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Eudesmane type sesquiterpenes acid and application thereof

A technology of sesquiterpene and eucalyptane type, applied in eucalyptane type sesquiterpene acid and its application field, can solve the problems of reducing hepatitis B surface antigen, and there is no anti-hepatitis B virus drug for hepatitis B virus infectious disease

Inactive Publication Date: 2009-06-03
ZHEJIANG 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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  • Eudesmane type sesquiterpenes acid and application thereof
  • Eudesmane type sesquiterpenes acid and application thereof
  • Eudesmane type sesquiterpenes acid and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] The preparation method of embodiment 1 eucalyptus type sesquiterpene acid

[0021] The present invention prepares the target compound ( A)-Pectic acid, the spectral data after purification are consistent with the reported values ​​in the literature,

[0022] The spectral data of the prepared compound is: mass spectrum EIMS: m / z252[M] - (5), 234, 219, 206, 191, 149, 81; 1 H-NMR (deuterochloroform, 400MHz) δ 6.13 (1H, brs), 5.63 (1H, brs), 2.46 (1H, dddd, J=12.0, 12.0, 3.0, 3.0Hz), 2.04 (1H, ddd, J =13.5, 12.0, 3.0 Hz), 1.45-1.55 (5H, m), 1.20-1.35 (2H, m), 1.05 (1H, brs), 0.92 (3H, s).

[0023] The structure of compound (A):

[0024]

Embodiment 2

[0025] Example 2: Inhibitory effect of compound (A) on hepatitis B surface antigen (HBsAg) secreted by HepG2.2.15 cells.

[0026] 1) Cell culture:

[0027] HepG2.2.15 cells were cultured in DMEM medium containing 10% inactivated fetal bovine serum, 100 U / ml penicillin and 100 μg / ml streptomycin, 100 μg / ml G418 at 37°C, 5% CO 2 , cultured in an incubator with 100% relative humidity.

[0028] 2) The inhibitory effect of the compound of formula (A) on the growth of HepG2.2.15 cells was measured by MTT method:

[0029]Take the HepG2.2.15 cells in the logarithmic growth phase, and dilute the cells to 1×10 with medium 5 / ml, seeded in 96-well cell culture plate, 100 μl per well, at 37°C, 5% CO 2 After cultivating in an incubator with 100% relative humidity for 24 hours, add compound (A) diluted with medium, the concentrations are 1000 μg / ml, 200 μg / ml, 40 μg / ml and 8 μg / ml, 200 μl per hole, each concentration Set up three replicate wells, placed at 37°C, 5% CO 2 , cultivated in...

Embodiment 3

[0037] Embodiment 3: Compound (A) inhibits the replication of hepatitis B virus deoxyribonucleic acid (HBV-DNA) secreted by HepG2.2.15 cells.

[0038] 1) Cell culture: the method is the same as in Example 1.

[0039] 2) Determination of the inhibitory effect of compound (A) on the growth of HepG2.2.15 cells by MTT method: the method is the same as in Example 1.

[0040] 3) Determining the inhibitory effect of compound (A) on the replication of hepatitis B virus deoxyribonucleic acid (HBV-DNA).

[0041] Take the HepG2.2.15 cells in the logarithmic growth phase, and dilute the cells to 1×10 with medium 5 / ml, seeded in 96-well cell culture plate, 100 μl per well, at 37°C, 5% CO 2 After cultivating in an incubator with 100% relative humidity for 24 hours, add compound (A) diluted with culture medium, the concentrations are 100 μg / ml, 20 μg / ml and 40 μg / ml respectively, 200 μl per hole, and each concentration is set in triplicate. Wells, placed at 37°C, 5% CO 2 , cultivated in...

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Abstract

The invention provides a eucalyptane-type sesquiterpene acid compound, whose chemical name is: 5αH-eucaine-11(13)-en-12-acid. The eucalyptane-type sesquiterpene acid compound provided by the invention has a strong inhibitory effect on the replication of hepatitis B surface antigen (HBsAg) and hepatitis B virus deoxyribonucleic acid (HBV-DNA) secreted by HepG2.2.15 cells, and its inhibition The HBsAg ability exceeds the positive control lamivudine at the same dose; it has the effect of inhibiting the replication activity of hepatitis B virus HBV-DNA, and belongs to the non-nucleoside anti-hepatitis B virus natural product, which can be used in the preparation of prevention and treatment of hepatitis B virus and reduce the surface of hepatitis B Application of antigen medicine.

Description

technical field [0001] The invention relates to the medical use of a eucalyptane-type sesquiterpene acid monomer, aspic acid, in the preparation of medicines for treating hepatitis B virus infection diseases. Background technique [0002] Hepatitis B is an infectious disease caused by the hepatitis B virus. Transmitted through blood and body fluids, with a chronic carrier state. The disease is widely prevalent in my country, and the infection rate among the population is high, and the infection rate reaches more than 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 see a doctor but have not (carriers) is nearly 400 million. It is one of the most serious infectious diseases currently endangering people's health. The clinical manifestations of hepatitis B are diverse, and it is easy to develop into chronic hepatitis and cirrhosis, and a small number of patie...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C59/11A61K31/19A61P1/16A61P31/12
Inventor 赵昱刘光明李海波巫秀美孙先凤钱金袱张荣平孙汉董郝小江约阿施·史托克希特张礼和
Owner ZHEJIANG UNIV
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