Caffeoyl derivative and use of coffeeoyl derivative in preparing drugs against respiratory syncytial viruses

An anti-respiratory and syncytial virus technology, applied in the field of medicine, can solve the problems of high cost, high toxicity and side effects, and no specific prevention and control measures, and achieve good application prospects and novel mechanism of action

Inactive Publication Date: 2011-10-19
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there are no effective specific prevention and treatment measures for RSV infection. The nucleoside drug ribavirin is the only chemical drug approved by the FDA for the treatment of RSV infection. not

Method used

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  • Caffeoyl derivative and use of coffeeoyl derivative in preparing drugs against respiratory syncytial viruses
  • Caffeoyl derivative and use of coffeeoyl derivative in preparing drugs against respiratory syncytial viruses
  • Caffeoyl derivative and use of coffeeoyl derivative in preparing drugs against respiratory syncytial viruses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Grind the dried roots of Glycyrrhizae (collected from Guangdong and identified by Mai Zhenqiu, a senior engineer of Guangzhou Medicinal Materials Company), use 12 times the mass of Glycyrrhizae to percolate and extract with an ethanol aqueous solution with a concentration of 95% by mass, and extract the extract by rotating Concentrate under reduced pressure with an evaporator until there is no alcohol smell to obtain the total extract, suspend the total extract with 2 times the volume of distilled water, sequentially extract with petroleum ether, ethyl acetate and n-butanol, and recover the solvent under reduced pressure to obtain petroleum ether respectively Part, ethyl acetate part and n-butanol part; the n-butanol part is segmented by D101 macroporous adsorption resin column, and gradient elution is carried out with ethanol aqueous solution with a mass percentage concentration of 0-95%, and the collected mass percentage concentration is 20-95%. The eluate was eluted w...

Embodiment 2

[0032] Example 2: In vitro anti-RSV activity of 1α, 2β-O-dicaffeoylcyclopent-3β-ol

[0033] (1) Cells, viruses and experimental materials: Respiratory syncytial virus (RSV, Long strain), host cells are laryngeal carcinoma cells (Hep-2 cells); positive control drug is ribavirin (ribavirin); cells grow at a mass percentage concentration 10% fetal bovine serum (FBS) in the MEM medium; the maintenance solution is the MEM medium containing 1% FBS in mass percent concentration.

[0034] (2) Preparation of sample solution: 1α obtained in Example 1, 2β-O-dicaffeoylcyclopent-3β-alcohol and ribavirin were prepared into solutions with a concentration of 40 mg / mL with dimethyl sulfoxide (DMSO), respectively. The samples were then prepared into 200 μg / mL and 10 μg / mL sample solutions with maintenance solution, which were used for cytotoxicity and antiviral activity experiments, respectively.

[0035] (3) measure the cytotoxicity of compound with tetrazolium salt (MTT) colorimetry:

[003...

Embodiment 3

[0043] Example 3: Determination of in vitro anti-RSV activity of 1α, 2β-O-dicaffeoylcyclopent-3β-ol combined with ribavirin

[0044] (1) Cells, viruses and experimental materials: Respiratory syncytial virus (RSV, Long strain), host cells are laryngeal carcinoma cells (Hep-2 cells); positive control drug is ribavirin (ribavirin); cells grow at a mass percentage concentration 10% fetal calf serum (FBS) MEM medium; the maintenance solution is 1% FBS MEM medium.

[0045] (2) Preparation of sample solution: 1α obtained in Example 1, 2β-O-dicaffeoylcyclopent-3β-ol sample and ribavirin sample were prepared with dimethyl sulfoxide (DMSO) to form a concentration of 40mg / mL 1α, 2β-O-dicaffeoylcyclopent-3β-ol and ribavirin were prepared into 0.31μg / mL and 0.62μg / mL solutions with maintenance solution, and then the two were mixed at a volume ratio of 1:1 into the sample solution to be tested.

[0046] (3) The cytopathic effect reduction assay was used to measure the antiviral activity ...

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Abstract

The invention discloses a coffeeoyl derivative, a preparation method and a use thereof. The caffeeoyl derivative is 1alpha, 2beta-O-dicaffeoylcyclopentan-3beta-ol having a structure represented by a formula (I), and can be extracted and separated from a traditional Chinese medicine of scabrous elephantfoot herb. The coffeeoyl derivative can be provided for preparing drugs for preventing and treating respiratory syncytial viruses (RSV). In vitro antiviral experiments reveal that: compared to a general clinical antiviral drug of ribavirin, the 1alpha, 2beta-O- dicaffeoylcyclopentan-3beta-ol has stronger anti-RSV activity and lower toxicity on host cells; when the 1alpha, 2beta-O- dicaffeoylcyclopentan-3beta-ol is combined with the ribavirin, a synergistic interaction is provided. Therefore, the 1alpha, 2beta-O-dicaffeoylcyclopentan-3beta-ol has high-performance, low toxic anti-RSV activity with novel mechanism of action, and has good application prospect.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a caffeoyl derivative, a preparation method thereof and an application in preparation of an anti-respiratory syncytial virus infection drug. Background technique [0002] Elephantopus scaber (Elephantopus scaber) is a plant of the genus Elephantopus in the family Compositae, also known as the head of the gallbladder, the gallbladder, and the scaber. It is mainly distributed in South China and Southwest China. , the effect of dampness, folks are used to treat tonsillitis, pharyngitis, colds, urinary tract infections, dermatitis and hepatitis and other diseases, included in the 1977 edition of "Chinese Pharmacopoeia". The main chemical constituents in G. chinensis are sesquiterpenoids, flavonoids and caffeoylquinic acid compounds. Modern pharmacological studies have shown that the crude extract of Glycyrrhizae has antiviral, antibacterial, anti-tumor and antipyretic e...

Claims

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Application Information

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IPC IPC(8): C07C69/732C07C67/56C07C67/58A61K31/216A61P31/14A61P11/00
Inventor 李药兰叶文才王国才王英张晓琦张冬梅
Owner JINAN UNIVERSITY
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