CN105777677A - Furan-carboxylic acid compound as well as preparation method and application thereof - Google Patents
Furan-carboxylic acid compound as well as preparation method and application thereof Download PDFInfo
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- CN105777677A CN105777677A CN201610176269.4A CN201610176269A CN105777677A CN 105777677 A CN105777677 A CN 105777677A CN 201610176269 A CN201610176269 A CN 201610176269A CN 105777677 A CN105777677 A CN 105777677A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
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- 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
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Abstract
The invention discloses a furan-carboxylic acid compound as well as a preparation method and application thereof; the furan-carboxylic acid compound is obtained by being separated from flue-cured tobacco leaves, has a molecular formula of C14H14O5, is named as 6-(3'-hydroxy-4'-methoxy-5'-methyl phenyl)-3-methyl-furan-2-carboxylic acid in English, and has a structure described in the specification. The preparation method of the furan-carboxylic acid compound takes the flue-cured tobacco leaves as raw materials and comprises the steps such as extract extraction, silica gel column chromatography and high-pressure liquid chromatography separation; the preparation method concretely comprises the following steps: crushing a sample, extracting, filtering, concentrating, carrying out chromatography, eluting, and purifying the 1: 1 part of eluant by the high-pressure liquid chromatography separation to obtain the furan-carboxylic acid compound. An activity test proves that the furan-carboxylic acid compound has a good inhibiting effect for tobacco mosaic virus. The furan-carboxylic acid compound is simple in structure and better in activity, and can be used as a pilot compound of a tobacco mosaic virus-resistant medicine.
Description
Technical field
The invention belongs to technical field of tobacco chemistry, be specifically related to a kind of furancarboxylic acid compounds extracting first from tobacco and obtaining and its preparation method and application.
Background technology
Tobacco is the plant that chemical composition is the most complicated in the world, secondary metabolite is the abundantest, according to Dube and Green in 1982 etc., the chemical composition identified in tobacco is just more than 2549 kinds, by 2008, Rodgman and perfetti reports, the compound sum found in tobacco, tobacco and cigarette smoke is about 8700 kinds.At present, the monomer chemistries material that people identify out from tobacco is just more than kind more than 3000, and also has many compositions not yet to identify out.Tobacco, in addition to being mainly used in cigarette smoking purposes, also can therefrom be extracted the multiple chemical composition having value, therefrom be found to have the guiding compound of value of exploiting and utilizing.
Furfuran compound exists in a lot of natural plants, and has multiple biologically active.According to the literature, this compounds has antitumor, anti-oxidant, and Ca2+ influx blocks, angiotensin-ii receptor antagonism, adenosine A l receptor antagonist, the pharmacological action such as antimycotic, antibacterial activity and platelet aggregation antagonism.Owing to Benzofurans compound has the pharmacologically active of such wide spectrum, this compounds is conducted in-depth research by domestic and international researcher, in addition to finding this compounds from natural products, also obtains the compound with more excellent pharmacologically active through structural modification.In order to study the structure-activity relationship of this compounds, more furfuran compound can be researched and developed further, therefrom find effective lead compound and active group.The present invention is a kind of new furancarboxylic acid compounds of isolated from Yunnan Flue-cured Tobacco tobacco leaf, and this compound it is not yet seen relevant report, it is worth mentioning at this point that this compound has significant resisting tobacco mosaic disease virus activity.
Summary of the invention
The first object of the present invention is to provide the furancarboxylic acid compounds of a kind of novel structure；Second purpose is to provide the preparation method of described furancarboxylic acid compounds；3rd purpose is the application providing described furancarboxylic acid compounds in preparing resisting tobacco mosaic virus medicine.
The first object of the present invention is achieved in that described furancarboxylic acid compounds is isolated from tobacco leaf, and its molecular formula is C14H14O5, have a structure in which
Named 6-(3 ＇-hydroxyl-4 ＇-methoxyl group-5 ＇-aminomethyl phenyl)-3-methyl-ribofuranosyl-2-formic acid of this compound, English entitled [6-(3 ＇-hydroxy-4 ＇-methoxy-5 ＇-methylphenyl)-3-methyl-furan-2-carboxylic acid], for light yellow gum thing.
The second object of the present invention is achieved in that described furancarboxylic acid compounds is with cured tobacco leaf as raw material, through medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography separating step, particularly as follows:
A. medicinal extract extracts: with tobacco leaf as raw material, is pulverized by tobacco leaf or is cut into segment, soaks with the organic solvent of 60 ~ 100% and extract 3 ~ 5 times, and each 24 h～72 h merge extract, filtration, and reduced pressure concentration becomes medicinal extract；
B. silica gel column chromatography: after medicinal extract dissolves with organic solvent, with medicinal extract weight ratio 0.8～the 80 of 1.2 times～100 mesh silica gel mixed sample, then carry out silica gel column chromatography with 160～300 mesh silica gel dry column-packings of medicinal extract weight ratio 2～4 times amount；With volume join as 1:0 ~ chloroform-acetone solution of 1:2 carries out gradient elution, collect each several part eluent and also concentrate, merge identical part；
C. high pressure liquid chromatography separates: the 1:1 part of step B eluent i.e. obtains described furancarboxylic acid compounds with high pressure liquid chromatography is isolated and purified further.
The structure of furancarboxylic acid compounds prepared by method described above is to measure out by the following method:
The compounds of this invention is light yellow gum thing；Ultraviolet spectra (solvent is methyl alcohol), 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).In conjunction with1H and13C H NMR spectroscopy provides molecular formula C14H14O5, degree of unsaturation is 8.Confirm that compound has-OH (3418 cm-1), CO2H from the ir data of compound 1
(br. 3023 cm-1) ,-CO2 (1687 cm-1) and aromatic ring (1613 and 1582
Cm-1) functional group.The proton nmr spectra of compound confirms to exist in compound 1 methoxyl group (δ H 3.86 s), 1 carboxyl (δ H 10.05), 3 fragrant methines (δ H 6.21 s, 6.53 s and 6.68 s), two methyl (δ H 1.85 s and 2.39 s) and 1 phenolic hydroxyl group (δ H
10.68 s).Its carbon-13 nmr spectra also confirms that and there is carboxyl carbon (δ C 167.3 s) in compound, two methyl carbon (δ C 9.0 q and 18.2 q), a methoxyl group carbon (δ C
61.4 q), 3 fragrant methine carbon (δ C
105.8 d, 111.3 d and 124.1
D), quaternary carbon (the δ C of 4 sp2 oxidations
162.7 s、156.9 s、146.1
S and 155.2 s), and 3 sp2 fragrance quaternary carbons (δ C 103.0 s, 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) relevant with the HMBC of C-2 (δ C 162.7) (figure-3) confirms to there is 3-methyl-ribofuranosyl formic acid structure 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 (δH
6.68) and C-5 (δ C
156.9) HMBC is correlated with and confirms have phenyl ring to be substituted in the C-5 position of furan nucleus.The position of other substituent, another 1 methyl is substituted in C-10 position can pass through the relevant confirmation of HMBC of H3-14 (δ H 2.39) and C-9 (δ C 152.5), C-10 (δ C 127.2) and C-11 (δ C 124.1)；Methoxy substitution can be by methoxyl group hydrogen (δ H at C-9
3.86) and C-9 (δ C
152.5) HMBC is relevant to be determined；Phenolic hydroxyl group is substituted in C-8 position can be by phenolic hydroxyl group hydrogen (δ H
10.68) and C-7 (δ C
111.3)、C-8 (δC
146.1) and C-9 (δ C
152.5) HMBC is relevant to be confirmed.So far the structure of compound is determined, and named 6-(3 ＇-hydroxyl-4 ＇-methoxyl group-5 ＇-aminomethyl phenyl)-3-methyl-ribofuranosyl-2-formic acid.
Table
-1.
Compound
1
H NMR
With
13
C NMR
Data
(C5D5N)
The third object of the present invention is achieved in that and will be applied to the preparation of resisting tobacco mosaic virus medicine by described furancarboxylic acid compounds.
The compounds of this invention is separated first, is defined as furancarboxylic acid compounds by nuclear magnetic resonance and measuring method of mass spectrum, and characterizes its concrete structure.Through the experiment to resisting tobacco mosaic virus, its relative inhibition reaches 36.2%, exceedes the relative inhibition (31.5%) of positive reference substance Ningnanmycin, has good activity of resisting tobacco mosaic virus.The compounds of this invention simple in construction activity preferably, can have a good application prospect as the guiding compound of resisting tobacco mosaic virus medicine.
Accompanying drawing explanation
Fig. 1 be furancarboxylic acid compounds of the present invention carbon-13 nmr spectra (13C NMR)；
Fig. 2 be furancarboxylic acid compounds of the present invention proton nmr spectra (1H NMR)；
Fig. 3 is that the main HMBC of furancarboxylic acid compounds of the present invention is correlated with.
Detailed description of the invention
Below in conjunction with embodiment and accompanying drawing, the present invention is described in further detail, but is any limitation as the present invention never in any form, based on present invention teach that any conversion or improvement made, each falls within protection scope of the present invention.
Furancarboxylic acid compounds of the present invention, is isolated from cured tobacco leaf, and its molecular formula is C14H14O5, have a structure in which
Named 6-(3 ＇-hydroxyl-4 ＇-methoxyl group-5 ＇-aminomethyl phenyl)-3-methyl-ribofuranosyl-2-formic acid, English entitled [6-(3 ＇-hydroxy-4 ＇-methoxy-5 ＇-methylphenyl)-3-methyl-furan-2-carboxylic acid].
The preparation method of furancarboxylic acid compounds of the present invention, is with cured tobacco leaf as raw material, through medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography separating step, particularly as follows:
A. medicinal extract extracts: with tobacco leaf as raw material, is pulverized by tobacco leaf or is cut into segment, soaks with the organic solvent of 60 ~ 100% and extract 3 ~ 5 times, and each 24 h～72 h merge extract, filtration, and reduced pressure concentration becomes medicinal extract；
B. silica gel column chromatography: after medicinal extract dissolves with organic solvent, with medicinal extract weight ratio 0.8～the 80 of 1.2 times～100 mesh silica gel mixed sample, then carry out silica gel column chromatography with 160～300 mesh silica gel dry column-packings of medicinal extract weight ratio 2～4 times amount；With volume join as 1:0 ~ chloroform-acetone solution of 1:2 carries out gradient elution, collect each several part eluent and also concentrate, merge identical part；
C. high pressure liquid chromatography separates: the 1:1 part of step B eluent i.e. obtains described furancarboxylic acid compounds with high pressure liquid chromatography is isolated and purified further.
Any one during organic solvent is methyl alcohol, ethanol, acetone in described step A.
In described step A, organic solvent is 2～4:1 with the weight ratio of tobacco leaf.
In described step B, organic solvent is pure methyl alcohol, straight alcohol or the pure acetone of medicinal extract weight ratio 1.5～3 times amount.
Chloroform-acetone solution volume proportion in described step B is 1:0,20:1,9:1,8:2,7:3,6:4,1:1 and 1:2.
Described step C mesohigh liquid chromatogram is isolated and purified is employing 21.2
Mm × 250 mm, 5μThe C of m18Chromatographic column, flow velocity is 20 mL/min, and flowing is the methyl alcohol of 30% mutually, and UV-detector detection wavelength is 306 nm, each sample introduction 200μL, collects the chromatographic peak of 19.5 min, is evaporated after repeatedly adding up.
Material after described step C mesohigh liquid chromatogram is isolated and purified dissolves with pure methyl alcohol again, then with pure methyl alcohol for flowing phase, separates with gel filtration chromatography, with the most isolated and purified.
The furancarboxylic acid compounds of the present invention application in preparing resisting tobacco mosaic virus medicine.
The present invention is raw materials used not to be limited by area and kind, all can realize the present invention, and below to derive from the raw tobacco material of cigarette industry Co., Ltd different sources in Yunnan, the present invention will be further described:
Embodiment
1
Tobacco sample derives from Yunnan Yuxi, and kind is Yuxi K326.Taking tobacco leaf 2.0 kg to pulverize, the methyl alcohol with 95% extracts 5 times, extracts 24 h every time, and extract merges, and filters, and reduced pressure concentration becomes medicinal extract, obtains medicinal extract 105 g.With the 100 thick silica gel mixed samples of mesh of 120 g after the pure methyl alcohol dissolving of medicinal extract weight ratio 2.0 times amount, 0.6
The 160 mesh silica gel dress posts of kg carry out silica gel column chromatography, with the chloroform that volume proportion is 1:0,20:1,9:1,8:2,7:3,6:4,1:1,1:2-acetone gradient elution, TLC monitoring merges identical part, obtain 8 parts, wherein volume proportion is the chloroform-acetone elution fraction peace prompt logical sequence 1,100 half preparative high-performance liquid chromatographic separation of 1:1, methyl alcohol with 30% is flowing phase, Zorbax SB-C18
(21.2 × 250 mm, 5 μm) prepare post for fixing phase, flow velocity is 20
Ml/min, UV-detector detection wavelength is 306 nm, and each sample introduction 200 μ L collects the chromatographic peak of 19.5 min, is evaporated after repeatedly adding up；Products therefrom dissolves with pure methyl alcohol again, then with pure methyl alcohol for flowing phase, separates with Sephadex LH-20 gel filtration chromatography, obtain this noval chemical compound.
Embodiment
2
Tobacco sample derives from Dali, and kind is cloud and mist 200.Taking tobacco leaf 3.5 kg chopping, the alcohol extract with 95% 4 times, extract 48 h every time, extract merges, and filters, and reduced pressure concentration becomes medicinal extract, obtains medicinal extract 250 g.With the 80 thick silica gel mixed samples of mesh of 250 g after the pure methyl alcohol dissolving of medicinal extract weight ratio 2.0 times amount, 1.2
The 200 mesh silica gel dress posts of kg carry out silica gel column chromatography, with the chloroform that volume proportion is 1:0,20:1,9:1,8:2,7:3,6:4,1:1,1:2-acetone gradient elution, TLC monitoring merges identical part, obtain 8 parts, wherein volume proportion is the chloroform-acetone elution fraction peace prompt logical sequence 1,100 half preparative high-performance liquid chromatographic separation of 1:1, methyl alcohol with 30% is flowing phase, Zorbax SB-C18
(21.2 × 250 mm, 5 μm) prepare post is fixing phase, and flow velocity is 20 ml/min, and UV-detector detection wavelength is 306 nm, and each sample introduction 200 μ L collects the chromatographic peak of 19.5 min, is evaporated after repeatedly adding up；Products therefrom dissolves with pure methyl alcohol again, then with pure methyl alcohol for flowing phase, separates with Sephadex LH-20 gel filtration chromatography, obtain this noval chemical compound.
Embodiment
3
Tobacco sample derives from Kunming, Yunnan, and kind is the big gold dollar of safflower.Taking tobacco leaf 5 kg to pulverize, the ultrasonic extraction 3 times of the acetone with 75%, extract 72h every time, extract merges, and filters, and reduced pressure concentration becomes medicinal extract, obtains medicinal extract 380 g.With the 90 thick silica gel mixed samples of mesh of 400 g after the pure methyl alcohol dissolving of medicinal extract weight ratio 1.6 times amount, the 180 mesh silica gel dress posts of 2.4 kg carry out silica gel column chromatography, with the chloroform that volume proportion is 1:0,20:1,9:1,8:2,7:3,6:4,1:1,1:2-acetone gradient elution, TLC monitoring merges identical part, obtain 8 parts, wherein volume proportion is the chloroform-acetone elution fraction peace prompt logical sequence 1,100 half preparative high-performance liquid chromatographic separation of 1:1, methyl alcohol with 30% is flowing phase, Zorbax SB-C18 (21.2 × 250
Mm, 5 μm) prepare post for fixing phase, flow velocity is 20
Ml/min, UV-detector detection wavelength is 306 nm, and each sample introduction 200 μ L collects the chromatographic peak of 19.5 min, is evaporated after repeatedly adding up；Products therefrom dissolves with pure methyl alcohol again, then with pure methyl alcohol for flowing phase, separates with Sephadex LH-20 gel filtration chromatography, obtain this noval chemical compound.
Embodiment
4
The compound of Example 1 preparation, for light yellow gum thing；
Assay method is: with nuclear magnetic resonance, identify structure in conjunction with other spectroscopic technique.
The compounds of this invention is light yellow gum thing；Ultraviolet spectra (solvent is methyl alcohol), 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).Providing molecular formula C14H14O5 in conjunction with 1H and 13 C H NMR spectroscopy, degree of unsaturation is 8.Confirm that compound has-OH (3418 cm-1), CO2H (br. 3023 cm-1) ,-CO2 (1687 cm-1) and aromatic ring (1613 and 1582 from the ir data of compound 1
Cm-1) functional group.The proton nmr spectra of compound confirms to exist in compound 1 methoxyl group (δ H 3.86 s), 1 carboxyl (δ H 10.05), 3 fragrant methines (δ H 6.21 s, 6.53 s and 6.68 s), two methyl (δ H 1.85 s and 2.39 s) and 1 phenolic hydroxyl group (δ H
10.68 s).Its carbon-13 nmr spectra also confirms that and there is carboxyl carbon (δ C 167.3 s) in compound, two methyl carbon (δ C 9.0 q and 18.2 q), a methoxyl group carbon (δ C
61.4 q), 3 fragrant methine carbon (δ C
105.8 d, 111.3 d and 124.1
D), quaternary carbon (the δ C of 4 sp2 oxidations
162.7 s、156.9 s、146.1
S and 155.2 s), and 3 sp2 fragrance quaternary carbons (δ C 103.0 s, 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) relevant with the HMBC of C-2 (δ C 162.7) (figure-3) confirms to there is 3-methyl-ribofuranosyl formic acid structure 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 (δH
6.68) and C-5 (δ C
156.9) HMBC is correlated with and confirms have phenyl ring to be substituted in the C-5 position of furan nucleus.The position of other substituent, another 1 methyl is substituted in C-10 position can pass through the relevant confirmation of HMBC of H3-14 (δ H 2.39) and C-9 (δ C 152.5), C-10 (δ C 127.2) and C-11 (δ C 124.1)；Methoxy substitution can be by methoxyl group hydrogen (δ H at C-9
3.86) and C-9 (δ C
152.5) HMBC is relevant to be determined；Phenolic hydroxyl group is substituted in C-8 position can be by phenolic hydroxyl group hydrogen (δ H
10.68) and C-7 (δ C
111.3)、C-8 (δC
146.1) and C-9 (δ C
152.5) HMBC is relevant to be confirmed.So far the structure of compound is determined, and named 6-(3 ＇-hydroxyl-4 ＇-methoxyl group-5 ＇-aminomethyl phenyl)-3-methyl-ribofuranosyl-2-formic acid.
Embodiment
5
Compound prepared by Example 2, for light yellow gum thing.Assay method is the same as in Example 4, confirms that the compound of embodiment 2 preparation is described furancarboxylic acid compounds.
Embodiment
6
Compound prepared by Example 3, for light yellow gum thing.Assay method is the same as in Example 4, confirms that the compound of embodiment 3 preparation is described furancarboxylic acid compounds.
Embodiment
7
Furancarboxylic acid compounds prepared by Example 1 ~ 4 carries out activity of resisting tobacco mosaic virus test, and test situation is as follows:
Using half leaf method, the mass concentration at medicament carries out activity of resisting tobacco mosaic virus mensuration to the compounds of this invention when being 50 mg/L.5～6 age flue-cured tobacco plant on, choose the blade (leaf row normal, anosis without worm) being applicable to test, first blade uniformly sprinkled fine emery powder, with writing brush by standby tobacco mosaic virus (TMV) source (3.0 × 10-3) be uniformly put on sprinkled with on the blade of diamond dust, connect after poison terminates until the blade of all middle choosings, it is immediately placed to fill in the culture dish of liquid and processes 20 min, take out, wipe the globule and liquid on blade, two and half leaves are restored and is emitted in the glass jar being covered with toilet paper moisturizing, and cover glass cover, temperature control (23 ± 2) DEG C, it is placed on greenhouse natural light irradiation, the i.e. visible withered spot of 2～3 d. each process sets second half leaf for comparison, is additionally provided with process that 1 group is commodity Ningnanmycin as a comparison, presses formula calculating relative inhibition.
XI%=(CK-T)/CK × 100%
X: relative inhibition (%), CK: being soaked in half in clear water and connect the withered spot number (individual) of poison leaf, T is soaked in half in liquid and connects the withered spot number (individual) of poison leaf.
The relative inhibition of bright compound of result is 36.2%, exceedes the relative inhibition 31.5% of comparison Ningnanmycin, illustrates that compound has good activity of resisting tobacco mosaic virus.
Claims (9)
1. a furancarboxylic acid compounds, it is characterised in that described furancarboxylic acid compounds is isolated from cured tobacco leaf, its molecular formula is C14H14O5, have a structure in which
This Compound nomenclature is: 6-(3 ＇-hydroxyl-4 ＇-methoxyl group-5 ＇-aminomethyl phenyl)-3-methyl-ribofuranosyl-2-formic acid, English entitled: [6-(3 ＇-hydroxy-4 ＇-methoxy-5 ＇-methylphenyl)-3-methyl-furan-2-carboxylic
acid]。
2. the preparation method of the furancarboxylic acid compounds described in a claim 1, it is characterised in that with cured tobacco leaf as raw material, through medicinal extract extraction, silica gel column chromatography, high pressure liquid chromatography separating step, particularly as follows:
A. medicinal extract extracts: with tobacco leaf as raw material, is pulverized by tobacco leaf or is cut into segment, soaks with the organic solvent of 60 ~ 100% and extracts 3 ~ 5 times, and each 24
H～72
H, merges extract, filtration, and reduced pressure concentration becomes medicinal extract；
B. silica gel column chromatography: after medicinal extract dissolves with organic solvent, with medicinal extract weight ratio 0.8～the 80 of 1.2 times～100 mesh silica gel mixed sample, then carry out silica gel column chromatography with 160～300 mesh silica gel dry column-packings of medicinal extract weight ratio 2～4 times amount；With volume join as 1:0 ~ chloroform-acetone solution of 1:2 carries out gradient elution, collect each several part eluent and also concentrate, merge identical part；
C. high pressure liquid chromatography separates: the 1:1 part of step B eluent i.e. obtains described furancarboxylic acid compounds with high pressure liquid chromatography is isolated and purified further.
The preparation method of furancarboxylic acid compounds the most according to claim 2, it is characterised in that any one during organic solvent is methyl alcohol, ethanol, acetone in described step A.
The preparation method of furancarboxylic acid compounds the most according to claim 2, it is characterised in that in described step A, organic solvent is 2～4:1 with the weight ratio of tobacco leaf.
The preparation method of furancarboxylic acid compounds the most according to claim 2, it is characterised in that in described step B, organic solvent is pure methyl alcohol, straight alcohol or the pure acetone of medicinal extract weight ratio 1.5～3 times amount.
The preparation method of furancarboxylic acid compounds the most according to claim 2, it is characterised in that the chloroform-acetone solution volume proportion in described step B is 1:0,20:1,9:1,8:2,7:3,6:4,1:1 and 1:2.
The preparation method of furancarboxylic acid compounds the most according to claim 2, it is characterised in that described step C mesohigh liquid chromatogram is isolated and purified is employing 21.2
mm ×
250 mm, 5μThe C of m18Chromatographic column, flow velocity is 20
ML/min, flowing is the methyl alcohol of 30% mutually, and UV-detector detection wavelength is 306 nm, each sample introduction 200
μL, collects 19.5
The chromatographic peak of min, is evaporated after repeatedly adding up.
The preparation method of furancarboxylic acid compounds the most according to claim 2, it is characterized in that described step C mesohigh liquid chromatogram isolated and purified after material again with pure methyl alcohol dissolve, again with pure methyl alcohol for flowing phase, separate with gel filtration chromatography, with the most isolated and purified.
9. the application in preparing resisting tobacco mosaic virus medicine of the furancarboxylic acid compounds described in a claim 1.
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| CN102977059A (en) * | 2012-12-06 | 2013-03-20 | 云南烟草科学研究院 | Phenylpropanoid compound, and preparation method and application thereof |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102977059A (en) * | 2012-12-06 | 2013-03-20 | 云南烟草科学研究院 | Phenylpropanoid compound, and preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| YE-KUN YANG,ET AL: "Neolignans from Flower Buds of Magnolia fargesii and their Antitobacco Mosaic Virus Activities", 《ASIAN JOURNAL OF CHEMISTRY》 * |
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