Method for separating galanthamine

A technology of galantamine and extract, which is applied in the field of separation of galantamine, can solve the problems of not meeting high-quality requirements, difficulty in removing similar alkaloid impurities, etc., achieves low implementation cost, rapid separation, and is conducive to industrial scale-up Effect

Active Publication Date: 2011-05-11
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is difficult to remove impurities similar to alkaloids by using traditional separation technology, and it does not meet the current high-quality requirements of galantamine in various countries in the world. Therefore, the production process of separating and purifying galantamine with high efficiency, high purity and low cost has far-reaching implications. significance

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The total alkaloid extract of Lycoris radiata (containing 10% galantamine and 20% other alkaloids, determined by HPLC) 5.0g and 0.6g L-(-)-dibenzoyltartaric acid (purchased from Jinan Biyoute Chemical Co., Ltd.), use 15.0ml of 75% ethanol as solvent, heat to 80°C, and heat for 30min to obtain a clear solution. Then it was cooled to 25°C and crystals precipitated [Crystal I: IR (KBr, cm -1 ) 3418, 3068, 3056, 2960, 1731, 1635, 1602, 1586, 1335, 1318, 1266, 1179, 1026, 1003, 937, 890, 710, 684, 650, 617. 1 H NMR(DMSO-d 6 )δ8.046(d, 1H), 7.742(d, 1H), 7.619(d, 1H), 6.85(AB, 2H, J=9.6Hz), 6.15(d, 1H, J=7.9Hz), 5.95( dd, 1H, J = 7.9 Hz, J = 3.2 Hz), 5.922 (d, 1H), 4.85 (d, 1H, J = 16.0 Hz), 4.60 (s, 1H), 4.47 (bs, 1H), 4.35 ( d, 1H, J = 16.0 Hz), 4.10 (bs, 1H), 3.70-3.90 (s+m, 4H), 3.50 (d, 1H, J = 12.8 Hz), 2.85 (bs, 3H), 2.40-2.00 (m, 3H), 1.90 (d, 1H, J=16.0 Hz)]. Filtration, while recovering solvents, identification reagents, and by-product mixed alkaloid filtrate. Cry...

Embodiment 2

[0028] Mix 6.4g of total alkaloids (including galantamine 13% and other alkaloids 18%) with 3.0g L-(-)-dibenzoyl tartaric acid, use 19.2ml 85% ethanol as solvent, and heat to 100°C , Heat 1h to get a clear solution. Then it was cooled to 10°C, and crystals precipitated [Crystal I: IR (KBr, cm -1 ) 3418, 3068, 3056, 2960, 1731, 1635, 1602, 1586, 1335, 1318, 1266, 1179, 1026, 1003, 937, 890, 710, 684, 650, 617. 1 HNMR(DMSO-d 6 )δ8.046(d, 1H), 7.742(d, 1H), 7.619(d, 1H), 6.85(AB, 2H, J=9.6Hz), 6.15(d, 1H, J=7.9Hz), 5.95( dd, 1H, J = 7.9 Hz, J = 3.2 Hz), 5.922 (d, 1H), 4.85 (d, 1H, J = 16.0 Hz), 4.60 (s, 1H), 4.47 (bs, 1H), 4.35 ( d, 1H, J = 16.0 Hz), 4.10 (bs, 1H), 3.70-3.90 (s+m, 4H), 3.50 (d, 1H, J = 12.8 Hz), 2.85 (bs, 3H), 2.40-2.00 (m, 3H), 1.90 (d, 1H, J=16.0 Hz)]. Filtration, while recovering solvents, identification reagents, and by-product mixed alkaloid filtrate. Crystal I 0.78g was recrystallized by adding 19.2ml 75% ethanol, then filtered, and the ethanol solvent wa...

Embodiment 3

[0030] Mix 7.3g of total alkaloids (including galantamine 8% and other alkaloids 19%) with 0.8g L-(-)-dibenzoyltartaric acid, use 17ml 95% ethanol as solvent, and heat to 70℃ , Heat for 50min to get a clear solution. Then it was cooled to -10°C to precipitate crystals [Crystal I: IR (KBr, cm -1 ) 3418, 3068, 3056, 2960, 1731, 1635, 1602, 1586, 1335, 1318, 1266, 1179, 1026, 1003, 937, 890, 710, 684, 650, 617. 1 HNMR(DMSO-d 6 )δ8.046(d, 1H), 7.742(d, 1H), 7.619(d, 1H), 6.85(AB, 2H, J=9.6Hz), 6.15(d, 1H, J=7.9Hz), 5.95( dd, 1H, J = 7.9 Hz, J = 3.2 Hz), 5.922 (d, 1H), 4.85 (d, 1H, J = 16.0 Hz), 4.60 (s, 1H), 4.47 (bs, 1H), 4.35 ( d, 1H, J = 16.0 Hz), 4.10 (bs, 1H), 3.70-3.90 (s+m, 4H), 3.50 (d, 1H, J = 12.8 Hz), 2.85 (bs, 3H), 2.40-2.00 (m, 3H), 1.90 (d, 1H, J=16.0 Hz)]. Filtration, while recovering solvents, identification reagents, and by-product mixed alkaloid filtrate. Crystal I 0.48g was recrystallized by adding 21.9ml of 55% ethanol, then filtered, and the ethanol solvent ...

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Abstract

The invention discloses a method for separating galanthamine. The method comprises the following steps: detecting the content of galanthamine in a total alkaloid extract in lycoris radiate; mixing the total alkaloid extract of lycoris radiate with dibenzoyl-L-tartaric acid; taking 75-95 percent of alcohol as the solvent; carrying out sufficient reaction at the temperature of 70 DEG C to 100 DEG C to obtain a clear solution; cooling the clear solution to minus 10 DEG C to 25 DEG C; standing until a crystal is separated out; filtering to obtain a filter cake and then performing recrystallization to the filter cake with a recrystallization solvent A to obtain a crude product of the crystal; adding in aqueous alkaline solution; adjusting the pH value to 7 to 9; decomposing; adding in CHCl3 for extraction; taking an organic coating for vaporizing and eliminating the solvent to obtain crude galanthamine; dissolving the crude galanthamine with acetone; adding in HBr aqueous solution; filtering to obtain galanthamine hydrobromide; and finally performing recrystallization to the galanthamine hydrobromide with a recrystallization solvent B to obtain the pure galanthamine. The separation efficiency is high, the primary crystallization is only required, the yield of galanthamine reaches 80 to 90 percent, and the purity of galanthamine reaches 90 to 99 percent; and the method has the advantages of simple operation, good repeatability, low implementation cost and less pollution and is favorable for industrial scale-up.

Description

(1) Technical field [0001] The present invention relates to a method for separating galantamine, especially a method for separating galantamine from many other alkaloids from plant extracts containing alkaloids of Amaryllidaceae. (2) Background technology [0002] Galantamine, also known as Galanthamine, is a tetracyclic alkaloid with tertiary amine. It is a reversible cholinesterase inhibitor and can be widely used in senile dementia (AD), treatment of myasthenia gravis, intestinal paralysis and sequelae of polio. Galantamine is often used clinically in the form of hydrobromide, and it went on the market in 2003. With the increase of the global elderly population and the increasing burden of diseases caused by Alzheimer's disease, galantamine, as a central cholinesterase inhibitor with mild effects and mild side effects, has received renewed attention. [0003] Galantamine was originally extracted from the dried bulbs of Xia Xuepilian, and later it was also found in Tianshan Xue...

Claims

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Application Information

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IPC IPC(8): C07D491/107
Inventor 金志敏王聪
Owner ZHEJIANG UNIV OF TECH
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