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Preparation method for urushiol compound

A compound, urushiol technology, applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., to achieve the effect of shortening time, avoiding thermal instability, and fewer steps

Inactive Publication Date: 2012-08-08
KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The inventor has long been engaged in the work of searching for anticancer substances from nature. He once found that a urushiol compound (GQ-3) in dry paint has anticancer effects. (Raw lacquer) has a high content and is a high-quality resource for drug development, but there is no simple and efficient process for obtaining the urushiol compound from raw lacquer

Method used

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  • Preparation method for urushiol compound
  • Preparation method for urushiol compound

Examples

Experimental program
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Effect test

Embodiment 1

[0026] Take 50.2 grams of raw lacquer, dissolve it with ethyl acetate, mix it with silica gel (100-200 mesh), evaporate the solvent, and set aside.

[0027] Get 300 grams of silica gel, use sherwood oil-ethyl acetate (30:1) wet packing column, column diameter 5cm, column length 35cm; The sample that mixes is added to the top of column, with petroleum ether-ethyl acetate (30:1) : 1) for elution, the flow rate is 1BV / h, the front 1000ml eluent is discarded, then every 100ml is collected in one portion, the fractions are detected by HPLC, 22-36 are combined, and the solvent is reclaimed under reduced pressure to obtain 4.1g of the sample.

[0028] Take by weighing 50g C-18 reverse-phase material, wet packing column, column diameter is 2.1cm, column length 21cm, takes by weighing the sample 1.25g that gains by silica gel column chromatography, dissolves with methanol, loads sample, with methanol-water ( 80:20) elution, the flow rate is 2ml / min, 20ml collects a fraction, collects 2...

Embodiment 2

[0031] Take 50.8 grams of raw lacquer, dissolve it with chloroform, mix it with silica gel (100-200 mesh), evaporate the solvent, and set aside.

[0032]Get 200 grams of silica gel, and use petroleum ether-ethyl acetate (20:1) wet packing column, column diameter 5cm, column length 22cm; : 1) for elution, the flow rate is 1.5BV / h, the front 900ml eluent is discarded, then every 100ml is collected in one portion, the fractions are detected by HPLC, 11-26 are combined, and the solvent is reclaimed under reduced pressure to obtain 4.2g of sample.

[0033] Weigh 80g of C-18 reverse-phase material, wet-pack the column with a column diameter of 2.1cm and a column length of about 33cm, weigh 1.31g of the sample obtained by silica gel column chromatography, dissolve it in methanol, load the sample, and use methanol-water (75:25) elution, flow rate is 1ml / min, 20ml collects a fraction, collects 260 fractions altogether, detects with HPLC, merges the 174th-258th fraction that contains ta...

Embodiment 3

[0036] Take 51.2 grams of raw lacquer, dissolve it with chloroform, mix it with silica gel (100-200 mesh), evaporate the solvent, and set aside.

[0037] Get about 400 grams of silica gel and wet-pack the column with petroleum ether-ethyl acetate (15:1), with a column diameter of 6 cm and a column length of 31 cm; add the mixed sample to the top of the column, and use petroleum ether-ethyl acetate ( 15:1) for elution, the flow rate is 2BV / h, the front 1500ml eluent is discarded, and then every 100ml is collected, and the fractions are detected by HPLC, 15-28 are combined, and the solvent is recovered under reduced pressure to obtain 4.25g of the sample.

[0038] Weigh about 100g of C-18 reversed-phase material and wet-pack the column with a diameter of 3cm and a column length of about 20cm. Weigh 1.28g of the sample obtained by silica gel column chromatography, dissolve it in methanol, load the sample, and use methanol-water (85:15) elution, flow rate is 1.5ml / min, about 20ml ...

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Abstract

The invention discloses a preparation method for an urushiol compound (Z)-3-(pentadec-8-en-l-yl)benzene-1,2-diol. The preparation method comprises the steps as follows: dissolving a raw lacquer from a lacquer tree by ethyl acetate, carrying out silica-gel column chromatography, eluting by a petroleum ether-ethyl acetate system, carrying out HPLC (High Performance Liquid Chromatography) detection, collecting the fractions containing the compound, combining the eluents and decompressing and recovering the solvent to obtain oily matters after concentration; carrying out RP-18 reversed-phase column chromatography, eluting by methanol-water, and collecting the fractions with the compound; and carrying out Sephadex LH-20 column chromatography on the oily matters after concentration, decolorizing and removing part of impurities. The preparation method is convenient to operate, and the pure urushiol compound with high purity and high yield can be obtained from the raw lacquer through the column chromatography in the three steps. Both the reverse phase silica gel and the gel used in the preparation method can be repeatedly used, the eluting solvent is cheaper and can be circularly used, and the preparation method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of chemistry and chemical engineering, and relates to extraction and separation technology of natural medicines, in particular to a urushiol compound (Z)-3-(pentadec-8-en-1-yl)benzene-1,2-diol in raw lacquer (abbreviated GQ-3) separation and purification process, the urushiol compound has anti-cancer effect, and is one of the medicinal components in raw lacquer and dry lacquer. Background technique [0002] Cancer is a serious threat to human health, known as "the number one killer of human beings", and the incidence rate is increasing year by year. It is estimated that by 2020, there may be 15 million new cancer patients worldwide every year. Throughout the period from 1981 to 2002, people searched for anticancer drug research, 60% came directly or indirectly from natural products, indicating that nature has become an important source of anticancer drugs, especially, in recent years, camptothecin, vincristine, three ...

Claims

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Application Information

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IPC IPC(8): C07C39/19C07C37/82
Inventor 程永现陈显强吕青
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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