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Parallel six-membered ring biphenyl compound, preparation method and application thereof

The technology of a compound, cyclobiphenyl, applied in the field of tobacco chemistry

Active Publication Date: 2015-01-07
CHINA TOBACCO YUNNAN IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The present invention has isolated a parallel six-membered ring biphenyl compound with anti-tobacco mosaic virus activity from tobacco, which has not been reported so far

Method used

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  • Parallel six-membered ring biphenyl compound, preparation method and application thereof
  • Parallel six-membered ring biphenyl compound, preparation method and application thereof
  • Parallel six-membered ring biphenyl compound, preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] ------The preparation of the compound adopts the following steps:

[0032] 1. Extraction of extract: get the whole plant of tobacco sample, tobacco can be pulverized or cut into small pieces, and use high concentration methanol (w%: 95%) or high concentration ethanol (w%: 95%) or high concentration acetone (w%: 95%) 70%) is the extraction solvent, extraction solvent: tobacco (weight ratio)=2~4:1, soak for 36h, extract 4 times, combine extract, filter and concentrate to become medicinal extract;

[0033] 2. Silica gel column chromatography: dissolve the extract with 2.5 times the weight of pure methanol or pure ethanol or pure acetone, mix the sample with 1.5 times the weight of 80-100 mesh silica gel, and use 2.5 times the weight of 160-300 Silica gel dry packing for silica gel column chromatography; chloroform-acetone with a volume ratio of (1:0, 9:1, 8:2, 7:3, 6:4, 1:1, 0:1) The solution is subjected to gradient elution, the same fractions are combined, and the eluen...

Embodiment 2

[0038]The tobacco samples were from Kunming, Yunnan, and the variety was Honghua Dajinyuan. Sampling 2.0 kg of tobacco was pulverized and extracted 5 times with 95% methanol for 24 hours each time. The extracts were combined, filtered, and concentrated under reduced pressure to form an extract to obtain 100 g of extract. After dissolving the extract with 2.0 times the amount of pure methanol by weight, mix the sample with 120g of 100-mesh silica gel, pack 0.6kg of 160-mesh silica gel into a column for silica gel column chromatography, and use a volume ratio of 1:0, 9:1, 8:2, 7:3, 6:4, 1:1, 0:1 chloroform-acetone gradient elution, TLC monitoring and merging the same parts to obtain 8 parts, in which the volume ratio is 9:1 chloroform-acetone The acetone elution part was separated by Agilent 1100 semi-preparative high-performance liquid chromatography, with 43% methanol as mobile phase, Zorbax SB-C18 (21.2×250mm, 5 μm) preparative column as stationary phase, flow rate was 20ml / m...

Embodiment 3

[0040] The tobacco sample comes from Dali, Yunnan, and the variety is K326. The tobacco sample is 4.0kg and chopped, extracted 4 times with 95% ethanol, each extraction is 48h, the extracts are combined, filtered, and concentrated under reduced pressure to obtain an extract 192g . The extract is dissolved in pure methanol with a weight ratio of 2.0 times, and then mixed with 200 g of 80 mesh thick silica gel, and 1.2 kg of 200 mesh silica gel is packed into a column for silica gel column chromatography, and the volume ratio is 1:0, 9:1, 8:2, 7:3, 6:4, 1:1, 0:1 chloroform-acetone gradient elution, TLC monitoring and merging the same parts to obtain 8 parts, in which the volume ratio is 9:1 chloroform-acetone The acetone elution part was separated by Agilent 1100 semi-preparative high-performance liquid chromatography, with 43% methanol as mobile phase, Zorbax SB-C18 (21.2×250mm, 5 μm) preparative column as stationary phase, flow rate was 20ml / min, UV The detection wavelength o...

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Abstract

The present invention discloses a parallel six-membered ring biphenyl compound (I), a preparation method and an application thereof. The preparation method is as follows: adopting tobacco whole plants as raw materials, extracting the raw materials with high-concentration methanol or high-concentration acetone / water or high-concentration ethanol / water, combining extracting solutions, carrying out filtering, concentrating the filtrate under reduced pressure to prepare an extract; loading the extract onto a column with a silica gel dry method for performing silica gel column chromatography; carrying out gradient elution with a chloroform-acetone solution, and further separating and purifying a 9:1 part of the eluent with high-pressure liquid phase chromatography to obtain the biphenyl compound. An activity test shows that the compound in the present invention has good inhibitory effects on tobacco mosaic viruses. The compound is simple in structure, has high activity, and can be taken as a pilot compound for resisting tobacco mosaic viruses.

Description

technical field [0001] The invention belongs to the technical field of tobacco chemistry, in particular to a parallel six-membered ring biphenyl compound extracted from tobacco for the first time. At the same time, the invention also relates to the preparation method and application of the compound. Background technique [0002] Tobacco is the plant with the most complex chemical composition in the world, and its secondary metabolites are very rich. After decades of research, more than 3,000 monomeric chemical substances have been identified from tobacco, and many components have not yet been identified. come out. In addition to being mainly used for smoking cigarettes, tobacco can also extract a variety of valuable chemical components from it, and discover leading compounds that are valuable for development and utilization. [0003] Biphenyls are compounds that are ubiquitous in a class of natural plants, and there are also reports of such compounds in tobacco. Biphenyls ...

Claims

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Application Information

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IPC IPC(8): C07D311/22A01P1/00
CPCC07D311/22
Inventor 尚善斋赵伟缪明明雷萍陈永宽杨光宇刘春波段沅杏张霞王岚刘志华
Owner CHINA TOBACCO YUNNAN IND
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