CN102532075B - Aurone compounds in nicotiana tabacum and application thereof - Google Patents
Aurone compounds in nicotiana tabacum and application thereof Download PDFInfo
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- CN102532075B CN102532075B CN201210000682.7A CN201210000682A CN102532075B CN 102532075 B CN102532075 B CN 102532075B CN 201210000682 A CN201210000682 A CN 201210000682A CN 102532075 B CN102532075 B CN 102532075B
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- aurone
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- mosaic virus
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- nicotiana tabacum
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Abstract
The invention belongs to the field of chemical research on tabacum, and more particularly relates to aurone compounds and the application thereof for controlling tobacco mosaic virus, wherein the aurone compounds are obtained and separated from nicotiana tabacum. The aurone compounds take nicotiana tabacum (Nicotiana tabacum L) plants which grow fast and achieve high disease resisting capability as raw material, the compounds can be obtained through extraction and separation, and the structural formula of the compounds is shown in the patent application. The aurone compounds and the application thereof have the advantages of no environmental pollution, low cost, excellent tobacco mosaic virus resisting effect and the like, and are safe to people and animals, and the raw materials are obtained easily; and the aurone compounds can be used as novel plant virus control agents for tobacco mosaic virus.
Description
Technical field
The present invention relates to the application of a kind of aurone class new compound and resisting tobacco mosaic virus thereof, belong to tobacco chemistry and agent for preventing and treating plant virus technical field.
Background technology
Tobacco mosaic virus (TMV) (Tobacco mosaic virus TMV) is the prototypical member of Tobamovirus virus, its host range is very extensive, can infect Solanaceae, Chenopodiaceae, Amaranthaceae, Curcurbitaceae, Cruciferae, Aizoaceae, pulse family and Phytolaccaceae Deng Gong 30 section's 300 various plants.Tobacco mosaic virus (TMV) is one of important disease of universal tobacco, tobacco mosaic disease can by tobacco mosaic virus (TMV) (TMV), cucumber mosaic virus (CMV) and marmor upsilon (PVY) separately or Combined Infection cause.Tobacco whole breeding time all can be susceptible, the cigarette seedling plant that is injured stunts, leaf malformation, leaf look irregular, dark green, the light green or yellowish green alternate tender leaf morbidity that zyklopisch floral leaf newly grows that is, show at first vein slight move back green, the slightly upper volume in edge, tender leaf grow up after blade face uneven, mesophyll thickness differs, leaf malformation distortion.Tobacco mosaic virus (TMV) has hindered the further raising of tobacco production and quality, very big to tobacco disserve to produce, cause disease leaf flue-cured tobacco after irregular colour even, smoke is poor, quality reduces, and lost units is generally 20%-30%, and seedling stage, the part field of morbidity caused the tobacco of having no harvest.
Along with the pay attention to day by day of people to problems such as ecology, health and safeties, the use aborning of the means such as chemical pesticide, transgenosis is just being restricted, so people have turned to antiviral natural Study on product direction the control of the viroses of plant.Therefore, utilize the meta-bolites of tobacco itself to prevent and treat tobacco mosaic virus (TMV) advantage very obvious.Because the meta-bolites of tobacco itself is to person poultry safety, non-environmental-pollution, is difficult for killed natural enemies and beneficial organism, is conducive to the eubiosis.Raw materials for production and effective constituent belong to natural product, can guarantee naturally produced Sustainable development.Therefore utilize the meta-bolites of tobacco itself to prepare the approach that resisting tobacco mosaic virus control agent is a worth exploration.
Summary of the invention
The object of the invention is from Turkish tobaccos (Nicotiana tabacum), to extract the strong compound of activity of resisting tobacco mosaic virus, and this compound is used for preventing and treating tobacco mosaic virus (TMV).
Realizing the technical scheme that above-mentioned purpose of the present invention takes is: the plant of Turkish tobaccos of take is raw material, obtains compound 4 '-hydroxyl-5 through extracting separation, 6-dimethoxy aurone, and this structural formula of compound is:
Described compound is with 90% methanol aqueous solution, at room temperature condition, to extract from the plant of the Turkish tobaccos (Nicotiana tabacum L) that screening is grown soon, resistance against diseases is strong, by silica gel column chromatography and preparation HPLC purifying, obtain successively, its molecular formula is C again
21h
18o
6na, molecular weight is 321.0732.
Described aurone compounds can be applicable to prevent and treat the tobacco mosaic virus (TMV) in tobacco growing process.
The process that the present invention extracts separated described aurone class new compound is: 2.0 kilograms are pulverized through air dried spices tobacco stem and root, with the methanol aqueous solution of 90% (3 * 3.0L), extract at ambient temperature and filter, after filtrate evaporation under reduced pressure is concentrated, again successively by silica gel (chloroform/methanol) elution chromatography and preparation HPLC purifying (methanol/water, acetonitrile/water wash-out), obtain aurone compounds of the present invention, this compound is through NMR (Nuclear Magnetic Resonance) spectrum (comprising two-dimensional spectrum), mass spectrum, infrared spectra and UV spectrum are defined as the compound of aurone class formation novelty, called after 4 '-hydroxyl-5, 6-dimethoxy aurone, the structural formula of this compound is as follows:
The physico-chemical property of the compounds of this invention (4 '-hydroxyl-5,6-dimethoxy aurone):
Physical chemical characteristics is:
Outward appearance: orange-yellow glue;
Solvability: be dissolved in methyl alcohol, acetone, pyridine etc., be slightly soluble in hexane and water etc.;
The structure of the compounds of this invention is by proton nmr spectra, carbon spectrum, two-dimensional spectrum, and infrared spectra, UV spectrum and mass-spectrometric data are identified.(its dissolution solvent is C to proton nmr spectra and carbon spectrum data in Table 1
5d
5n, 500MHz, δ: ppm); Proton nmr spectra, carbon spectrum, hsqc spectrum, HMBC spectrum and high resolution mass spectrum figure are shown in accompanying drawing 1,2,3,4 and 5.
4 '-hydroxyl-5,6-dimethoxy aurone: yellow gluey; UV (MeOH) λ
max(log ε), 358 (3.69), 256 (3.87), 210 (4.18) nm; IR (KBr) ν
max3421,2908,1667,1610,1492,1441,1269,1143,1078,851,822,775cm
-1;
1h NMR (C
5d
5n, 500MHz) and
13c NMR (C
5d
5n, 125MHz) data are in Table 1; Positive ion mode HRESI-MS:[M+Na]
+321.0739m/z (calculate: C
21h
18o
6na, 321.0732).
Table 14 '-hydroxyl-5,6-dimethoxy aurone
1h,
13c NMR data
Experiment shows: 4 '-hydroxyl-5 of the present invention, and 6-dimethoxy aurone is in the antiviral test of half leaf method, and this compound is 20 μ gml in concentration
-1to the growth inhibition ratio of tobacco mosaic virus (TMV), be 54.8%.Ningnanmycin, the commerical prod in China as Plant diseases, is used as positive control, and the growth inhibition ratio of Ningnanmycin is 33%.Result shows, 4 '-hydroxyl-5, and 6-dimethoxy aurone has shown high activity of resisting tobacco mosaic virus.
The present invention has that environmentally safe, raw material easily obtain, cost is low, to person poultry safety, the advantage such as significantly In Vitro Anti tobacco mosaic virus (TMV) effect is good.
Accompanying drawing explanation
Fig. 1 is the proton nmr spectra (1H NMR) of the compounds of this invention;
Fig. 2 is the carbon-13 nmr spectra (13C NMR) of the compounds of this invention;
Fig. 3 is the HSQC Correlated Spectroscopy of the compounds of this invention;
Fig. 4 is the HMBC Correlated Spectroscopy of the compounds of this invention;
Fig. 5 is the high resolution mass spectrum of the compounds of this invention.
Embodiment
Embodiment 1
4 '-hydroxyl-5, the separation preparation of 6-dimethoxy aurone:
1. 2.0 kilograms are pulverized through air dried spices tobacco stem and root, with the methanol aqueous solution of 90% (3 * 3.0L), extract at ambient temperature and filter, the concentrated crude extract (152.8g) that obtains of filtrate evaporation under reduced pressure, then crude extract is carried out to silica gel chromatography separation, take chloroform/methanol as eluent gradient elution (20: 1,9: 1,8: 2,7: 3,6: 4,5: 5).
2. collect the chloroform/methanol elutriant of 9: 1, concentrating under reduced pressure.Concentrated solution is carried out to silica gel chromatography separation again, and chloroform/acetone is eluent gradient elution (10: 1,7: 3,6: 4,5: 5).
3. collect the chloroform/acetone elutriant of 7: 3, concentrating under reduced pressure.Concentrated solution is prepared to high performance liquid chromatography separation again, and methanol/water is eluent isocratic elution (32% methanol aqueous solution, flow velocity: 12mL/min).
4. being collected in ultraviolet detection wavelength is under 360nm, to have the strong elutriant absorbing, concentrating under reduced pressure.Concentrated solution is prepared to high performance liquid chromatography separation again, and acetonitrile/water is eluent isocratic elution (20% acetonitrile solution, flow velocity: 12mL/min).Obtain new compound 4 '-hydroxyl-5 of the present invention, 6-dimethoxy aurone.
Embodiment 2
4 '-hydroxyl-5, the growth inhibition ratio experiment of 6-dimethoxy aurone to tobacco mosaic virus (TMV):
1. test with medicament
By 4 '-hydroxyl-5, the DMSO that 6-dimethoxy aurone is dissolved in, preparation 20 μ gml
-1the test liquid of concentration, in this solution, the final concentration of DMSO is no more than 3%, by the DMSO dissolved aqueous solution of same concentrations in contrast.In addition, the DMSO that Ningnanmycin is dissolved in, preparation 20 μ gml
-1the test liquid of concentration is as positive control.
2. test method
Half leaf method is used in growth inhibition ratio test to tobacco mosaic virus (TMV).
3. experimental result
Experiment shows: during active compound of the present invention is tested the growth inhibition ratio of tobacco mosaic virus (TMV), and 4 '-hydroxyl-5,6-dimethoxy aurone is 20 μ gml in concentration
-1to the growth inhibition ratio of tobacco mosaic virus (TMV), being 58.4%, is 33% as the growth inhibition ratio of the Ningnanmycin of positive control, therefore, 4 '-hydroxyl-5,6-dimethoxy aurone has showed high activity of resisting tobacco mosaic virus.
Claims (3)
1. from Turkish tobaccos, extract the separated aurone compounds obtaining, it is characterized in that: the plant of Turkish tobaccos of take is raw material, obtains compound 4 '-hydroxyl-5 through extracting separation, 6-dimethoxy aurone, this structural formula of compound is:
。
2. by aurone compounds claimed in claim 1, it is characterized in that: described compound be from Turkish tobaccos (
nicotiana tabacuml) methanol aqueous solution with 90% in plant extracts at room temperature condition, then by silica gel column chromatography and preparation HPLC purifying, obtains successively.
3. the application of the aurone compounds described in a claim 1 or 2 in preventing and treating tobacco mosaic virus (TMV).
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103030615B (en) * | 2012-12-13 | 2016-01-20 | 大兴安岭林格贝寒带生物科技股份有限公司 | A kind of method utilizing superhighpressure technology to prepare aureusidin in marchantia |
| CN103012339B (en) * | 2013-01-09 | 2014-06-04 | 云南烟草科学研究院 | Aurone compound, and preparation method and application thereof |
| US10899727B2 (en) | 2016-04-11 | 2021-01-26 | Middle Tennessee State University | Therapeutic aurones |
| KR101740915B1 (en) * | 2016-05-02 | 2017-05-29 | 한림대학교 산학협력단 | Synthetic method for aurone compounds and anti-inflammatory compounds containing thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1396918A (en) * | 2000-01-28 | 2003-02-12 | 默克专利股份有限公司 | Formulation for protection against oxidative stress containging benzofuranone derivatives |
| CN101066956A (en) * | 2007-06-08 | 2007-11-07 | 浙江大学 | Polysubstituted aurone derivative and its prepn and use |
| CN101906029A (en) * | 2010-08-16 | 2010-12-08 | 山西医科大学 | Flavonoid derivative , preparation method thereof and use thereof |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1396918A (en) * | 2000-01-28 | 2003-02-12 | 默克专利股份有限公司 | Formulation for protection against oxidative stress containging benzofuranone derivatives |
| CN101066956A (en) * | 2007-06-08 | 2007-11-07 | 浙江大学 | Polysubstituted aurone derivative and its prepn and use |
| CN101906029A (en) * | 2010-08-16 | 2010-12-08 | 山西医科大学 | Flavonoid derivative , preparation method thereof and use thereof |
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