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Polyglycosidated pentacyclic triterpene-28-acid, and preparation method and application thereof

A pentacyclic triterpene and polysaccharide technology, which is applied in the field of medicine and its preparation and application, can solve the problems of restricted application, poor water solubility, and low bioavailability, and achieve the effects of small toxic and side effects, enhanced water solubility, and good water solubility

Inactive Publication Date: 2015-12-23
JIANGXI AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, their poor water solubility and low bioavailability seriously restrict their clinical application.

Method used

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  • Polyglycosidated pentacyclic triterpene-28-acid, and preparation method and application thereof
  • Polyglycosidated pentacyclic triterpene-28-acid, and preparation method and application thereof
  • Polyglycosidated pentacyclic triterpene-28-acid, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] A kind of synthesis of 2α, 3β-2-(O-β-D-glucopyranoside) oleanane-28-acid, the specific steps are as follows:

[0039] (1) Synthesis of 2α, 3β-dihydroxy-oleanane-28-acid benzyl ester:

[0040]

[0041]2a-Hydroxyoleanolic acid (10g, 21.2mmol) and potassium carbonate (6g, 43.6mmol) were dissolved in 50mL of DMF, and 4.2mL of BnBr was added, and the reaction was stirred for 24h at a reaction temperature of 50°C. Add distilled water, wait for the solid to precipitate, filter, and dry to obtain 11.0 g of the target product, the yield is 92.0%, and the melting point is 155-157 ° C;

[0042] (2) Synthesis of 2α,3β-di-O-(2,3,4,6-4-O-benzoyl-β-D-glucopyranoside)-oleanane-28-oic acid benzyl ester :

[0043]

[0044] The product of step (1) (1 g, 1.8 mmol) and trichloroacetimidoglucose ester (2.94 g, 3.95 mmol) were dissolved in dichloromethane, and 5 drops of TMSOTf were added, and stirred at room temperature for 24 h. After filtration and concentration under reduced pres...

Embodiment 2

[0053] Synthesis of 2α,3β-di-O-(β-D-galactopyranoside)-(1→4)-(β-D-glucopyranoside)-ursane-28-acid, specific synthesis steps With embodiment 1.

[0054] Melting point: 291-293°C.

[0055] Spectral data: 1 HNMR (400MHz, DMSO-d 6 ):δ5.10(s,1H),4.47(d,J=7.5Hz,1H),4.36(d,J=7.0Hz,1H),4.18-4.15(m,2H),3.90-3.88(m, 1H),3.76-3.74(m,2H),3.62-3.59(m,4H),3.58-3.54(m,4H),3.53-3.50(m,4H),3.49-3.42(m,8H),3.33- 3.28(m,9H),3.27-3.21(m,6H),3.12-3.06(m,2H),2.13-2.12(m,2H),1.91-1.83(m,4H),1.73(s,2H), 1.55-1.39(m,8H),1.26-1.21(m,5H),1.05(s,3H),1.01(s,3H),0.88(s,6H),0.79(s,3H),0.76(s, 3H),0.74(s,3H). 13 CNMR (100MHz, DMSO-d 6 ): δ176.2, 138.8, 124.0, 104.1, 103.3, 98.3, 87.2, 81.4, 80.9, 79.2, 75.6, 75.2, 75.0, 74.8, 74.7, 74.1, 73.3, 72.8, 71.5, 70.7, 70.6, 68.2, 60.9, 60 MS( HRMS):m / z[M+Na] + calcdforC 54 h 88 o 24 Na: 1143.5558; found: .1143.5508.

Embodiment 3

[0057] The polyglycosidated pentacyclic triterpene-28-acid synthesized in Examples 1 and 2 was tested for α-glucosidase inhibitory activity and its antidiabetic activity was evaluated.

[0058] α-Glucosidase inhibition model.

[0059] The total volume of the reaction system is 250 μL, the blank reaction system: 10 μL 1U / mL α-glucosidase, 220 μL 67 mmol / LKH 2 PO 4 -K 2 HPO 4 buffer and 20 μL of 5.8 mmol / L p-nitrophenyl-α-D-glucopyranoside (PNPG) solution.

[0060] Prepare a series of concentration gradients of 2α,3β-bis-(O-β-D-glucopyranoside)-oleanane-28-acid, add to the solution containing 10 μL 1U / mL α-glucosidase and a certain amount of buffer solution, incubated at 37°C and pH=6.8 for 10 minutes, and finally 20 μL of PNPG solution was quickly added to the reaction system as a substrate. 4 parallel experiments.

[0061] Inhibition rate = [(A-(A 1 -A 2 )) / A]×100%, A is the absorbance value measured by the blank reaction system, A 1 Absorbance value measured for the ...

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Abstract

The invention discloses a polyglycosidated pentacyclic triterpene-28-acid, and a preparation method and an application thereof. The water solubility of polyhydroxypentacyclic triterpene-28-acid is further enhanced on the basis of maintaining or improving the activity of the polyhydroxypentacyclic triterpene-28-acid, and a plurality of glycosyl groups are introduced to the hydroxyl position of polyhydroxypentacyclic triterpene-28-acid and are glycosidated to synthesize a series of the polyglycosidated pentacyclic triterpene-28-acid with good water solubility. Researches show that like compounds have good in vitro alpha-glucosidase inhibition activity. The invention provides a method for screening an alpha-glucosidase inhibitor with the advantages of good water solubility, high inhibition activity, mild effects and small toxic and side effects. The screening method can be widely used in subsequent anti-diabetic clinic fields.

Description

technical field [0001] The invention relates to the technical field of medicine and its preparation and application, in particular to a polyglycosidated pentacyclic triterpene-28-acid, its preparation method and its application in the preparation of antidiabetic drugs. Background technique [0002] Diabetes is a metabolic disease characterized by chronically elevated blood sugar levels. In recent years, the morbidity and mortality have shown a rapid upward trend, becoming the third major disease that threatens human health after tumors and cardiovascular diseases. At present, the main methods of diagnosis and treatment are to control blood sugar concentration by injecting insulin and oral hypoglycemic drugs. At present, the more common chemical drugs mainly include biguanide compounds, thiazolidinediones (TZDs) and sulfonylurea compounds. Although these synthetic drugs have quick effects and obvious curative effects, they also have relatively large side effects. Therefore, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00C07H15/256C07H1/00A61P3/10
Inventor 洪艳平徐健聪上官新晨聂旭亮蒋艳陈继光吴少福胡洁芳尹小莉
Owner JIANGXI AGRICULTURAL UNIVERSITY
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