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A kind of monoterpene compound and its extraction method and application

An extraction method and compound technology, applied in the field of natural medicinal chemistry, can solve the problems of inability to cure, unsatisfactory treatment effect, poor drug efficacy, etc., and achieve good anti-hepatoma effect, significant curative effect, and significant anti-hepatitis B virus effect. Effect

Active Publication Date: 2020-07-03
SHENZHEN PEOPLES HOSPITAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Clinically, the control of HBV is mainly based on vaccination prevention. Although the vaccine is effective, once infected with hepatitis B virus, it can only be carried for life and cannot be cured. Moreover, the current treatment effect is not satisfactory
In addition to the poor curative effect of the existing chemical drugs for the treatment of liver cancer, the defects of drug toxicity and drug resistance caused by long-term use also need to be overcome urgently

Method used

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  • A kind of monoterpene compound and its extraction method and application
  • A kind of monoterpene compound and its extraction method and application
  • A kind of monoterpene compound and its extraction method and application

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Experimental program
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Effect test

Embodiment 1

[0058] Characterization of Japopenoid A

[0059] The new monoterpenoid compound provided by the present invention is light yellow oil, and HR-ESI MS (positive) gives quasi-molecular ion peak m / z 223.1324[M+H] + , suggesting that its molecular weight is 222; combined with hydrogen spectrum and carbon spectrum data (see Table 1 for details), it is determined that its molecular formula is C 13 h 18 o 3 , with a calculated unsaturation of 6.

[0060] see Figure 1~6 , through analysis, it can be seen that the carbon spectrum of this monoterpenoid compound suggests that it contains 13 carbons, including three methyl groups, four methylene groups (wherein there is an oxygen connection), one methine group, five quaternary carbons (including a carbonyl, an alkene, and two oxycarbons). Moreover, the hydrogen spectrum and HSQC spectrum show that the compound contains 18 related proton hydrogen signals, which are three methyl [δ H 1.84(3H,s,H-11), 1.14(3H,s,H-12), and 1.43(3H,s,H-...

Embodiment 2

[0071] Preparation of Japopenoid A

[0072]At room temperature, 6.5kg honeysuckle (dried) was cold-soaked and percolated for 3 times with 75% ethanol, and the extracts were combined, then, the solvent was recovered under reduced pressure at 55°C, and concentrated to obtain 1500g of ethanol extract ; The ethanol extract is suspended in 3.5L water, then extracted three times with equal volumes of cyclohexane, ethyl acetate, n-butanol successively, respectively collect each extract and concentrate to obtain 130.3g cyclohexane respectively Alkane extract, 93.7g ethyl acetate extract and 199.8g n-butanol extract; get 83.0g of said ethyl acetate extract, dissolve with chloroform and methanol (10:1, 500ml), weigh 120g column chromatography Silica gel (100-200 mesh) is mixed sample, and another 1500g column chromatography silica gel (100-200 mesh) is weighed, and this silica gel is dissolved with dichloromethane and packed column, and equilibrate column with dichloromethane until the ...

Embodiment 3

[0078] Anti-tumor activity of Japopenoid A in vitro

[0079] The inventors also investigated the antitumor activity of the monoterpene compound Japopenoid A in vitro, and the tumor strains used in related experiments were liver cancer HepG2 cells and SMCC 7721 cells.

[0080] Specifically implement the MTT method: inoculate the cells in a 96-well cell culture plate, 200 μL per well (containing 2.5×10 4 tumor cells), at 37°C, 5% CO 2 In the incubator, and in the RPMI1640 medium containing 10%FBS, culture 24h; Add the monoterpenoid Japopenoid A of different concentration (200,100,50,25,12.5 and 6.25), continue to cultivate 48h; Add 20 μL of MTT (5 mg / mL) for 4 hours, and continue to store at 37 ° C, 5% CO 2 Incubate under the conditions for 4 hours, absorb the culture solution and add 150 μL of dimethyl sulfoxide, shake until the crystals are completely dissolved, and then detect the absorbance in a microplate reader, the detection wavelength is 570nm, the reference wavelength...

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Abstract

The invention belongs to the technical field of natural medicinal chemistry, and specifically relates to a monoterpene compound. The monoterpene compound has a structural formula which is described inthe specification. The invention also relates to an extraction method for the monoterpene compound and an application of the monoterpene compound in preparation of liver cancer treatment drugs and anti-HBV drugs, and provides a pharmaceutical preparation. The extraction method for the monoterpene compound namely Japopenoid A has simple steps and easy operation; the monoterpene compound namely theJapopenoid A has less toxic and side effects, shows excellent anti-hepatoma effect and significant anti-HBV effect, and can provide a novel treatment drug and a treatment route for liver cancer and hepatitis B patients. Thus, the monoterpene compound namely the Japopenoid A and the pharmaceutical preparation containing the monoterpene compound namely the Japopenoid A provided by the invention have broad clinical application prospects, and can be developed into novel anti-hepatoma drugs or / and anti-HBV drugs in the market in the future.

Description

technical field [0001] The present invention belongs to the technical field of natural medicinal chemistry, and in particular relates to a monoterpene compound, a method for extracting the monoterpene compound, and an extraction method of the monoterpene compound in the preparation of a drug for treating liver cancer and an anti-hepatitis B virus drug. application, and a pharmaceutical preparation is provided. Background technique [0002] As we all know, liver disease is a major disease that endangers human health. Liver fibrosis and cirrhosis are common chronic liver diseases in Asia, and studies have shown that 90% of cirrhosis can transform into liver cancer. [0003] Hepatocellular carcinoma (HCC) is a malignant tumor that originates in liver cells, and its average survival time is 6-16 months, seriously endangering human life and health. According to statistics, about 782,000 people around the world suffer from liver cancer every year, ranking fifth and seventh in ma...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/08A61K31/357A61P35/00A61P31/20
CPCA61K31/357A61P31/20A61P35/00C07D493/08
Inventor 曾小斌葛岚岚万浩强肖凌云李洁媚吴伟刚周伯平吴诗品
Owner SHENZHEN PEOPLES HOSPITAL
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