CN113024681A - Polygonatum galagan galactan and its preparation method and application - Google Patents
Polygonatum galagan galactan and its preparation method and application Download PDFInfo
- Publication number
- CN113024681A CN113024681A CN202110256434.8A CN202110256434A CN113024681A CN 113024681 A CN113024681 A CN 113024681A CN 202110256434 A CN202110256434 A CN 202110256434A CN 113024681 A CN113024681 A CN 113024681A
- Authority
- CN
- China
- Prior art keywords
- polygonatum
- galactan
- rhizoma polygonati
- sibiricum
- preparation
- 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
- 241000756042 Polygonatum Species 0.000 title claims abstract description 214
- 238000002360 preparation method Methods 0.000 title claims abstract description 34
- 239000003814 drug Substances 0.000 claims abstract description 19
- 230000001737 promoting effect Effects 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 115
- 241000037831 Polygonatum sibiricum Species 0.000 claims description 69
- 150000004676 glycans Chemical class 0.000 claims description 40
- 229920001282 polysaccharide Polymers 0.000 claims description 40
- 239000005017 polysaccharide Substances 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 32
- 239000000126 substance Substances 0.000 claims description 19
- 238000001035 drying Methods 0.000 claims description 18
- 238000010025 steaming Methods 0.000 claims description 17
- 241001468611 Polygonatum cyrtonema Species 0.000 claims description 15
- 239000002244 precipitate Substances 0.000 claims description 14
- 235000013305 food Nutrition 0.000 claims description 11
- 238000000108 ultra-filtration Methods 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 10
- 238000001556 precipitation Methods 0.000 claims description 10
- 238000000502 dialysis Methods 0.000 claims description 9
- 239000002775 capsule Substances 0.000 claims description 8
- 230000029087 digestion Effects 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 7
- 241001633680 Polygonatum odoratum Species 0.000 claims description 6
- 238000000746 purification Methods 0.000 claims description 6
- 230000001105 regulatory effect Effects 0.000 claims description 6
- 238000002270 exclusion chromatography Methods 0.000 claims description 5
- 230000001815 facial effect Effects 0.000 claims description 3
- 239000008176 lyophilized powder Substances 0.000 claims description 3
- 230000002496 gastric effect Effects 0.000 claims description 2
- 229920002670 Fructan Polymers 0.000 claims 1
- 239000002537 cosmetic Substances 0.000 claims 1
- 230000008991 intestinal motility Effects 0.000 claims 1
- 238000003809 water extraction Methods 0.000 claims 1
- OMDQUFIYNPYJFM-XKDAHURESA-N (2r,3r,4s,5r,6s)-2-(hydroxymethyl)-6-[[(2r,3s,4r,5s,6r)-4,5,6-trihydroxy-3-[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@H](O)[C@H](O)O1 OMDQUFIYNPYJFM-XKDAHURESA-N 0.000 abstract description 19
- 229920000926 Galactomannan Polymers 0.000 abstract description 19
- 239000006041 probiotic Substances 0.000 abstract description 18
- 235000018291 probiotics Nutrition 0.000 abstract description 18
- 230000000694 effects Effects 0.000 abstract description 16
- 229930182830 galactose Natural products 0.000 abstract description 12
- 241000894006 Bacteria Species 0.000 abstract description 11
- 230000035755 proliferation Effects 0.000 abstract description 11
- 229940079593 drug Drugs 0.000 abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 28
- 239000000203 mixture Substances 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 17
- 239000000463 material Substances 0.000 description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 13
- 125000002519 galactosyl group Chemical group C1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 description 13
- 239000001963 growth medium Substances 0.000 description 13
- 239000006228 supernatant Substances 0.000 description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 150000002772 monosaccharides Chemical class 0.000 description 12
- 230000001580 bacterial effect Effects 0.000 description 11
- 230000000968 intestinal effect Effects 0.000 description 11
- -1 mucus Polymers 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 241000037826 Polygonatum kingianum Species 0.000 description 8
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical class [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000004108 freeze drying Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- 238000011160 research Methods 0.000 description 7
- 238000005303 weighing Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000007069 methylation reaction Methods 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
- 238000001514 detection method Methods 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- 230000011987 methylation Effects 0.000 description 5
- 239000012982 microporous membrane Substances 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 230000008855 peristalsis Effects 0.000 description 5
- 239000008213 purified water Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 241000186000 Bifidobacterium Species 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 4
- 241000186660 Lactobacillus Species 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 238000012869 ethanol precipitation Methods 0.000 description 4
- 230000007717 exclusion Effects 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 235000013355 food flavoring agent Nutrition 0.000 description 4
- 229930182478 glucoside Natural products 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 229920000499 poly(galactose) polymer Polymers 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 235000013736 caramel Nutrition 0.000 description 3
- 230000007812 deficiency Effects 0.000 description 3
- 238000001212 derivatisation Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- 230000008014 freezing Effects 0.000 description 3
- FTSSQIKWUOOEGC-RULYVFMPSA-N fructooligosaccharide Chemical compound OC[C@H]1O[C@@](CO)(OC[C@@]2(OC[C@@]3(OC[C@@]4(OC[C@@]5(OC[C@@]6(OC[C@@]7(OC[C@@]8(OC[C@@]9(OC[C@@]%10(OC[C@@]%11(O[C@H]%12O[C@H](CO)[C@@H](O)[C@H](O)[C@H]%12O)O[C@H](CO)[C@@H](O)[C@@H]%11O)O[C@H](CO)[C@@H](O)[C@@H]%10O)O[C@H](CO)[C@@H](O)[C@@H]9O)O[C@H](CO)[C@@H](O)[C@@H]8O)O[C@H](CO)[C@@H](O)[C@@H]7O)O[C@H](CO)[C@@H](O)[C@@H]6O)O[C@H](CO)[C@@H](O)[C@@H]5O)O[C@H](CO)[C@@H](O)[C@@H]4O)O[C@H](CO)[C@@H](O)[C@@H]3O)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@@H](O)[C@@H]1O FTSSQIKWUOOEGC-RULYVFMPSA-N 0.000 description 3
- 229940107187 fructooligosaccharide Drugs 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229940039696 lactobacillus Drugs 0.000 description 3
- 238000009630 liquid culture Methods 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 230000000529 probiotic effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- 238000003696 structure analysis method Methods 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- 238000009777 vacuum freeze-drying Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 2
- 238000001026 1H--1H correlation spectroscopy Methods 0.000 description 2
- 238000012593 1H–1H TOCSY Methods 0.000 description 2
- RMTFNDVZYPHUEF-XZBKPIIZSA-N 3-O-methyl-D-glucose Chemical compound O=C[C@H](O)[C@@H](OC)[C@H](O)[C@H](O)CO RMTFNDVZYPHUEF-XZBKPIIZSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241001134770 Bifidobacterium animalis Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 229920002907 Guar gum Polymers 0.000 description 2
- 239000004201 L-cysteine Substances 0.000 description 2
- 235000013878 L-cysteine Nutrition 0.000 description 2
- 241000037813 Polygonatum falcatum Species 0.000 description 2
- 241001465611 Polygonatum nodosum Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229920002385 Sodium hyaluronate Polymers 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000005349 anion exchange Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N benzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 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
- 229940118852 bifidobacterium animalis Drugs 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- 229960001631 carbomer Drugs 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 229940081733 cetearyl alcohol Drugs 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229960001701 chloroform Drugs 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000000665 guar gum Substances 0.000 description 2
- 235000010417 guar gum Nutrition 0.000 description 2
- 229960002154 guar gum Drugs 0.000 description 2
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 2
- 229920002674 hyaluronan Polymers 0.000 description 2
- 229960003160 hyaluronic acid Drugs 0.000 description 2
- DLINORNFHVEIFE-UHFFFAOYSA-N hydrogen peroxide;zinc Chemical compound [Zn].OO DLINORNFHVEIFE-UHFFFAOYSA-N 0.000 description 2
- 239000000413 hydrolysate Substances 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 239000006872 mrs medium Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 239000012466 permeate Substances 0.000 description 2
- 229950008882 polysorbate Drugs 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000001896 rotating frame Overhauser effect spectroscopy Methods 0.000 description 2
- 150000004666 short chain fatty acids Chemical class 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229940010747 sodium hyaluronate Drugs 0.000 description 2
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 2
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 2
- 210000000952 spleen Anatomy 0.000 description 2
- 239000008223 sterile water Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- 229920001285 xanthan gum Polymers 0.000 description 2
- 239000000230 xanthan gum Substances 0.000 description 2
- 235000010493 xanthan gum Nutrition 0.000 description 2
- 229940082509 xanthan gum Drugs 0.000 description 2
- XDIYNQZUNSSENW-UUBOPVPUSA-N (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O XDIYNQZUNSSENW-UUBOPVPUSA-N 0.000 description 1
- 238000002223 1H--13C heteronuclear multiple bond coherence Methods 0.000 description 1
- 238000004701 1H-13C HSQC Methods 0.000 description 1
- 238000003979 3D HSQC-TOCSY Methods 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 241000901050 Bifidobacterium animalis subsp. lactis Species 0.000 description 1
- 241000207892 Convolvulus Species 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 240000001046 Lactobacillus acidophilus Species 0.000 description 1
- 240000006024 Lactobacillus plantarum Species 0.000 description 1
- 241000234280 Liliaceae Species 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 235000008737 Polygonatum biflorum Nutrition 0.000 description 1
- 241001340941 Polygonatum griffithii Species 0.000 description 1
- 241001478683 Polygonatum humile Species 0.000 description 1
- 241000037816 Polygonatum inflatum Species 0.000 description 1
- 241000243490 Polygonatum pubescens Species 0.000 description 1
- 241000037833 Polygonatum stenophyllum Species 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 229920002684 Sepharose Polymers 0.000 description 1
- 241000220261 Sinapis Species 0.000 description 1
- 241000082085 Verticillium <Phyllachorales> Species 0.000 description 1
- 208000005946 Xerostomia Diseases 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 206010003549 asthenia Diseases 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 229940097217 cardiac glycoside Drugs 0.000 description 1
- 239000002368 cardiac glycoside Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003795 chemical substances by application 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
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 208000017574 dry cough Diseases 0.000 description 1
- 206010013781 dry mouth Diseases 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 229910001651 emery Inorganic materials 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- 150000002256 galaktoses Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 125000003147 glycosyl group Chemical group 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 238000001052 heteronuclear multiple bond coherence spectrum Methods 0.000 description 1
- 238000005570 heteronuclear single quantum coherence Methods 0.000 description 1
- 238000004192 high performance gel permeation chromatography Methods 0.000 description 1
- 238000007731 hot pressing Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 229930013686 lignan Natural products 0.000 description 1
- 235000009408 lignans Nutrition 0.000 description 1
- 150000005692 lignans Chemical class 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- OQUKIQWCVTZJAF-UHFFFAOYSA-N phenol;sulfuric acid Chemical compound OS(O)(=O)=O.OC1=CC=CC=C1 OQUKIQWCVTZJAF-UHFFFAOYSA-N 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 150000003214 pyranose derivatives Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000012465 retentate Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 235000021391 short chain fatty acids Nutrition 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 229930002534 steroid glycoside Natural products 0.000 description 1
- 150000005856 steroid saponins Chemical class 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0003—General processes for their isolation or fractionation, e.g. purification or extraction from biomass
-
- 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
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/88—Liliopsida (monocotyledons)
- A61K36/896—Liliaceae (Lily family), e.g. daylily, plantain lily, Hyacinth or narcissus
- A61K36/8969—Polygonatum (Solomon's seal)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/02—Suppositories; Bougies; Bases therefor; Ovules
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0036—Galactans; Derivatives thereof
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Polymers & Plastics (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Nutrition Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Mycology (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Microbiology (AREA)
- Sustainable Development (AREA)
- Food Science & Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to a polygonatum galactan and a preparation method and application thereof, wherein the polygonatum galactan has a structure shown as a general formula I, in the formula (I), n represents the number of sugar repeating units, and is a natural number. In the general structure of the polygonatum galactan, the polygonatum galactan is represented by beta (1 → 4)) Glycosidic linkages are the main chain to which the side chain galactose is linked by beta (1 → 6) glycosidic linkages. The polygonatum galactomannan and the pharmaceutical composition containing the polygonatum galactomannan have certain activity of promoting the proliferation of probiotics, so that the polygonatum galactomannan and the pharmaceutical composition containing the polygonatum galactomannan have medical value in the preparation of medicines for benefiting bacteria.
Description
Technical Field
The invention relates to the technical field of food and medicine, in particular to polygonatum galactan and a preparation method and application thereof.
Background
Rhizoma Polygonati is a plant of genus rhizoma Polygonati of family Liliaceae, and is named because of its tonic effect. The genus plant mainly includes Polygonatum sibiricum (Polygonatum sibiricum), Polygonatum kingianum (Polygonatum kingianum), Polygonatum cyrtonema (Polygonatum cyrtonema), Polygonatum conatum (Polygonatum cathayensis), Polygonatum sibiricum (Polygonatum cathayensis), Polygonatum odoratum (Polygonatum odoratum), Polygonatum minor (Polygonatum humile), Polygonatum odoratum (Polygonatum inflatum), Polygonatum falcatum (Polygonatum flagatum), Polygonatum sibiricum curvatum (Polygonatum curvatum), Polygonatum cyrtonema (Polygonatum desoxyphyllum), Polygonatum longum (Polygonatum sibiricum), Polygonatum crudella (Polygonatum hirtum), Polygonatum giganteum (Polygonatum sibiricum), Polygonatum giganteum (Polygonatum giganteum), Polygonatum sibiricum (Polygonatum sibiricum), Polygonatum sibiricum minor rhizome (Polygonatum), Polygonatum sibiricum uncitum rhizome minor rhizome (Polygonatum sibiricum grandiflorum), Polygonatum sibiricum (Polygonatum sibiricum grandiflorum medicine (Polygonatum), Polygonatum sibiricum grandiflorum crispum), Polygonatum (Polygonatum rhizome), Polygonatum sibiricum grandiflorum), Polygonatum sibiricum (Polygonatum sibiricum), Polygonatum sibiricum) blend root of Polygonatum sibiricum, Polygonatum sibiricum (Polygonatum sibiricum), Polygonatum sibiricum grandiflorum paniculatum medicine (Polygonatum), Polygonatum sibiricum grandiflorum paniculatum), Polygonatum sibiricum (Polygonatum sibiricum), Polygonatum sibiricum grandiflorum paniculatum rhizome (Polygonatum sibiricum), Polygonatum sibiricum grandiflorum paniculatum), Polygonatum (Polygonatum sibiricum) blend root of, Rhizoma Polygonati (Polygonatum macrocarpium), rhizoma Polygonati Sinapis (Polygonatum sibiricum), rhizoma Polygonati officinalis (Polygonatum verticillium), and rhizoma Polygonati stenophyllum (Polygonatum stenophyllum). The medicinal part of the sealwort is rhizome, sweet and mild in taste. Has effects in invigorating qi, nourishing yin, invigorating spleen, moistening lung, and invigorating kidney. Can be used for treating spleen deficiency, stomach weakness, asthenia, xerostomia, dry cough due to lung deficiency, essence and blood deficiency, internal heat, and diabetes. Rhizome of Polygonatum plant can be used as medicine, and the rhizome mainly comprises the following chemical components: rhizoma Polygonati polysaccharide, mucus, starch, steroid saponin, anthraquinone compounds, alkaloid, cardiac glycoside, lignan, vitamins, fat, protein and various amino acids useful for human body, wherein rhizoma Polygonati polysaccharide is the most effective component in rhizoma Polygonati.
However, the chemical structure of plant polysaccharide is very complex, the same plant often contains a plurality of different types of polysaccharide, and the research on the biological efficacy of polysaccharide is less developed, so the research and development of the application of plant polysaccharide in the fields of biological medicine and food are slow.
Disclosure of Invention
The invention aims to: aiming at the problems of insufficient research depth of rhizoma polygonati, complex components of plant polysaccharide in rhizoma polygonati and slow development of research on plant polysaccharide in rhizoma polygonati in the prior art, the invention provides the rhizoma polygonati galactan and the preparation method and application thereof.
In order to achieve the purpose, the invention adopts the technical scheme that:
a polygonatum galactan having a chemical structure represented by the following general formula I:
in the formula (I), n represents the number of sugar repeating units, and n is a natural number.
Pharmacological research shows that the polygonatum galactan component with a novel structure can promote the proliferation of probiotics including lactobacillus and bifidobacterium, and has an obvious effect within 2 to 12 hours; with the increase of the drug concentration, the capability of the polygonatum galactomannan in promoting the proliferation of probiotics is obviously enhanced, which shows that the polygonatum galactomannan can promote the growth of the probiotics.
In one embodiment of the invention, the weight average molecular weight of the polygonatum galactan is 4000 Da-15000 Da, and the polydispersity coefficient is 1-3.
Further, the polydispersity of the polygonatum galactan may be 1.5, 2, 2.5, etc., or the dispersion coefficient values may be within a range of up to and down to 20%.
In order to obtain the polygonatum galactomannan component, the invention also provides the following preparation process method, so that polygonatum galactomannan can be conveniently separated and extracted from natural polygonatum medicinal materials.
A preparation method of the polygonatum sibiricum galactan comprises the following steps:
extracting crude polysaccharide of rhizoma Polygonati from rhizoma Polygonati;
purifying the components with the weight average molecular weight of 4000 Da-15000 Da in the crude polygonatum sibiricum polysaccharide to obtain the polygonatum sibiricum galactan.
Further, the preparation method of the polygonatum galactan specifically comprises the following steps:
and 2, purifying and separating components with the weight-average molecular weight of 4000 Da-15000 Da in the crude polygonatum sibiricum polysaccharide to obtain the polygonatum sibiricum galactan.
The invention provides a process method which adopts a processed product rhizoma polygonati to extract crude polysaccharide with alcohol concentration of about 60 v%, and the rhizoma polygonati galactan is obtained through purification and separation. The processed rhizoma polygonati is selected to separate and purify the rhizoma polygonati processed by the traditional processing technology to obtain natural medicinal chemical components with specific activity, and the method has great biological medicine application value.
Further, the processed rhizoma polygonati is a processed rhizoma polygonati rhizome product, and crude rhizoma polygonati polysaccharide is obtained by extracting and separating the processed rhizoma polygonati.
Further, the processed rhizoma Polygonati is prepared by steaming and sun-drying rhizoma Polygonati for 6-9 times.
Further, crude polysaccharide of the processed rhizoma polygonati under the concentration of 60% alcohol is extracted.
In one embodiment, the step 1 of extracting the crude polysaccharide specifically comprises the following steps: extracting rhizoma Polygonati with water under reflux, precipitating the extractive solution with ethanol, screening ethanol precipitate with alcohol concentration of 50-65 v%, centrifuging, and collecting the ethanol precipitate. Preferably, 60 v% ethanol precipitate is used.
Further, after the processed rhizoma polygonati is extracted by hot water, ethanol is respectively used for fractional precipitation of rhizoma polygonati polysaccharide to ensure that the alcohol concentration reaches 36-45 v% and 55-65 v%, and then the precipitate with the ethanol concentration of 55-65 v% is centrifugally collected. Preferably, the ethanol concentration in the two times is 40% and 60%, respectively.
Further, the polygonatum galactan is extracted from rhizomes of sealwort of polygonatum, and the steps comprise the following steps: extracting rhizome of Polygonatum sibiricum plant with hot water, precipitating Polygonatum sibiricum polysaccharide with ethanol to alcohol concentrations of 40% and 60%, and centrifuging to collect precipitate with 60% ethanol concentration.
In one embodiment, step 2, the purification and separation process, is selected from one or more of gel exclusion chromatography column, dialysis, and ultrafiltration. The components with the weight average molecular weight of 4000 Da-15000 Da in the polygonatum polysaccharide are obtained by separation, and the polygonatum polysaccharide has unique activity characteristics.
Namely, the method for purifying the components with the weight-average molecular weight of 4000 Da-15000 Da of the crude polygonatum rhizome stem polysaccharide is selected from one or more of alcohol precipitation reclassification, gel exclusion chromatographic column method, dialysis method and ultrafiltration method.
In one embodiment, the polygonatum plant comprises one or more of polygonatum, polygonatum kingianum, polygonatum cyrtonema, polygonatum clavatum, polygonatum odoratum, kadin polygonatum, polygonatum minor, polygonatum pubescens, polygonatum pendula, polygonatum longum, polygonatum hirsutum, polygonatum macrospermanum, polygonatum stipulatum, polygonatum brevifolium, polygonatum muticum, polygonatum stigmata, polygonatum solomorpha, polygonatum bicolor, polygonatum nodosum, polygonatum paratyphyllae, polygonatum laevigatum, polygonatum griffithii, polygonatum falcatum, polygonatum tenuifolium polygonati, polygonatum hotriver polygonatum, polygonatum Xinjiang, polygonatum. One or more of the above-mentioned Polygonatum plants may be selected during the preparation process, and the rhizomes of the above-mentioned Polygonatum plants may be mainly used.
A pharmaceutical composition comprises an effective amount of a polygonatum galactan.
Further, the medicine composition also comprises effective dose of polygonatum galactan and/or medicinal and/or food auxiliary materials or excipients or flavoring agents.
Further, the polygonatum galactan is combined with a pharmaceutical carrier to be used as an active ingredient in an intimate admixture.
Further, the polygonatum galactan is in a dosage form of oral administration or parenteral administration. Specifically, a dosage form thereof may be, for example, a capsule, a cachet or a tablet containing polygonatum galactan as an active ingredient.
Further, the polygonatum galactan can be used locally, for example, can be prepared into one of the following dosage forms: aerosols, creams, ointments, lotions, dusting powders, mouthwashes, gargles, and the like.
Further, the polygonatum galactan can also be applied in a rectal or vaginal mode. For example, suppositories can be formed by mixing with the necessary carrier materials. Suitable carriers include cocoa butter and other materials commonly used in the art, and suppositories are conveniently formed by first mixing the polygonatum galactan with the softened or melted carrier, then cooling and shaping in a mold.
Application of the above rhizoma Polygonati galactan or pharmaceutical composition in product for promoting growth of probiotic bacteria is provided.
In one embodiment, the dosage form of the pharmaceutical composition is lyophilized powder, oral liquid, capsule, tablet, paste, suppository, and the like.
Application of the above medicinal composition in preparing food and medicine for promoting digestion and intestinal peristalsis is provided. Specifically, the application of the polygonatum galactan comprises at least one of the following applications in the preparation of food and/or medicines for regulating gastrointestinal flora, promoting intestinal peristalsis and/or promoting digestion.
In summary, due to the adoption of the technical scheme, the invention has the beneficial effects that:
1. the sealwort galactan obtained by separation is reported for the first time, and is determined to have the effect of promoting the activity of intestinal probiotic groups through animal experiment research of the inventor, so that the sealwort galactan has important application potential of health care products.
2. After being decomposed by probiotics, the polygalactose of the invention can increase metabolites of short-chain fatty acids such as lactic acid, acetic acid and the like, thereby obviously reducing the pH value of the culture medium, being more beneficial to the survival of the probiotics and achieving the effect of inhibiting the propagation of harmful flora.
Description of the drawings:
FIG. 1 is an HPLC chart of a polygonatum galactan;
FIG. 2 is a HPLC chart of monosaccharide composition analysis of a polygonatum galactan, wherein a is a HPLC chart of a monosaccharide standard, b is a HPLC chart of monosaccharide composition analysis of a polygonatum galactan, and Gal represents galactose;
FIG. 3 is an infrared spectrum of a polygonatum sibiricum galactan;
FIG. 4 is the nuclear magnetic resonance spectrum of the galactomannan of Polygonatum sibiricum, wherein the graph a is1H NMR spectrum, FIG. b is13C NMR spectrum;
FIG. 5 is a nuclear magnetic resonance spectrum of galactomannan from rhizoma Polygonati, wherein, a is HSQC-TOCSY NMR chart, b is HMBC NMR chart;
figure 6 is a graph of the effect of polygonatum galactan on the pH of the medium inoculated with probiotics including lactobacillus and bifidobacterium at different times (n-3);
figure 7 is a graph of the effect of polygonatum galactan on the OD values of media inoculated with probiotics including lactobacillus and bifidobacterium at different times (n-3);
FIG. 8 is a graph of the effect of polygonatum galactan on the number of bacteria in a medium inoculated with probiotics including lactobacilli and bifidobacteria at different times (n-3).
Detailed Description
In order that the invention may be more fully understood, a more particular description of the invention will now be rendered by reference to specific embodiments thereof that are illustrated in the appended drawings. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.
The polygonatum galactan provided by the embodiment of the invention has a structure represented by the following general formula I:
in the formula (I), n represents the number of sugar repeating units, and n is a natural number.
The polygonatum galactomannan takes a beta (1 → 4) glycosidic bond as a main chain, and galactose as a side chain is connected to the main chain by the beta (1 → 6) glycosidic bond.
The inventor of the invention has intensively studied the polygonatum polysaccharide and surprisingly found that the polygonatum galactan with a novel structure can be obtained by extracting and purifying polygonatum plants such as polygonatum cyrtonema and the like by an innovative method. Through further pharmacological activity research, the newly discovered polygonatum galactan can remarkably promote the proliferation of probiotics, so that the polygonatum galactan has the application of preparing medicines and/or foods for intestinal regulation and digestion assistance. Therefore, the polygonatum galactan with a novel structure, the preparation method and the medicinal composition thereof and the application of the polygonatum galactan in preparation of intestinal tract regulating and digestion aiding medicines are disclosed and reported for the first time.
Further, n may range from 1 to 40, for example, 1 to 30, 1 to 20, 1 to 15, 1 to 10, 2 to 5, and more specifically, the distance may be 1, 2, 4,6, 8, 10, 14, 18, 22, or the like. The separation conditions may be slightly different according to different natural rhizoma Polygonati raw materials, processing methods and separation conditions.
In a specific example, the weight average molecular weight of the polygonatum galactan is 4000 Da-15000 Da, and the polydispersity coefficient is 1-3. Preferably, the weight average molecular weight of the polygonatum galactan is 6000 Da-10000 Da.
In a specific example, when n ═ 1 in formula I, the polygonatum galactan has a structure represented by the following formula II:
the preparation method of the polygonatum galactan provided by the embodiment of the invention comprises the following steps of S1-S2:
s1: extracting polysaccharide from rhizoma Polygonati.
S2: purifying the components with the weight average molecular weight of 4000 Da-15000 Da in the polygonatum polysaccharide to obtain the polygonatum galactan.
Further, the processed raw material of the polygonatum plant is a processed product of polygonatum (or called a polygonatum processed product).
In one specific example, the polygonatum genus plant includes, but is not limited to, polygonatum kingianum, polygonatum cyrtonema, polygonatum clavatum, polygonatum, prandium, polygonatum minor, polygonatum odoratum, polygonatum prolapseum, polygonatum longum, polygonatum glabrum, polygonatum macrosperma, polygonatum stipulatum, polygonatum brevifolium, polygonatum muticum, polygonatum stipulatum, polygonatum solomorpha, polygonatum bicolor, polygonatum nodosum, polygonatum folicum, polygonatum laeberry, polygonatum kingianum, polygonatum pentaphyllum, polygonatum convolvulus, polygonatum tenuifolium, polygonatum tenuipilatum, polygonatum hotriver, polygonatum Xinjiang, polygonatum sibiricum, polygonatum cyrto. In view of the planting resource condition of polygonatum plants, preferably, the polygonatum plants are one and/or more of polygonatum, polygonatum kingianum, polygonatum cyrtonema and polygonatum.
Further, the processed rhizoma polygonati is a multi-flower processed rhizoma polygonati. The polygonatum cyrtonema is used as a raw material to be steamed and aired to obtain a processed product, namely the polygonatum cyrtonema.
Further, the processed rhizoma Polygonati is prepared by steaming and sun-drying rhizoma Polygonati for nine times, steaming and sun-drying rhizoma Polygonati for eight times, steaming and sun-drying rhizoma Polygonati for seven times, and steaming and sun-drying rhizoma Polygonati for six times.
Further, the processed rhizoma polygonati is prepared by the following method:
removing impurities and fibrous roots from rhizoma Polygonati, cleaning, air drying, and slicing. And then placing the mixture into a steamer, covering a box, heating, adjusting the power of the steamer to be low after water in the steamer is boiled, starting timing, and steaming for 5-10 hours, preferably 4-7 hours, with slow fire.
After steaming, taking out the sealwort, putting the sealwort in a drying oven at 65-77 ℃, and taking out the sealwort after 10-15 hours, namely steaming and drying the sealwort in the sun. Repeating the above method for 6-9 times to obtain six times of rhizoma Polygonati, seven times of rhizoma Polygonati, eight times of rhizoma Polygonati, and nine times of rhizoma Polygonati.
Specifically, 10kg of fresh polygonatum cyrtonema is cleaned, aired and sliced into thick slices after impurities and fibrous roots are removed. And then placing the mixture in a steamer, reducing the power of the steamer after the water in the steamer is boiled, starting timing, and steaming for 6 hours with slow fire. After steaming, taking out the sealwort, putting the sealwort in a 70 ℃ oven, and taking out the sealwort after 12 hours, namely steaming and drying the sealwort. Repeating the above steps to obtain rhizoma Polygonati by steaming and sun drying.
Further, S1 includes the steps of: weighing processed rhizoma Polygonati, reflux-extracting with 5-15 times of water for 1-4 times (each for 1-5 hr), filtering, mixing extractive solutions, centrifuging to obtain supernatant, and concentrating to 5-10 times of rhizoma Polygonati to obtain concentrated solution.
Then, adding ethanol into the concentrated solution, adjusting the alcohol concentration to 35-45 v%, and centrifuging to obtain a first alcohol precipitate and a first alcohol precipitation supernatant. Adding ethanol into the supernatant of the first alcohol precipitation to adjust the alcohol concentration to 55-65 v%, centrifuging to obtain a second alcohol precipitation and a supernatant of the second alcohol precipitation, washing the second alcohol precipitation with ethanol with the volume concentration of more than 92 v% for 1-4 times, and volatilizing to remove the ethanol to obtain crude polygonatum galactan.
In a specific example, the step of extracting the polygonatum polysaccharides comprises the following steps: weighing 200g of rhizoma polygonati which is a multi-flower processed product, carrying out reflux extraction for 2 times by 10 times of water, carrying out 4 hours each time, filtering, combining extracting solutions, centrifuging to obtain a supernatant, and concentrating to 1300 mL. Adding 945mL of 95% ethanol into the concentrated solution until the ethanol concentration is 40%, and centrifuging to obtain 40% ethanol precipitate and 1000mL ethanol precipitation supernatant. Adding 1714mL of 95% ethanol into the supernatant of 40% ethanol precipitation under stirring, centrifuging to obtain 60% ethanol precipitate and supernatant of ethanol precipitation, washing the 60% ethanol precipitate with 95% ethanol for 3 times, and volatilizing the ethanol to obtain crude rhizoma Polygonati galactan.
In a specific example, the method for purifying the components with the weight-average molecular weight of 4000 Da-15000 Da in the polygonatum polysaccharide is selected from one or more of anion exchange column chromatography, gel exclusion column chromatography, dialysis and ultrafiltration.
Specifically, the crude polygonatum galactan component is redissolved by adding deionized water, a small amount of insoluble substances are removed by centrifugation, at least one of alcohol precipitation grading, gel exclusion chromatography, dialysis method or ultrafiltration method and other methods is selected for purification, the galactan-containing fluid fraction or trapped fluid or permeate is collected, and after desalination, direct vacuum freeze drying or reduced pressure concentration and alcohol precipitation and reduced pressure drying are carried out if salt is contained, so that the purified polygonatum galactan is obtained.
As will be readily understood by those skilled in the art, for Gel exclusion chromatography, Gel materials such as Sephadex series, Sepharose series, polyacrylamide Bio-Gel P series, and Gel fillers formed by cross-linking them with each other are appropriately selected according to the molecular weight of the polysaccharide substance in the polysaccharide fraction of Polygonatum sibiricum, and then the Gel fillers are subjected to column packing, sample loading, and sequential elution with a salt-containing or salt-free elution solution and fractions are collected according to the actual properties of each filler. Mixing all the eluate, concentrating or not concentrating, dialyzing in dialysis bag or ultrafiltering with ultrafiltration membrane, collecting the desalted retentate, and vacuum freeze drying or vacuum drying under reduced pressure to obtain purified rhizoma Polygonati galactan. Or purifying rhizoma Polygonati polysaccharide component by dialysis or ultrafiltration, and selecting ultrafiltration membrane with appropriate molecular weight for tangential flow ultrafiltration interception treatment. For example, the aqueous solution of the polygonatum polysaccharide component is fully dialyzed or ultrafiltered by a dialysis bag or an ultrafiltration membrane with the molecular weight larger than that of polygonatum galactan, the permeate or effluent is collected to remove substances with large molecular weight, then fully dialyzed or ultrafiltered by a dialysis bag or an ultrafiltration membrane with the molecular weight smaller than that of polygonatum galactan, the trapped fluid is collected, and the trapped fluid is concentrated and then subjected to vacuum freeze drying or vacuum reduced pressure drying to obtain the purified polygonatum galactan.
The invention also provides a structure analysis method of the polygonatum kingianum galactan, which comprises the following steps:
(1) and (3) measuring the molecular weight: taking a polygonatum sibiricum galactan sample, and adopting a high-efficiency gel exclusion chromatography-differential detector detection method.
(2) And (3) monosaccharide composition analysis, namely taking a polygonatum sibiricum galactan sample, partially hydrolyzing the polygonatum sibiricum galactan sample into monosaccharide by using acid with lower concentration, performing PMP derivatization, introducing into a chromatographic column such as C18, and analyzing the monosaccharide composition of the polygonatum sibiricum galactan by using a high performance liquid chromatograph.
(3) Methylation analysis: taking a polygonatum galactan sample, methylating polysaccharide by using a methyl halide reagent such as methyl iodide and the like under an alkaline condition, hydrolyzing under the alkaline condition, reducing by using sodium borohydride, acetylating methylated sugar alcohol by using anhydride, extracting to constant volume, analyzing by using a gas chromatograph combined with a mass spectrometer (GC-MS) to judge the glycosidic bond connection mode of the polygonatum galactan.
(4) Infrared spectrum analysis: and (3) taking a polygonatum galactomannan sample, fully drying, and measuring the infrared spectrum of the sample on an infrared spectrometer by adopting a solid potassium bromide tabletting method.
(5) Nuclear magnetic resonance analysis: dissolving a polygonatum sibiricum galactan sample in deuterated heavy water, freezing, vacuum-drying, repeating the heavy water exchange for three times, dissolving the polygonatum sibiricum galactan sample in the heavy water, and detecting the nuclear magnetic resonance spectrum of the sample to include one dimension1H and13c spectrum and1H-1H COSY、1H-1H TOCSY、1H-1H ROESY、1H-13C HSQC、1H-13c HMBC two-dimensional correlation spectrum.
(6) Analyzing comprehensive data: analyzing the analysis data of the steps comprehensively, and analyzing the chemical structure of the polygonatum sibiricum galactan.
According to the structure analysis method, the structure analysis is carried out on the polygonatum galactan extracted and purified from polygonatum cyrtonema by the preparation method. The result shows that the polygonatum galactan only shows one chromatographic peak with good symmetry on an HPGPC gel chromatographic peak, the weight-average molecular weight of the polygonatum galactan is 7kDa, and the polydispersity index of the polygonatum galactan is 1.15; monosaccharide composition shows that the polygonatum galactan consists of galactose; methylation analysis shows that the polygonatum galactan has beta (1 → 4) glycosidic bonds and beta (4,6 → 1) glycosidic bonds; infrared spectrum analysis displayThe absorption peaks of hydroxyl groups on the sugar ring and the absorption peak of pyranose absorption signal in the fingerprint spectrum all accord with the absorption peak of galactan; can clearly belong to polygonatum galactan according to nuclear magnetic resonance spectrum data1H and13c. Combining the above data, the polygonatum galactan has the structural characteristics shown in the general formula I: the main chain is beta (1 → 4) glycosidic bond, and the side chain galactose is connected to the main chain by beta (1 → 6) glycosidic bond.
In the formula (I), n represents the number of sugar repeating units, and n is a natural number.
According to the structure analysis method of the present invention, polygonatum plants contain polygonatum galactan having a structure represented by chemical formula II.
Apparently, the polygonatum galactan with the structure shown in chemical formula II is the structure of the polygonatum galactan shown in general formula I when n is 1.
According to the invention, pharmacological research shows that the polygonatum galactan can promote the proliferation of probiotics and has a remarkable effect within 2 to 12 hours; with the increase of the drug concentration, the capability of the polygonatum galactan for promoting the probiotics is obviously enhanced, which shows that the polygonatum galactan can promote the proliferation of the probiotics. Therefore, the polygonatum galactan with a novel structure has the function of promoting the proliferation of probiotics, and has the practical application value of regulating the intestinal flora.
Therefore, the invention further provides application of the polygonatum galactan in preparation of medicines and/or foods for regulating intestinal flora, promoting digestion and enhancing intestinal peristalsis.
The pharmaceutical composition provided by the embodiment of the invention comprises the polygonatum galactan and pharmaceutically acceptable salts or pharmaceutically acceptable solvates thereof and pharmaceutically and/or food acceptable auxiliary materials. Optionally, the adjuvant comprises a pharmaceutical excipient, a carrier and/or a diluent and/or a flavoring agent, etc.
In a specific example, the dosage form of the pharmaceutical composition is an injection or a solid preparation, such as a water injection, a freeze-dried powder injection for injection, a capsule, an effervescent agent and the like, and the auxiliary material comprises an excipient and/or a flavoring agent and the like.
The invention also provides application of the pharmaceutical composition in preparing medicines and/or functional foods for regulating intestinal flora, promoting digestion and enhancing intestinal peristalsis.
The present invention will be described in detail with reference to specific embodiments in the following drawings, which should not be construed as limiting the scope of the claims of the present invention.
Example 1 extraction and purification of Polygonatum sibiricum galactan
1. Extraction of crude polysaccharide from rhizoma Polygonati
10kg of fresh polygonatum cyrtonema is cleaned, aired and sliced into thick slices after impurities and fibrous roots are removed. And then placing the mixture in a steamer, reducing the power of the steamer after the water in the steamer is boiled, starting timing, and steaming for 6 hours with slow fire. After steaming, taking out the sealwort, putting the sealwort in a 70 ℃ oven, and taking out the sealwort after 12 hours, namely steaming and drying the sealwort. Repeating the above steps to obtain rhizoma Polygonati by steaming and sun drying.
Reflux-extracting 200g of the processed Polygonatum cyrtonema with 10 times of water for 2 times, filtering, mixing the extracting solutions, centrifuging to obtain a supernatant, and concentrating to obtain 1300mL of a concentrated solution. 95% ethanol 945mL was added to reach an alcohol concentration of 40%, and the mixture was centrifuged (4000 rpm. times.15 min) to obtain a 40% alcohol precipitate and a supernatant. Adding 1714mL 95% ethanol into the supernatant after 40% ethanol precipitation under stirring until the alcohol concentration reaches 60%, centrifuging (4000rpm × 15min) to obtain 60% ethanol precipitate and supernatant, washing 60% ethanol precipitate with 95% ethanol for 3 times, and volatilizing alcohol to obtain crude rhizoma Polygonati galactan.
2. Purification of polygonatum sibiricum galactan
Dissolving the crude rhizoma Polygonati galactan in deionized water, loading onto DEAE-52(3.2cm × 30cm) weak anion exchange column, eluting with deionized water and 0.1, 0.5 and 1.0M NaCl solution, and collecting eluate about 10mL per tube. Detecting by phenol-sulfuric acid method, drawing an outflow curve, collecting the flow, concentrating under reduced pressure, and freeze-drying under vacuum to obtain 1.78g of purified rhizoma Polygonati galactan.
Example 2 Structure analysis of Polygonatum sibiricum galactan
1. Procedure of experiment
1.1. Molecular weight and distribution thereof
The molecular weight and distribution of the polygonatum galactan prepared in example 1 were analyzed by high performance gel exclusion chromatography-differential detector assay (HPGPC-RI).
Chromatography apparatus: agilent technologies 1260series high performance liquid chromatograph;
chromatographic conditions are as follows: shodex Ohpak SB-804HQ (7.8 mm. times.300 mm) column; the column temperature was 35 ℃; a difference detector; the mobile phase is 0.1M NaCl, and the flow rate is 0.5 mL/min;
the determination process comprises the following steps: adding mobile phase into 5mg/mL galactan sample or dextran reference substance with known molecular weight to obtain 5mg/mL solution, filtering with 0.22 μm microporous membrane, analyzing with high performance liquid chromatograph, and recording chromatogram. And processing the data by adopting GPC software, drawing a standard curve, substituting the data into an equation, and calculating the molecular weight.
1.2 monosaccharide composition analysis
Dissolving 2.0mg of galactomannan in water to 2mg/mL, dissolving 300 μ L in 4M trifluoroacetic acid solution, and charging N2Sealing the tube, carrying out hydrolysis reaction for 4h at 110 ℃, evaporating the hydrolysate to dryness in a water bath kettle at 70 ℃, and removing trifluoroacetic acid. Adding 100 μ L of water to dissolve the evaporated material, adding 50 μ L of 0.6M sodium hydroxide solution and 100 μ L of 0.5M 3-methyl-1-phenyl-2-pyrazoline-5-ketone (PMP) methanol solution, vortex mixing, performing derivatization reaction in a 70 ℃ oven for 60min, cooling to room temperature after the reaction is finished, adding 100 μ L of 0.3M hydrochloric acid solution for neutralization, adding 500 μ L of chloroform into the solution for extraction, centrifuging (15000rpm × 15min), filtering with a 0.22 μ M microporous membrane, and performing chromatographic analysis.
Chromatographic conditions are as follows: the instrument comprises the following steps: agilent technologies 1260series high performance liquid chromatograph; a chromatographic column: agilent ZORBAX SB C18(150 mm. times.4.6 mm, 5 μm); the column temperature is 30 ℃; the mobile phase is 0.1M ammonium acetate (pH 5.5) buffer acetonitrile (83: 17); flow rate: 1 mL/min; the injection volume is 20 mu L; DAD detector, detection wavelength 250 nm.
1.3 methylation analysis
Methylation reaction: weighing 10mg of a polygonatum sibiricum galactan sample, dissolving the polygonatum sibiricum galactan sample in 4mL of DMSO (dimethylsulfoxide), sequentially adding 100mg of sodium hydroxide and 600 mu L of methyl iodide, and filling nitrogen to perform ultrasonic reaction for 1 hour. After the reaction is finished, 2mL of pure water is added, the pH value of the solution is adjusted to be neutral by using 1M hydrochloric acid solution, 6mL of trichloromethane is added to extract a sample after methylation, and an organic phase is taken, dried at 40 ℃ under reduced pressure and dried in vacuum for 12h to remove the organic solvent.
Acid hydrolysis: the dried sample was dissolved in 2mL of 2M TFA solution, and the tube was sealed and hydrolyzed at 120 ℃ for 5 h.
Reduction: and (3) adjusting the pH value of the hydrolysate to 10-12 by using 1M NaOH, adding 50mg of sodium borohydride, stirring in a water bath at 50 ℃ for 2 hours, adding 250 mu L of glacial acetic acid to stop the reaction, and freeze-drying the reaction solution.
Acetylation: 1mL of pyridine and 1mL of acetic anhydride were added to the above lyophilized sample in a test tube, and the tube was sealed at 100 ℃ for reaction for 1 hour. After cooling, 1mL of water are added, 2mL portions of dichloromethane are extracted 3 times, and the organic phase is extracted with N2After blowing, 100. mu.L of methylene chloride was added to dissolve the residue, and GC-MS analysis was performed.
GC conditions were as follows: HP-5MS quartz capillary column (50 mm. times.0.25 mm, 0.25 μm); column temperature: the initial temperature is 80 ℃, the temperature is kept for 11min, the temperature is programmed to be 5 ℃/min to 250 ℃, and the temperature is kept for 5 min; the carrier gas is high-purity helium; the carrier gas flow is 1.5 mL/min; the temperature of a sample inlet is 270 ℃; column front pressure 100 KPa; no flow diversion; sample introduction amount: 2 μ L.
MS conditions: an ionization mode EI; electron energy 70; the transmission line temperature is 290 ℃; the ion source temperature is 230 ℃; the temperature of the quadrupole rods is 150 ℃; the mass range is 50-600; and (4) adopting a CCRC standard spectrum library computer to search and determine the quality.
1.4 Infrared Spectroscopy
According to the fourth part of 2020 edition Chinese pharmacopoeia, a solid tabletting method is adopted: taking 2mg of a sample, vacuum-drying the sample for 24 hours at 40 ℃, adopting a KBr tabletting method, and carrying out 4000-400 cm on the sample by using a Tensor 27 Fourier transform mid-infrared spectrometer-1Scanning and recording a spectrogram.
1.5 nuclear magnetic resonance analysis
Dissolving 10mg of rhizoma Polygonati galactan sample in 0.5mL of D2In O, freeze-drying, D2After three O-exchanges, the freeze-dried sample was dissolved in 0.5mL of D2O (99.9 atom% D, containing 0.05 wt.% 3- (trimethylsilyl) propionic-2,2,3,3-D as an internal standard4acid, sodium salt). Measurement with Bruker 800MHz NMR spectrometer1H/13C NMR spectrum and two-dimensional spectrum (1H-1H COSY、1H-1H TOCSY、1H-1H ROESY、1H-13C HMBC and1H-13c HSQC), analyzed using MestReNova software.
2. Results of the experiment
The properties of the polygonatum galactan are as follows: white or off-white solid, tasteless, easily soluble in water, slightly soluble in organic solvents such as ethanol, etc., and has hygroscopicity.
The analysis result of high performance gel exclusion chromatography shows (figure 1), the manyflower solomonseal rhizome galactan only has a symmetrical chromatographic peak, the weight average molecular weight (Mw) is 7019Da, and the polydispersity index is 1.14.
The analysis result of monosaccharide composition shows (figure 2), the HPLC chart of the rhizoma polygonati galactan after PMP pre-column derivatization shows that only one galactose peak exists, which indicates that the rhizoma polygonati galactan monosaccharide composition only contains galactose.
Methylation analysis results show that the polygonatum galactan has beta (1 → 4) galactose glycosidic bonds, beta (1 → 4,6) galactose glycosidic bonds and beta (→ 1) galactose glycosidic bonds.
Infrared Spectrum (cm)-1) The data (fig. 3) are: 3416cm-1The characteristic absorption of the O-H stretching vibration of the hydroxyl on the sugar ring is realized; 2922 to 2897cm-1Stretching and vibrating methylene C-H on a sugar ring; 1025cm-1C-O-C stretching vibration on the sugar ring; 889cm-1Is the configurational characteristic absorption of beta-type monosaccharide.
The results of the NMR analysis are shown in FIGS. 4 and 5, and are described in detail1H and13the C NMR signals are assigned in tables 1 and 2. Proton chemical shift 4.65ppm, 4.61ppm and 4.46ppm are respectively 1, 4-beta-D-galactose (1, 4-beta-D-Galp, abbreviated as B), 1,4, 6-beta-D-galactose (1,4, 6-beta-D-Galp, abbreviated as D) and 1-beta-D-galactose (1-beta-D-Galp, abbreviated as A)1H proton signal, 4.19ppm for the 4-position (H-4) proton signal of 1,4- β -D-Galp and 80.5ppm for its corresponding C-4 chemical shift; the 4-position (H-4) and 6-position proton signals of 1,4, 6-beta-D-Galp were 4.22ppm and 3.90ppm (4.12ppm), respectively, and their corresponding chemical shifts of C-4 and C-6 were 80.5ppm and 73.1 ppm. The chemical shifts are shifted significantly towards a lower field relative to the corresponding chemical shift for unsubstituted galactose, indicating that the hydroxyl groups at positions 1 and 4 of galactosyl group B are substituted and the hydroxyl groups at positions 1,4 and 6 of galactosyl group D are substituted. The coupling constant of anomeric C-H of galactosyl group B is 148Hz, indicating that its anomeric configuration should be beta-type. In the NMR spectrum, there were 3 anomeric hydrogen signals (chemical shift values were all less than 4.90ppm), 3 anomeric carbon signals from low to high were 106.5, 107.1 and 107.2ppm, respectively, corresponding to C-1 of 1- β -D-galactose (1- β -D-Galp), 1,4,6- β -D-galactose (1,4,6- β -D-Galp) and 1,4- β -D-galactose (1,4- β -D-Galp), respectively, indicating that the anomeric configurations of the three glycosyl fragments were all β -type.1H and13the C remote correlation HMBC spectra clearly showed that there were significant signals associated with H-1 of galactosyl A (A1) and C-6 of D (D6) (FIG. 5), while H-1 of galactosyl B (B1) and C-4 of galactosyl D (D4), H-1 of galactosyl D (D1) and C-4 of galactosyl B (B4), H-4 of galactosyl B (B4) and C-1 of galactosyl A (A1). Thus, the linkage of galactan is: galactosyl B forms the main chain with β (1 → 4) glycosidic bond, and galactosyl A is linked to galactosyl D at position 6 with β (1 → 6) glycosidic bond.
The above data show that the chemical structural formula of the sealwort galactan with the novel structure is shown as the general formula I.
In the formula (I), n represents the number of sugar repeating units, and n is a natural number.
The structure is characterized in that: (1) the polygonatum galactomannan is galactan with a new structure extracted from rhizome of polygonatum; (2) the monosaccharide connection mode of the polygonatum sibiricum galactan is as follows: the main chain is beta (1 → 4) glycosidic bond, and the side chain galactose is connected to the main chain by beta (1 → 6) glycosidic bond. Through the retrieval of published documents at home and abroad, the arrangement mode and the chemical structure of the polygonatum kingianum galactan are not reported in a public way and are discovered by the inventor for the first time.
TABLE 1 preparation of Polygonatum sibiricum galactan1Assignment of H NMR
| 1-β-D-Galp(A) | 1,4-β-D-Galp(B) | 1,4,6-β-D-Galp(D) | |
| H-1 | 4.46 | 4.65 | 4.61 |
| H-2 | 3.62 | 3.69 | 3.53 |
| H-3 | 3.67 | 3.79 | 3.79 |
| H-4 | 3.95 | 4.19 | 4.22 |
| H-5 | 3.73 | 3.67 | 4.00 |
| H-6 | 3.83 | 3.73，3.85 | 3.90，4.12 |
TABLE 2 preparation of Polygonatum sibiricum galactan13Assignment of C NMR
Note:
wherein 1- β -D-Galp represents β -D-Galp- (1 →;
1,4- β -D-Galp means → 4) - β -D-Galp- (1 →;
1,4,6- β -D-Galp means → 4,6) - β -D-Galp- (1 →.
Example 3 promotion of growth of probiotic bacteria by Polygonatum sibiricum galactan
1. Test article, reagent and strain
A polygonatum galactan, abbreviated PP1, galactan prepared according to example 1; sugar-free de Man-Rogosa-Sharpe (MRS) Medium, Inc., Coolaber, Beijing; the 4 strains are respectively Bifidobacterium animalis subsp.
2. Experimental methods
2.1 preparation of the solution
600mg and 700mg of Glucose (Glucose) in FOS and PP1 are weighed, prepared into 10mg/mL solutions with sterile water, and each solution is added into a sugar-free MRS culture medium at a concentration of 5mg/mL after being filtered by a 0.22-micron sterile filter in a clean bench. 56mL of sterilized MRS medium was taken, and 56mL of sterile water was added to dilute the filtered sample, followed by mixing to prepare 5mg/mL of MRS medium. Bifidum and L.plantarum on the corresponding medium 1X 107Amounts of CFU/mL, B.animalis subsp.lactis and L.acidophilus were inoculated at 1X 10 onto the respective media8Amount of CFU/mL.
2.2 bacterial culture
Bacteria culture medium: MRS (L-cysteine) medium contains 0.05% of L-cysteine;
and (3) recovering bacteria: prepare 1 relative liquid medium and 2 plates, make a circle at 1/2 on the tube body with a small emery wheel in a clean bench, then wipe the tube wall with 75% alcohol, and break with tweezers. Injecting 0.3-0.5mL of liquid culture medium into a freeze-drying tube, gently blowing and uniformly mixing, fully dissolving into bacterial suspension, sucking 1/3, adding into the liquid culture medium, averagely adding the rest onto 2 plates, and culturing under corresponding conditions until bacterial colonies grow out.
And (3) expanding bacteria: individual colonies were picked from the plates and cultured on a shaker at 37 ℃ in liquid medium.
Seed preservation: centrifuging 25mL of bacterial solution at 4 deg.C (4100rmp × 10min), removing supernatant, adding 2.5mL of liquid culture medium, suspending the precipitate, adding glycerol of the same volume, mixing, and freezing at-80 deg.C.
2.3 cultivation of the respective bacterial culture Medium
Each bacterial strain was placed in an anaerobic environment (85% N)2,10％CO2And 5% of H2Volume concentration) and samples were taken at 0h, 2h, 4h, 6h, 8h, 12h, 24h, 36h and 48h time points.
2.4 detection of pH
The culture broth was removed at each sampling time point, in triplicate, and after centrifugation (4000 rpm. times.10 min), the pH was determined 3 times per time point.
2.4 detection of OD values
The culture broth was taken out at each sampling time point, in parallel, in triplicate, shaken up and down for 15s, poured into a cuvette, and the OD was determined with an ultraviolet spectrophotometer at a wavelength of 600nm, 3 times per time point.
2.6 detection of the number of bacteria
The culture medium was taken out at each sampling time point, in triplicate, shaken up and down for 15s, from which a certain amount of culture medium was taken out, diluted by a certain multiple and counted on a hemocytometer for 3 times per time point.
3. Results of the experiment
3.1 Effect on the pH value in the culture Medium of the respective bacteria
As shown in figure 6, the pH value of the polygonatum galactan and other treatment groups is reduced to different degrees compared with that of the blank group, which shows that the pH value of the culture medium is obviously reduced because short-chain fatty acid metabolites such as lactic acid, acetic acid and the like of each bacterial strain are increased in the presence of polygonatum galactan, fructo-oligosaccharide and glucose.
3.2 Effect on OD value in culture Medium for respective bacteria
As shown in FIG. 7, the OD values of the culture solutions cultured in different media were increased rapidly in the whole range from 0 to 12 hours, and the OD values of the culture solutions remained substantially unchanged after 12 hours; the OD values of the polygalactose, fructo-oligosaccharide and glucose groups of the sealwort are all obviously higher than that of the blank in corresponding time. The polygalactose, fructo-oligosaccharide and glucose of sealwort can promote the proliferation of each bacterial strain, and the proliferation amount of the bacteria treated by the polygalactose of sealwort is obviously different from that of a blank group (P < 0.01).
3.3 Effect on the number of bacterial strains in the respective bacterial media
As shown in figure 8, in the culture medium containing polygonatum galactan, 4 bacterial strains enter an exponential phase within 2-12 hours and quickly proliferate; the proliferation conditions of 4 different strains are different according to the strains, and the proliferation promoting activity of the bifidobacterium animalis subsp.
The results prove that the polygonatum galactan has remarkable activity of promoting the growth of probiotics, and therefore, the polygonatum galactan with the novel structure has practical application values of improving intestinal flora, promoting digestion and enhancing intestinal peristalsis.
Example 4 preparation of lyophilized powder for injection of Polygonatum sibiricum and galactan
1. Material
The polygonatum galactan obtained by the same method as the example 1 and the pharmaceutical grade sodium chloride.
2. Prescription
| Name of raw and auxiliary materials | Dosage of |
| Rhizoma Polygonati galactan | 50g |
| Sodium chloride | 4.5g |
| Water for injection | 500mL |
| Are co-produced into | 1000 pieces |
3. Preparation process
Weighing the formula amount of polygonatum galactomannan and sodium chloride, adding water for injection to full amount, stirring to dissolve completely, and sterilizing by an intermittent hot pressing method. Adding 0.3% medicinal active carbon, and stirring for 20 min; the heat source was removed by decarburizing filtration using a Buchner funnel and a 3.0 μm microporous membrane. Filtering with 0.22 μm microporous membrane after the content is qualified; and (3) subpackaging into tube-type penicillin bottles, wherein each bottle is 0.5mL, half plugging, placing into a freezing and drying box, performing freeze drying according to a set freeze drying curve, plugging, taking out of the box, rolling a cover, performing visual inspection to obtain a qualified product, and packaging to obtain a finished product.
And (3) freeze-drying: putting the sample into a box, cooling the temperature of a partition plate to-40 ℃, and keeping for 4 hours; the cold trap was lowered to-50 ℃ and vacuum was started to 250 μ bar. Starting sublimation: heating to-20 deg.C at constant speed for 1h, and maintaining for 3 h; heating to-10 ℃ at constant speed for 3h, keeping for 8h, and keeping in vacuum for 100-250 μ bar; and then drying: heating to-5 ℃ for 2h, keeping for 2h, and keeping the vacuum state at 150-200 mu bar; heating to 10 ℃ within 0.5h, keeping for 2h, and keeping vacuum at 80-100 μ bar; heating to 40 deg.C for 0.5h, maintaining for 4h, and vacuum pumping to minimum.
Example 5 preparation of Polygonatum sibiricum galactan capsules
1. Material
The polygonatum galactan obtained by the method in the example 1, food or medicine grade starch.
2. Prescription
| Name of raw and auxiliary materials | Dosage of |
| Rhizoma Polygonati galactan | 300g |
| Starch | 500g |
| Are co-produced into | 5000 granules |
3. Preparation process
Weighing the polygonatum galactomannan and the starch according to the prescription amount, and stirring to completely mix. Adding appropriate amount of pulvis Talci, granulating with ethanol by wet method, sieving, drying, and packaging into number 2 capsule shell, and filling 60mg of rhizoma Polygonati galactan into each capsule body to obtain rhizoma Polygonati galactan capsule.
Example 6 preparation of Polygonatum sibiricum galactan oral liquid
1. Material
The polygonatum galactomannan obtained by the method of the embodiment 1, the food or medicine grade flavoring agent and the caramel essence.
2. Prescription
| Name of raw and auxiliary materials | Dosage of |
| Rhizoma Polygonati galactan | 50g |
| Sucrose | 0.3g |
| Caramel essence | 0.05g |
| Purified water | 1000mL |
| Are co-produced into | 500 pieces |
3. Preparation process
Weighing the polygonatum galactomannan, the sucrose and the caramel essence according to the prescription amount, adding purified water to completely dissolve, filtering by a 0.22 mu m microporous filter membrane, filling the filtrate according to the amount of 2mL per bottle by an oral liquid filling machine, sealing and sterilizing to obtain the sealwort health-care beverage.
Example 7 preparation of Polygonatum sibiricum galactan facial cleanser
1. Material
The polygonatum galactan obtained by the method in the example 1 adopts cosmetic-grade or food-grade raw materials.
2. Prescription
7g of polygonatum galactan, 2.0g of glycerol, 4.0g of butanediol, 0.5g of propylene glycol, 0.1g of EDTA sodium, 0.3g of guar gum, 2.0g of zinc dioxide, 4.0g of C12-15 alcohol benzoate, 3.0g of C12-20 alkyl glucoside, 0.5g of C14-22 alcohol, 1.2g of cetearyl alcohol, 0.2g of nipagin ester, 0.3g of sodium stearate, 0.5g of dimethiconol, 0.2g of polysorbate and 55g of deionized water.
3. Preparation process
Weighing the polygonatum galactan according to the prescription amount, and adding purified water to completely dissolve the polygonatum galactan; dissolving glycerol, butanediol, propylene glycol, sodium EDTA, guar gum, zinc dioxide, sodium stearate, C12-15 alcohol benzoate, C12-20 alkyl glucoside, C14-22 alcohol, and cetearyl alcohol in purified water; taking the nipagin ester, the dimethiconol and the polysorbate, and adding purified water to completely dissolve. Mixing the above solutions, stirring, filtering with 0.22 μm microporous membrane, bottling the filtrate 30mL per bottle, sealing, and sterilizing.
Example 8 preparation of a Polygonatum sibiricum galactan mask
1. Material
The polygonatum galactan obtained by the method in the example 1 adopts cosmetic-grade or food-grade raw materials.
2. Prescription
12g of polygonatum galactomannan, 3.5g of transparent xanthan gum, 2.0g of hydrolyzed hyaluronic acid, 2.0g of sodium hyaluronate, 0.3g of propylene glycol, 0.5g of carbomer, 0.1g of nipagin ester, 0.25g of PPG-10 methyl glucose ether, 1.0g of glycerol glucoside and 45g of deionized water.
3. Preparation process of facial mask
And 2, adjusting the pH value to 7.6 +/-0.2.
And 3, continuously cooling to 35 ℃, adding PPG-10 methyl glucose ether, rhizoma polygonati galactan and glycerol glucoside, continuously stirring uniformly, and discharging after the inspection is qualified. The coating was applied to a nonwoven substrate at a weight of 2.1g per square centimeter.
The descriptions of each patent, patent application, and publication cited in this application are incorporated herein by reference in their entirety. Citation of any reference shall not be construed as an admission that such reference is available as "prior art" to the present application.
The technical features of the embodiments described above may be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the embodiments described above are not described, but should be considered as being within the scope of the present specification as long as there is no contradiction between the combinations of the technical features.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (11)
1. A polygonatum galactan is characterized in that the polygonatum galactan has a structure represented by the following general formula I:
in the formula (I), n represents the number of sugar repeating units, and n is a natural number.
2. The polygonatum galactan according to claim 1, wherein the polygonatum galactan has a weight average molecular weight of 4000-15000 Da and a polydispersity of 1-3.
3. The preparation method of the polygonatum galactan according to any one of claims 1 to 2, which is characterized by comprising the following steps:
extracting crude polysaccharide of rhizoma Polygonati from rhizoma Polygonati;
purifying and separating components with the weight average molecular weight of 4000 Da-15000 Da in the crude polygonatum sibiricum polysaccharide to obtain the polygonatum sibiricum galactan.
4. The preparation method of polygonatum galactan according to claim 3, which is characterized by comprising the following steps:
step 1, extracting crude polysaccharide of the processed rhizoma polygonati under the alcohol concentration of 50-65 v% to obtain rhizoma polygonati crude polysaccharide;
and 2, purifying and separating components with the weight-average molecular weight of 4000 Da-15000 Da in the crude polygonatum sibiricum polysaccharide to obtain the polygonatum sibiricum galactan.
5. The method for preparing polygonatum galactan according to claim 3, wherein the processed polygonatum is obtained by steaming and sun-drying polygonatum plants for 6-9 times.
6. The method for preparing polygonatum galactan according to any one of claims 4 or 5, wherein the processed polygonatum is subjected to hot water extraction, then the polygonatum polysaccharides are respectively subjected to ethanol fractional precipitation so that the alcohol concentrations of the polygonatum polysaccharides respectively reach 36-45 v% and 55-65 v%, and then the precipitates are centrifugally collected when the alcohol concentration reaches 55-65 v%. Preferably, the ethanol concentration in the two times is 40% and 60%, respectively.
7. The method for preparing polygonatum galactan according to any one of claims 4 or 5, wherein the step 2, the purification and separation process are selected from one or more of gel exclusion chromatography column method, dialysis method and ultrafiltration method.
8. The method according to claim 5, wherein the Polygonatum plant comprises one or more of Polygonatum sibiricum Red, Polygonatum cyrtonema Hua, Polygonatum sibiricum Red, Polygonatum cyrtonema Hua, Polygonatum odoratum, Polygonatum Candin, Polygonatum Candidatum, Polygonatum Cannabifolium, Polygonatum Canaliculatum, Polygonatum Cannabifolium, Polygonatum Sibiraeanum, Polygonatum Cannabifolium, Polygonatum Canaliculatum, Polygonatum sibiricum Red, Polygonatum Cantonese, Polygonatum Candidatum Canaliculatum, Polygonatum Canalic.
9. A pharmaceutical composition comprising an effective amount of the polygonatum galactan of claim 1 or 2.
10. The pharmaceutical composition of claim 9, wherein the pharmaceutical composition is in the form of lyophilized powder, oral liquid or capsule.
11. Use of the pharmaceutical composition according to claim 9 or the polygonatum galactan according to any one of claims 1-2 in the preparation of a food and/or a medicament for regulating the gastrointestinal flora, promoting intestinal motility and promoting digestion; or the rhizoma polygonati fructan is applied to the preparation of facial masks, cosmetics or daily chemicals.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110256434.8A CN113024681B (en) | 2021-03-09 | 2021-03-09 | Polygonatum sibiricum galactan and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110256434.8A CN113024681B (en) | 2021-03-09 | 2021-03-09 | Polygonatum sibiricum galactan and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN113024681A true CN113024681A (en) | 2021-06-25 |
| CN113024681B CN113024681B (en) | 2023-07-28 |
Family
ID=76467419
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110256434.8A Active CN113024681B (en) | 2021-03-09 | 2021-03-09 | Polygonatum sibiricum galactan and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113024681B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113670845A (en) * | 2021-06-28 | 2021-11-19 | 湖南省中医药研究院 | Kit for rapidly detecting activity of probiotics and detection method thereof |
| CN117209620A (en) * | 2023-09-22 | 2023-12-12 | 中国科学院昆明植物研究所 | Purslane galactoglucan and composition thereof, and preparation method and application thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105218692A (en) * | 2014-06-05 | 2016-01-06 | 上海家化联合股份有限公司 | The application of a kind of sealwort paragalactan and preparation method thereof and inhibited apoptosis |
-
2021
- 2021-03-09 CN CN202110256434.8A patent/CN113024681B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105218692A (en) * | 2014-06-05 | 2016-01-06 | 上海家化联合股份有限公司 | The application of a kind of sealwort paragalactan and preparation method thereof and inhibited apoptosis |
Non-Patent Citations (3)
| Title |
|---|
| 刘柳等: "黄精中的多糖组分及其免疫活性", 《中草药》, vol. 37, no. 8, pages 1132 - 1134 * |
| 黄镭等: ""黄精多糖益生元糕的研制及其品质分析"", 《食品工业》 * |
| 黄镭等: ""黄精多糖益生元糕的研制及其品质分析"", 《食品工业》, vol. 41, no. 3, 20 March 2020 (2020-03-20), pages 90 - 94 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113670845A (en) * | 2021-06-28 | 2021-11-19 | 湖南省中医药研究院 | Kit for rapidly detecting activity of probiotics and detection method thereof |
| CN113670845B (en) * | 2021-06-28 | 2024-05-17 | 湖南省中医药研究院 | Kit for rapidly detecting activity of probiotics and detection method thereof |
| CN117209620A (en) * | 2023-09-22 | 2023-12-12 | 中国科学院昆明植物研究所 | Purslane galactoglucan and composition thereof, and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN113024681B (en) | 2023-07-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Luan et al. | Extraction, purification, structural characteristics and biological properties of the polysaccharides from Codonopsis pilosula: A review | |
| CN109400734A (en) | A kind of Polysaccharides from Rosa roxburghii and the preparation method and application thereof | |
| CN102633901B (en) | Spirulina phatensis polysaccharide and extraction method thereof | |
| Huang et al. | Extraction, purification, structural characterization, and gut microbiota relationship of polysaccharides: A review | |
| CN113024681B (en) | Polygonatum sibiricum galactan and preparation method and application thereof | |
| KR101339706B1 (en) | A compound for immune strengthen inclusion reducing the bitterness of red ginseng, the extract of immune, and the probiotics | |
| CN105859903B (en) | radix glehniae polysaccharide and preparation method and application thereof | |
| CN106668321A (en) | Preparation method of radix ginseng and Chinese wolfberry fruit composition, and product and application thereof | |
| Zhu et al. | Characterizations of glucose-rich polysaccharides from Amomum longiligulare TL Wu fruits and their effects on immunogenicities of infectious bursal disease virus VP2 protein | |
| CN102408494A (en) | Grifola frondosa polysaccharide ZZK component and preparation method thereof | |
| US12023349B2 (en) | Method for extracting Lactarius Hatsudake Tanaka polysaccharide compound | |
| CN109320626B (en) | Aloe polysaccharide and preparation method and application thereof | |
| CN114807270B (en) | Burdock root polysaccharide prepared by fermenting rhizopus nigricans, and production process and application thereof | |
| CN116875507A (en) | Wessella-J4-1 fusion and application of extracellular polysaccharide thereof in prevention and treatment of colon cancer | |
| CN114042049B (en) | Preparation method of freeze-dried quick-release preparation of fresh rhizoma polygonati | |
| CN116284468A (en) | Tremella aurantialba acidic polysaccharide, preparation method thereof and application thereof in improving ulcerative colitis | |
| CN113004433A (en) | Rhizoma polygonati fructan and preparation method and application thereof | |
| CN102626418B (en) | Application of pyrola polysaccharide in preparing immunity-enhancing medicaments and health food | |
| CN110229244B (en) | Ramaria polysaccharide and preparation method and application thereof | |
| CN113633689A (en) | Oligogalacturonan traditional Chinese medicine composite preparation, preparation method and application | |
| CN113461832B (en) | Bacillus calmette-guerin mannan, preparation method and application thereof | |
| CN112042846A (en) | Sea-buckthorn solid beverage for enhancing immunity and inhibiting tumors and preparation method thereof | |
| CN117567657A (en) | Paris polyphylla glucomannan and preparation method and application thereof | |
| CN117567658A (en) | Paris polyphylla glucomannan and preparation method and application thereof | |
| CN111620957A (en) | Chinese yam polysaccharide, preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |