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Preparation of isocardiospermin-5-p-hydroxybenzoate and its application in the preparation of drugs for treating rheumatoid arthritis

A technology for rheumatoid and medicinal materials, applied to the preparation of Isocardiospermin-5-p-hydroxybenzoate and its application in the preparation of rheumatoid arthritis drugs, can solve the problems of high treatment cost, heavy social burden and the like

Active Publication Date: 2020-08-18
BINZHOU MEDICAL COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The treatment of RA patients requires long-term medication to control the course of the disease and improve symptoms, and the cost of treatment is high and the social burden is heavy
At present, the drugs used clinically to treat RA mainly include non-steroidal anti-inflammatory drugs (NSAIDs), glucocorticoids, disease-modifying antirheumatic drugs, biological agents and herbal preparations, etc., although they have certain However, most of them have strong toxic and side effects, and there is still a big gap between this and the ideal anti-rheumatoid drug that needs to be taken for a long time

Method used

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  • Preparation of isocardiospermin-5-p-hydroxybenzoate and its application in the preparation of drugs for treating rheumatoid arthritis
  • Preparation of isocardiospermin-5-p-hydroxybenzoate and its application in the preparation of drugs for treating rheumatoid arthritis
  • Preparation of isocardiospermin-5-p-hydroxybenzoate and its application in the preparation of drugs for treating rheumatoid arthritis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1. Preparation of Isocardiospermin-5-p-hydroxybenzoate

[0025] Take the pearl plum medicinal material, crush it into the coarsest powder, add 20 times the amount of 95% ethanol, soak and extract 1 to 3 times, each time about 10 hours, combine the extracts, filter, dealcoholize and concentrate to about 20% ethanol concentration, add sample On the AB-8 type weakly polar macroporous adsorption resin column, first eluted with 20% ethanol solution for 5 column volumes to remove impurities, and then eluted with 95% ethanol for 4 column volumes, and collected the 95% ethanol eluted fraction. After drying under reduced pressure, load on a 100-200 mesh silica gel column, using dichloromethane-methanol as the elution system, stepwise elution according to methanol concentration from low to high, collect the eluted fraction with methanol concentration of 10-25%, concentrate and crystallize , Filter, take the filtrate, continue to perform silica gel column chromatography accor...

Embodiment 2

[0026] Example 2. Preparation of Isocardiospermin-5-p-hydroxybenzoate

[0027] Take the pearl plum medicinal material, crush it into the coarsest powder, add 20 times the amount of methanol, soak and extract 1 to 3 times, each time about 10 hours, combine the extracts, filter, dealcoholize and concentrate to an appropriate volume, and make up to about 20% alcohol concentration , Apply the sample to D-101 non-polar macroporous adsorption resin column, first elute with 20% methanol solution for 5 column volumes to remove impurities, then elute with 90% methanol for 4 column volumes, and collect 90% methanol wash Remove the part, dry it under reduced pressure and load it on a silica gel column of 100-200 mesh. Use dichloromethane-methanol as the elution system to elute in stages from low to high methanol concentration. Collect the eluted fraction with methanol concentration of 10-25%. Concentrate, crystallize, filter, take the filtrate, and continue to perform silica gel column chro...

Embodiment 3

[0028] Example 3. Confirmation of the structure of Isocardiospermin-5-p-hydroxybenzoate

[0029] 1. Apparatus and materials

[0030] Jasco P-1020 digital polarimeter, Agilent TOF / 6500 high-resolution mass spectrometer, Shimadzu UV-2401 visible-ultraviolet spectrophotometer, nuclear magnet is Bruke Avance III 500 NMR spectrometer, melting point analyzer is Yanaco MP53 (melting point not Correction). The sample of Isocardiospermin-5-p-hydroxybenzoate was prepared according to the steps in Example 1 above.

[0031] 2. Compound structure identification

[0032] Colorless viscous oil (methanol), easily soluble in dimethyl sulfoxide, methanol, slightly soluble in ethyl acetate, acetone, chloroform, water, insoluble in petroleum ether, -7.3 (c0.43, methanol). Positive ion ESI-MS m / z: 396[M+H] + , 418[M+Na] + , 813[2M+Na] + ; Negative ion ESI-MS m / z: 394[M-H]-, 430[M+Cl] - , 789[2M-H] - . Positive ion HR-ESI-MS m / z: measured value 418.1106 [M+Na] + , The calculated value 418.1114(C 18 H 2...

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Abstract

The invention relates to a chemical structure and preparing method of the compound isocardiospermin-5-p-hydroxybenzoate and application of the compound to preparation of drugs for treating rheumatoid arthritis. Isocardiospermin-5-p-hydroxybenzoate is a novel compound prepared from the traditional Chinese medicine Sorbaria sorbifolia (L.) A. Brown. through purification by the applicant of the invention. The compound can remarkably suppress the level of PEG2 and NO in serum of adjuvant arthritis rats. The activity of the compound is close to that of tripterygium glycosides of the same dose, and the compound can be used for preparing drugs for treating rheumatoid arthritis. The chemical structure, preparing method and anti-RA activity of the compound are disclosed for the first time, thus having prominent and substantive features.

Description

Technical field [0001] The invention relates to the structure and preparation method of Isocardiospermin-5-p-hydroxybenzoate, and the application of Isocardiospermin-5-p-hydroxybenzoate in the preparation of drugs for treating rheumatoid arthritis. Background technique [0002] Rheumatoid arthritis (RA) is a heterogeneous, systemic, and autoimmune disease with symmetric polyarthritis as the main clinical manifestation. It is a highly heterogeneous disease under the interaction of environmental factors, genetic background and the two. Qualitative autoimmune diseases. RA is one of the main causes of human incapacity and disability. The average worldwide incidence rate is 0.2% to 1.2%, and the prevalence rate in my country is 0.2% to 0.93%. The treatment of RA patients requires long-term medication to control the course of the disease and improve symptoms. The treatment cost is high and the social burden is heavy. At present, the drugs used clinically to treat RA mainly include no...

Claims

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Application Information

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IPC IPC(8): A61K31/7028C07H15/10C07H1/08A61P29/00A61P19/02
CPCA61K9/205A61K9/2059A61K9/4866A61K31/7028C07H1/08C07H15/10
Inventor 曲桂武吴长景张菡菡孙书勤郝玉玲孙亚楠张丽
Owner BINZHOU MEDICAL COLLEGE
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