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New 23, 29-drop oleanolic acid compound, preparation method thereof and application in preparation of glucosidase inhibitor medicines

A technology for reducing oleanberries and compounds, which is applied in the field of science, can solve the problems of insufficient depth of chemical components and pharmacological activities, and achieves the effects of good market development prospects, wide application potential and rich material sources.

Active Publication Date: 2014-04-23
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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  • New 23, 29-drop oleanolic acid compound, preparation method thereof and application in preparation of glucosidase inhibitor medicines
  • New 23, 29-drop oleanolic acid compound, preparation method thereof and application in preparation of glucosidase inhibitor medicines
  • New 23, 29-drop oleanolic acid compound, preparation method thereof and application in preparation of glucosidase inhibitor medicines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1: Preparation of 2-hydroxy-3-carbonyl-23,29-norolean-1,4,12,20(30)-tetraene-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 vanill...

Embodiment 2

[0037] Example 2: Preparation of 2-hydroxy-3-carbonyl-23,29-dinorolean-1,4,12,20(30)-tetraene-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 (Akebia trifoliate stems and leaves, dry weight 2.0 kg) was crushed and extracted three times with 95% ethanol aqueous solution at room temperature, and the combined filtrate was concentrated under reduced pressure to remove the organic solvent to obtain the crude extract of the total extract. Suspend the crude extract of the total extract in 500ml of water, then extract with an equal volume of petroleum ether, and concentrate the extract under reduced pressure to obtain the total extract of petroleum ether (24g). Dissolve the petroleum ether total extract with 1:1 chloroform / methanol (100mL), add normal phase silica gel (80-100 mesh) at a weight ratio o...

Embodiment 3

[0043] Take the stems, leaves or fruits of Akebia akebiae, Akebia changxu, Akebia basilicate and Akebia trilobata as samples, and finally purify according to the extraction and separation methods described in Example 1 to obtain the pure compound 2-hydroxyl of formula (I) -3-Carbonyl-23,29-dinorolean-1,4,12,20(30)-tetraen-28-oic acid.

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Abstract

The invention discloses new 2-hydroxy-3-carbonyl-23, 29-dinorolean-1, 4, 12, 20 (30)-tetraene-28-acid, a preparation method thereof and an application in preparation of glucosidase inhibitor medicines. An alpha-glucosidase inhibitor with strong effects is extracted and separated from an akebia plant, and plant sources are rich. Furthermore, when fruit extraction is performed, the plant can not be damaged and can be utilized for a long time, so that economic benefits are improved, and the environment-friendly effect is further achieved. Pharmacological experiments show that the in-vitro alpha-glucosidase inhibition activity of the compound, namely 2-hydroxy-3-carbonyl-23, 29-dinorolean-1, 4, 12, 20 (30)-tetraene-28-acid is about 5 times of that of a first-line diabetes medicine, namely acarbose, so that the compound is expected to be used for developing medicines for preventing and treating type II diabetes 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 23,29-noroleanane acid pentacyclic triterpene compound, namely 2-hydroxy-3-carbonyl-23,29-noroleanane-1, 4,12,20(30)-tetraen-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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/56A61P3/10
Inventor 谭建文王晶徐巧林周忠玉任慧
Owner SOUTH CHINA BOTANICAL GARDEN CHINESE ACADEMY OF SCI
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