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Medical use of 1beta-keto-5, 11(13)-diene eudesmane-12-acid for inhibiting hepatitis B virus

A diene eucalyptane and drug technology, applied in the field of natural product eucalyptane-type sesquiterpene acid derivatives, can solve the problem of reducing hepatitis B surface antigen

Inactive Publication Date: 2010-12-08
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The present inventor has made further research on the basis of the prior art, and mainly screened the antiviral activity of this kind of phytochemical monomer components, and found that a class of medicinal plants extracted from the genus Hexarrhizae has 1β-oxo -5,11(13)-diene eucalyptane-12-acid skeleton eucalyptane-type sesquiterpene acid has significant anti-hepatitis B virus effect, and this type of eucalyptane-type sesquiterpene acid has the effect of reducing hepatitis B surface antigen at the same time , and through literature review, so far, there is no report on the treatment of hepatitis B virus infectious diseases and the preparation of anti-hepatitis B virus drugs by this type of compound

Method used

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  • Medical use of 1beta-keto-5, 11(13)-diene eudesmane-12-acid for inhibiting hepatitis B virus
  • Medical use of 1beta-keto-5, 11(13)-diene eudesmane-12-acid for inhibiting hepatitis B virus
  • Medical use of 1beta-keto-5, 11(13)-diene eudesmane-12-acid for inhibiting hepatitis B virus

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preparation example Construction

[0022] The preparation method of the eucalyptane-type sesquiterpene acid shown in this formula (1) can refer to the articles published by researchers such as the inventor (Li Shunlin, Ding Jingkai, Yunnan Plant Research, 1996, 6 (3), 349; Zhao Yu ( Yu Zhao) etc., J Nat Prod, 1997,60 (6): 645.) The present invention prepares the compound of formula (1) according to the method described in the literature, and its spectral data of the compound 1-a obtained by purification is the same as that of 1β in the above-mentioned literature. -hydroxy pterodontic acid, that is, 1β-hydroxy malodontic acid, was consistent with the reported value. Here we follow its scientific name 1-a compound as 1β-hydroxyl-5,11(13)-diene eucalyptus-12-acid, its English name is: 1β-hydroxy-5,11(13)-dien- eudesman-12-oic acid. The spectral data of the purified compound 1-b is consistent with the reported value of pterodontoside A, that is, suldalin A, in the above-mentioned literature. Here we follow its sc...

Embodiment 1

[0026] Example 1 : Inhibition of formula (1) compound 1-a and 1-b on the hepatitis B surface antigen (HBsAg) secreted by HepG2.2.15 cells

[0027] 1) Cell culture:

[0028] 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.

[0029] 2) The inhibitory effect of compounds 1-a and 1-b of formula (1) on the growth of HepG2.2.15 cells was determined by MTT method:

[0030] 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 formula (1) compound 1-a and 1-b diluted with culture medium, the concentration is 1000 μg / ml, 200 μg / ml, 40 μg / ml and 8 μg / ml respectively , 200 μl per well, set three duplicate...

Embodiment 2

[0038] Example 2 : formula (1) compound 1-a and 1-b are to HepG2.2.15 cell secreted hepatitis B virus deoxyribonucleic acid (HBV-DNA) duplication effect

[0039] 1) Cell culture:

[0040] Method is with embodiment 1.

[0041] 2) The inhibitory effect of compounds 1-a and 1-b of formula (1) on the growth of HepG2.2.15 cells was determined by MTT method:

[0042] Method is with embodiment 1.

[0043] 3) measure formula (1) compound 1-a and 1-b to hepatitis B virus deoxyribonucleic acid (HBV-DNA) replication inhibitory action: get the HepG2.2.15 cell of logarithmic growth phase, cell is diluted with culture medium into 1×10 5 / ml, seeded in 96-well cell culture plate, 100 μl per well, at 37°C, 5% CO 2 After cultivating in the incubator of 100% relative humidity for 24 hours, add respectively the formula (1) compound 1-a and 1-b diluted with the culture medium, the concentration is respectively 100 μg / ml, 20 μg / ml and 40 μg / ml, each hole 200μl, set three duplicate wells for...

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Abstract

The invention involves A 1- beta-keto-5, 11(13)-diene eudesmane-12-acidum who has the structure as formula (1) shows and its medical salt, or solvate and its drug combinations and its medical usage in reducing hepatitis B surface antgien and inhibiting replication activity of aethyl- hepatovirus HBV-DNA medicinal. The invention compounds has strong inhibitory action in hepatitis B surface antgien(HBsAg) externalized by HepG2.2.15 cells and replication of aethyl- hepatovirus deoxyribonucleotide (HBV-DNA) in vitro, its inhibiting ability against HBsAg surpasses that of positive control Lamivudine in the same dose; it has obvious inhibiting ability against replication of aethyl- hepatovirus HBV-DNA under the concentration of 100 mu g / mL,20 mug / mL and 4 mug / mL DNA, it belongs to anti- aethyl- hepatovirus natural products of superactive non-nucleoside, can be expected for producing drugs for treating aethyl- hepatovirus infected disease.

Description

technical field [0001] The invention relates to the application of a class of natural product eucalyptane-type sesquiterpene acid derivatives, namely 1β-oxo-5,11(13)-diene eucalyptane-12-acid, in the preparation of medicines for treating hepatitis B virus infection. technical background [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 c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/192A61K31/704A61K36/28A61P1/16A61P31/12C07C59/46C07H15/203
CPCY02A50/30
Inventor 赵昱李校堃黄可新李海波巫秀美孙先凤郝小江孙汉董约阿施·史托克希特
Owner WENZHOU MEDICAL UNIV
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