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Novel 23-oleanolic acid compound as well as preparation method and application of compound in preparation of glycosidase inhibitor medicine

A technology for reducing oleanberries and compounds, which is applied in the field of natural medicinal chemistry, can solve the problems of insufficient pharmacological activity and ingredients, and achieves the effects of good market prospect, rich material sources and simple preparation process.

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

It has been reported in the literature that the plants of the genus Akebia have anti-inflammatory, diuretic and other pharmacological functions, and are rich in compounds such as triterpenes and nortriterpenes, but the research on pharmacological activities and components is generally not deep enough

Method used

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  • Novel 23-oleanolic acid compound as well as preparation method and application of compound in preparation of glycosidase inhibitor medicine
  • Novel 23-oleanolic acid compound as well as preparation method and application of compound in preparation of glycosidase inhibitor medicine
  • Novel 23-oleanolic acid compound as well as preparation method and application of compound in preparation of glycosidase inhibitor medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: Preparation of 2-hydroxy-3-carbonyl-23-norolean-1,4,12-triene-28-acid in Akebia clover fruit

[0025] 1.1 Instruments and reagents

[0026]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 MDSSCIEXAPI2000LC / MS / MS instrument from Applied Biosystems, USA, and uses methanol as solvent for direct sample determination; 1 HNMR spectrum and 13 The CNMR spectrum was measured using a Bruker DRX-400 nuclear magnetic resonance instrument with tetramethylsilane as an internal standard. The color development method adopts 10% sulfuric acid ethanol solution or sulfuric acid vanillin treatment, and then hea...

Embodiment 2

[0038] Example 2: Preparation of 2-hydroxy-3-carbonyl-23-norolean-1,4,12-triene-28-acid in the stems and leaves of Akebia trifoliata

[0039] 2.1 Instruments and reagents: same as Example 1

[0040] 2.2 Plant source and identification: same as Example 1

[0041] 2.3 Extraction and separation

[0042] 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 total extract of petroleum ether with chloroform / methanol (100mL) with a volume ratio of 1:1, add normal phase silica gel (80-100 mesh) and mix...

Embodiment 3

[0044] Take the stems, leaves or fruits of Akebia akebiae, Akebia changxu, Akebia basilicate or Akebia trilobata 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 ,20-Trihydroxy-29-norolean-12-ene-28-oic acid.

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Abstract

The invention discloses a compound 2-hydroxyl-3-carbonyl-23-oleanolic acid-1,4,12-triene-28-acid as well as a preparation method and application of the compound preparation of a glycosidase inhibitor medicine. An alpha-glucosidase inhibitor with high efficiency is extracted and separated from an akebia plant, a plant material is rich in source, an extraction preparation method is easy to operate, the plant can be used for a long time without being damaged when extraction is performed by adopting a plant fruit, and thus the economic benefit can be increased, and the environment friendliness is achieved; the monomeric compound is stable and easy to store. Pharmacological experiments prove that the inhibitory activity of the compound 2-hydroxyl-3-carbonyl-23-oleanolic acid-1,4,12-triene-28-acid is stronger than that of a first-grade diabetes drug acarbose by about 16 times, and thus the compound 2-hydroxyl-3-carbonyl-23-oleanolic acid-1,4,12-triene-28-acid can be expected to be further developed into a medicine for clinically treating type 2 diabetes mellitus and is good in prospect.

Description

Technical field: [0001] The invention belongs to the field of natural medicinal chemistry, and in particular relates to a new 23-noroleanolic acid compound, namely 2-hydroxy-3-carbonyl-23-norolean-1,4,12-triene-28 - the acid, the 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] 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. 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 causing more and more serious losses to our peopl...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61K31/56A61P3/10
Inventor 谭建文王晶周忠玉任慧徐巧林
Owner SOUTH CHINA BOTANICAL GARDEN CHINESE ACADEMY OF SCI
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