CN117088998A - Phosphorylated chicory oligosaccharide and preparation method thereof - Google Patents
Phosphorylated chicory oligosaccharide and preparation method thereof Download PDFInfo
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- CN117088998A CN117088998A CN202310905309.4A CN202310905309A CN117088998A CN 117088998 A CN117088998 A CN 117088998A CN 202310905309 A CN202310905309 A CN 202310905309A CN 117088998 A CN117088998 A CN 117088998A
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- chicory
- oligosaccharide
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- polysaccharide
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- 241000723343 Cichorium Species 0.000 title claims abstract description 66
- 235000007542 Cichorium intybus Nutrition 0.000 title claims abstract description 65
- 150000002482 oligosaccharides Chemical class 0.000 title claims abstract description 64
- 229920001542 oligosaccharide Polymers 0.000 title claims abstract description 62
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 150000004676 glycans Chemical class 0.000 claims abstract description 23
- 229920001282 polysaccharide Polymers 0.000 claims abstract description 23
- 239000005017 polysaccharide Substances 0.000 claims abstract description 23
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000006366 phosphorylation reaction Methods 0.000 claims abstract description 19
- 230000026731 phosphorylation Effects 0.000 claims abstract description 17
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 11
- 235000019832 sodium triphosphate Nutrition 0.000 claims abstract description 9
- 238000004108 freeze drying Methods 0.000 claims abstract description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims abstract description 6
- 238000001816 cooling Methods 0.000 claims abstract description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 claims abstract description 6
- 235000011152 sodium sulphate Nutrition 0.000 claims abstract description 6
- 238000011033 desalting Methods 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 5
- 239000010452 phosphate Substances 0.000 claims description 5
- 230000000865 phosphorylative effect Effects 0.000 claims description 5
- 239000007857 degradation product Substances 0.000 claims description 4
- 238000002390 rotary evaporation Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229920001202 Inulin Polymers 0.000 claims description 2
- JYJIGFIDKWBXDU-MNNPPOADSA-N inulin Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@]1(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(OC[C@]%12(OC[C@]%13(OC[C@]%14(OC[C@]%15(OC[C@]%16(OC[C@]%17(OC[C@]%18(OC[C@]%19(OC[C@]%20(OC[C@]%21(OC[C@]%22(OC[C@]%23(OC[C@]%24(OC[C@]%25(OC[C@]%26(OC[C@]%27(OC[C@]%28(OC[C@]%29(OC[C@]%30(OC[C@]%31(OC[C@]%32(OC[C@]%33(OC[C@]%34(OC[C@]%35(OC[C@]%36(O[C@@H]%37[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O%37)O)[C@H]([C@H](O)[C@@H](CO)O%36)O)[C@H]([C@H](O)[C@@H](CO)O%35)O)[C@H]([C@H](O)[C@@H](CO)O%34)O)[C@H]([C@H](O)[C@@H](CO)O%33)O)[C@H]([C@H](O)[C@@H](CO)O%32)O)[C@H]([C@H](O)[C@@H](CO)O%31)O)[C@H]([C@H](O)[C@@H](CO)O%30)O)[C@H]([C@H](O)[C@@H](CO)O%29)O)[C@H]([C@H](O)[C@@H](CO)O%28)O)[C@H]([C@H](O)[C@@H](CO)O%27)O)[C@H]([C@H](O)[C@@H](CO)O%26)O)[C@H]([C@H](O)[C@@H](CO)O%25)O)[C@H]([C@H](O)[C@@H](CO)O%24)O)[C@H]([C@H](O)[C@@H](CO)O%23)O)[C@H]([C@H](O)[C@@H](CO)O%22)O)[C@H]([C@H](O)[C@@H](CO)O%21)O)[C@H]([C@H](O)[C@@H](CO)O%20)O)[C@H]([C@H](O)[C@@H](CO)O%19)O)[C@H]([C@H](O)[C@@H](CO)O%18)O)[C@H]([C@H](O)[C@@H](CO)O%17)O)[C@H]([C@H](O)[C@@H](CO)O%16)O)[C@H]([C@H](O)[C@@H](CO)O%15)O)[C@H]([C@H](O)[C@@H](CO)O%14)O)[C@H]([C@H](O)[C@@H](CO)O%13)O)[C@H]([C@H](O)[C@@H](CO)O%12)O)[C@H]([C@H](O)[C@@H](CO)O%11)O)[C@H]([C@H](O)[C@@H](CO)O%10)O)[C@H]([C@H](O)[C@@H](CO)O9)O)[C@H]([C@H](O)[C@@H](CO)O8)O)[C@H]([C@H](O)[C@@H](CO)O7)O)[C@H]([C@H](O)[C@@H](CO)O6)O)[C@H]([C@H](O)[C@@H](CO)O5)O)[C@H]([C@H](O)[C@@H](CO)O4)O)[C@H]([C@H](O)[C@@H](CO)O3)O)[C@H]([C@H](O)[C@@H](CO)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 JYJIGFIDKWBXDU-MNNPPOADSA-N 0.000 claims description 2
- 229940029339 inulin Drugs 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 230000004048 modification Effects 0.000 abstract description 9
- 238000012986 modification Methods 0.000 abstract description 9
- 230000015556 catabolic process Effects 0.000 abstract description 5
- 238000006731 degradation reaction Methods 0.000 abstract description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 4
- 229920005654 Sephadex Polymers 0.000 abstract description 4
- 239000012507 Sephadex™ Substances 0.000 abstract description 4
- 229910052698 phosphorus Inorganic materials 0.000 abstract description 4
- 239000011574 phosphorus Substances 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 3
- 238000005187 foaming Methods 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 9
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 5
- 235000021317 phosphate Nutrition 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000004071 biological effect Effects 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000000694 effects 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
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000002715 modification method Methods 0.000 description 2
- 230000010355 oscillation Effects 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000019635 sulfation Effects 0.000 description 2
- 238000005670 sulfation reaction Methods 0.000 description 2
- ZFTFOHBYVDOAMH-XNOIKFDKSA-N (2r,3s,4s,5r)-5-[[(2r,3s,4s,5r)-5-[[(2r,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-2-(hydroxymethyl)oxolan-2-yl]oxymethyl]-2-(hydroxymethyl)oxolane-2,3,4-triol Chemical class O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@@H]1[C@@H](O)[C@H](O)[C@](CO)(OC[C@@H]2[C@H]([C@H](O)[C@@](O)(CO)O2)O)O1 ZFTFOHBYVDOAMH-XNOIKFDKSA-N 0.000 description 1
- 229920002670 Fructan Polymers 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- -1 hydrogen ions Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 235000019830 sodium polyphosphate Nutrition 0.000 description 1
- UGTZMIPZNRIWHX-UHFFFAOYSA-K sodium trimetaphosphate Chemical compound [Na+].[Na+].[Na+].[O-]P1(=O)OP([O-])(=O)OP([O-])(=O)O1 UGTZMIPZNRIWHX-UHFFFAOYSA-K 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
- C07H11/04—Phosphates; Phosphites; Polyphosphates
-
- 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
- C08B37/0051—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Fructofuranans, e.g. beta-2,6-D-fructofuranan, i.e. levan; Derivatives thereof
- C08B37/0054—Inulin, i.e. beta-2,1-D-fructofuranan; Derivatives thereof
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A phosphorylated chicory oligosaccharide and a preparation method thereof, and relates to a phosphorylated oligosaccharide and a preparation method thereof. Chicory polysaccharide is used as a raw material, chicory oligosaccharide is prepared by low-concentration trifluoroacetic acid degradation, sodium sulfate is added into a chicory oligosaccharide solution to prevent the polysaccharide solution from foaming by heating, sodium tripolyphosphate is used for carrying out phosphorylation modification on the chicory oligosaccharide, and the molar ratio of the chicory oligosaccharide to a phosphorylation reagent is 1:10, reacting for 3 hours at the temperature of 80 ℃ at the pH of 7.0, cooling, desalting by using a Sephadex G-15 gel column, and freeze-drying to obtain the phosphorylated chicory oligosaccharide with the phosphorus content of 5.4 percent.
Description
Technical Field
The invention relates to an oligosaccharide derivative and a preparation method thereof, in particular to a phosphorylated chicory oligosaccharide and a preparation method thereof, which are structural modification methods related to the phosphorylation of the chicory oligosaccharide.
Background
Chicory polysaccharide is a mixture of fructans, and has biological activities of resisting oxidation, diminishing inflammation, regulating immune system, resisting tumor, resisting virus, etc. Oligosaccharides tend to have higher water solubility and activity than polysaccharides because of their lower molecular weight than polysaccharides. The oligosaccharide molecule contains a large number of hydroxyl groups, and some functional groups are introduced into the oligosaccharide structure through chemical modification, so that the original biological activity of the oligosaccharide can be enhanced, and special functional characteristics can be endowed, thereby expanding the application range of the oligosaccharide. Methods for oligosaccharide modification include sulfation, carboxymethylation, selenization, and the like. The phosphorylation modification is a modification method similar to sulfation modification, and can obviously enhance the biological activity of substances, and the saccharide substances can enhance the physiological activities such as antioxidation, antiviral, antitumor and the like through the phosphorylation modification. At present, most of researches on the phosphorylation structure modification of saccharides are focused on the phosphorylation of polysaccharides, and the phosphorylation modification of chicory oligosaccharides has not been reported yet.
A common method of phosphorylation is phosphorus oxychloride (POCl) 3 ) Phosphoric acid, anhydrides thereof, phosphates, and the like. The phosphorus oxychloride method has the advantages of short reaction time and simple operation steps, but the use of phosphorus oxychloride can lead to degradation of target molecules, the concentration of hydrogen ions in the reaction process is increased, and alkaline reagents such as pyridine and triethylamine are needed to be added in the reaction process for neutralization so as to prevent degradation of polysaccharide; phosphoric acid and anhydride or a mixture of the phosphoric acid and the anhydride are the earliest used phosphorylating reagent, and the phosphoric acid group has high activity, but the phosphoric acid and the anhydride have the main defects of easy degradation of sugar samples, low product yield and unsatisfactory substitution degree in the reaction process; the phosphate method is a mild polysaccharide phosphorylation reaction, and the commonly used phosphate reagent mainly comprises sodium polyphosphate, disodium hydrogen phosphate, sodium trimetaphosphate, sodium dihydrogen phosphate and a mixture of the salts, and the phosphate method has the advantages of simple and convenient process, safety and high economic benefit, generates fewer byproducts and toxic and harmful substances, and is most popular in industrial production. According to the invention, sodium tripolyphosphate is selected as the phosphorylation reagent, and no organic solvent participates in the phosphorylation reaction process, so that the subsequent treatment is convenient.
Disclosure of Invention
The invention aims to provide a phosphorylated chicory oligosaccharide and a preparation method thereof.
The invention aims at realizing the following technical scheme:
a phosphorylated chicory oligosaccharide has a polymerization degree of 2-7, and a phosphate content of 5.4% of the phosphorylated chicory oligosaccharide after reaction with a phosphorylating agent.
The preparation raw material of the phosphorylated chicory oligosaccharide is knob chicory polysaccharide or inulin extracted from other chicory plants.
The preparation method of the phosphorylated chicory oligosaccharide comprises the step of preparing a phosphorylated chicory oligosaccharide by using sodium tripolyphosphate as a phosphorylating reagent.
A method for preparing phosphorylated chicory oligosaccharides, comprising the following steps: (1) Adding chicory polysaccharide into 0.01 mol/L trifluoroacetic acid to make polysaccharide concentration 1%, oscillating at constant temperature of 80deg.C for 15 min, concentrating the reaction solution under reduced pressure to obtain extract, and adding methanol for several times during rotary evaporation to remove trifluoroacetic acid. Purifying the degradation product by using a pretreated SephadexG-15 gel column, concentrating the collected liquid under reduced pressure, and freeze-drying to obtain chicory oligosaccharide. (2) Adding sodium sulfate into the aqueous solution prepared from chicory oligosaccharide, and then adding a phosphorylation reagent to make the molar ratio of chicory oligosaccharide to the phosphorylation reagent be 1:10; (3) Adjusting the pH value of the solution to 7, reacting for 3 hours at 80 ℃, taking out and cooling to room temperature; (4) desalting with SephadexG-15 gel column; (5) freeze-drying to obtain the phosphorylated chicory oligosaccharide.
Advantages and effects of the invention
Chicory polysaccharide and oligosaccharide (fructo-oligosaccharide) thereof have various biological activities, and the application value of the chicory polysaccharide and oligosaccharide (fructo-oligosaccharide) in the fields of foods and medicines can be further improved by carrying out phosphorylation modification on the chicory polysaccharide and oligosaccharide (fructo-oligosaccharide). According to the preparation method, chicory polysaccharide is used as a raw material, chicory oligosaccharide is prepared through trifluoroacetic acid degradation, sodium sulfate is added into a chicory oligosaccharide solution to prevent the polysaccharide solution from foaming by heating, sodium tripolyphosphate is used for carrying out phosphorylation modification on the chicory oligosaccharide, and the molar ratio of the chicory oligosaccharide to a phosphorylation reagent is 1:10, reacting for 3 hours at the temperature of 80 ℃ at the pH of 7.0, cooling, desalting by using a Sephadex G-15 gel column, and freeze-drying to obtain the phosphorylated chicory oligosaccharide with the phosphorus content of more than 5.4 percent. Characterization of the product by infrared spectroscopy and nuclear magnetic resonance analysis confirmed the reliability of the method. The antioxidant activity test result shows that the antioxidant activity of the phosphorylated modified red chicory oligosaccharide is obviously improved, and the application potential of the phosphorylated red chicory oligosaccharide in the fields of food, cosmetics and medicines is shown.
Drawings
FIG. 1 IR spectrum of chicory oligosaccharides;
FIG. 2 IR spectrum of phosphorylated chicory oligosaccharides;
FIG. 3 1H-NMR spectrum of phosphorylated chicory oligosaccharides;
FIG. 4 13C-NMR spectrum of phosphorylated chicory oligosaccharides;
FIG. 5 31P-NMR spectrum of phosphorylated chicory oligosaccharides.
Description of the embodiments
Example 1
5g of chicory polysaccharide is added into 0.01 mol/L trifluoroacetic acid to make the polysaccharide concentration 1%, the mixture is subjected to constant-temperature oscillation reaction at 80 ℃ for 15 min, and the reaction solution is immediately concentrated to an extract state under reduced pressure after the reaction is finished. Methanol was added a small number of times during the rotary evaporation to remove trifluoroacetic acid. Purifying the degradation product by using a pretreated SephadexG-15 gel column, concentrating under reduced pressure, and freeze-drying to obtain chicory oligosaccharide. 2G of chicory oligosaccharide is dissolved in 130mL of deionized water, 0.5G of sodium sulfate is added for uniform mixing, then 20 mL of 0.1G/mL of sodium tripolyphosphate aqueous solution (the molar ratio of chicory oligosaccharide to sodium tripolyphosphate is 1:10) is added, the pH is adjusted to 7.0, the solution is taken out for cooling after reacting for 3 hours at 80 ℃, and the solution is desalted by a pretreated Sephadex G-15 gel column and freeze-dried. The phosphorylated chicory oligosaccharides with a phosphorus content of 5.49% are obtained.
Example 2
20g of chicory polysaccharide is added into 0.01 mol/L trifluoroacetic acid to make the polysaccharide concentration be 1%, the mixture is subjected to constant-temperature oscillation reaction at 80 ℃ for 15 min, and the reaction solution is immediately concentrated to an extract state under reduced pressure after the reaction is finished. Methanol was added a small number of times during the rotary evaporation to remove trifluoroacetic acid. Purifying the degradation product by using a pretreated SephadexG-15 gel column, concentrating under reduced pressure, and freeze-drying to obtain chicory oligosaccharide. 10G chicory oligosaccharide is dissolved in 200 mL deionized water, 1.0G of sodium sulfate is added for uniform mixing, then 100 mL of 0.1G/mL sodium tripolyphosphate aqueous solution (the molar ratio of chicory oligosaccharide to sodium tripolyphosphate is 1:10) is added, the pH is adjusted to 7.0, the solution is taken out for cooling after reacting for 3 hours at 80 ℃, and the solution is desalted by a pretreated Sephadex G-15 gel column and freeze-dried. The phosphorylated chicory oligosaccharides with a phosphorus content of 5.37% are obtained.
Claims (4)
1. A phosphorylated chicory oligosaccharide, characterized in that the chicory oligosaccharide has a degree of polymerization in the range of 2-7 and has a phosphate content of 5.4% after reaction with a phosphorylating agent.
2. A phosphorylated chicory oligosaccharide according to claim 1, wherein the chicory oligosaccharide is prepared from chicory polysaccharide or inulin extracted from chicory.
3. A method for preparing phosphorylated chicory oligosaccharides according to claim 1, wherein said phosphorylating agent is sodium tripolyphosphate.
4. A method for preparing phosphorylated chicory oligosaccharides, which is characterized by comprising the following steps: the method comprises the following steps: (1) Adding chicory polysaccharide into 0.01 mol/L trifluoroacetic acid to make polysaccharide concentration 1%, oscillating at constant temperature of 80deg.C for 15 min, and concentrating the reaction solution under reduced pressure to obtain extract; methanol was added during the rotary evaporation to remove trifluoroacetic acid; purifying the degradation product by using a pretreated SephadexG-15 gel column, concentrating the collected liquid under reduced pressure, and freeze-drying to obtain chicory oligosaccharide; (2) Adding sodium sulfate into the chicory oligosaccharide preparation solution, and then adding a phosphorylation reagent to ensure that the molar ratio of the chicory oligosaccharide to the phosphorylation reagent is 1:10; (3) Adjusting the pH value of the solution to 7, reacting for 3 hours at 80 ℃, taking out and cooling to room temperature; (4) desalting with SephadexG-15 gel column; (5) freeze-drying to obtain the phosphorylated chicory oligosaccharide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310905309.4A CN117088998A (en) | 2023-07-24 | 2023-07-24 | Phosphorylated chicory oligosaccharide and preparation method thereof |
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