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Method for preparing polyhydroxy taxone and paclitaxel

A technology of polyhydroxytaxane and paclitaxel, which is applied in the field of natural product development or the manufacture of pharmaceutical raw materials, can solve the problems of waste of precious natural resources, etc., and achieve the effect of increasing resource utilization, reducing loss, and easy realization

Inactive Publication Date: 2009-03-25
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In these methods, polyacetyltaxanes are usually removed as "impurities", resulting in a great waste of valuable natural resources

Method used

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  • Method for preparing polyhydroxy taxone and paclitaxel
  • Method for preparing polyhydroxy taxone and paclitaxel
  • Method for preparing polyhydroxy taxone and paclitaxel

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1 Simultaneous preparation of paclitaxel and polyhydroxytaxane from Chinese yew branches and leaves extract (1) Resin column separation step: get 10 g of Chinese yew branches and leaves methanol extraction concentrated extract, and analyze by HPLC containing 0.2% paclitaxel ( 20 mg), containing about 5.7% (570 mg) of baccatin VI, dissolved in methanol, loaded onto the resin column of non-polar macroporous styrene adsorption resin XAD16, washed with 30% methanol-containing aqueous solution, and washed away the water-soluble Impurities or pigments; then eluted with 3 times the column volume of 50% methanol-containing aqueous solution, collected the eluate, evaporated the methanol to dryness, added an equal volume of ethyl acetate as the extraction solvent for liquid-liquid extraction, collected ethyl acetate The ester layer was evaporated to dryness to obtain 1.45g of macroporous resin column separation crude product, which contained 1.3% (18.8 mg) of paclitaxel an...

Embodiment 2

[0051] Example 2 Simultaneous preparation of paclitaxel and polyhydroxytaxane from Chinese yew cell culture extract

[0052] (1) Resin column separation step: take 5 g of the concentrated extract from Taxus chinensis cells extracted with methanol, and analyze by HPLC, containing 1% (50 mg) of paclitaxel and about 16% (800 mg) of Yunnanningin. Dissolve in methanol, load on the resin column of non-polar macroporous styrene adsorption resin XAD1180, wash with methanol containing 20% ​​aqueous solution to wash away water-soluble impurities or pigments; then use 3 times column volume with 80% methanol aqueous solution Elution, collect the eluent, evaporate the methanol to dryness, add an equal volume of chloroform for liquid-liquid extraction, collect the chloroform layer, evaporate to dryness, and obtain 2.65 g of the crude product separated by the macroporous resin column, which contains 1.8% paclitaxel by HPLC analysis (47mg), containing about 30% (795mg) of Yunnan Ning; the yie...

Embodiment 3

[0059] Example 3 Simultaneous preparation of paclitaxel and polyhydroxytaxane from southern yew branches and leaves extract

[0060] (1) Resin column separation step: Get 1Kg of the concentrated extract after the methanol extraction of the branches and leaves of Taxus chinensis, containing 0.18% (1.8g) of paclitaxel and about 5.5% (55g) of baccatin VI (BVI) through HPLC analysis. Dissolve it with methanol, load it on the resin column of non-polar macroporous styrene adsorption resin XAD16, wash it with an aqueous solution containing 40% methanol to wash away water-soluble impurities or pigments; then use 3 times the volume of the column with an aqueous solution containing 70% methanol Elution, collect the eluate, evaporate the methanol to dryness, add an equal volume of dichloromethane as the extraction solvent for liquid-liquid extraction, collect the dichloromethane layer, evaporate to dryness, and obtain 1.43g of macroporous resin column separation crude product, According ...

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Abstract

The invention relates to a method for preparing polyhydroxy taxane and paclitaxel, which pertains to the manufacturing method of natural medical chemical substances or drug raw materials, aims at the tight source of paclitaxel, and selectively converts the multi-acetyl taxane with high abundance in the alcohol extract of yew plant material or cell culture into corresponding polyhydroxy taxane while separating the paclitaxel. The invention comprises the steps of resin column separation, alumina chromatographic column separation, hydrolysis reaction, the solid phase extraction of polyhydroxy taxane, the elution of polyhydroxy taxane, the purification of paclitaxel and the purification of polyhydroxy taxane, thus obtaining the paclitaxel with the purity approaching to 99.5 percent and the polyhydroxy taxane with the purity being more than 98 percent. The invention selectively converts the multi-acetyl taxane with high abundance into corresponding polyhydroxy taxane, produces raw materials which can be used in the pharmaceuticals industry, significantly reduces the loss of taxane compounds in the raw materials and improves the availability of biological resources.

Description

technical field [0001] The invention belongs to the development of natural products or the production method of pharmaceutical raw materials, and specifically relates to the method of transforming and preparing polyhydroxytaxane and synchronously isolating paclitaxel by using yew plant material or alcoholic extract of cell culture as raw material. Background technique [0002] Paclitaxel (taxol) is a natural anti-tumor drug with significant curative effect. It also has a good application prospect in the treatment of AID-related Kaposi's Sarcoma (Kaposi's Sarcoma). (taxotere), and the third-generation paclitaxel 14-β-hydroxy deacetylbaccatin (ortataxel), which has entered the clinical phase II, have the same core structure, and the difference is only in the individual substituent groups on the core, collectively referred to as taxane compounds. Paclitaxel is a secondary metabolite of diterpenoids produced by Taxus chinensis. It has a complex structure, and it is unrealistic ...

Claims

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Application Information

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IPC IPC(8): C07D305/14C07C35/37C07C27/02A61P35/00
Inventor 赵春芳余龙江敖明章鲁明波李硕刘浩
Owner HUAZHONG UNIV OF SCI & TECH
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