CN108542910A - The application of mannoglucan aldehydic acid oligosaccharides and its sulfated derivative in preparing antioxidant health-care product and drug - Google Patents
The application of mannoglucan aldehydic acid oligosaccharides and its sulfated derivative in preparing antioxidant health-care product and drug Download PDFInfo
- Publication number
- CN108542910A CN108542910A CN201810546910.8A CN201810546910A CN108542910A CN 108542910 A CN108542910 A CN 108542910A CN 201810546910 A CN201810546910 A CN 201810546910A CN 108542910 A CN108542910 A CN 108542910A
- Authority
- CN
- China
- Prior art keywords
- aldehydic acid
- mannoglucan aldehydic
- mannoglucan
- acid oligosaccharides
- sulfated derivative
- 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.)
- Granted
Links
- 239000002253 acid Substances 0.000 title claims abstract description 71
- 229920001542 oligosaccharide Polymers 0.000 title claims abstract description 65
- 150000002482 oligosaccharides Chemical class 0.000 title claims abstract description 64
- 239000003814 drug Substances 0.000 title claims abstract description 15
- 230000003078 antioxidant effect Effects 0.000 title claims abstract description 12
- 229940079593 drug Drugs 0.000 title claims abstract description 12
- 239000003963 antioxidant agent Substances 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims description 14
- 229910006069 SO3H Inorganic materials 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 229910052700 potassium Inorganic materials 0.000 claims description 8
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 claims description 7
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 6
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 claims description 6
- 229940097043 glucuronic acid Drugs 0.000 claims description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 239000002552 dosage form Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 238000012377 drug delivery Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 26
- 150000003254 radicals Chemical class 0.000 abstract description 13
- 230000036541 health Effects 0.000 abstract description 6
- 230000003064 anti-oxidating effect Effects 0.000 abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 abstract description 5
- 239000001301 oxygen Substances 0.000 abstract description 5
- 230000000694 effects Effects 0.000 description 32
- -1 glucuronic acid oligosaccharides Chemical class 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 150000003538 tetroses Chemical class 0.000 description 15
- 150000002016 disaccharides Chemical class 0.000 description 12
- 239000000523 sample Substances 0.000 description 12
- 239000012153 distilled water Substances 0.000 description 10
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- 229920001282 polysaccharide Polymers 0.000 description 10
- 239000005017 polysaccharide Substances 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- WFIYPADYPQQLNN-UHFFFAOYSA-N 2-[2-(4-bromopyrazol-1-yl)ethyl]isoindole-1,3-dione Chemical compound C1=C(Br)C=NN1CCN1C(=O)C2=CC=CC=C2C1=O WFIYPADYPQQLNN-UHFFFAOYSA-N 0.000 description 8
- 239000012295 chemical reaction liquid Substances 0.000 description 8
- 238000010612 desalination reaction Methods 0.000 description 8
- 238000001819 mass spectrum Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide pyridine complex Chemical compound O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 230000002000 scavenging effect Effects 0.000 description 7
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 235000006708 antioxidants Nutrition 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- 206010039966 Senile dementia Diseases 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 241000512259 Ascophyllum nodosum Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- DBTMGCOVALSLOR-DEVYUCJPSA-N (2s,3r,4s,5r,6r)-4-[(2s,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](CO)O[C@H](O)[C@@H]2O)O)O[C@H](CO)[C@H]1O DBTMGCOVALSLOR-DEVYUCJPSA-N 0.000 description 1
- OCZVHBZNPVABKX-UHFFFAOYSA-N 1,1-diphenyl-2-(2,4,6-trinitrophenyl)hydrazine;ethanol Chemical compound CCO.[O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NN(C=1C=CC=CC=1)C1=CC=CC=C1 OCZVHBZNPVABKX-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- 229920001543 Laminarin Polymers 0.000 description 1
- 239000005717 Laminarin Substances 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010029164 Nephrotic syndrome Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000010100 anticoagulation Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 238000006897 homolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- PANJMBIFGCKWBY-UHFFFAOYSA-N iron tricyanide Chemical compound N#C[Fe](C#N)C#N PANJMBIFGCKWBY-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 208000018937 joint inflammation Diseases 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 1
- 239000011806 microball Substances 0.000 description 1
- 208000009928 nephrosis Diseases 0.000 description 1
- 231100001027 nephrosis Toxicity 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 230000000324 neuroprotective effect Effects 0.000 description 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 239000012064 sodium phosphate buffer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- A61K31/702—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/125—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates
-
- 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
- A61K31/7024—Esters of saccharides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Mycology (AREA)
- Biochemistry (AREA)
- Toxicology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
The invention discloses the application of mannoglucan aldehydic acid oligosaccharides and its sulfated derivative in preparing antioxidant health-care product and drug；Mannoglucan aldehydic acid oligosaccharides and its sulfated derivative have significant antioxidation, can eliminate ultra-oxygen anion free radical, organic free radical and hydroxy radical etc., the anti-oxidation medicine and health products that can be used for preparing.
Description
Technical field
The invention belongs to biomedicine fields, are related to mannoglucan aldehydic acid oligosaccharides and its sulfated derivative anti-oxidant
Application in health products and drug.
Background technology
Free radical is the atom or group with unpaired electron that simple substance homolysis generates, and is ubiquitous, free radical
Approach to human body attack be it is various, it is existing ex vivo, also have from extraneous.When the free radical in human body is more than
A certain amount, and it is out of hand when, these free radicals will run chaotically and run helter-skelter, and remove attack cells film, go and serum antiprotease send out
Raw reaction, or even go to rob electronics with gene, various injuries are caused to our body, it is miscellaneous to generate various difficulties
Disease.Research shows that it has close relationship, such as neurodegenerative disease, tumour, aging etc. with a variety of diseases.So energy
Enough generations for effectively inhibiting free radical have prevention and cure relevant disease in a sense.
Oligosaccharides has a variety of effects, such as influences body enteron aisle ecology and physiological effect, and anticoagulation is anti-inflammatory, improves body
It is immune, anti-senile dementia isoreactivity.Such as Chinese patent 201410092395.2, discloses mannoglucan aldehydic acid oligosaccharides and preparing
Treat or prevent Parkinson's disease and/or medicine for senile dementia and/or the application in health products；Chinese patent
201510648272.7, it discloses mannoglucan aldehydic acid widow carbohydrates and their derivative and is preparing treatment and/or preventing nephrosis drug
Or the application in health products.
Up to the present, anti-oxidation health is not being prepared about mannoglucan aldehydic acid oligosaccharides and its sulfated derivative
Application in product and drug.
Invention content
The application of mannoglucan aldehydic acid oligosaccharides and its sulfated derivative in preparing antioxidant health-care product and drug.Institute
The sulphation sweet dew glucuronic acid oligosaccharides stated has following feature：
(1) saccharogenesis is organized：Mannose and glucuronic acid or its salt；
(2) glucuronic acid or its salt that the mannose of 2- connections is connected with 4- alternately connect；
(3) wherein sulfated derivative refers to may have sulphation substitution on mannose and glucuronic acid residue.
(4) its structural formula is following general formula (I)s or (II)
In formula (I), R SO3Na, SO3H, SO3The one or two or more kinds of K or H；R ' be H, Na or K in one kind or
Two kinds or more, integers of the n between 0-8；
In formula (II), R SO3Na, SO3H, SO3The one or two or more kinds of K or H；
R ' is the one or two or more kinds in H, Na or K, integers of the n between 0-8.
The drug be containing mannoglucan aldehydic acid oligosaccharides and its sulfated derivative and pharmaceutically acceptable carrier and/
Or the pharmaceutical composition of excipient.
Carrier includes sodium alginate micro ball, liposome etc..
Excipient：Such as mannitol, magnesium stearate, starch, cyclodextrin.
The dosage form of the drug is injection, oral preparation or local administration preparation.
The mannoglucan aldehydic acid oligosaccharides and its sulfated derivative of the present invention has significantly antioxidation, and poison is secondary to be made
With small, safely and effectively, can be used for preparing anti-oxidation medicine and health products.
Description of the drawings
The gel chromatography figure of alcohol eluent in Fig. 1 oligosaccharides preparation process；
The ESI-MS figures and HPLC figures a of Fig. 2 mannoglucan aldehydic acid oligosaccharides G1-G4 is G4；B is G3；C is G2；D is G1；
The ESI-MS of Fig. 3 sulphation mannoglucan aldehydic acid oligosaccharides GM2S1 schemes；
The ESI-MS of Fig. 4 sulphation mannoglucan aldehydic acid oligosaccharides GM2S2 schemes；
The ESI-MS of Fig. 5 sulphation mannoglucan aldehydic acid oligosaccharides GM4S1 schemes；
The ESI-MS of Fig. 6 sulphation mannoglucan aldehydic acid oligosaccharides GM4S2 schemes；
The ESI-MS of Fig. 7 sulphation mannoglucan aldehydic acid oligosaccharides GM4S3 schemes；
The ESI-MS of Fig. 8 sulphation mannoglucan aldehydic acid oligosaccharides GM6S1 schemes；
The ESI-MS of Fig. 9 sulphation mannoglucan aldehydic acid oligosaccharides GM6S2 schemes；
The ESI-MS of Figure 10 sulphation mannoglucan aldehydic acid oligosaccharides GM6S3 schemes；
The removal hydroxy radical of Figure 11 mannoglucan aldehydic acid oligosaccharides and its sulfated derivative is activity；
The removal superoxide radical activity of Figure 12 mannoglucan aldehydic acid oligosaccharides and its sulfated derivative；
The reducing power of Figure 13 mannoglucan aldehydic acid oligosaccharides and its sulfated derivative activity；
The removal organic free radical of Figure 14 mannoglucan aldehydic acid oligosaccharides and its sulfated derivative is active (DPPH).
Specific implementation mode
The present invention is specifically described with embodiment below, but the present invention is not only limited in following case study on implementation model
It encloses.
The preparation of 1 mannoglucan aldehydic acid oligosaccharides of embodiment
By dry kelp using being extracted 3 hours at 100 DEG C of the distilled water of 30 times of quality, extracting solution after concentration, adds by filtering
Ethyl alcohol collects precipitation after standing 12 hours, sinks to and vacuum dried obtain laminarin to final concentration of 75% precipitation.By kelp
Polysaccharide sample, which is dissolved in the sulfuric acid solution that mass concentration is 4% (solid-liquid ratio 60mg/mL), to be heated to reflux 5 hours, and hydroxide is used
Barium is neutralized to PH=6-7, centrifuges, 1/5th of supernatant concentration to initial volume, activated carbon column chromatography on concentrate, first
With distillation water balance, 50%-90% ethanol gradient elutions are then used, 50%-90% ethanol eluates are concentrated into initial volume
1/5th, boil off ethyl alcohol, directly upper Bio-gel P4 column chromatographies, isolated five components, to what is collected above
Sample carries out ESI-MS and HPLC analyses, as illustrated in fig. 1 and 2.As a result the structure of oligosaccharides is further confirmed that.The results show that G1-G4
Respectively eight sugar of mannoglucan aldehydic acid, six sugar, tetrose and disaccharides.Its structure meets structural formula shown in following formula：
Wherein G1 is that mannoglucan aldehydic acid eight is sugared, n=3 in formula；
G2 is that mannoglucan aldehydic acid six is sugared, n=2 in formula；
G3 is mannoglucan aldehydic acid tetrose, n=1 in formula；
G4 is mannoglucan aldehydic acid disaccharides, n=0 in formula.
The preparation of 2 sulphation mannoglucan aldehydic acid oligosaccharides GM2S1 of embodiment
The mannoglucan aldehydic acid oligosaccharide monomer G4 (mannoglucan aldehydic acid disaccharides) obtained in embodiment 1 is protected in nitrogen
It is dissolved under the conditions of shield in DMF (0.05g/ml), adds 3.30g sulfur trioxide pyridine salt, be stirred at room temperature 24 hours.It will reaction
Liquid pours into 4 times of ice distilled water, neutralizes, Sephadex G10 desalinations.Eluent is concentrated, Bio-gel P4 isolate and purify to obtain
GM2S1.Mass spectrum (following Fig. 3) result shows that GM2S1 is GlcAMan (SO3H)3-6。
The preparation of 3 sulphation mannoglucan aldehydic acid oligosaccharides GM2S2 of embodiment
The mannoglucan aldehydic acid oligosaccharide monomer G4 (mannoglucan aldehydic acid disaccharides) obtained in embodiment 1 is protected in nitrogen
It is dissolved under the conditions of shield in DMF (0.05g/ml), adds 1.80g sulfur trioxide pyridine salt, be stirred at room temperature 24 hours.It will reaction
Liquid pours into 4 times of ice distilled water, neutralizes, Sephadex G10 desalinations.Eluent is concentrated, Bio-gel P4 isolate and purify to obtain
GM2S1.Mass spectrum (following Fig. 4) result shows that GM2S1 is GlcAMan (SO3H)1-3。
The preparation of 4 sulphation mannoglucan aldehydic acid oligosaccharides GM4S1 of embodiment
The mannoglucan aldehydic acid oligosaccharide monomer G3 (mannoglucan aldehydic acid tetrose) obtained in embodiment 1 is protected in nitrogen
It is dissolved under the conditions of shield in DMF (0.05g/ml), adds 3.54g sulfur trioxide pyridine salt, be stirred at room temperature 24 hours.It will reaction
Liquid pours into 4 times of ice distilled water, neutralizes, Sephadex G10 desalinations.Eluent is concentrated, Bio-gel P4 isolate and purify to obtain
GM4S1.Mass spectrum (following Fig. 5) result shows that GM4S1 is GlcA2Man2(SO3H)8-11。
The preparation of 5 sulphation mannoglucan aldehydic acid oligosaccharides GM4S2 of embodiment
The mannoglucan aldehydic acid oligosaccharide monomer G3 (mannoglucan aldehydic acid tetrose) obtained in embodiment 1 is protected in nitrogen
It is dissolved under the conditions of shield in DMF (0.05g/ml), adds 2.19g sulfur trioxide pyridine salt, be stirred at room temperature 24 hours.It will reaction
Liquid pours into 4 times of ice distilled water, neutralizes, Sephadex G10 desalinations.Eluent is concentrated, Bio-gel P4 isolate and purify to obtain
GM4S2.Mass spectrum (following Fig. 6) result shows that GM4S2 is GlcA2Man2(SO3H)5-9。
The preparation of 6 sulphation mannoglucan aldehydic acid oligosaccharides GM4S3 of embodiment
The mannoglucan aldehydic acid oligosaccharide monomer G3 (mannoglucan aldehydic acid tetrose) obtained in embodiment 1 is protected in nitrogen
It is dissolved under the conditions of shield in DMF (0.05g/ml), adds 0.93g sulfur trioxide pyridine salt, be stirred at room temperature 24 hours.It will reaction
Liquid pours into 4 times of ice distilled water, neutralizes, Sephadex G10 desalinations.Eluent is concentrated, Bio-gel P4 isolate and purify to obtain
GM4S3.Mass spectrum (following Fig. 7) result shows that GM4S3 is GlcA2Man2(SO3H)1-5。
The preparation of 7 sulphation mannoglucan aldehydic acid oligosaccharides GM6S1 of embodiment
The mannoglucan aldehydic acid oligosaccharide monomer G2 obtained in embodiment 1 (six sugar of mannoglucan aldehydic acid) is protected in nitrogen
It is dissolved under the conditions of shield in DMF (0.05g/ml), adds 2.85g sulfur trioxide pyridine salt, be stirred at room temperature 24 hours.It will reaction
Liquid pours into 4 times of ice distilled water, neutralizes, Sephadex G10 desalinations.Eluent is concentrated, Bio-gel P4 isolate and purify to obtain
GM6S1.Mass spectrum (following Fig. 8) result shows that GM6S1 is GlcA3Man3(SO3H)8-15。
The preparation of 8 sulphation mannoglucan aldehydic acid oligosaccharides GM6S2 of embodiment
The mannoglucan aldehydic acid oligosaccharide monomer G2 obtained in embodiment 1 (six sugar of mannoglucan aldehydic acid) is protected in nitrogen
It is dissolved under the conditions of shield in DMF (0.05g/ml), adds 2.09g sulfur trioxide pyridine salt, be stirred at room temperature 24 hours.It will reaction
Liquid pours into 4 times of ice distilled water, neutralizes, Sephadex G10 desalinations.Eluent is concentrated, Bio-gel P4 isolate and purify to obtain
GM6S2.Mass spectrum (following Fig. 9) result shows that GM6S2 is GlcA3Man3(SO3H)4-10。
The preparation of 9 sulphation mannoglucan aldehydic acid oligosaccharides GM6S3 of embodiment
The mannoglucan aldehydic acid oligosaccharide monomer G2 obtained in embodiment 1 (six sugar of mannoglucan aldehydic acid) is protected in nitrogen
It is dissolved under the conditions of shield in DMF (0.05g/ml), adds 1.17g sulfur trioxide pyridine salt, be stirred at room temperature 24 hours.It will reaction
Liquid pours into 4 times of ice distilled water, neutralizes, Sephadex G10 desalinations.Eluent is concentrated, Bio-gel P4 isolate and purify to obtain
GM6S3.Mass spectrum (following Figure 10) result shows that GM6S3 is GlcA3Man3(SO3H)1-6。
The antioxidant activity of 10 mannoglucan aldehydic acid of embodiment and its sulfated derivative
The mannoglucan aldehydic acid oligosaccharides and its sulfated derivative that are obtained in embodiment 1-9 are surveyed for antioxidant activity
It is fixed.In terms of antioxidant activity includes following four：Hydroxy radical is removed, ultra-oxygen anion free radical is removed, removal DPPH is free
Base and reducing power reflect the antioxidant activity of mannoglucan aldehydic acid oligosaccharides and its sulfated derivative.1, removal hydroxyl is free
The measurement of the effect of base is with the following method：By 2mmol/L ethylenediamine tetra-acetic acids-molysite (0.5mL), sodium phosphate buffer
The addition of (150mM, pH=7.4,1mL), safron (being dissolved in phosphate buffer, 1mL) and 3% hydrogen peroxide respectively sequentially is not
With (1mL) in the sample liquid of concentration, then 37 DEG C of water-baths 30min, 520nm measure absorbance.Control group is substituted using distilled water
Sample.Scavenging capacity=A samples/A controls × 100.2, remove the measurement of the effect of superoxide radical with the following method：It will
0.5mL reduced coenzymes (NADH) (0.0365%), 0.5mL tetrazolium blues (NBT) (0.0246%) and 0.5mL azophenlyene sulfuric acid first
(3mL, sample is with 16mmol/L, the trihydroxy methyl amino of pH=8 by the sample liquid of sequence addition various concentration for ester (0.002%)
Methane hydrochloride salt buffer dissolves).Control group substitutes sample liquid using buffer solution.Scavenging capacity=(1-A samples/A controls) ×
100.3, remove the measurement of the effect of DPPH free radicals with the following method：The DPPH ethanol solutions of 1mL 0.1mmol/L are added
Enter into the sample solution of various concentration (3mL, sample are dissolved with 50% ethyl alcohol), is aggressively shaken, is placed at room temperature for 20min, finally
It is measured in 517nm.Control group substitutes sample liquid using 50% ethyl alcohol.Scavenging capacity=(1-A samples/A controls) × 100.4, also
With the following method, the 1.25mL potassium ferricyanides (1%) are added in the sample solution of various concentration for the measurement of proper energy power
(1mL), then 50 DEG C of water-bath 20min, are added trichloroacetic acid (2.5mL) and stop reaction, be eventually adding ferric trichloride (1.5mL),
700nm measures absorbance.
The scavenging effect for the free radical that sample generates Fenton systems is illustrated to the scavenging effect of hydroxyl radical free radical.Figure
11 illustrate that all samples all have significantly to the scavenging effect of hydroxyl radical free radical, and certain concentration dependent is presented.Than
It is active compared with the anti-hydroxy radical of mannoglucan aldehydic acid oligosaccharides, it can be found that the activity of tetrose is better than disaccharides and six sugar.In sulfuric acid
In terms of change degree, the activity of low sulphated disaccharides and tetrose is higher than high sulphation disaccharides and tetrose；But high six sugar of sulphation
Activity be higher than the activity of low sulphated disaccharides and tetrose.For entirety, the activity of tetrose and low sulphated tetrose is best.Than
Compared with algal polysaccharide sulfate, (under 7mg/ml concentration, 30%) activity only has, it can be found that the hydroxy radical activity of oligosaccharides is remote
Far above algal polysaccharide sulfate.There is the mechanism of two kinds of removal hydroxy radicals of document report：The first mechanism is to inhibit hydroxyl
The generation of free radical, second is to remove the hydroxy radical generated.The former mechanism is related with chelated metal ions, this depends on
In molecular weight, sulfate radical content and glucuronic acid content.Therefore speculate that it mainly may be related with the generation of hydroxy radical is inhibited.
Although superoxides is a weak oxidant in body, the degradation that it can continue generates a series of
The active oxygen of new activation, to lead to the peroxidization of lipid indirectly or directly result in the generation of disease, such as joint
Inflammation, senile dementia etc..It is therefore desirable to discuss to remove the activity of ultra-oxygen anion free radical and the relationship of neuroprotective activity.Figure
12 show the removing superoxide anion effect of mannoglucan aldehydic acid oligosaccharides and its sulfated derivative.It can from figure
Go out, certain concentration dependent is presented in concentration and the activity of polysaccharide.Compared to sulphation mannoglucan aldehydic acid oligosaccharide derivative,
The hydroxy radical activity of mannoglucan aldehydic acid oligosaccharide monomer will be far smaller than sulphation mannoglucan aldehydic acid oligosaccharide derivative；
And degree is higher, anti-superoxide radical activity is also stronger to a certain extent, and when the degree of polymerization is 2, such case is most bright
It is aobvious, but when the degree of polymerization is 4 and 6, the anti-active variation of superoxide radical is relatively small.Finally, the anti-super oxygen of oligosaccharide monomer
Free radical activity is related with the degree of polymerization of oligosaccharides, and the degree of polymerization is bigger, and anti-superoxide radical activity is stronger；Therefore speculate the poly- of oligosaccharides
It is right that there are certain relationships with anti-superoxide radical to a certain extent with degree.Compare algal polysaccharide sulfate,
It can be found that (when the concentration of 50 μ g/ml, activity can reach activity 80%) far better than oligosaccharides to algal polysaccharide sulfate
And its (in the concentration of 0.22mg/ml, 98%) activity can reach GM4S3 samples sulfated derivative.
Reducing power experiment is mainly used for reducing power of the determination sample to ferric iron and the iron cyanide, as anti-oxidant energy
One important indicator of power.Figure 13 is shown：The reducing power and sample of mannoglucan aldehydic acid oligosaccharides and its sulfated derivative
Concentration it is related in linear positive.Compare mannoglucan aldehydic acid oligosaccharides, it can be found that it is related with the degree of polymerization, the degree of polymerization is bigger,
Relative activity is stronger.Compare degree, it can be found that the activity in low sulphated disaccharides and tetrose is relatively higher than high sulfuric acid
Change disaccharides and tetrose, however the phenomenon of six sugar and its sulfated derivative activity is still without method interpretation.Compare algal polysaccharide sulfate
The activity of (its reducing power is about 0.1 when 2.5mg/ml concentration), mannoglucan aldehydic acid oligosaccharides is slightly above algal polysaccharide sulfuric acid
Ester.
It is opposite to the scavenging effect experiment (Figure 14) of DPPH free radicals to save compared with above-mentioned three kinds of antioxidant activity methods
When and quickly.Its result is not linear related to reducing power experiment.But the positive dependence of concentration is presented in all samples.Compare
Mannoglucan aldehydic acid oligosaccharides, it can be found that it is related with the degree of polymerization, the degree of polymerization is bigger, and relative activity is stronger.Compare sulphation
Degree, it can be found that the activity in low sulphated disaccharides and tetrose is relatively higher than high sulphation disaccharides and tetrose, however six sugar and
The phenomenon of its sulfated derivative activity is still without method interpretation.Compare low-molecular-weight algal polysaccharide sulfate (when 7mg/ml concentration its
The ability for removing organic free radical is about that 80%), the activity of mannoglucan aldehydic acid oligosaccharides is slightly above algal polysaccharide sulfate.
Claims (4)
1. the application of mannoglucan aldehydic acid oligosaccharides and its sulfated derivative in preparing antioxidant health-care product and drug；It is special
Sign is：The structural formula of the mannoglucan aldehydic acid oligosaccharides and its sulfated derivative is following general formula (I)s or (II)
In one kind or two kinds；
In formula (I), R SO3Na, SO3H, SO3The one or two or more kinds of K or H；R ' is one kind or two kinds in H, Na or K
More than, integers of the n between 0-8；
In formula (II), R SO3Na, SO3H, SO3The one or two or more kinds of K or H；R ' is one kind or two kinds in H, Na or K
More than, integers of the n between 0-8.
2. application according to claim 1, it is characterised in that：
The mannoglucan aldehydic acid oligosaccharides and its sulfated derivative have following feature：
(1) saccharogenesis is organized：Mannose and glucuronic acid or its salt；
(2) glucuronic acid or its salt that the mannose of 2- connections is connected with 4- alternately connect；
(3) wherein sulfated derivative refers to may have sulphation substitution on mannose and glucuronic acid residue.
3. application according to claim 1, it is characterised in that：The drug be comprising mannoglucan aldehydic acid oligosaccharides and its
The pharmaceutical composition of sulfated derivative and other pharmaceutically acceptable carriers and/or excipient.
4. application according to claim 1, it is characterised in that：The dosage form of the drug is injection, oral preparation or office
Portion's drug-delivery preparation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810546910.8A CN108542910B (en) | 2018-05-31 | 2018-05-31 | Application of sulfated derivative of manno-glucuronic acid oligosaccharide in preparation of antioxidant drugs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810546910.8A CN108542910B (en) | 2018-05-31 | 2018-05-31 | Application of sulfated derivative of manno-glucuronic acid oligosaccharide in preparation of antioxidant drugs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108542910A true CN108542910A (en) | 2018-09-18 |
| CN108542910B CN108542910B (en) | 2020-06-12 |
Family
ID=63511525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810546910.8A Active CN108542910B (en) | 2018-05-31 | 2018-05-31 | Application of sulfated derivative of manno-glucuronic acid oligosaccharide in preparation of antioxidant drugs |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108542910B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109293717A (en) * | 2018-09-30 | 2019-02-01 | 河北大学 | A kind of preparation method of mannuronic acid oligosaccharide and its application in the combination antibacterial agent that preparation inhibits drug-fast bacteria |
| CN110917208A (en) * | 2019-12-27 | 2020-03-27 | 浙江医院 | Application of sulfated mannoglucuronhexaose in preventing and treating atherosclerosis |
| CN111249288A (en) * | 2019-12-27 | 2020-06-09 | 浙江医院 | Application of mannoglucuronic acid oligosaccharide and derivatives thereof in preparation of medicine for treating and/or preventing HCMV (human chorionic gonadotropin) |
| CN112933105A (en) * | 2021-02-10 | 2021-06-11 | 浙江工业大学 | Application of mannoglucuronate poly (oligo) saccharide and sulfated derivative in preparation of medicine for treating non-alcoholic fatty liver disease |
| CN113940939A (en) * | 2021-11-19 | 2022-01-18 | 浙江大学 | Application of oligomannose, polyxylose and derivative in preparing medicine for preventing and treating senility |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103800348A (en) * | 2014-03-13 | 2014-05-21 | 中国科学院海洋研究所 | Application of mannose glucuronic acid oligosaccharide in preparation of medicine and/or healthcare product for treating or preventing Parkinson's disease and/or senile dementia |
-
2018
- 2018-05-31 CN CN201810546910.8A patent/CN108542910B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103800348A (en) * | 2014-03-13 | 2014-05-21 | 中国科学院海洋研究所 | Application of mannose glucuronic acid oligosaccharide in preparation of medicine and/or healthcare product for treating or preventing Parkinson's disease and/or senile dementia |
Non-Patent Citations (2)
| Title |
|---|
| CELINA MARIA P. GUERRA DORE等: "A sulfated polysaccharide, fucans, isolated from brown algae Sargassum vulgare with anticoagulant, antithrombotic, antioxidant and anti-inflammatory effects", 《CARBOHYDRATE POLYMERS》 * |
| 李霞等: "褐藻多糖生物活性的研究进展", 《中国海洋药物》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109293717A (en) * | 2018-09-30 | 2019-02-01 | 河北大学 | A kind of preparation method of mannuronic acid oligosaccharide and its application in the combination antibacterial agent that preparation inhibits drug-fast bacteria |
| CN110917208A (en) * | 2019-12-27 | 2020-03-27 | 浙江医院 | Application of sulfated mannoglucuronhexaose in preventing and treating atherosclerosis |
| CN111249288A (en) * | 2019-12-27 | 2020-06-09 | 浙江医院 | Application of mannoglucuronic acid oligosaccharide and derivatives thereof in preparation of medicine for treating and/or preventing HCMV (human chorionic gonadotropin) |
| CN112933105A (en) * | 2021-02-10 | 2021-06-11 | 浙江工业大学 | Application of mannoglucuronate poly (oligo) saccharide and sulfated derivative in preparation of medicine for treating non-alcoholic fatty liver disease |
| CN113940939A (en) * | 2021-11-19 | 2022-01-18 | 浙江大学 | Application of oligomannose, polyxylose and derivative in preparing medicine for preventing and treating senility |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108542910B (en) | 2020-06-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108542910A (en) | The application of mannoglucan aldehydic acid oligosaccharides and its sulfated derivative in preparing antioxidant health-care product and drug | |
| Mao et al. | Anti-tumor and immunomodulatory activity of selenium (Se)-polysaccharide from Se-enriched Grifola frondosa | |
| Ke et al. | Antioxidant acitivity in vitro and in vivo of the capsule polysaccharides from Streptococcus equi subsp. zooepidemicus | |
| Jia et al. | Antioxidant, immunomodulatory, oxidative stress inhibitory and iron supplementation effect of Astragalus membranaceus polysaccharide-iron (III) complex on iron-deficiency anemia mouse model | |
| Nie et al. | Bioactive polysaccharides from Cordyceps sinensis: Isolation, structure features and bioactivities | |
| Kardošová et al. | A biologically active fructan from the roots of Arctium lappa L., var. Herkules | |
| Zhang et al. | Phosphorylation and antiaging activity of polysaccharide from Trichosanthes peel | |
| JP6977059B2 (en) | Composition of mannurondioic acid | |
| Laparra et al. | Structural differences of prebiotic oligosaccharides influence their capability to enhance iron absorption in deficient rats | |
| EP1789439B1 (en) | A purified arabinogalactan-protein (agp) composition | |
| JP2001519471A (en) | Novel pectic polysaccharide purified from Angelica gigas nakai, its purification method and its use as immunostimulant | |
| Ng et al. | Chemical structures, extraction and analysis technologies, and bioactivities of edible fungal polysaccharides from Poria cocos: An updated review | |
| CN102234336A (en) | Fucoidan-galactosan sulfate, extracting, separating, and purifying method thereof, and application thereof | |
| US6726932B2 (en) | Fatty acid-containing composition | |
| CN108409621A (en) | A kind of dihydromyricetin selenium compound for treating liver cancer and related liver disease | |
| CN108392485A (en) | Sulphation mannoglucan aldehydic acid oligosaccharides is preparing the application in treating or preventing neurodegenerative disease drug or health products | |
| Lin et al. | Extraction, structure and bioactivities of polysaccharides from Sanghuangporus spp.: A review | |
| WO1990009181A1 (en) | Anti-hiv drug | |
| Li et al. | Studies on the acid degradation process and in vitro immune activity of the polysaccharide H6PC20 in Hericium erinaceus | |
| EP3750923A1 (en) | Separated saposhnikovia divaricata polysaccharide and use thereof | |
| CN108904519A (en) | Hericium erinaceus Polysaccharides are in the purposes prepared in the drug for treating colitis and include its pharmaceutical composition | |
| WO1990008784A1 (en) | New sulfated polysaccharide, pharmaceutically acceptable salts thereof, preparation thereof, and drug containing the same as active ingredient | |
| CN114605568A (en) | Acidic polysaccharide and preparation method and application thereof | |
| WO1997022628A1 (en) | Intravascular membrane thickening inhibitor | |
| EP1398036B1 (en) | Ganoderma lucidum spores for treatment of systemic lupus erytrhomatosus (SLE) |
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 |