Phenyl propanoid derivative, preparation method thereof and application thereof to preparation of medicines resisting breast cancer

A derivative, phenylpropanoid technology, applied in the application field of phenylpropanoid derivatives and its preparation, preparation of anti-breast cancer drugs, achieving high purity, accurate results, and broad application prospects

Inactive Publication Date: 2009-09-23
SOUTH CHINA SEA INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In my country, there are very few original studies and patents of marine bioactive lead compounds in drug research. To develop marine drugs, to study the chemical components and biological activities of marine organisms such as mangrove plants, it is imminent to find lead compounds for new drugs.

Method used

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  • Phenyl propanoid derivative, preparation method thereof and application thereof to preparation of medicines resisting breast cancer
  • Phenyl propanoid derivative, preparation method thereof and application thereof to preparation of medicines resisting breast cancer

Examples

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Embodiment 1

[0032] Preparation of compounds shown in embodiment 1 formula (I) and formula (II)

[0033] In this example, the extraction, extraction, column chromatography and thin layer chromatography commonly used by those skilled in the art to obtain a certain active ingredient from plants were used to obtain two new species from the stems and branches of the mangrove plant pomegranate. substances, and carried out spectral signal analysis and identification on them, and found that the structural formulas of these two substances are shown in formula (I) and formula (II), these two compounds are a pair of epimers, belonging to phenylpropanoid compounds , but has a new skeleton structure different from existing phenylpropanoids.

[0034] The preparation method of the present embodiment, its specific steps are as follows:

[0035] (1) The stems and branches of the mangrove plant pomegranate are naturally dried and crushed, and 4.9Kg of the crushed material is taken, soaked and extracted at...

Embodiment 2

[0050] Lethal activity experiment of embodiment 2Catunaregin and Epicatunaregin to saltwater shrimp

[0051] Take a 96-well cell culture plate and add 200 μl of artificial seawater containing 10-15 sea shrimp larvae to each well to make a test culture plate.

[0052] This embodiment establishes a blank control group and a sample group: the blank control group is to add 5 μ l of solvent dimethyl sulfoxide (DMSO) to the above-mentioned test culture plate; the sample group is prepared by dissolving the obtained Catunaregin prepared in Example 1 with the solvent DMSO Catunaregin content is 500μg / mL, 50μg / mL and 5μg / mL three concentrations of sample solution, three groups of sample components, 1 group is to add 5μl concentration of 500μg / mL sample solution to the above test culture plate, 2 groups Add 5 μl of sample solution with a concentration of 50 μg / mL to the above-mentioned test culture plate, and add 5 μl of sample solution with a concentration of 5 μg / mL to the above-mentio...

Embodiment 3

[0060] Embodiment 3MTT method measures the antitumor activity of Catunaregin and Epicatunaregin

[0061] In this example, the tumor cell-human breast cancer F10 (commercially available) was selected as the research object, and the tumor cell growth inhibition experiment was carried out on Catunaregin and Epicatunaregin by using the MTT colorimetric method routinely used by those skilled in the art to detect cell survival and growth.

[0062] Sample group: Catunaregin prepared in Example 1 was dissolved in DMSO to prepare five sample groups with Catunaregin content of 0.01, 0.1, 1, 10 and 100 μg / mL.

[0063] Positive control group: 5-fluorouracil.

[0064] Negative control group: complete cell culture medium with 0.5 volume % DMSO (commercially available).

[0065] F10 cells in the logarithmic growth phase were collected and seeded in 96-well culture plates, with the number of cells per well being 1.0×10 5 / 100μl, placed in 5vol% CO 2 Culture in an incubator, remove the medi...

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Abstract

The invention discloses a phenyl propanoid derivative, a preparation method thereof and an application thereof to the preparation of medicines resisting the breast cancer. The phenyl propanoid derivative is a pair of epimers in constitutional formulas (I) and (II), is prepared by extracting mangrove plant Randia spinosa with 95 percent of industrial alcohol by combined methods of column chromatography and thin-layer chromatography, has a new skeletal structure different from the prior phenyl propanoid and has toxic action on brine shrimps and breast cancer cells of a human body, thereby being used in the fields of medicine, pharmacy, and the like as a medicine lead compound, for example, being used for preparing the medicines resisting the breast cancer.

Description

technical field [0001] The invention relates to the field of biologically active organic compounds, in particular to a phenylpropanoid derivative and its preparation method and application in the preparation of anti-breast cancer drugs. Background technique [0002] Phenylpropanoids are a class of natural ingredients containing one or several C6-C3 units. Such components exist alone or in the form of 2, 3, 4 or even multiple units, including styrene-acrylic, phenylpropanol, phenylpropionic acid and its esters, coumarin, and lignans , flavonoids and lignin etc. From the biosynthetic pathway, most phenylpropanoids are composed of shikimic acid, phenylalanine and tyrosine, and then deamination, hydroxylation, coupling and other reactions to form final products. The skeleton structures of phenylpropanoid derivatives that have been discovered so far are represented by phenylpropionic acids, coumarins, lignans and flavonoids. [0003] Many phenylpropanoid compounds have good bi...

Claims

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Application Information

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IPC IPC(8): C07D493/18A61K31/35A61P35/00
Inventor 张偲高广春尹浩漆淑华罗雄明肖志会李庆欣
Owner SOUTH CHINA SEA INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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