CN107445934A - A kind of flavone compound and its preparation method and application - Google Patents
A kind of flavone compound and its preparation method and application Download PDFInfo
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- CN107445934A CN107445934A CN201710848544.7A CN201710848544A CN107445934A CN 107445934 A CN107445934 A CN 107445934A CN 201710848544 A CN201710848544 A CN 201710848544A CN 107445934 A CN107445934 A CN 107445934A
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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
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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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
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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
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
Abstract
The invention discloses a kind of flavone compound and its preparation method and application.The flavone compound is isolated from short leaf Cassia, and its molecular formula is C20H20O5, Compound nomenclature is：6,4 ' dimethoxy 7 (3 hydroxypropyl) flavones, English are entitled：6,4'dimethoxy 7 (3 hydroxypropyl) flavone, have following structures：.Preparation method includes medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography separation and gel filtration chromatography step.Using the application for described flavone compound in resisting tobacco mosaic virus medicine is prepared.The compound of the present invention has good application prospect in resisting tobacco mosaic virus medicine is prepared.The compounds of this invention activity simple in construction is good, can be as the guiding compound of resisting tobacco mosaic virus medicine.
Description
Technical field
The invention belongs to technical field of phytochemistry, and in particular to a kind of flavone compound and preparation method thereof and should
With.
Background technology
Short leaf Cassia（Cassia leschenaultiana DC.）For pulse family（Leguminosae）Cassia
（Cassia）Plant, alias ground sweet, the old rattan of ox of oil, great Ye sennas, the short top top of iron arrow, great Hua water gleditsia sinensis, belong to it is annual or
Perennial suffruticose draft, high 30-80 centimetres, sometimes up to 1 meter, stem is upright, branch, the dense yellow pubescence of spray.Short leaf
Cassia is born in height above sea level 500-2200 meters of patanas, shrubbery, roadsides, in southern areas such as Yunnan, Sichuan, Guangdong, Guangxi and
The country such as India, Burma, Vietnam, Indonesia is widely distributed, and its leaf and root have preferably to dysentery and disease of digestive tract
Curative effect, seed have stomach invigorating, diuresis and eliminate oedema and other effects.Flavone compound refers to two phenyl ring with phenolic hydroxyl group
（A- and B- rings）By a series of interconnected compounds formed of central thricarbon atom, its basic parent nucleus is 2- phenyl chromogens
Ketone, the functional groups such as phenolic hydroxyl group, methoxyl group, methyl, isopentene group are often connected with its structure.Flavones is widely present certain of nature
In a little plants and berry, total kind about more than 4,000.Flavones is a kind of very strong antioxidant, can effectively remove internal oxygen certainly
By base, blood circulation can be improved, cholesterol is reduced, oozing out for inflammatory biology enzyme can also be suppressed, wound healing can be promoted
And analgesic.A kind of present invention isolated flavone compound with activity of resisting tobacco mosaic virus from short leaf Cassia,
Relevant report is not yet seen in the compound.
The content of the invention
The first object of the present invention is to provide a kind of flavone compound；Second purpose is to provide described flavonoids
The preparation method of compound；3rd purpose is the application for providing described flavone compound.
The first object of the present invention be achieved in that the flavone compound be it is isolated from short leaf Cassia,
Its molecular formula is C20H20O5, Compound nomenclature is：6,4 '-dimethoxy -7- (3- hydroxypropyls)-flavones, English are entitled：6,4'-
Dimethoxy-7- (3- hydroxypropyl)-flavone, has following structures：
。
The second object of the present invention be achieved in that with short leaf Cassia (Cassia leschenaultiana DC.) it is raw material, extracted through medicinal extract, the separation of silica gel column chromatography, high pressure liquid chromatography and gel filtration chromatography step are prepared, tool
Body comprises the following steps：
A, medicinal extract extracts：Take the short leaf Cassia of raw material (Cassia leschenaultiana DC.), using whole plant as raw material or
Segment is crushed and be cut into, the organic solvent that raw material weighs 2 ~ 4 times of mass concentration 70 ~ 100% is added, 24 ~ 72h of soak extraction, carries
Take 3 ~ 5 times, merge extract solution, filtering and concentrating into medicinal extract；
B, silica gel column chromatography：Medicinal extract carries out silica gel column chromatography with 150 ~ 200 mesh silica gel dry column-packings of 2 ~ 5 times of medicinal extract weight, with
Volume proportion is 20:1~5:5 chloroform-methanol carries out gradient elution, merges identical part, collects each several part eluent
And concentrate；
C, high pressure liquid chromatography separates：By the 8 of eluent:2 parts are further isolated and purified to obtain target with high pressure liquid chromatography
Thing flavone compound.
The structure of prepared compound is identified by the following method：
Compound is orange-yellow jelly, and HRESI-MS shows that its quasi-molecular ion peak is 363.1202 [M+Na]+(calculated value
363.1208), with reference to1H NMR and DEPT spectrum determine that its molecular formula is C20H20O5, degree of unsaturation 11.
Hydroxyl (3416 cm are shown in infrared spectrum-1), carbonyl (1665 cm-1) and aromatic ring (1612,1562 and 1449
cm-1) resonance absorbing peak.And ultraviolet spectra there may be in 210,263,362 nm have absorption maximum to also illustrate that compound
Aromatic ring structure.
Compound1H and13C H NMR spectroscopies（Such as table 1, Fig. 1 and Fig. 2）Show that it contains 20 carbon and 20 hydrogen, including 1
1,2,4,5- quaternary phenyl ring (C-5 ~ C-10, H-5, H-6), 1 Isosorbide-5-Nitrae-dibasic phenyl ring (C-1' ~ C-6'；H-2',6'
And H-3', 5'), 1α,β- unsaturated carbonyl (C-2, C-3, C-4, H-3), 1 hydroxypropyl (C-1'' ~ C-3'', H2-1''~H2-
3''), two methoxyl groups (d C56.3 q and 56.0 q,d H3.80 s and 3.78 are s).According to typical 2 phenyl ring,α,β- no
Saturation carbonyl and double bond signal, it is flavone compound that can speculate the compound.According to H-3 and C-2, C-4, C-10, C-1 ', H-
5 and C-4, C-9, C-10, H-8 and C-6, C-7, C-9, C-10, and H-2 ', 6 ' is related to C-2 HMBC（Such as Fig. 3）One can be entered
Step confirms that compound is flavonoid structure.
After the parent of compound determines, remaining substituent, hydroxypropyl and methoxyl group can be considered the substituent on flavones.Change
In the HMBC spectrums of compound（Such as Fig. 3）Can be observed two methoxyl group hydrogen (d H3.80 and 3.78) HMBC phases with C-6 and C-4'
Close, can speculate that two methoxyl groups are substituted in C-6 and C-4' positions respectively；According to H2-1'' (d H 2.72) and C-6, C-7, C-8, H2-
2'' (d H1.92) and C-7, and H-8 (d H 6.81) it is related to C-1'' HMBC, it can be verified that hydroxypropyl is substituted in C-7 positions.
In addition proton signal on typical phenyl ring [H-5,d H7.16 s；H-8,d H 6.81 s, H-2 ', 6 ',d H 7.76 (d) 8.8；
H-3 ', 5 ',d H6.85 (t) 8.8] also the A rings of susceptible of proof chromocor compound of the present invention substitute for 6,7- positions two, B rings are 4'-
Position is monosubstituted.So far, the structure of compound is determined, Compound nomenclature is：6,4 '-dimethoxy -7- (3- hydroxypropyls)-Huang
Ketone.
Infrared, the ultraviolet and mass spectrometric data of compound：Purple light composes (methanol),λ max (log ε) 362 (3.74)、263
(3.78)、210 (4.22)；Infrared spectrum (pressing potassium bromide troche)：ν max 3416、2863、1665、1612、1562、1449、
1162、1257、1136、1050cm-1；1H and13C NMR data (500 and 125 MHz, solvent CDCl3), it is shown in Table -1；Just
Ion mode ESIMSm/z 363 [M+Na]+；Positive ion mode HRESIMSm/z 363.1202 [M+Na]+(calculated value
363.1208, C20H20NaO5)。
The compound of table 11H NMR and13C NMR data (CDCl3)
The third object of the present invention is achieved in that described flavone compound in resisting tobacco mosaic virus medicine is prepared
Application.
The compounds of this invention is separated first, is determined by nuclear magnetic resonance and measuring method of mass spectrum as flavones
Class compound, and characterize its concrete structure.Through the experiment to resisting tobacco mosaic virus, its relative inhibition reaches 31.8%, tool
There is good activity of resisting tobacco mosaic virus, close to the relative inhibition of positive reference substance Nanning mycin（33.8%）.Result above
The compound for disclosing the present invention has good application prospect in resisting tobacco mosaic virus medicine is prepared.The compounds of this invention knot
The simple activity of structure is good, can be as the guiding compound of resisting tobacco mosaic virus medicine.
Brief description of the drawings
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 related.
Embodiment
With reference to embodiment and accompanying drawing, the present invention is further illustrated, but the present invention is not subject in any way
Limitation, based on present invention teach that any conversion or replacement made, belong to protection scope of the present invention.
Flavone compound of the present invention is isolated from short leaf Cassia, and its molecular formula is C20H20O5, compound
It is named as：6,4 '-dimethoxy -7- (3- hydroxypropyls)-flavones, English are entitled：6,4'-dimethoxy-7-(3-
Hydroxypropyl)-flavone, there are following structures：
。
The preparation method of flavone compound of the present invention, be with short leaf Cassia (Cassia leschenaultiana DC.) it is raw material, extracted through medicinal extract, silica gel column chromatography, high pressure liquid chromatography separate and gel filtration chromatography
Step is prepared, and specifically includes following steps：
A, medicinal extract extracts：Take the short leaf Cassia of raw material (Cassia leschenaultiana DC.), using whole plant as raw material or
Segment is crushed and be cut into, the organic solvent that raw material weighs 2 ~ 4 times of mass concentration 70 ~ 100% is added, 24 ~ 72h of soak extraction, carries
Take 3 ~ 5 times, merge extract solution, filtering and concentrating into medicinal extract；
B, silica gel column chromatography：Medicinal extract carries out silica gel column chromatography with 150 ~ 200 mesh silica gel dry column-packings of 2 ~ 5 times of medicinal extract weight, with
Volume proportion is 20:1~5:5 chloroform-methanol carries out gradient elution, merges identical part, collects each several part eluent
And concentrate；
C, high pressure liquid chromatography separates：By the 8 of eluent:2 parts are further isolated and purified to obtain target with high pressure liquid chromatography
Thing flavone compound.
Organic solvent described in step A is the methanol of mass percentage concentration 80 ~ 100%, mass percentage concentration 80 ~ 100%
Ethanol or mass percentage concentration 70 ~ 100% acetone.
Also include silica gel mixed sample step before silica gel column chromatography.
Described silica gel mixed sample is to use medicinal extract after pure methanol, straight alcohol or the pure acetone dissolving with 1.5 ~ 3 times of medicinal extract weight
80 ~ 100 mesh silica gel mixed samples of 0.8 ~ 1.5 times of weight.
The volume ratio of chloroform-methanol is 20 in step B:1、9:1、8:2、7:3、6:4 and 5:5.
It is using the mm of 21.2 mm × 250 5 that step C mesohigh liquid chromatogram, which isolates and purifies,μM C18Chromatographic column, stream
Speed is 20 mL/min, and mobile phase is 60% methanol, and UV-detector Detection wavelength is 362 nm, each sample introduction 200μL, receive
Collect 31.6 min chromatographic peak, be evaporated after repeatedly adding up.
After high pressure liquid chromatography purification procedures, gained compound is dissolved with pure methanol again, then using pure methanol as stream
Dynamic phase, is separated with gel filtration chromatography, further to isolate and purify.
The application of flavone compound of the present invention is that described flavone compound is preparing resisting tobacco mosaic disease
Application in cytotoxic drug.
So that case is embodied, the present invention will be further described below：
Embodiment 1
The short kg of leaf Cassia sample 2.0 is crushed and is extracted 5 times with 95% methanol, often in Yuanjiang County of Yunnan by short leaf Cassia sample source
Secondary extraction 24h, extract solution merge, and filtering, are concentrated under reduced pressure into medicinal extract, obtain the g of medicinal extract 98.Pure first of the medicinal extract weight than 2.0 times of amounts
Silica gel column chromatography is carried out, is matched somebody with somebody with volume with the 120 g thick silica gel mixed sample of 80 mesh, 0.6 kg 160 mesh silica gel dress post after alcohol dissolving
Than for 20:1、9:1、8:2、7:3、6:4、5:5 chloroform-methanol gradient elution, TLC monitorings merge identical part, obtain 6
Part, wherein volume proportion are 8:2 chloroform-methanol elution fraction pacifies the prompt preparative high-performance liquid chromatographic of logical sequence 1,100 half separation,
Using 60% methanol as mobile phase, and Zorbax SB-C18 (21.2 × 250 mm, 5μm) to prepare post be stationary phase, flow velocity is
20 ml/min, UV-detector Detection wavelength are 362 nm, each sample introduction 200μL, 31.6 min chromatographic peak is collected, 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 gels
Column chromatography for separation, produce the noval chemical compound.
Embodiment 2
Short leaf Cassia sample source samples 4.0 kg choppings in Lincang, by short leaf Cassia, extracts 4 times with 95% ethanol, often
Secondary extraction 48h, extract solution merge, and filtering, are concentrated under reduced pressure into medicinal extract, obtain the g of medicinal extract 181.Medicinal extract weight is measured pure than 2.0 times
Silica gel column chromatography is carried out, is used body with the 200 g thick silica gel mixed sample of 100 mesh, 1.0 kg 200 mesh silica gel dress post after methanol dissolving
Product proportioning is 20:1、9:1、8:2、7:3、6:4、5:5 chloroform-methanol gradient elution, TLC monitorings merge identical part, obtained
To 6 parts, wherein volume proportion is 8:2 chloroform-acetone elution fraction pacifies the prompt preparative high-performance liquid chromatographic of logical sequence 1,100 half
Separation, using 60% methanol as mobile phase, Zorbax SB-C18 (21.2 × 250 mm, 5μM) it is stationary phase to prepare post,
Flow velocity is 20 ml/min, and UV-detector Detection wavelength is 362 nm, each sample introduction 200μL, collect 31.6 min chromatogram
Peak, it is evaporated after repeatedly adding up；Products therefrom is dissolved with pure methanol again, then using pure methanol as mobile phase, with Sephadex LH-
20 gel filtration chromatographies separate, and produce the noval chemical compound.
Embodiment 3
Short leaf Cassia sample source crushes the short kg of leaf Cassia sample 6, with 80% acetone ultrasonic extraction 3 in Dali
It is secondary, 72h is extracted every time, and extract solution merges, and filtering, is concentrated under reduced pressure into medicinal extract, obtains the g of medicinal extract 305.Medicinal extract than 1.6 times amounts of weight
Pure methanol dissolving after use 320 g the thick silica gel mixed sample of 90 mesh, 1.6 kg 180 mesh silica gel dress post carry out silica gel column chromatography, use
Volume proportion is 20:1、9:1、8:2、7:3、6:4、5:5 chloroform-methanol gradient elution, TLC monitorings merge identical part,
6 parts are obtained, wherein volume proportion is 8:2 chloroform-acetone elution fraction pacifies prompt logical sequence 1,100 half and prepares high-efficient liquid phase color
Spectrum separation, using 60% methanol as mobile phase, Zorbax SB-C18 (21.2 × 250 mm, 5μM) post is prepared to fix
Phase, flow velocity are 20 ml/min, and UV-detector Detection wavelength is 362 nm, each sample introduction 200μL, collect 31.6 min color
Spectral peak, it is evaporated after repeatedly adding up；Products therefrom is dissolved with pure methanol again, then using pure methanol as mobile phase, uses Sephadex
LH-20 gel filtration chromatographies separate, and produce the noval chemical compound.
Embodiment 4
Compound prepared by Example 1, is orange colour jelly.
Compound is orange-yellow jelly, and HRESI-MS shows that its quasi-molecular ion peak is 363.1202 [M+Na]+(meter
Calculation value 363.1208), with reference to1H NMR and DEPT spectrum determine that its molecular formula is C20H20O5, degree of unsaturation 11.
Hydroxyl (3416 cm are shown in infrared spectrum-1), carbonyl (1665 cm-1) and aromatic ring (1612,1562 and 1449
cm-1) resonance absorbing peak.And ultraviolet spectra there may be in 210,263,362 nm have absorption maximum to also illustrate that compound
Aromatic ring structure.
Compound1H and13C H NMR spectroscopies（Such as table 1, Fig. 1 and Fig. 2）Show that it contains 20 carbon and 20 hydrogen, including 1
1,2,4,5- quaternary phenyl ring (C-5 ~ C-10, H-5, H-6), 1 Isosorbide-5-Nitrae-dibasic phenyl ring (C-1' ~ C-6'；H-2',6'
And H-3', 5'), 1α,β- unsaturated carbonyl (C-2, C-3, C-4, H-3), 1 hydroxypropyl (C-1'' ~ C-3'', H2-1''~H2-
3''), two methoxyl groups (d C56.3 q and 56.0 q,d H3.80 s and 3.78 are s).According to typical 2 phenyl ring,α,β- no
Saturation carbonyl and double bond signal, it is flavone compound that can speculate the compound.According to H-3 and C-2, C-4, C-10, C-1 ', H-
5 and C-4, C-9, C-10, H-8 and C-6, C-7, C-9, C-10, and H-2 ', 6 ' is related to C-2 HMBC（Such as Fig. 3）One can be entered
Step confirms that compound is flavonoid structure.
After the parent of compound determines, remaining substituent, hydroxypropyl and methoxyl group can be considered the substituent on flavones.Change
In the HMBC spectrums of compound（Such as Fig. 3）Can be observed two methoxyl group hydrogen (d H3.80 and 3.78) HMBC phases with C-6 and C-4'
Close, can speculate that two methoxyl groups are substituted in C-6 and C-4' positions respectively；According to H2-1'' (d H 2.72) and C-6, C-7, C-8, H2-
2'' (d H1.92) and C-7, and H-8 (d H 6.81) it is related to C-1'' HMBC, it can be verified that hydroxypropyl is substituted in C-7 positions.
In addition proton signal on typical phenyl ring [H-5,d H7.16 s；H-8,d H 6.81 s, H-2 ', 6 ',d H 7.76 (d) 8.8；
H-3 ', 5 ',d H6.85 (t) 8.8] also the A rings of susceptible of proof chromocor compound of the present invention substitute for 6,7- positions two, B rings are 4'-
Position is monosubstituted.So far, the structure of compound is determined, Compound nomenclature is：6,4 '-dimethoxy -7- (3- hydroxypropyls)-Huang
Ketone.
Embodiment 5
Compound prepared by Example 2, is orange colour jelly.Assay method is same as Example 4, confirms that embodiment 2 is made
Standby compound is described flavone compound --- 6,4'- dimethoxys -7- (3- hydroxypropyls)-flavones.
Embodiment 6
Compound prepared by Example 3, is orange colour jelly.Assay method is same as Example 4, confirms that embodiment 3 is made
Standby compound is described flavone compound --- 6,4'- dimethoxys -7- (3- hydroxypropyls)-flavones.
Embodiment 7
Any flavone compound prepared by Example 1 ~ 3 carries out activity of resisting tobacco mosaic virus experiment, and test situation is as follows：
Using half leaf method, resisting tobacco mosaic virus is carried out to the compounds of this invention when the mass concentration of medicament is 50 mg/L
Determination of activity.On the plant of 5~6 age flue-cured tobaccos, the blade (leaf row is normal, disease-free no worm) suitable for test is chosen, first by leaf
Piece uniformly sprinkles fine emery powder, with writing brush by standby tobacco mosaic virus (TMV) source (3.0 × 10-3) be uniformly put on sprinkled with diamond dust
On blade, connect after the blade of all middle choosings after poison terminates, be immediately placed in the culture dish for fill decoction and handle 20 min, take out,
The globule and decoction on blade are wiped, the recovery of two and half leaves is emitted on and is covered with the glass jar of toilet paper moisturizing, and covers glass
Lid, temperature control (23 ± 2) DEG C are placed on greenhouse natural light irradiation, 2~3 d be visible withered spot each processing set second half leaf as
Control, it is additionally provided with 1 group of processing for commodity Ningnanmycin as a comparison, presses formula and calculate relative inhibition.
XI%=(CK-T)/CK × 100%
X：Relative inhibition (%), CK：The withered spot number (individual) that half in clear water connects malicious leaf is soaked in, T is soaked in half in decoction
Connect the withered spot number (individual) of malicious leaf.
As a result the relative inhibition of bright compound is 31.8%, close to the relative inhibition of control Ningnanmycin
33.8%, illustrate that compound has preferable activity of resisting tobacco mosaic virus.
Claims (9)
1. a kind of flavone compound, it is characterised in that the flavone compound is isolated, its point from short leaf Cassia
Minor is C20H20O5, Compound nomenclature is：6,4 '-dimethoxy -7- (3- hydroxypropyls)-flavones, English are entitled：6,4'-
Dimethoxy-7- (3- hydroxypropyl)-flavone, has following structures：
。
2. the preparation method of the flavone compound described in a kind of claim 1, it is characterised in that be with short leaf Cassia
(Cassia leschenaultiana DC.) it is raw material, extracted through medicinal extract, silica gel column chromatography, high pressure liquid chromatography separate and solidifying
Plastic column chromatography step is prepared, and specifically includes following steps：
A, medicinal extract extracts：Take the short leaf Cassia of raw material (Cassia leschenaultiana DC.), using whole plant as raw material or
Segment is crushed and be cut into, the organic solvent that raw material weighs 2 ~ 4 times of mass concentration 70 ~ 100% is added, 24 ~ 72h of soak extraction, carries
Take 3 ~ 5 times, merge extract solution, filtering and concentrating into medicinal extract；
B, silica gel column chromatography：Medicinal extract carries out silica gel column chromatography with 150 ~ 200 mesh silica gel dry column-packings of 2 ~ 5 times of medicinal extract weight, with
Volume proportion is 20:1~5:5 chloroform-methanol carries out gradient elution, merges identical part, collects each several part eluent
And concentrate；
C, high pressure liquid chromatography separates：By the 8 of eluent:2 parts are further isolated and purified to obtain target with high pressure liquid chromatography
Thing flavone compound.
3. preparation method according to claim 2, it is characterised in that the organic solvent described in step A is dense for quality percentage
Methanol, the ethanol of mass percentage concentration 80 ~ 100% or the acetone of mass percentage concentration 70 ~ 100% of degree 80 ~ 100%.
4. preparation method according to claim 2, it is characterised in that also include silica gel mixed sample step before silica gel column chromatography.
5. preparation method according to claim 4, it is characterised in that described silica gel mixed sample is to use 1.5 ~ 3 times of medicinal extract weight
Pure methanol, straight alcohol or pure acetone dissolving after use 0.8 ~ 1.5 times of medicinal extract weight 80 ~ 100 mesh silica gel mixed samples.
6. preparation method according to claim 2, it is characterised in that the volume ratio of chloroform-methanol is 20 in step B:
1、9:1、8:2、7:3、6:4 and 5:5.
7. preparation method according to claim 2, it is characterised in that it is to use that step C mesohigh liquid chromatogram, which isolates and purifies,
21.2 mm × 250 mm, 5μM C18Chromatographic column, flow velocity are 20 mL/min, and mobile phase is 60% methanol, UV-detector
Detection wavelength is 362 nm, each sample introduction 200μL, 31.6 min chromatographic peak is collected, is evaporated after repeatedly adding up.
8. preparation method according to claim 2, it is characterised in that after high pressure liquid chromatography purification procedures, gained
Compound is dissolved with pure methanol again, then using pure methanol as mobile phase, is separated with gel filtration chromatography, further to isolate and purify.
9. the application of the flavone compound described in a kind of claim 1, it is characterised in that described flavone compound is being made
Application in standby resisting tobacco mosaic virus medicine.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111574492A (en) * | 2020-06-08 | 2020-08-25 | 云南民族大学 | Anti-tobacco mosaic virus compound, preparation method and application thereof, and tobacco mosaic virus inhibitor containing compound |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105017198A (en) * | 2015-07-02 | 2015-11-04 | 云南中烟工业有限责任公司 | Preparation of isobutylene flavonoids in sun-cured tobacco and application of isobutylene flavonoids for resisting tobacco mosaic virus |
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2017
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105017198A (en) * | 2015-07-02 | 2015-11-04 | 云南中烟工业有限责任公司 | Preparation of isobutylene flavonoids in sun-cured tobacco and application of isobutylene flavonoids for resisting tobacco mosaic virus |
Non-Patent Citations (1)
| Title |
|---|
| M. ZHOU ET AL.: "Flavones from Cassia siamea and their anti-tobacco mosaic virus activity", 《JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111574492A (en) * | 2020-06-08 | 2020-08-25 | 云南民族大学 | Anti-tobacco mosaic virus compound, preparation method and application thereof, and tobacco mosaic virus inhibitor containing compound |
| CN111574492B (en) * | 2020-06-08 | 2022-05-20 | 云南民族大学 | Compound for resisting tobacco mosaic virus, preparation method and application thereof, and tobacco mosaic virus inhibitor containing compound |
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| CN107445934B (en) | 2020-05-19 |
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