CN109265423A - A kind of chromone compounds and its preparation method and application - Google Patents
A kind of chromone compounds and its preparation method and application Download PDFInfo
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- CN109265423A CN109265423A CN201811384372.3A CN201811384372A CN109265423A CN 109265423 A CN109265423 A CN 109265423A CN 201811384372 A CN201811384372 A CN 201811384372A CN 109265423 A CN109265423 A CN 109265423A
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- medicinal extract
- chromone compounds
- organic solvent
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- chromone
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- 150000004777 chromones Chemical class 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 239000000284 extract Substances 0.000 claims abstract description 53
- 239000003960 organic solvent Substances 0.000 claims abstract description 41
- 241000723873 Tobacco mosaic virus Species 0.000 claims abstract description 23
- 239000003814 drug Substances 0.000 claims abstract description 11
- 229940079593 drug Drugs 0.000 claims abstract description 10
- 238000010898 silica gel chromatography Methods 0.000 claims abstract description 10
- 238000000605 extraction Methods 0.000 claims abstract description 8
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 7
- 238000000638 solvent extraction Methods 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 103
- 239000012071 phase Substances 0.000 claims description 40
- 239000003480 eluent Substances 0.000 claims description 34
- 239000000243 solution Substances 0.000 claims description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 238000010828 elution Methods 0.000 claims description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 16
- 239000000741 silica gel Substances 0.000 claims description 16
- 229910002027 silica gel Inorganic materials 0.000 claims description 16
- 239000007864 aqueous solution Substances 0.000 claims description 14
- OTAFHZMPRISVEM-UHFFFAOYSA-N benzo-gamma-pyrone Natural products C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 claims description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 9
- 239000003208 petroleum Substances 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 8
- 239000013049 sediment Substances 0.000 claims description 8
- 238000001514 detection method Methods 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 230000005526 G1 to G0 transition Effects 0.000 claims description 6
- 238000004440 column chromatography Methods 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 238000002137 ultrasound extraction Methods 0.000 claims description 5
- 238000013375 chromatographic separation Methods 0.000 claims description 4
- 238000011097 chromatography purification Methods 0.000 claims description 4
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 claims description 4
- 235000019441 ethanol Nutrition 0.000 claims description 4
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical group OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 230000003595 spectral effect Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 39
- 230000000694 effects Effects 0.000 abstract description 7
- 238000012360 testing method Methods 0.000 abstract description 6
- 244000037364 Cinnamomum aromaticum Species 0.000 abstract description 3
- 235000014489 Cinnamomum aromaticum Nutrition 0.000 abstract description 2
- 241000220485 Fabaceae Species 0.000 abstract description 2
- 241000196324 Embryophyta Species 0.000 description 18
- -1 chromone compound Chemical class 0.000 description 12
- 235000021251 pulses Nutrition 0.000 description 12
- 241000700605 Viruses Species 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- BEBIIRLVYJMQOS-UHFFFAOYSA-N (2'S)-2-(propan-2'-ol)-5-hydroxy-benzopyran-4-one Natural products C1=CC=C2OC(CC(O)C)=CC(=O)C2=C1O BEBIIRLVYJMQOS-UHFFFAOYSA-N 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 241000208125 Nicotiana Species 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 229930013930 alkaloid Natural products 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 2
- FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229930003935 flavonoid Natural products 0.000 description 2
- 150000002215 flavonoids Chemical class 0.000 description 2
- 235000017173 flavonoids Nutrition 0.000 description 2
- 238000001052 heteronuclear multiple bond coherence spectrum Methods 0.000 description 2
- 238000002114 high-resolution electrospray ionisation mass spectrometry Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 150000003648 triterpenes Chemical class 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- AMNAZJFEONUVTD-KEWDHRJRSA-N (2s,3s,4s,5r,6r)-6-(4-amino-2-oxopyrimidin-1-yl)-4,5-dihydroxy-3-[[(2s)-3-hydroxy-2-[[2-(methylamino)acetyl]amino]propanoyl]amino]oxane-2-carboxamide Chemical compound O1[C@H](C(N)=O)[C@@H](NC(=O)[C@H](CO)NC(=O)CNC)[C@H](O)[C@@H](O)[C@@H]1N1C(=O)N=C(N)C=C1 AMNAZJFEONUVTD-KEWDHRJRSA-N 0.000 description 1
- 244000281594 Cassia siamea Species 0.000 description 1
- 235000006715 Cassia siamea Nutrition 0.000 description 1
- FEACDOXQOYCHKU-UHFFFAOYSA-N Gougerotin Natural products CNCC(=O)NC1=NC(=O)N(C=C1)C2OC(C(O)C(NC(=O)C(N)CO)C2O)C(=O)N FEACDOXQOYCHKU-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241001495644 Nicotiana glutinosa Species 0.000 description 1
- 241001529246 Platymiscium Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000012271 agricultural production Methods 0.000 description 1
- 230000002507 anti-phytoviral effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 230000002155 anti-virotic effect Effects 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 229930015036 aurone Natural products 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 239000002254 cytotoxic agent Substances 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000001085 differential centrifugation Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000012306 spectroscopic technique Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
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
Abstract
The invention discloses a kind of chromone compounds and its preparation method and application, the chromone compounds are isolated from leguminosae cassia arbor, molecular formula C12H12O5, it is named as (2 'S) -2- (propan-2 '-ol) -5,7-dihydroxy-benzopyran-4-one, there is following structural formula:The preparation method of the chromone compounds, be to dry pulse family arbor branch, leaf as raw material, through medicinal extract extraction, organic solvent extraction, silica gel column chromatography, high pressure liquid chromatography separating step and obtain.The chromone compounds tests prove that, have good activity of resisting tobacco mosaic virus, the compounds of this invention structure is simple, activity it is good, can be used as the guiding compound of resisting tobacco mosaic virus drug.
Description
Technical field
The invention belongs to effective ingredients in plant extractive technique fields, and in particular to a kind of chromone compounds and its preparation side
Method and application.
Background technique
The viroses of plant have the title of " plant cancer ", are one of important diseases in agricultural production.Since plant virus belongs to exhausted
Internal parasite, itself noenergy metabolic system have high dependency, thus plant virus to host plant cell
The prevention and treatment of disease is always a great problem in control of plant disease.It is just made it is estimated that China is often only tobacco mosaic virus (TMV) one
At about more than 500,000,000 yuan of economic loss!Therefore, it finds safely and effectively Antiphytoviral drug and receives bioscience man of various countries
Attention.Have that environment compatibility is good, safety, exploitation using natural plant active substance as the plant antiviral agent of effective component
The advantages that at low cost, meets the trend and requirement of pesticide in future development, there is preferable development and application prospect.In recent years, it plants
The research of material resource antivirotic has been increasingly subject to people's attention.For this reason, this experiment is with tobacco mosaic virus (TMV) (tobacco
Mosaic virus, T MV) it is object, the antiviral activity of cassia siamea is studied, to be China's traditional medicine
Data are accumulated with the research and development of novel plant source biological pesticide with making full use of for plant resources.
Leguminosae cassia (Cassia L.) about 600 kinds of the plant whole world, whole world subtropical and tropical zones are distributed in,
Minority distribution to Temperate Region in China, China produces more than 20, is widely distributed in each provinces and regions in north and south.Most of species Cassia platymiscium all has one
Fixed medical value is highly important a part in China's Chinese Traditional Medicine.Cassia plant or natural chromone
(chromone) one of the main resource of constituents, the anti-tumor activity with broad spectrum high-effect, is natural production antitumor in recent years
One of research hotspot of object.In addition to chromone (chromone) class, flavonoids (flavonoid), Anthraquinones
(anthraquinones), the compounds such as triterpenes (triterpenes) and alkaloids (alkaloids) are also graminaceous plant
Characteristic chemical constituent, it may have multiple biological activities.In order to more effectively utilize China's legume germplasm resource, therefrom finding has
The active constituent of development prospect, we select to carry out pulse family Caesalpinoidea plant the study of active components work compared with system.
The present invention isolated new chromone compound from leguminous plant, the compound have significant anti-tobacco
Mosaic virus activity.
Summary of the invention
The first object of the present invention is to provide a kind of chromone compounds；Second is designed to provide the chromone class chemical combination
The preparation method of object；Third is designed to provide the chromone compounds and is preparing answering in resisting tobacco mosaic virus drug
With.
The first object of the present invention is achieved in that the chromone compounds are from dry pulse family arbor branch, leaf
In isolated, molecular formula C12H12O5, it is named as (2 'S)-2-(propan-2′-ol)-5,7-dihydroxy-
Benzopyran-4-one has following structural formula:
The compound is Light brown solid.The second object of the present invention is achieved in that the system of the chromone compounds
Preparation Method is to dry pulse family arbor branch, leaf as raw material, through medicinal extract extraction, organic solvent extraction, silica gel column chromatography, efficiently
Liquid chromatogram separation obtains, specifically:
A, medicinal extract extracts: pulse family arbor branch, leaf coarse powder is broken to 20 ~ 40 mesh, with organic solvent ultrasonic extraction 2 ~ 4 times,
30 ~ 60 min every time, extracting solution merge；Extracting solution filtering when extracting solution to 1/4 ~ 1/2 volume is concentrated under reduced pressure, is stood,
Sediment is filtered out, medicinal extract a is condensed into；
B, organic solvent extracts: the water of 1 ~ 2 times of weight ratio amount being added in medicinal extract a, is extracted with the isometric organic solvent of water
3 ~ 5 times, merge organic solvent extraction phase, is concentrated under reduced pressure into medicinal extract b；
C, silica gel column chromatography: the organic solvent that medicinal extract b is measured with 1.5 ~ 3 times of weight ratio dissolves, then 0.8 is weighed with medicinal extract ~
1.2 times of 100 ~ 200 mesh silica gel mixed samples, then upper silica gel column chromatography, dress column silica gel are 200 ~ 300 mesh, and dosage is medicinal extract
6 ~ 8 times of b weight amounts；The mixed organic solvents gradient elution for being 1:0 ~ 0:1 with volume ratio collects gradient eluent, dense
Contracting, monitors through TLC, merges identical part；
D, reversed phase column chromatography: reversed phase column chromatography on the eluent that the organic solvent matched with 40:1 is afforded, instead
Phase column is with reversed material C-18, C-8 or ODS dress column；Ladder is carried out with the methanol aqueous solution that volume content is 40 ~ 100%
Degree elution is collected each section eluent and is concentrated, monitors through TLC, merge identical part；
E, high performance liquid chromatography separation: will be with the eluent that 40 ~ 60% methanol aqueous solution of volume content affords through efficient liquid
Phase chromatographic separation and purification is to get the chromone compounds.
The structure of the chromone compounds in the above way prepared is to determine to come by the following method:
The compounds of this invention is Light brown solid；Ultraviolet spectra (solvent is methanol),λ max (logε: 223 (4.24), 252
(3.78), 296 (3.55) nm；Infrared spectroscopy (pressing potassium bromide troche)ν max 3425, 2910, 2860, 1656, 1627,
1460, 1370, 1130, 941, 831 cm-1；Optically-active: [α] 22.3 D=+ 53.42 (c = 0.15, MeOH)。
HRESIMS shows the compounds of this invention quasi-molecular ion peakm/z 235.2128 [M-H]-(calculated value 235.2123), knot
It closes13C and1H H NMR spectroscopy (figure -1 and figure -2, attribution data is shown in Table -1) provides its molecular formula C12H12O5, degree of unsaturation 7.
The compound13The display of C-NMR spectrum its contain 12 carbon signals: 1 carbonyl carbon (δ C184.1), 6 aromatic carbons, 2
A olefinic carbon (δ C 110.2,169.9) and 2- hydroxypropyl (δ C 44.7, 66.5, 23.7)；1H-NMR is shownδ H 6.17
(1H, d, J=2.0 Hz, H-6) and 6.31 (1H, d,J=2.0 Hz, H-8) it is the phenyl ring proton that a pair of of meta position replaces
Signal,δ H 6.09 (1H, s) are an alkene hydrogen signal,δ H2.66 (1H, dd, J = 14.4, 8.0 Hz, H-1′a)、
2.74 (1H, dd, J = 14.4, 4.8 Hz, H-1′b)、4.18 (1H, m, H-2′)、1.27 (3H, d, J =
6.2 Hz, H-3 ') be 2- hydroxypropyl in proton signal.13C NMR illustrates that the compound is the chromone knot that 2- hydroxypropyl replaces
Structure.Above data and reported in the literature (2 'S) -2- (propan-2 '-ol) -5-hydroxy-benzopyran-4-one is basic
Unanimously, show the compound and its skeleton structure having the same, unique difference is the chromone parent nucleus of the compound
Middle substitution is there are two meta-hydroxyl, containing the phenyl ring proton signal replaced there are two meta position, and compound (2 'S)-2-(propan-
2 '-ol) -5-hydroxy-benzopyran-4-one parent nucleus in only replace and have a hydroxyl, in phenyl ring then there are three tools
Adjacent Hydrogen Proton signal.In HMBC spectrum (Fig. 3), the hydrogen of 2- hydroxypropylδ H 2.66 (1H, dd, J = 14.4, 8.0
Hz, H-1′a), δ H2.74 (1H, dd, J =14.4,4.8 Hz, H-1 ' b) with C-2 (169.9), C-3 (110.2)
There is correlation,δ H 4.18 (1H, m, H-2 ') have related to C-2 (169.9), illustrate that 2- hydroxypropyl is connected in the C- of chromone parent nucleus
2, in addition,δ H 6.17 (1H, d, J =2.0 Hz, H-6) have to C-8 (95.1), C-10 (105.5) it is long-range related,δ H 6.31 (1H, d, J =2.0 Hz, H-8) have to C-6 (100.2), C-10 (105.5) it is long-range related,δ H 6.09
(1H, s, H-3) has long-range related to C-1 ' (44.7), C-10 (105.5).In addition, the compound and (2 'S)-2-
(propan-2 '-ol) -5-hydroxy-benzopyran-4-one optical activity having the same, shows that compound 1 has with it
Identical configuration, therefore, authenticating compound structure are (2 'S)-2-(propan-2′-ol)-5,7-dihydroxy-
benzopyran-4-one。
1 compound of table1H and13C NMR data (400/100 MHz, CD3OD)
The third object of the present invention, which is achieved in that, to be applied to the chromone compounds to prepare resisting tobacco mosaic virus
Drug.
Chromone compounds of the present invention are separated for the first time, have been determined by nuclear magnetic resonance and measuring method of mass spectrum
For chromone compounds, and characterize its specific structure.Using the compounds of this invention as raw material, through the reality to resisting tobacco mosaic virus
It tests, inhibiting rate reaches 21.6 ± 2.7%, has good activity of resisting tobacco mosaic virus, mould close to positive reference substance Nanning
The inhibiting rate (26.5%) of element.Result above disclose the compound of the present invention have in preparing resisting tobacco mosaic virus drug it is good
Good application prospect.
The simple activity of the compounds of this invention structure is good, can be used as the guiding compound of resisting tobacco mosaic virus drug.
Detailed description of the invention
Fig. 1 be compound carbon-13 nmr spectra (13C NMR)；
Fig. 2 be compound nuclear magnetic resonance spectroscopy (1H NMR)；
Fig. 3 is that the main HMBC of compound is related.
Specific embodiment
The present invention will be further described below with reference to the drawings, but the present invention is limited in any way, base
In present invention teach that made any transformation or improvement, each fall within protection scope of the present invention.
Chromone compounds of the present invention be it is isolated from dry pulse family arbor branch, leaf, molecular formula is
C12H12O5, it is named as (2 'S) -2- (propan-2 '-ol) -5,7-dihydroxy-benzopyran-4-one, have following
Structural formula:
The preparation method of chromone compounds of the present invention is to be mentioned using drying pulse family arbor branch, leaf as raw material through medicinal extract
It takes, organic solvent extraction, silica gel column chromatography, high performance liquid chromatography separation acquisition, specifically:
A, medicinal extract extracts: pulse family arbor branch, leaf coarse powder is broken to 20 ~ 40 mesh, with organic solvent ultrasonic extraction 2 ~ 4 times,
30 ~ 60 min every time, extracting solution merge；Extracting solution filtering when extracting solution to 1/4 ~ 1/2 volume is concentrated under reduced pressure, is stood,
Sediment is filtered out, medicinal extract a is condensed into；
B, organic solvent extracts: the water of 1 ~ 2 times of weight ratio amount being added in medicinal extract a, is extracted with the isometric organic solvent of water
3 ~ 5 times, merge organic solvent extraction phase, is concentrated under reduced pressure into medicinal extract b；
C, silica gel column chromatography: the organic solvent that medicinal extract b is measured with 1.5 ~ 3 times of weight ratio dissolves, then 0.8 is weighed with medicinal extract ~
1.2 times of 100 ~ 200 mesh silica gel mixed samples, then upper silica gel column chromatography, dress column silica gel are 200 ~ 300 mesh, and dosage is medicinal extract
6 ~ 8 times of b weight amounts；The mixed organic solvents gradient elution for being 1:0 ~ 0:1 with volume ratio collects gradient eluent, dense
Contracting, monitors through TLC, merges identical part；
D, reversed phase column chromatography: reversed phase column chromatography on the eluent that the organic solvent matched with 40:1 is afforded, instead
Phase column is with reversed material C-18, C-8 or ODS dress column；Ladder is carried out with the methanol aqueous solution that volume content is 40 ~ 100%
Degree elution is collected each section eluent and is concentrated, monitors through TLC, merge identical part；
E, high performance liquid chromatography separation: will be with the eluent that 40 ~ 60% methanol aqueous solution of volume content affords through efficient liquid
Phase chromatographic separation and purification is to get the chromone compounds.
Organic solvent described in step A is any one of acetone, ethyl alcohol or methanol.
Organic solvent concentration described in step A is 70 ~ 99%.
Organic solvent described in step B is ethyl acetate, chloroform, ether, petroleum ether or benzene.
Mixed organic solvents described in step C are methylene chloride-methanol, petroleum ether-acetone, dichloromethane-ethyl acetate
Or petroleum ether-ethyl acetate.
The volume proportion of mixed organic solvents described in step C is 1:0,40:1,30:1,20:1,9:1,4:1,7:3,3:
2、1:1、1:2、0:1。
The purifying of high performance liquid chromatography separation described in E step is the flow velocity 3ml/ using 40 ~ 70% methanol as mobile phase
Min, 22 × 250 mm, 5 μm of reverse phase preparative column are stationary phase, and UV detector Detection wavelength is 254 nm, each sample introduction
10 ~ 50 μ L collect the chromatographic peak of 10 ~ 50min, are evaporated after repeatedly adding up.Chromone compounds of the present invention application be
Preparing the application in resisting tobacco mosaic virus drug.
Leguminous plant of the present invention is not limited by area and kind, and the present invention may be implemented.
Embodiment 1
Dry pulse family arbor branch, 5.5 kg of leaf are taken, coarse powder is broken to 40 mesh, it is extracted 4 times with 90% EtOH Sonicate,
Each 30min, extracting solution merge；Extracting solution filtering, is concentrated under reduced pressure into the 1/4 of volume；It stands, filters out sediment, be condensed into
300g medicinal extract a；300g water is added in medicinal extract a, is extracted 5 times with the isometric ethyl acetate of water, merges extraction
Phase is concentrated under reduced pressure into 170g medicinal extract b；Column is filled with 200-300 mesh silica gel 2000g, 200g is added in medicinal extract b
Methanol dissolution, then be added 100-200 mesh silica gel 170g mix sample, mix upper prop after sample；It is respectively 1:0 with volume ratio,
The methylene chloride-methanol mixed organic solvents gradient elution of 40:1,30:1,20:1,9:1,8:2,7:3,6:4 are collected
Gradient eluent, concentration, monitor through TLC, merge identical part, obtain 8 parts, the dichloromethane of volume ratio 40:1
Alkane-methanol mixed organic solvents eluent c is 16g；Column is filled with reversed material C-18, reversed-phase column on eluent c,
Gradient elution is carried out with the methanol aqueous solution that volume content is 20 ~ 100%, each section eluent is collected and is concentrated, through TLC
Monitoring, merges identical part；The eluent afforded with 40 ~ 60% methanol aqueous solution of volume content is taken, then with 52%
Methanol be mobile phase, flow velocity 3ml/min, 22 × 250 mm mm, 5 μm of Agilent C18 reverse phase preparative column is solid
Determine phase, UV detector Detection wavelength is 254 nm, each 50 μ L of sample introduction, collects the chromatographic peak of 12 min, repeatedly cumulative
It is evaporated afterwards to get the chromone compounds (2 'S)-2-(propan-2′-ol)-5,7-dihydroxy-
benzopyran-4-one。
Embodiment 2
Dry pulse family arbor branch, leaf 3.2kg are taken, coarse powder is broken to 40 mesh, extracts 3 with aqueous 10% EtOH Sonicate
Secondary, each 20min, extracting solution merges；Extracting solution filtering, is concentrated under reduced pressure into the 1/3 of volume；It stands, filters out sediment, be concentrated
At 360g medicinal extract a；The water of 360g is added in medicinal extract a, is extracted 3 times, is merged with the isometric ethyl acetate of water
Extraction phase is concentrated under reduced pressure into 120g medicinal extract b；Column is filled with 200-300 mesh silica gel 1200g, is added in medicinal extract b
The methanol of 240g dissolves, and 100-200 mesh silica gel 120g is then added and mixes sample, mixes upper prop after sample；It is respectively with volume ratio
The dichloromethane-ethyl acetate mixed organic solvents gradient elution of 30:1,20:1,9:1,8:2,7:3,6:4,1:1,0:1 are received
Collect gradient eluent, concentration, is monitored through TLC, merge identical part；The dichloromethane-ethyl acetate of volume ratio 8:2 is mixed
The eluent c for closing organic solvent is 46g；Column, reversed-phase column on eluent c, with volume content are filled with reversed material C-18
Gradient elution is carried out for 20 ~ 100% methanol aqueous solution, each section eluent is collected and is concentrated, monitored through TLC, merge phase
Same part；It takes the eluent afforded with 40 ~ 60% methanol aqueous solution of volume content, then with 40% methanol is flowing
Phase, flow velocity 3ml/min, 22 × 250 mm mm, 5 μm of Agilent C18 reverse phase preparative column is stationary phase, ultraviolet detection
Device Detection wavelength is 254 nm, each 30 μ L of sample introduction, collects the chromatographic peak of 46 min, is evaporated after repeatedly adding up to get institute
The chromone compounds (2 ' statedS)-2-(propan-2′-ol)-5,7-dihydroxy-benzopyran-4-one。
Embodiment 3
Dry pulse family arbor branch, leaf 6.5kg are taken, coarse powder is broken to 30 mesh, with aqueous 20% methanol ultrasonic extraction 3
Secondary, each 20min, extracting solution merges；Extracting solution filtering, is concentrated under reduced pressure into the 1/2 of volume；It stands, filters out sediment, be concentrated
At 675g medicinal extract a；The water of 700g is added in medicinal extract a, is extracted 4 times with the isometric chloroform of water, merges extraction
Phase is concentrated under reduced pressure into 342g medicinal extract b；Column is filled with 200-300 mesh silica gel 3400g, 900g is added in medicinal extract b
Methanol dissolution, then be added 100-200 mesh silica gel 360g mix sample, mix upper prop after sample；With volume ratio be respectively 30:1,
The dichloromethane-acetone mixed organic solvents gradient elution of 20:1,9:1,8:2,7:3,6:4,1:1,0:1 collect gradient elution
Liquid, concentration, monitor through TLC, merge identical part；The dichloromethane-acetone mixed organic solvents of volume ratio 6:4 are washed
De- liquid c is 45g；Column, reversed-phase column on eluent c, the first for being 20 ~ 100% with volume content are filled with reversed material ODS
Alcohol solution carries out gradient elution, collects each section eluent and is concentrated, monitors through TLC, merge identical part；It takes with body
The eluent that product 40 ~ 60% methanol aqueous solution of content affords, then using 50% methanol as mobile phase, flow velocity 3ml/min,
22 × 250 mm mm, 5 μm of Agilent C18 reverse phase preparative column are stationary phase, and UV detector Detection wavelength is 254
Nm, each 40 μ L of sample introduction collect the chromatographic peak of 26 min, are evaporated after repeatedly adding up to get the chromone compounds
(2′S)-2-(propan-2′-ol)-5,7-dihydroxy-benzopyran-4-one。
Embodiment 4
Dry pulse family arbor branch, leaf and/or fruit 7.9kg are taken, coarse powder is broken to 40 mesh, extracts 3 with 90% ethyl alcohol
Secondary, extracting solution merges；Extracting solution filtering, is concentrated under reduced pressure into the 1/4 of volume；It stands, filters out sediment, be condensed into 860g leaching
Cream a；The water of 900g is added in medicinal extract a, with petroleum ether extraction 4 times isometric with water, merges extraction phase, decompression
It is condensed into 480g medicinal extract b；Column is filled with 200-300 mesh silica gel 5000g, the methanol that 500g is added in medicinal extract b is molten
Then solution is added 100-200 mesh silica gel 500g and mixes sample, mixes upper prop after sample；With volume ratio be respectively 30:1,20:1,9:1,
The acetone and ethyl acetate mixed organic solvents gradient elution of 8:2,7:3,6:4,1:1,0:1 collect gradient eluent, concentration,
It is monitored through TLC, merges identical part；The eluent c of the acetone and ethyl acetate mixed organic solvents of volume ratio 9:1
For 53g；Column is filled with reversed material C-8, reversed-phase column on eluent c is water-soluble with the methanol that volume content is 20 ~ 100%
Liquid carries out gradient elution, collects each section eluent and is concentrated, monitors through TLC, merge identical part；It takes with volume content
The eluent that 40 ~ 60% methanol aqueous solutions afford, then using 45% methanol as mobile phase, flow velocity 3ml/min, 22 × 250
Mm mm, 5 μm of Agilent C18 reverse phase preparative column are stationary phase, and UV detector Detection wavelength is 254 nm, every time
30 μ L of sample introduction collects the chromatographic peak of 36 min, is evaporated after repeatedly adding up to get the chromone compounds (2 'S)-
2-(propan-2′-ol)-5,7-dihydroxy-benzopyran-4-one。
Embodiment 5
Dry pulse family arbor branch, 3.6 kg of leaf are taken, coarse powder is broken to 20 mesh, with methanol ultrasonic extraction 3 times of 80%,
Each 30min, extracting solution merge；Extracting solution filtering, is concentrated under reduced pressure into the 1/2 of volume；It stands, filters out sediment, be condensed into
230g medicinal extract a；The water of 400g is added in medicinal extract a, with acetone extract 4 times isometric with water, merges extraction phase,
140g medicinal extract b is concentrated under reduced pressure into；Column is filled with 200-300 mesh silica gel 1600g, the second of 200g is added in medicinal extract b
Then acetoacetic ester dissolution is added 100-200 mesh silica gel 140g and mixes sample, mixes upper prop after sample；With volume ratio be respectively 30:1,
The petroleum ether-ethyl acetate mixed organic solvents gradient elution of 20:1,9:1,8:2,7:3,6:4,1:1,0:1 are collected gradient and are washed
De- liquid, concentration, monitor through TLC, merge identical part；The petroleum ether-ethyl acetate mixed organic solvents of volume ratio 1:1
Eluent c be 16g；Column, reversed-phase column on eluent c, with volume content for 20 ~ 100% are filled with reversed material ODS
Methanol aqueous solution carry out gradient elution, collect each section eluent simultaneously be concentrated, monitored through TLC, merge identical part；It takes
With the eluent that 40 ~ 60% methanol aqueous solution of volume content affords, then using 55% methanol as mobile phase, flow velocity 3ml/
Min, 22 × 250 mm mm, 5 μm of Agilent C18 reverse phase preparative column is stationary phase, and UV detector Detection wavelength is
254 nm, each 20 μ L of sample introduction collect the chromatographic peak of 9 min, are evaporated after repeatedly adding up to get the chromone class chemical combination
Object (2 'S)-2-(propan-2′-ol)-5,7-dihydroxy-benzopyran-4-one。
Embodiment 6
Compound prepared by Example 1 is Light brown solid；
Measuring method are as follows: use nuclear magnetic resonance, identify structure in conjunction with other spectroscopic techniques.
1) ultraviolet spectra (solvent is methanol),λ max (logε): 223 (4.24), 252 (3.78), 296
(3.55) nm；
2) infrared spectroscopy (pressing potassium bromide troche) νmax 3425, 2910, 2860, 1656, 1627, 1460, 1370,
1130, 941, 831 cm-1；
3) optically-active: [α] 22.3 D=+ 53.42 (c= 0.15, MeOH)；
4) HRESIMS shows the compounds of this invention quasi-molecular ion peakm/z 235.2128 [M-H]-(calculated value is
235.2123), in conjunction with13C and1H H NMR spectroscopy (figure -1 and figure -2, attribution data is shown in Table -1) provides its molecular formula C12H12O5, no
Saturation degree is 7.
The compound13The display of C-NMR spectrum its contain 12 carbon signals: 1 carbonyl carbon (δ C184.1), 6 aromatic carbons, 2
A olefinic carbon (δ C 110.2,169.9) and 2- hydroxypropyl (δ C 44.7, 66.5, 23.7)；1H-NMR is shownδ H 6.17
(1H, d, J=2.0 Hz, H-6) and 6.31 (1H, d,J=2.0 Hz, H-8) it is the phenyl ring proton that a pair of of meta position replaces
Signal,δ H 6.09 (1H, s) are an alkene hydrogen signal,δ H2.66 (1H, dd, J = 14.4, 8.0 Hz, H-1′a)、
2.74 (1H, dd, J = 14.4, 4.8 Hz, H-1′b)、4.18 (1H, m, H-2′)、1.27 (3H, d, J =
6.2 Hz, H-3 ') be 2- hydroxypropyl in proton signal.13C NMR illustrates that the compound is the chromone knot that 2- hydroxypropyl replaces
Structure.Above data and reported in the literature (2 'S) -2- (propan-2 '-ol) -5-hydroxy-benzopyran-4-one is basic
Unanimously, show the compound and its skeleton structure having the same, unique difference is the chromone parent nucleus of the compound
Middle substitution is there are two meta-hydroxyl, containing the phenyl ring proton signal replaced there are two meta position, and compound (2 'S)-2-(propan-
2 '-ol) -5-hydroxy-benzopyran-4-one parent nucleus in only replace and have a hydroxyl, in phenyl ring then there are three tools
Adjacent Hydrogen Proton signal.In HMBC spectrum (Fig. 3), the hydrogen of 2- hydroxypropylδ H 2.66 (1H, dd, J = 14.4, 8.0
Hz, H-1′a), δ H2.74 (1H, dd, J =14.4,4.8 Hz, H-1 ' b) with C-2 (169.9), C-3 (110.2)
There is correlation,δ H 4.18 (1H, m, H-2 ') have related to C-2 (169.9), illustrate that 2- hydroxypropyl is connected in the C- of chromone parent nucleus
2, in addition,δ H 6.17 (1H, d, J =2.0 Hz, H-6) have to C-8 (95.1), C-10 (105.5) it is long-range related,δ H 6.31 (1H, d, J =2.0 Hz, H-8) have to C-6 (100.2), C-10 (105.5) it is long-range related,δ H 6.09
(1H, s, H-3) has long-range related to C-1 ' (44.7), C-10 (105.5).In addition, the compound and (2 'S)-2-
(propan-2 '-ol) -5-hydroxy-benzopyran-4-one optical activity having the same, shows the compound and its
Configuration having the same, therefore, authenticating compound structure are (2 'S)-2-(propan-2′-ol)-5,7-dihydroxy-
benzopyran-4-one。
Embodiment 7
Compound prepared by Example 2 ~ 5 is Light brown solid.Measuring method is same as Example 6, confirms embodiment 2 ~ 5
The compound of preparation is the chromone compounds.
Embodiment 8
Different Aurone compound prepared by Example 1 ~ 5 carries out activity of resisting tobacco mosaic virus test, and test situation is as follows:
For trying host: TMV withered spot host's Nicotiana glutinosaNicotiana glutinosaL., TMV systemic infection host is common
CigaretteNicotiana tabacumL. K326, insect prevention temperature indoor culture.
For prelibation source: tobacco mosaic virus (TMV) (TMV, U1 strain), by tobacco research institute of Yunnan Province tobacco chemistry emphasis
Laboratory is stored on common cigarette K326.
Virus purification: it referring to the method for Gooding etc., modifies slightly.Classical symptom disease leaf is heavy through differential centrifugation, PEG
Purified virus behind shallow lake and the centrifugation of 10%~40% sucrose discontinuous density gradient.The virus of purification determines that quality is dense through UV scanning
Degree is 20 mg/mL [virus concentration=(A260 × dilution ratio) /].The virus of purification is protected
- 20 DEG C are stored in, is diluted to 32 with 0.01 M PBS using precedingμg/mL。
Inhibit dissemination measurement: using local lesion's method.Test compound is dissolved in DMSO and is diluted with distilled water
To required concentration, Ningnanmycin is used as positive control.Selection health, eugonic 5~6 leaf phase Nicotiana glutinosa, left half leaf inoculation
Compound and the isometric mixed liquor of virus, right half leaf inoculation distilled water (containing a small amount of DMSO) are made with the isometric mixed liquor of virus
Negative control.It is rinsed with water after inoculation.Every processing is inoculated with 4~5 blades, counts withered spot number after repeating 3 times, 3-4 days
Mesh calculates inhibiting rate.
Inhibiting rate=(control withered spot number-processing withered spot number)/control withered spot number × 100%
Test result
Through the experiment to resisting tobacco mosaic virus, inhibiting rate reaches 21.6 ± 2.7%, has good resisting tobacco mosaic disease
Cytotoxic activity, close to the inhibiting rate (26.5%) of positive reference substance Nanning mycin.Result above discloses the compound of the present invention and is making
There is good application prospect in standby resisting tobacco mosaic virus drug.The simple activity of the compounds of this invention structure is good, can be used as anti-cigarette
The guiding compound of showy flowers of herbaceous plants leaf disease cytotoxic drug.
Claims (9)
1. a kind of chromone compounds, it is characterised in that the chromone compounds are from dry pulse family arbor branch, Ye Zhongfen
From obtaining, molecular formula C12H12O5, it is named as (2 'S)-2-(propan-2′-ol)-5,7-dihydroxy-
Benzopyran-4-one has following structural formula:
。
2. a kind of preparation method of chromone compounds described in claim 1, it is characterised in that dry pulse family arbor branch
Item, leaf are raw material, are obtained through medicinal extract extraction, organic solvent extraction, silica gel column chromatography, high performance liquid chromatography separation, specifically:
A, medicinal extract extracts: pulse family arbor branch, leaf coarse powder is broken to 20 ~ 40 mesh, with organic solvent ultrasonic extraction 2 ~ 4 times,
30 ~ 60 min every time, extracting solution merge；Extracting solution filtering when extracting solution to 1/4 ~ 1/2 volume is concentrated under reduced pressure, is stood,
Sediment is filtered out, medicinal extract a is condensed into；
B, organic solvent extracts: the water of 1 ~ 2 times of weight ratio amount being added in medicinal extract a, is extracted with the isometric organic solvent of water
3 ~ 5 times, merge organic solvent extraction phase, is concentrated under reduced pressure into medicinal extract b；
C, silica gel column chromatography: the organic solvent that medicinal extract b is measured with 1.5 ~ 3 times of weight ratio dissolves, then 0.8 is weighed with medicinal extract ~
1.2 times of 100 ~ 200 mesh silica gel mixed samples, then upper silica gel column chromatography, dress column silica gel are 200 ~ 300 mesh, and dosage is medicinal extract
6 ~ 8 times of b weight amounts；The mixed organic solvents gradient elution for being 1:0 ~ 0:1 with volume ratio collects gradient eluent, dense
Contracting, monitors through TLC, merges identical part；
D, reversed phase column chromatography: reversed phase column chromatography on the eluent that the organic solvent matched with 40:1 is afforded, instead
Phase column is with reversed material C-18, C-8 or ODS dress column；Ladder is carried out with the methanol aqueous solution that volume content is 40 ~ 100%
Degree elution is collected each section eluent and is concentrated, monitors through TLC, merge identical part；
E, high performance liquid chromatography separation: will be with the eluent that 40 ~ 60% methanol aqueous solution of volume content affords through efficient liquid
Phase chromatographic separation and purification is to get the chromone compounds.
3. the preparation method of the chromone compounds according to claim 2, it is characterised in that organic molten described in step A
Agent is any one of acetone, ethyl alcohol or methanol.
4. the preparation method of chromone compounds according to claim 2, it is characterised in that organic solvent described in step A
Concentration is 70 ~ 99%.
5. the preparation method of the chromone compounds according to claim 2, it is characterised in that organic molten described in step B
Agent is ethyl acetate, chloroform, ether, petroleum ether or benzene.
6. the preparation method of the chromone compounds according to claim 2, it is characterised in that be mixed with described in step C
Solvent is methylene chloride-methanol, petroleum ether-acetone, dichloromethane-ethyl acetate or petroleum ether-ethyl acetate.
7. the preparation method of the chromone compounds according to claim 2, it is characterised in that be mixed with described in step C
The volume proportion of solvent is 1:0,40:1,30:1,20:1,9:1,4:1,7:3,3:2,1:1,1:2,0:1.
8. the preparation method of the chromone compounds according to claim 2, it is characterised in that efficient liquid described in E step
Phase chromatographic separation and purification is the flow velocity 3ml/min using 40 ~ 70% methanol as mobile phase, 22 × 250 mm, 5 μm of reverse phase system
Standby column is stationary phase, and UV detector Detection wavelength is 254 nm, each 10 ~ 50 μ L of sample introduction, collects the color of 10 ~ 50min
Spectral peak is evaporated after repeatedly adding up.
9. a kind of chromone compounds described in claim 1 are preparing the application in resisting tobacco mosaic virus drug.
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| CN113185484A (en) * | 2021-04-09 | 2021-07-30 | 江西中医药大学 | Chromone compound and preparation method and application thereof |
| 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 |
| CN115677473A (en) * | 2022-11-16 | 2023-02-03 | 广东一方制药有限公司 | Phenolic compound, method for extracting and separating phenolic compound from ricepaper pith and application |
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| 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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| 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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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113185484A (en) * | 2021-04-09 | 2021-07-30 | 江西中医药大学 | Chromone compound and preparation method and application thereof |
| CN113185484B (en) * | 2021-04-09 | 2023-05-02 | 江西中医药大学 | Chromone compound and preparation method and application thereof |
| 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 |
| CN115677473A (en) * | 2022-11-16 | 2023-02-03 | 广东一方制药有限公司 | Phenolic compound, method for extracting and separating phenolic compound from ricepaper pith and application |
| CN115677473B (en) * | 2022-11-16 | 2023-12-12 | 广东一方制药有限公司 | Phenolic compound, method for extracting and separating phenolic compound from medulla Tetrapanacis and application of phenolic compound |
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