CN112458129B - Preparation process of short-chain ganoderan sulfuric acid derivative - Google Patents
Preparation process of short-chain ganoderan sulfuric acid derivative Download PDFInfo
- Publication number
- CN112458129B CN112458129B CN202011590143.4A CN202011590143A CN112458129B CN 112458129 B CN112458129 B CN 112458129B CN 202011590143 A CN202011590143 A CN 202011590143A CN 112458129 B CN112458129 B CN 112458129B
- Authority
- CN
- China
- Prior art keywords
- ganoderma lucidum
- chain
- short
- polysaccharide
- ganoderan
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 150000003467 sulfuric acid derivatives Chemical class 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 240000008397 Ganoderma lucidum Species 0.000 claims abstract description 143
- 235000001637 Ganoderma lucidum Nutrition 0.000 claims abstract description 143
- 229920001282 polysaccharide Polymers 0.000 claims abstract description 107
- 239000005017 polysaccharide Substances 0.000 claims abstract description 107
- 150000004676 glycans Chemical class 0.000 claims abstract description 104
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 66
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 21
- 241000222336 Ganoderma Species 0.000 claims abstract description 18
- 238000001212 derivatisation Methods 0.000 claims abstract description 13
- 238000000855 fermentation Methods 0.000 claims description 74
- 230000004151 fermentation Effects 0.000 claims description 74
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 37
- 238000004108 freeze drying Methods 0.000 claims description 28
- 238000001556 precipitation Methods 0.000 claims description 19
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000008213 purified water Substances 0.000 claims description 18
- 238000005406 washing Methods 0.000 claims description 18
- 238000000605 extraction Methods 0.000 claims description 13
- 239000000047 product Substances 0.000 claims description 13
- 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 claims description 9
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000002518 antifoaming agent Substances 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 9
- 239000008103 glucose Substances 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- 238000011081 inoculation Methods 0.000 claims description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 9
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 9
- 229910000402 monopotassium phosphate Inorganic materials 0.000 claims description 9
- 235000019796 monopotassium phosphate Nutrition 0.000 claims description 9
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 claims description 9
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 9
- 239000000843 powder Substances 0.000 claims description 9
- 230000001376 precipitating effect Effects 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- 239000006228 supernatant Substances 0.000 claims description 9
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 108010059892 Cellulase Proteins 0.000 claims description 5
- 229940106157 cellulase Drugs 0.000 claims description 5
- 244000144972 livestock Species 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 238000009304 pastoral farming Methods 0.000 claims 1
- 238000009374 poultry farming Methods 0.000 claims 1
- 230000004071 biological effect Effects 0.000 abstract description 6
- 244000144977 poultry Species 0.000 abstract description 6
- 210000004185 liver Anatomy 0.000 abstract description 5
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 4
- 230000002155 anti-virotic effect Effects 0.000 abstract description 3
- 230000003832 immune regulation Effects 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- -1 polysaccharide sulfuric acid derivative Chemical class 0.000 abstract description 3
- 238000005728 strengthening Methods 0.000 abstract description 3
- 239000001963 growth medium Substances 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 8
- 238000000502 dialysis Methods 0.000 description 7
- 241000287828 Gallus gallus Species 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 229920002307 Dextran Polymers 0.000 description 5
- OQUKIQWCVTZJAF-UHFFFAOYSA-N phenol;sulfuric acid Chemical compound OS(O)(=O)=O.OC1=CC=CC=C1 OQUKIQWCVTZJAF-UHFFFAOYSA-N 0.000 description 5
- 235000013594 poultry meat Nutrition 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 4
- 238000009395 breeding Methods 0.000 description 4
- 230000001488 breeding effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 3
- 229910001626 barium chloride Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 230000001937 non-anti-biotic effect Effects 0.000 description 2
- 210000000952 spleen Anatomy 0.000 description 2
- 210000001541 thymus gland Anatomy 0.000 description 2
- 238000012795 verification Methods 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000002929 anti-fatigue Effects 0.000 description 1
- 230000003471 anti-radiation Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000007365 immunoregulation Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/04—Polysaccharides, i.e. compounds containing more than five saccharide radicals attached to each other by glycosidic bonds
-
- 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
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/70—Feeding-stuffs specially adapted for particular animals for birds
- A23K50/75—Feeding-stuffs specially adapted for particular animals for birds for poultry
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Food Science & Technology (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Animal Husbandry (AREA)
- Birds (AREA)
- Microbiology (AREA)
- Genetics & Genomics (AREA)
- General Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Materials Engineering (AREA)
- Medicinal Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Abstract
The invention discloses a preparation process of a short-chain ganoderan sulfuric acid derivative, which comprises the steps of fermenting ganoderma lucidum mycelia to obtain a large amount of ganoderma lucidum mycelia; extracting Ganoderma polysaccharide, purifying, and lyophilizing; performing short-chain treatment on ganoderma lucidum polysaccharide; and performing sulfuric acid derivatization on the short-chain ganoderma lucidum polysaccharide. The process of the invention takes ganoderma lucidum polysaccharide as a material, transforms the original ganoderma lucidum polysaccharide into short-chain ganoderma lucidum polysaccharide sulfuric acid derivative, is easier to dissolve in water, has more biological activity, improves the antivirus and anti-inflammatory capability of poultry compared with the common ganoderma lucidum polysaccharide, simultaneously plays the roles of strengthening immune regulation, protecting liver and the like, and has greatly improved efficacy.
Description
Technical Field
The invention relates to the technical field of ganoderma lucidum polysaccharide, in particular to a preparation process of a short-chain ganoderma lucidum polysaccharide sulfuric acid derivative.
Background
Ganoderan is one of main effective components of Ganoderma mycelia, and has biological activities of antivirus, antiinflammatory, antitumor, antioxidant, immunoregulation, antiradiation, liver protection, antifatigue, etc.
The molecular size and chain conformation of some ganoderma lucidum polysaccharides with lower activity are changed by a derivatization method, so that the water solubility and the biological activity of the ganoderma lucidum polysaccharides are improved. After the polysaccharide is modified, the spatial structure, molecular weight, substituent group type, number, position and the like of the polysaccharide are possibly changed, and the factors influence the physicochemical property and the biological activity of the polysaccharide.
In addition, the non-antibiotic breeding becomes a trend in the breeding of livestock and poultry, so that the non-antibiotic medicines become more and more urgent, the diseases of animals become more and more complicated, and the prevention and treatment of improving the antioxidant capacity of the animals, protecting the livers of the animals and diminishing inflammation are the key points of most of the breeding of livestock and poultry.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a preparation process of a short-chain ganoderan sulfuric acid derivative, which takes ganoderan as a material, transforms the original ganoderan into the short-chain ganoderan sulfuric acid derivative, is more soluble in water and has biological activity, improves the antiviral and anti-inflammatory capabilities of poultry compared with the common ganoderan, plays the roles of strengthening immune regulation, protecting liver and the like, and has greatly improved efficacy.
In order to achieve the purpose, the invention provides the following technical scheme:
a preparation process of short-chain ganoderan sulfuric acid derivatives comprises the following steps:
(1) fermenting to obtain a large amount of ganoderma lucidum mycelia: placing Ganoderma mycelia in fermentation medium for fermentation, wherein the inoculation amount of Ganoderma mycelia is 10%, the fermentation temperature is 29 deg.C, stirring speed is 150rpm/min, initial fermentation pH is 5.7, tank pressure is 0.05Mpa, and fermentation period is 4.5 days; after fermentation is finished, centrifuging the ganoderma lucidum fermentation liquor obtained by fermentation to collect mycelia, washing with purified water, centrifuging again, washing with purified water once, and finally centrifuging to collect ganoderma lucidum mycelia;
(2) extracting, purifying and freeze-drying ganoderma lucidum polysaccharide: adding water into Ganoderma mycelia at a ratio of 1:12, heating to extract ganoderan at 93-96 deg.C for 1-2 hr; after extraction, cooling the temperature to room temperature, and centrifuging to collect supernatant; precipitating ganoderan with ethanol for three times, and lyophilizing to obtain crude ganoderan;
(3) short-chain treatment of ganoderan: dissolving the ganoderma lucidum crude polysaccharide obtained in the step (2) in water according to the ratio of 1g of ganoderma lucidum crude polysaccharide to 40mL of water, adjusting the pH value of a reaction solution to 7, adding 1% by mass of cellulase, reacting for 4 hours at 35 ℃, and after the reaction is finished, carrying out alcohol precipitation and freeze drying on the ganoderma lucidum polysaccharide to obtain short-chain ganoderma lucidum polysaccharide;
(4) sulfuric acid derivatization: and (3) carrying out short-chain ganoderma lucidum polysaccharide treatment on the short-chain ganoderma lucidum polysaccharide obtained in the step (3) according to the following steps of: sulfamic acid: the ganoderma lucidum polysaccharide is 500: 15: 1, reacting at 55-65 ℃ for 3.5-4.5h, dialyzing the product for 24 hours, collecting the dialyzate, and performing alcohol precipitation, redissolution and freeze-drying on the dialyzate to obtain the short-chain ganoderan sulfuric acid derivative.
Further, the fermentation medium in the step (1) has the following composition: 3% of glucose, 1% of yeast powder, 0.4% of monopotassium phosphate, 0.4% of magnesium sulfate, 0.2% of defoaming agent and the balance of water.
Further, the extraction temperature in the step (2) was 95 ℃.
Further, the extraction time in the step (2) was 1.5 hours.
Further, the step (3) of short-chain treatment of ganoderma lucidum polysaccharide: and (3) dissolving the ganoderma lucidum crude polysaccharide obtained in the step (2) in water according to the ratio of 1g of ganoderma lucidum crude polysaccharide to 40mL of water, adding hydrochloric acid to adjust the pH value to 2, reacting for 4 hours at 80 ℃, and after the reaction is finished, carrying out alcohol precipitation and freeze drying on the ganoderma lucidum polysaccharide to obtain the short-chain ganoderma lucidum polysaccharide.
Further, the step (3) of short-chain treatment of ganoderma lucidum polysaccharide: and (3) dissolving the ganoderma lucidum crude polysaccharide obtained in the step (2) in water according to the ratio of 1g of ganoderma lucidum crude polysaccharide to 40mL of water, adding sodium hydroxide to adjust the pH value to 13, reacting for 4 hours at 80 ℃, and after the reaction is finished, carrying out alcohol precipitation and freeze drying on the ganoderma lucidum polysaccharide to obtain the short-chain ganoderma lucidum polysaccharide.
Further, step (4) was reacted at 60 ℃ for 4 hours.
The invention also provides the application of the short-chain ganoderan sulfuric acid derivative as an antibiotic-free product in livestock and poultry breeding.
The invention has the beneficial effects that:
(1) the invention takes ganoderma lucidum polysaccharide as a material, combines the short-chain technology and the sulfation technology, transforms the original ganoderma lucidum polysaccharide into the short-chain ganoderma lucidum polysaccharide sulfate derivative, is easier to dissolve in water, has more biological activity, improves the antivirus and anti-inflammatory capability of poultry compared with the common ganoderma lucidum polysaccharide, simultaneously plays the roles of strengthening immune regulation, protecting liver and the like, and has greatly improved efficacy.
(2) The invention strengthens the preparation process of sulfuric acid derivatization of the ganoderma lucidum polysaccharide, namely the sulfated derivative of the ganoderma lucidum polysaccharide with short chain, not only does not increase complicated production steps, but also ensures that the obtained product has better effect, and simultaneously, compared with the common ganoderma lucidum polysaccharide and the derivative of the ganoderma lucidum polysaccharide, the sulfated derivative of the ganoderma lucidum polysaccharide is more soluble in water, so that the product is easier to operate in the using process.
Drawings
FIG. 1 is a curve fitted to the total sugar content of short-chained ganoderan obtained in example 3 of the present invention;
FIG. 2 is a curve fitted to the total sugar content of short-chained ganoderan obtained in example 4 of the present invention;
FIG. 3 is a curve fitted to the total sugar content of short-chained ganoderan obtained in example 5 of the present invention;
FIG. 4 shows a curve fitted to the total sugar content of ganoderan obtained in comparative example 1 of the present invention;
FIG. 5 shows a curve fitted to the total sugar content of ganoderan obtained in comparative example 2 of the present invention.
Detailed Description
The present invention will be further described with reference to the following examples. The following examples will assist those skilled in the art in further understanding the invention, but are not intended to limit the invention in any way. It should be noted that variations and modifications can be made by persons skilled in the art without departing from the spirit of the invention. All falling within the scope of the present invention.
Embodiment 1 a process for preparing a short-chain sulfated ganoderan, comprising the steps of:
(1) fermenting to obtain a large amount of ganoderma lucidum mycelia: putting the ganoderma lucidum mycelia into a fermentation culture medium for fermentation, wherein the culture medium comprises the following components: 3% of glucose, 1% of yeast powder, 0.4% of monopotassium phosphate, 0.4% of magnesium sulfate, 0.2% of defoaming agent and the balance of water; the inoculation amount of the ganoderma lucidum mycelia is 10%, the fermentation temperature is 29 ℃, the stirring speed is 150rpm/min, the initial fermentation pH is 5.7, the tank pressure is 0.05Mpa, and the fermentation period is 4.5 days; after fermentation is finished, centrifuging the ganoderma lucidum fermentation liquor obtained by fermentation to collect mycelia, washing with purified water, centrifuging again, washing with purified water once, and finally centrifuging to collect ganoderma lucidum mycelia;
(2) extracting, purifying and freeze-drying ganoderma lucidum polysaccharide: adding water into Ganoderma mycelia at a ratio of 1:12, heating to extract ganoderan at 96 deg.C for 2 hr; after extraction, cooling the temperature to room temperature, and centrifuging to collect supernatant; precipitating ganoderan with ethanol for three times, and lyophilizing to obtain crude ganoderan;
(3) short-chain treatment of ganoderan: dissolving the ganoderma lucidum crude polysaccharide obtained in the step (2) in water according to the ratio of 1g of ganoderma lucidum crude polysaccharide to 40mL of water, adjusting the pH value of a reaction solution to 7, adding 1% by mass of cellulase, reacting for 4 hours at 35 ℃, and after the reaction is finished, carrying out alcohol precipitation and freeze drying on the ganoderma lucidum polysaccharide to obtain short-chain ganoderma lucidum polysaccharide;
(4) sulfuric acid derivatization: and (3) carrying out short-chain ganoderma lucidum polysaccharide treatment on the short-chain ganoderma lucidum polysaccharide obtained in the step (3) according to the following steps of: sulfamic acid: the ganoderma lucidum polysaccharide is 500: 15: 1, reacting at 65 ℃ for 4.5h, dialyzing the product for 24 h, collecting the dialysate, and performing alcohol precipitation, redissolution and freeze-drying on the dialysate to obtain the short-chain ganoderan sulfuric acid derivative.
Embodiment 2 a process for preparing a short-chain sulfated ganoderan, comprising the steps of:
(1) fermenting to obtain a large amount of ganoderma lucidum mycelia: putting the ganoderma lucidum mycelia into a fermentation culture medium for fermentation, wherein the culture medium comprises the following components: 3% of glucose, 1% of yeast powder, 0.4% of monopotassium phosphate, 0.4% of magnesium sulfate, 0.2% of defoaming agent and the balance of water; the inoculation amount of the ganoderma lucidum mycelia is 10%, the fermentation temperature is 29 ℃, the stirring speed is 150rpm/min, the initial fermentation pH is 5.7, the tank pressure is 0.05Mpa, and the fermentation period is 4.5 days; after fermentation is finished, centrifuging the ganoderma lucidum fermentation liquor obtained by fermentation to collect mycelia, washing with purified water, centrifuging again, washing with purified water once, and finally centrifuging to collect ganoderma lucidum mycelia;
(2) extracting, purifying and freeze-drying ganoderma lucidum polysaccharide: adding water into Ganoderma mycelia at a ratio of 1:12, heating to extract ganoderan at 93 deg.C for 1 hr; after extraction, cooling the temperature to room temperature, and centrifuging to collect supernatant; precipitating ganoderan with ethanol for three times, and lyophilizing to obtain crude ganoderan;
(3) short-chain treatment of ganoderan: dissolving the ganoderma lucidum crude polysaccharide obtained in the step (2) in water according to the ratio of 1g of ganoderma lucidum crude polysaccharide to 40mL of water, adjusting the pH value of a reaction solution to 7, adding 1% by mass of cellulase, reacting for 4 hours at 35 ℃, and after the reaction is finished, carrying out alcohol precipitation and freeze drying on the ganoderma lucidum polysaccharide to obtain short-chain ganoderma lucidum polysaccharide;
(4) sulfuric acid derivatization: and (3) carrying out short-chain ganoderma lucidum polysaccharide treatment on the short-chain ganoderma lucidum polysaccharide obtained in the step (3) according to the following steps of: sulfamic acid: the ganoderma lucidum polysaccharide is 500: 15: 1, reacting at 55 ℃ for 3.5h, dialyzing the product for 24 h, collecting the dialysate, and performing alcohol precipitation, redissolution and freeze-drying on the dialysate to obtain the short-chain ganoderan sulfuric acid derivative.
Embodiment 3 a process for preparing a short-chain sulfated ganoderan, comprising the steps of:
(1) fermenting to obtain a large amount of ganoderma lucidum mycelia: putting the ganoderma lucidum mycelia into a fermentation culture medium for fermentation, wherein the culture medium comprises the following components: 3% of glucose, 1% of yeast powder, 0.4% of monopotassium phosphate, 0.4% of magnesium sulfate, 0.2% of defoaming agent and the balance of water; the inoculation amount of the ganoderma lucidum mycelia is 10%, the fermentation temperature is 29 ℃, the stirring speed is 150rpm/min, the initial fermentation pH is 5.7, the tank pressure is 0.05Mpa, and the fermentation period is 4.5 days; after fermentation is finished, centrifuging the ganoderma lucidum fermentation liquor obtained by fermentation to collect mycelia, washing with purified water, centrifuging again, washing with purified water once, and finally centrifuging to collect ganoderma lucidum mycelia;
(2) extracting, purifying and freeze-drying ganoderma lucidum polysaccharide: adding water into Ganoderma mycelia at a ratio of 1:12, heating to extract ganoderan at 95 deg.C for 1.5 hr; after extraction, cooling the temperature to room temperature, and centrifuging to collect supernatant; precipitating ganoderan with ethanol for three times, and lyophilizing to obtain crude ganoderan;
(3) short-chain treatment of ganoderan: dissolving the ganoderma lucidum crude polysaccharide obtained in the step (2) in water according to the ratio of 1g of ganoderma lucidum crude polysaccharide to 40mL of water, adjusting the pH value of a reaction solution to 7, adding 1% by mass of cellulase, reacting for 4 hours at 35 ℃, and after the reaction is finished, carrying out alcohol precipitation and freeze drying on the ganoderma lucidum polysaccharide to obtain short-chain ganoderma lucidum polysaccharide;
passing the short-chain Ganoderma polysaccharide through dextran G200 gel column, and measuring total sugar content by sulfuric acid-phenol method to fit curve, as shown in FIG. 1.
(4) Sulfuric acid derivatization: and (3) carrying out short-chain ganoderma lucidum polysaccharide treatment on the short-chain ganoderma lucidum polysaccharide obtained in the step (3) according to the following steps of: sulfamic acid: the ganoderma lucidum polysaccharide is 500: 15: 1, reacting at 60 ℃ for 4 hours, dialyzing the product for 24 hours, collecting the dialysate, and performing alcohol precipitation, redissolution and freeze-drying on the dialysate to obtain the short-chain ganoderan sulfuric acid derivative.
Embodiment 4 a process for preparing a short-chain sulfated ganoderan, comprising the steps of:
(1) fermenting to obtain a large amount of ganoderma lucidum mycelia: putting the ganoderma lucidum mycelia into a fermentation culture medium for fermentation, wherein the culture medium comprises the following components: 3% of glucose, 1% of yeast powder, 0.4% of monopotassium phosphate, 0.4% of magnesium sulfate, 0.2% of defoaming agent and the balance of water; the inoculation amount of the ganoderma lucidum mycelia is 10%, the fermentation temperature is 29 ℃, the stirring speed is 150rpm/min, the initial fermentation pH is 5.7, the tank pressure is 0.05Mpa, and the fermentation period is 4.5 days; after fermentation is finished, centrifuging the ganoderma lucidum fermentation liquor obtained by fermentation to collect mycelia, washing with purified water, centrifuging again, washing with purified water once, and finally centrifuging to collect ganoderma lucidum mycelia;
(2) extracting, purifying and freeze-drying ganoderma lucidum polysaccharide: adding water into Ganoderma mycelia at a ratio of 1:12, heating to extract ganoderan at 95 deg.C for 1.5 hr; after extraction, cooling the temperature to room temperature, and centrifuging to collect supernatant; precipitating ganoderan with ethanol for three times, and lyophilizing to obtain crude ganoderan;
(3) short-chain treatment of ganoderan: and (3) dissolving the ganoderma lucidum crude polysaccharide obtained in the step (2) in water according to the ratio of 1g of ganoderma lucidum crude polysaccharide to 40mL of water, adding hydrochloric acid to adjust the pH value to 2, reacting for 4 hours at 80 ℃, and after the reaction is finished, carrying out alcohol precipitation and freeze drying on the ganoderma lucidum polysaccharide to obtain the short-chain ganoderma lucidum polysaccharide.
Passing the short-chain Ganoderma polysaccharide through dextran G200 gel column, and measuring total sugar content by sulfuric acid-phenol method to fit curve, as shown in FIG. 2.
(4) Sulfuric acid derivatization: and (3) carrying out short-chain ganoderma lucidum polysaccharide treatment on the short-chain ganoderma lucidum polysaccharide obtained in the step (3) according to the following steps of: sulfamic acid: the ganoderma lucidum polysaccharide is 500: 15: 1, reacting at 60 ℃ for 4 hours, dialyzing the product for 24 hours, collecting the dialysate, and performing alcohol precipitation, redissolution and freeze-drying on the dialysate to obtain the short-chain ganoderan sulfuric acid derivative.
Embodiment 5 a process for preparing a short-chain sulfated ganoderan, comprising the steps of:
(1) fermenting to obtain a large amount of ganoderma lucidum mycelia: putting the ganoderma lucidum mycelia into a fermentation culture medium for fermentation, wherein the culture medium comprises the following components: 3% of glucose, 1% of yeast powder, 0.4% of monopotassium phosphate, 0.4% of magnesium sulfate, 0.2% of defoaming agent and the balance of water; the inoculation amount of the ganoderma lucidum mycelia is 10%, the fermentation temperature is 29 ℃, the stirring speed is 150rpm/min, the initial fermentation pH is 5.7, the tank pressure is 0.05Mpa, and the fermentation period is 4.5 days; after fermentation is finished, centrifuging the ganoderma lucidum fermentation liquor obtained by fermentation to collect mycelia, washing with purified water, centrifuging again, washing with purified water once, and finally centrifuging to collect ganoderma lucidum mycelia;
(2) extracting, purifying and freeze-drying ganoderma lucidum polysaccharide: adding water into Ganoderma mycelia at a ratio of 1:12, heating to extract ganoderan at 95 deg.C for 1.5 hr; after extraction, cooling the temperature to room temperature, and centrifuging to collect supernatant; precipitating ganoderan with ethanol for three times, and lyophilizing to obtain crude ganoderan;
(3) short-chain treatment of ganoderan: and (3) dissolving the ganoderma lucidum crude polysaccharide obtained in the step (2) in water according to the ratio of 1g of ganoderma lucidum crude polysaccharide to 40mL of water, adding sodium hydroxide to adjust the pH value to 13, reacting for 4 hours at 80 ℃, and after the reaction is finished, carrying out alcohol precipitation and freeze drying on the ganoderma lucidum polysaccharide to obtain the short-chain ganoderma lucidum polysaccharide.
Passing the short-chain Ganoderma polysaccharide through dextran G200 gel column, and measuring total sugar content by sulfuric acid-phenol method to fit curve, as shown in FIG. 3.
(4) Sulfuric acid derivatization: and (3) carrying out short-chain ganoderma lucidum polysaccharide treatment on the short-chain ganoderma lucidum polysaccharide obtained in the step (3) according to the following steps of: sulfamic acid: the ganoderma lucidum polysaccharide is 500: 15: 1, reacting at 60 ℃ for 4 hours, dialyzing the product for 24 hours, collecting the dialysate, and performing alcohol precipitation, redissolution and freeze-drying on the dialysate to obtain the short-chain ganoderan sulfuric acid derivative.
Comparative example 1 a process for preparing a sulfated derivative of ganoderan comprising the steps of:
(1) fermenting to obtain a large amount of ganoderma lucidum mycelia: putting the ganoderma lucidum mycelia into a fermentation culture medium for fermentation, wherein the culture medium comprises the following components: 3% of glucose, 1% of yeast powder, 0.4% of monopotassium phosphate, 0.4% of magnesium sulfate, 0.2% of defoaming agent and the balance of water; the inoculation amount of the ganoderma lucidum mycelia is 10%, the fermentation temperature is 29 ℃, the stirring speed is 150rpm/min, the initial fermentation pH is 5.7, the tank pressure is 0.05Mpa, and the fermentation period is 4.5 days; after fermentation is finished, centrifuging the ganoderma lucidum fermentation liquor obtained by fermentation to collect mycelia, washing with purified water, centrifuging again, washing with purified water once, and finally centrifuging to collect ganoderma lucidum mycelia;
(2) extracting, purifying and freeze-drying ganoderma lucidum polysaccharide: adding water into Ganoderma mycelia at a ratio of 1:12, heating to extract ganoderan at 95 deg.C for 1.5 hr; after extraction, cooling the temperature to room temperature, and centrifuging to collect supernatant; precipitating ganoderan with ethanol for three times, and lyophilizing to obtain crude ganoderan;
passing the ganoderan through dextran G200 gel column, and measuring total sugar content by sulfuric acid-phenol method to fit curve, as shown in FIG. 4.
(3) Sulfuric acid derivatization: and (3) performing treatment on the ganoderma lucidum crude polysaccharide obtained in the step (2) according to the following steps of: sulfamic acid: the ganoderma lucidum polysaccharide is 500: 15: 1, reacting at 60 ℃ for 4 hours, dialyzing the product for 24 hours, collecting the dialysate, and performing alcohol precipitation, redissolution and freeze-drying on the dialysate to obtain the ganoderan sulfuric acid derivative.
Comparative example 2 a process for preparing ganoderan, comprising the steps of:
(1) fermenting to obtain a large amount of ganoderma lucidum mycelia: putting the ganoderma lucidum mycelia into a fermentation culture medium for fermentation, wherein the culture medium comprises the following components: 3% of glucose, 1% of yeast powder, 0.4% of monopotassium phosphate, 0.4% of magnesium sulfate, 0.2% of defoaming agent and the balance of water; the inoculation amount of the ganoderma lucidum mycelia is 10%, the fermentation temperature is 29 ℃, the stirring speed is 150rpm/min, the initial fermentation pH is 5.7, the tank pressure is 0.05Mpa, and the fermentation period is 4.5 days; after fermentation is finished, centrifuging the ganoderma lucidum fermentation liquor obtained by fermentation to collect mycelia, washing with purified water, centrifuging again, washing with purified water once, and finally centrifuging to collect ganoderma lucidum mycelia;
(2) extracting, purifying and freeze-drying ganoderma lucidum polysaccharide: adding water into Ganoderma mycelia at a ratio of 1:12, heating to extract ganoderan at 95 deg.C for 1.5 hr; after extraction, cooling the temperature to room temperature, and centrifuging to collect supernatant; precipitating ganoderan with ethanol for three times, and lyophilizing to obtain crude ganoderan;
passing the ganoderan through dextran G200 gel column, and measuring total sugar content by sulfuric acid-phenol method to fit curve, as shown in FIG. 5.
Experimental examples related to Experimental study
1. Short-chain verification:
A. as can be seen from FIGS. 1 to 5, the G200 outflow peak images of the ganoderan obtained in examples 3 to 5 are significantly shifted to the right and have smaller molecular weights than those of comparative example 1 and comparative example 2, and it can be determined that the three methods for shortening provided in examples 3 to 5 of the present invention are effective.
2. And (3) sulfuric acid derivatization verification:
0.1g of the product obtained in example 3-example 5 and comparative example 1-comparative example 2 was dissolved in 5mL of water and dialyzed for 48 hours, and the water outside the dialysis bag was changed every 8 hours. 2ml of each solution inside and outside the dialysis bag is taken, 2ml of 1mol/L barium chloride solution is added, the mixture is shaken and mixed evenly, and then the absorbance light value at 360nm is measured by taking water as a reference. The measurement results are shown in table 1:
TABLE 1
| Example 3 | Example 4 | Example 5 | Comparative example 1 | Comparative example 2 | |
| Dialysis bag | 0.3567 | 0.3426 | 0.3215 | 0.3357 | 0.0072 |
| Outside the dialysis bag | 0.0057 | 0.0090 | 0.0032 | 0.0055 | 0.0084 |
As can be seen from Table 1, in examples 3 to 5 and comparative example 1, the solution inside the dialysis bag was significantly precipitated after the addition of barium chloride, while the solution outside the dialysis bag was not significantly reacted after the addition of barium chloride; no precipitate was generated inside and outside the dialysis bag in comparative example 2, and it can be judged that the derivatization with sulfuric acid was successful.
3. Animal experiments (resistance to oxidation):
selecting newly hatched broilers for experimental animals, feeding the broilers about 7 days old, averagely dividing the broilers into A, B, C, D, E groups, and feeding corresponding ganoderma lucidum polysaccharide freeze-dried substances to each group; the specific grouping is shown in table 2:
TABLE 2
Specifically, the method comprises the following steps: feeding 7 broilers per group according to the above different groups to corresponding lyophilized ganoderan with an addition of 0.5%. Feeding for three days, injecting 0.3ml of escherichia coli into each chicken to sicken the broiler chickens, feeding corresponding ganoderma lucidum polysaccharide freeze-dried substances all the time during the period, feeding for about 20 days all the time, and finally respectively taking the ratio of the weight of spleen and thymus gland organs to the weight of animals and SOD and GSH values as indexes to prove the antioxidant effect of different ganoderma lucidum polysaccharide freeze-dried substances. The results are shown in tables 3 and 4
TABLE 3 ratio of spleen to thymus organ weight to animal body weight
| Grouping | Group A | Group B | Group C | Group D | Group E |
| Size of ratio/%) | 0.77 | 0.88 | 0.82 | 0.37 | 0.23 |
TABLE 4 measured values of SOD and GSH values as indicators
| Grouping | Group A | Group B | Group C | Group D | Group E |
| SOD(U/mg) | 18.6 | 19.3 | 17.7 | 11.7 | 10.5 |
| GSH(ng/mg) | 105.6 | 111.2 | 94.3 | 73.4 | 78.2 |
As can be seen from the data in tables 3 and 4, the indexes of group A, B, C are better than those of group D, E, which shows that the three short-chain ganoderan derivatives of examples 3-5 of the present invention all have antioxidant effect and better effect than normal ganoderan and ganoderan derivatives. The effects of an enzymatic method and an acid method are particularly excellent, wherein the acid method is low in cost, but the reaction process needs to be accurately controlled; the enzyme method has relatively high cost, but the reaction process is mild and easy to control.
It should be noted that the specific embodiments are merely representative examples of the present invention, and it is obvious that the technical solution of the present invention is not limited to the above-mentioned examples, and many variations are possible. Those skilled in the art, having the benefit of this disclosure and the benefit of this written description, will appreciate that other embodiments can be devised which do not depart from the specific details disclosed herein.
Claims (8)
1. A preparation process of a short-chain ganoderan sulfuric acid derivative is characterized by comprising the following steps:
(1) fermenting to obtain a large amount of ganoderma lucidum mycelia: placing Ganoderma mycelia in fermentation medium for fermentation, wherein the inoculation amount of Ganoderma mycelia is 10%, the fermentation temperature is 29 deg.C, stirring speed is 150rpm/min, initial fermentation pH is 5.7, tank pressure is 0.05Mpa, and fermentation period is 4.5 days; after fermentation is finished, centrifuging the ganoderma lucidum fermentation liquor obtained by fermentation to collect mycelia, washing with purified water, centrifuging again, washing with purified water once, and finally centrifuging to collect ganoderma lucidum mycelia;
(2) extracting, purifying and freeze-drying ganoderma lucidum polysaccharide: adding water into Ganoderma mycelia at a ratio of 1:12, heating to extract ganoderan at 93-96 deg.C for 1-2 hr; after extraction, cooling the temperature to room temperature, and centrifuging to collect supernatant; precipitating ganoderan with ethanol for three times, and lyophilizing to obtain crude ganoderan;
(3) short-chain treatment of ganoderan: dissolving the ganoderma lucidum crude polysaccharide obtained in the step (2) in water according to the ratio of 1g of ganoderma lucidum crude polysaccharide to 40mL of water, adjusting the pH value of a reaction solution to 7, adding 1% by mass of cellulase, reacting for 4 hours at 35 ℃, and after the reaction is finished, carrying out alcohol precipitation and freeze drying on the ganoderma lucidum polysaccharide to obtain short-chain ganoderma lucidum polysaccharide;
(4) sulfuric acid derivatization: and (3) carrying out short-chain ganoderma lucidum polysaccharide treatment on the short-chain ganoderma lucidum polysaccharide obtained in the step (3) according to the following steps of: sulfamic acid: the ganoderma lucidum polysaccharide is 500: 15: 1, reacting at 55-65 ℃ for 3.5-4.5h, dialyzing the product for 24 hours, collecting the dialyzate, and performing alcohol precipitation, redissolution and freeze-drying on the dialyzate to obtain the short-chain ganoderan sulfuric acid derivative.
2. The process according to claim 1, wherein the fermentation medium of step (1) has a composition of: 3% of glucose, 1% of yeast powder, 0.4% of monopotassium phosphate, 0.4% of magnesium sulfate, 0.2% of defoaming agent and the balance of water.
3. The process of claim 1, wherein the extraction temperature in step (2) is 95 ℃.
4. The process of claim 1, wherein the extraction time in step (2) is 1.5 hours.
5. The process according to claim 1, wherein the step (3) of short-chain-treating the ganoderan: and (3) dissolving the ganoderma lucidum crude polysaccharide obtained in the step (2) in water according to the ratio of 1g of ganoderma lucidum crude polysaccharide to 40mL of water, adding hydrochloric acid to adjust the pH value to 2, reacting for 4 hours at 80 ℃, and after the reaction is finished, carrying out alcohol precipitation and freeze drying on the ganoderma lucidum polysaccharide to obtain the short-chain ganoderma lucidum polysaccharide.
6. The process according to claim 1, wherein the step (3) of short-chain-treating the ganoderan: and (3) dissolving the ganoderma lucidum crude polysaccharide obtained in the step (2) in water according to the ratio of 1g of ganoderma lucidum crude polysaccharide to 40mL of water, adding sodium hydroxide to adjust the pH value to 13, reacting for 4 hours at 80 ℃, and after the reaction is finished, carrying out alcohol precipitation and freeze drying on the ganoderma lucidum polysaccharide to obtain the short-chain ganoderma lucidum polysaccharide.
7. The process according to claim 1, wherein step (4) is carried out at 60 ℃ for 4 hours.
8. The process according to any one of claims 1 to 7, wherein the short-chain ganoderan sulfuric acid derivative prepared by the process is used as a nonreactive product in livestock and poultry farming.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011590143.4A CN112458129B (en) | 2020-12-29 | 2020-12-29 | Preparation process of short-chain ganoderan sulfuric acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011590143.4A CN112458129B (en) | 2020-12-29 | 2020-12-29 | Preparation process of short-chain ganoderan sulfuric acid derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN112458129A CN112458129A (en) | 2021-03-09 |
| CN112458129B true CN112458129B (en) | 2022-02-15 |
Family
ID=74802095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202011590143.4A Active CN112458129B (en) | 2020-12-29 | 2020-12-29 | Preparation process of short-chain ganoderan sulfuric acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112458129B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114903101A (en) * | 2022-05-27 | 2022-08-16 | 内蒙古阿迪斯蒙医药有限公司 | Double-jujube lucid ganoderma tea and preparation method thereof |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR0156986B1 (en) * | 1995-02-20 | 1998-10-15 | 이신영 | Preparation process of polysaccharide by cultivating ganoderma lucidum |
| CN101157732A (en) * | 2007-11-12 | 2008-04-09 | 浙江大学 | Meat lucid ganoderma polysaccharide sodium sulphate and method for making same |
| CN101560260A (en) * | 2009-02-26 | 2009-10-21 | 浙江大学 | Technique for extracting polysaccharide in glossy ganoderma mycelium cell and method thereof |
| CN102972211A (en) * | 2012-12-21 | 2013-03-20 | 徐州工程学院 | Method for increasing growth speed of ganoderma lucidum mycelia and liquid fermentation biomass |
| CN104292357B (en) * | 2014-11-11 | 2017-01-25 | 牛睦元 | Extraction method of ganoderma lucidum polysaccharide |
| TWI673058B (en) * | 2018-07-20 | 2019-10-01 | 金穎生物科技股份有限公司 | Ganoderma lucidum complex polysaccharide composition |
| CN109234331A (en) * | 2018-08-02 | 2019-01-18 | 宁德师范学院 | A kind of Ganoderma lucidum submerged fermentation is naturally cultivated and tunning complete utilization method |
| CN111118083A (en) * | 2018-11-01 | 2020-05-08 | 王昌纬 | Method for extracting ganoderma lucidum polysaccharide |
| CN110564664B (en) * | 2019-09-23 | 2023-02-21 | 桂林理工大学 | Application of sulfated xylan derivative in promoting proliferation of probiotics in vitro |
| CN111620959A (en) * | 2020-06-08 | 2020-09-04 | 广州颜如玉生物科技有限公司 | Preparation method and application of ganoderma lucidum mycelium polysaccharide |
| CN111533823A (en) * | 2020-06-08 | 2020-08-14 | 广州颜如玉生物科技有限公司 | Process for extracting polysaccharide from ganoderma lucidum mycelia |
-
2020
- 2020-12-29 CN CN202011590143.4A patent/CN112458129B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN112458129A (en) | 2021-03-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111728976B (en) | Application of fucooligosaccharide in preparation of intestinal prebiotics | |
| CN112458129B (en) | Preparation process of short-chain ganoderan sulfuric acid derivative | |
| CN110642955B (en) | Esterified selenium polysaccharide and preparation method and application thereof | |
| CN109897117B (en) | Phosphorylated TP2 polysaccharide, and preparation method and application thereof | |
| CN1583802A (en) | Method for extracting beta-1,3-dextran | |
| CN112425684A (en) | Fermented feed additive with immunity enhancing effect and preparation method thereof | |
| CN112961259B (en) | Preparation method of taurolimus polysaccharide and application of taurolimus polysaccharide in field of improving intestinal function | |
| CN109430536B (en) | Natural immunopotentiator for aquatic products and application thereof | |
| CN116535535A (en) | Preparation method and application of astragalus polysaccharide | |
| CN103342755A (en) | Lycium barbarum polysaccharide homogeneous fraction IV, and preparation method and application thereof | |
| US10889608B2 (en) | Ester of aminoglycan and uses thereof | |
| CN115844849A (en) | Cellulose plant soft capsule and its preparation method | |
| CN112352887B (en) | Compound feed for mandarin fish and preparation method thereof | |
| CN111647094B (en) | Method for extracting nereis polysaccharide with auxiliary protection effect on chemical liver injury | |
| CN114642241A (en) | Composite plant polyphenol chelate and using method thereof | |
| CN110974849B (en) | Compound sea cucumber extract with hypoglycemic activity and preparation method and application thereof | |
| CN111643518B (en) | Fishery immunopotentiator and application thereof | |
| CN110835640A (en) | Extraction method and application of morchella polysaccharide | |
| CN100394923C (en) | Application of low molecular citrus pectin in regulation of blood sugar, blood fat and improvement of fatty liver | |
| CN101229183B (en) | Ribonucleic acid retrogradation snippet compound and applications thereof | |
| CN111265594A (en) | Medicinal preparation for repairing wound and preparation method thereof | |
| CN101816377A (en) | O-acyl carrageenin oligosaccharide feed additive | |
| CN114656575B (en) | Albizzia julibrissin heterogeneous polysaccharide, preparation method and application thereof | |
| CN117447621A (en) | Oligosaccharide, preparation method thereof and application thereof in aquatic feed | |
| CN114907575B (en) | Water-soluble lignin and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Preparation of a Short Chain Ganoderma Polysaccharide Sulfuric Acid Derivative Effective date of registration: 20221212 Granted publication date: 20220215 Pledgee: Qingdao Jinling Shengtai Financing Guarantee Co.,Ltd. Pledgor: QINGDAO RUNDA BIOTECHNOLOGY Co.,Ltd. Registration number: Y2022370010165 |
|
| PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
| PC01 | Cancellation of the registration of the contract for pledge of patent right |
Granted publication date: 20220215 Pledgee: Qingdao Jinling Shengtai Financing Guarantee Co.,Ltd. Pledgor: QINGDAO RUNDA BIOTECHNOLOGY Co.,Ltd. Registration number: Y2022370010165 |
|
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Preparation process of a short chain Ganoderma lucidum polysaccharide sulfate derivative Granted publication date: 20220215 Pledgee: China Construction Bank Co.,Ltd. Jimo Branch Pledgor: QINGDAO RUNDA BIOTECHNOLOGY Co.,Ltd. Registration number: Y2024370010065 |
|
| PE01 | Entry into force of the registration of the contract for pledge of patent right |