Flavonoid compound with antioxidation activity, and preparation method and application thereof

A technology of flavonoids and flavonoids, applied in the field of tobacco chemistry, can solve problems such as applications that have not yet been seen, and achieve the effects of simple extraction process, low cost of raw material sources, and good free radical scavenging activity.

Active Publication Date: 2018-03-06
CHINA TOBACCO YUNNAN IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The present invention separates a flavonoid compound with good antioxidant activity from tobacco planting waste (tobacco rhizome), and no related reports have been seen on the compound and its application in inhibiting the oxidative deterioration of spices

Method used

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  • Flavonoid compound with antioxidation activity, and preparation method and application thereof
  • Flavonoid compound with antioxidation activity, and preparation method and application thereof
  • Flavonoid compound with antioxidation activity, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Tobacco rhizome samples were taken from Yuxi, Yunnan, and the variety was k326. Take 5.6 kg of dried tobacco rhizomes, coarsely crush them to 30 mesh, and extract 4 times with 70% acetone ultrasonically, each time for 60 minutes, and combine the extracts; filter the extracts, reduce Concentrate under pressure to 1 / 4 of the volume; let it stand, filter out the precipitate, and concentrate into 225g of extract; add 500g of acetone to the extract to dissolve, then add 320g of 100 mesh silica gel to mix the sample, after mixing the sample, use 200 mesh Silica gel 1.4kg column; use chloroform-acetone mixed organic solvents with volume ratios of 1:0, 9:1, 8:2, 7:3, 1:1 and 0:1 for gradient elution, and collect the gradient eluent , concentrated, monitored by TLC, combined the same parts to obtain 6 parts A-F, wherein, to the collected sample D (7:3) part 22.5g, and then 52% methanol as mobile phase, flow rate 20ml / min, The 21.2×250mm, 5μm ZorbaxPrepHT GF reverse-phase prepara...

Embodiment 2

[0041] Tobacco rhizome samples were taken in Dali, Yunnan. 6.3kg of dried tobacco rhizomes were taken, coarsely crushed to 35 mesh, ultrasonically extracted 4 times with 70% acetone, 50 minutes each time, and the extracts were combined; the extracts were filtered and concentrated under reduced pressure to volume 1 / 4 of that; let stand, filter out the precipitate, and concentrate into 185g of extract; add 420g of acetone to the extract to dissolve, then add 218g of 100 mesh silica gel to mix the sample, after mixing the sample, pack it with 1.5kg of 200 mesh silica gel Column; chloroform-acetone mixed organic solvent gradient elution with a volume ratio of 1:0, 9:1, 8:2, 7:3, 1:1 and 0:1, collecting the gradient eluate, concentrating, and TLC monitoring, merging the same parts, to obtain 6 parts A-F, wherein, to the collected sample D (7:3) part 48.6g, then use 52% methanol as mobile phase, flow rate 20ml / min, 21.2 * 250mm, The 5 μm ZorbaxPrepHT GF reverse-phase preparative col...

Embodiment 3

[0043] The structure of the flavonoids prepared in Example 1 is determined by the following method; the compound obtained is a yellow jelly, and HRESI-MS shows that its quasi-molecular ion peak is 335.0888[M+Na] + (calculated value 335.0895), combined with 1 H NMR and DEPT spectra confirmed its molecular formula as C 18 h 16 o 5 , with an unsaturation of 11. The hydroxyl (3440), carbonyl (1665) and aromatic rings (1612, 1553 and 1420cm -1 ) resonance absorption peak. The UV spectrum has maximum absorption at 210, 255, and 360nm, which also shows that there may be an aromatic ring structure in the compound. compound 1 H and 13 C NMR data (Table 1) show that it contains 18 carbons and 16 hydrogens, including a 1,2,3,4-tetrasubstituted benzene ring (C-5~C-10, H-5, H- 6), one 1,2-disubstituted benzene ring (C-1'~C-6', H-3'~H-6'), one α,β-unsaturated carbonyl (C-2~ C-4, H-3), 1 hydroxyethyl (δ C 32.8t and 63.2t, δ H 2.64(t)7.2 and 3.60(t)7.2), a methoxy group (δ C 61.2q...

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Abstract

The invention discloses a flavonoid compound with antioxidation activity, and a preparation method and application thereof. The flavonoid compound is separated from tobacco rootstock, has the molecular formula C18H16O5, and has the following structural formula: (the formula is as shown in the description); the compound is named as 2'-hydroxyl-7-(2-hydroxyethyl)-8-methoxy-flavone, and the English name is 2'-hydroxyl-7-(2-hydroxypropyl)-8-methoxy-flavone. The flavonoid compound is prepared from the tobacco rootstock serving as the raw materials through extractum extraction, silica-gel column chromatography and high performance liquid chromatography separation. The experiment result shows that the compound has high antioxidation activity and free radical scavenging activity, serves as a perfume antioxidant, can effectively inhibit oxidative deterioration of the perfume, obviously prolongs the shelf life and does not influence the smoking quality of cigarette.

Description

technical field [0001] The invention belongs to the technical field of tobacco chemistry, and in particular relates to a flavonoid compound extracted from tobacco rhizome for the first time, and the compound has good antioxidant activity. At the same time, the invention also relates to the preparation method of the compound and the application of the compound in inhibiting the oxidative deterioration of spices. 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. . 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. Tobacco rhizomes are wastes in the productio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30C07D311/40A24B15/24A24B15/40
CPCA24B15/241A24B15/403C07D311/30C07D311/40
Inventor 孔维松倪朝敏王晓辉李晶刘欣米其利李雪梅李松伊奥尔王迪李迎华许健韩莹端凯周敏胡秋芬杨光宇
Owner CHINA TOBACCO YUNNAN IND
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