CN103554077A - Chromone compound as well as preparation method and application thereof - Google Patents
Chromone compound as well as preparation method and application thereof Download PDFInfo
- Publication number
- CN103554077A CN103554077A CN201310519114.2A CN201310519114A CN103554077A CN 103554077 A CN103554077 A CN 103554077A CN 201310519114 A CN201310519114 A CN 201310519114A CN 103554077 A CN103554077 A CN 103554077A
- Authority
- CN
- China
- Prior art keywords
- chromone
- preparation
- tobacco
- compound
- silica gel
- 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
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D313/08—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/22—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom rings with more than six members
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a chromone compound as well as a preparation method and application thereof. The chromone compound is obtained by separating from tobacco rootstock, the molecular formula of the chromone compound is C14H13O4 and comprises the structure as shown in the specification. The preparation method of the chromone compound comprises the following steps: on the basis of using the tobacco rootstock as a raw material, extracting extractum, and performing silica column chromatography and high pressure liquid chromatographic separation. The method comprises the following specific steps: crushing the tobacco rootstock sample, extracting ethanol ultrasonic extraction, combining extracting solution, filtering, reducing pressure, and concentrating to obtain the extractum; performing initial chromatography analysis on the extractum by using silica gel dry column-packing; performing gradient elution by using a chloroform-acetone solution in volume ratio of (1:0)-(1:2); further purifying the 8:2 part of eluate by using high pressure liquid chromatographic separation to obtain the chromone compound. The test proves that the chromone compound have good cell activity to tobacco mosaic virus. The compound disclosed by the invention is simple in structure, easy for realization of artificial synthesis and good in activity, and can be used as guiding compound for preventing the tobacco mosaic virus.
Description
Technical field
The invention belongs to tobacco chemistry field, be specifically related to a kind of chromone compounds extracting and preparation method thereof and application from tobacco rhizome.
Background technology
Tobacco be in each kind of plant of being familiar with of the mankind containing the abundantest a kind of of chemical substance, through the research of decades, people identify that monomer chemical substance out just surpasses kind more than 3000 at present from tobacco, and also have many compositions not yet to identify out.Tobacco, except being mainly used in cigarette smoking purposes, also can therefrom be extracted the multiple chemical composition that has utility value, therefrom finds that there is the guiding compound of value of exploiting and utilizing.Particularly for the root of tobacco and stem, general all as the offal treatment in leaf tobacco production process.Therefore, except as cigarette consumption, the comprehensive utilization of strengthening tobacco and waste thereof is significant.
Chromone compounds is ubiquitous compound in a class natural phant, is also the important component in tobacco, and this compounds has pharmacological action widely, as antitumor, anti-human immunodeficiency virus (HIV), anti-oxidant, antibiotic, anticoagulation etc.; Have and studies confirm that simultaneously, its pharmacological action and chemical structure are closely related, can further research and develop more chromone compounds, therefrom find effective lead compound and active group.The present invention is separated from tobacco rhizome has obtained a kind of new chromone compounds with activity of resisting tobacco mosaic virus, and this compound it is not yet seen relevant report.
Summary of the invention
The first object of the present invention is to provide a kind of chromone compounds; The second object is to provide the preparation method of this chromone compounds; The 3rd object is the application of described chromone compounds in preparing resisting tobacco mosaic disease medicine.
The first object of the present invention is achieved in that described compound is that separation obtains from tobacco rhizome, and its molecular formula is C
14h
13o
4, there is following structure:
This compound is yellow jelly, and chemical name is: tobacco chromone C (tobchromone C).
The second object of the present invention is achieved in that the preparation method of described chromone compounds take tobacco rhizome as raw material, through medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography separating step, is specially:
A, medicinal extract extract: get tobacco rhizome, be crushed to 20 ~ 40 orders, and with 90 ~ 99% ethanol ultrasonic extraction 3 ~ 5 times, each 30 ~ 60 min, united extraction liquid, filtration, concentrating under reduced pressure becomes medicinal extract;
B, silica gel column chromatography: medicinal extract carries out silica gel column chromatography with 160 ~ 200 order silica gel dry column-packings of 4 ~ 5 times of amounts; The chloroform-acetone solution that the volume proportion of take is 1:0 ~ 1:2 is carried out gradient elution, merges identical part, collects each several part elutriant concentrated;
C, high pressure liquid chromatography separation: the 8:2 part of B step elutriant further obtains described chromone compounds with high pressure liquid chromatography separation and purification.
The structure of the chromone compounds of preparing with aforesaid method is to measure out by the following method:
The compounds of this invention is yellow jelly; UV spectrum (solvent is methyl alcohol),
λ max(log ε) 210 (4.26), 253 (3.68), 292 (3.47) nm; Infrared spectra (pressing potassium bromide troche) ν
max3436,2918,2860,1705,1642,1604,1570,1465,1385,1205,1142,970,863 cm
-1; High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak 245.0819 [M-H]
-(calculated value 245.0814).In conjunction with
1h and
13c NMR spectrum provides a molecular formula C
14h
14o
4, degree of unsaturation is 8.From
1h and
13cNMR spectrum (attribution data is in Table-1) signal can be found out: in compound, have 8 aromatic series carbon (δ
c144.3 s, 111.1 d, 160.8 s, 113.5 s, 164.6 s, 114.8 d, 128.0 d, 154.1 s), 2 carbonyl carbon (δ
c193.5 s and 205.9 s), 2 methyl carbon (δ
c22.1 q and 30.5 q), 2 methyl carbon (δ
c72.0 t and 50.2 t).In its hydrogen spectrum, contain 3 groups of aromatic series hydrogen signal (δ
h6.50 (d) 1.8,6.62 (d) 1.8 and 6.29 s), 2 unimodal (δ of methyl
h2.01 s and 2.44 s), 2 unimodal (δ of methylene radical
h4.11 s and 4.42 s), 1 phenolic hydroxyl group (δ
h9.88 s).These signals show to include 1 chromone parent in compound, 1 acetonyl, and 1 phenolic hydroxyl group.From H-8 (δ
h6.29) and C-4 (δ
c113.5), C-7 (δ
c193.5), C-10 (δ
c72.0), C-11 (δ
c22.1), H-10 (δ
h4.42) and C-3 (δ
c160.8), C-8 (δ
c128.0), H-11 (δ
h2.01) and C-8 (δ
c128.0), C-9 (δ
c154.1), C-10 (δ
c72.0) HMBC relevant (accompanying drawing 3) also susceptible of proof has chromone parent to exist.From H-1 ' (δ
h4.11) and C-1 (δ
c144.3), C-2 (δ
c111.1), C-6 (δ
c114.8) the relevant susceptible of proof acetonyl of HMBC, is substituted in the C-1 position of chromone parent. in addition, from phenolic hydroxyl group signal (
δ h9.88) be substituted in C-5 position with the relevant confirmation of the HMBC phenolic hydroxyl group of C-4 (113.5), C-5 (164.6), C-6 (114.8), so far the structure of compound is confirmed.
the compound of table-1.
1
h NMR and
13
c NMR data (CDCl
3
)
| No. | δ C (m) | δ H (m, J, Hz) | No. | δ C (m) | δ H (m, J, Hz) |
| 1 | 144.3 s | ? | 9 | 154.1 s | ? |
| 2 | 111.1 d | 6.50 (d) 1.8 | 10 | 72.0 t | 4.42 s |
| 3 | 160.8 s | ? | 11 | 22.1 q | 2.01 s |
| 4 | 113.5 s | ? | 1' | 50.2 t | 4.11 s |
| 5 | 164.6 s | ? | 2' | 205.9 s | ? |
| 6 | 114.8 d | 6.62 (d) 1.8 | 3' | 30.5 q | 2.44 s |
| 7 | 193.5 s | ? | 5-OH | ? | 9.88 s |
| 8 | 128.0 d | 6.29 s | ? | ? | ? |
The 3rd object of the present invention is achieved in that being about to described chromone compounds is applied to the preparation in tobacco mosaic disease medicine.
Chromone compounds of the present invention is separated first, has determined for chromone compounds, and characterized 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 25.2%, has good activity of resisting tobacco mosaic virus, and its activity approaches the relative inhibition (28.7%) of reference substance Nanning mycin.Above result has disclosed compound of the present invention good application prospect in preparing resisting tobacco mosaic virus medicine.The compounds of this invention activity simple in structure is good, can be used as the guiding compound of resisting tobacco mosaic virus medicine.
Accompanying drawing explanation
Fig. 1 is the carbon-13 nmr spectra of compound;
Fig. 2 is the proton nmr spectra of compound;
Fig. 3 is that the main HMBC of compound is relevant.
Embodiment
Below in conjunction with embodiment and accompanying drawing, the present invention is further illustrated, but never in any form the present invention is limited, and any conversion or the improvement based on training centre of the present invention, done, all fall into protection scope of the present invention.
* except as otherwise noted, the percentage ratio adopting in the present invention is mass percent.
Chromone compounds C of the present invention
14h
13o
4preparation method comprise medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography separating step, specifically comprise:
A, medicinal extract extract: get tobacco rhizome, be crushed to 20 ~ 40 orders, and with 90 ~ 99% ethanol ultrasonic extraction 3 ~ 5 times, each 30 ~ 60 min, united extraction liquid, filtration, concentrating under reduced pressure becomes medicinal extract;
B, silica gel column chromatography: medicinal extract carries out silica gel column chromatography with 160 ~ 200 order silica gel dry column-packings of 4 ~ 5 times of amounts; The chloroform-acetone solution that the volume proportion of take is 1:0 ~ 1:2 is carried out gradient elution, merges identical part, collects each several part elutriant concentrated;
C, high pressure liquid chromatography separation: the 8:2 part of B step elutriant further obtains described chromone compounds with high pressure liquid chromatography separation and purification.
The etoh solvent concentration of described A step is 95%.
The medicinal extract of described B step is before silica gel column chromatography rough segmentation, with after the pure dissolve with methanol of 1.5 ~ 3 times of amounts of weight ratio with 80 ~ 100 order silica gel mixed samples with 1.5 ~ 2.5 times.
The chloroform-acetone solution volume proportion of described B step is 1:0,20:1,9:1,8:2,7:3,6:4,1:1,1:2.
High performance liquid chromatography separation and purification in described C step is to adopt 21.2 mm * 250 mm, the C of 5 μ m
18chromatographic column, flow velocity is 20 mL/min, the methyl alcohol that moving phase is 50%, it is 254 nm that UV-detector detects wavelength, each sample introduction 200 μ L collect the chromatographic peak of 18.6 min, repeatedly cumulative after evaporate to dryness.
Material after the separation and purification of described C step mesohigh liquid phase chromatography is used pure dissolve with methanol again, then take pure methyl alcohol as moving phase, separated with gel filtration chromatography, with further separation and purification.
The application of chromone compounds of the present invention in preparing resisting tobacco mosaic virus medicine.
Raw materials used area and the kind of not being subject to of the present invention limits, and all can realize the present invention, and to derive from the tobacco rhizome sample of Yunnan Yuxi, the present invention will be further described below:
embodiment 1
Tobacco rhizome sample source is in Yunnan Yuxi, and kind is cloud and mist-85.Tobacco rhizome is sampled to 2.2 kg and be crushed to 30 orders, 30 min are extracted in supersound extraction 3 times of the ethanol with 95% at every turn, and extracting solution merges, and filters, and concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 105.4 g.Medicinal extract with after the pure dissolve with methanol of weight ratio 1.5 times of amounts with the thick silica gel mixed sample of 100 order of 160 g, the 160 order silica gel dress posts of 1.0 kg carry out silica gel column chromatography, with volume proportion, be 1:0, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone gradient elution of 1:2, TLC monitoring merges identical part, obtain 8 parts, chloroform-acetone wash-out that wherein volume proportion is 8:2 is partly separated with prompt logical sequence 1,100 half preparative high-performance liquid chromatographics of peace, 50% the methyl alcohol of take is moving phase, Zorbax SB-C18 (21.2 * 250 mm, 5 μ m) preparative column is stationary phase, flow velocity is 20 ml/min, it is 254 nm that UV-detector detects wavelength, each sample introduction 200 μ L, collect the chromatographic peak of 18.6 min, evaporate to dryness after repeatedly adding up, products therefrom is used pure dissolve with methanol again, then take pure methyl alcohol as moving phase, separated with Sephadex LH-20 gel filtration chromatography, obtains this new compound.
embodiment 2
Tobacco rhizome sample source is in Yunnan Yuxi, and kind is cloud and mist-85.Tobacco rhizome is sampled to 3.5 kg and be crushed to 40 orders, 45 min are extracted in supersound extraction 5 times of the ethanol with 90% at every turn, and extracting solution merges, and filters, and concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 215 g.Medicinal extract with after the pure dissolve with methanol of weight ratio 3 times of amounts with the thick silica gel mixed sample of 80 order of 350 g, the 200 order silica gel dress posts of 1.5 kg carry out silica gel column chromatography, with volume proportion, be 1:0, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone gradient elution of 1:2, TLC monitoring merges identical part, obtain 8 parts, chloroform-acetone wash-out that wherein volume proportion is 8:2 is partly separated with prompt logical sequence 1,100 half preparative high-performance liquid chromatographics of peace, 50% the methyl alcohol of take is moving phase, Zorbax SB-C18 (21.2 * 250 mm, 5 μ m) preparative column is stationary phase, flow velocity is 20 ml/min, it is 254nm that UV-detector detects wavelength, each sample introduction 200 μ L, collect the chromatographic peak of 18.6 min, evaporate to dryness after repeatedly adding up, products therefrom is used pure dissolve with methanol again, then take pure methyl alcohol as moving phase, separated with Sephadex LH-20 gel filtration chromatography, obtains this new compound.
embodiment 3
Tobacco rhizome sample source is in Yunnan Yuxi, and kind is cloud and mist-85.Tobacco rhizome is sampled to 5 kg and be crushed to 60 orders, 60 min are extracted in supersound extraction 3 times of the ethanol with 99% at every turn, and extracting solution merges, and filters, and concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 312 g.Medicinal extract with after the pure dissolve with methanol of weight ratio 1.6 times of amounts with the thick silica gel mixed sample of 90 order of 500 g, the 180 order silica gel dress posts of 1.8 kg carry out silica gel column chromatography, with volume proportion, be 1:0, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone gradient elution of 1:2, TLC monitoring merges identical part, obtain 8 parts, chloroform-acetone wash-out that wherein volume proportion is 8:2 is partly separated with prompt logical sequence 1,100 half preparative high-performance liquid chromatographics of peace, 50% the methyl alcohol of take is moving phase, Zorbax SB-C18 (21.2 * 250 mm, 5 μ m) preparative column is stationary phase, flow velocity is 20 ml/min, it is 254 nm that UV-detector detects wavelength, each sample introduction 200 μ L, collect the chromatographic peak of 18.6 min, evaporate to dryness after repeatedly adding up, products therefrom is used pure dissolve with methanol again, then take pure methyl alcohol as moving phase, separated with Sephadex LH-20 gel filtration chromatography, obtains this new compound.
embodiment 4
The compound of getting embodiment 1 preparation is yellow jelly.
Measuring method is: with nucleus magnetic resonance, in conjunction with other spectroscopic technique, identify structure.
1) UV spectrum (solvent is methyl alcohol), λ max (log ε) 210 (4.26), 253 (3.68), 292 (3.47) nm;
2) infrared spectra (pressing potassium bromide troche) ν max 3436,2918,2860,1705,1642,1604,1570,1465,1385,1205,1142,970,863 cm-1;
3) high resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak 245.0819 [M-H]
-(calculated value 245.0814).In conjunction with
1h and
13c NMR spectrum provides a molecular formula C
14h
14o
4, degree of unsaturation is 8.
From
1h and
13cNMR spectrum (attribution data is in Table-1) signal can be found out: in compound, have 8 aromatic series carbon (δ
c144.3 s, 111.1 d, 160.8 s, 113.5 s, 164.6 s, 114.8 d, 128.0 d, 154.1 s), 2 carbonyl carbon (δ
c193.5 s and 205.9 s), 2 methyl carbon (δ
c22.1 q and 30.5 q), 2 methyl carbon (δ
c72.0 t and 50.2 t).In its hydrogen spectrum, contain 3 groups of aromatic series hydrogen signal (δ
h6.50 (d) 1.8,6.62 (d) 1.8 and 6.29 s), 2 unimodal (δ of methyl
h2.01 s and 2.44 s), 2 unimodal (δ of methylene radical
h4.11 s and 4.42 s), 1 phenolic hydroxyl group (δ
h9.88 s).These signals show to include 1 chromone parent in compound, 1 acetonyl, and 1 phenolic hydroxyl group.From H-8 (δ
h6.29) and C-4 (δ
c113.5), C-7 (δ
c193.5), C-10 (δ
c72.0), C-11 (δ
c22.1), H-10 (δ
h4.42) and C-3 (δ
c160.8), C-8 (δ
c128.0), H-11 (δ
h2.01) and C-8 (δ
c128.0), C-9 (δ
c154.1), C-10 (δ
c72.0) HMBC relevant (accompanying drawing 3) also susceptible of proof has chromone parent to exist.From H-1 ' (δ
h4.11) and C-1 (δ
c144.3), C-2 (δ
c111.1), C-6 (δ
c114.8) the relevant susceptible of proof acetonyl of HMBC, is substituted in the C-1 position of chromone parent. in addition, from phenolic hydroxyl group signal (
δ h9.88) be substituted in C-5 position with the relevant confirmation of the HMBC phenolic hydroxyl group of C-4 (113.5), C-5 (164.6), C-6 (114.8), so far the structure of compound is confirmed.
embodiment 5
The compound of getting embodiment 2 preparations is yellow jelly.Measuring method is identical with embodiment 4, confirms that the compound of embodiment 2 preparations is described chromone compounds---tobacco chromone C.
embodiment 6
The compound of getting embodiment 3 preparations is yellow jelly.Measuring method is identical with embodiment 4, confirms that the compound of embodiment 3 preparations is described chromone compounds---tobacco chromone C.
embodiment 7
Arbitrary chromone compounds of getting embodiment 1 ~ 3 preparation 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 50 mg/L, the compounds of this invention is carried out to activity of resisting tobacco mosaic virus mensuration.5～6 age flue-cured tobacco plant on, choose be applicable to test blade (leaf is capable normal, anosis without worm), first blade is evenly sprinkled to fine emery powder, with writing brush by standby tobacco mosaic virus (TMV) source (3.0 * 10
-3) be evenly put on the blade sprinkled with silicon carbide, after the blade of all middle choosings connects poison and finishes, be placed on immediately and in the culture dish that fills liquid, process 20 min, take out, spill the globule and about liquid on defoliation sheet, two and half leaves are restored and to be emitted on the enamel son of an influential official that is covered with toilet paper moisturizing and to add cover glass, temperature control (23 ± 2) ℃, be placed on greenhouse natural light irradiation, within 2～3 days, be visible withered spot. each is processed and establishes second half leaf for contrast, be provided with in addition 1 group be commodity Ningnanmycin processing as a comparison, press formula and calculate relative inhibition.
XI％=(CK-T)／CK×100％
X: relative inhibition (%), CK: be soaked in the withered spot number (individual) that half sheet in clear water connects malicious leaf, T is soaked in the withered spot number (individual) that half sheet in liquid connects malicious leaf.
The relative inhibition of bright compound of result is 25.2%, and the relative inhibition 28.7% of contrast Ningnanmycin is approaching, illustrates that compound has good activity of resisting tobacco mosaic virus.
Claims (8)
1. a chromone compounds, is characterized in that described compound is that separation obtains from tobacco rhizome, and its molecular formula is C
14h
13o
4,, there is following structure:
2. a preparation method for chromone compounds claimed in claim 1, is characterized in that take that tobacco rhizome is as raw material, through medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography separating step, is specially:
A, medicinal extract extract: get tobacco rhizome, be crushed to 20 ~ 40 orders, and with 90 ~ 99% ethanol ultrasonic extraction 3 ~ 5 times, each 30 ~ 60 min, united extraction liquid, filtration, concentrating under reduced pressure becomes medicinal extract;
B, silica gel column chromatography: medicinal extract carries out silica gel column chromatography with 160 ~ 200 order silica gel dry column-packings of 4 ~ 5 times of amounts; The chloroform-acetone solution that the volume proportion of take is 1:0 ~ 1:2 is carried out gradient elution, merges identical part, collects each several part elutriant concentrated;
C, high pressure liquid chromatography separation: the 8:2 part of B step elutriant further obtains described chromone compounds with high pressure liquid chromatography separation and purification.
3. the preparation method of chromone compounds as claimed in claim 2, is characterized in that the alcohol concn in described A step is 95%.
4. the preparation method of chromone compounds as claimed in claim 2, is characterized in that in described B step that medicinal extract is before silica gel column chromatography rough segmentation, with after the pure dissolve with methanol of 1.5 ~ 3 times of amounts of weight ratio by weight ratio 80 ~ 100 order silica gel mixed samples with 1.5 ~ 2.5 times.
5. the preparation method of chromone compounds as claimed in claim 2, is characterized in that the chloroform-acetone solution volume proportion in described B step is 1:0,20:1,9:1,8:2,7:3,6:4,1:1,1:2.
6. the preparation method of chromone compounds as claimed in claim 2, is characterized in that the separation and purification of described C step mesohigh liquid phase chromatography is to adopt 21.2 mm * 250 mm, the C of 5 μ m
18chromatographic column, flow velocity is 20 mL/min, the methyl alcohol that moving phase is 50%, it is 254 nm that UV-detector detects wavelength, each sample introduction 200 μ L collect the chromatographic peak of 18.6 min, repeatedly cumulative after evaporate to dryness.
7. the preparation method of chromone compounds as claimed in claim 2, it is characterized in that the material after the separation and purification of described C step mesohigh liquid phase chromatography uses pure dissolve with methanol again, take pure methyl alcohol as moving phase again, separated with gel filtration chromatography, with further separation and purification.
8. a chromone compounds claimed in claim 1 application in preparing resisting tobacco mosaic virus medicine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310519114.2A CN103554077B (en) | 2013-10-29 | 2013-10-29 | Chromone compound as well as preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310519114.2A CN103554077B (en) | 2013-10-29 | 2013-10-29 | Chromone compound as well as preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103554077A true CN103554077A (en) | 2014-02-05 |
| CN103554077B CN103554077B (en) | 2014-12-17 |
Family
ID=50008480
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310519114.2A Expired - Fee Related CN103554077B (en) | 2013-10-29 | 2013-10-29 | Chromone compound as well as preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103554077B (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104370874A (en) * | 2014-08-06 | 2015-02-25 | 云南中烟工业有限责任公司 | Combined heptatomic ring biphenyl compound preparation method and application thereof |
| CN104370726A (en) * | 2014-08-06 | 2015-02-25 | 云南中烟工业有限责任公司 | Biphenyl compound with isohesyl side chain and preparation method and application thereof |
| CN109265423A (en) * | 2018-11-20 | 2019-01-25 | 云南民族大学 | A kind of chromone compounds and its preparation method and application |
| CN109438406A (en) * | 2018-11-19 | 2019-03-08 | 云南中烟工业有限责任公司 | A kind of chromone derivative and its preparation method and application extracted from handle gland senna |
| CN109574973A (en) * | 2018-11-19 | 2019-04-05 | 云南中烟工业有限责任公司 | Chromone derivative and its preparation method and application in one seedstalk gland senna |
| CN114685524A (en) * | 2022-04-12 | 2022-07-01 | 云南中烟工业有限责任公司 | Chromone compound and preparation method and application thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4279904A (en) * | 1979-08-02 | 1981-07-21 | Kali-Chemie Pharma Gmbh | 3-Amino-1-benzoxepine derivatives and their salts and pharmaceutical compositions thereof |
| EP0198762B1 (en) * | 1985-04-11 | 1988-10-26 | Synthelabo | Dibenzo[b,e]oxepine-acetic-acid derivatives, their preparation, and pharmaceutical preparations containing them |
| EP0180890B1 (en) * | 1984-11-05 | 1989-01-04 | Kali-Chemie Pharma GmbH | Process for the diastereoselective reduction of 3-amino-1-benzoxepin-5(2h)-ones |
| CN103113342A (en) * | 2013-02-05 | 2013-05-22 | 浙江大学 | Benzo-seven-member heterocyclic compounds as well as preparation method and application thereof |
-
2013
- 2013-10-29 CN CN201310519114.2A patent/CN103554077B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4279904A (en) * | 1979-08-02 | 1981-07-21 | Kali-Chemie Pharma Gmbh | 3-Amino-1-benzoxepine derivatives and their salts and pharmaceutical compositions thereof |
| EP0180890B1 (en) * | 1984-11-05 | 1989-01-04 | Kali-Chemie Pharma GmbH | Process for the diastereoselective reduction of 3-amino-1-benzoxepin-5(2h)-ones |
| EP0198762B1 (en) * | 1985-04-11 | 1988-10-26 | Synthelabo | Dibenzo[b,e]oxepine-acetic-acid derivatives, their preparation, and pharmaceutical preparations containing them |
| CN103113342A (en) * | 2013-02-05 | 2013-05-22 | 浙江大学 | Benzo-seven-member heterocyclic compounds as well as preparation method and application thereof |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104370874A (en) * | 2014-08-06 | 2015-02-25 | 云南中烟工业有限责任公司 | Combined heptatomic ring biphenyl compound preparation method and application thereof |
| CN104370726A (en) * | 2014-08-06 | 2015-02-25 | 云南中烟工业有限责任公司 | Biphenyl compound with isohesyl side chain and preparation method and application thereof |
| CN104370726B (en) * | 2014-08-06 | 2016-02-24 | 云南中烟工业有限责任公司 | A kind of biphenyl compound with isohexyl side chain and its preparation method and application |
| CN109438406A (en) * | 2018-11-19 | 2019-03-08 | 云南中烟工业有限责任公司 | A kind of chromone derivative and its preparation method and application extracted from handle gland senna |
| CN109574973A (en) * | 2018-11-19 | 2019-04-05 | 云南中烟工业有限责任公司 | Chromone derivative and its preparation method and application in one seedstalk gland senna |
| CN109438406B (en) * | 2018-11-19 | 2021-10-22 | 云南中烟工业有限责任公司 | Chromone derivative extracted from anshansenia glauca and preparation method and application thereof |
| CN109574973B (en) * | 2018-11-19 | 2021-11-26 | 云南中烟工业有限责任公司 | Chromone derivative in anshansenna and preparation method and application thereof |
| CN109265423A (en) * | 2018-11-20 | 2019-01-25 | 云南民族大学 | A kind of chromone compounds and its preparation method and application |
| CN114685524A (en) * | 2022-04-12 | 2022-07-01 | 云南中烟工业有限责任公司 | Chromone compound and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103554077B (en) | 2014-12-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103304530B (en) | Coumarin compound and preparation method and application thereof | |
| CN103524472B (en) | Phenolic compound, and preparation method and application thereof | |
| CN103554077B (en) | Chromone compound as well as preparation method and application thereof | |
| CN102304114B (en) | Flavanone compound and application thereof | |
| CN105399656A (en) | Isobenzazole alkaloid compound, and preparation method and applications thereof | |
| CN104497000B (en) | A kind of resisting tobacco mosaic virus vegetable flavonoid and its preparation method and application | |
| CN105175239A (en) | Sesquiterpenoid compound capable of inhibiting activity of tobacco mosaic virus in tobacco, preparation method and applications thereof | |
| CN106146383B (en) | A kind of iso-indoles alkaloid compound, preparation method and application in tobacco | |
| CN104292202B (en) | A kind of flavonoid compound and its preparation method and application | |
| CN103896755B (en) | A kind of chalcone compounds preparation method | |
| CN110357894B (en) | Tricyclic alkaloid compound and preparation method and application thereof | |
| CN102351818B (en) | Coumarone phenylpropanoids compound contained in tobacco root stalk, its preparation method and its application | |
| CN104292203A (en) | Isocoumarin compound and preparation method and application thereof | |
| CN105017198B (en) | Preparation of isobutylene flavonoids in sun-cured tobacco and application of isobutylene flavonoids for resisting tobacco mosaic virus | |
| CN104387361B (en) | A kind of Isocoumarin compounds and its production and use | |
| CN103554071B (en) | Amidpulver compound and preparation method and application thereof | |
| CN103113336B (en) | Aurone compound as well as preparation method and application thereof | |
| CN113717184B (en) | Quinoline alkaloid with tobacco mosaic virus resisting activity in cigar and preparation method and application thereof | |
| CN105837412B (en) | A kind of sesquiterpenoids, its preparation method and its application in resisting tobacco mosaic virus medicine is prepared | |
| CN104650053B (en) | Flavonoids compound, as well as preparation method and applications thereof | |
| CN104262308B (en) | A kind of parallel six-ring biphenyl compound and its preparation method and application | |
| CN104370874B (en) | A kind of parallel heptatomic ring biphenyl compound and its preparation method and application | |
| CN103664862B (en) | Polyphenolic compound and its preparation method and application in a kind of Turkish tobaccos | |
| CN103922913B (en) | A kind of Chalcone Compounds and its preparation method and application | |
| CN110372707B (en) | Benzazepine alkaloid compound and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20141217 Termination date: 20161029 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |