Ursolic acid-3-O-beta-D-pyranglucuronide and derivatives thereof, and preparation method and medicinal application thereof

A technology of glucopyranose and ursolic acid is applied in the field of medicine to achieve the effects of reducing absorption, good preventive and therapeutic effects, and reducing postprandial hyperglycemia

Inactive Publication Date: 2010-09-01
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Among the novel compounds with medicinal value as shown in formula (I) disclosed in this patent, the representative compound u

Method used

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  • Ursolic acid-3-O-beta-D-pyranglucuronide and derivatives thereof, and preparation method and medicinal application thereof
  • Ursolic acid-3-O-beta-D-pyranglucuronide and derivatives thereof, and preparation method and medicinal application thereof
  • Ursolic acid-3-O-beta-D-pyranglucuronide and derivatives thereof, and preparation method and medicinal application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Synthesis of ursolic acid-28-benzyl ester-3-O-β-D-(2,3,4-tribenzoyloxyglucuronomethyl)glycoside

[0053] Benzyl ursolic acid (400mg, 0.73mmol) and imidate compound (1.3eq) were dissolved in 15mL of dry dichloromethane, added Molecular sieve 3g, the suspension was stirred in an ice bath for 30 min, then a dry dichloromethane solution of TMSOTf (0.0276M, 0.4 mL) was added, the reaction solution was reacted in an ice bath for 40 min, and triethylamine was added to quench the reaction. After filtering the reaction solution, the filtrate was evaporated to dryness and directly subjected to silica gel column chromatography to obtain ursolic acid-28-benzyl ester-3-O-β-D-(2,3,4-tribenzoyloxyglucuronide methyl ester). ESI-MS m / z: 1071.53[M+Na] + ; 1 H NMR (CDCl 3 , 300MHz) δ0.60(s, 3H), 0.62(s, 3H), 0.70(s, 3H), 0.86(s, 6H), 0.94(s, 3H), 1.03(s, 3H), 2.25(d , J=12.1Hz, 1H), 3.13-3.18(m, 1H), 3.70(s, 3H), 4.31(d, J=9.8Hz, 1H), 4.89(d, J=7.8Hz, 1H), 4.96 and 5.09(d, J=12.4Hz...

Embodiment 2

[0055] Synthesis of ursolic acid-3-O-β-D-(2,3,4-tribenzoyloxyglucuronomethyl)glycoside

[0056] Dissolve ursolic acid-28-benzyl ester-3-O-β-D-(methyl 2,3,4-tribenzoyloxyglucuronate) (100mg, 0.1mmol) in THF 3mL, add Catalytic amount of palladium carbon, the reaction solution quantitatively removes the 28-position benzyl group under a hydrogen environment to obtain ursolic acid-3-O-β-D-(2,3,4-tribenzoyloxyglucuronic acid methyl ester) glycosides. ESI-MS m / z: 981.48[M+Na] + ; 1 HNMR (CDCl 3 )δ0.60(s, 3H), 0.71(s, 3H), 0.72(s, 3H), 0.86(s, 3H), 0.88(s, 3H), 0.95(s, 3H), 1.04(s, 3H ), 2.15-2.19(m, 1H), 3.13-3.18(m, 1H), 3.70(s, 3H), 4.31(d, J=9.8Hz, 1H), 4.89(d, J=7.78Hz, 1H) , 5.22(brs, 1H), 5.56-5.69(m, 2H), 5.91(t, J=9.6Hz, 1H), 7.26-7.96(m, 15H); 13 C NMR (CDCl 3 )δ15.4, 16.2, 17.0, 18.1, 21.2, 23.3, 23.5, 24.2, 27.8, 28.0, 29.7, 30.6, 33.0, 36.7, 38.7, 38.9, 39.1, 39.5, 42.0, 47.6, 48.0, 52.6, 52.8, 55.5 , 70.5, 71.9, 72.5, 72.9, 90.8, 103.3, 126.0, 128.3, 128.4, 128.9...

Embodiment 3

[0058] Synthesis of Ursolic Acid-3-O-β-D-Glucopyranoside

[0059] Dissolve ursolic acid-3-O-β-D-(2,3,4-tribenzoyloxyglucuronide methyl ester) glycoside (80 mg, 0.13 mmol) in 5 mL of dry methanol, add a catalytic amount of Sodium methoxide, stirred at room temperature for 40 minutes, cooled the reaction solution to 0°C in an ice bath, added 1 mL of 2 mol / L sodium hydroxide aqueous solution dropwise, and continued to stir the reaction solution at room temperature for 3 hours, then neutralized the reaction solution to acidity with acetic acid, After the reaction solution was evaporated to dryness under reduced pressure, it was subjected to silica gel column chromatography to obtain ursolic acid-3-O-β-D-glucopyranose. ESI-MS m / z: 631.5[M-H] - ; 1 H NMR (C 5 D. 5 N) δ0.72(s, 3H), 0.90(s, 6H), 0.93(s, 6H), 1.20(s, 3H), 1.23(s, 3H), 2.55(d, J=11.3Hz, 1H) , 3.30(m, 1H), 3.96-4.01(m, 1H), 4.22(brs, 1H), 4.49(brs, 1H), 4.91(brs, 1H), 5.39(brs, 1H); 13 C NMR (C 5 D. 5 N) δ15.6, 1...

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Abstract

The invention discloses an ursolic acid-3-O-beta-D-pyranglucuronide and pharmaceutically acceptable salts or esters thereof, and a preparation method and a medicinal application of a compound, and especially an application in preparing medicaments for resisting diabetes and complications thereof. The ursolic acid-3-O-beta-D-pyranglucuronide and pharmaceutically acceptable salts or esters thereof have obvious function of reducing blood sugar, and especially have favorable efficacy of reducing hyperglycemia after meals.

Description

Technical field: [0001] The present invention relates to the field of medicine, in particular to ursolic acid-3-O-β-D-glucopyranoside and pharmaceutically acceptable salts or esters thereof, as well as the preparation method and medical use of the compound, especially in It is used for the preparation of anti-diabetes and its complication medicine. Background technique: [0002] Pentacyclic triterpenoid saponins are various in nature, and have a wide range of pharmacological effects and important biological activities, especially in anti-inflammatory, liver protection, anti-tumor, anti-diabetes and immune regulation. characteristic. [0003] In terms of lowering blood sugar, the root and stem bark of Aralia elata are used in Japan to treat diabetes. It has anti-diabetic and anti-arthritis effects, and is also a tonic. The total triterpene saponins extracted from it have hypoglycemic and cytoprotective activities (Phytochemistry 56, 2001, 491-497). Patent JP8040912 disclos...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61K31/704A61P3/10
CPCY02P20/55
Inventor 孙宏斌郝佳柳军张璞张陆勇
Owner CHINA PHARM UNIV
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