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Lignans compounds and preparation method and application thereof

A technology of lignans and compounds, applied in the separation/purification of heterocyclic compounds, carboxylic acid compounds, organic chemistry, etc., can solve the problems of easy changes in the skeleton, complex and unique structures of triterpenoids, etc., and achieve structural Novelty and 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 compounds and preparation method and application thereof
  • Lignans compounds and preparation method and application thereof
  • Lignans compounds and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] 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

[0049] 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, and 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 extract 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 materi...

Embodiment 3

[0051] 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 compounds and a preparation method and application thereof. According to the structural formulas of the compounds, R1 is -OH, R2 is -OCH3, a molecular formula is C20H24O8, and one compound is named as marphenol E; and -OCH2O- is between R1 and R2, a molecular formula is C20H22O8, and the other compound is named as marphenol F. According to the preparation method, the lignans 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 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 E and the marphenol F, have good anti-HIV-1 activity, the EC50 values of the two fluorenone compounds are respectively 3.47 microgram / mL and 2.97 microgram / mL, and the therapeutic index (IT) values of the two fluorenone compounds are respectively 21.18 and 27.64. The fluorenone compounds have novel structures and high activity, and can serve as guiding compounds of the anti-AIDS medicines.

Description

technical field [0001] The invention belongs to the technical field of extraction of effective plant components, and in particular relates to a lignan compound and its preparation method and application. Background technique [0002] Schisandra belongs to Schisandraceae (Schisandraceae), a dicotyledonous plant, with Southern Schisandra ( Kadsura ) and Schisandra ( Schisandra) Two genera, 50 species in total, distributed in East Asia, Southeast Asia, and southern North America. Both genera are produced in my country, with about 30 species, produced in southwest to northeast, but the main production areas are southwest and south central. Schisandra ( Schisandra) There are about 25 species, including 19 species in my country, distributed from southwest to southeast. [0003] At present, the compounds isolated from Schisandraceae plants mainly fall into two categories: triterpenes and lignans. Most of the triterpenoids are lanosterane type and cycloaltin type, because the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C59/66C07C51/42C07D317/60A61K31/192A61K31/36A61P31/18
Inventor 高雪梅胡秋芬
Owner YUNNAN MINZU UNIV
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