CN1283633A - 灵芝α－(1→3)－D－葡聚糖羧甲基化衍生物及其用途和制备方法 - Google Patents
灵芝α－(1→3)－D－葡聚糖羧甲基化衍生物及其用途和制备方法 Download PDFInfo
- Publication number
- CN1283633A CN1283633A CN 99116590 CN99116590A CN1283633A CN 1283633 A CN1283633 A CN 1283633A CN 99116590 CN99116590 CN 99116590 CN 99116590 A CN99116590 A CN 99116590A CN 1283633 A CN1283633 A CN 1283633A
- Authority
- CN
- China
- Prior art keywords
- dextran
- aqueous solution
- ganoderic
- alpha
- carboxyl methylation
- 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
- 238000000034 method Methods 0.000 title claims abstract description 7
- 229920001503 Glucan Polymers 0.000 title abstract description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 27
- 239000007864 aqueous solution Substances 0.000 claims abstract description 19
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- 229920002307 Dextran Polymers 0.000 claims description 26
- 241001597008 Nomeidae Species 0.000 claims description 18
- 230000011987 methylation Effects 0.000 claims description 18
- 238000007069 methylation reaction Methods 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 230000036737 immune function Effects 0.000 claims description 3
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 229940041181 antineoplastic drug Drugs 0.000 claims description 2
- 230000000259 anti-tumor effect Effects 0.000 abstract description 11
- 150000004676 glycans Chemical class 0.000 abstract description 9
- 229920001282 polysaccharide Polymers 0.000 abstract description 9
- 239000005017 polysaccharide Substances 0.000 abstract description 9
- 238000002360 preparation method Methods 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 abstract description 2
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- 240000008397 Ganoderma lucidum Species 0.000 abstract 2
- 235000001637 Ganoderma lucidum Nutrition 0.000 abstract 2
- 241000699670 Mus sp. Species 0.000 abstract 1
- 231100000331 toxic Toxicity 0.000 abstract 1
- 230000002588 toxic effect Effects 0.000 abstract 1
- 241000222336 Ganoderma Species 0.000 description 7
- 206010028980 Neoplasm Diseases 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 208000030507 AIDS Diseases 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- 230000010100 anticoagulation Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 229940041984 dextran 1 Drugs 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229960002949 fluorouracil Drugs 0.000 description 1
- 238000006197 hydroboration reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000003808 methanol extraction Methods 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明公开了具有抗肿瘤活性的灵芝α－(1→3)－D一葡聚糖羧甲基化衍生物的制备方法。该方法用碱水溶液首次从灵芝子实体中提取出水不溶性线型α－(1→3)－D－葡聚糖,该多糖不具有抗肿瘤活性。将α－(1→3)－D－葡聚糖溶解在NaOH水溶液中,用氯乙酸钠水溶液在80℃对其羧甲基化6-8小时制备了该多糖的羧甲基衍生物。这种衍生物是水溶性的,对植入小鼠体内的爱氏腹水瘤(EAC)的生长具有明显的抑制作用,并且无毒副作用。
Description
本发明涉及一种具有抗肿瘤活性的α-(1→3)-D-葡聚糖羧甲基化衍生物及其用途和制备方法，这种衍生物具有明显的抗肿瘤活性，它属于高分子化学领域，也属于分子生物学领域。
80年代以来的研究表明，灵芝水不溶性多糖是灵芝多糖的主要成分。Sone等人(Agric.Biol.Chem.49，2641，1985)的研究认为灵芝水不溶性多糖是灵芝子实体β-(1→3)-D-葡聚糖，但不具有抗肿瘤活性且不能被β-(1→3)-D-葡聚糖水解酶水解。通过化学修饰改变多糖生物活性的报道主要有Smith降解(药学学报21，944，1986)，高碘酸氧化后硼氢化还原(Carbohydr.Res.115，273，1983)，羧甲基化(Eur.J.Cancer 15，2110，1978)和硫酸酯化(Antimicrob.Agents Chemother.85，6132，1985；Biochem.Pharmcol.37，2887，1988；J.Immunopharmcol.12，225，1990)等，由此提高多糖在抗肿瘤、抗爱滋病毒及抗凝血等方面生物活性。
本发明的目的是提供一种一种具有抗肿瘤活性的α-(1→3)-D-葡聚糖羧甲基化衍生物及其用途和制备方法，该方法将利用灵芝子实体中含量最多而又无生物活性的水不溶性α-(1→3)-D-葡聚糖(含量占3％)，通过羧甲基化后变为水溶性衍生物，从而使其具有明显抗肿瘤活性和免疫功能，并可用作保健品，而且可望开发成天然药物，是一种科技含量高的产物。
为实现上述目的，本发明所采用的技术方案如下：
一种灵芝α-(1→3)-D-葡聚糖羧甲基化衍生物，它是将α-(1→3)-D-葡聚糖溶于NaOH水溶液，恒温80℃，在持续搅拌下缓慢滴加氯乙酸钠水溶液，反应6-8小时后，取出反应物溶液用盐酸中和至中性，并在甲醇中沉淀出产物，分别用甲醇水溶液和无水甲醇洗涤，得到的即为灵芝α-(1→3)D-葡聚糖羧甲基化衍生物。
所制得的羧甲基化衍生物对植入小鼠(昆明种小白鼠)体内的爱氏腹水肿瘤(EAC)都具有明显的抑制作用。动物实验结果见附表1。因此，本发明的灵芝α-(1→3)-D-葡聚糖羧甲基化衍生物用于制备抗肿瘤药物或提高人体免疫机能的保健品。
制备本发明的灵芝α-(1→3)-D-葡聚糖羧甲基化衍生物方法是：首先从灵芝子实体中分离出水不溶性线型α-(1→3)-D-葡聚糖。其分子量为19.5×104，在1NNaOH中[α]D=170(degcm2g-1)。将其溶解在NaOH水溶液中，用氯乙酸钠水溶液于80℃，羧甲基化6-8小时，用甲醇沉淀出产物。接着用甲醇水溶液洗涤，最后用无水甲醇洗涤，真空干燥后得羧甲基化衍生物。
本发明建立了以灵芝子实体水不溶性线型α-(1→3)-D-葡聚糖为原料制备出水溶性羧甲基化衍生物的方法。动物体内试验证明，α-(1→3)-D-葡聚糖羧甲基化衍生物具有显著的抗肿瘤EAC活性，且无毒副作用，可用作保健品，作为抗肿瘤天然药物也具有应用前景。本发明与已有技术相比有实质性不同，而且有明显的技术进步。
本发明首次用灵芝α-(1→3)-D-葡聚糖为原料，通过羧甲基衍生化使水不溶性且无生物活性的多糖变为水溶性，且抗肿瘤活性明显的多糖衍生物。此法工艺简单，操作方便，效果显著。
以下结合具体的实施例对本发明的技术方案作进一步的说明：
实施例1
灵芝子实体经粉碎、脱脂、再用磷酸盐缓冲液于100℃下提取出水溶性多糖后，用1M NaOH水溶液提取出水不溶性α-(1→3)-D-葡聚糖。将它的NaOH溶液在流水中透析7天，再对蒸馏水透析3天。此时NaOH被透析掉，多糖沉淀出来。然后将浑浊液进行离心，收集固体并进行真空干燥。由此得到白色粉末状灵芝α-(1→3)-D-葡聚糖。
灵芝α-(1→3)-D-葡聚糖1克，溶于50mL NaOH水溶液。恒温80℃，在持续搅拌下缓慢滴加氯乙酸钠水溶液40mL，并于30分钟内滴加完。在反应6小时后取出反应物溶液，用盐酸中和至中性，在甲醇中沉淀出产物。将所得产物用甲醇水溶液洗涤6次，无水甲醇洗涤6次，真空干燥7天，由此得到白色粉状的羧甲基化衍生物。产率为80～85％。
附表1．灵芝α-(1→3)-D-葡聚糖及其衍生物抗EAC肿瘤活性
| 样 品 | 剂量(mg/kg/day) | 抑制率(％) |
| 灵芝α-(1→3)-D-葡聚糖 | 12.0×7 | 0 |
| 灵芝α-(1→3)-D-葡聚糖羧甲基化衍生物 | 34.7×7 | 35.6 |
| 比较组：5-氟尿嘧啶 | 20.0×7 | 56.7 |
Claims (3)
1．一种灵芝α-(1→3)-D-葡聚糖羧甲基化衍生物，其特征在于它是将α-(1→3)-D-葡聚糖溶于NaOH水溶液，恒温80℃，在持续搅拌下缓慢滴加氯乙酸钠水溶液，反应6-8小时后，取出反应物溶液用盐酸中和至中性，并在甲醇中沉淀出产物，分别用甲醇水溶液和无水甲醇洗涤，得到的即为灵芝α-(1→3)-D-葡聚糖羧甲基化衍生物。
2．权利要求1所述的灵芝α-(1→3)-D-葡聚糖的羧甲基化衍生物用于制备抗肿瘤药物或提高人体免疫机能的保健品。
3．一种制备权利要求1所述的灵芝α-(1→3)-D-葡聚糖羧甲基化衍生物的方法，其特征在于：它是将α-(1→3)-D-葡聚糖溶于NaOH水溶液，恒温80℃，在持续搅拌下缓慢滴加氯乙酸钠水溶液，反应6-8小时后，取出反应物溶液用盐酸中和至中性，并在甲醇中沉淀出产物，分别用甲醇水溶液和无水甲醇洗涤，即得到灵芝α-(1→3)-D-葡聚糖羧甲基化衍生物。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB99116590XA CN1133654C (zh) | 1999-08-05 | 1999-08-05 | 灵芝α-(1→3)-D-葡聚糖羧甲基化衍生物及其用途和制备方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB99116590XA CN1133654C (zh) | 1999-08-05 | 1999-08-05 | 灵芝α-(1→3)-D-葡聚糖羧甲基化衍生物及其用途和制备方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1283633A true CN1283633A (zh) | 2001-02-14 |
| CN1133654C CN1133654C (zh) | 2004-01-07 |
Family
ID=5279387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB99116590XA Expired - Fee Related CN1133654C (zh) | 1999-08-05 | 1999-08-05 | 灵芝α-(1→3)-D-葡聚糖羧甲基化衍生物及其用途和制备方法 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1133654C (zh) |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100439401C (zh) * | 2005-11-30 | 2008-12-03 | 华南理工大学 | 羧甲基裂褶多糖的制备方法及其在化妆品或抗肿瘤药物中的应用 |
| CN103804512A (zh) * | 2014-01-16 | 2014-05-21 | 昆山京昆油田化学科技开发公司 | 一种半乳糖基葡聚糖衍生物的制备方法 |
| CN103816204A (zh) * | 2013-11-19 | 2014-05-28 | 新乡医学院 | 中药菟丝子提取物化学修饰的制备方法和临床应用 |
| WO2014099724A1 (en) * | 2012-12-20 | 2014-06-26 | E. I. Du Pont De Nemours And Company | Preparation of poly alpha-1,3-glucan ethers |
| WO2015095358A1 (en) | 2013-12-18 | 2015-06-25 | E. I. Du Pont De Nemours And Company | Cationic poly alpha-1,3-glucan ethers |
| WO2015138283A1 (en) | 2014-03-11 | 2015-09-17 | E. I. Du Pont De Nemours And Company | Oxidized poly alpha-1,3-glucan as detergent builder |
| US9139718B2 (en) | 2012-12-20 | 2015-09-22 | E I Du Pont De Nemours And Company | Preparation of poly alpha-1,3-glucan ethers |
| CN105001347A (zh) * | 2015-06-24 | 2015-10-28 | 河南中烟工业有限责任公司 | 羧甲基化灵芝多糖、合成纯化方法及其作为烟草保润剂的应用 |
| US9278988B2 (en) | 2012-12-27 | 2016-03-08 | E I Du Pont De Nemours And Company | Preparation of poly alpha-1,3-glucan esters and films made therefrom |
| CN106255707A (zh) * | 2013-12-16 | 2016-12-21 | 纳幕尔杜邦公司 | 聚α‑1，3‑葡聚糖醚类作为粘度调节剂的用途 |
| US9714403B2 (en) | 2014-06-19 | 2017-07-25 | E I Du Pont De Nemours And Company | Compositions containing one or more poly alpha-1,3-glucan ether compounds |
| US9771548B2 (en) | 2014-06-19 | 2017-09-26 | E I Du Pont De Nemours And Company | Compositions containing one or more poly alpha-1,3-glucan ether compounds |
| US9926541B2 (en) | 2014-02-14 | 2018-03-27 | E I Du Pont De Nemours And Company | Glucosyltransferase enzymes for production of glucan polymers |
| US9968910B2 (en) | 2014-12-22 | 2018-05-15 | E I Du Pont De Nemours And Company | Polysaccharide compositions for absorbing aqueous liquid |
| US10059778B2 (en) | 2014-01-06 | 2018-08-28 | E I Du Pont De Nemours And Company | Production of poly alpha-1,3-glucan films |
| US10106626B2 (en) | 2014-01-17 | 2018-10-23 | Ei Du Pont De Nemours And Company | Production of poly alpha-1,3-glucan formate films |
| CN117487037A (zh) * | 2023-12-29 | 2024-02-02 | 山东国力生物科技有限公司 | 一种制备多位取代羧甲基葡聚糖的方法及其产品 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5038687B1 (zh) * | 1970-08-20 | 1975-12-11 | ||
| JPS5893702A (ja) * | 1981-12-01 | 1983-06-03 | Sankyo Co Ltd | β−１，３−グルカンおよびその製法 |
| JPS61152702A (ja) * | 1984-12-26 | 1986-07-11 | Daicel Chem Ind Ltd | カルボキシメチルデキストランの製造法 |
| CA1269495A (en) * | 1985-11-05 | 1990-05-22 | Masato Naito | Expanded particles of modified polyethylene and foamed articles obtained therefrom |
| CA1328074C (en) * | 1988-09-01 | 1994-03-29 | Shigenori Tanaka | Horseshoe crab amebocyte lysate factor g inhibitor |
| JPH03207804A (ja) * | 1990-01-10 | 1991-09-11 | Nippon Steel Corp | 高炉原料装入物落下位置検出方法及び落下位置制御方法 |
| JPH0784481B2 (ja) * | 1991-02-21 | 1995-09-13 | 株式会社デイ・デイ・エス研究所 | カルボキシメチルマンノグルカン及びその誘導体 |
| ES2149867T3 (es) * | 1993-02-26 | 2000-11-16 | Drug Delivery System Inst Ltd | Derivados de polisacaridos y soportes para farmacos. |
| JP3207804B2 (ja) * | 1998-04-14 | 2001-09-10 | 東京瓦斯株式会社 | ディジタル圧力表示計 |
-
1999
- 1999-08-05 CN CNB99116590XA patent/CN1133654C/zh not_active Expired - Fee Related
Cited By (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100439401C (zh) * | 2005-11-30 | 2008-12-03 | 华南理工大学 | 羧甲基裂褶多糖的制备方法及其在化妆品或抗肿瘤药物中的应用 |
| US9139718B2 (en) | 2012-12-20 | 2015-09-22 | E I Du Pont De Nemours And Company | Preparation of poly alpha-1,3-glucan ethers |
| CN104854135B (zh) * | 2012-12-20 | 2018-06-22 | 纳幕尔杜邦公司 | 聚α-1，3-葡聚糖醚的制备 |
| WO2014099724A1 (en) * | 2012-12-20 | 2014-06-26 | E. I. Du Pont De Nemours And Company | Preparation of poly alpha-1,3-glucan ethers |
| AU2013363174B2 (en) * | 2012-12-20 | 2017-08-03 | Nutrition & Biosciences USA 4, Inc. | Preparation of poly alpha-1,3-glucan ethers |
| CN104854135A (zh) * | 2012-12-20 | 2015-08-19 | 纳幕尔杜邦公司 | 聚α-1,3-葡聚糖醚的制备 |
| US10000580B2 (en) | 2012-12-27 | 2018-06-19 | E I Du Pont De Nemours And Company | Preparation of poly alpha-1,3-glucan esters and films therefrom |
| US9278988B2 (en) | 2012-12-27 | 2016-03-08 | E I Du Pont De Nemours And Company | Preparation of poly alpha-1,3-glucan esters and films made therefrom |
| CN103816204A (zh) * | 2013-11-19 | 2014-05-28 | 新乡医学院 | 中药菟丝子提取物化学修饰的制备方法和临床应用 |
| US10865254B2 (en) | 2013-12-16 | 2020-12-15 | Dupont Industrial Biosciences Usa, Llc | Use of poly alpha-1,3-glucan ethers as viscosity modifiers |
| EP4163305A1 (en) | 2013-12-16 | 2023-04-12 | Nutrition & Biosciences USA 4, Inc. | Use of poly alpha-1,3-glucan ethers as viscosity modifiers |
| CN106255707A (zh) * | 2013-12-16 | 2016-12-21 | 纳幕尔杜邦公司 | 聚α‑1，3‑葡聚糖醚类作为粘度调节剂的用途 |
| CN106255707B (zh) * | 2013-12-16 | 2019-06-18 | 纳幕尔杜邦公司 | 聚α-1，3-葡聚糖醚类作为粘度调节剂的用途 |
| US10005850B2 (en) | 2013-12-16 | 2018-06-26 | E I Du Pont De Nemours And Company | Use of poly alpha-1,3-glucan ethers as viscosity modifiers |
| WO2015095358A1 (en) | 2013-12-18 | 2015-06-25 | E. I. Du Pont De Nemours And Company | Cationic poly alpha-1,3-glucan ethers |
| US10323102B2 (en) | 2013-12-18 | 2019-06-18 | E I Du Pont De Nemours And Company | Cationic poly alpha-1,3-glucan ethers |
| US9957334B2 (en) | 2013-12-18 | 2018-05-01 | E I Du Pont De Nemours And Company | Cationic poly alpha-1,3-glucan ethers |
| US10800860B2 (en) | 2013-12-18 | 2020-10-13 | Dupont Industrial Biosciences Usa, Llc | Cationic poly alpha-1,3-glucan ethers |
| EP3789407A1 (en) | 2013-12-18 | 2021-03-10 | Nutrition & Biosciences USA 4, Inc. | Cationic poly alpha-1,3-glucan ethers |
| US10059778B2 (en) | 2014-01-06 | 2018-08-28 | E I Du Pont De Nemours And Company | Production of poly alpha-1,3-glucan films |
| CN103804512A (zh) * | 2014-01-16 | 2014-05-21 | 昆山京昆油田化学科技开发公司 | 一种半乳糖基葡聚糖衍生物的制备方法 |
| US10106626B2 (en) | 2014-01-17 | 2018-10-23 | Ei Du Pont De Nemours And Company | Production of poly alpha-1,3-glucan formate films |
| US9926541B2 (en) | 2014-02-14 | 2018-03-27 | E I Du Pont De Nemours And Company | Glucosyltransferase enzymes for production of glucan polymers |
| US10072100B2 (en) | 2014-03-11 | 2018-09-11 | E I Du Pont De Nemours And Company | Oxidized poly alpha-1,3-glucan |
| WO2015138283A1 (en) | 2014-03-11 | 2015-09-17 | E. I. Du Pont De Nemours And Company | Oxidized poly alpha-1,3-glucan as detergent builder |
| US9695253B2 (en) | 2014-03-11 | 2017-07-04 | E I Du Pont De Nemours And Company | Oxidized poly alpha-1,3-glucan |
| US9771548B2 (en) | 2014-06-19 | 2017-09-26 | E I Du Pont De Nemours And Company | Compositions containing one or more poly alpha-1,3-glucan ether compounds |
| US10221378B2 (en) | 2014-06-19 | 2019-03-05 | E I Du Pont De Nemours And Company | Compositions containing one or more poly alpha-1,3-glucan ether compounds |
| US10190079B2 (en) | 2014-06-19 | 2019-01-29 | E I Du Pont De Nemours And Company | Compositions containing one or more poly alpha-1,3-glucan ether compounds |
| US9714403B2 (en) | 2014-06-19 | 2017-07-25 | E I Du Pont De Nemours And Company | Compositions containing one or more poly alpha-1,3-glucan ether compounds |
| US11015150B2 (en) | 2014-06-19 | 2021-05-25 | Nutrition & Biosciences USA 4, Inc. | Compositions containing one or more poly alpha-1,3-glucan ether compounds |
| US10639611B2 (en) | 2014-12-22 | 2020-05-05 | Dupont Industrial Biosciences Usa, Llc | Polysaccharide compositions for absorbing aqueous liquid |
| US9968910B2 (en) | 2014-12-22 | 2018-05-15 | E I Du Pont De Nemours And Company | Polysaccharide compositions for absorbing aqueous liquid |
| CN105001347A (zh) * | 2015-06-24 | 2015-10-28 | 河南中烟工业有限责任公司 | 羧甲基化灵芝多糖、合成纯化方法及其作为烟草保润剂的应用 |
| CN117487037A (zh) * | 2023-12-29 | 2024-02-02 | 山东国力生物科技有限公司 | 一种制备多位取代羧甲基葡聚糖的方法及其产品 |
| CN117487037B (zh) * | 2023-12-29 | 2024-03-15 | 山东国力生物科技有限公司 | 一种制备多位取代羧甲基葡聚糖的方法及其产品 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1133654C (zh) | 2004-01-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1283633A (zh) | 灵芝α－(1→3)－D－葡聚糖羧甲基化衍生物及其用途和制备方法 | |
| Kagimura et al. | Biological activities of derivatized d-glucans: A review | |
| Freimund et al. | A new non-degrading isolation process for 1, 3-β-D-glucan of high purity from baker's yeast Saccharomyces cerevisiae | |
| Wu et al. | Structural elucidation and immunomodulatory activity of a β-D-glucan prepared by freeze-thawing from Hericium erinaceus | |
| Yan et al. | Structure elucidation and immunomodulatory activity of a β-glucan derived from the fruiting bodies of Amillariella mellea | |
| Zhang et al. | Evaluation of mushroom dietary fiber (nonstarch polysaccharides) from sclerotia of Pleurotus tuber-regium (Fries) Singer as a potential antitumor agent | |
| Shashidhar et al. | Functional polysaccharides from medicinal mushroom Cordyceps sinensis as a potent food supplement: extraction, characterization and therapeutic potentials–a systematic review | |
| Yu et al. | Structural characteristics and anti-tumor/-oxidant activity in vitro of an acidic polysaccharide from Gynostemma pentaphyllum | |
| JP6174219B2 (ja) | 新規多糖体 | |
| EP0654047A1 (en) | Glucans with immunostimulant activity | |
| Freitas et al. | Fungi as sources of polysaccharides for pharmaceutical and biomedical applications | |
| Yiasmin et al. | Purification, isolation, and structure characterization of water soluble and insoluble polysaccharides from Maitake fruiting body | |
| CN103408672B (zh) | 一种低分子量金耳多糖及其制备方法 | |
| CN104892793A (zh) | 桑黄菌丝体多糖、制备方法及其在抗肿瘤的应用 | |
| Miranda-Nantes et al. | Hypoglycemic and hypocholesterolemic effects of botryosphaeran from Botryosphaeria rhodina MAMB-05 in diabetes-induced and hyperlipidemia conditions in rats | |
| Liang et al. | Extraction of chitin from flammulina velutipes waste: A low-concentration acid pretreatment and aspergillus Niger fermentation approach | |
| CN118845817A (zh) | 一种土壤杆菌生产的L-β-半乳葡聚糖及其制备方法和应用 | |
| Hui et al. | Fine structure and hypoglycemic effect of a galactoglucan from the bulbs of Lanzhou lily | |
| JP4183326B2 (ja) | ハナビラタケ抽出物 | |
| CN102191298A (zh) | 一种高效降解果胶多糖的方法 | |
| CN101891837A (zh) | 一种羧甲基化双歧杆菌胞外多糖及其制备方法和应用 | |
| Bi et al. | Structures of (1→ 6)-β-D-glucans from Bulgaria inquinans (Fries) and their immunological activities | |
| JP4451100B2 (ja) | タモギタケ子実体組成物を有効成分として含有する免疫賦活剤、及び抗癌剤 | |
| CN1133653C (zh) | 灵芝α-(1→3)-D-葡聚糖硫酸酯衍生物及其用途和制备方法 | |
| AU2017101852A4 (en) | Chitooligosaccharide with a specific structure and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |