CN109574973A - Chromone derivative and its preparation method and application in one seedstalk gland senna - Google Patents
Chromone derivative and its preparation method and application in one seedstalk gland senna Download PDFInfo
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- CN109574973A CN109574973A CN201811375708.XA CN201811375708A CN109574973A CN 109574973 A CN109574973 A CN 109574973A CN 201811375708 A CN201811375708 A CN 201811375708A CN 109574973 A CN109574973 A CN 109574973A
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- 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
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- 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
- A01N43/14—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 six-membered rings
- A01N43/16—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 six-membered rings with oxygen as the ring hetero atom
Abstract
The invention discloses the chromone derivatives and its preparation method and application in a seedstalk gland senna.The chromone derivative is isolated, the molecular formula C from handle gland senna complete stool16H16O6, Compound nomenclature are as follows: 8- hydroxyl -2- (3- hydroxypropyl) -5- (isobutyryl) -4H-4- chromone.The preparation method of the chromone derivative, be using whole strain handle gland senna plant as raw material, through crushing, extraction, silica gel column chromatography, high pressure liquid chromatography separating step and obtain.Compound of the present invention shows there is good inhibiting effect to tobacco mosaic virus (TMV) through biological activity test.The compounds of this invention can be easily separated to obtain, and compound activity is good, can be used as the guiding compound of resisting tobacco mosaic virus.
Description
Technical field
The invention belongs to technical field of phytochemistry, and in particular to a kind of to extract isolated color from handle gland senna
Ketone derivatives and its preparation method and application.
Background technique
Handle gland senna (Cassia pumila Lam.) is that pulse family (Leguminosae) Cassia (Cassia) is perennial
Suffruticose hangs down loosely draft, and bashfully Cassia occidentalis, garden burnet, dream are careless for alias, flogs ground sand, thin thick stick wood, Herba Cassiae Mimosoidis, Di Baicao, water soap
Angle, base portion lignifying is 25-75 centimetres high, multi-branched, linear crescent, and there are small spur, branch in top, and branch, petiole, rachis are dredged
Pubescence, the 8-9 month bloom；10-12 month result.Handle gland senna is born in the bushes or thick grass of mountainous region and field, state
It being inside distributed mainly on and is saved in Guangdong, Yunnan etc., external India, South East Asia Mainland, Malaysia, Australia are also distributed, as
A kind of traditional Chinese herbal medicine has clearing heat and detoxicating, invigorating spleen to remove dampness, defaecation.Main jaundice, hot summer weather are vomited and diarrhoea, infantile malnutrition, and oedema is small
Just unfavorable, habitual constipation, furunculosis carbuncle swells, venomous snake bite.Chromone and its derivative are widely present in plant, some are coloured
Substance thus its parent is referred to as chromone.Chromone compounds are because it is with multiple biological activities, by the extensive concern of scientific research personnel,
By showing that its physiological activity replaces situation to have very closely with it to its structure activity study, the hair of new chromone derivative
Now it is of great significance.A kind of present invention isolated chromone with activity of resisting tobacco mosaic virus from handle gland senna
Relevant report is not yet seen in derivative, the compound.
Summary of the invention
The first object of the present invention is to provide a kind of chromone derivative；Second is designed to provide the chromone derivative
Preparation method；Third is designed to provide the chromone derivative and is preparing the application in resisting tobacco mosaic disease drug.
The first object of the present invention is achieved in that the compound is from handle gland senna (Cassia pumila
Lam. isolated in), molecular formula C16H16O6, which has a structure in which
The compound is yellow jelly, is named as 8- hydroxyl -2- (3- hydroxypropyl) -5- (isobutyryl) -4H-4- color
Ketone, English name: 8-hydroxy-2- (3-hydroxypropanoyl) -5- (isobutyryl) -4H-chromen-4-one.
The second object of the present invention is achieved in that the preparation method of the chromone derivative is with the plant of handle gland senna
Strain is raw material, is prepared through crushing, medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography, gel filtration chromatography step.
Wherein in the medicinal extract extraction step, it is rounded the handle gland senna of strain, handle gland senna can crush or be cut into small
Section, with high concentration methanol (w%:80%~100%) or high concentration ethanol (w%:80%~100%) or high concentration acetone
(w%:70%~100%) is Extraction solvent, and Extraction solvent: handle gland senna (weight ratio)=2~4:1 impregnates for 24 hours~72h,
It extracts 3~5 times, combined extract, filtering and concentrating are at medicinal extract；
Wherein in the silica gel column chromatography step, pure methanol or straight alcohol or pure C that medicinal extract is measured with 1.5~3 times of weight ratio
0.8~1.5 times of weight ratio of 80~100 mesh silica gel mixed samples, 150~200 mesh silicon measured with 2~5 times of weight ratio are used after ketone dissolution
Glue dry column-packing carries out silica gel column chromatography；It is the chlorine of 20:1~5:5 (20:1,9:1,8:2,7:3,6:4,5:5) with volume proportion
Imitation-carbinol solution carries out gradient elution, merges the part of identical polar, collects each section eluent and is concentrated；
Wherein in the high pressure liquid chromatography purification procedures, high pressure is further used in the part 9:1 of column chromatographic eluate
Liquid chromatogram isolates and purifies up to the flavone compound, and it is to use 20mm × 250mm that high pressure liquid chromatography, which isolates and purifies,
5 μm of C18Chromatographic column, flow velocity 20mL/min, the methanol that mobile phase is 58%, UV detector Detection wavelength are 356nm, often
Secondary 180 μ L of sample introduction, collects the chromatographic peak of 33.1min, is evaporated after repeatedly adding up.
Wherein in the gel filtration chromatography step, gained compound again with pure methanol dissolve, then with pure methanol be flowing
Phase is separated with gel filtration chromatography, further to isolate and purify.
The structure of prepared compound is identified by the following method:
Compound is yellow jelly, and HRESI-MS shows that its quasi-molecular ion peak is 327.0852 [M+Na]+(calculated value
327.0845), in conjunction with1H NMR and DEPT, which are composed, determines that its molecular formula is C16H16O6, degree of unsaturation 9.
Hydroxyl (3412cm is shown in infrared spectroscopy-1), carbonyl (1740,1682 and 1658cm-1) and aromatic ring (1613,
1568 and 1479cm-1) resonance absorbing peak.And ultraviolet spectra has absorption maximum to also illustrate compound in 242,281 and 356nm
In there may be aromatic ring structures.
Compound1H、13The H NMR spectroscopy (such as table 1, Fig. 1 and Fig. 2) of C and DEPT shows that it contains 16 carbon and 16 hydrogen, including
1 chromone ring system (C-2~C-10), 3 aromatic protons (H-3, H-6 and H-7), 1 3- hydroxypropyl group (- CO-CH2-
CH2-OH；C-11~C-13；H2- 12 and H2- 13), 1 isobutyryl group [(CH3)2-CH-CO-；C-14~C-16；H6-16,17
And H-15] and 1 hydroxyl (δH10.14).(such as Fig. 3) is it can be observed that H in the HMBC spectrum of compound2-12(δH 3.40)
With C-2 (δC157.0), H-3 (δH7.10) with C-11 (δC198.7) related, it can speculate that 3- hydroxypropyl moieties are substituted in C-2
Position；From H-15 (δH4.40) with C-5 (δC130.8), H-6 (δH7.49) with C-14 (δC208.9) related, it can speculate isobutyryl
Part is substituted in C-5；From methoxyl group proton (δH10.14) with C-8 (δC153.0) correlation can speculate that hydroxyl is substituted in C-8
Position.So far, the structure of compound is determined, Compound nomenclature are as follows: 8- hydroxyl -2- (3- hydroxypropyl) -5- (isobutyryl) -4H-
4- chromone.
Infrared, the ultraviolet and mass spectrometric data of compound: ultraviolet spectra (methanol), λmax(logε)210(4.12),242
(3.70),281(3.75),356(3.60)nm；Infrared spectroscopy (pressing potassium bromide troche): νmax3412,3090,2948,2855,
1740,1682,1658,1613,1568,1479,1342,1168,1053,906,817cm-1；1H and13C NMR data (500 Hes
125MHz, solvent CDCl3), it is shown in Table -1；Positive ion mode ESIMS m/z 327 [M+Na]+；Positive ion mode HRESIMS m/
z323.1252[M+Na]+(calculated value 323.1259, C16H16NaO6)。
- 1 compound of table1H NMR and13C NMR data (CDCl3)
The third object of the present invention, which is achieved in that, is applied to the chromone derivative in Tobacco mosaic medicine
Preparation.
The compounds of this invention is separated for the first time, has been determined by nuclear magnetic resonance and measuring method of mass spectrum as chromone
Derivative, and characterize its specific structure.Through the experiment to resisting tobacco mosaic virus, relative inhibition reaches 31.2%, tool
There is good activity of resisting tobacco mosaic virus, more than the relative inhibition (30.8%) of positive reference substance Nanning mycin.The above knot
Fruit discloses chromone derivative of the invention good application prospect in preparing resisting tobacco mosaic virus drug.Of the present inventionization
It is good to close the simple activity of object structure, can be used as the guiding compound of resisting tobacco mosaic virus drug.
Detailed description of the invention
Fig. 1 is the carbon-13 nmr spectra of compound.
Fig. 2 is the nuclear magnetic resonance spectroscopy of compound.
Fig. 3 is that the main HMBC of compound is related.
Specific embodiment
Below with reference to examples and drawings, the present invention is further illustrated, but is not subject in any way to the present invention
Limitation, based on present invention teach that made any transformation or improvement, each fall within the scope of the present invention.
Unless otherwise indicated, percentage employed in the present invention is mass percent.
The preparation of chromone derivative 8- hydroxyl -2- (3- hydroxypropyl) -5- (isobutyryl) -4H-4- chromone of the present invention
Method includes crushing, medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography and gel filtration chromatography step, is specifically included:
A, medicinal extract extracts: being rounded the handle gland senna plant of strain, handle gland senna can crush or be cut into segment, and use is highly concentrated
Spend methanol (w%:80%~100%) or high concentration ethanol (w%:80%~100%) or high concentration acetone (w%:70%~
It 100%) is Extraction solvent, Extraction solvent: tailed spicebush root and leaf (weight ratio)=2~4:1 impregnates for 24 hours~72h, extracts 3~5 times,
Combined extract, filtering and concentrating are at medicinal extract；
B, silica gel column chromatography: the pure methanol or straight alcohol or pure acetone that medicinal extract is measured with 1.5~3 times of weight ratio use weight after dissolving
Measure 80~100 mesh silica gel mixed samples than 0.8~1.5 times, 150~200 mesh silica gel dry column-packings measured with 2~5 times of weight ratio into
Row silica gel column chromatography；With volume proportion for 20:1~5:5 (20:1,9:1,8:2,7:3,6:4,5:5) chloroform-methanol into
Row gradient elution merges identical polar portion, collects each section eluent and is concentrated；
C, high pressure liquid chromatography separates: the part 9:1 of column chromatographic eluate is further isolated and purified with high pressure liquid chromatography
Up to the chromone derivative, it is using 20mm × 250mm, 5 μm of C that high pressure liquid chromatography, which isolates and purifies,18Chromatographic column, flow velocity
For 20mL/min, the methanol that mobile phase is 58%, UV detector Detection wavelength is 356nm, each 180 μ L of sample introduction, is collected
The chromatographic peak of 33.1min is evaporated after repeatedly adding up.
D, gel filtration chromatography: step C mesohigh liquid chromatography isolate and purify after substance through the high performance liquid chromatography
After isolating and purifying, gained compound is dissolved with pure methanol again, then using pure methanol as mobile phase, carries out chromatography point with gel column
From further to isolate and purify.
Chromone derivative of the present invention is preparing the application in resisting tobacco mosaic virus drug.
The raw materials used in the present invention is not limited by area and kind, and the present invention may be implemented, below with each from Yunnan
The present invention will be further described for the handle gland senna raw material on ground:
Embodiment 1
Handle gland senna sample source crushes handle gland senna sample 2.0kg with 95% methanol in Yunnan Xinping county
It extracts 5 times, extracts every time for 24 hours, extracting solution merges, and filtering is concentrated under reduced pressure into medicinal extract, obtains medicinal extract 106g.Medicinal extract weight ratio 2.0
The thick silica gel mixed sample of 80 mesh of 120g is used after the pure methanol dissolution of amount again, the 160 mesh silica gel of 0.7kg fill column progress silica gel column chromatography,
With the chloroform-methanol gradient elution that volume proportion is 20:1,9:1,8:2,7:3,6:4,5:5, TLC monitoring merges identical portion
Point, 6 parts are obtained, wherein volume proportion is that the LC-8A of the chloroform-methanol elution fraction Shimadzu of 9:1 partly prepares efficient liquid
Phase chromatographic isolation, using 58% methanol as mobile phase, Venusil MP C18It is stationary phase, stream that (20 × 250mm, 5 μm), which prepares column,
Speed is 20ml/min, and UV detector Detection wavelength is 356nm, and each 180 μ L of sample introduction collects the chromatographic peak of 33.1min, repeatedly
It is evaporated after cumulative；Products therefrom is dissolved with pure methanol again, then using pure methanol as mobile phase, with Sephadex LH-20 gel column
Chromatography is to get the noval chemical compound.
Embodiment 2
Handle gland senna sample source is in Yunnan Shuan Jiangxian, by the sampling 4.0kg chopping of handle gland senna, with 95% ethyl alcohol
It extracts 4 times, extracts 48h every time, extracting solution merges, and filtering is concentrated under reduced pressure into medicinal extract, obtains medicinal extract 196g.Medicinal extract weight ratio 2.0
The thick silica gel mixed sample of 100 mesh of 200g is used after the pure methanol dissolution of amount again, the 200 mesh silica gel dress column progress silica gel column chromatography of 1kg is used
Volume proportion is the chloroform-methanol gradient elution of 20:1,9:1,8:2,7:3,6:4,5:5, and TLC monitoring merges identical part,
6 parts are obtained, wherein volume proportion is that chloroform-acetone elution fraction Shimadzu LC-8A of 9:1 partly prepares high-efficient liquid phase color
Spectrum separation, using 58% methanol as mobile phase, Venusil MP C18It is stationary phase that (20 × 250mm, 5 μm), which prepares column, and flow velocity is
20ml/min, UV detector Detection wavelength are 356nm, and each 180 μ L of sample introduction collects the chromatographic peak of 33.1min, repeatedly cumulative
After be evaporated；Products therefrom is dissolved with pure methanol again, then using pure methanol as mobile phase, with Sephadex LH-20 gel filtration chromatography
Separation is to get the noval chemical compound.
Embodiment 3
Handle gland senna sample source crushes handle gland senna sample 6kg in Jinghong City, Yunnan Province, is used with 80% acetone
Ultrasonic extraction 3 times, 72h is extracted every time, and extracting solution merges, and filtering is concentrated under reduced pressure into medicinal extract, obtains medicinal extract 319g.Medicinal extract weight
With the thick silica gel mixed sample of 80 mesh of 400g, the 180 mesh silica gel dress column progress silica gel column layer of 2kg after the pure methanol dissolution measured than 1.6 times
Analysis, with the chloroform-methanol gradient elution that volume proportion is 20:1,9:1,8:2,7:3,6:4,5:5, TLC monitoring merges identical
Part obtains 6 parts, and chloroform-acetone elution fraction Shimadzu LC-8A half that wherein volume proportion is 9:1 prepares efficient
Liquid chromatogram separation, using 58% methanol as mobile phase, Venusil MP C18It is stationary phase that (20 × 250mm, 5 μm), which prepares column,
Flow velocity is 20ml/min, and UV detector Detection wavelength is 356nm, and each 180 μ L of sample introduction collects the chromatographic peak of 33.1min, more
It is secondary it is cumulative after be evaporated；Products therefrom is dissolved with pure methanol again, then using pure methanol as mobile phase, with Sephadex LH-20 gel
Column chromatography for separation is to get the noval chemical compound.
Embodiment 4
Compound prepared by Example 1 is yellow jelly.
Compound is yellow jelly, and HRESI-MS shows that its quasi-molecular ion peak is 327.0852 [M+Na]+(calculated value
327.0845), in conjunction with1H NMR and DEPT, which are composed, determines that its molecular formula is C16H16O6, degree of unsaturation 9.
Hydroxyl (3412cm is shown in infrared spectroscopy-1), carbonyl (1740,1682 and 1658cm-1) and aromatic ring (1613,
1568 and 1479cm-1) resonance absorbing peak.And ultraviolet spectra has absorption maximum to also illustrate compound in 242,281 and 356nm
In there may be aromatic ring structures.
Compound1H、13The H NMR spectroscopy (such as table 1, Fig. 1 and Fig. 2) of C and DEPT shows that it contains 16 carbon and 16 hydrogen, including
1 chromone ring system (C-2~C-10), 3 aromatic protons (H-3, H-6 and H-7), 1 3- hydroxypropyl group (- CO-CH2-
CH2-OH；C-11~C-13；H2- 12 and H2- 13), 1 isobutyryl group [(CH3)2-CH-CO-；C-14~C-16；H6-16,17
And H-15] and 1 hydroxyl (δH10.14).(such as Fig. 3) is it can be observed that H in the HMBC spectrum of compound2-12(δH 3.40)
With C-2 (δC157.0), H-3 (δH7.10) with C-11 (δC198.7) related, it can speculate that 3- hydroxypropyl moieties are substituted in C-2
Position；From H-15 (δH4.40) with C-5 (δC130.8), H-6 (δH7.49) with C-14 (δC208.9) related, it can speculate isobutyryl
Part is substituted in C-5；From methoxyl group proton (δH10.14) with C-8 (δC153.0) correlation can speculate that hydroxyl is substituted in C-8
Position.So far, the structure of compound is determined, Compound nomenclature are as follows: 8- hydroxyl -2- (3- hydroxypropyl) -5- (isobutyryl) -
4H-4- chromone.
Embodiment 5
Compound prepared by Example 2 is orange colour jelly.Measuring method is same as Example 4, confirms embodiment
The compound of 2 preparations is the flavone compound: 8- hydroxyl -2- (3- hydroxypropyl) -5- (isobutyryl) -4H-4- chromone.
Embodiment 6
Compound prepared by Example 3 is orange colour jelly.Measuring method is same as Example 4, confirms embodiment
The compound of 3 preparations is the flavone compound: 8- hydroxyl -2- (3- hydroxypropyl) -5- (isobutyryl) -4H-4- chromone.
Embodiment 7
Any chromone derivative prepared by Example 1~3 carries out activity of resisting tobacco mosaic virus test, and test situation is such as
Under:
Using half leaf method, resisting tobacco mosaic disease is carried out to the compounds of this invention when the mass concentration of medicament is 50mg/L
Cytotoxic activity measurement.On the plant of 5~6 age flue-cured tobaccos, the blade (leaf row is normal, disease-free no worm) for being suitable for test is chosen, first will
Blade uniformly sprinkles fine emery powder, with writing brush by spare tobacco mosaic virus (TMV) source (3.0 × 10-3) be uniformly put on sprinkled with diamond dust
Blade on, after the blade to all middle choosings connects poison, be immediately placed in the culture dish for fill medical fluid and handle 20min, take out,
Droplet and medical fluid on blade are wiped, the recovery of two and half leaves is emitted in the glass jar for being covered with toilet paper moisturizing, and cover glass
Lid, temperature control (23 ± 2) DEG C are placed on greenhouse natural light irradiation, each processing of 2~3d, that is, visible withered spot set the other half leaf as pair
According to, be additionally provided with 1 group be commodity Ningnanmycin processing as a comparison, press formula calculate relative inhibition.
XI%=(CK-T)/CK × 100%
X: relative inhibition (%) CK: is soaked in the withered spot number (a) that half in clear water connects malicious leaf, T is soaked in medical fluid
Half connects the withered spot number (a) of malicious leaf.
As a result the relative inhibition of bright compound is 31.2%, higher than the relative inhibition of control Ningnanmycin
30.8%, illustrate that compound has preferable activity of resisting tobacco mosaic virus.
Claims (10)
1. the chromone derivative in a seedstalk gland senna, which is characterized in that its molecular formula is C16H16O6, have a structure in which
2. the preparation method of chromone derivative according to claim 1, which comprises the following steps: handle gland mountain
Hyacinth bean plant → crushing → medicinal extract extraction → silica gel column chromatography → high pressure liquid chromatography.
3. preparation method according to claim 2, which is characterized in that wherein with species Cassia platymiscium handle gland senna
(Cassia pumila Lam.) whole plant is raw material, crushing or dissection.
4. preparation method according to claim 2, which is characterized in that dense with quality wherein in the medicinal extract extraction step
Degree for 80%~100% methanol aqueous solution or mass concentration be 80%~100% ethanol water or mass concentration be
70%~100% aqueous acetone solution is Extraction solvent, and according to quality than Extraction solvent: handle gland senna=2~4:1 amount
For 24 hours~72h is impregnated, is extracted 3~5 times, combined extract, filtering and concentrating are at medicinal extract.
5. the preparation method according to claim 4, which is characterized in that wherein in the silica gel column chromatography step, medicinal extract silicon
Glue mixes 150~200 mesh silica gel dry column-packings measured after sample with 2~5 times of weight ratio and carries out silica gel column chromatography；It is with volume proportion
The chloroform-methanol system of 20:1~5:5 carries out gradient elution, merges identical polar portion, collects each section eluent
And it is concentrated.
6. preparation method according to claim 5, which is characterized in that wherein the medicinal extract is passing through silica gel column chromatography rough segmentation
Before, need to after the pure methanol of 1.5~3 times of weight ratio amounts or straight alcohol or pure acetone dissolution with the 80 of 0.8~1.5 times of weight ratio~
100 mesh silica gel carry out mixing sample.
7. preparation method according to claim 5, which is characterized in that wherein in the silica gel column chromatography step, chloroform-first
Alcoholic solution volume proportion is 20:1,9:1,8:2,7:3,6:4,5:5.
8. preparation method according to claim 7, which is characterized in that wherein in the column chromatography steps, the 9:1 of eluent
Part is further isolated and purified with high pressure liquid chromatography, wherein in the high pressure liquid chromatography separating step, high pressure liquid chromatography
Isolating and purifying is to use specification for 20mm × 250mm, 5 μm of C18Chromatographic column, flow velocity 20mL/min, the first that mobile phase is 58%
Alcohol water, UV detector Detection wavelength are 356nm, and each 180 μ L of sample introduction collects the chromatographic peak of 33.1min, are steamed after repeatedly adding up
It does to get the chromone derivative.
9. preparation method according to claim 8, which is characterized in that the wherein high pressure liquid chromatography purification procedures
Afterwards, gained compound is dissolved with pure methanol again, then using pure methanol as mobile phase, is separated with gel filtration chromatography, with further right
It is isolated and purified.
10. chromone derivative according to claim 1 is preparing the application in resisting tobacco mosaic virus drug.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102775375A (en) * | 2012-08-16 | 2012-11-14 | 云南民族大学 | Chromone compound, preparation method and application of chromone compound, anti-aids pharmaceutical composition prepared from chromone compound and preparation of anti-aids pharmaceutical composition |
| CN103554077A (en) * | 2013-10-29 | 2014-02-05 | 云南烟草科学研究院 | Chromone compound as well as preparation method and application thereof |
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2018
- 2018-11-19 CN CN201811375708.XA patent/CN109574973B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102775375A (en) * | 2012-08-16 | 2012-11-14 | 云南民族大学 | Chromone compound, preparation method and application of chromone compound, anti-aids pharmaceutical composition prepared from chromone compound and preparation of anti-aids pharmaceutical composition |
| CN103554077A (en) * | 2013-10-29 | 2014-02-05 | 云南烟草科学研究院 | Chromone compound as well as preparation method and application thereof |
Non-Patent Citations (4)
| Title |
|---|
| CONGFANG XIA,等: "A New Chromone from Stems of Cassia fistula and Its Anti-Tobacco Mosaic Virus Activities", 《ASIAN JOURNAL OF CHEMISTRY》 * |
| HU, QIU-FEN，等: "Chromones from the Twigs of Cassia fistula and Their Anti-Tobacco Mosaic Virus Activities", 《HETEROCYCLES -SENDAI THEN TOKYO-》 * |
| LIANG DENG，等: "A New Chromone from the Stems of Cassia fistula and Its Anti-Tobacco Mosaic Virus Activity", 《ASIAN JOURNAL OF CHEMISTRY》 * |
| YINKE LI，等: "Chromones from the stems of Cassia fistula and their anti-tobacco mosaic virus activities", 《PHYTOCHEMISTRY LETTERS》 * |
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