Oleanolic acid-type saponin compound and composition thereof

A technology of oleanolic acid and saponins, which is applied in the field of oleanolic acid type saponins and compositions thereof, can solve the problems of low oral bioavailability, large irritating side effects of the gastrointestinal tract, etc. Side effects, high bioavailability effect

Pending Publication Date: 2018-01-26
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to provide oleanolic acid type saponins and their compositions. According to the prodrug design strategy and bionic principles, β-hedera saponin and related natural products are used as lead compounds to design its C-3 sugar chain structure, Carboxyl groups at the C-28 position are respectively modified with glycosyl structures to solve the problems of large gastrointestinal irritating side effects and low oral bioavailability

Method used

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  • Oleanolic acid-type saponin compound and composition thereof
  • Oleanolic acid-type saponin compound and composition thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: Preparation of oleanolic acid saponins S1-S4

[0027] Prepared with reference to the method reported in the literature of the present invention: Liming Wang, et al. Synthesis and cytotoxicity of oleanolic acid trisaccharide saponins. Carbohydrate Research, 2017, 442:9-16.

[0028] Dissolve L-arabinose, L-rhamnose (L-rhamnose, L-Rha) and D-glucose (D-glucose, D-Glc) in pyridine respectively, add benzoyl chloride dropwise under ice bath, and then rise to The whole benzoyl-protected monosaccharide can be obtained after overnight reaction at room temperature. 1-bromoglycosyl donor compounds (10a, 10b, 10c) can be obtained by reacting perbenzoyl sugar with 33% hydrobromic acid (acetic acid solution) at room temperature.

[0029] (S1) 3-O-α-L-rhamnopyranosyl (1→2)-α-L-arabinopyranosyl oleanolic acid

[0030] The compound 3-O-[2″,3″,4″-tribenzoyl-α-L-rhamnosyl (1→2)-3′,4′-diacetyl]-α-L- Arabinosyl oleanolic acid (18) (200mg, 0.181mmol) dissolved in CH 2 Cl 2...

Embodiment 2

[0037] Embodiment 2: Separation of monomeric compound in Huang Hua Pai Jiang

[0038] Prepared with reference to the method reported in the literature of the present invention: Gao Liang, Research on the chemical constituents of Huanghua Patitima, Master Thesis of Soochow University, 2011.

[0039]From Huanghua Paijiang, the following compounds P1~P9 can be isolated and obtained: 3-O-β-D-xylopyranose (1→3)-α-L-rhamnopyranose (1→2)-β- D-xylopyranose oleanolic acid 28-O-β-D-glucopyranose (P1); 3-O-β-D-glucopyranose (1→4)-β-D-glucopyranose Xylose (1→3)-α-L-rhamnopyranose (1→2)-β-D-xylopyranose oleanolic acid 28-β-D-glucopyranose side (P2); 3-O-α-L-rhamnopyranose (1→2)-β-D-xylopyranose oleanolic acid 28-O-β-D-glucopyranose side (P3); 3- O-β-D-xylopyranose(1→3)-α-L-rhamnopyranose(1→2)-α-L-arabinopyranose oleanolic acid 28-O-β-D -Glucopyranoside (P4); 3-O-β-D-xylopyranose(1→3)-α-L-rhamnopyranose(1→2)-β-D-xylopyranose Sugar oleanolic acid 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopy...

experiment example 3

[0040] Experimental Example 3: Investigation of the anti-inflammatory effect of the compound

[0041] Take the patronarin compound in Example 2 for testing. Take 20-25g mice (10 mice / group), and randomly divide them into five groups: P1-P9 group (100mg / kg), oleanolic acid control group (100mg / kg) and model group. Two hours after the last dosing, apply 25 microliters of xylene evenly to the right ear of the mouse, kill the mouse half an hour later, use a 6mm diameter puncher, take the same parts of the left and right ears of the mouse, and weigh them with an analytical balance . The weight of the removed right ear minus the weight of the left ear was the degree of swelling, the mean and standard deviation of the control group and the treatment group were calculated, and the t test was used to compare the significance of the differences between the groups. Calculate the swelling inhibition rate according to the following formula:

[0042] Swelling inhibition rate (%)=[1-avera...

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Abstract

The invention discloses an oleanolic acid-type saponin compound. The oleanolic acid-type saponin compound has a structure shown in the formula (I). In the formula (I), R1 represents -H or -OH, R2 represents alpha-OR3 or beta-OR3 and R3 represents -H or one or two of monosaccharide groups. The oral pharmaceutical composition can be used for treating inflammation and tumors, can be used as a prodrug, prevents 28-carboxy-substituted saponin-caused gastrointestinal side effects and has the effect of diminishing inflammation.

Description

technical field [0001] The invention specifically relates to an oleanolic acid type saponin compound and a composition thereof. Background technique [0002] Finding anti-tumor and anti-inflammatory drugs from traditional Chinese medicine and natural products is an effective method. Oleanolic acid and its glycosides belong to the natural products of pentacyclic triterpenoids, which are widely distributed in herbal medicines such as Ligustrum lucidum, Patella, and Pulsatilla, and have various pharmacological effects such as anti-inflammatory, anti-tumor, and anti-hyperlipidemia. Aranolic acid has been used in the treatment of acute chemical liver injury, chronic cirrhosis and liver fibrosis. In recent years, a large number of literatures have reported that oleanolic acid saponins have been isolated from herbal medicines such as ivy, Patonia, and Pulsatilla, which have good anti-inflammatory effects, and found that the free β- Compounds such as hedera saponin show good antit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/256C07J63/00A61K31/704A61P35/00A61P29/00A61P1/00A61K9/00
Inventor 刘江云李雅丽王黎明高亮王增尚苏胜郝丽莉
Owner SUZHOU UNIV
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