CN101602767B - 一种加兰他敏的制备方法 - Google Patents
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- ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 title claims abstract description 58
- 229960003980 galantamine Drugs 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- HPOIPOPJGBKXIR-UHFFFAOYSA-N 3,6-dimethoxy-10-methyl-galantham-1-ene Natural products O1C(C(=CC=2)OC)=C3C=2CN(C)CCC23C1CC(OC)C=C2 HPOIPOPJGBKXIR-UHFFFAOYSA-N 0.000 title abstract description 5
- LPCKPBWOSNVCEL-UHFFFAOYSA-N Chlidanthine Natural products O1C(C(=CC=2)O)=C3C=2CN(C)CCC23C1CC(OC)C=C2 LPCKPBWOSNVCEL-UHFFFAOYSA-N 0.000 title abstract description 5
- BGLNUNCBNALFOZ-WMLDXEAASA-N galanthamine Natural products COc1ccc2CCCC[C@@]34C=CCC[C@@H]3Oc1c24 BGLNUNCBNALFOZ-WMLDXEAASA-N 0.000 title abstract description 5
- ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 title abstract description 5
- IYVSXSLYJLAZAT-NOLJZWGESA-N lycoramine Natural products CN1CC[C@@]23CC[C@H](O)C[C@@H]2Oc4cccc(C1)c34 IYVSXSLYJLAZAT-NOLJZWGESA-N 0.000 title abstract description 5
- 238000000605 extraction Methods 0.000 claims abstract description 38
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000000284 extract Substances 0.000 claims abstract description 11
- 239000000843 powder Substances 0.000 claims abstract description 11
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 10
- SIHHLZPXQLFPMC-UHFFFAOYSA-N chloroform;methanol;hydrate Chemical compound O.OC.ClC(Cl)Cl SIHHLZPXQLFPMC-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000001035 drying Methods 0.000 claims abstract description 9
- 238000001953 recrystallisation Methods 0.000 claims abstract description 9
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 17
- 238000000194 supercritical-fluid extraction Methods 0.000 claims description 16
- 239000007864 aqueous solution Substances 0.000 claims description 11
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 8
- 239000012141 concentrate Substances 0.000 claims description 7
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
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- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 241001502078 Galanthus woronowii Species 0.000 description 1
- 241000319062 Lycoris radiata Species 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 208000000474 Poliomyelitis Diseases 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
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- Y02P20/00—Technologies relating to chemical industry
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Abstract
本发明涉及一种操作简便、污染小的加兰他敏的制备方法，工艺步骤为取原料细粉，加入碱水溶液中浸泡过夜，烘干，置于CO2超临界萃取装置中超临界萃取；萃取物加入2％的盐酸水溶液溶解，滤过，滤液加入三氯甲烷萃取，取下层液，调节pH至13，加入三氯甲烷萃取，取三氯甲烷层，通过氧化铝色谱柱分离，取三氯甲烷-甲醇-水下层溶液为洗脱剂洗脱，收集洗脱液，浓缩，加入丙酮-乙醇重结晶，洗涤、干燥即得。采用本发明制备加兰他敏，产品纯度高，易于实现产业化放大。
Description
技术领域
本发明涉及一种加兰他敏的制备方法，尤其是一种从植物中提取加兰他敏的方法。
背景技术
加兰他敏(Galanthamine)是一个叔胺生物碱，最早是在1952年由Proskurnina和Yakovleva从石蒜科植物沃氏雪花莲Galanthus woronowii Losink中分离得到，广泛分布于石蒜科植物中。其结构式如下：
有研究表明加兰他敏对小儿麻痹后遗症、重症肌无力和外伤性截瘫等病症有效，且毒性较小。20世纪90年代以后，加兰他敏的氢溴酸盐又被用于治疗阿尔茨海默病，并因其无心、肝毒副作用而有望成为治疗该病的首选药物。在我国加兰他敏的来源植物中，石蒜Lycoris radiata Herb.、忽地笑L.aruea Herb.、夏水仙L.squamigeric Herb.的鳞茎均为为石蒜属中提取加兰他敏的良好原料。
现有技术中，加兰他敏的提取分离法主要是有机溶剂法等，步骤多、排污量大，并且这些提取工艺得到的加兰他敏的含量很低，不利大生产操作。
发明内容
本发明所要解决的技术问题是提供一种利于大生产操作、产品纯度高的加兰他敏的制备方法。
为解决上述技术问题，本发明采用下列技术方案：
取原料细粉，加入碱水溶液中浸泡过夜，烘干，置于CO2超临界萃取装置中超临界萃取，CO2流量为1-5ml/min/g生药，选用90％乙醇水溶液为夹带剂，流量为0.1-0.8ml/min/g生药，萃取温度20-80℃，压力10-50MPa，萃取时间0.5-4h；萃取物加入2％的盐酸水溶液溶解，滤过，滤液加入三氯甲烷萃取，取下层液，调节pH至13，加入三氯甲烷萃取，取三氯甲烷层，通过氧化铝色谱柱分离，取三氯甲烷-甲醇-水下层溶液为洗脱剂洗脱，收集洗脱液，浓缩，加入丙酮-乙醇重结晶，洗涤、干燥即得。
提取加兰他敏的原料选自石蒜科植物石蒜、忽地笑、夏水仙。
浸泡原料的碱水溶液的pH＝12，优选三乙胺水溶液。
CO2超临界萃取的条件优选为：CO2流量为2ml/min/g生药，选用90％乙醇水溶液为夹带剂，流量为0.4ml/min/g生药，萃取温度60℃，压力30MPa，萃取时间2h。
氧化铝色谱柱分离步骤中，洗脱液优选三氯甲烷-甲醇-水(5∶3∶1)的下层溶液。
重结晶步骤中丙酮-乙醇的配比优选为1∶1。
采用上述技术方案制备加兰他敏，操作简便、污染少，利于大生产操作。
下面将结合具体实施方式对本发明做进一步阐述，但本发明要求保护的范围并不局限于下列实施方式。
具体实施方式
实施例1
取石蒜鳞茎细粉10Kg，加入pH＝12的三乙胺水溶液中浸泡过夜，烘干，置于CO2超临界萃取装置中超临界萃取，CO2流量为2ml/min/g生药，选用90％乙醇水溶液为夹带剂，流量为0.4ml/min/g生药，萃取温度60℃，压力30MPa，萃取时间2h；萃取物加入2％的盐酸水溶液溶解，滤过，滤液加入CHCl3萃取，取下层液，调节pH至13，加入CHCl3萃取，取CHCl3层，通过氧化铝色谱柱分离，取三氯甲烷-甲醇-水(5∶3∶1)下层溶液为洗脱剂洗脱，收集洗脱液，浓缩，加入丙酮-乙醇(1∶1)重结晶，洗涤、干燥即得加兰他敏213mg，经HPLC检测，其纯度为94.5％。
实施例2
取石蒜鳞茎细粉10Kg，加入pH＝10的氨水溶液中浸泡过夜，烘干，置于CO2超临界萃取装置中超临界萃取，CO2流量为1ml/min/g生药，选用90％乙醇水溶液为夹带剂，流量为0.1ml/min/g生药，萃取温度20℃，压力10MPa，萃取时间0.5h；萃取物加入2％的盐酸水溶液溶解，滤过，滤液加入CHCl3萃取，取下层液，调节pH至13，加入CHCl3萃取，取CHCl3层，通过氧化铝色谱柱分离，取三氯甲烷-甲醇-水(4∶5∶1)下层溶液为洗脱剂洗脱，收集洗脱液，浓缩，加入丙酮-乙醇(3∶1)重结晶，洗涤、干燥即得加兰他敏175mg，经HPLC检测，其纯度为92.3％。
实施例3
取石蒜鳞茎细粉10Kg，加入pH＝13的三乙胺水溶液中浸泡过夜，烘干，置于CO2超临界萃取装置中超临界萃取，CO2流量为5ml/min/g生药，选用90％乙醇水溶液为夹带剂，流量为0.8ml/min/g生药，萃取温度80℃，压力50MPa，萃取时间4h；萃取物加入2％的盐酸水溶液溶解，滤过，滤液加入CHCl3萃取，取下层液，调节pH至13，加入CHCl3萃取，取CHCl3层，通过氧化铝色谱柱分离，取三氯甲烷-甲醇-水(2∶1∶1)下层溶液为洗脱剂洗脱，收集洗脱液，浓缩，加入丙酮-乙醇(1∶6)重结晶，洗涤、干燥即得加兰他敏235mg，经HPLC检测，其纯度为93.4％。
实施例4
取忽地笑鳞茎细粉10Kg，加入pH＝12的三乙胺水溶液中浸泡过夜，烘干，置于CO2超临界萃取装置中超临界萃取，CO2流量为2ml/min/g生药，选用90％乙醇水溶液为夹带剂，流量为0.4ml/min/g生药，萃取温度60℃，压力30MPa，萃取时间2h；萃取物加入2％的盐酸水溶液溶解，滤过，滤液加入CHCl3萃取，取下层液，调节pH至13，加入CHCl3萃取，取CHCl3层，通过氧化铝色谱柱分离，取三氯甲烷-甲醇-水(5∶3∶1)下层溶液为洗脱剂洗脱，收集洗脱液，浓缩，加入丙酮-乙醇(1∶1)重结晶，洗涤、干燥即得加兰他敏208mg，经HPLC检测，其纯度为96.4％。
实施例5
取夏水仙鳞茎细粉10Kg，加入pH＝12的三乙胺水溶液中浸泡过夜，烘干，置于CO2超临界萃取装置中超临界萃取，CO2流量为2ml/min/g生药，选用90％乙醇水溶液为夹带剂，流量为0.4ml/min/g生药，萃取温度60℃，压力30MPa，萃取时间2h；萃取物加入2％的盐酸水溶液溶解，滤过，滤液加入CHCl3萃取，取下层液，调节pH至13，加入CHCl3萃取，取CHCl3层，通过氧化铝色谱柱分离，取三氯甲烷-甲醇-水(5∶3∶1)下层溶液为洗脱剂洗脱，收集洗脱液，浓缩，加入丙酮-乙醇(1∶1)重结晶，洗涤、干燥即得加兰他敏241mg，经HPLC检测，其纯度为93.5％。
Claims (6)
1.一种加兰他敏的制备方法，其特征在于所述的方法包括下列步骤: 取石蒜科石蒜、忽地笑、夏水仙中任一种植物的鳞茎细粉，加入碱水溶液中浸泡过夜，烘干，置于CO2超临界萃取装置中超临界萃取，CO2流量为1-5ml/min/g生药，选用90%乙醇水溶液为夹带剂，流量为0.1-0.8ml/min/g生药，萃取温度20-80℃，压力10-50MPa，萃取时间0.5-4h；萃取物加入2%的盐酸水溶液溶解，滤过，滤液加入三氯甲烷萃取，取下层液，调节pH至13，加入三氯甲烷萃取，取三氯甲烷层，通过氧化铝色谱柱分离，取三氯甲烷-甲醇-水下层溶液为洗脱剂洗脱，收集洗脱液，浓缩，加入丙酮-乙醇重结晶，洗涤、干燥即得。
2.根据权利要求1所述的一种加兰他敏的制备方法，其特征在于所述的碱水溶液的pH=12。
3.根据权利要求2所述的一种加兰他敏的制备方法，其特征在于所述的碱水溶液为三乙胺水溶液。
4.根据权利要求1所述的一种加兰他敏的制备方法，其特征在于所述的超临界萃取的条件为：CO2流量为2ml/min/g生药，选用90%乙醇水溶液为夹带剂，流量为0.4ml/min/g生药，萃取温度60℃，压力30MPa，萃取时间2h。
5.根据权利要求1所述的一种加兰他敏的制备方法，其特征在于所述三氯甲烷-甲醇-水的配比为5:3:1。
6.根据权利要求1所述的一种加兰他敏的制备方法，其特征在于所述丙酮-乙醇的配比为1:1。
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| CN102477035B (zh) * | 2010-11-23 | 2014-12-10 | 成都合盛生物技术有限公司 | 一种从伏康树籽中提取纯化它勃宁的清洁化工艺 |
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| US5877172A (en) * | 1995-03-17 | 1999-03-02 | Lts Lohmann Therapie-Systeme Gmbh | Process for isolating galanthamine |
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