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Isobenzofuran compound with effect of scavenging free radicals, and preparation method and application of isobenzofuran compound

A technology of benzoisofuran and compounds, applied in the field of phytochemistry, can solve problems that have not been reported in relevant literature

Active Publication Date: 2017-06-23
CHINA TOBACCO YUNNAN IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the scavenging effect of benzoisofuran compounds found in tobacco on free radicals in cigarette smoke has not been reported in the relevant literature

Method used

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  • Isobenzofuran compound with effect of scavenging free radicals, and preparation method and application of isobenzofuran compound
  • Isobenzofuran compound with effect of scavenging free radicals, and preparation method and application of isobenzofuran compound
  • Isobenzofuran compound with effect of scavenging free radicals, and preparation method and application of isobenzofuran compound

Examples

Experimental program
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Effect test

preparation example Construction

[0054] The preparation method of the benzoisofuran compounds described in the present invention is prepared by extracting the raw material of tobacco, extracting with organic solvent, decolorizing MCI, silica gel column chromatography and high performance liquid chromatography, specifically:

[0055] A. Extraction of extract: crush the tobacco to 20-40 meshes, ultrasonically extract 2-5 times with a solvent 5-10 times the weight of tobacco, 30-60 minutes each time, combine the extracts and filter, and concentrate the filtrate under reduced pressure to the original 1 / 4 of the volume, let it stand, filter out the precipitate, and then concentrate the resulting filtrate under reduced pressure into extract a;

[0056] B. Organic solvent extraction: add water with a weight 1 to 2 times the weight of the extract a to the extract a, then extract 3 to 5 times with an organic solvent equal to the volume of water, combine the organic solvent extraction phases, and then combine to obtain ...

Embodiment 1

[0067] Take 4.4 kg of dried tobacco, coarsely crush it to 30 mesh, and ultrasonically extract 4 times with 70% acetone aqueous solution 10 times the weight of the tobacco, 60 minutes each time, and combine the extracts; filter the extracts, and concentrate under reduced pressure to 1% of the original volume. / 4; leave standstill, filter out the sediment, concentrate under reduced pressure into 120g extract a;

[0068] Add 240g of water to extract a, extract 5 times with chloroform equal to the volume of water, combine the organic solvent extraction phase, and concentrate under reduced pressure to obtain 80g of extract b;

[0069] Add 240 g of methanol to the extract b to dissolve, and after the extract b is completely dissolved, put it on the MCI column, elute with 6 liters of 90% methanol aqueous solution, combine the eluents, and concentrate under reduced pressure to obtain 62 g of extract c;

[0070] Add 93g of acetone to dissolve in extract c, then add 62g of 100 mesh sili...

Embodiment 2

[0072] Take 10 kg of dried tobacco, coarsely crush it to 40 mesh, and ultrasonically extract it with methanol 5 times the weight of the tobacco for 5 times, each time for 30 minutes, and combine the extracts; filter the extracts, concentrate under reduced pressure to 1 / 4 of the original volume; place, filter the precipitate, and concentrate under reduced pressure to obtain 300g extract a;

[0073] Add 350g of water to the extract a, extract 3 times with dichloromethane equal to the volume of water, combine the organic solvent extraction phase, and concentrate under reduced pressure to 210g of extract b;

[0074] Add 630g of 50% methanol aqueous solution to the extract b to dissolve, after the extract b is completely dissolved, put it on the MCI column, elute with 10 liters of 95% methanol aqueous solution, combine the eluents, and concentrate under reduced pressure Obtain 150g extract c;

[0075]Add 300g of acetone to the extract c to dissolve, then add 180g of 80-mesh silica...

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Abstract

The invention relates to an isobenzofuran compound with an effect of scavenging free radicals, and a preparation method and an application of the isobenzofuran compound, and belongs to the technical field of phytochemistry. The isobenzofuran compound is separated from tobaccos; the compound is named 6,8-dihydro-2,2-dimethyl-2H-furan [3,4-g] chromene, the English name is 6,8-dihydro-2,2-dimethyl-2H-furo[3,4-g] chromene, the molecular formula is C13H14H2O, and the structure is as shown a formula (1) in the description. The preparation method comprises the steps: with tobaccos as the raw material, extractum extraction, organic solvent extraction, MCI decoloration, slica column chromatography and high-performance liquid chromatographic separation. Antioxidant activity and free radical-scavenging activity screening is carried out on the compound, so that the experiment result shows that the compound has relatively high antioxidant activity and free radical-scavenging activity.

Description

technical field [0001] The invention belongs to the technical field of phytochemistry, and specifically relates to a benzisofuran compound extracted from tobacco for the first time and an extraction method thereof. At the same time, the compound of the invention has good antioxidant activity and can effectively remove free radicals in cigarette smoke when used in cigarettes. Background technique [0002] Nicotiana is an annual or limited perennial herbaceous plant belonging to the family Solanaceae. Among them, N.tabacum L. is the most widely cultivated. Its mature leaves are important raw materials for the cigarette industry and a crop with high economic value. In addition to being mainly used for smoking, tobacco has other extensive uses. At the same time, tobacco is the plant with the most complex chemical composition in the world, and its secondary metabolites are very rich. After decades of research, people have identified more than 3,000 monomeric chemical substances ...

Claims

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Application Information

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IPC IPC(8): C07D493/04A24B15/24A24B15/40
CPCA24B15/241A24B15/406C07D493/04
Inventor 唐石云杨光宇申钦鹏刘春波蒋薇尤俊衡王晋刘志华何沛司晓喜李振杰朱瑞芝张凤梅王昆淼崔婷惠苏钟璧
Owner CHINA TOBACCO YUNNAN IND
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