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Novel 2,3-dihydroxyl-30-noroleanolic acid as well as preparation method and application thereof in preparing glycosidase inhibitor medicament

A technology for reducing olean seeds and dihydroxyl groups, which is applied in the directions of drug combinations, medical preparations containing active ingredients, and pharmaceutical formulations, can solve the problems of insufficient depth of chemical components and pharmacological activities, and achieve good market development prospects and material sources. Rich and wide range of potential applications

Active Publication Date: 2015-06-24
SOUTH CHINA BOTANICAL GARDEN CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Studies have shown that Akebia genus plants are rich in triterpenoids and nortriterpenoids, but the research on their chemical constituents and pharmacological activities is still not deep enough

Method used

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  • Novel 2,3-dihydroxyl-30-noroleanolic acid as well as preparation method and application thereof in preparing glycosidase inhibitor medicament
  • Novel 2,3-dihydroxyl-30-noroleanolic acid as well as preparation method and application thereof in preparing glycosidase inhibitor medicament
  • Novel 2,3-dihydroxyl-30-noroleanolic acid as well as preparation method and application thereof in preparing glycosidase inhibitor medicament

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1: Preparation of 2,3-dihydroxy-23-formyl-30-norolean-12,20(29)-diene-28-acid in Akebia clover fruit

[0024] 1.1 Instruments and reagents

[0025] The decompression concentration adopts N-1000 rotary evaporator of Tokyo Physical and Chemical Company, CCA-1110 circulating cooling box and SB-1000 electric heating constant temperature water bath; HPLC adopts Japan Shimadzu Company LC-20AT liquid chromatograph, SPD-M20A detection and Shim-PackPRC-ODS chromatographic column (particle size 5μm, pore size 12nm, 250mm×20mm); electrospray mass spectrometry (ESIMS) adopts MDS SCIEX API2000LC / MS / MS instrument from Applied Biosystems, USA, and methanol is used as solvent for direct injection Determination; 1 H NMR spectrum and 13 C NMR spectrum was determined by Bruker advance600 nuclear magnetic resonance instrument, and tetramethylsilane was used as internal standard. The color development method adopts 10% sulfuric acid ethanol solution or sulfuric acid vanillin trea...

Embodiment 2

[0037] Example 2: Preparation of 2,3-dihydroxy-23-formyl-30-norolean-12,20(29)-diene-28-acid in the stems and leaves of Akebia trifoliata

[0038] 2.1 Instruments and reagents: same as Example 1

[0039] 2.2 Plant source and identification: same as Example 1

[0040] 2.3 Extraction and separation

[0041] The sample (1.0 kg dried stem and leaf of Akebia trifoliata) was crushed and extracted three times with 95% ethanol at room temperature, and the combined filtrate was concentrated under reduced pressure to obtain the crude extract of the total extract. Suspend the crude extract of the total extract in 500ml of water, extract three times with an equal volume of petroleum ether, and concentrate the extract under reduced pressure to obtain the total extract of petroleum ether (13g). Dissolve the petroleum ether total extract with acetone (150mL), add normal phase silica gel (80-100 mesh) at a weight ratio of 1:1.5, mix the sample and evaporate to dryness, dry-pack the column (...

Embodiment 3

[0043] Take the stems, leaves or fruits of Akebia lanceolata, Akebia changxu, Akebia basilicate and Akebia clover as samples, and finally purify according to the extraction and separation methods described in Example 1 to obtain pure compounds of formula (I) 2,3 -Dihydroxy-23-aldehyde-30-norolean-12,20(29)-diene-28-oic acid.

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Abstract

The invention discloses novel 2,3-dihydroxyl-30-noroleanolic acid as well as a preparation method thereof and application thereof in preparing a glycosidase inhibitor medicament. According to the novel 2,3-dihydroxyl-30-noroleanolic acid as well as a preparation method thereof and application thereof disclosed by the invention, a strong-effect alpha-glucosidase inhibitor is extracted and separated from akebia plants, and the plants are rich in resource. Moreover, when fruit extraction is adopted, the plants are utilized for a long time without being damaged, so that not only can economic benefits be improved, but also environmental friendliness can be achieved. A pharmacological experiment shows that a compound 2,3- dihydroxyl-23-aldehyde group-nor olean-12,20(29)-diene-28-acid has in-vitro alpha-glucosidase-inhibitory activity stronger than that of a first-line diabetes medicament acarbose, is expected to be further developed into a medicament for preventing and treating type II diabetes mellitus, and has good application and development potentials.

Description

Technical field: [0001] The invention belongs to the field of natural medicinal chemistry, and specifically relates to a new 30-noroleanane acid pentacyclic triterpene compound, namely 2,3-dihydroxy-23-formyl-30-norolean-12, 20(29)-diene-28-acid, the separation and preparation method of the compound, and the application of the compound or its pharmaceutically acceptable salt or its esterified derivative in the preparation of glycosidase inhibitor drugs. Background technique: [0002] With the progress of society and the improvement of people's living standards, the incidence of diabetes is increasing worldwide. In my country, the prevalence of diabetes is more than 100 million, and it shows a trend of increasing year by year. Diabetes is a common clinical endocrine and metabolic disorder disease, which has an important correlation with the annual increase in cardiovascular diseases and cancers, and is a potentially important killer of human health. Diabetes is causing more ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00A61K31/56A61P3/10
Inventor 谭建文王晶徐巧林任慧董丽梅
Owner SOUTH CHINA BOTANICAL GARDEN CHINESE ACADEMY OF SCI
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