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Method for extraction of paclitaxel from taxus chinensis

A technology of paclitaxel and yew, applied in the direction of organic chemistry, can solve the problems of high equipment requirements, high cost, complex paclitaxel extraction process, etc., and achieve the effect of small irreversible adsorption, low production cost and high selectivity

Inactive Publication Date: 2012-12-26
JILIN PAIGAO BIOLOGICAL PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The purpose of the present invention is to provide a method for extracting paclitaxel from Taxus chinensis, which is simple and low-cost; further, the present invention is simple and low-cost. Paclitaxel can be prepared efficiently and the high yield, high recovery rate and high purity of paclitaxel can be guaranteed at the same time, which can be well used as an anticancer drug to meet clinical use

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  • Method for extraction of paclitaxel from taxus chinensis
  • Method for extraction of paclitaxel from taxus chinensis
  • Method for extraction of paclitaxel from taxus chinensis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1 Optimization of paclitaxel extraction method

[0048] Paclitaxel is a tricyclic diterpene taxane, soluble in ethyl acetate, chloroform, ethanol, methanol and acetone, insoluble in water. The content of paclitaxel in yew plants is very low, and the content in the dry bark of yew is about 0.01-0.03%. At the same time, paclitaxel is easily degraded or isomerized into other taxane compounds under the influence of temperature, organic solvent, acid, alkali and other conditions. The production process adopts organic solvent extraction, and then removes polar impurities by extraction.

[0049] Currently, the organic solvents for leaching paclitaxel include methanol, ethanol, ethyl acetate-acetone, and the like. The physical and chemical properties of commonly used organic solvents are listed in Table 1. The ethyl acetate-acetone extraction effect is better than the price, and the extraction cost is relatively high. Ethanol has low toxicity and is commonly used ...

Embodiment 2

[0082] Example 2 Preparation of paclitaxel crude product

[0083] (1) Take 300 kg of the bark of Taxus chinensis (or the bark or branches and leaves of other Taxus species), crush it, add 80% methanol and soak it for 3 times (40℃~50℃, the quality of methanol solution is that of Taxus bark 5, 4, and 4 times the mass of the powder), each time for 3 hours, combine the methanol extracts, recover under reduced pressure until there is no alcohol smell (about 500 L), add chloroform for extraction 4 times (the volume of chloroform added for 4 times 300 L, 250 L, 250 L and 250 L respectively), the chloroform extraction layers were combined, and recovered under reduced pressure to a thick paste (7.5 kg).

[0084] (2) Extract the extract with chloroform, degrease with petroleum ether twice (add 100 L of petroleum ether each time, dissolve, filter at room temperature), evaporate the petroleum ether residue, and obtain a degreased extract (2.5 kg).

[0085] (3) Take 2.5 kg of degreased ...

Embodiment 3

[0089] Example 3 Preparation of pure paclitaxel

[0090] Take 21kg of 300-400 mesh thin-layer silica gel, 100g of cuprous oxide, 100g of ammonium chloride, and 100g of hydroxylamine hydrochloride, mix them, dissolve them into a paste with a mixture of 16L of methanol and 6L of purified water, stir for 2 hours, and reduce Dry it under pressure for 12 hours, dissolve it into a paste with 55L of dichloromethane, and pack it into a column.

[0091] Take by weighing the paclitaxel crude product (content > 40%) 200g prepared by Example 2, add 2L dichloromethane to dissolve, filter, and the filtrate is loaded on the industrially prepared silica gel chromatographic column that has been processed (silica gel for thin layer chromatography, 300~ 400 mesh, 8kg, 25×100cm), add dichloromethane-ethyl acetate gradient elution (dichloromethane, 10 L; dichloromethane-ethyl acetate (4:1), 12.5L; dichloromethane-acetic acid Ethyl ester (3:1), 12.5 L; dichloromethane-ethyl acetate (2:1), 25 L),...

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Abstract

Belonging to the technical field of medicine extraction, the invention discloses a method for extraction of paclitaxel from taxus chinensis. The extraction method provided in the invention consists of: using a methanol solution to conduct warm soaking extraction of taxus chinensis bark or branch and leaf powder, then carrying out chloroform extraction, performing silica gel column chromatography twice, implementing elution with a chloroform-methanol gradient solution and an n-hexane-acetic acid gradient elution respectively, and removing polar impurities so as to obtain a paclitaxel crude product; and further, carrying out third normal phase column chromatography, taking chemically treated silica gel as a stationary phase to effectively separate paclitaxel, recrystallizing the paclitaxel obtained from the column chromatography, thus obtaining a paclitaxel pure product with purity of over 98% pure product, with a process transfer rate being more than 80%. All the reagents used in the extraction method belong to the industrial grade, and the method provided in the invention has the advantages of wide applicability, strong innovation, simple process, low separation cost, high product yield, thus having innovative production value for industrial separation and production of paclitaxel.

Description

technical field [0001] The invention belongs to the technical field of medicine extraction, and in particular relates to a method for extracting paclitaxel from yew. Background technique [0002] Paclitaxel (trade name Taxol) is a natural active ingredient with high anti-tumor activity, and it is a diterpenoid extracted from Taxus genus. Paclitaxel has a complex chemical structure (Formula I). ​​The molecule is a diterpene composed of 3 main rings. The molecule has 11 chiral centers and multiple substituent groups. [0003] [0004] (I) [0005] At present, the main source of paclitaxel API production in my country is natural yew bark or branches and leaves. However, due to the scarcity of yew plant resources and the immature industrialization scale of artificially planted yew plants, paclitaxel from natural sources is still not enough for clinical application. The demand of Chinese pharmaceutical companies for paclitaxel is highly dependent on imports. Some imported y...

Claims

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Application Information

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IPC IPC(8): C07D305/14
Inventor 汤贤敏梁群欢朱永平张国焕路天威
Owner JILIN PAIGAO BIOLOGICAL PHARMA
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