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Lignans reduction compounds and preparation method and application thereof

A technology of norlignans and compounds, which is applied in the separation/purification of carboxylic acid compounds, organic chemistry, antiviral agents, etc., can solve the problems of easy changes in the skeleton, complex and unique structures of triterpenoids, etc., and achieve novel structures, active effect

Inactive Publication Date: 2013-04-03
YUNNAN MINZU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the triterpenoids are lanosterane and cycloaltin-type, because their skeletons are easy to change, and the structure of these triterpenoids is complex and unique due to the different degrees of oxidation.

Method used

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  • Lignans reduction compounds and preparation method and application thereof
  • Lignans reduction compounds and preparation method and application thereof
  • Lignans reduction compounds and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Take 4.5 kg of branches, leaves and / or fruits of Schisandra chinensis, coarsely crush them to 40 meshes, use 70% acetone to ultrasonically extract 5 times, each time for 60 minutes, and combine the extracts; filter the extracts, and concentrate under reduced pressure to 1% of the volume. / 4; stand, filter out the precipitate, and concentrate into 523g extract a; add 784.5g water to extract a, extract 5 times with ethyl acetate equal to the volume of water, combine the extract phases, and concentrate under reduced pressure to 385g Extract b; use 2310g of 200 mesh silica gel to pack the column, add 577.5g of acetone to the extract b to dissolve, then add 385g of 100 mesh silica gel to mix the sample, and put the sample on the column after mixing; the volume ratio is 1:0, 20: 1. Gradient elution with chloroform-methanol organic solvent solution of 9:1, 8:2, 3:2, 1:1, 1:2, 0:1, collecting the gradient eluate, concentrating, monitoring by TLC, combining the same The part, ob...

Embodiment 2

[0048] Take 5 kg of branches, leaves and / or fruits of Schisandra chinensis, coarsely crush them to 20 mesh, use 100% ethanol to ultrasonically extract twice, each time for 50 minutes, and combine the extracts; filter the extracts, concentrate under reduced pressure to 1 / 2 of the volume 3. Stand still, filter out the precipitate, concentrate into 600g of extract a; add 600g of water to extract a, extract 3 times with chloroform equal to the volume of water, combine the extraction phases, concentrate under reduced pressure into 428g of extract b ; Pack the column with 160 mesh silica gel 3.42Kg, add 1284g of acetone to dissolve in the extract b, then add 80 mesh silica gel 342.4g to mix the sample, and put it on the column after mixing the sample; the volume ratio is 1:0, 20:1, 9:1, 8:2, 3:2, 1:1, 1:2, 0:1 gradient elution of n-hexane-acetone organic solvent solution, the gradient eluate was collected, concentrated, monitored by TLC, and the same part; use reversed-phase materia...

Embodiment 3

[0050] Take 6 kg of branches, leaves and / or fruits of Heqing Schisandra, coarsely crush them to 30 mesh, use 80% methanol to ultrasonically extract 4 times, each time for 30 minutes, and combine the extracts; filter the extracts, concentrate under reduced pressure to 1 / 2 of the volume 2. Stand still, filter out the precipitate, concentrate into 635g of extract a; add 1270g of water to extract a, extract 4 times with diethyl ether equal to the volume of water, combine the extraction phases, concentrate under reduced pressure into 500g of extract b ; Use 180 mesh silica gel 3.5Kg to pack the column, add 1000g of acetone to the extract b to dissolve, then add 90 mesh silica gel 600g to mix the sample, and put it on the column after mixing the sample; the volume ratio is 1:0, 20:1, 9 respectively :1, 8:2, 3:2, 1:1, 1:2, 0:1 chloroform-acetone organic solvent solution gradient elution, collect gradient eluate, concentrate, monitor by TLC, merge the same part; Pack the column with r...

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Abstract

The invention discloses lignans reduction compounds and a preparation method and application thereof. According to the structural formulas of the compounds, R1 is -OH, R2 is -H, a molecular formula is C13H18O7, and one compound is named as marphenol D; and R1 is -OCH3, R2 is -OH, a molecular formula is C14H20O8, and the other compound is named as marphenol E. According to the preparation method, the lignans reduction compounds are prepared from the raw materials including dried branches, leaves and / or fruits of schisandra chinensis. The preparation method comprises the steps of extract extraction, organic solvent extraction, silica column chromatography and high pressure liquid chromatography separation of the raw materials. The invention further discloses the application of the lignans reduction compounds to preparation of anti-AIDS medicines. According to cytotoxicity detection on C8166 host cells and inhibition tests on an HIV-1IIIB-induced cytopathic effect (CPE) of the C8166, the two fluorenone compounds, namely the marphenol D and the marphenol E, have good anti-HIV-1 activity, the EC50 values of the two fluorenone compounds are respectively 3.14 microgram / mL and 3.22 microgram / mL, and the therapeutic index (IT) values of the two fluorenone compounds are respectively 26.91 and 26.13. The fluorenone compounds have novel structures and high activity, have good prospect in preparation of the anti-AIDS medicines, and can serve as guiding compounds of the anti-AIDS medicines.

Description

Technical field [0001] The present invention is a field of active ingredient extraction technology, which involves a hypogenal compound and its preparation methods and applications. Background technique [0002] Schisandra is Schisandraceae, Gemini, and has southern Schisandra ( Kadsura ) And Schisandra ( Schisandra) There are 50 species in the two genus, which are distributed in East Asia, Southeast Asia and southern North America. They are all produced in both genus in my country, about 30 species. They are produced in the southwest and northeast.Schisandra (Schisandra ( Schisandra) There are about 25 species, and there are 19 species in my country. It is distributed from southwest to southeast. [0003] At present, the compounds separated from Schisandraceae are mainly two categories: Triterpenes class compounds and lignans.Most of the triadic compounds are wool -lampoline type and ring Alcheon type. Because their skeleton is prone to change, and due to different oxidation, th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C59/64C07C51/42A61P31/18
Inventor 高雪梅胡秋芬
Owner YUNNAN MINZU UNIV
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