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Ellagic acid compounds, preparation thereof and applications in anticancer drugs

A compound, the technology of ellagic acid, applied in the field of anticancer drugs and its preparation

Inactive Publication Date: 2008-10-22
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

After reviewing the data, there is no literature reporting that the two ellagic acid compounds 3,3'-di-O-methylellagic acid and 3,3'-di-O-methylellagic acid-4'-O-β-D-xylopyroside are used For the treatment of cancers such as liver cancer and gastric cancer

Method used

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  • Ellagic acid compounds, preparation thereof and applications in anticancer drugs
  • Ellagic acid compounds, preparation thereof and applications in anticancer drugs
  • Ellagic acid compounds, preparation thereof and applications in anticancer drugs

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Experimental program
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Effect test

Embodiment 1

[0044] The extraction and separation methods of two ellagic acid compounds 3,3'-di-O-methylellagic acid and 3,3'-di-O-methylellagic acid-4'-O-β-D-xylopyroside:

[0045] ① Jiuniuzao medicinal materials were collected from Taibai County, Shaanxi Province in October 2005. After natural air-drying, they were crushed. Soak 9kg of crushed Jiuniuzao in 85% ethanol for 12h, reflux extraction 3 times, 4h each time, and combine the extracts , concentrated under reduced pressure to extract;

[0046] ② Add an appropriate amount of water to the extract, then extract with petroleum ether, chloroform, and ethyl acetate, and recover the solvent to obtain 20g, 89g, and 170g of petroleum ether, chloroform, and ethyl acetate respectively;

[0047] ③The chloroform part is subjected to silica gel column chromatography, first use petroleum ether-ethyl acetate and then use chloroform-methanol as the eluent to carry out gradient elution, and collect 150ml of each part of the eluent in equal amounts, ...

Embodiment 2

[0050] Structural identification of two ellagic acid compounds 3,3'-di-O-methylellagic acid and 3,3'-di-O-methylellagic acid-4'-O-β-D-xylopyroside

[0051] The crystals precipitated in the eluent during partial column chromatography of ethyl acetate are light yellow powder crystals with a melting point of 332-334°C, MS showing a molecular weight of 344, and a molecular formula of C 16 h 10 o 8 . pass 1 H-NMR and 13 C-NMR spectrum (see attached figure 1 And attached figure 2 ) hints that it is an ellagic acid substance, and its chemical structural formula is as follows:

[0052]

[0053] 3,3'-di-O-methylellagic acid

[0054] attached figure 1 1 The spectral data and attribution in the H-NMR spectrum are as follows:

[0055] 1 H-NMR (DMSO-d 6 )δppm: 4.05 (6H, s, 2×OCH 3 ), 7.54 (2H, s, H-5, H-5'), 10.79 (2H, s, OH-4, OH-4').

[0056] attached figure 2 13 C-NMR spectrum spectrum data and attribution are as follows:

[0057] 13 C-NMR (DMSO-d 6 )δppm: 111.46...

Embodiment 3

[0070] Anti-liver cancer effects of 3,3'-di-O-methylellagic acid and 3,3'-di-O-methylellagic acid-4'-O-β-D-xylopyroside

[0071] 1. Cell Culture and Monomer Compounds

[0072] The human liver cancer cell line SMMC-7721 was provided by the Medical Research and Experimental Center of Xi'an Jiaotong University. The cells were cultured in RPMI-1640 medium containing 10% calf serum at 37°C and 5% CO 2 In a saturated humidity incubator, every 2 to 3 days when the cells were confluent, they were digested and passaged with 0.25% trypsin, and the cells in the logarithmic growth phase were used for the experiment. The two monomer compounds are 3,3'-di-O-methylellagic acid and 3,3'-di-O-methylellagic acid-4'-O-β- D-xylopyroside.

[0073] 2. Test method

[0074] Determination of ellagic acid substances 3,3'-di-O-methylellagic acid and 3,3'-di-O-methylellagic acid-4'-O-β-D-xylopyroside in Jiuniuzao by MTT method (with DMSO Dissolution) inhibited the growth of liver cancer cells.

[00...

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Abstract

The invention discloses an ellagic acid compound, the preparation thereof and applications in anticancer drugs. The ellagic acid compound is an anticancer monomer compound obtained by extracting and separating from hylonoma euphorbia root (the root and the aerial part of the euphorbia hylonoma which belongs to euphorbia). The preparation method thereof is as follows: firstly, ethanol is used for extracting the crushed air dried hylonoma euphorbia root, and obtaining extractum by concentration; secondly, chloroform and ethyl acetate are used for extracting, passing a chromatography respectively, and an eluent is used for eluting to obtain two ellagic acid compounds. The two ellagic acid compounds can inhibit the growth of human hepatoma cells and gastric cancer cells obviously by anticancer pharmacological experiments, and have the advantages of the wide anticancer spectrum, the strong antitumor activity, etc., thus being capable of being used for preparing anti-hepatoma or anti-gastric cancer drugs after combined with the carriers and excipients accepted in pharmacy.

Description

technical field [0001] The present invention relates to an anticancer drug and its preparation method, in particular to two kinds of ellagic acid compounds with anticancer activity extracted and separated from Jiuniuzao as raw material, its preparation method and its application in anticancer drugs . Background technique [0002] Cancer is a formidable enemy that endangers human health. There are about 1.6 million new cancer cases in my country every year, and about 1.3 million people die from cancer every year. The number of deaths from cancer in the country is increasing year by year. my country is a high-incidence area for liver cancer, gastric cancer, lung cancer, breast cancer and other cancers. Cancer The death rate remained high. Cancer has caused wounds that are difficult to repair and heal both physically and mentally. [0003] At present, there is no effective drug that can cure most cancer patients. Although chemotherapy drugs have a certain effect on cancer, th...

Claims

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Application Information

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IPC IPC(8): C07D493/16C07H17/04A61K31/366A61K36/47A61K31/7048A61P35/00
Inventor 郭增军谭林徐颖卜筱茜
Owner XI AN JIAOTONG UNIV
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