CN105017198A - Preparation of isobutylene flavonoids in sun-cured tobacco and application of isobutylene flavonoids for resisting tobacco mosaic virus - Google Patents
Preparation of isobutylene flavonoids in sun-cured tobacco and application of isobutylene flavonoids for resisting tobacco mosaic virus Download PDFInfo
- Publication number
- CN105017198A CN105017198A CN201510381632.1A CN201510381632A CN105017198A CN 105017198 A CN105017198 A CN 105017198A CN 201510381632 A CN201510381632 A CN 201510381632A CN 105017198 A CN105017198 A CN 105017198A
- Authority
- CN
- China
- Prior art keywords
- elutriant
- tobacco
- compound
- flavonoid compound
- methanol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a flavonoid compound with a novel structure, the compound is named as 4',7-dimethoxy-6-hydroxy-8-isobutylene oxide flavones, a molecular formula is C21H20O6, and the compound has a following structure. The invention also discloses an application of the compound, the active tests show that isobutylene flavonoids has good inhibition effect. The compound has the advantages of novel structure and good antitoxic activity, and can be used for reaching the lead compound for resisting tobacco mosaic virus.
Description
Technical field
The invention belongs to technical field of phytochemistry, be specifically related to one and come from isobutenyl flavonoid compound and preparation method thereof and application in Yunnan local airing cigarette.
Background technology
Yunnan local airing cigarette is the peculiar mutation in Yunnan of tobacco, and tobacco enters Yunnan from the bright last years of a dynasty or reign in Wanli year, becomes local common farm crop to clear qianlong years.Yunnan natural condition are good, warm river valley, and the upper level cooled, mountain area all adapt to the growth of tobacco.And weather, geographical environment that Yunnan is various, tobacco defines the airing tobacco kind that a lot of have local characteristic in cultivation for many years, and wherein famous have: great river, Luoping eight cigarette, river, master of great learning and integrity five Lip river cigarette, Huize are worked in peace and contentment, and institute's cigarette, natural resources great river cigarette are newly pacified in cigarette, Mengzi, Zhao Dayao family rushes cigarette, cigarette is stepped in sky, Yunlong, Binchuan White Tower cigarette, Wei Shan south gate cigarette, Nan Jian are happy occupies cigarette, the raw cigarette of Tengchong figured woven silk material etc.These airing cigarettes often abound with in locality and do not wane; But the research of its secondary metabolite also never appeared in the newspapers.
Flavones (flavone) is the general name of flavonoid compound, makes a general reference two phenyl ring (A-and B-ring) with phenolic hydroxyl group by the interconnected a series of compounds of central thricarbon atom.Research shows, flavonoid compound has cardiovascular system activity, the antibacterial and multiple pharmacologically active such as antiviral activity, anti-tumor activity, resisting oxidation free radical activity, anti-inflammatory, analgesia, resistance state.Existing research simultaneously confirms, its pharmacological action and chemical structure closely related, in order to study the structure activity relationship of this compounds, more flavonoid compound can be researched and developed further, therefrom finding effective lead compound and active group.The present invention is separated and obtains a kind of new isobutenyl flavonoid compound from Yunnan local airing cigarette, and this compound it is not yet seen relevant report, it is worth mentioning that this compound has significant resisting tobacco mosaic disease virus activity.
Summary of the invention
A first aspect of the present invention is the isobutenyl flavonoid compound providing a kind of novel structure, and this compound is separated and obtains from Yunnan local airing cigarette, and its molecular formula is C
21h
20o
6, chemical identification by analysis, it has following structure:
This compound is safran powder, by IUPAC systematic nomenclature by its called after: 4', 7-dimethoxy-6-hydroxyl-8-isobutene oxide base flavones.
The present inventor is by its English name called after 4', 7-dimethoxy-6-hydroxy-8-[(E)-3-hydroxy-2-methylprop-1-enyl]-flavone.
A second aspect of the present invention provides the preparation method of the flavonoid compound described in above-mentioned first aspect, and the method comprises the steps:
A. prepare airing tobacco extract medicinal extract: with airing tobacco sheet for raw material, pulverized and use the first solvent soaking and extract described tobacco 2 ~ 4 times, each 12h ~ 72h, by extracting solution merging, filter and obtain described tobacco extract medicinal extract after concentrating; Wherein said first solvent is selected from the organic solvent of ethanol, methyl alcohol or acetone and the mixture of water, and wherein organic solvent accounts for the 60wt% ~ 100wt% of this first solvent, and the first solvent: tobacco=1.5 ~ 4:1, weight ratio;
B. silica gel column chromatography: by above-mentioned tobacco extract medicinal extract with being selected from pure methyl alcohol, with 60 ~ 120 order silica gel mixed samples of 1 ~ 1.6 times of weight for airing tobacco extract medicinal extract after second dissolution with solvents of straight alcohol or pure acetone, rear dry column-packing is mixed again with 160 ~ 300 order silica gel of 2 ~ 5 times of weight for airing tobacco extract medicinal extract by mixing the mixture after sample, then 10:0 is followed successively by by volume ratio, 9:1, 8:2, 7:3, a series of chloroform-methanol of 6:4 and 5:5 carry out gradient elution, the elutriant that collection obtains when being wherein the chloroform-methanol wash-out of 9:1 by volume ratio, be called the first elutriant, above-mentioned first elutriant silica gel column chromatography is continued to be separated, the a series of chloroform-acetone solution being followed successively by 15:1,12:1,10:1,8:2,7:3 and 2:1 by volume ratio carry out gradient elution, the elutriant that collection obtains when being wherein the chloroform-acetone solution wash-out of 7:3 by volume ratio, is called the second elutriant,
C. high pressure liquid chromatography is separated: above-mentioned 7:3 elution fraction is passed into high pressure liquid chromatography and carries out separation and purification, and this high pressure liquid chromatography adopts 21.2mm × 250mm, the C of 5 μm
18chromatographic column, moving phase is the methanol aqueous solution of 48wt%, flow rate of mobile phase is 12mL/min, UV-detector determined wavelength is 364nm, second elutriant liquid each sample introduction 60 ~ 150 μ L, elutriant corresponding when to collect chromatographic peak retention time after each sample introduction be 20.6min, namely obtains described flavonoid compound after solvent evaporated.
Aforementioned high pressure refers to the reversed-phase preparative chromatography making service pressure at 5-15MPa.
In preferred embodiments, the present invention also comprises the step of following further purification: the described flavonoid compound obtained after described high pressure liquid chromatography separation is dissolved in methanol solution again, and with methanol solution for moving phase, carry out chromatographic separation by gel column, mention the described flavonoid compound of purifying further.
The flavonoid compound that a third aspect of the present invention provides described in first aspect is preparing the application in resisting tobacco mosaic virus medicine.
Accompanying drawing explanation
Fig. 1 is the carbon-13 nmr spectra of novel flavonoid compound of the present invention.
Fig. 2 is the proton nmr spectra of novel flavonoid compound of the present invention.
Fig. 3 is the main HMBC relevant indicators of neoflavonoid of the present invention.
Embodiment
The structure of the novel flavonoid compound prepared by the present invention measures out by the following method: the compounds of this invention is safran powder; UV spectrum (solvent is methyl alcohol), λ
max(log ε) 210 (4.22), 254 (3.69), 364 (3.58) nm; Infrared spectra (pressing potassium bromide troche) ν
max3438,2932,2875,1652,1605,1574,1527,1462,1358,1241,1156,1038,962,826 and 768cm
-1; High resolution mass spectrum (HRESIMS) 391.1153 provides quasi-molecular ion peak m/z [M+Na]
+(calculated value 391.1158).In conjunction with
1h and
13c NMR spectrum provides molecular formula C
21h
20o
6, degree of unsaturation is 12.Nuclear magnetic resonance data (table 1) shows, this compound may be a flavonoid compound.
1h NMR and
13c NMR composes (table 1) display display 21 carbon atoms and 20 proton signals (table-1), comprise: one 1, the dibasic phenyl ring signal of 4-, one 1,2,3, the phenyl ring signal that 4,5-five replaces, an isobutenyl, two methoxyl groups, phenolic hydroxyl group, a carbonyl and one group of double bond; Wherein two benzene (C-5 ~ C-10 and C-1 ' ~ C-6 '), carbonyl (C-4) and double bonds (C-2 and C-3) constitute the skeleton of flavones.After the precursor skeleton of flavones is determined, remaining signal a: isobutenyl, two methoxyl groups, a phenolic hydroxyl group are then the substituting group of flavones.According to two methoxyl group hydrogen signals respectively (scheme-3) susceptible of proof two methoxyl group relevant to the HMBC of C-7 and C-4' be substituted in C-7 and the C-4' position of lavonoid backbone respectively, according to H-1, " susceptible of proof isobutenyl relevant with the HMBC of C-9 with C-7, C-8 is substituted in C-8 position; Relevant according to the HMBC of phenolic hydroxyl group signal and C-5, C-6 and C-7, susceptible of proof phenolic hydroxyl group signal is substituted in C-6 position.So far, the structure of compound is determined.Called after 4', 7-dimethoxy-6-hydroxyl-8-isobutene oxide base flavones (4', 7-dimethoxy-6-hydroxy-8-[(E)-3-hydroxy-2-methylprop-1-enyl]-flavone).
The nuclear magnetic resonance data of table-1 compound
The compounds of this invention is separated first, is determined as isobutenyl flavonoid compound, and characterize its concrete structure by nucleus magnetic resonance and measuring method of mass spectrum.Through the experiment to resisting tobacco mosaic virus, its relative inhibition reaches 38.6%, has good activity of resisting tobacco mosaic virus, exceedes the relative inhibition (31.5%) of positive reference substance Nanning mycin.Above result discloses compound of the present invention preparing in resisting tobacco mosaic virus medicine good application prospect.The compounds of this invention structure is simple active good, can be used as the guiding compound of resisting tobacco mosaic virus medicine.
Below in conjunction with embodiment and accompanying drawing, the present invention is further illustrated, but limited the present invention never in any form, and any conversion done based on training centre of the present invention or improvement, all fall into protection scope of the present invention.
The present invention is raw materials used not to be limited by area and kind, and the local airing cigarette in any source all can realize the present invention, and to derive from the tobacco material of cigarette industry limited liability company in Yunnan, the present invention will be further described below.Except as otherwise noted, the percentage ratio adopted in the present invention is mass percent.
Embodiment 1
Local airing cigarette used is that cigarette is stepped in sky, Yunlong, Dali.Pulverized by airing cigarette sampling 3.0kg and extract 3 times with the acetone/water of 70%, extract 24h, extracting solution merges at every turn, and filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 150g.With the thick silica gel mixed sample of 80 order of 200g after the pure dissolve with methanol of medicinal extract weight ratio 180g, the 160 order silica gel dress posts of 1.0kg carry out silica gel column chromatography, be 10:0 with volume proportion, 9:1, 8:2, 7:3, 6:4, the chloroform-methanol gradient elution of 5:5, be that the chloroform-methanol elution fraction of 9:1 carries out gradient elution by a series of chloroform-acetone solution of 15:1-2:1 further by wherein volume proportion, it is successively divided into 6 parts, wherein prompt logical sequence 1,100 half preparative high-performance liquid chromatographic of 7:3 elution fraction peace is separated, methanol aqueous solution with 48% is moving phase, Zorbax SB-C
18(21.2 × 250mm, 5 μm) preparative column is stationary phase, flow rate of mobile phase is 12ml/min, UV-detector determined wavelength is 364nm, each sample introduction 125 μ L, collecting the residence time is the chromatographic peak of 20.6min, and repeatedly cumulative rear evaporate to dryness, obtains flavonoid compound crude product of the present invention, this crude product uses pure dissolve with methanol again, with pure methyl alcohol for moving phase, can obtain sterling with dextrane gel column chromatography purification.
Embodiment 2
Airing cigarette sample source is in Dongzhou Period in Chuxiong, and for Zhao Dayao family rushes cigarette, tobacco is sampled 3.5kg chopping, the extraction using alcohol with 95% 3 times, extracts 48h at every turn, and extracting solution merges, and filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 140g.With the thick silica gel mixed sample of 80 order of 150g after the pure dissolve with methanol of medicinal extract weight ratio 2.0 times amount, the 200 order silica gel dress posts of 0.9kg carry out silica gel column chromatography, be 10:0 with volume proportion, 9:1, 8:2, 7:3, 6:4, the chloroform-methanol gradient elution of 5:5, wherein will be followed successively by 15:1 by volume ratio further with the chloroform-methanol elution fraction that volume proportion is 9:1, 12:1, 10:1, 8:2, a series of chloroform-acetone solution of 7:3 and 2:1 carry out gradient elution, the elutriant that collection obtains when being wherein the chloroform-acetone solution wash-out of 7:3 by volume ratio, and prompt logical sequence 1,100 half preparative high-performance liquid chromatographic of this 7:3 elutriant peace is separated, methanol aqueous solution with 48% is moving phase, Zorbax SB-C
18(21.2 × 250mm, 5 μm) preparative column is stationary phase, and flow rate of mobile phase is 12ml/min, UV-detector determined wavelength is 364nm, each sample introduction 100 μ L, and collecting the residence time is the chromatographic peak of 20.6min, repeatedly cumulative rear evaporate to dryness, obtains flavonoid compound of the present invention.In order to further purification, can also by products therefrom dissolve with methanol solution, then be moving phase with methanol solution, be separated with Sephadex LH-20 gel filtration chromatography, obtain this new compound more highly purified.
Embodiment 3
Compound prepared by Example 1 is safran powder.
The structure of the novel flavonoid compound prepared by the present invention measures out by the following method: the compounds of this invention is safran powder; UV spectrum (solvent is methyl alcohol), λ
max(log ε) 210 (4.22), 254 (3.69), 364 (3.58) nm; Infrared spectra (pressing potassium bromide troche) ν
max3438,2932,2875,1652,1605,1574,1527,1462,1358,1241,1156,1038,962,826 and 768cm
-1; High resolution mass spectrum (HRESIMS) 391.1153 provides quasi-molecular ion peak m/z [M+Na]
+(calculated value 391.1158).In conjunction with
1h and
13c NMR spectrum provides molecular formula C
21h
20o
6, degree of unsaturation is 12.Ultraviolet, infrared and nuclear magnetic data (table 1) show, this compound may be a flavonoid compound.
1h NMR and
13c NMR composes (table 1) display display 21 carbon atoms and 20 proton signals (table-1), comprise: one 1, the dibasic phenyl ring signal of 4-, one 1,2,3, the phenyl ring signal that 4,5-five replaces, an isobutenyl, two methoxyl groups, phenolic hydroxyl group, a carbonyl and one group of double bond; Wherein two benzene (C-5 ~ C-10 and C-1 ' ~ C-6 '), carbonyl (C-4) and double bonds (C-2 and C-3) constitute the skeleton of flavones.After the precursor skeleton of flavones is determined, remaining signal a: isobutenyl, two methoxyl groups, a phenolic hydroxyl group are then the substituting group of flavones.Be substituted in C-7 and the C-4' position of lavonoid backbone respectively according to two methoxyl group hydrogen signals relevant to the HMBC of C-7 and C-4' (scheming-3) susceptible of proof two methoxyl group, according to H-1, " susceptible of proof isobutenyl relevant with the HMBC of C-9 with C-7, C-8 is substituted in C-8 position; Relevant according to the HMBC of phenolic hydroxyl group signal and C-5, C-6 and C-7, susceptible of proof phenolic hydroxyl group signal is substituted in C-6 position.So far, the structure of compound is determined.
Embodiment 4
Compound prepared by Example 2 is safran powder.Measuring method is identical with embodiment 3, confirms that compound prepared by embodiment 2 is described flavonoid compound---4', 7-dimethoxy-6-hydroxyl-8-isobutenyl flavones.
Embodiment 5
Arbitrary biphenyl compound prepared by Example 1 ~ 3 carries out activity of resisting tobacco mosaic virus test, and test situation is as follows:
Adopt half leaf method, when the mass concentration of medicament is 50mg/L, activity of resisting tobacco mosaic virus mensuration is carried out to the compounds of this invention.5 ~ 6 age flue-cured tobacco plant on, choose the blade (leaf capable normal, anosis without worm) being applicable to test, first blade evenly sprinkled fine emery powder, with writing brush by tobacco mosaic virus (TMV) source (3.0 × 10 for subsequent use
-3) be evenly put on sprinkled with silicon carbide blade on, connect after poison terminates until the blade of all middle choosings, be placed on immediately in the culture dish filling liquid and process 20min, take out, wipe the globule and liquid on blade, being restored by two and half leaves is emitted in the glass jar being covered with toilet paper moisturizing, and cover glass cover, temperature control (23 ± 2) DEG C, be placed on greenhouse natural light irradiation, 2 ~ 3d and visible withered spot. each process set second half leaf as contrast, be provided with in addition 1 group be the process of commodity Ningnanmycin as a comparison, press formulae discovery relative inhibition.
XI％＝(CK-T)/CK×100％
X: relative inhibition (%), CK: be soaked in the withered spot number (individual) that half in clear water connects malicious leaf, T is soaked in the withered spot number (individual) that half in liquid connects malicious leaf.
The relative inhibition of result bright compound is 38.6%, exceedes the relative inhibition 31.5% of contrast Ningnanmycin, illustrates that compound has good activity of resisting tobacco mosaic virus.
Claims (5)
1. a flavonoid compound, this Compound nomenclature is 4', 7-dimethoxy-6-hydroxyl-8-isobutene oxide base flavones, and its molecular formula is C
21h
20o
6, and there is following structure:
2. a preparation method for flavonoid compound according to claim 1, it comprises the following steps:
A. prepare tobacco extract medicinal extract: be raw material with tobacco leaf, pulverized and use the first solvent soaking and extract described tobacco 2 ~ 4 times, each 12h ~ 72h, extracting solution is merged, filter and obtain described tobacco extract medicinal extract after concentrating; Wherein said first solvent is selected from the organic solvent of ethanol, methyl alcohol or acetone and the mixture of water, and wherein organic solvent accounts for the 60wt% ~ 100wt% of this first solvent, and the first solvent: tobacco=1.5 ~ 4:1, weight ratio;
B. silica gel column chromatography: by above-mentioned tobacco extract medicinal extract with being selected from pure methyl alcohol, with 60 ~ 120 order silica gel mixed samples of 1 ~ 1.6 times of weight being tobacco extract medicinal extract after second dissolution with solvents of straight alcohol or pure acetone, rear dry column-packing is mixed again with 160 ~ 300 order silica gel of 2 ~ 5 times of weight for tobacco extract medicinal extract by mixing the mixture after sample, then 10:0 is followed successively by by volume ratio, 9:1, 8:2, 7:3, a series of chloroform-methanol of 6:4 and 5:5 carry out gradient elution, the elutriant that collection obtains when being wherein the chloroform-methanol wash-out of 9:1 by volume ratio, be called the first elutriant, above-mentioned first elutriant silica gel column chromatography is continued to be separated, the a series of chloroform-acetone solution being followed successively by 15:1,12:1,10:1,8:2,7:3 and 2:1 by volume ratio carry out gradient elution, the elutriant that collection obtains when being wherein the chloroform-acetone solution wash-out of 7:3 by volume ratio, is called the second elutriant.
C. high pressure liquid chromatography is separated: above-mentioned second elutriant is passed into high pressure liquid chromatography and carries out separation and purification, and this high pressure liquid chromatography adopts 21.2mm × 250mm, the C of 5 μm
18chromatographic column, moving phase is the methanol aqueous solution of 48wt%, flow rate of mobile phase is 12mL/min, UV-detector determined wavelength is 364nm, second elutriant liquid each sample introduction 60 ~ 150 μ L, elutriant corresponding when to collect chromatographic peak retention time after each sample introduction be 20.6min, is called the 3rd elutriant, namely obtains described flavonoid compound by after the 3rd elutriant desolvation.
3. method according to claim 2, wherein said high pressure liquid chromatography refers to the reversed-phase preparative chromatography making service pressure at 5-15MPa.
4. method according to claim 2, it also comprises the step of following further purification: the described flavonoid compound obtained after described high pressure liquid chromatography separation is dissolved in methanol solution again, and with methanol solution for moving phase, carry out chromatographic separation by gel column, mention the described flavonoid compound of purifying further.
5. flavonoid compound according to claim 1 is preparing the purposes in resisting tobacco mosaic virus medicine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510381632.1A CN105017198B (en) | 2015-07-02 | 2015-07-02 | Preparation of isobutylene flavonoids in sun-cured tobacco and application of isobutylene flavonoids for resisting tobacco mosaic virus |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510381632.1A CN105017198B (en) | 2015-07-02 | 2015-07-02 | Preparation of isobutylene flavonoids in sun-cured tobacco and application of isobutylene flavonoids for resisting tobacco mosaic virus |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105017198A true CN105017198A (en) | 2015-11-04 |
| CN105017198B CN105017198B (en) | 2017-05-03 |
Family
ID=54407548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510381632.1A Active CN105017198B (en) | 2015-07-02 | 2015-07-02 | Preparation of isobutylene flavonoids in sun-cured tobacco and application of isobutylene flavonoids for resisting tobacco mosaic virus |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105017198B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107445934A (en) * | 2017-09-19 | 2017-12-08 | 玉溪师范学院 | A kind of flavone compound and its preparation method and application |
| CN107501225A (en) * | 2017-09-19 | 2017-12-22 | 玉溪师范学院 | A kind of flavone compound and its preparation method and application |
| CN107759552A (en) * | 2017-09-07 | 2018-03-06 | 云南中烟工业有限责任公司 | A kind of flavone compound with antioxidation activity and its preparation method and application |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102037963A (en) * | 2010-11-30 | 2011-05-04 | 沈阳化工大学 | Bavachalcone compounds and bavachin mixed preparation for preventing and controlling plant diseases |
| CN102304114A (en) * | 2011-08-08 | 2012-01-04 | 云南省烟草农业科学研究院 | Flavanone compound and application thereof |
| CN102870770A (en) * | 2012-09-27 | 2013-01-16 | 沈阳化工大学 | Bavachin soluble liquor and preparation method thereof |
| WO2013044061A1 (en) * | 2011-09-21 | 2013-03-28 | The Texas A&M University System | Plant viral vaccines and therapeutics |
| CN104650053A (en) * | 2015-03-09 | 2015-05-27 | 云南中烟工业有限责任公司 | Flavonoids compound with novel structure, as well as preparation method and applications thereof |
-
2015
- 2015-07-02 CN CN201510381632.1A patent/CN105017198B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102037963A (en) * | 2010-11-30 | 2011-05-04 | 沈阳化工大学 | Bavachalcone compounds and bavachin mixed preparation for preventing and controlling plant diseases |
| CN102304114A (en) * | 2011-08-08 | 2012-01-04 | 云南省烟草农业科学研究院 | Flavanone compound and application thereof |
| WO2013044061A1 (en) * | 2011-09-21 | 2013-03-28 | The Texas A&M University System | Plant viral vaccines and therapeutics |
| CN102870770A (en) * | 2012-09-27 | 2013-01-16 | 沈阳化工大学 | Bavachin soluble liquor and preparation method thereof |
| CN104650053A (en) * | 2015-03-09 | 2015-05-27 | 云南中烟工业有限责任公司 | Flavonoids compound with novel structure, as well as preparation method and applications thereof |
Non-Patent Citations (1)
| Title |
|---|
| 孔浩辉 等: "卷烟烟丝热裂解产物香味成分分析", 《烟草科技》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107759552A (en) * | 2017-09-07 | 2018-03-06 | 云南中烟工业有限责任公司 | A kind of flavone compound with antioxidation activity and its preparation method and application |
| CN107445934A (en) * | 2017-09-19 | 2017-12-08 | 玉溪师范学院 | A kind of flavone compound and its preparation method and application |
| CN107501225A (en) * | 2017-09-19 | 2017-12-22 | 玉溪师范学院 | A kind of flavone compound and its preparation method and application |
| CN107501225B (en) * | 2017-09-19 | 2020-05-19 | 玉溪师范学院 | Flavonoid compound and preparation method and application thereof |
| CN107445934B (en) * | 2017-09-19 | 2020-05-19 | 玉溪师范学院 | Flavonoid compound and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105017198B (en) | 2017-05-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105399656A (en) | Isobenzazole alkaloid compound, and preparation method and applications thereof | |
| CN103524472B (en) | Phenolic compound, and preparation method and application thereof | |
| CN105152880B (en) | Nicotiana tabacum L. sesquiterpene-F prepared by a kind of supercritical fluid chromatography and application thereof | |
| CN104945360A (en) | Preparation method and application of phenylpropanoid compound in tobacco | |
| CN103304530A (en) | Coumarin compound and preparation method and application thereof | |
| CN103554077B (en) | Chromone compound as well as preparation method and application thereof | |
| CN104387402A (en) | Isocoumarin compound and preparation method and use thereof | |
| CN105348192A (en) | Antiviral-activity isoquinoline alkaloid compound in Cassia alata L. and preparation method of antiviral-activity isoquinoline alkaloid compound | |
| CN105175239A (en) | Sesquiterpenoid compound capable of inhibiting activity of tobacco mosaic virus in tobacco, preparation method and applications thereof | |
| CN104926772B (en) | Novel flavonoid compound as well as preparation method and uses thereof | |
| CN105175240A (en) | Method for preparing novel nicotianasesterpene H having antiviral activity with supercritical fluid chromatography | |
| CN105017198A (en) | Preparation of isobutylene flavonoids in sun-cured tobacco and application of isobutylene flavonoids for resisting tobacco mosaic virus | |
| CN102786530B (en) | Plant flavanoid compound, preparation method and application thereof | |
| CN104292202B (en) | A kind of flavonoid compound and its preparation method and application | |
| CN104292203B (en) | A kind of Isocoumarin compounds and its preparation method and application | |
| CN106146383A (en) | A kind of iso-indoles alkaloid compound, its preparation method and application in Nicotiana tabacum L. | |
| CN104761525B (en) | A kind of flavone compound and preparation method and application | |
| CN104974122A (en) | Coumarin compound originated from tobacco, and preparation method and application thereof | |
| CN104387361B (en) | A kind of Isocoumarin compounds and its production and use | |
| CN103896755B (en) | A kind of chalcone compounds preparation method | |
| CN105175233B (en) | A kind of sesquiterpenoids and preparation method and application | |
| CN103113336B (en) | Aurone compound as well as preparation method and application thereof | |
| CN106008219B (en) | A kind of sesquiterpenoids, its preparation method and the application in anti-rotavirus medicaments are prepared | |
| CN104650053A (en) | Flavonoids compound with novel structure, as well as preparation method and applications thereof | |
| CN103012425B (en) | Benzofuran compound, and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |