CN102321186A - 一种羧甲基化黑木耳多糖、粗多糖及其制备方法和应用 - Google Patents
一种羧甲基化黑木耳多糖、粗多糖及其制备方法和应用 Download PDFInfo
- Publication number
- CN102321186A CN102321186A CN201110219047A CN201110219047A CN102321186A CN 102321186 A CN102321186 A CN 102321186A CN 201110219047 A CN201110219047 A CN 201110219047A CN 201110219047 A CN201110219047 A CN 201110219047A CN 102321186 A CN102321186 A CN 102321186A
- Authority
- CN
- China
- Prior art keywords
- carboxymethylation
- polysaccharide
- black fungus
- crude polysaccharides
- fungus crude
- 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
- 150000004676 glycans Chemical class 0.000 title claims abstract description 97
- 229920001282 polysaccharide Polymers 0.000 title claims abstract description 97
- 239000005017 polysaccharide Substances 0.000 title claims abstract description 97
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 235000000023 Auricularia auricula Nutrition 0.000 title abstract 9
- 241001149430 Auricularia auricula-judae Species 0.000 title abstract 9
- 235000013376 functional food Nutrition 0.000 claims abstract description 5
- 238000006467 substitution reaction Methods 0.000 claims abstract description 5
- 241000221377 Auricularia Species 0.000 claims description 55
- 241000233866 Fungi Species 0.000 claims description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- 239000007788 liquid Substances 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 17
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 239000006228 supernatant Substances 0.000 claims description 11
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 10
- 238000000502 dialysis Methods 0.000 claims description 10
- 238000010828 elution Methods 0.000 claims description 10
- 238000001556 precipitation Methods 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000011780 sodium chloride Substances 0.000 claims description 8
- WQZGKKKJIJFFOK-PQMKYFCFSA-N alpha-D-mannose Chemical compound OC[C@H]1O[C@H](O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-PQMKYFCFSA-N 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 238000004108 freeze drying Methods 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- -1 through dialysis Substances 0.000 claims description 5
- 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 4
- 229920005654 Sephadex Polymers 0.000 claims description 4
- 239000012507 Sephadex™ Substances 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 230000008021 deposition Effects 0.000 claims description 4
- 239000008103 glucose Substances 0.000 claims description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- LPQOADBMXVRBNX-UHFFFAOYSA-N ac1ldcw0 Chemical compound Cl.C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN3CCSC1=C32 LPQOADBMXVRBNX-UHFFFAOYSA-N 0.000 claims description 3
- 150000001720 carbohydrates Chemical group 0.000 claims description 3
- 239000012141 concentrate Substances 0.000 claims description 3
- AZHSSKPUVBVXLK-UHFFFAOYSA-N ethane-1,1-diol Chemical compound CC(O)O AZHSSKPUVBVXLK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 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 2
- 238000005342 ion exchange Methods 0.000 claims description 2
- 230000004048 modification Effects 0.000 abstract description 17
- 238000012986 modification Methods 0.000 abstract description 17
- 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 abstract description 9
- 230000003078 antioxidant effect Effects 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 7
- 238000002474 experimental method Methods 0.000 abstract description 7
- 239000003963 antioxidant agent Substances 0.000 abstract 2
- 235000006708 antioxidants Nutrition 0.000 abstract 1
- 239000002778 food additive Substances 0.000 abstract 1
- 235000013373 food additive Nutrition 0.000 abstract 1
- 238000000338 in vitro Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 30
- 239000000523 sample Substances 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000009471 action Effects 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 230000002000 scavenging effect Effects 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- 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 5
- 239000000843 powder Substances 0.000 description 5
- 238000002835 absorbance Methods 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000012488 sample solution Substances 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229920002444 Exopolysaccharide Polymers 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 206010010774 Constipation Diseases 0.000 description 2
- 229920002307 Dextran Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- MGJZITXUQXWAKY-UHFFFAOYSA-N diphenyl-(2,4,6-trinitrophenyl)iminoazanium Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1N=[N+](C=1C=CC=CC=1)C1=CC=CC=C1 MGJZITXUQXWAKY-UHFFFAOYSA-N 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 230000000050 nutritive effect Effects 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- OQUKIQWCVTZJAF-UHFFFAOYSA-N phenol;sulfuric acid Chemical compound OS(O)(=O)=O.OC1=CC=CC=C1 OQUKIQWCVTZJAF-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 229960004249 sodium acetate Drugs 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 241000437273 Auricularia cornea Species 0.000 description 1
- 241000221454 Auriculariaceae Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- 241000201295 Euphrasia Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 1
- 108010002350 Interleukin-2 Proteins 0.000 description 1
- 244000207740 Lemna minor Species 0.000 description 1
- 235000006439 Lemna minor Nutrition 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 241000221365 Tremellales Species 0.000 description 1
- 206010046788 Uterine haemorrhage Diseases 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- SQBJBZVNGGZASY-UHFFFAOYSA-N [Na].ClS(=O)(=O)O Chemical compound [Na].ClS(=O)(=O)O SQBJBZVNGGZASY-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- SRBFZHDQGSBBOR-LECHCGJUSA-N alpha-D-xylose Chemical compound O[C@@H]1CO[C@H](O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-LECHCGJUSA-N 0.000 description 1
- SRBFZHDQGSBBOR-QMKXCQHVSA-N alpha-L-arabinopyranose Chemical compound O[C@H]1CO[C@@H](O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-QMKXCQHVSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000010100 anticoagulation Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 244000285940 beete Species 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- CUBCNYWQJHBXIY-UHFFFAOYSA-N benzoic acid;2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1O CUBCNYWQJHBXIY-UHFFFAOYSA-N 0.000 description 1
- 230000008827 biological function Effects 0.000 description 1
- 230000008512 biological response Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 235000011222 chang cao shi Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 208000014617 hemorrhoid Diseases 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
- 229960000367 inositol Drugs 0.000 description 1
- SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 208000030208 low-grade fever Diseases 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 235000008935 nutritious Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000004223 radioprotective effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 235000003563 vegetarian diet Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 229960003487 xylose Drugs 0.000 description 1
Images
Landscapes
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明公开了一种羧甲基化黑木耳多糖、粗多糖及其制备方法和应用,属于多糖改性技术领域。该羧甲基化黑木耳粗多糖的取代度为0.857,溶解度为0.6mg/ml;羧甲基化黑木耳多糖的溶解度为26mg/ml,分子量为3.4×106Da。本发明的羧甲基化黑木耳粗多糖和羧甲基化黑木耳多糖的体外抗氧化实验表明,该多糖与未羧甲基化黑木耳多糖相比,在DPPH自由基、羟自由基、ABTS+自由基的清除作用方面有显著的提高,并且其溶解性显著提高,可作为抗氧化剂,用作功能食品和食品添加剂。
Description
技术领域
本发明涉及一种羧甲基化黑木耳多糖及其制备方法和它的应用,属于多糖改性技术领域。
背景技术
黑木耳(Auricularia auricular(L.ex Hook)Underw)又名木蛾、树鸡、云耳、耳子等,属真菌类担子菌纲,银耳目,木耳科,木耳属,广泛分布于北半球温带地区的东北亚,尤其是我国东北地区。黑木耳不仅味道鲜美,而且营养丰富,经全面营养成分分析表明,黑木耳含有丰富的蛋白质、多种氨基酸、纤维素、维生素及矿物质等(吴宪瑞.黑木耳的质量标准及其营养成分.中国林副特产,1996,36(1):21-22.),有着“素中之肉”、“素食之王”的美称,是一种营养价值极高的黑色滋补食品,得到世界广泛的公认(张润光,刁小琴,关海宁.黑木耳营养保健功能及其产品开发.保鲜与加工,2010,10(1):54-56.)。传统中医认为,黑木耳性味甘平,具有清肺润肠、滋阴补血、活血化瘀、明目养胃等功效,对崩漏、痔疮、血痢、贫血及便秘等症状有效。现代药理学研究表明,黑木耳的生物活性主要来自其多糖成分,黑木耳多糖作为“生物应答效应物”,具有抗凝血、抗肿瘤、抗炎症等细胞保护作用,还具有降低血脂、血糖、血液粘度、胆固醇以及抗糖尿病、抗衰老、抗辐射等多种生物功能(黄贤刚,全永亮,管斌,胡勇.黑木耳多糖研究进展.粮油食品科技,2010,18(1):47-54.)。但研究发现,黑木耳中性多糖由于其溶解性差,极大的限制了其进一步的研究和在食品、药品开发中的应用。
分子修饰是通过化学、物理学及生物学等手段对化合物分子进行结构改造,以获得不同结构类型衍生物的方法。对多糖进行分子修饰,有利于改变多糖的结构,改善多糖的溶解性,增强天然多糖的生物活性或使多糖产生新的活性,还可降低多糖类药物的毒副作用,从而有利于多糖类药物的开发与应用。多糖分子修饰的方法主要有硫酸化修饰、磷酸化修饰、乙酰化修饰、烷基化修饰、磺酰化修饰、羧甲基化修饰等(张难,吴远根,莫莉萍,张永凤,邱树毅,王文平.多糖的分子修饰研究进展.贵州科学,2008,26(3):66-71.)。羧甲基化作为一种常用的修饰方法,已成为人们关注的焦点。2010年,吴广枫,李平兰等申请的专利“一种所佳话双歧杆菌胞外多糖及其制备方法和应用”(申请号:201001248295.6),将胞外多糖与氯乙酸在碱溶液中反应得到羧甲基双歧杆菌胞外多糖,并证明该多糖可以显著提高小鼠脾细胞中IL-2、IFNγ细胞因子水平,免疫调节力显著高于未改性的双歧杆菌胞外多糖。2005年,郭祀远等申请的专利“羧甲基裂褶多糖制备方法及在化妆品和抗肿瘤药物中应用”(申请号:200510101678.X),发现羧甲基化多糖的溶解性得到显著改善,并且保持良好的流变性能和抗肿瘤活性。本发明人对黑木耳多糖进行羧甲基化,确定其结构特征,比较研究了羧甲基化前后多糖的溶解性和抗氧化活性。有关黑木耳多糖羧甲基化衍生物的制备和抗氧化活性研究至今未见国内外文献报道,也未见相应专利公开。
发明内容
为了克服上述现有技术中的不足,本发明提供一种羧甲基化黑木耳多糖及其制备方法和应用。
一、本发明的第一个目的在于提供一种羧甲基化黑木耳粗多糖和羧甲基化黑木耳多糖。
一种羧甲基化黑木耳粗多糖(CMAAP),其多糖得率为61.36%;羧甲基化取代度为0.857;溶解度为0.6 mg/mL。
一种羧甲基化黑木耳多糖(CMAAP22),该多糖分子量为3.4×106 Da;单糖组成为:甘露糖(man) : 葡萄糖(glu) = 1.06 : 1;该多糖以β-(1→3)-D- man为主链,glu以取代基的形式键和于甘露糖的O-2和O-6位,糖残基的C-2, C-4 和C-6位由–CH2COOH部分取代;该多糖溶解度为26 mg/mL。
本发明的第二个目的在于提供上述羧甲基化黑木耳粗多糖和羧甲基化黑木耳多糖的制备方法,按照下述步骤进行:
⑴ 黑木耳多糖的提取方法:
以料液比1:50-1:70(m/v),在温度80-100℃水中提取2-4h,提取2次,合并上清液,上清液经浓缩后,加入乙醇醇沉,使得多糖的浓缩液中乙醇浓度为60-85%(v/v),所得沉淀离心、经冷冻干燥24-48h后得黑木耳粗多糖(AAP);
⑵ 羧甲基化黑木耳多糖的制备:
取上述传统水提醇沉所得黑木耳粗多糖,以料液比1:40(m/v)加入异丙醇,室温剧烈搅拌15min;在上述溶液中按照体积比40:7的比例逐滴加入质量浓度为20% 氢氧化钠溶液,室温下搅拌反应一定时间;再按照黑木耳粗多糖与氯乙酸质量比1:0.5-1.5的比例加入氯乙酸,于20-60℃恒温水浴锅中反应2-4 h;反应液用稀盐酸中和至中性,经透析、浓缩和醇沉后即得羧甲基化黑木耳粗多糖(CMAAP);
⑶ 取羧甲基化黑木耳粗多糖,用适量水溶解,离心除去不溶物,上清液通过DEAE-52离子交换柱进行分离;逐步以0-1 mol/L的NaCl溶液洗脱,用硫酸-苯酚法绘制洗脱曲线,根据洗脱曲线分别收取合并洗脱液,其中0.1mol/L NaCl的洗脱液经浓缩、透析后,上葡聚糖凝胶柱,以0.1 mol/L NaCl洗脱,根据洗脱曲线收取合并洗脱液,经浓缩、透析、冻干得羧甲基化黑木耳多糖(CMAAP22)。
三、本发明的第三个目的在于提供羧甲基化黑木耳粗多糖和羧甲基化黑木耳多糖作为抗氧化剂在功能食品和食品添加剂中的应用。
该发明的优点是:(1)本发明采用分子修饰的方法制备出羧甲基化黑木耳粗多糖和羧甲基化黑木耳多糖;(2)本发明的羧甲基化黑木耳粗多糖和羧甲基化黑木耳多糖的溶解性好,其溶解度分别是未羧甲基化黑木耳多糖的6倍和260倍;(3)本发明的羧甲基化黑木耳粗多糖和羧甲基化黑木耳多糖的抗氧化活性显著提高,可作为抗氧化剂,应用于功能食品和食品添加剂。
附图说明
图1 是羧甲基黑木耳多糖的13C-NMR谱图;
图2 是对·OH的清除率;
图3 是对DPPH·的清除率;
图4 是对ABTS+的清除率。
具体实施方式
实施例1
称取100g黑木耳粉末,置于圆底烧瓶中,按料液比1:50、浸提时间2h、浸提温度80℃,在热水浴中回流浸提2次,冷却后离心,合并上清液;上述清液经减压浓缩,加入4倍体积95%乙醇进行沉淀,所得沉淀经离心、冷冻干燥后得粗多糖(AAP)样品粉末。黑木耳多糖得率为20.52%。取黑木耳粗多糖样品1.0g溶于40mL异丙醇中,室温下剧烈搅拌15min后,将7mL的20%的NaOH逐滴加入上述搅拌液中,室温下搅拌反应1h,再将0.5g氯乙酸溶于少量蒸馏水中,慢慢加入上述反应液中,反应混合液置于20℃恒温水浴锅中反应2h,待冷却至室温,反应产物用稀盐酸中和至pH为7,流水透析24h,蒸馏水透析48h后,浓缩至一定体积,用4倍95%乙醇在4℃下沉淀12h,冷冻干燥得羧甲基化黑木耳粗多糖(CMAAP)。所得羧甲基化黑木耳粗多糖的得率为39.75%。
实施例2
称取100g黑木耳粉末,置于圆底烧瓶中,按料液比1:60、浸提时间3h、浸提温度90℃,在热水浴中回流浸提2次,其余步骤同实例1中黑木耳粗多糖的提取方法,得黑木耳多糖得率为27.23%。取黑木耳粗多糖样品1.0g溶于40mL异丙醇中,室温下剧烈搅拌15min后,将7mL的20%的NaOH逐滴加入上述搅拌液中,室温下搅拌反应1h,再将1.0g氯乙酸溶于少量蒸馏水中,慢慢加入上述反应液中,反应混合液置于40℃恒温水浴锅中反应3h,其余步骤同实例1中羧甲基化黑木耳粗多糖的制备方法,得羧甲基化黑木耳粗多糖的得率为54.69%。
实施例3
称取100g黑木耳粉末,置于圆底烧瓶中,按料液比1:70、浸提时间4h、浸提温度100℃、在热水浴中回流浸提2次,其余步骤同实例1中黑木耳粗多糖的提取方法,得黑木耳多糖得率为32.24%。取黑木耳粗多糖样品1.0g溶于40mL异丙醇中,室温下剧烈搅拌15min后,将7mL的20%的NaOH逐滴加入上述搅拌液中,室温下搅拌反应1h,再将1.5g氯乙酸溶于少量蒸馏水中,慢慢加入上述反应液中,反应混合液置于60℃恒温水浴锅中反应4h,其余步骤同实例1中羧甲基化黑木耳粗多糖的制备方法,得羧甲基化黑木耳粗多糖的得率为61.36%。
实施例4 羧甲基化黑木耳多糖的制备:
步骤一、羧甲基化黑木耳粗多糖的纯化
1、实验材料
1.1药品与试剂
黑木耳粗多糖;
DEAE-52纤维素交换树脂,英国Whatman公司;
sephadex G-100,英国Whatman公司。
Dextran T-10,T-40,T-70,T-500,T-2000和Blue Dextran T-2000,Pharmacia公司。
1.2仪器
UV-7502 PC可见分光光度计,上海茂欣仪器有限公司
层析柱 :1.6cm×50cm, 上海沪西分析仪器厂有限公司
DHL-A电脑恒流泵,上海沪西分析仪器厂有限公司
DBS-100电脑自动分部收集器,上海沪西分析仪器厂有限公司
2、实验方法
称取上述实施例1-3中制备的并经透析、浓缩和醇沉后的羧甲基化黑木耳粗多糖150mg,溶于10mL蒸馏水中,充分溶解后离心,将上清液滴加到DEAE-52层析柱中,0-1.0mol/L的NaCl水溶液进行洗脱,使用DHL-A恒流泵,控制流速1mL/min,用自动分部收集器收集。6min收集一管,每管收集6mL,收集液每管用苯酚-硫酸法跟踪检测,以蒸馏水为空白,于490nm的波长下测定吸光度,直到不再有糖检出。根据洗脱曲线,合并各洗脱峰的洗脱液,其中0.1mol/L NaCl的洗脱液用蒸馏水透析72h,减压浓缩,冻干,上述步骤所得多糖组分上葡聚糖凝胶柱,用0.1 mol/LNaCl溶液洗脱,使用DHL-A恒流泵,控制流速0.3mL/min,用分部自动收集器收集,每管收集3mL,收集液每管用苯酚-硫酸法跟踪检测,以蒸馏水为空白,于490nm的波长下测定吸光度,直到不再有糖检出。绘制洗脱曲线,合并洗脱峰的洗脱液,用蒸馏水透析72h,减压浓缩,冻干得到羧甲基化黑木耳多糖组分(CMAAP22)。
3、实验结果
得到羧甲基化黑木耳多糖组分(CMAAP22)。
步骤二、羧甲基化黑木耳粗多糖和羧甲基化黑木耳多糖的物化性质及结构特征
1、实验材料
1.1药品与试剂
黑木耳多糖;氯化钠、硫酸、三氯乙酸、苯酚、氢氧化钠、盐酸、醋酸钠、盐酸羟胺、肌醇、吡啶、醋酸酐、葡萄糖、鼠李糖、木糖、阿拉伯糖、甘露糖、高碘酸钠、刚果红等均为分析纯。
1.2仪器
LC-10AVP高效液相色谱系统,日本岛津
TSK-GEL G4000PW (7.5×300mm),TOSOH公司
预柱 :TSK-GUARD COLUMN PWH(7.5×75mm),TOSOH公司
ALPHA2-4冷冻干燥设备,德国CHRIST公司
PHS-2C型酸度计,上海分析仪器厂
R-200型旋转蒸发器,瑞士Büchi公司
GC 2010气相色谱系统,日本岛津
RTS-5气相毛细管柱,(30m×0.32 mm)
NEXUS 670智能型傅立叶红外光谱仪,美国尼高利公司
核磁共振仪,Braker
2、实验方法
2.1溶解度的测定
根据2005版药典进行测定。
2.2 羧甲基度测定
准确称取10mg羧甲基化黑木耳多糖放入100mL烧杯中,加入4 mL0.2mol/L的盐酸溶液(70%的甲醇溶液配制),搅拌反应3h。用80%的甲醇溶液洗涤固体至溶液中无Cl-为止。样品用0.01mol/L的NaOH标准溶液溶解,微热条件下使溶液呈透明后,立即用0.01mol/L标准盐酸溶液反滴定,取代度按下式计算:
B=(CNaOH×VNaOH-CHCl×VHCl)/W
DS=0.162B/(1-0.058B)
W为样品质量(g),B为每克样品消耗的NaOH的毫摩尔数(mmol/g)。
2.3分子量的测定
按照多糖的常规方法,以分子量已知的T-10,T-40,T-70,T-500和T-2000为标准,LC-10AVP岛津高效液相色谱系统,色谱柱为TSK-GEL G4000PW (7.5×300mm),流动相为0.003mol/L的醋酸钠溶液,流速0.8mL/min;检测器SHIMADZU RID-10A,温度25℃。多糖溶液过0.45μm的滤膜,进样10μL。
2.4单糖组成分析
精密称取多糖样品5mg于安瓿瓶中,用2mol/L的硫酸溶液溶解,封口,100℃烘箱中加热水解8h后,水解液加碳酸钡中和至中性,以4000 r/min离心除去BaSO4沉淀,上清液冷冻干燥。水解产物经乙酰化后用岛津GC 2010气相色谱系统分析。
2.5 IR测定
取1mg经干燥的多糖样品,与100~200mg经干燥的KBr粉末在玛瑙研钵中轻轻研磨均匀(在红外灯下操作)。经压片机压成薄片,于NEXUS 670智能型傅立叶红外光谱仪测定获得红外光谱图。
2.6 NMR测定
取多糖样品20mg经D2O交换3次后,溶于0.5mLD2O中,用BRUKER400型核磁共振仪,13C-NMR(100MHz,温度673.2K)(参见图1)。
3、实验结果
黑木耳粗多糖溶解度为0.1 mg/mL,羧甲基化黑木耳粗多糖溶解度为0.6 mg/mL,羧甲基黑木耳多糖溶解度为26 mg/mL。羧甲基化黑木耳多糖(CMAAP)的得率为61.36%;所得羧甲基化黑木耳多糖的羧甲基化取代度为0.857。CMAAP22分子量为3.4×106 Da。CMAAP22由甘露糖和葡萄糖组成,其摩尔比分别为1.06︰1。黑木耳多糖经羧甲基化后的多糖于1600 cm-1、1420cm-1处均出现强吸收峰,(为-COO-的特征吸收峰,其中1600 cm-1左右处为-C-O-的非对称伸缩振动吸收峰,1420cm-1左右处为-C-O-的对称伸缩振动吸收峰),表明已羧甲基化。图1为羧甲基黑木耳多糖的13C-NMR谱图,该多糖以β-(1→3)-D- man为主链,glu以取代基的形式键和于甘露糖的O-2和O-6位,糖残基的C-2, C-4 和C-6位由–CH2COOH部分取代,这种取代是非选择性的。
试验一 羧甲基化黑木耳粗多糖和羧甲基化黑木耳多糖的抗氧化作用
1、实验材料
1.1药品与试剂
黑木耳多糖:配制成生药浓度2 mg/mL的水溶液备用;
DPPH溶液:配制成0.2 mmol/L的无水乙醇溶液;
邻二氮菲溶液:配制成0.75 mmol/L的无水乙醇溶液;
磷酸盐缓冲溶液:配制成0.2 mmol/L pH7.40的缓冲溶液;
硫酸亚铁溶液:配制成0.75 mmol/L的无水乙醇溶液;
双氧水:配置成0.01%的双氧水;
ABTS + 溶液:配制成0.2 mmol/L的溶液;
1.2仪器
TU-1800紫外可见分光光度计:北京普析通用仪器有限责任公司;
BS124S电子天平:北京赛多利斯仪器系统有限公司;
冷冻干燥机FD-1C-50:北京博医康实验仪器有限公司;
旋转蒸发器RE-52C:巩义市予华仪器有限责任公司;
2、实验方法
2.1黑木耳多糖清除OH自由基作用
将多糖样品配置成不同浓度的溶液。吸取6mmol/L FeSO4溶液2mL,加入2mL样品溶液,再加入6mmol/LH2O2溶液2mL,摇匀,静置10min,再加入6mmol/L 的水杨酸溶液2mL,摇匀,静置30min,于510nm处测定吸光度值(Ai),以蒸馏水代替水杨酸测得吸光度(Aj),以蒸馏水代替样品溶液作为空白测的吸光度(A0),重复三次。清除率按下式计算:
清除率(%)=[1-(Ai-Aj)/A0]×100
2.2黑木耳多糖清除DPPH·自由基作用
分别取2mL不同浓度的样品液于试管中,加入2mL 2×10-4mol/L的DPPH·溶液(以无水乙醇配制),混合均匀,暗处反应30分钟后于517nm处测定其吸光度(Ai),以蒸馏水代替样品液测得空白吸光度(A0),重复三次。清除率按下式计算:
清除率(%)=(A0-Ai)/A0×100
2.3黑木耳多糖清除ABTS+自由基作用
分别取0.2mL的样品溶液与3.8mL上述ABTS分析溶液混合,6min后在734nm处测定吸光度Ai。以蒸馏水代替ABTS分析溶液,测得吸光度Aj,以蒸馏水代替样品溶液测得吸光度A0。
清除率(%)=[1-(Ai-Aj)/A0]×100
3、实验结果
图2为黑木耳多糖对·OH的清除作用,可以看到黑木耳多糖羧甲基化前后各组分对·OH自由基有一定的清除作用,且羧甲基化修饰后多糖的抗氧化活性皆优于修饰前多糖。在浓度为2mg/mL时,经修饰的CMAAP22和CMAAP的清除率分别为52.13%和38.42%(修饰前AAP为27.75%)。图3为黑木耳多糖对DPPH·的清除作用,黑木耳多糖羧甲基化前后各组分对DPPH·均有一定的清除作用,且羧甲基化修饰后多糖的抗氧化活性皆优于修饰前多糖。在浓度为1.5mg/mL时,经修饰的CMAAP22和CMAAP的清除率分别为78.95%和63.03%(修饰前AAP为46.38%)。图4为黑木耳多糖对ABTS+ 的清除作用,黑木耳多糖羧甲基化前后各组分对ABTS+均有一定的清除作用,且羧甲基化修饰后多糖的抗氧化活性皆优于修饰前多糖,弱于Vc。在浓度为2mg/mL时, CMAAP22和CMAAP的清除率分别为65.53%和55.88%(修饰前AAP为38.30%)。
4、结论
与未羧甲基化黑木耳多糖相比,羧甲基化黑木而多糖对DPPH自由基、羟自由基和ABTS+自由基的清除都有很大的提高。
Claims (6)
1.一种羧甲基化黑木耳多糖,其特征在于该多糖分子量为3.4×106 Da;单糖组成为:甘露糖(man) : 葡萄糖(glu) = 1.06 : 1;该多糖以β-(1→3)-D- man为主链,glu以取代基的形式键和于甘露糖的O-2和O-6位,糖残基的C-2, C-4 和C-6位由–CH2COOH部分取代;该多糖溶解度为26 mg/mL。
2.一种羧甲基化黑木耳粗多糖,其特征在于其多糖得率为61.36%;羧甲基化取代度为0.857;溶解度为0.6 mg/mL。
3.权利要求1所述的一种羧甲基化黑木耳多糖的制备方法,其特征在于按照下述步骤进行:
⑴ 黑木耳多糖的提取方法:
以料液比1:50-1:70,在温度80-100℃水中提取2-4h,提取2次,合并上清液,上清液经浓缩后,加入乙醇醇沉,使得多糖的浓缩液中乙醇浓度为60-85%,所得沉淀离心、经冷冻干燥24-48h后得黑木耳粗多糖;
⑵ 羧甲基化黑木耳多糖的制备:
取上述传统水提醇沉所得黑木耳粗多糖,以料液比1:40加入异丙醇,室温剧烈搅拌15min;在上述溶液中按照体积比40:7的比例逐滴加入质量浓度为20% 氢氧化钠溶液,室温下搅拌反应一定时间;再按照黑木耳粗多糖与氯乙酸质量比1:0.5-1.5的比例加入氯乙酸,于20-60℃恒温水浴锅中反应2-4 h;反应液用稀盐酸中和至中性,经透析、浓缩和醇沉后即得羧甲基化黑木耳粗多糖;
⑶ 取羧甲基化黑木耳粗多糖,用适量水溶解,离心除去不溶物,上清液通过DEAE-52离子交换柱进行分离;逐步以0-1 mol/L的NaCl溶液洗脱,用硫酸-苯酚法绘制洗脱曲线,根据洗脱曲线分别收取合并洗脱液,其中0.1mol/L NaCl的洗脱液经浓缩、透析后,上葡聚糖凝胶柱,以0.1 mol/L NaCl洗脱,根据洗脱曲线收取合并洗脱液,经浓缩、透析、冻干得羧甲基化黑木耳多糖。
4.权利要求2所述的一种羧甲基化黑木耳粗多糖的制备方法,其特征在于按照下述步骤进行:
⑴ 黑木耳多糖的提取方法:
以料液比1:50-1:70,在温度80-100℃水中提取2-4h,提取2次,合并上清液,上清液经浓缩后,加入乙醇醇沉,使得多糖的浓缩液中乙醇浓度为60-85%,所得沉淀离心、经冷冻干燥24-48h后得黑木耳粗多糖;
⑵ 羧甲基化黑木耳多糖的制备:
取上述传统水提醇沉所得黑木耳粗多糖,以料液比1:40加入异丙醇,室温剧烈搅拌15min;在上述溶液中按照体积比40:7的比例逐滴加入质量浓度为20% 氢氧化钠溶液,室温下搅拌反应一定时间;再按照黑木耳粗多糖与氯乙酸质量比1:0.5-1.5的比例加入氯乙酸,于20-60℃恒温水浴锅中反应2-4 h;反应液用稀盐酸中和至中性,经透析、浓缩和醇沉后即得羧甲基化黑木耳粗多糖。
5.权利要求1所述的一种羧甲基化黑木耳多糖作为抗氧化剂在功能食品和食品添加剂中的应用。
6.权利要求2所述的一种羧甲基化黑木耳粗多糖作为抗氧化剂在功能食品和食品添加剂中的应用。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 201110219047 CN102321186B (zh) | 2011-08-02 | 2011-08-02 | 一种羧甲基化黑木耳多糖、粗多糖及其制备方法和应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 201110219047 CN102321186B (zh) | 2011-08-02 | 2011-08-02 | 一种羧甲基化黑木耳多糖、粗多糖及其制备方法和应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102321186A true CN102321186A (zh) | 2012-01-18 |
CN102321186B CN102321186B (zh) | 2013-07-17 |
Family
ID=45449041
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 201110219047 Expired - Fee Related CN102321186B (zh) | 2011-08-02 | 2011-08-02 | 一种羧甲基化黑木耳多糖、粗多糖及其制备方法和应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN102321186B (zh) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106188328A (zh) * | 2016-07-15 | 2016-12-07 | 浙江省海洋开发研究院 | 一种羧甲基化多糖的制备方法 |
CN106632709A (zh) * | 2016-05-12 | 2017-05-10 | 江苏大学 | 一种羧甲基化五味子多糖及其制备方法和应用 |
CN108727511A (zh) * | 2018-06-26 | 2018-11-02 | 贵州师范大学 | 一种羧甲基化桑葚多糖及其制备方法和应用 |
CN109232754A (zh) * | 2018-06-29 | 2019-01-18 | 桂林理工大学 | 一种具有提高抗氧化活性的西番莲果皮多糖羧甲基化修饰产物及其制备方法 |
WO2024045207A1 (zh) * | 2022-08-31 | 2024-03-07 | 北京北清博育信息技术研究有限公司 | 黑木耳多糖及其应用和制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2078755A1 (en) * | 2007-12-18 | 2009-07-15 | Amin Karmali | Process for simultaneous extraction and purification of fine chemicals from spent mushroom compost, mushroom stems and partially degraded mushroom fruiting bodies |
CN101712727A (zh) * | 2009-11-24 | 2010-05-26 | 中国计量学院 | 一种黑木耳多糖的提取方法 |
-
2011
- 2011-08-02 CN CN 201110219047 patent/CN102321186B/zh not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2078755A1 (en) * | 2007-12-18 | 2009-07-15 | Amin Karmali | Process for simultaneous extraction and purification of fine chemicals from spent mushroom compost, mushroom stems and partially degraded mushroom fruiting bodies |
CN101712727A (zh) * | 2009-11-24 | 2010-05-26 | 中国计量学院 | 一种黑木耳多糖的提取方法 |
Non-Patent Citations (1)
Title |
---|
张华等: "黑木耳多糖的羧甲基化及其对肝癌细胞HepG2的抑制作用", 《食品与机械》, vol. 27, no. 3, 18 May 2011 (2011-05-18) * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106632709A (zh) * | 2016-05-12 | 2017-05-10 | 江苏大学 | 一种羧甲基化五味子多糖及其制备方法和应用 |
CN106632709B (zh) * | 2016-05-12 | 2019-05-31 | 江苏大学 | 一种羧甲基化五味子多糖及其制备方法和应用 |
CN106188328A (zh) * | 2016-07-15 | 2016-12-07 | 浙江省海洋开发研究院 | 一种羧甲基化多糖的制备方法 |
CN108727511A (zh) * | 2018-06-26 | 2018-11-02 | 贵州师范大学 | 一种羧甲基化桑葚多糖及其制备方法和应用 |
CN108727511B (zh) * | 2018-06-26 | 2021-04-02 | 贵州师范大学 | 一种羧甲基化桑葚多糖及其制备方法和应用 |
CN109232754A (zh) * | 2018-06-29 | 2019-01-18 | 桂林理工大学 | 一种具有提高抗氧化活性的西番莲果皮多糖羧甲基化修饰产物及其制备方法 |
CN109232754B (zh) * | 2018-06-29 | 2021-07-13 | 桂林理工大学 | 一种具有提高抗氧化活性的西番莲果皮多糖羧甲基化修饰产物及其制备方法 |
WO2024045207A1 (zh) * | 2022-08-31 | 2024-03-07 | 北京北清博育信息技术研究有限公司 | 黑木耳多糖及其应用和制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN102321186B (zh) | 2013-07-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Gong et al. | Physicochemical properties and biological activities of polysaccharides from Lycium barbarum prepared by fractional precipitation | |
Rozi et al. | Sequential extraction, characterization and antioxidant activity of polysaccharides from Fritillaria pallidiflora Schrenk | |
Wang et al. | Structural characterization of a novel acidic polysaccharide from Rosa roxburghii Tratt fruit and its α-glucosidase inhibitory activity | |
Chen et al. | Ultrasonic extraction, structural characterization, physicochemical properties and antioxidant activities of polysaccharides from bamboo shoots (Chimonobambusa quadrangularis) processing by-products | |
Zhang et al. | Structural characterization and in vitro antitumor activity of an acidic polysaccharide from Angelica sinensis (Oliv.) Diels | |
Han et al. | Structural characterization and anti-A549 lung cancer cells bioactivity of a polysaccharide from Houttuynia cordata | |
Cai et al. | Purification, characterization and anticoagulant activity of the polysaccharides from green tea | |
Xu et al. | Seperation, characterization and inhibition on α-glucosidase, α-amylase and glycation of a polysaccharide from blackcurrant fruits | |
Hu et al. | Chemical modification and antioxidant activity of the polysaccharide from Acanthopanax leucorrhizus | |
Wang et al. | Structural elucidation and immune-enhancing activity of peculiar polysaccharides fractioned from marine clam Meretrix meretrix (Linnaeus) | |
Pawlaczyk et al. | Anticoagulant and anti-platelet activity of polyphenolic-polysaccharide preparation isolated from the medicinal plant Erigeron canadensis L. | |
Wang et al. | Isolation and purification of brown algae fucoidan from Sargassum siliquosum and the analysis of anti-lipogenesis activity | |
CN102321186B (zh) | 一种羧甲基化黑木耳多糖、粗多糖及其制备方法和应用 | |
Yuan et al. | Immunoenhancing glucuronoxylomannan from Tremella aurantialba Bandoni et Zang and its low-molecular-weight fractions by radical depolymerization: Properties, structures and effects on macrophages | |
CN110437288B (zh) | 一种海参岩藻多糖及其制备方法和应用 | |
Yi et al. | Effects of alkali dissociation on the molecular conformation and immunomodulatory activity of longan pulp polysaccharide (LPI) | |
Li et al. | Non-starch polysaccharide from Chinese yam activated RAW 264.7 macrophages through the Toll-like receptor 4 (TLR4)-NF-κB signaling pathway | |
Chen et al. | Preliminary characterization and antioxidant and hypoglycemic activities in vivo of polysaccharides from Huidouba | |
Li et al. | Structural characterization and immunomodulatory activity of a new heteropolysaccharide from Prunella vulgaris | |
Zhang et al. | Characterization and immunomodulatory effect of an alkali-extracted galactomannan from Morchella esculenta | |
CN104725520B (zh) | 一种分心木酸性多糖及其制备和应用 | |
Kasimu et al. | Water-soluble polysaccharide from Erythronium sibiricum bulb: Structural characterisation and immunomodulating activity | |
Song et al. | Structural characterization and anticoagulant activity of two polysaccharides from Patinopecten yessoensis viscera | |
CN105037577B (zh) | 一种促凝血黑莓籽多糖及其提取分离方法、应用 | |
Yan et al. | Purification, structural characterization and bioactivity evaluation of a novel proteoglycan produced by Corbicula fluminea |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20130717 |