelope product containing (1,2,5, 6-O-selenium) -D-ganoderic acid glucose is characterized in that a core material formula comprises glucosamine hydrochloride, selenium and ganoderic acid A, wherein the weight ratio of the glucosamine hydrochloride, the selenium and the ganoderic acid A is 1:1:2 or 3:3: 4.
2. The method for preparing a rumen bypass envelope product containing (1,2,5, 6-O-selenium) -D-ganoderic acid glucose according to claim 1, comprising the steps of:
preparation of a coating film:
1.1 preparation of chitosan wall material solution:
preparing an acetic acid solution; weighing chitosan, adding the chitosan into an acetic acid solution, stirring and dissolving to prepare a wall material preparation solution;
1.2 preparation of palm oil wall material suspension:
weighing palm oil, adding the palm oil into an alcohol solution, stirring and dissolving to prepare palm oil suspension;
1.3 preparation of acrylic resin wall material solution:
weighing acrylic resin, adding the acrylic resin into an alcohol solution, stirring and dissolving to prepare an acrylic resin solution;
1.4 mixing:
mixing the three wall material solutions obtained in the steps 1.1, 1.2 and 1.3 in a volume ratio of 2.3-2.7:3.3-3.7:3.8-4.2 (mixing to prepare a wall material mixed solution;
preparing a core material:
2.1 Synthesis of 1,2,5, 6-O-selenium-D-glucosamine
Adding selenium into acetic anhydride, stirring and cooling to 0 ℃, adding glucosamine hydrochloride, slowly dropwise adding concentrated sulfuric acid, stirring overnight (about the phenomenon can not occur, uncertain characters can not appear), then slowly dropwise adding absolute ethyl alcohol, stirring at the temperature of 0 ℃ until white solid is separated out, performing suction filtration, washing the filtered white substance with ethyl acetate until no acid smell exists, performing vacuum drying to obtain a white substance, further dissolving the white substance in ultrapure water, adding sodium acetate while stirring to obtain separated white solid, continuing stirring until the sodium acetate is completely dissolved, extracting with ethyl acetate, and performing reduced pressure concentration to remove a solvent to obtain the white solid: 1,2,5, 6-O-selenium-D-glucosamine;
2.2 Synthesis of (1,2,5, 6-O-Se) -D-Ganoderic acid glucose
Slowly adding aqueous solution of ganoderic acid (commercially available) dropwise with 1,2,5, 6-O-selenium-D-glucosamine and ganoderic acid solution at room temperature under nitrogen protection, stirring, distilling under reduced pressure to remove organic solvent after reaction, adding ethyl acetate for dilution, and diluting with NaHCO3Washing with anhydrous MgSO4Drying, distilling under reduced pressure to remove organic solvent to obtain light yellow paste, separating by column chromatography to obtain white solid, and crystallizing with ethanol to obtain white crystal;
preparing a rumen bypass coated ganoderic acid preparation:
firstly, filling the core material (1,2,5, 6-O-selenium) -D-ganoderic acid glucose obtained in the step 2.2 into a coating chamber, then adjusting the atomization pressure and the air inlet temperature to enable the solidified mixture to be in a fluidized state and reach 50 ℃, and then spraying the mixed wall material solution on the core material through a spray gun of the coating chamber by a peristaltic pump to prepare the rumen-protected ganoderic acid product, wherein the volume ratio of the core material to the wall material mixed solution is 43-47: 53-57.
3. The method for preparing a rumen bypass envelope product containing (1,2,5, 6-O-selenium) -D-ganoderic acid glucose as claimed in claim 2, wherein the silica gel in column chromatography in step 2.2 is 400-500 mesh, and the volume ratio of ethyl acetate to methanol is 10: 1.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1611223A (en) * | 2003-10-27 | 2005-05-04 | 王浦林 | Sulfony lated acetylglucosamine medicinal composition and its use |
| CN101095689A (en) * | 2007-06-22 | 2008-01-02 | 彭秀兰 | Production process of glucosamine lysine selenium salt |
| CN102246912A (en) * | 2011-07-06 | 2011-11-23 | 浙江大学 | Rumen bypass GABA cow concentrate |
| CN109170251A (en) * | 2018-11-21 | 2019-01-11 | 河北农业大学 | A kind of rumen glucose microcapsules and preparation method thereof |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1611223A (en) * | 2003-10-27 | 2005-05-04 | 王浦林 | Sulfony lated acetylglucosamine medicinal composition and its use |
| CN101095689A (en) * | 2007-06-22 | 2008-01-02 | 彭秀兰 | Production process of glucosamine lysine selenium salt |
| CN102246912A (en) * | 2011-07-06 | 2011-11-23 | 浙江大学 | Rumen bypass GABA cow concentrate |
| CN109170251A (en) * | 2018-11-21 | 2019-01-11 | 河北农业大学 | A kind of rumen glucose microcapsules and preparation method thereof |
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