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Method for rapidly preparing six compounds in Stellera chamaejasme L.

A technology of chamaejasma chamaejasme and compounds, which is applied in the field of rapid preparation of 6 compounds in chamaejasma chamaejasme, achieving the effects of high separation efficiency, high product purity and cost reduction

Inactive Publication Date: 2015-05-13
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Anseretin C (compound 3) has obvious killing effect on chloroquine-resistant strains of Plasmodium falciparum, and its IC 50 The value can reach 0.56μg / ml (Nunome S, et al.PLANTA MED, 2004, 70 (1)); (+)-Langduning B (compound 4) can inhibit the proliferation of a variety of tumor cells in vitro, and is effective for human IC of lung adenocarcinoma cell A549 50 The value can reach 1.08μmol / L (Zhang C, et al.ACTA PHARMACOL SIN, 2013, 34 (2)); Isochalafin B (compound 5) shows strong antifungal and antimitotic activity, and has strong antifungal and antimitotic activity against blast fungus oryzae The MIC value is 6.25μg / mL (Yang G, et al.CHEM PHARM BULL, 2005, 53 (7)); the separation, preparation and pharmacological studies of compounds 2 and 6 have not been reported
In addition, as quality control index components, there must be a large supply of available chemical reference substances, but currently there are few reference substances for coumarin and dihydroflavonoids including these 6 compounds in the market

Method used

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  • Method for rapidly preparing six compounds in Stellera chamaejasme L.
  • Method for rapidly preparing six compounds in Stellera chamaejasme L.
  • Method for rapidly preparing six compounds in Stellera chamaejasme L.

Examples

Experimental program
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Effect test

Embodiment 1

[0036] In this example, using 95% (volume concentration, the same below) ethanol extract of Daphne chamaejasme as raw material, the first step of normal phase column chromatography uses 200-300 mesh silica gel, and the second step of reverse phase column chromatography uses 40 ~50 μm ODS, the third step of HPLC preparation adopts 5 μm C 18 The bonded phase preparation column uses methanol-water solution with a volume concentration of 75% as the elution system, and 6 pure compounds can be obtained after three-step separation. The specific process steps are as follows:

[0037] (1) Normal-phase silica gel column chromatography: extract the extract with 95% ethanol from Rhizoma chamaejasma, dissolve it in a mixture of chloroform and methanol, and add the same quality as the extract under constant stirring. 200-300 mesh column chromatography silica gel, mix the sample, and fully dry it at room temperature; then dry the sample, pass it through a 200-300 mesh silica gel column unde...

Embodiment 2

[0041] In this example, the 95% ethanol extract of Daphne chamaejasma was used as the raw material. The first step of normal phase column chromatography used 200-300 mesh silica gel, the second step of reverse-phase column chromatography used 40-50 μm ODS, and the third step HPLC preparation using 10 μm C 18 The bonded phase preparation column uses 50% acetonitrile-water solution as the elution system, and 6 kinds of pure compounds can be obtained after three-step separation. The specific process steps are as follows:

[0042] (1) Normal-phase silica gel column chromatography: extract the extract with 95% ethanol from Rhizoma chamaejasma, dissolve it in a mixture of chloroform and methanol, and add the same quality as the extract under constant stirring. 200-300 mesh column chromatography silica gel, mix the sample, and fully dry it at room temperature; then dry the sample, pass it through a 200-300 mesh silica gel column under normal pressure, and then use chloroform, chloro...

Embodiment 3

[0046] In this example, the 95% ethanol extract of Daphne chamaejasma was used as the raw material. The first step of normal phase column chromatography used 200-300 mesh silica gel, the second step of reverse-phase column chromatography used 40-50 μm ODS, and the third step HPLC preparation using 5 μm C 18 The bonded phase preparative column adopts 70% methanol-water solution as the eluting system, and 6 kinds of pure compounds can be obtained after three-step separation. The specific process steps are as follows:

[0047] (1) Normal-phase silica gel column chromatography: extract the extract with 95% ethanol from Rhizoma chamaejasma, dissolve it in a mixture of chloroform and methanol, and add the same quality as the extract under constant stirring. 200-300 mesh column chromatography silica gel, mix the sample, and fully dry it at room temperature; then dry the sample, pass it through a 200-300 mesh silica gel column under normal pressure, and then use chloroform, chlorofor...

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Abstract

The invention relates to a new method for rapidly preparing six highly pure compounds (comprising isodaphnoretin, sikokianin B, sikokianin C, (+)-chameajasmenin B, isochameajasmenin B and isochameajasmenin A) in Stellera chamaejasme L.. The method adopts a 95% ethanol extract product of a Stellera chamaejasme L. medicinal material as a raw material, adopts normal phase silica gel column chromatography and reverse phase ODS column chromatography to carry out preliminary separation and enrichment, and adopts preparative high performance liquid chromatography as a final separation means, and the compounds with the purity of 98% or more can be obtained through one-step high performance liquid phase preparation, corresponding fraction collection and direct reduced pressure concentration. The steps of the method are simple, and the above products have high purity and good color, so the method is very suitable for large scale production.

Description

technical field [0001] The invention relates to a new process for rapidly preparing six compounds in Daphne chamaejasme. It mainly includes positive and reverse column chromatography separation and enrichment and fast high performance liquid chromatography impurity removal preparation. Compound 1 (Isomanetin) is dicoumarin, Compound 2 (Anseretin B), 3 (Anseretin C), 4 ((+)-Navalenin B), 5 (Isobamaetin B), 6 (Isoflavone A) is a double dihydroflavone. Among them, compound 1 was prepared for the first time from a plant of the genus Eustoma, and compounds 2 and 6 are new isomers of this type of dihydroflavone. The chemical structures of these six compounds are as follows: [0002] Background technique [0003] Stellerachamaejasme (Stellerachamaejasme L.) is a plant of the genus Stellerachamaejasme in the family Stelleraceae. It is commonly known as Broken Heart Grass. It is distributed in China, Russia, Mongolia, North Korea and other countries. In my country, it is mainly...

Claims

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Application Information

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IPC IPC(8): C07D311/54C07D311/32C07D311/40
CPCC07D311/32C07D311/40C07D311/54
Inventor 肖红斌王志鑫高明哲
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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