Pharmaceutical use of 1 beta-hydroxy ilexolic acid for inhibiting hepatitis virus

A technology of hydroxypearic acid and hepatitis B virus, applied in antiviral agents, drug combinations, digestive system, etc., can solve problems such as reducing hepatitis B surface antigen, and there are no anti-hepatitis B virus drugs for hepatitis B virus infectious diseases

Inactive Publication Date: 2011-04-20
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The present inventor made further research on the basis of the prior art, and mainly screened the antiviral activity of the phytochemical monomer components, and found that a eucalyptus-type sesquid Terpene acid has significant anti-hepatitis B virus while reducing the effect of hepatitis B surface antigen, and through literature review, so far, there is no report about the compound for treating hepatitis B virus infectious diseases and preparing anti-hepatitis B virus drugs

Method used

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  • Pharmaceutical use of 1 beta-hydroxy ilexolic acid for inhibiting hepatitis virus
  • Pharmaceutical use of 1 beta-hydroxy ilexolic acid for inhibiting hepatitis virus
  • Pharmaceutical use of 1 beta-hydroxy ilexolic acid for inhibiting hepatitis virus

Examples

Experimental program
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Effect test

preparation example Construction

[0019] For the preparation method of the eucalyptane-type sesquiterpene acid represented by the formula (1), see the published articles by researchers such as the inventor (Ous, L. et al. Nat Prod Lett 1998, 12:231; Zheng Qunxiong, Zhao Yu et al., J Nat Prod, 2003, 66(8): 1078.) The compound of formula (1) was prepared according to the method described in the literature, and the spectral data of the compound of formula (1) obtained by purification were consistent with the reported values ​​in the literature.

[0020] The spectral data of the compound of formula (1) we obtained are as follows: colorless needle crystal, melting point: 172-173°C (methanol); 1 H-NMR (deuterated pyridine, 400 MHz) δ 6.24 (1H, brs), 5.74 (1H, brs), 3.66 (1H, dd, J=12.5, 4.0 Hz), 2.91 (1H, ddd, J=13.0 , 12.5, 4.0, 4.0 Hz), 2.64 (1H, ddd, J=13.5, 13.0, 3.6 Hz), 2.36 (1H, ddd, J=13.5, 4.5, 2.5 Hz), 1.98 (1H, m), 1.96 ( 2H, m), 1.82 (1H, m, ), 1.72 (1H, dd, J=13.0, 3.6 Hz), 1.70-1.90 (2H, m), 1.64 (1H,...

Embodiment 1

[0022] Example 1 : Inhibitory effect of compound of formula (1) on hepatitis B surface antigen (HBsAg) secreted by HepG2.2.15 cells

[0023] 1) Cell culture:

[0024] HepG2.2.15 cells were cultured in DMEM medium containing 10% inactivated fetal bovine serum, 100U / ml penicillin, 100μg / ml streptomycin, and 100μg / ml G418 at 37°C, 5% CO 2 , cultured in an incubator with 100% relative humidity. 2) The inhibitory effect of the compound of formula (1) on the growth of HepG2.2.15 cells was determined by MTT method:

[0025] Take HepG2.2.15 cells in logarithmic growth phase and dilute the cells to 1 × 10 with culture medium 5 / ml, seeded in 96-well cell culture plates, 100 μl per well, at 37°C, 5% CO 2 , after culturing in a 100% relative humidity incubator for 24 hours, the compound of formula (1) diluted with culture medium was added at concentrations of 1000 μg / ml, 200 μg / ml, 40 μg / ml and 8 μg / ml, 200 μl per well, each The concentration was set up in three duplicate wells, place...

Embodiment 2

[0033] Example 2 : Inhibitory effect of the compound of formula (1) on the replication of hepatitis B virus deoxyribonucleic acid (HBV-DNA) secreted by HepG2.2.15 cells

[0034] 1) Cell culture:

[0035] The method is the same as in Example 1.

[0036] 2) The inhibitory effect of the compound of formula (1) on the growth of HepG2.2.15 cells was determined by MTT method:

[0037] The method is the same as in Example 1.

[0038] 3) To determine the inhibitory effect of the compound of formula (1) on the replication of hepatitis B virus deoxyribonucleic acid (HBV-DNA).

[0039] Take HepG2.2.15 cells in logarithmic growth phase and dilute the cells to 1 × 10 with culture medium 5 / ml, seeded in 96-well cell culture plates, 100 μl per well, at 37°C, 5% CO 2 , after culturing for 24 hours in an incubator with 100% relative humidity, the compound of formula (1) diluted with the medium was added at the concentrations of 100 μg / ml, 20 μg / ml and 40 μg / ml, 200 μl per well, and each...

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Abstract

The present invention relates to an eudesmane type sesquiterpene derivative 1 beta-hydroxyilicic acid having a structure of formula (1), namely 1 beta-hydroxy-5 alpha H-eudesmane-11 (13)-ene-12-acid, a medicinal salt or solvent compound thereof and medicinal application of the medicine composition for preparing medicines capable of curing hepatitis B virus infective disease and resisting hepatitis B virus. Said invention also provides its chemical structure formula. The compound of formula (1) has stronger inhibition to the replication of the HBV-DNA and the HBsAg secreted by HepG2.2.15 cells, and the inhibition ability to the HBsAg exceeds positive control Lamivudine at the same dosage. The compound has inhibition activity to the HBV-DNA at concentration of 100mu g / mL, 20mu g / mL and 4mu g / mL, and belongs to non-nucleoside anti-HBV natural product, which is expected to apply to prepare the medicine for curing the hepatitis B virus infective disease.

Description

technical field [0001] The present invention relates to eucalyptane-type sesquiterpene derivative 1β-Hydroxyilic acid (1β-Hydroxyilicic acid), namely 1β-hydroxy-5αH-cineole-11(13)-ene-12-acid, in the preparation of medicine for treating hepatitis B virus infection disease medicinal use in. technical background [0002] Hepatitis B is an infectious disease caused by the hepatitis B virus. It is transmitted through blood and body fluids and has a chronic carrier state. The disease is widely prevalent in my country, and the infection rate of the population is high, reaching over 35% in some areas. According to relevant data, the number of patients who tested positive for hepatitis has reached 189 million, while the number of people who should seek medical attention (carriers) is nearly 400 million. It is one of the most serious infectious diseases that endanger people's health. The clinical manifestations of hepatitis B are diverse, and it is easy to develop into chronic h...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/192A61P1/16A61P31/12C07C59/46
Inventor 赵昱李校堃黄可新巫秀美孙先凤约阿施·史托克希特李海波
Owner WENZHOU MEDICAL UNIV
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