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Homoisoflavonoid compounds and preparation method and use thereof

A technology of high isoflavones and compounds, applied in the field of medicine

Inactive Publication Date: 2011-07-20
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chinese patent application 200710121028.0 discloses a pharmaceutical composition containing Ophiopogon japonicus flavones, the preparation method of which is alcohol extraction, water precipitation, and petroleum ether extraction, which is completely different from the extraction method of total high isoflavone active parts disclosed in the present invention; Chinese patent application 200910012317.6 and Chinese patent application 200810055181.2 disclose the application of several high isoflavones for the treatment of tumors; Chinese patent CN 100453538C discloses that three kinds of high isoflavones in Shenmai injection are used for quality control and cardiovascular activity. In the range of compounds listed in the application; there is no research or report on the use of the high isoflavone compounds and total high isoflavone active parts of Ophiopogon japonicus listed in this application for cardiovascular diseases such as ischemic heart disease
There is no report about the extraction and preparation process of Ophiopogon japonicus as raw material high isoflavone compounds and total high isoflavone active parts of the present invention

Method used

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  • Homoisoflavonoid compounds and preparation method and use thereof
  • Homoisoflavonoid compounds and preparation method and use thereof
  • Homoisoflavonoid compounds and preparation method and use thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0020] A class of high isoflavone compounds provided by the present invention has the following general structural formula:

[0021]

[0022] where: R 1 is hydrogen or methyl or aldehyde; R 2 is hydroxyl or methoxy; R 3 is a methyl or aldehyde group; R 4 is hydroxyl or methoxy; R 5 is hydrogen or methoxy, or with R 6 together at the same time as -OCH 2 O- thus forming a five-membered ring; R 6 is hydroxyl or methoxy, or with R 5 together at the same time as -OCH 2 O- thus forming a five-membered ring.

[0023] Example 2

Embodiment 2

[0025]

[0026] Where: X-Y is -CH=C-; R 4 is hydroxyl; R 5 is hydrogen; R 6 is methoxy; more preferably, R 1 is methyl, R 2 is hydroxyl, R 3 is an aldehyde group, that is to say compound C; R 1 is methyl, R 2 is methoxy, R 3 is methyl, that is to say compound E; R 1 is an aldehyde group, R 2 is hydroxyl, R 3 is methyl, that is to say compound G.

[0027] In yet another preferred embodiment, the compound according to the general formula has the following structural formula:

[0028]

[0029] where: R 1 is an aldehyde group; R 2 is hydroxyl; R 3 is methyl; R 4 is methoxy; R 5 is hydrogen; R 6is methoxy; further preferably, X-Y is -CH=C-, that is to say compound A; X-Y is -CH 2 CH-, that is to say compound H.

[0030] In yet another preferred embodiment, the compound according to the general formula has the following structural formula:

[0031]

[0032] Where: X-Y is -CH=C-, R 1 is an aldehyde group, R 2 is hydroxyl, R 3 is methyl, R 4 is hydroxyl...

Embodiment 3

[0048] Take 10 kg of dried Ophiopogon japonicus fibrous roots, extract them three times with 95% ethanol, 60 L solution at room temperature, each time for one week, and combine the extracts. Recover the solvent until there is no alcohol smell to obtain 3.2 kg of extract. The obtained extract was dispersed with water, extracted with ethyl acetate and the solvent was recovered to obtain 198 g of ethyl acetate fraction. Treat the ethyl acetate part with macroporous resin, and gradually increase the ethanol concentration gradient elution starting from pure water elution. The fractions eluted with 50%-100% ethanol were collected to obtain a total of 39 g fractions with high isoflavone activity.

[0049] Example 4 Preparation of total high isoflavone active fractions with anti-myocardial ischemia activity

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Abstract

The invention provides homoisoflavonoid compounds, which are prepared by the following steps: grinding dwarf lilyturf tuber, adding extraction solvent into the ground dwarf lilyturf tuber according to a weight / volume ratio of the medicinal material to the solvent of 1:(6-10), performing normal-temperature extraction or reflux extraction, mixing extract solution, concentrating under reduced pressure, dissolving the extract in water, extracting in an organic solvent, recovering solvent to obtain coarse total homoisoflavonoid, loading onto a macroporous resin for eluting to obtain total homoisoflavonoid active part extract, and obtaining the homoisoflavonoid compounds by separation by normal silica gel, reversed silica gel and aluminum oxide column chromatography. A cell level H9C2 cardiac muscle cell line oxygen-glucose deprivation pharmacological model proves that the homoisoflavonoid compounds have anti-myocardial ischemia activity and can be used for preparing medicines for treating cardiovascular diseases such as ischemic heart diseases, coronary diseases, myocardial ischemia, myocardial infarction, stenocardia, arrhythmia and cardiac insufficiency. The general structural formula of the compound is shown below.

Description

technical field [0001] The invention belongs to the technical field of medicine, and specifically relates to a class of high-isoflavone compounds and total high-isoflavone active parts, a preparation method using Chinese medicine Radix Ophiopogon japonicus as a raw material, and an application in preparing anti-ischemic heart disease drugs. Background technique [0002] Ischemic Heart Diseases, also known as coronary heart disease, include angina pectoris, myocardial infarction, arrhythmia, etc. These diseases all share the common feature of myocardial cell ischemia and hypoxia. With the continuous acceleration of my country's population aging process, the incidence of coronary heart disease is increasing year by year, which seriously threatens the physical and mental health of the people. The main strategies for the clinical treatment of coronary heart disease are: 1. Drug therapy 2. Cardiac interventional therapy 3. Cardiac bypass surgery. Among them, the traditional main...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/22C07D407/06A61K31/352A61P9/10A61P9/00
Inventor 甘礼社周长新王学耀陆建锋王会平夏强
Owner ZHEJIANG UNIV
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