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Compound salvianolic acid F methyl ester and preparation method thereof

A technology of salvianolic acid and methyl ester, applied in the field of phenolic acid compounds, can solve problems such as unsatisfactory curative effect

Active Publication Date: 2013-11-06
SUZHOU LEINA PHARMA RES DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, salvianolic acid B has been developed and marketed by Shanghai Institute of Materia Medica and Concord Pharmaceutical Institute, but the curative effect of these drugs is not satisfactory

Method used

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  • Compound salvianolic acid F methyl ester and preparation method thereof
  • Compound salvianolic acid F methyl ester and preparation method thereof
  • Compound salvianolic acid F methyl ester and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Take 28.7g of crude salvianolic acid (containing not less than 50% salvianolic acid B) and add 1.8L of methanol to dissolve, adjust the pH to 4.5, react under high temperature and high pressure at 120°C for 4 hours, cool down to room temperature, and adjust the pH to 3.0. Recovery of methanol yielded 25.2 g of crude salvianolic acid methyl ester, containing about 11.7% of salvianolic acid methyl ester. The crude total salvianolic acid methyl ester was dissolved in water. Using CG161S reversed-phase resin column (Φ20×50, column bed height 15cm) with 20%-40% methanol gradient elution until phenolic acid F methyl ester appears (collect eluate according to column volume→HPLC quantitative, TLC qualitative detection) to get Salvianolic acid F methyl ester 1.2 grams, content 94.7%.

Embodiment 2

[0036] Take 20 g of total salvianolic acid (salvianolic acid B content 95.0%, HPLC normalization method) and add 1.0 L of methanol to dissolve, adjust the pH to 4.5 with hydrochloric acid, react at high temperature and high pressure at 90 ° C for 5 hours, cool down to room temperature, and adjust the pH to 4.0 . Recover methanol to obtain 15.2 grams of salvianolic acid methyl ester crude product (containing salvianolic acid B; salvianolic acid A; salvianolic acid F and salvianolic acid methyl ester), containing about 21.0% of salvianolic acid methyl ester. The crude total salvianolic acid methyl ester was dissolved in water. Using CG161S reversed-phase resin column (Φ20×50, column bed height 15cm) with 20%-40% methanol gradient elution until phenolic acid F methyl ester appears (collect eluate according to column volume→HPLC quantitative, TLC qualitative detection) to get Salvianolic acid F methyl ester 3.2 grams, content 97.7%.

Embodiment 3

[0038] Take 20 g of total salvianolic acid (salvianolic acid A content 90.2%, HPLC normalization method) and add 1.0 L of methanol to dissolve, adjust the pH to 4, 5 with hydrochloric acid, react under high temperature and high pressure at 120°C for 3 hours, cool down to room temperature, and adjust the pH to 2.0. Recover methanol to obtain the crude salvianolic acid F methyl ester (containing salvianolic acid A; salvianolic acid F and salvianolic acid F methyl ester) 18.2 grams, containing about 31.0% of salvianolic acid F methyl ester. The crude total salvianolic acid methyl ester was dissolved in water. Using CG161S reversed-phase resin column (Φ20×50, column bed height 15cm) with 20%-40% methanol gradient elution until phenolic acid F methyl ester appears (collect eluate according to column volume→HPLC quantitative, TLC qualitative detection) to get Salvianolic acid F methyl ester 6.2 grams, content 97.8%.

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Abstract

The invention discloses a novel compound, namely salvianolic acid F methyl ester which is obtained by carrying out thermal decomposition on total salvianolic acid and has the activities of resisting reperfusion injury and resisting platelet aggregation. The compound has obvious antioxidation, has an obvious protective function on myocardial ischemia reperfusion injury of a rat and simultaneously has activity of resisting platelet aggregation. According to the invention, a lead compound is provided for developing a novel medicament which is used for treating ischemic cerebrocardiac diseases.

Description

technical field [0001] The invention relates to a brand-new phenolic acid compound salvianolic acid F methyl ester obtained from total phenolic acids of salvia miltiorrhiza and a preparation method thereof. Background technique [0002] Coronary atherosclerotic heart disease (CAHD) is a heart attack caused by an imbalance between coronary blood supply and myocardial demand due to coronary artery function or organic disease. Coronary heart disease is also called ischemic heart disease. The vast majority of CAHD is caused by coronary atherosclerosis, and a few can be caused by coronary arteries. Coronary heart disease is generally divided into painless myocardial ischemia, stable angina, unstable angina, myocardial infarction without Q wave and myocardial infarction with Q wave according to the severity of the disease. The latter three are collectively referred to as acute coronary syndrome due to their similar pathogenesis. disease. [0003] The standard of treatment for c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/732C07C67/08C07C67/03A61K31/216A61P9/10A61P7/02A61P39/06
Inventor 刘珂韩飞何克江陈栋许卉刘军锋
Owner SUZHOU LEINA PHARMA RES DEV