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A kind of furan carboxylic acid compound and its preparation method and application

A technology of furocarboxylic acid and compound, which is applied in the field of tobacco chemistry and achieves the effects of good anti-tobacco mosaic virus activity, good application prospect and simple structure

Active Publication Date: 2017-09-29
YUNNAN ACAD OF TOBACCO AGRI SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The present invention has isolated a new furancarboxylic acid compound from Yunnan flue-cured tobacco leaves, which has not been reported so far. It is worth mentioning that the compound has significant anti-tobacco mosaic virus activity

Method used

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  • A kind of furan carboxylic acid compound and its preparation method and application
  • A kind of furan carboxylic acid compound and its preparation method and application
  • A kind of furan carboxylic acid compound and its preparation method and application

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preparation example Construction

[0025] The preparation method of the furancarboxylic acid compound of the present invention is to use flue-cured tobacco leaves as raw material, through extract extraction, silica gel column chromatography, high pressure liquid chromatography separation steps, specifically:

[0026] A. Extraction: Tobacco leaves are used as raw materials, crushed or cut into small pieces, soaked in 60~100% organic solvent and extracted 3~5 times, 24h~72h each time, combined extracts, filtered, concentrated under reduced pressure to obtain extracts paste;

[0027] B. Silica gel column chromatography: after the extract is dissolved in an organic solvent, mix the sample with 80-100 mesh silica gel with a weight ratio of 0.8-1.2 times the weight ratio of the extract, and then use 160-300 mesh silica gel with a weight ratio of 2-4 times the weight ratio of the extract for dry method Pack the column for silica gel column chromatography; perform gradient elution with a chloroform-acetone solution w...

Embodiment 1

[0038] The tobacco samples were from Yuxi, Yunnan, and the variety was Yuxi K326. Take 2.0 kg of tobacco leaves and pulverize them, extract 5 times with 95% methanol for 24 hours each time, combine the extracts, filter, concentrate under reduced pressure to obtain an extract, and obtain 105 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, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, 1:2 chloroform-acetone gradient elution, TLC monitoring and merging the same parts to obtain 8 parts, wherein the volume ratio is 1: The chloroform-acetone eluted part of 1 was separated by Agilent 1100 semi-preparative high-performance liquid chromatography, with 30% methanol as the mobile phase, Zorbax SB-C18 (21.2×250mm, 5μm) preparative column as the stationary phase, and the flow rate was 20ml / m...

Embodiment 2

[0040] The tobacco samples were from Dali, Yunnan, and the variety was Yunyan 200. Take 3.5 kg of tobacco leaves and chop them up, extract 4 times with 95% ethanol for 48 hours each time, combine the extracts, filter, concentrate under reduced pressure to obtain an extract, and obtain 250 g of extract. The extractant is dissolved in pure methanol with a weight ratio of 2.0 times, and then mixed with 250g of 80 mesh thick silica gel, and 1.2kg of 200 mesh silica gel is packed into a column for silica gel column chromatography, and the volume ratio is 1:0, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, 1:2 chloroform-acetone gradient elution, TLC monitoring and merging the same parts to obtain 8 parts, wherein the volume ratio is 1: The chloroform-acetone eluted part of 1 was separated by Agilent 1100 semi-preparative high-performance liquid chromatography, with 30% methanol as the mobile phase, Zorbax SB-C18 (21.2×250mm, 5μm) preparative column as the stationary phase, and the flow rate was 20...

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Abstract

The invention discloses a furan-carboxylic acid compound as well as a preparation method and application thereof; the furan-carboxylic acid compound is obtained by being separated from flue-cured tobacco leaves, has a molecular formula of C14H14O5, is named as 6-(3'-hydroxy-4'-methoxy-5'-methyl phenyl)-3-methyl-furan-2-carboxylic acid in English, and has a structure described in the specification. The preparation method of the furan-carboxylic acid compound takes the flue-cured tobacco leaves as raw materials and comprises the steps such as extract extraction, silica gel column chromatography and high-pressure liquid chromatography separation; the preparation method concretely comprises the following steps: crushing a sample, extracting, filtering, concentrating, carrying out chromatography, eluting, and purifying the 1: 1 part of eluant by the high-pressure liquid chromatography separation to obtain the furan-carboxylic acid compound. An activity test proves that the furan-carboxylic acid compound has a good inhibiting effect for tobacco mosaic virus. The furan-carboxylic acid compound is simple in structure and better in activity, and can be used as a pilot compound of a tobacco mosaic virus-resistant medicine.

Description

technical field [0001] The invention belongs to the technical field of tobacco chemistry, and in particular relates to a furancarboxylic acid compound extracted from tobacco for the first time and its preparation method and application. Background technique [0002] Tobacco is the plant with the most complex chemical composition in the world, and its secondary metabolites are very rich. According to reports by Dube and Green in 1982, more than 2,549 chemical components have been identified in tobacco. By 2008, Rodgman and perfetti reported that , the total number of compounds found in tobacco, tobacco substitutes, and cigarette smoke is approximately 8,700. At present, more than 3,000 monomeric chemical substances have been identified from tobacco, and many components have not yet been identified. 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 valuab...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/68A01N43/08A01P1/00
CPCA01N43/08C07D307/68
Inventor 吴玉萍卢秀萍孔光辉夏振远杨光宇
Owner YUNNAN ACAD OF TOBACCO AGRI SCI
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