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Oleanane-type triadic compound and its preparation method and medical application

A kind of technology of oleanane type and compound, applied in the field of medicine

Inactive Publication Date: 2011-12-21
BEIHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The present invention is for the first time to obtain oleanane-type triadyl compounds from the saxifrage plant Dandingcao for the first time. Several pharmacological experiments have shown that these compounds have the ability to inhibit protein tyrosine phosphate Significant activity of enzyme 1B, after literature search, there is no report on this type of compound

Method used

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  • Oleanane-type triadic compound and its preparation method and medical application
  • Oleanane-type triadic compound and its preparation method and medical application
  • Oleanane-type triadic compound and its preparation method and medical application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Preparation of Oleanane-Type Triadic Compounds

[0076] Dried and crushed red crest grass ( Aceriphyllum rossiiEngler) root 1.5-2.5 Kg soaked in 10L methanol at room temperature for 3 days to extract once, a total of three extractions. The combined methanol extracts were concentrated under reduced pressure to obtain extract (178g). Dissolve the extract in 1.0-0.6L water, form a suspension and extract with 3.0-2.0L n-hexane, and concentrate the n-hexane extract under reduced pressure to obtain n-hexane extract (89g); pass the n-hexane extract through 200-300 Silica gel column chromatography, using n-hexane / ethyl acetate (V / V, 10:1-0:1) as the mobile phase for gradient elution, the collected separated components were detected by silica gel thin layer chromatography, and the components were the same After combining and concentrating the separated fractions, ten separated fractions from F1 to F10 are obtained? .

Embodiment 2

[0078] Compound 1 was isolated:

[0079] The fraction of F10 (1263.4 mg, 12-15% ethyl acetate) prepared in Example 1 was subjected to 200-300 mesh silica gel column chromatography, and chlorinated aromatic / acetone (V / V, 10:1-1:1) Gradient elution was carried out as the mobile phase, and the collected separated components were detected by silica gel thin-layer chromatography. The separated components with the same composition were combined and concentrated to obtain seven separated components from H1 to H7. The concentrated H1 component (191.2 mg, chlorophene / acetone, 10:1-10:2) was determined to be a monomeric compound, namely compound 1 (191.2 mg), by 400 MHz NMR detection of hydrogen spectrum. That 1 H and 13 C-NMR spectrum such as figure 1 , figure 2 .

Embodiment 3

[0081] Compound 2 was isolated:

[0082] Part H7 (466.9 mg, chlorophene / acetone, 4:5-5:5) prepared in Example 2 was subjected to 200-300 mesh silica gel column chromatography, and used for n-hexane / ethyl acetate (V / V, 15 :1-5:1) is the mobile phase for gradient elution, and the collected separated components are detected by silica gel thin layer chromatography. The separated components with the same composition are combined and concentrated to obtain six separated components from G1 to G6. The collected fraction of G5 (188.9 mg, n-hexane / ethyl acetate, 6:1) was subjected to reverse-phase high performance liquid chromatography using C 18 Column (10μm, 250×10 mm), with acetonitrile:H 2 O=50:1-100:1 (V / V) was used as the gradient elution of the mobile phase, the flow rate was 2mL / min, the column temperature was 25°C, and the detection was carried out at 210nm wavelength for 70min. The 22.3-26.9 min eluate was collected, and the collected solution was concentrated to obtain comp...

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Abstract

The invention discloses an oleanane-type triad compound, and also provides its preparation method and medical application. Acid phosphatase 1B activity of oleanane-type (oleanane-type) triad compounds, structure: R1 is hydroxyl, acetoxy, R2 is carboxyl, hydroxymethylene, R3 is methyl, carboxyl, R4 For carboxyl, methyl. Multiple in vitro protein tyrosine phosphatase 1B inhibition experiments show that the compound has obvious PTP1B inhibitory activity and can be used in the preparation of medicines for diabetes, obesity and complications.

Description

technical field [0001] The invention discloses an oleanane-type tripartite compound, and also provides its preparation method and medical application, and relates to the technical field of medicine. Background technique [0002] At present, diabetes is often divided into two types: insulin-dependent (IDDM, type 1 diabetes) and non-insulin-dependent (NIDDM, type 2 diabetes), of which type 2 diabetes accounts for 90% of diabetes. WHO predicts that the number of people with diabetes will rise from 135 million in 1995 to 300 million by 2025 due to aging population, obesity, unhealthy diet and inactive lifestyle. [0003] Type 2 diabetes is characterized by resistance to the action of insulin in insulin-sensitive tissues such as skeletal muscle, liver, and adipose tissue. Although its specific mechanism is unclear, the weakening or even blocking of insulin signaling in its transduction pathway must be directly related. PTPases play a role in multiple links in the insulin signal...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/56A61P3/10A61P3/04A61P5/50
Inventor 崔龙李志李宣善
Owner BEIHUA UNIV
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