CN105777677B - A kind of furancarboxylic acid class compound and its preparation method and application - Google Patents
A kind of furancarboxylic acid class compound and its preparation method and application Download PDFInfo
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- CN105777677B CN105777677B CN201610176269.4A CN201610176269A CN105777677B CN 105777677 B CN105777677 B CN 105777677B CN 201610176269 A CN201610176269 A CN 201610176269A CN 105777677 B CN105777677 B CN 105777677B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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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
- A01N43/06—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 five-membered rings
- A01N43/08—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 five-membered rings with oxygen as the ring hetero atom
Abstract
The invention discloses a kind of furancarboxylic acid class compound and its preparation method and application, the furancarboxylic acid class compound is isolated from cured tobacco leaf, and its molecular formula is C14H14O5It is named as the formic acid of 5 (the ＇ aminomethyl phenyls of 3 ＇ hydroxyls, 4 ＇ methoxyl groups 5) 3 methylfuran 2, English entitled [the carboxylic acid of 5 (the ＇ methylphenyl of 3 ＇ hydroxy, 4 ＇ methoxy 5) 3 methyl furan 2], with following structures：The furancarboxylic acid class compounds process for production thereof is using cured tobacco leaf as raw material, is extracted through medicinal extract, silica gel column chromatography, high pressure liquid chromatography separating step, is specially：By sample comminution, extraction, filtering, concentration, chromatograph, elution, the 1 of eluent:1 part is isolated and purified with high pressure liquid chromatography produces described furancarboxylic acid class compound.The furancarboxylic acid class compound has good inhibiting effect through active testing to tobacco mosaic virus (TMV).The compounds of this invention is simple in construction, activity preferably, can as resisting tobacco mosaic virus medicine guiding compound.
Description
Technical field
The invention belongs to technical field of tobacco chemistry, and in particular to a kind of to extract obtained furancarboxylic acid first from tobacco
Class compound and its preparation method and application.
Background technology
Tobacco is the plant of chemical composition complexity the most in the world, and secondary metabolite enriches very much, according to nineteen eighty-two Dube
Reported with Green etc., the chemical composition identified in tobacco was just more than 2549 kinds, by 2008, Rodgman and perfetti
Report, the compound that is found in tobacco, tobacco and cigarette smoke sum is about 8700 kinds.At present, people
The monomer chemistries material come the just kind more than 3000 is identified from tobacco, and also many compositions are not yet identified and.Cigarette
Grass can also therefrom extract a variety of chemical compositions for having a value in addition to cigarette smoking purposes is mainly used in, and therefrom find have out
Send out the guiding compound of value.
Furfuran compound exists in many natural plants, and with multiple biological activities.According to the literature, such
Compound has antitumor, and anti-oxidant, Ca2+ influx retardance, angiotensin-ii receptor antagonism, adenosine A l receptor antagonists resist true
The pharmacological actions such as bacterium, antibacterial activity and platelet aggregation antagonism.Because Benzofurans compound has the pharmacology of such wide spectrum
Activity, domestic and international researcher is conducted in-depth research to such compound, except finding such chemical combination beyond the region of objective existence from natural products,
The compound with more excellent pharmacological activity is also obtained by structural modification., can in order to study the structure-activity relationship of this kind of compound
More furfuran compounds are further researched and developed, effective lead compound and active group is therefrom found.The present invention
Related report is not yet seen in a kind of isolated new furancarboxylic acid class compound from Yunnan Flue-cured Tobacco tobacco leaf, the compound
Road, it is worth mentioning at this point that the compound has significant resisting tobacco mosaic disease virus activity.
The content of the invention
The first object of the present invention is to provide a kind of structure novel furancarboxylic acid class compound；Second purpose is to carry
For the preparation method of the furancarboxylic acid class compound；3rd purpose is that provide the furancarboxylic acid class compound resists in preparation
Application in tobacco mosaic disease cytotoxic drug.
The first object of the present invention be achieved in that the furancarboxylic acid class compound be it is isolated from tobacco leaf,
Its molecular formula is C14H14O5, with following structures：
The compound is named as 5- (the 3 ＇-＇ of hydroxyl-4-＇ of methoxyl group-5-aminomethyl phenyl)-3- methyl-ribofuranosyl-2- formic acid,
Entitled [5- (3 ＇-hydroxy-4 ＇-methoxy-5 ＇-the methylphenyl) -3-methyl-furan-2- of English
Carboxylic acid], it is light yellow gum thing.
The second object of the present invention be achieved in that the furancarboxylic acid class compound be using cured tobacco leaf as raw material,
Extracted through medicinal extract, silica gel column chromatography, high pressure liquid chromatography separating step, be specially：
A. medicinal extract is extracted:Using tobacco leaf as raw material, segment is crushed or be cut into tobacco leaf, is soaked with 60 ~ 100% organic solvent
And extract 3 ~ 5 times, each 24h ~ 72h, merge extract solution, filtering, be concentrated under reduced pressure into medicinal extract；
B. silica gel column chromatography：After medicinal extract organic solvent dissolves, 80 ~ 100 mesh silica gel with medicinal extract weight than 0.8 ~ 1.2 times
Sample is mixed, then 160 ~ 300 mesh silica gel dry column-packings measured with medicinal extract weight than 2 ~ 4 times carry out silica gel column chromatography；Matched somebody with somebody with volume for 1:0
~1:2 chloroform-acetone solution carries out gradient elution, collects each several part eluent and concentrates, merges identical part；
C. high pressure liquid chromatography is separated：The 1 of step B eluent:1 part is further isolated and purified i.e. with high pressure liquid chromatography
Obtain described furancarboxylic acid class compound.
The structure of furancarboxylic acid class compound prepared by method described above is to determine to come by the following method：
The compounds of this invention is light yellow gum thing；Ultraviolet spectra (solvent is methanol), λ max (log ε) 306
(2.70)、248 (3.35)、210 (3.74)；Infrared spectrum (pressing potassium bromide troche) ν max 3418,3419,3023,2942,
1687、1613、1582、1240、1120、1048 cm-1；High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak m/z
[285.0746 M+Na]+(calculated value 285.0739).With reference to1H and13C H NMR spectroscopies provide a molecular formula C14H14O5, it is unsaturated
Spend for 8.There are-OH (3418 cm-1) ,-CO2H (br. 3023 from the ir data confirmation compound of compound 1
), cm-1-CO2 (1687 cm-1) and aromatic ring (1613 and 1582 cm-1) functional group.The proton nmr spectra card of compound
Exist in realification compound 1 methoxyl group (s of δ H 3.86), 1 carboxyl (δ H 10.05), 3 fragrant methines (s of δ H 6.21,
6.53 s and 6.68 s), two methyl (s of δ H 1.85 and 2.39 s) and 1 phenolic hydroxyl group (s of δ H 10.68).Its nuclear-magnetism is total to
The carbon that shakes spectrum also confirms that in compound there is carboxyl carbon (s of δ C 167.3), two methyl carbon (q of δ C 9.0 and 18.2 q),
One methoxyl group carbon (q of δ C 61.4), 3 fragrant methine carbons (d of δ C 105.8,111.3 d and 124.1 d), 4 sp2
The quaternary carbon (s of δ C 162.7,156.9 s, 146.1 s and 155.2 s) of oxidation, and fragrant quaternary carbon (the δ C of 3 sp2
103.0 s, 125.4 s and 127.2 are s).According to H3-13 (δ H 1.85) and C-2 (δ C 162.7), C-3 (δ C
103.0), C-4 (δ C 105.8) and C-12 (δ C 167.3), H-4 (δ H 6.21) and C-2 (δ C 162.7), C-3 (δ
C 103.0), C-5 (δ C 156.9), and (CO2H, δ H 10.05) related to C-2 (δ C 162.7) HMBC
(figure -3) confirms there is 3- methyl-ribofuranosyl formic acid structures in compound.Further from H-4 (δ H 6.21) and C-6 (δ C
125.4), H-7 (δ H 6.53), H-11 (δ H 6.68) confirmation related to C-5 (δ C 156.9) HMBC has phenyl ring to be substituted in
The C-5 positions of furan nucleus.The position of other substituents, another 1 methyl be substituted in C-10 can by H3-14 (δ H 2.39) and
C-9 (δ C 152.5), C-10 (δ C 127.2) are related to C-11 (δ C 124.1) HMBC to be confirmed；Methoxy substitution exists
C-9 can be determined by methoxyl group hydrogen (δ H 3.86) is related to C-9 (δ C 152.5) HMBC；Phenolic hydroxyl group is substituted in C-8
Can be by phenolic hydroxyl group hydrogen (δ H 10.68) and C-7 (δ C 111.3), C-8 (δ C 146.1) and C-9 (δ C 152.5)
HMBC correlations are confirmed.So far the structure of compound is determined, and is named as the 5- (3 ＇-＇ of hydroxyl-4-＇ of methoxyl group-5-first
Base phenyl) -3- methyl-ribofuranosyl -2- formic acid.
The compound of table -1.1H NMR and13C NMR data (C5D5N)
The third object of the present invention be achieved in that will the furancarboxylic acid class compound be applied to anti-Tobacco mosaic
The preparation of virus drugs.
The compounds of this invention is separated first, and furans first is defined as by nuclear magnetic resonance and measuring method of mass spectrum
Acid compounds, and characterize its concrete structure.Through the experiment to resisting tobacco mosaic virus, its relative inhibition surpasses up to 36.2%
Cross the relative inhibition of positive reference substance Ningnanmycin（31.5%）, with good activity of resisting tobacco mosaic virus.The present inventionization
Compound it is simple in construction activity preferably, can as resisting tobacco mosaic virus medicine guiding compound, before good application
Scape.
Brief description of the drawings
Fig. 1 is the carbon-13 nmr spectra of furancarboxylic acid class compound of the present invention（13C NMR）；
Fig. 2 is the proton nmr spectra of furancarboxylic acid class compound of the present invention（1H NMR）；
Fig. 3 is related for the main HMBC of furancarboxylic acid class compound of the present invention.
Embodiment
With reference to embodiment and accompanying drawing, the present invention is described in further detail, but not in any way to the present invention
It is any limitation as, based on present invention teach that any conversion or improvement made, each fall within protection scope of the present invention.
Furancarboxylic acid class compound of the present invention, is isolated from cured tobacco leaf, its molecular formula is C14H14O5, tool
There are following structures：
5- (the 3 ＇-＇ of hydroxyl-4-＇ of methoxyl group-5-aminomethyl phenyl)-3- methyl-ribofuranosyl-2- formic acid is named as, English is entitled
[5- (3 ＇-hydroxy-4 ＇-methoxy-5 ＇-methylphenyl) -3-methyl-furan-2-carboxylic acid].
The preparation method of furancarboxylic acid class compound of the present invention, is using cured tobacco leaf as raw material, is extracted through medicinal extract, silicon
Plastic column chromatography, high pressure liquid chromatography separating step, be specially：
A. medicinal extract is extracted:Using tobacco leaf as raw material, segment is crushed or be cut into tobacco leaf, is soaked with 60 ~ 100% organic solvent
And extract 3 ~ 5 times, each 24h ~ 72h, merge extract solution, filtering, be concentrated under reduced pressure into medicinal extract；
B. silica gel column chromatography：After medicinal extract organic solvent dissolves, 80 ~ 100 mesh silica gel with medicinal extract weight than 0.8 ~ 1.2 times
Sample is mixed, then 160 ~ 300 mesh silica gel dry column-packings measured with medicinal extract weight than 2 ~ 4 times carry out silica gel column chromatography；Matched somebody with somebody with volume for 1:0
~1:2 chloroform-acetone solution carries out gradient elution, collects each several part eluent and concentrates, merges identical part；
C. high pressure liquid chromatography is separated：The 1 of step B eluent:1 part is further isolated and purified i.e. with high pressure liquid chromatography
Obtain described furancarboxylic acid class compound.
Organic solvent is any one in methanol, ethanol, acetone in the step A.
The weight ratio of organic solvent and tobacco leaf is 2 ~ 4 in the step A:1.
Organic solvent is pure methanol, straight alcohol or pure acetone of the medicinal extract weight than 1.5 ~ 3 times of amounts in the step B.
Chloroform-acetone solution volume proportion in the step B is 1:0、20:1、9:1、8:2、7:3、6:4、1:1 and 1:
2。
It is to use 21.2mm × 250mm, 5 that the step C mesohigh liquid chromatogram, which is isolated and purified,μM C18Chromatographic column, flow velocity
For 20mL/min, mobile phase is 30% methanol, and UV-detector Detection wavelength is 306nm, each sample introduction 200μL, is collected
19.5min chromatographic peak, is evaporated after repeatedly adding up.
The step C mesohigh liquid chromatogram isolate and purify after material again with pure methanol dissolve, then using pure methanol as
Mobile phase, is separated with gel filtration chromatography, further to isolate and purify.
Application of the furancarboxylic acid class compound of the present invention in resisting tobacco mosaic virus medicine is prepared.
The present invention is raw materials used not to be limited by area and kind, the present invention can be realized, below with Yunnan
The raw tobacco material of cigarette industry Co., Ltd different sources, the present invention will be further described：
Embodiment 1
Tobacco sample derives from Yunnan Yuxi, and kind is Yuxi K326.Take tobacco leaf 2.0kg to crush, extracted with 95% methanol
5 times, 24h is extracted every time, extract solution merges, filtering is concentrated under reduced pressure into medicinal extract, obtains medicinal extract 105g.Medicinal extract than 2.0 times amounts of weight
Pure methanol dissolving after use 120g the thick silica gel mixed sample of 100 mesh, 0.6kg 160 mesh silica gel dress post carry out silica gel column chromatography, use body
Product proportioning is 1:0、20:1、9:1、8:2、7:3、6:4、1:1、1:2 chloroform-acetone gradient elution, TLC monitorings merge identical
Part, obtains 8 parts, wherein volume proportion is 1:1 chloroform-acetone elution fraction prepares efficient liquid with the prompt logical sequence 1,100 half of peace
Phase chromatographic isolation, using 30% methanol as mobile phase, it is fixation that Zorbax SB-C18 (21.2 × 250mm, 5 μm), which prepare post,
Phase, flow velocity is 20ml/min, and UV-detector Detection wavelength is 306 nm, each μ L of sample introduction 200, collects 19.5min chromatogram
Peak, 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 are separated, and produce the noval chemical compound.
Embodiment 2
Tobacco sample derives from Dali, and kind is cloud and mist 200.Take tobacco leaf 3.5kg to shred, 4 are extracted with 95% ethanol
It is secondary, 48h is extracted every time, extract solution merges, filtering is concentrated under reduced pressure into medicinal extract, obtains the g of medicinal extract 250.Medicinal extract than 2.0 times amounts of weight
Pure methanol dissolving after use 250g the thick silica gel mixed sample of 80 mesh, 1.2kg 200 mesh silica gel dress post carry out silica gel column chromatography, use body
Product proportioning is 1:0、20:1、9:1、8:2、7:3、6:4、1:1、1:2 chloroform-acetone gradient elution, TLC monitorings merge identical
Part, obtains 8 parts, wherein volume proportion is 1:1 chloroform-acetone elution fraction prepares efficient liquid with the prompt logical sequence 1,100 half of peace
Phase chromatographic isolation, using 30% methanol as mobile phase, it is fixation that Zorbax SB-C18 (21.2 × 250mm, 5 μm), which prepare post,
Phase, flow velocity is 20ml/min, and UV-detector Detection wavelength is 306nm, each μ L of sample introduction 200, collects 19.5 min chromatogram
Peak, 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 are separated, and produce the noval chemical compound.
Embodiment 3
Tobacco sample derives from Kunming, Yunnan, and kind is the big gold dollar of safflower.Take tobacco leaf 5kg to crush, use super with 75% acetone
Sound is extracted 3 times, and 72h is extracted every time, and extract solution merges, and filtering is concentrated under reduced pressure into medicinal extract, obtains medicinal extract 380g.Medicinal extract weight ratio
The 400g thick silica gel mixed sample of 90 mesh is used after the pure methanol dissolving of 1.6 times of amounts, 2.4 kg 180 mesh silica gel dress post carries out silica gel column layer
Analysis, is 1 with volume proportion:0、20:1、9:1、8:2、7:3、6:4、1:1、1:2 chloroform-acetone gradient elution, TLC monitorings are closed
And identical part, 8 parts are obtained, wherein volume proportion is 1:1 chloroform-acetone elution fraction is made with the prompt logical sequence 1,100 half of peace
Standby high performance liquid chromatography separation, using 30% methanol as mobile phase, prepared by Zorbax SB-C18 (21.2 × 250 mm, 5 μm)
Post is stationary phase, and flow velocity is 20ml/min, and UV-detector Detection wavelength is 306nm, each μ L of sample introduction 200, collects 19.5min
Chromatographic peak, it is repeatedly cumulative after be evaporated；Products therefrom is dissolved with pure methanol again, then using pure methanol as mobile phase, is used
Sephadex LH-20 gel filtration chromatographies are separated, and produce the noval chemical compound.
Embodiment 4
Compound prepared by Example 1, is light yellow gum thing；
Assay method is：With nuclear magnetic resonance, structure is identified with reference to other spectroscopic techniques.
The compounds of this invention is light yellow gum thing；Ultraviolet spectra (solvent is methanol), λ max (log ε) 306
(2.70)、248 (3.35)、210 (3.74)；Infrared spectrum (pressing potassium bromide troche) ν max 3418,3419,3023,2942,
1687、1613、1582、1240、1120、1048 cm-1；High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak m/z
285.0746 [M+Na]+(calculated value 285.0739).A molecular formula C is provided with reference to 1H and 13 C H NMR spectroscopies14H14O5, insatiable hunger
It is 8 with degree.There are-OH (3418 cm-1) ,-CO2H (br. from the ir data confirmation compound of compound 1
3023 cm-1) ,-CO2 (1687 cm-1) and aromatic ring (1613 and 1582 cm-1) functional group.The hydrogen nuclear magnetic resonance of compound
Spectrum confirms there are 1 methoxyl group (s of δ H 3.86), 1 carboxyl (δ H 10.05), 3 fragrant methine (δ H in compound
6.21 s, 6.53 s and 6.68 s), two methyl (s of δ H 1.85 and 2.39 s) and 1 phenolic hydroxyl group (s of δ H 10.68).
Its carbon-13 nmr spectra also confirms that in compound there is carboxyl carbon (s of δ C 167.3), two methyl carbon (q of δ C 9.0 and
18.2 q), a methoxyl group carbon (q of δ C 61.4), 3 fragrant methine carbon (d of δ C 105.8,111.3 d and 124.1
D), the quaternary carbon (s of δ C 162.7,156.9 s, 146.1 s and 155.2 s) of 4 sp2 oxidations, and 3 sp2 fragrance
Quaternary carbon (s of δ C 103.0,125.4 s and 127.2 s).According to H3-13 (δ H 1.85) and C-2 (δ C 162.7), C-
3 (δ C 103.0), C-4 (δ C 105.8) and C-12 (δ C 167.3), H-4 (δ H 6.21) and C-2 (δ C 162.7),
C-3 (δ C 103.0), C-5 (δ C 156.9), and (CO2H, δ H 10.05) and C-2 (δ C 162.7) HMBC phases
Closing (figure -3) confirms there is 3- methyl-ribofuranosyl formic acid structures in compound.Further from H-4 (δ H 6.21) and C-6 (δ
C 125.4), H-7 (δ H 6.53), H-11 (δ H 6.68) confirmation related to C-5 (δ C 156.9) HMBC have phenyl ring substitution
In the C-5 positions of furan nucleus.The position of other substituents, another 1 methyl is substituted in C-10 can be by H3-14 (δ H 2.39)
It is related to C-11 (δ C 124.1) HMBC to C-9 (δ C 152.5), C-10 (δ C 127.2) to confirm；Methoxyl group takes
In generation, can be determined in C-9 by methoxyl group hydrogen (δ H 3.86) is related to C-9 (δ C 152.5) HMBC；Phenolic hydroxyl group is substituted in
C-8 can be by phenolic hydroxyl group hydrogen (δ H 10.68) and C-7 (δ C 111.3), C-8 (δ C 146.1) and C-9 (δ C
152.5) HMBC correlations are confirmed.So far the structure of compound is determined, and is named as the 5- (3 ＇-＇ of hydroxyl-4-methoxy
The ＇ of base-5-aminomethyl phenyl)-3- methyl-ribofuranosyl-2- formic acid.
Embodiment 5
Compound prepared by Example 2, is light yellow gum thing.Assay method is same as Example 4, confirms to implement
Compound prepared by example 2 is the furancarboxylic acid class compound.
Embodiment 6
Compound prepared by Example 3, is light yellow gum thing.Assay method is same as Example 4, confirms to implement
Compound prepared by example 3 is the furancarboxylic acid class compound.
Embodiment 7
Furancarboxylic acid class compound prepared by Example 1 ~ 4 carries out activity of resisting tobacco mosaic virus experiment, tests feelings
Condition is as follows：
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 is determined.On the plant of 5 ~ 6 age flue-cured tobaccos, the blade (leaf row is normal, disease-free without 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 20min, take out, wipe
The globule and decoction on blade are removed, two and half leaves are restored and is emitted on and is covered with the glass jar of toilet paper moisturizing, and covers glass cover,
Temperature control (23 ± 2) DEG C, is placed on greenhouse natural light irradiation, and 2 ~ 3d is that each processing sets second half leaf as control to visible withered spot, separately
It is externally 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 decoction half
Piece connects the withered spot number (individual) of malicious leaf.
As a result the relative inhibition of bright compound is 36.2%, more than the relative inhibition 31.5% of control Ningnanmycin,
Illustrate that compound has good activity of resisting tobacco mosaic virus.
Claims (6)
1. a kind of furancarboxylic acid class compound, it is characterised in that the furancarboxylic acid class compound is separated from cured tobacco leaf
Arrive, its molecular formula is C14H14O5, with following structures：
The Compound nomenclature is：5- (the 3 ＇-＇ of hydroxyl-4-＇ of methoxyl group-5-aminomethyl phenyl)-3- methyl-ribofuranosyl-2- formic acid.
2. the preparation method of furancarboxylic acid class compound described in a kind of claim 1, it is characterised in that using cured tobacco leaf as raw material,
Extracted through medicinal extract, prepared by silica gel column chromatography, high pressure liquid chromatography separating step, be specially：
A. medicinal extract is extracted:Using tobacco leaf as raw material, tobacco leaf is crushed or segment is cut into, is soaked and is carried with 60 ~ 100% organic solvent
Take 3 ~ 5 times, each 24h ~ 72h, merge extract solution, filtering, be concentrated under reduced pressure into medicinal extract, organic solvent is in methanol, ethanol, acetone
Any one；
B. silica gel column chromatography：Medicinal extract organic solvent dissolves, and organic solvent is medicinal extract weight than the pure methanol, pure of 1.5 ~ 3 times of amounts
Ethanol or pure acetone；Then 80 ~ 100 mesh silica gel mixed samples of the medicinal extract weight than 0.8 ~ 1.2 times are used, then with medicinal extract weight than 2 ~ 4 times
160 ~ 300 mesh silica gel dry column-packings of amount carry out silica gel column chromatography；Matched somebody with somebody with volume for 1:0~1:2 chloroform-acetone solution is carried out
Gradient elution, collects each several part eluent and concentrates, merge identical part；
C. high pressure liquid chromatography is separated：The 1 of step B eluent:1 part is further isolated and purified with high pressure liquid chromatography, high pressure
It is to use 21.2mm × 250mm, 5 that liquid chromatogram, which is isolated and purified,μM C18Chromatographic column, flow velocity is 20mL/min, and mobile phase is 30%
Methanol, UV-detector Detection wavelength be 306nm, each sample introduction 200μL, collects 19.5min chromatographic peak, after repeatedly adding up
It is evaporated, produces the furancarboxylic acid class compound.
3. the preparation method of furancarboxylic acid class compound according to claim 2, it is characterised in that organic molten in the step A
The weight ratio of agent and tobacco leaf is 2 ~ 4:1.
4. the preparation method of furancarboxylic acid class compound according to claim 2, it is characterised in that the chlorine in the step B
Imitative-acetone soln volume proportion is 1:0、20:1、9:1、8:2、7:3、6:4、1:1 and 1:2.
5. the preparation method of furancarboxylic acid class compound according to claim 2, it is characterised in that the step C mesohigh liquid
Material after phase chromatographic separation and purification is dissolved with pure methanol again, then using pure methanol as mobile phase, is separated with gel filtration chromatography, with
Further isolate and purify.
6. application of the furancarboxylic acid class compound in resisting tobacco mosaic virus medicine is prepared described in a kind of claim 1.
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| CN105777677A (en) | 2016-07-20 |
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