CN109430878B - 芦丁壳寡糖复合物及其制备方法和应用 - Google Patents
芦丁壳寡糖复合物及其制备方法和应用 Download PDFInfo
- Publication number
- CN109430878B CN109430878B CN201811222615.3A CN201811222615A CN109430878B CN 109430878 B CN109430878 B CN 109430878B CN 201811222615 A CN201811222615 A CN 201811222615A CN 109430878 B CN109430878 B CN 109430878B
- Authority
- CN
- China
- Prior art keywords
- rutin
- chitosan oligosaccharide
- compound
- chitosan
- molar ratio
- 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
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 title claims abstract description 144
- IVTMALDHFAHOGL-UHFFFAOYSA-N eriodictyol 7-O-rutinoside Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC=2C=C3C(C(C(O)=C(O3)C=3C=C(O)C(O)=CC=3)=O)=C(O)C=2)O1 IVTMALDHFAHOGL-UHFFFAOYSA-N 0.000 title claims abstract description 144
- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 title claims abstract description 144
- ALABRVAAKCSLSC-UHFFFAOYSA-N rutin Natural products CC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5 ALABRVAAKCSLSC-UHFFFAOYSA-N 0.000 title claims abstract description 144
- 235000005493 rutin Nutrition 0.000 title claims abstract description 144
- 229960004555 rutoside Drugs 0.000 title claims abstract description 144
- -1 Rutin chitosan oligosaccharide compound Chemical class 0.000 title claims abstract description 50
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- RQFQJYYMBWVMQG-IXDPLRRUSA-N chitotriose Chemical compound O[C@@H]1[C@@H](N)[C@H](O)O[C@H](CO)[C@H]1O[C@H]1[C@H](N)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)[C@@H](CO)O1 RQFQJYYMBWVMQG-IXDPLRRUSA-N 0.000 claims abstract description 55
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 claims abstract 8
- 239000000243 solution Substances 0.000 claims description 27
- 239000006228 supernatant Substances 0.000 claims description 15
- 238000001694 spray drying Methods 0.000 claims description 13
- 238000002156 mixing Methods 0.000 claims description 10
- 239000011259 mixed solution Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- 239000012530 fluid Substances 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 22
- 150000001875 compounds Chemical class 0.000 abstract description 14
- 230000003078 antioxidant effect Effects 0.000 abstract description 13
- 238000000034 method Methods 0.000 abstract description 13
- 235000019658 bitter taste Nutrition 0.000 abstract description 12
- 239000003963 antioxidant agent Substances 0.000 abstract description 10
- 235000006708 antioxidants Nutrition 0.000 abstract description 10
- 230000003647 oxidation Effects 0.000 abstract description 10
- 238000007254 oxidation reaction Methods 0.000 abstract description 10
- 239000003814 drug Substances 0.000 abstract description 8
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 7
- 235000013376 functional food Nutrition 0.000 abstract description 7
- 229940079593 drug Drugs 0.000 abstract description 5
- 239000002537 cosmetic Substances 0.000 abstract description 4
- 235000013305 food Nutrition 0.000 abstract description 3
- 238000012545 processing Methods 0.000 abstract description 2
- IKGXIBQEEMLURG-NVPNHPEKSA-N rutin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-NVPNHPEKSA-N 0.000 description 96
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- OHDRQQURAXLVGJ-HLVWOLMTSA-N azane;(2e)-3-ethyl-2-[(e)-(3-ethyl-6-sulfo-1,3-benzothiazol-2-ylidene)hydrazinylidene]-1,3-benzothiazole-6-sulfonic acid Chemical compound [NH4+].[NH4+].S/1C2=CC(S([O-])(=O)=O)=CC=C2N(CC)C\1=N/N=C1/SC2=CC(S([O-])(=O)=O)=CC=C2N1CC OHDRQQURAXLVGJ-HLVWOLMTSA-N 0.000 description 9
- 230000001580 bacterial effect Effects 0.000 description 8
- 238000004108 freeze drying Methods 0.000 description 8
- 238000002835 absorbance Methods 0.000 description 7
- 241000894006 Bacteria Species 0.000 description 6
- 241000191967 Staphylococcus aureus Species 0.000 description 6
- 230000003385 bacteriostatic effect Effects 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 230000001965 increasing effect Effects 0.000 description 6
- 238000011160 research Methods 0.000 description 5
- 229920001661 Chitosan Polymers 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 4
- GLEVLJDDWXEYCO-UHFFFAOYSA-N Trolox Chemical compound O1C(C)(C(O)=O)CCC2=C1C(C)=C(C)C(O)=C2C GLEVLJDDWXEYCO-UHFFFAOYSA-N 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 230000005714 functional activity Effects 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 150000008442 polyphenolic compounds Chemical class 0.000 description 4
- 235000013824 polyphenols Nutrition 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 229910021642 ultra pure water Inorganic materials 0.000 description 4
- 239000012498 ultrapure water Substances 0.000 description 4
- 239000012224 working solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- 229930003935 flavonoid Natural products 0.000 description 3
- 235000017173 flavonoids Nutrition 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920001542 oligosaccharide Polymers 0.000 description 3
- 150000002482 oligosaccharides Chemical class 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000001896 rotating frame Overhauser effect spectroscopy Methods 0.000 description 3
- 230000002000 scavenging effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 241000192125 Firmicutes Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 210000000170 cell membrane Anatomy 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 230000007760 free radical scavenging Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000001000 micrograph Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- FJERMCQUSONQAU-UHFFFAOYSA-N 2,4,6-tripyridin-2-yl-1h-triazine Chemical compound N1N(C=2N=CC=CC=2)N=C(C=2N=CC=CC=2)C=C1C1=CC=CC=N1 FJERMCQUSONQAU-UHFFFAOYSA-N 0.000 description 1
- 240000004784 Cymbopogon citratus Species 0.000 description 1
- 235000017897 Cymbopogon citratus Nutrition 0.000 description 1
- 240000008620 Fagopyrum esculentum Species 0.000 description 1
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- 239000006137 Luria-Bertani broth Substances 0.000 description 1
- 244000046101 Sophora japonica Species 0.000 description 1
- 235000010586 Sophora japonica Nutrition 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000010100 anticoagulation Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000002815 broth microdilution Methods 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002215 flavonoids Chemical group 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 238000001208 nuclear magnetic resonance pulse sequence Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 238000000513 principal component analysis Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000001878 scanning electron micrograph Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000012137 tryptone Substances 0.000 description 1
- 230000008728 vascular permeability Effects 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Images
Classifications
-
- 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
- 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
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- 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
- 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
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1545—Six-membered rings
-
- 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)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Mycology (AREA)
- Nutrition Science (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Birds (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Toxicology (AREA)
- Biochemistry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Botany (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明属于食品加工领域,具体涉及一种芦丁壳寡糖复合物及其制备方法和应用。包括芦丁以及壳寡糖。所述的芦丁与壳寡糖的摩尔比为1:1‑5。本发明提供利用壳寡糖改善芦丁抑菌性和抗氧化性,改善芦丁水溶性、降低芦丁苦味的方法,以芦丁和壳寡糖为原料,根据二者活性成分和结构的特点,通过微包埋技术制备芦丁和壳寡糖的复合物。测试复合物的抑菌性和抗氧化能力均得到显著提高,水溶性明显改善,苦味明显下降,结果显示了良好的可行性和可重复性。这为芦丁在功能性食品,医药和化妆品等领域的创新性应用提供了新的思路。
Description
技术领域
本发明属于食品加工领域,具体涉及一种芦丁壳寡糖复合物及其制备方法和应用。
背景技术
芦丁属于黄酮类化合物,广泛存在于芸香草、槐米、荞麦中,具有抗氧化、抗菌、抗病毒、防癌、抗辐射、降低血管通透性和脆性等功效,是治疗心血管病药物的重要原料。但由于芦丁具有明显的苦味且难溶于水,使得它在功能性食品以及制药等领域的应用受到限制。壳寡糖是由天然糖中唯一带正电的碱性氨基多糖壳聚糖降解而得,溶解性和吸收性均优于壳聚糖,且具有抗氧化、增强免疫力、抑菌、抗糖尿病、抗肿瘤等多种生物活性作用。
多酚和寡糖间可以发生非共价和共价的相互作用,研究表明,寡糖能够增强多酚的抗氧化、降血糖、预防心血管疾病、抗凝血等生物活性,并影响多酚生物利用率,能够改善食品风味以及营养价值,抑制氧化以及褐变等。
目前利用壳寡糖增强芦丁的物理性质及功能活性的研究还未见报道。本发明采用天然寡糖改变天然多酚,利用微包埋技术制备两者的复合物,促进天然产物在各个领域的利用率。
发明内容
本发明的目的在于提供一种芦丁壳寡糖复合物及其制备方法和应用。
本发明为实现上述目的,采用以下技术方案:
一种芦丁壳寡糖复合物,其特征在于,包括芦丁以及壳寡糖。
所述的芦丁与壳寡糖的摩尔比为1:1-5。
所述的壳寡糖的分子量为980Da。
本发明还包括一种制备所述的芦丁壳寡糖复合物的方法,包括下述步骤:将芦丁与壳寡糖按比例混合后、离心、取上清液、喷雾干燥制得。
具体步骤如下:
⑴分别配制芦丁溶液、壳寡糖溶液,将两者混合,在振荡器上振荡5-30min;
⑵混合液在15-30℃,以1,000×g离心5-20min后取上清;
⑶将上清液在80-120℃、0.5-5L/h的条件下进行喷雾干燥,得到芦丁壳寡糖复合物。
本发明还包括一种所述的芦丁壳寡糖复合物的应用,主要应用于功能性食品领域、医药领域或者化妆品领域。
与现有技术相比,本发明的有益效果是:
本发明提供利用壳寡糖改善芦丁抑菌性和抗氧化性,改善芦丁水溶性、降低芦丁苦味的方法,以芦丁和壳寡糖为原料,根据二者活性成分和结构的特点,通过微包埋技术制备芦丁和壳寡糖的复合物。测试复合物的抑菌性和抗氧化能力均得到显著提高,水溶性明显改善,苦味明显下降,结果显示了良好的可行性和可重复性。这为芦丁在功能性食品,医药和化妆品等领域的创新性应用提供了新的思路。
1、通过对复合物的抑菌性进行分析得出,芦丁壳寡糖复合物对大肠杆菌和金黄色葡萄球菌的抑制效果均明显优于芦丁或者壳寡糖单体。
2、通过对复合物的抗氧化能力进行分析得出,芦丁壳寡糖复合物对ABTS+与DPPH的清除率均明显优于芦丁或者壳寡糖单体。
3、通过高效液相色谱法测定可知,将壳寡糖加入芦丁制成芦丁壳寡糖复合物,显著增加了芦丁在水中的溶解度。
4、通过电子舌测定可知,芦丁壳寡糖复合物的苦味明显低于芦丁。
5、芦丁来源广泛,具有良好的抑菌性和抗氧化性,在功能性食品及医药领域具有广泛的应用前景。因此,改善芦丁的水溶性,降低芦丁苦味对增加其生物利用率和扩展其应用具有重大的研究意义。本发明采用喷雾干燥的方法制备芦丁壳寡糖复合物,并采用扫描电镜、核磁共振氢谱扫描等分析技术对该复合物的分子结构进行解析。结果表明芦丁的A、B环与壳寡糖靠近形成了稳定的复合物。抑菌试验证实复合物对革兰氏阳性菌和革兰氏阴性菌的抑制作用均显著优于芦丁和壳寡糖单体,抗氧化实验表明复合物对自由基的清除作用大大增强,经高效液相色谱法分析可知,复合物使得芦丁在水中的溶解度得到显著提高,电子舌测试显示复合物苦味明显低于芦丁。这为芦丁在功能性食品,医药和化妆品等领域的创新性应用提供了新的思路,尤其是在功能性食品领域具有广阔的应用前景。
附图说明
图1为芦丁壳寡糖复合物处理前后大肠杆菌(a,b)和金黄色葡萄球菌(c,d)的扫描电镜图;
图2为实施例喷雾干燥芦丁与摩尔比分别为1:1,1:3,1:5的芦丁壳寡糖复合物以及对比例冷冻干燥的水溶性对比图;
图3为实施例喷雾干燥芦丁与摩尔比分别为1:1,1:3,1:5的芦丁壳寡糖复合物以及对比例冷冻干燥苦味评价的PCA图;
图4为芦丁与摩尔比分别为1:1,1:3,1:5的芦丁壳寡糖复合物的扫描电镜图;
图5为芦丁与摩尔比分别为1:1,1:3,1:5的芦丁壳寡糖复合物的1H-NMR图;
图6为摩尔比为1:1的芦丁壳寡糖复合物的ROESY图。
具体实施方式
为了使本技术领域的技术人员更好地理解本发明的技术方案,下面结合附图和最佳实施例对本发明作进一步的详细说明。
材料与试剂
芦丁(MW664.56Da),购于北京索莱宝科技有限公司;壳寡糖(MW980Da),购于浙江金壳药业有限公司;2,2连氨基双二铵盐(ABTS)、2,4,6-三吡啶基三嗪(TPTZ)、6-羟基-2,5,7,8-四甲基色烷-2-羧酸(Trolox)、1,1-二苯基-2-三硝基苯肼(DPPH)均购于美国Sigma公司;大肠杆菌(ATCC10305)和金黄色葡萄球菌(ATCC25923)从中国通用微生物收集中心获得。酵母提取物和胰蛋白胨购自英国ThermoScient ific公司。甲醇(分析纯)、无水乙醇(分析纯),均购于天津光复科技发展有限公司;重水(D2O)上海迈瑞尔化学技术有限公司。
仪器与设备
YC-015实验型喷雾干燥机上海雅程仪器设备有限公司;TGL-16A型高速冷冻离心机长沙平凡仪器有限公司;XW-80微型涡流混合仪上海泸西分析仪器有限公司;TS50傅立叶变换近红外光谱仪ThermoFisher公司;SU510扫描电子显微镜400MHZ核磁共振波谱仪德国布鲁克科技有限公司;高效液相色谱仪安捷伦科技有限公司
实施例1:
一种芦丁壳寡糖复合物,包括芦丁以及壳寡糖,其中,芦丁与壳寡糖的摩尔比为1:1。制备方法如下:
(1)以芦丁和壳寡糖(分子量980Da)为原料;
(2)用超纯水分别配制1mM的芦丁溶液和1mM的壳寡糖溶液,两者等体积混合,在旋涡振荡器上振荡10min;
(3)混合液在20℃,以1,000×g转速离心10min后取上清;
(4)将上清液进行喷雾干燥(进风温度100℃,1L/h),得到的成品即芦丁壳寡糖复合物;
(5)对复合物进行分子结构解析(NMR,SEM),评价复合物的抑菌性、抗氧化性、水溶性和苦味,并从分子结构层面解释功能活性和物理性质的变化机理。
实施例2:一种芦丁壳寡糖复合物,包括芦丁以及壳寡糖,其中,芦丁与壳寡糖的摩尔比为1:3。制备方法如下:
(1)以芦丁和壳寡糖(分子量980Da)为原料;
(2)用超纯水分别配制1mM的芦丁溶液和3mM的壳寡糖溶液,两者等体积混合,在旋涡振荡器上振荡5min;
(3)混合液在15℃,以1,000×g转速离心20min后取上清;
(4)将上清液进行喷雾干燥(进风温度80℃,0.5L/h),得到的成品即芦丁壳寡糖复合物;
(5)对复合物进行分子结构解析(NMR,SEM),评价复合物的抑菌性、抗氧化性、水溶性和苦味,并从分子结构层面解释功能活性和物理性质的变化机理。
实施例3:一种芦丁壳寡糖复合物,包括芦丁以及壳寡糖,其中,芦丁与壳寡糖的摩尔比为1:5。制备方法如下:
(1)以芦丁和壳寡糖(分子量980Da)为原料;
(2)用超纯水分别配制1mM的芦丁溶液和5mM的壳寡糖溶液,两者等体积混合,在旋涡振荡器上振荡30min;
(3)混合液在30℃,以1,000×g转速离心5min后取上清;
(4)将上清液进行喷雾干燥(进风温度120℃,5L/h),得到的成品即芦丁壳寡糖复合物;
(5)对复合物进行分子结构解析(NMR,SEM),评价复合物的抑菌性、抗氧化性、水溶性和苦味,并从分子结构层面解释功能活性和物理性质的变化机理。
对比例1:对比例1与实施例1的区别仅在于步骤4)中采用冷冻干燥,即将上清液在-80℃下冷冻12小时,然后冷冻干燥24小时,得到摩尔比为1:1的芦丁壳寡糖复合物。
对比例2:对比例2与实施例2的区别仅在于步骤4)中采用冷冻干燥,即将上清液在-80℃下冷冻12小时,然后冷冻干燥24小时,得到摩尔比为1:3的芦丁壳寡糖复合物。
对比例3:对比例3与实施例3的区别仅在于步骤4)中采用冷冻干燥,即将上清液在-80℃下冷冻12小时,然后冷冻干燥24小时,得到摩尔比为1:5的芦丁壳寡糖复合物。
抑菌性测定
使用大肠杆菌和金黄色葡萄球菌菌株作为测试菌株来测定芦丁,壳寡糖和芦丁壳寡糖复合物的抑菌性。在Luria-Bertani液体培养基中培养大肠杆菌和金黄色葡萄球菌,并用0.9%NaCl溶液稀释以制备适当的细菌悬浮液。根据肉汤微量稀释法测定各样品的最低抑制浓度。首先,将在37℃下培养6小时后的0.1mL细菌悬浮液加入到2mL肉汤培养基中,并以摩尔比为1:1的芦丁壳寡糖复合物处理,并进一步培养6小时。然后,菌液用0.9%NaCl溶液冲洗三次,并以5,000×g离心6分钟并用2.5%戊二醛固定12小时,之后再次用蒸馏水洗涤细胞。随后,将所得细胞用乙醇脱水。最后,将样品在无菌工作台中风干。通过扫描电镜观察芦丁壳寡糖复合物处理前后的细菌细胞形态。
DPPH清除率测定
取测定液0.5mL,加入2mL2×10-4mol/LDPPH,再加入2.5mL无水甲醇,充分混合,避光静置30min,517nm测定其吸光度A1。同时测定2mL2×10-4mol/LDPPH溶液与3mL无水甲醇混合液的吸光度A2,以及0.5mL测定液与4.5mL无水甲醇混合液的吸光度A0。按照以下公式计算DPPH清除率:
A0,空白对照的吸光度;A1,加测定液后的吸光度。
结果表示为μMTrolox当量(TE)/g样品,通过Trolox标准曲线计算。
ABTS+清除率的测定
7mmol/L的ABTS+溶液与2.45mmol/L的过硫酸钾溶液以体积比2:1混合,在室温下置于暗处反应16h,形成ABTS自由基储备液。ABTS自由基储备液使用前用无水乙醇稀释成工作液,要求稀释到在30℃,734nm波长下的吸光度为0.70±0.02。取测定液0.2mL,加入5mLABTS+工作液,充分混合,室温下反应10min,于734nm测定其吸光度A1。以无水乙醇代替测定液、ABTS工作液做空白、对照。结果表示为μMTrolox当量(TE)/g样品,通过Trolox标准曲线计算。
水溶性分析
采用高效液相色谱仪测定芦丁含量。分别将芦丁及芦丁壳寡糖复合物溶于超纯水中,涡旋振荡5min后,放入37℃得培养箱1h,以10,000r/min的转速离心10min,取上清液。色谱柱:XterraRP18Column(∮4.6mm×250mm)对样品进行分离;流动相:甲醇:水(V:V)为50:50,并用磷酸调pH至2.8;流速:0.5min;进样量:20μL;检测波长:360nm。通过对比芦丁的峰面积与相应的标准样品制备的标准曲线计算芦丁的含量。
苦味分析
将芦丁与芦丁壳寡糖复合物溶于75%乙醇溶液中,搅拌均匀后,量取相同体积的溶液进行检测。每个样品4个平行。样品检测前先进行传感器预热、清洗及参数设置,参数设置如下:最大电压:1V,最低电压:-1V,脉冲间隔:100MV,灵敏度:10-4。
扫描电镜分析
将导电胶粘于铜板上,分别取适量的芦丁、壳寡糖、芦丁壳寡糖复合物均匀涂布在导电胶上,然后用常规真空喷镀法喷金90s后,将铜板置于扫描电镜下分别对样品进行显微拍摄。结果见图4。
核磁共振氢谱分析
分别将纯芦丁、摩尔比为1:1、1:3、1:5的芦丁壳寡糖复合物,溶于D2O,采用德国-瑞士Bruker400MHZ核磁共振波谱仪分析芦丁及其复合物的1H-NMR。核磁共振光谱获得的单脉冲序列参数设置如下:取样时间2.18s,扫描次数16次、延迟时间15s,采样温度为25℃,其他参数为仪器内设值。结果见图5。ROESY谱参数设置如下:混合时间0.25s;X偏移量,4.7ppm;X点,1024;Y点,256;扫描次数,48次;豫驰时间,1.5s。
表1为芦丁与壳寡糖的摩尔比分别为1:1,1:3,1:5的芦丁壳寡糖复合物最低抑菌浓度比较。
表1
抑菌分析
表1显示摩尔比为1:1和1:3的芦丁壳寡糖复合物的最低抑菌浓度均低于芦丁和壳寡糖的最低抑菌浓度,而且对以金黄色葡萄球菌为代表的革兰氏阳性菌表现出了更强的抑菌性。其中,摩尔比为1:1的芦丁壳寡糖复合物的最低抑菌浓度最低,仅为芦丁的1/4。这可能是因为摩尔比为1:1的芦丁壳寡糖复合物拥有更平滑的表面和更小尺寸,更容易结合并破坏细菌细胞膜。此外,由于芦丁表现出比壳寡糖更强的抗菌性能,所以也可能是摩尔比为1:1的芦丁壳寡糖复合物由于相对较高的芦丁含量导致其抑菌性较强。结合芦丁壳寡糖复合物处理前后的细菌扫描电镜图(图1示出)对其抑菌机理进行分析得知,经过芦丁壳寡糖复合物处理后的大肠杆菌和金黄色葡萄球菌均表现出表面皱缩甚至出现破损现象。由此推测,芦丁壳寡糖复合物是通过与细菌细胞膜接触从而造成细菌细胞破损并使细菌失去活性。
表2为实施例1-3喷雾干燥以及对比例1-3冷冻干燥下芦丁与壳寡糖的摩尔比分别为1:1,1:3,1:5的芦丁壳寡糖复合物抗氧化活性比较。
表2
抗氧化分析
芦丁具有良好的抗氧化能力,为了研究芦丁壳寡糖复合物对自由基的清除能力,我们对不同摩尔比例的复合物进行了DPPH、ABTS+自由基清除能力的分析。结果如表1所示,芦丁壳寡糖复合物对DPPH和ABTS+的清除率都有显著提高,并随着壳寡糖添加量的增加,复合物对自由基清除能力有所提高。有研究表明,黄酮类化合物的抗氧化能力与其结构有直接关系,芦丁的抗氧化能力高并且与其在A和C环中提供儿茶酚样结构的5-OH和4-keto的类黄酮结构相关,这说明,芦丁壳寡糖复合物中芦丁的结合位点A环发生的结构变化使得复合物抗氧化能力有所提高。
ABTS实验结果表明,喷雾干燥的芦丁-壳寡糖复合物的抗氧化活性明显优于游离芦丁(p<0.05)。同时,冷冻干燥芦丁-壳寡糖复合物也显示ABTS自由基清除特性显著增加,然而,DPPH自由基清除活性与游离芦丁相比无统计学差异。根据两种制备方法制得样品的水溶性差异可知,喷雾干燥的芦丁-壳寡糖复合物抗氧化性优于冷冻干燥的芦丁-壳寡糖的原因可能是相同摩尔比时,喷雾干燥的芦丁-壳寡糖复合物中具有更强抗氧化生物活性的芦丁的水溶性更好。
图2为实施例喷雾干燥芦丁与摩尔比分别为1:1,1:3,1:5的芦丁壳寡糖复合物以及对比例冷冻干燥的水溶性对比图。将壳寡糖加入芦丁中大大增加了芦丁在水中的溶解度(复合物1:1、1:3、1:5中芦丁溶解度分别是纯芦丁的4.52倍、5.44倍、5.83倍),并且随着壳寡糖比例的增大,芦丁的溶解度也显著性增大。如图4所示,与芦丁特有的针状晶体结构相比,芦丁壳寡糖复合物的外表更加光滑且粒径更小,所以芦丁溶解度增大的一个主要原因是由于壳寡糖的加入打乱了芦丁原有的疏水结晶结构。而NMR结果表明,芦丁的疏水芳香单元与壳寡糖络合,是导致芦丁的水溶性增强的另一个原因。与游离芦丁相比,冷冻干燥后制得的摩尔比为1:5的芦丁-壳寡糖水溶性显著增加(p<0.05),是游离芦丁水溶性的1.17倍。而冷冻干燥后制得的摩尔比为1:1和1:3的芦丁-壳寡糖相较于游离芦丁水溶性没有显著提升。由图可知,喷雾干燥制得的芦丁-壳寡糖复合物水溶性明显优于冷冻干燥制得的芦丁-壳寡糖复合物水溶性,这说明喷雾干燥法对制备稳定且水溶性良好的芦丁-壳寡糖复合物更有效。
图3中,同一个样品在主成分分析图上前2个主成分的贡献率分别为:80.33%,11.88%,累计贡献率为92.21%,因此取前2个主成分对应的特征向量所决定的两维子空间能够充分保存原始数据的信息。每一个样品的4个点离散度较小,而不同样品之间没有互相干扰,存在一定的差异,说明该电子舌可以很好的区分不同的样品。从图3中两点之间的距离的长短可以很明显的看出,RC5的降苦效果最好(RC5与R的距离最长)。
由图3可知,随着壳寡糖的加入,喷雾干燥与冷冻干燥制得的芦丁-壳寡糖复合物与游离芦丁的距离均明显增加(p<0.05),这说明,两种方法对于芦丁降苦都有明显作用。摩尔比为1:5时的冷冻干燥芦丁-壳寡糖复合物与游离芦丁的距离为31.60,略小于相同摩尔比时喷雾干燥芦丁-壳寡糖复合物与游离芦丁的距离(32.65)。且喷雾干燥的芦丁-壳寡糖样品四次平行实验的重复性更好,这说明喷雾干燥法对制备稳定均一且苦味降低的芦丁-壳寡糖复合物更有效。
图4为各样品的扫描电镜图,放大倍数均为800倍。从图4中可以发现,芦丁呈现不规则的针状结构,壳寡糖颗粒呈球状结构,而芦丁壳寡糖复合物均呈明显的片状结构,其形态与芦丁、壳寡糖的电镜外观相比发生了非常显著的变化。说明在喷雾干燥的过程中,芦丁壳寡糖相互结合成新的物质。
图5中,随着复合物中壳寡糖摩尔比的增加,芦丁中质子H6(0.013–0.113ppm),H5’(0.01–0.14ppm),H8(0.014–0.145ppm),H6’(0.005–0.149ppm)的化学位移变化值Δδ也在增大,这是由于芦丁和壳寡糖分子之间的相互靠近改变了芦丁质子在磁场中的环境而引起的。从Δδ值可推断,芦丁中H6,H8所在的A环和H5’,6’所在的B环与壳寡糖分子相互靠近。ROESY图(图6)也清晰反映出芦丁中A、B环上的质子可能位于壳寡糖的糖质子附近,推测二者通过氢键维持复合物的稳定构想。
以上内容仅为本发明的较佳实施例,对于本领域的普通技术人员,依据本发明的思想,在具体实施方式及应用范围上均会有改变之处,本说明书内容不应理解为对本发明的限制。
Claims (1)
1.一种芦丁壳寡糖复合物的制备方法,其特征在于,具体步骤如下:
⑴分别配制芦丁水溶液、壳寡糖水溶液,将两者混合,在振荡器上振荡5-30min;所述的芦丁与壳寡糖的摩尔比为1:1;所述的壳寡糖的分子量为980Da;
⑵混合液在15-30℃,以1,000×g离心5-20min后取上清;
⑶将上清液在80-120℃、0.5-5L/h的条件下进行喷雾干燥,得到芦丁壳寡糖复合物。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811222615.3A CN109430878B (zh) | 2018-10-19 | 2018-10-19 | 芦丁壳寡糖复合物及其制备方法和应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811222615.3A CN109430878B (zh) | 2018-10-19 | 2018-10-19 | 芦丁壳寡糖复合物及其制备方法和应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN109430878A CN109430878A (zh) | 2019-03-08 |
CN109430878B true CN109430878B (zh) | 2022-04-05 |
Family
ID=65546961
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201811222615.3A Active CN109430878B (zh) | 2018-10-19 | 2018-10-19 | 芦丁壳寡糖复合物及其制备方法和应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN109430878B (zh) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109924336A (zh) * | 2019-04-04 | 2019-06-25 | 维乐维健康产业有限公司 | 一种高吸收叶黄素酯玉米黄质软糖的制备方法 |
JP7486943B2 (ja) * | 2019-12-16 | 2024-05-20 | ロレアル | カチオン性多糖とアニオン性抗酸化剤とを含む組成物 |
CN111011468A (zh) * | 2019-12-19 | 2020-04-17 | 浙江海洋大学 | 一种琼胶寡糖-没食子酸共价复合物的制备及应用 |
CN111771968A (zh) * | 2020-03-09 | 2020-10-16 | 天津科技大学 | 百里香酚-壳寡糖复合物及其制备方法和应用 |
CN113105569B (zh) * | 2021-03-31 | 2022-07-15 | 西南大学 | 柚皮苷-壳寡糖偶联物及其制备方法和应用 |
CN114521649A (zh) * | 2022-01-25 | 2022-05-24 | 天津科技大学 | 多酚壳寡糖复合物及其制备方法和应用 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1651465A (zh) * | 2004-02-04 | 2005-08-10 | 陈建操 | 糖基修饰改性膳食纤维及其制备方法和应用 |
CN102174123A (zh) * | 2011-02-25 | 2011-09-07 | 重庆大学 | 一种水溶性黄酮-壳聚糖衍生物的生产方法 |
CN104587260A (zh) * | 2015-01-28 | 2015-05-06 | 福州乾正药业有限公司 | 竹叶黄酮和壳寡糖的组合物,其制备方法和应用 |
CN105145574A (zh) * | 2015-10-19 | 2015-12-16 | 高大元 | 一种盐角草芦丁抑藻剂的制备方法 |
CN105166862A (zh) * | 2015-08-12 | 2015-12-23 | 天津科技大学 | 高稳定性纤维素基天然食用花青素色素复合物的制备方法 |
CN107568737A (zh) * | 2017-08-07 | 2018-01-12 | 天津科技大学 | 利用壳寡糖改善橙皮苷水溶性和抗氧化性的方法 |
-
2018
- 2018-10-19 CN CN201811222615.3A patent/CN109430878B/zh active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1651465A (zh) * | 2004-02-04 | 2005-08-10 | 陈建操 | 糖基修饰改性膳食纤维及其制备方法和应用 |
CN102174123A (zh) * | 2011-02-25 | 2011-09-07 | 重庆大学 | 一种水溶性黄酮-壳聚糖衍生物的生产方法 |
CN104587260A (zh) * | 2015-01-28 | 2015-05-06 | 福州乾正药业有限公司 | 竹叶黄酮和壳寡糖的组合物,其制备方法和应用 |
CN105166862A (zh) * | 2015-08-12 | 2015-12-23 | 天津科技大学 | 高稳定性纤维素基天然食用花青素色素复合物的制备方法 |
CN105145574A (zh) * | 2015-10-19 | 2015-12-16 | 高大元 | 一种盐角草芦丁抑藻剂的制备方法 |
CN107568737A (zh) * | 2017-08-07 | 2018-01-12 | 天津科技大学 | 利用壳寡糖改善橙皮苷水溶性和抗氧化性的方法 |
Non-Patent Citations (1)
Title |
---|
rutin-loaded chitosan microspheres:Characterization and evaluation of the anti-inflamatory activity;Donato Cosco et.al;《Carbohydrate Polymers》;20160611(第152期);参见第584页左栏倒数第2段至右栏第1段 * |
Also Published As
Publication number | Publication date |
---|---|
CN109430878A (zh) | 2019-03-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN109430878B (zh) | 芦丁壳寡糖复合物及其制备方法和应用 | |
Su et al. | Structural characterization and antioxidant activity of polysaccharide from four auriculariales | |
Shen et al. | Structural characterization and immunomodulatory activity of novel polysaccharides from Citrus aurantium Linn. variant amara Engl | |
Yang et al. | Structural characterization and evaluation of the antioxidant activities of polysaccharides extracted from Qingzhuan brick tea | |
Shang et al. | Structure characterization of an exopolysaccharide produced by Bifidobacterium animalis RH | |
Ma et al. | Alpinetin/hydroxypropyl-β-cyclodextrin host–guest system: Preparation, characterization, inclusion mode, solubilization and stability | |
Zhang et al. | Preparation, characterization and antioxidant activity evaluation in vitro of Fritillaria ussuriensis polysaccharide-zinc complex | |
Li et al. | Rapid screening and identification of α-amylase inhibitors from Garcinia xanthochymus using enzyme-immobilized magnetic nanoparticles coupled with HPLC and MS | |
Wei et al. | Composition and bioactivity of polysaccharides from tea seeds obtained by water extraction | |
CN106978160B (zh) | 氮硫掺杂碳纳米荧光探针绿色制备方法 | |
Chen et al. | Optimization of polysaccharide extraction process from grifola frondosa and its antioxidant and anti-tumor research | |
Yadav et al. | Novel chitosan derivatives of 2-imidazolecarboxaldehyde and 2-thiophenecarboxaldehyde and their antibacterial activity | |
CN107568737A (zh) | 利用壳寡糖改善橙皮苷水溶性和抗氧化性的方法 | |
Dalonso et al. | Characterization and antineoplasic effect of extracts obtained from Pleurotus sajor-caju fruiting bodies | |
Zhou et al. | Extraction, structure characterization and biological activity of polysaccharide from coconut peel | |
Zhang et al. | Structural characterization and biological activities of a new polysaccharide isolated from Morchella Sextelata | |
Lan et al. | Metabolomic analysis of antimicrobial mechanism of polysaccharides from Sparassis crispa based on HPLC-Q-TOF/MS | |
Tu et al. | A novel polysaccharide from Hericium erinaceus: Preparation, structural characteristics, thermal stabilities, and antioxidant activities in vitro | |
da Silva et al. | NMR studies of inclusion complexation of the pyrrolizidine alkaloid retronecine and p-sulfonic acid calix [6] arene | |
Chang et al. | Effect of pectin on epsilon-polylysine purification: Study on preparation, physicochemical property, and bioactivity of pectin-epsilon-polylysine complex | |
Li et al. | Structural and biological properties of water soluble polysaccharides from lotus leaves: Effects of drying techniques | |
CN102000133B (zh) | 一种中药抗氧化制剂的制备方法 | |
Arumugam et al. | Biogenesis of silver nanoparticles using selected plant leaf extract; characterization and comparative analysis of their antimicrobial activity. | |
CN109439712A (zh) | 一种豌豆低聚肽硒及其制备方法和应用 | |
Huang et al. | The effect of spray drying on sucrose–glycine caramel powder preparation |
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 |