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Method for separation and purification of 10-deacetylbaccatin III from branches and leaves of taxus chinensis

A technology for deacetylation of yew branches and leaves, applied in the field of high-purity 10-DAB III, can solve the problems of yield loss, time-consuming, large solvent consumption, etc., achieve low cost, reduce manpower, avoid column chromatography and heavy The effect of the crystallization operation

Inactive Publication Date: 2015-09-09
JINGGANGSHAN UNIVERSITY
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  • Claims
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Problems solved by technology

[0006] Chinese Patent Publication No. CN1473821A discloses a method for extracting 10-DABIII, which uses conventional silica gel column chromatography to separate and extract the semi-finished product 10-DABIII. This method is time-consuming, and the solvent consumption is also large, which is easy to cause the loss of yield.
Chinese Patent Publication No. CN1398859A discloses a method for extracting 10-DABIII from residues after planting yew branches and leaves. The process is complicated and the solvent consumption is large

Method used

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  • Method for separation and purification of 10-deacetylbaccatin III from branches and leaves of taxus chinensis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] (1) Grind the yew branches and leaves into 100-mesh fine powder after drying, take 1 kg of fine powder and use the volume fraction of 80% ethanol aqueous solution to reflux extract for 5 hours, extract continuously for 3 times, and combine The filtrate was concentrated under reduced pressure to obtain 120 g of 10-DABIII extract.

[0024] (2) Dissolve the 10-DABIII extract in 300mL tetrahydrofuran and dry-load the sample, elute with ethyl acetate-petroleum ether (volume ratio ethyl acetate:petroleum ether=2:1), collect the elution containing 10-DABIII The liquid was removed, and the solvent was evaporated to obtain 1.85 g of 10-DABIII semi-finished product.

[0025] (3) Dissolve the above 10-DABIII semi-finished product in 20 mL of dichloromethane, add 0.20 g of imidazole, stir at room temperature for 30 minutes, let it stand, cool at 0°C, filter the resulting crystalline solid, and dry it in vacuum to obtain 10-DABIII and imidazole 1.08g of the crystalline complex.

...

Embodiment 2

[0028] (1) Grind the yew branches and leaves into 100-mesh fine powder after drying, take 10kg of powder and use the volume fraction of 80% ethanol aqueous solution to reflux extract for 5 hours, extract continuously for 3 times, and combine the filtrate , and concentrated under reduced pressure to obtain 1350 g of 10-DABIII extract.

[0029] (2) The 10-DABIII extract was dissolved in 3000mL THF, and then dry-loaded several times, eluted with ethyl acetate-cyclohexane (volume ratio ethyl acetate:cyclohexane = 2:1), and 10-DABIII was collected. -DABIII eluate, distill off the solvent to obtain 22.8g of 10-DABIII semi-finished product.

[0030] (3) Dissolve the above 10-DABIII semi-finished product in 200mL of dichloromethane, add 3.0g of imidazole, stir at room temperature for 30min, let stand, cool at 0°C, filter the resulting crystalline solid, and dry in vacuo to obtain 10-DABIII and imidazole The crystalline complex of 11.9g.

[0031] (4) The crystalline complex of 10-DAB...

Embodiment 3

[0033] (1) Grind the yew branches and leaves into 100-mesh fine powder after drying, take 5kg of powder and use the volume fraction of 80% ethanol aqueous solution to reflux extract for 5 hours, extract continuously for 3 times, and combine the filtrates , and concentrated under reduced pressure to obtain 680 g of 10-DABIII extract.

[0034] (2) Dissolve the 10-DABIII extract in 1200mL of dichloromethane, dry-load the sample several times, elute with ethyl acetate-petroleum ether (volume ratio ethyl acetate:petroleum ether=2:1), collect 10 -DABIII eluate, distill off the solvent to obtain 10.9g of 10-DABIII semi-finished product.

[0035] (3) After dissolving the above-mentioned 10-DABIII semi-finished product in 100mL of dichloromethane, add 2.0g of imidazole, stir at room temperature for 30min, let stand, cool at 0°C, filter the obtained crystalline solid, and dry in vacuum to obtain 10-DABIII and imidazole 5.8g of the crystalline complex.

[0036] (4) The crystalline comp...

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Abstract

The invention discloses a method for separation and purification of 10-deacetylbaccatin III from branches and leaves of taxus chinensis. The method includes the steps: 1) crushing and drying the branches and the leaves of taxus chinensis, adopting 80% ethyl alcohol for reflux extraction for 5 hours, continuously extracting for 3 times, and subjecting filtrate to vacuum concentration to obtain 10-DAB (deacetylbaccatin) III extracts; 2) dissolving the 10-DAB III extracts, performing dry method sampling to collect eluent containing 10-DAB III, and evaporating to remove solvents so as to obtain a semi-finished 10-DAB III product; 3) dissolving the semi-finished 10-DAB III product, adding imidazole compounds according to a mole ratio of (1:1.5)-4, stirring for 30min, standing, cooling at the temperature of 0 DEG C, filtering and drying to obtain a crystal complex of 10-DAB III and imidazole; 4) dissolving the crystal complex of 10-DAB III and imidazole in water, and extracting, drying and removing solvents to obtain a pure 10-DAB III product with 10-DAB III content being more than 99%.

Description

technical field [0001] The present invention relates to a method for separating and purifying 10-deacetylbaccatin III (10-DAB III) from branches and leaves of Taxus chinensis, especially to obtain high-purity 10-DAB by crystallization and purification of 10-DAB III crude product and imidazole compounds III Separation method. Background technique [0002] Docetaxel is considered to be one of the most effective anticancer drugs so far. It was confirmed by the FDA in 1996 and began to be used as clinical drugs for lung cancer, breast cancer, and colon cancer. Docetaxel, like paclitaxel (Taxol), has broad-spectrum anti-leukemia and anti-solid tumor activity, complex structure, multi-functional groups and multi-chiral centers, etc., and the total synthesis cost is high and difficult. When it was found that the taxane analogue 10-deacetyl baccatin (10-deacetyl baccatin III, referred to as 10-DAB III) intermediate was extracted from the needles of the European yew, the synthesis o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D305/14
CPCC07D305/14
Inventor 隋岩罗志刚陈丽
Owner JINGGANGSHAN UNIVERSITY
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