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A kind of triterpene saponin compound and its preparation method and application

A technology of triterpene saponins and compounds, which is applied in the field of triterpene saponins and their preparation, can solve the problems of strong toxic and side effects, difficult drug use, lack of anti-hepatic fibrosis drugs, etc., and achieve strong polarity and water solubility, Anti-hepatic fibrosis drug activity, strong anti-hepatic stellate cell proliferation effect

Active Publication Date: 2020-11-17
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Finding effective anti-hepatic fibrosis drugs is one of the current research hotspots in the fields of medicine and biology. Due to the complexity of the formation mechanism of liver fibrosis, so far, most of the drugs for the treatment of liver fibrosis are in the clinical trial stage. FDA-approved anti-hepatic fibrosis Drugs are still lacking
In addition, the anti-hepatic fibrosis chemical drugs in the prior art, such as colchicine, have strong toxic and side effects, and are not easy to use as drugs.

Method used

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  • A kind of triterpene saponin compound and its preparation method and application
  • A kind of triterpene saponin compound and its preparation method and application
  • A kind of triterpene saponin compound and its preparation method and application

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Embodiment 1

[0056] The present invention provides a triterpene saponin compound or a pharmaceutically acceptable salt thereof, a compound of chemical formula (I)

[0057]

[0058]

[0059] where: R 1 , R 2 is H or OH; R 3 is H or rhamnose; R 4 is glucose or rhamnose or xylose; R 5 It is H or glucose or rhamnosyl-(1→4)-[rhamnosyl-(1→3)-]-glucosyl-.

[0060] The compound can be used as a medicine for treating liver fibrosis. The compound can be isolated and extracted from Dai medicine Bamboo-leaf Bupleuri. The present invention provides a pharmaceutical composition, comprising the above compound and a pharmaceutically acceptable carrier or excipient.

Embodiment 2

[0062] Prepare the preparation method of triterpene saponins compound of the present invention, comprise the following steps:

[0063] Step 1: Weigh the medicinal material of Bupleurum bupleuri, crush it, and extract it under reflux with 10 times the volume of 75% ethanol and 5% ammonia solution to obtain the filtrate;

[0064] Step 2 removes the ethanol in the filtrate, and sequentially uses petroleum ether, ethyl acetate, n-butanol solution to extract, and obtains petroleum ether, ethyl acetate, n-butanol, and the water layer extraction part;

[0065] Step 3 For the extraction part of the water layer, use macroporous adsorption resin AB-8 to elute with ethanol-water (0:100-100:0) gradient, and collect 20:80, 40:60, 60:40, and 80: 20 The eluate of the four parts was detected and analyzed by LC-MS, and the second part (40:60) was the main enriched component of glycoside compounds.

[0066] Step 4 Pass the 40:60 eluted part through forward silica gel column chromatography, and...

Embodiment 3

[0069] When R 1 for OH, R 2 , R 3 for H, R 4 for rhamnose, R 5 For glucose, the compound is 3-O-β-D-glucosyl-(1→6)-[-α-L-rhamnosyl-(1→3)]-β-D-glucosyl-11, 13(18)-diene-(16β,29)-dihydroxy-28-O-β-D-glucosyl-oleanane (defined in the present invention as: compound 1), its chemical formula is as follows:

[0070]

[0071] Compound 1 is a white amorphous powder, soluble in methanol; HRMS [M-H]-peak m / z 1103.567 (calculated value C 54 h 87 o 23 - is 1103.565), molecular formula: C 54 h 88 o 23 .

[0072] Analytical data of compound 1: as figure 1 As shown, compound 1's 1 The seven angle methyl signals given in the H NMR (176MHz, methanol-D4) spectrum δH 0.76(3H, s), 0.85(3H, s), 0.86(3H, s), 0.94(3H, s), 1.08 (3H, s), 1.26(3H, d), 1.29(3H, d) are the characteristic signals of triterpenoid saponins, in which there is a methyl signal split into doublets at the chemical shift of 1.29 in the H spectrum, which is speculated to be furfural Methyl signal on sugar or rhamnos...

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Abstract

The invention provides a triterpenoid saponin compound or a pharmaceutically acceptable salt thereof. The triterpenoid saponin compound has a chemical formula represented by formula (I), wherein R1 and R2 are H or OH; R3 is H or rhamnose; R4 is glucose or rhamnose or xylose; and R5 is H or glucose or rhamnosyl-(1-4)-[rhamnosyl-(1-3)-]-glucosyl-. The triterpenoid saponin compound disclosed by the invention has a relatively excellent anti-hepatic stellate cell proliferation effect and an anti-hepatic fibrosis effect, and has a relatively low IC50 value for platelet-derived factor (PDGF), type Icollagen alpha1 (COL1A1), transforming growth factor-beta1 (TGF-beta1) and human alpha smooth muscle actin (alpha-SMA).

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a triterpene saponin compound and a preparation method and application thereof. Background technique [0002] The liver is the largest solid organ in the human body, and it is also an important organ for metabolic activities such as detoxifying various metabolites, synthesizing proteins, regulating glycogen storage, decomposing red blood cells, and producing hormones. Hepatic fibrosis is a damage repair response secondary to liver injury and inflammatory response caused by various chronic pathogenic factors. Its core is the imbalance of extracellular matrix synthesis and degradation, which causes pathological accumulation of excess extracellular matrix, scarring and thickening of liver tissue, and affects normal organ function. Liver fibrosis is an inevitable pathological process in the development of various acute and chronic liver diseases. If it is not effective...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00A61K31/704A61P1/16
CPCA61P1/16C07J63/008
Inventor 戴荣继罗克刘秀洁邓玉林吕芳丛林
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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