CN106496419A - 一种抗胃癌活性蔗渣木聚糖没食子酸酯‑g‑MAA/BA的合成方法 - Google Patents
一种抗胃癌活性蔗渣木聚糖没食子酸酯‑g‑MAA/BA的合成方法 Download PDFInfo
- Publication number
- CN106496419A CN106496419A CN201610946592.5A CN201610946592A CN106496419A CN 106496419 A CN106496419 A CN 106496419A CN 201610946592 A CN201610946592 A CN 201610946592A CN 106496419 A CN106496419 A CN 106496419A
- Authority
- CN
- China
- Prior art keywords
- bagasse xylan
- added
- pure
- epicatechol gallate
- xylan
- 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
- 229920001221 xylan Polymers 0.000 title claims abstract description 73
- 239000010905 bagasse Substances 0.000 title claims abstract description 71
- 241000609240 Ambelania acida Species 0.000 title claims abstract description 70
- 150000004823 xylans Chemical class 0.000 title claims abstract description 69
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 title claims abstract description 53
- PFTAWBLQPZVEMU-UKRRQHHQSA-N (-)-epicatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-UKRRQHHQSA-N 0.000 title claims abstract description 32
- 230000000694 effects Effects 0.000 title claims abstract description 12
- 206010017758 gastric cancer Diseases 0.000 title claims abstract description 10
- 208000005718 Stomach Neoplasms Diseases 0.000 title claims abstract description 9
- 201000011549 stomach cancer Diseases 0.000 title claims abstract description 9
- 238000010189 synthetic method Methods 0.000 title abstract description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims abstract description 26
- 235000004515 gallic acid Nutrition 0.000 claims abstract description 23
- 229940074391 gallic acid Drugs 0.000 claims abstract description 19
- 239000000463 material Substances 0.000 claims abstract description 17
- 239000000178 monomer Substances 0.000 claims abstract description 15
- 239000003999 initiator Substances 0.000 claims abstract description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000243 solution Substances 0.000 claims description 26
- 238000001914 filtration Methods 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 238000004458 analytical method Methods 0.000 claims description 13
- 239000012153 distilled water Substances 0.000 claims description 13
- 239000000047 product Substances 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 11
- 239000012467 final product Substances 0.000 claims description 11
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000011521 glass Substances 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000012043 crude product Substances 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 4
- 238000001291 vacuum drying Methods 0.000 claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 240000003152 Rhus chinensis Species 0.000 claims description 3
- 235000014220 Rhus chinensis Nutrition 0.000 claims description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 235000019441 ethanol Nutrition 0.000 claims description 3
- 125000005909 ethyl alcohol group Chemical group 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 239000012047 saturated solution Substances 0.000 claims description 3
- 239000013049 sediment Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 150000004968 peroxymonosulfuric acids Chemical class 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 abstract description 12
- 230000032050 esterification Effects 0.000 abstract description 10
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 abstract description 8
- 125000005395 methacrylic acid group Chemical class 0.000 abstract description 6
- 229910001870 ammonium persulfate Inorganic materials 0.000 abstract description 4
- 238000007334 copolymerization reaction Methods 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 230000002708 enhancing effect Effects 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 230000000977 initiatory effect Effects 0.000 abstract 1
- 230000001093 anti-cancer Effects 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000012086 standard solution Substances 0.000 description 6
- 230000001629 suppression Effects 0.000 description 4
- -1 xylan ester Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 238000002479 acid--base titration Methods 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 238000000205 computational method Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- 201000007270 liver cancer Diseases 0.000 description 2
- 208000014018 liver neoplasm Diseases 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 206010023774 Large cell lung cancer Diseases 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 241001593750 Turcica Species 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 230000010100 anticoagulation Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 230000009514 concussion Effects 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 208000010749 gastric carcinoma Diseases 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 201000009546 lung large cell carcinoma Diseases 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 239000010815 organic waste Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 201000000498 stomach carcinoma Diseases 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000000969 xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F251/00—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
-
- 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
- C08B37/0057—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Xylans, i.e. xylosaccharide, e.g. arabinoxylan, arabinofuronan, pentosans; (beta-1,3)(beta-1,4)-D-Xylans, e.g. rhodymenans; Hemicellulose; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Materials Engineering (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
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CN201610946592.5A CN106496419B (zh) | 2016-10-26 | 2016-10-26 | 一种抗胃癌活性蔗渣木聚糖没食子酸酯-g-MAA/BA的合成方法 |
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CN201610946592.5A CN106496419B (zh) | 2016-10-26 | 2016-10-26 | 一种抗胃癌活性蔗渣木聚糖没食子酸酯-g-MAA/BA的合成方法 |
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CN106496419A true CN106496419A (zh) | 2017-03-15 |
CN106496419B CN106496419B (zh) | 2018-11-06 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN107400186A (zh) * | 2017-09-15 | 2017-11-28 | 桂林理工大学 | 一种活性蔗渣木聚糖丁香酸酯‑g‑AM/ MMA/BA的合成方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101962424A (zh) * | 2010-09-16 | 2011-02-02 | 桂林理工大学 | 丙烯酰胺/甲基丙烯酸甲酯接枝蔗渣木聚糖共聚物的制备方法 |
CN102321215A (zh) * | 2011-06-01 | 2012-01-18 | 桂林理工大学 | 一种接枝蔗渣木聚糖共聚物的制备方法 |
CN104530263A (zh) * | 2014-12-17 | 2015-04-22 | 桂林理工大学 | 一种没食子酸蔗渣木聚糖酯的制备方法 |
-
2016
- 2016-10-26 CN CN201610946592.5A patent/CN106496419B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101962424A (zh) * | 2010-09-16 | 2011-02-02 | 桂林理工大学 | 丙烯酰胺/甲基丙烯酸甲酯接枝蔗渣木聚糖共聚物的制备方法 |
CN102321215A (zh) * | 2011-06-01 | 2012-01-18 | 桂林理工大学 | 一种接枝蔗渣木聚糖共聚物的制备方法 |
CN104530263A (zh) * | 2014-12-17 | 2015-04-22 | 桂林理工大学 | 一种没食子酸蔗渣木聚糖酯的制备方法 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107400186A (zh) * | 2017-09-15 | 2017-11-28 | 桂林理工大学 | 一种活性蔗渣木聚糖丁香酸酯‑g‑AM/ MMA/BA的合成方法 |
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Application publication date: 20170315 Assignee: GUANGXI AGLYCONE PLANT PRODUCTS Co.,Ltd. Assignor: GUILIN University OF TECHNOLOGY Contract record no.: X2023980044210 Denomination of invention: Synthesis method of bagasse xylan gallate g-MAA/BA with anti-gastric cancer activity Granted publication date: 20181106 License type: Common License Record date: 20231025 |
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Application publication date: 20170315 Assignee: Guangxi Guiren Energy Saving Technology Co.,Ltd. Assignor: GUILIN University OF TECHNOLOGY Contract record no.: X2023980045083 Denomination of invention: Synthesis method of bagasse xylan gallate g-MAA/BA with anti-gastric cancer activity Granted publication date: 20181106 License type: Common License Record date: 20231103 Application publication date: 20170315 Assignee: GUANGXI CHAOXING SOLAR ENERGY TECHNOLOGY Co.,Ltd. Assignor: GUILIN University OF TECHNOLOGY Contract record no.: X2023980045079 Denomination of invention: Synthesis method of bagasse xylan gallate g-MAA/BA with anti-gastric cancer activity Granted publication date: 20181106 License type: Common License Record date: 20231030 |