CN105152880A - Nicotianasesterpene-F prepared through supercritical fluid chromatography and application of nicotianasesterpene-F - Google Patents
Nicotianasesterpene-F prepared through supercritical fluid chromatography and application of nicotianasesterpene-F Download PDFInfo
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- CN105152880A CN105152880A CN201510712402.9A CN201510712402A CN105152880A CN 105152880 A CN105152880 A CN 105152880A CN 201510712402 A CN201510712402 A CN 201510712402A CN 105152880 A CN105152880 A CN 105152880A
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- C07—ORGANIC CHEMISTRY
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- C07C41/01—Preparation of ethers
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Abstract
The invention discloses a sesquiterpene compound which is prepared through supercritical fluid chromatography and is novel in structure. The compound is named as nicotianasesterpene-F, wherein the molecular formula of nicotianasesterpene-F is C16H20O2, and the nicotianasesterpene-F has the following structure (please see the structure in the specification). The invention further discloses application of the compound. Activity tests show that nicotianasesterpene-F has a very good restraining effect on tobacco mosaic viruses and can be used for research and development on tobacco mosaic virus prevention pharmaceutic preparations as the lead compound for preventing tobacco mosaic viruses.
Description
Technical field
The invention belongs to technical field of tobacco chemistry, be specifically related to a kind ofly from tobacco, extract the sesquiterpenoids obtained first.Meanwhile, the invention still further relates to the preparation method of this compound and the application in resisting tobacco mosaic virus.
Background technology
Tobacco is the plant that chemical composition is the most complicated in the world, and secondary metabolite is very abundant, and through the research of decades, the monomer chemistries material that people identify out at present from tobacco just more than kind more than 3000, and also has many compositions not yet to identify out.Extensively approved although Smoking is harmful to your health, tobacco still has powerful magnetism to thousands of human consumer, except Nicotine additive except, fragrance matter abundant in tobacco also plays an important role.
Supercritical fluid chromatography is with supercutical fluid (such as CO
2) as the chromatographic process of moving phase, supercutical fluid has low viscosity and the high diffusivity coefficient of gas concurrently, be about 10 ~ 100 times of liquid, have again the high-density close with liquid and strong dissolving power, therefore supercritical fluid chromatography has both the advantage of gas-chromatography and high performance liquid chromatography.It both can be separated the not segregative high molecular weight compound of liquid chromatography, also can the not segregative thermally labile of segregation gas chromatography, strong polarity or non-volatile compounds.Therefore, supercritical fluid chromatography is suitable for the separation preparation of compound in natural product very much.
Sesquiterpene (sesquiterpenes) refers to the natural terpenoids containing 15 carbon atoms in molecule.Sesquiterpenoids is distributed more widely, and being often present in volatile oil with alcohol, ketone, lactone etc. form in plant materials, is the chief component of high-boiling fration in volatile oil.Have stronger fragrance and biological activity, be the important source material of medicine, food, cosmetic industry more.In order to study the structure activity relationship of this compounds, more sesquiterpenoids can be researched and developed further, and therefrom finding effective lead compound and active group.The present invention is by supercritical fluid chromatography, and be separated from Yunnan Flue-cured Tobacco tobacco leaf and obtain a kind of new sesquiterpenoids, this compound it is not yet seen relevant report, it is worth mentioning that this compound has significant resisting tobacco mosaic disease virus activity.
Summary of the invention
A first aspect of the present invention is to provide a kind of new sesquiterpenoids, and this compound is separated and obtains from Yunnan Flue-cured Tobacco tobacco leaf, and its molecular formula is C
16h
20o
2, chemical identification by analysis, it has following structure:
This compound is light yellow gum thing, and the present inventor is by its Chinese name called after tobacco sesquiterpene-F, and its English is called nicotianasesterpeneF.
A second aspect of the present invention provides the preparation method of the sesquiterpenoids described in above-mentioned first aspect, and the method comprises the steps:
(1) tobacco extract medicinal extract is prepared: take tobacco leaf as raw material, pulverized or be cut into segment, and extract described tobacco 3 ~ 5 times, each 24h ~ 72h with the first solvent soaking, extracting solution is merged, filters and obtain described tobacco extract medicinal extract after concentrating; Wherein said first solvent is selected from the organic solvent of methyl alcohol, ethanol or acetone and the mixture of water, wherein organic solvent accounts for the preparation method of this terpenoid, the method comprises the steps: the 60wt% ~ 100wt% of a solvent, and the first solvent: tobacco=2 ~ 4:1, weight ratio;
(2) silica gel column chromatography: by above-mentioned tobacco extract medicinal extract with being selected from pure methyl alcohol, with 60 ~ 120 order silica gel mixed samples of 0.8 ~ 1.2 times of weight being tobacco extract medicinal extract after second dissolution with solvents of straight alcohol or pure acetone, rear dry column-packing is mixed again with 160 ~ 300 order silica gel of 2 ~ 4 times of weight for tobacco extract medicinal extract by mixing the mixture after sample, then 1:0 is followed successively by by volume ratio, 20:1, 9:1, 8:2, 7:3, 6:4, the chloroform-acetone solution of 1:1 and 1:2 carries out gradient elution, the elutriant obtained when wherein volume is the chloroform-acetone solution wash-out of 8:2 is called the first elutriant.
(3) supercritical fluid chromatography separation and purification: above-mentioned first elutriant is passed into supercritical fluid chromatography and carries out separation and purification, this supercritical fluid chromatography adopts 10mm × 150mm, the Silica2-EP chromatographic column of 5 μm, moving phase carbon dioxide/methanol (90/10%, mass ratio), flow rate of mobile phase is 25mL/min, UV-detector determined wavelength is 254nm, first elutriant liquid each sample introduction 200 ~ 500 μ L, elutriant corresponding when to collect chromatographic peak retention time after each sample introduction be 16.7min, be called the second elutriant, namely described sesquiterpenoid is obtained by after this second elutriant desolvation.
In preferred embodiments, the present invention also comprises the step of following further purification: the described sesquiterpenoid obtained after described supercritical fluid chromatography separation is dissolved in methanol solution again, and with methanol solution for moving phase, carry out chromatographic separation by gel column, obtain the described sesquiterpenoid of purifying further.
The sesquiterpenoids that a third aspect of the present invention provides described in first aspect is preparing the purposes in resisting tobacco mosaic virus medicine.
Accompanying drawing explanation
Fig. 1 is the carbon-13 nmr spectra of sesquiterpenoids of the present invention;
Fig. 2 is the proton nmr spectra of sesquiterpenoids of the present invention;
Fig. 3 is the main HMBC relevant indicators of sesquiterpenoids of the present invention.
Embodiment
The structure of the sesquiterpenoids prepared by the present invention measures out by the following method.The compounds of this invention is light yellow gum thing; UV spectrum (solvent is methyl alcohol), λ
max(log ε) 210 (3.18), 265 (3.35), 306 (2.38) nm; Infrared spectra (pressing potassium bromide troche) ν
max3436,3087,2926,1625,1548,1465,1346,1158,1037,892,783cm
-1; High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak m/z267.1366 [M+Na]
+(calculated value 267.1361).In conjunction with
1h and
13cNMR spectrum provides a molecular formula C
16h
20o
2, degree of unsaturation is 7.Its infrared spectra shows hydroxyl (3436cm
-1) and phenyl ring 1625,1548,1465cm
-1) functional group; UV spectrum has strong absorption in 265 and 306nm place, also confirms to there is conjugated structure in compound.From
1h and
13cNMR composes (attribution data is in Table-1) signal can find out in compound have 2,4,8,9-quaternary indenes parent nucleus, an isobutenyl, 1 methylol, a methyl and a methoxyl group.According to H-3 and C-2, C-4, C-1, C-5, and there is indenes parent nucleus in the HMBC of H-6 with C-4 relevant (figure-3) susceptible of proof compound.After the parent nucleus of compound is determined, remaining isobutenyl, methylol, methyl and methoxyl group are the substituting group on parent nucleus.The C-2 position of parent nucleus is substituted according to the relevant susceptible of proof isobutenyl of the HMBC of H-10 with C-1, C-2 with C-3; The C-4 of parent nucleus is substituted in, according to the relevant susceptible of proof methyl substituted of the HMBC of H-15 with C-7, C-8 with C-9 in the C-8 position of parent nucleus according to H-14 and C-3, C-4 and C-5 susceptible of proof methylol; Relevant with the HMBC of C-9 according to methoxyl group hydrogen, susceptible of proof methoxy substitution is in the C-9 position of parent nucleus.So far the structure of this compound is determined.
Table 1. compound
1hNMR and
13cNMR data (C
5d
5n)
The compounds of this invention is separated first, is defined as sesquiterpenoids by above-mentioned nucleus magnetic resonance and measuring method of mass spectrum, and characterizes its concrete structure.Half leaf method is adopted to carry out the activity of resisting tobacco mosaic virus test of the compounds of this invention, the relative inhibition of result bright compound is 33.6%, exceed the relative inhibition 31.5% of positive control Ningnanmycin, illustrated that compound has good activity of resisting tobacco mosaic virus.Activity determination result discloses compound of the present invention preparing in resisting tobacco mosaic virus medicine good application prospect.The compounds of this invention structure is simple, better active, and the guiding compound that can be used as resisting tobacco mosaic virus medicament research and development is researched and developed for resisting tobacco mosaic virus pharmaceutical preparation.
Below in conjunction with embodiment and accompanying drawing, the present invention is further illustrated, but limited the present invention never in any form, and any conversion done based on training centre of the present invention or improvement, all fall into protection scope of the present invention.
The present invention is raw materials used not to be limited by area and kind, and the tobacco in any source place all can realize the present invention, and to derive from the tobacco material of cigarette industry limited liability company in Yunnan, the present invention will be further described below.Except as otherwise noted, the percentage ratio adopted in the present invention is mass percent.
Embodiment 1
Tobacco sample derives from Yunnan Yuxi, and kind is Yuxi K326.Tobacco is sampled 2.0kg and pulverize methanol extraction 5 times with 95%, extract 24h, extracting solution merges at every turn, and filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 105g.With the thick silica gel mixed sample of 100 order of 120g after the pure dissolve with methanol of medicinal extract weight ratio 2.0 times amount, the 160 order silica gel dress posts of 0.4kg carry out silica gel column chromatography, be 1:0 with volume proportion, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone the gradient elution of 1:2, thin-layer chromatography (TLC) monitoring merges identical part, obtain 8 parts, wherein volume proportion is that chloroform-this SFC80Q supercutical fluid of acetone elution fraction water of 8:2 prepares chromatographic separation, take carbon dioxide/methanol as moving phase (90/10%, mass ratio), Silica2-EP (10mm × 150mm, 5 μm) preparative column is stationary phase, flow rate of mobile phase is 25mL/min, UV-detector determined wavelength is 254nm, each sample introduction 200 μ L, elutriant corresponding when to collect chromatographic peak retention time after each sample introduction be 16.7min, repeatedly cumulative rear evaporate to dryness, obtain sesquiterpenoid crude product of the present invention, this crude product uses pure dissolve with methanol again, with pure methyl alcohol for moving phase, can obtain sterling with dextrane gel column chromatography purification.
Embodiment 2
Tobacco sample derives from Dali, and kind is cloud and mist 200, and tobacco is sampled 3.5kg chopping, the extraction using alcohol with 95% 4 times, extracts 48h at every turn, and extracting solution merges, and filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 250g.With the thick silica gel mixed sample of 80 order of 250g after the pure dissolve with methanol of medicinal extract weight ratio 2.0 times amount, the 200 order silica gel dress posts of 0.5kg carry out silica gel column chromatography, be 1:0 with volume proportion, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone the gradient elution of 1:2, TLC monitoring merges identical part, obtain 8 parts, wherein volume proportion is that chloroform-this SFC80Q supercutical fluid of acetone elution fraction water of 8:2 prepares chromatographic separation, take carbon dioxide/methanol as moving phase (90/10%, mass ratio), Silica2-EP (10mm × 150mm, 5 μm) preparative column is stationary phase, flow rate of mobile phase is 25mL/min, UV-detector determined wavelength is 254nm, each sample introduction 200 μ L, elutriant corresponding when to collect chromatographic peak retention time after each sample introduction be 16.7min, repeatedly cumulative rear evaporate to dryness, obtain sesquiterpenoid crude product of the present invention, this crude product uses pure dissolve with methanol again, with pure methyl alcohol for moving phase, purifies can obtain this new compound more highly purified with SephadexLH-20 gel filtration chromatography.
Embodiment 3
Tobacco sample derives from Kunming, Yunnan, and kind is the large gold dollar of safflower, tobacco is sampled 5kg and pulverizes, and the supersound extraction 3 times of the acetone with 75%, extracts 72h at every turn, and extracting solution merges, and filter, concentrating under reduced pressure becomes medicinal extract, obtains medicinal extract 380g.With the thick silica gel mixed sample of 90 order of 400g after the pure dissolve with methanol of medicinal extract weight ratio 1.6 times amount, the 180 order silica gel dress posts of 2.4kg carry out silica gel column chromatography, be 1:0 with volume proportion, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, chloroform-acetone the gradient elution of 1:2, TLC monitoring merges identical part, obtain 8 parts, wherein volume proportion is that chloroform-this SFC80Q supercutical fluid of acetone elution fraction water of 8:2 prepares chromatographic separation, take carbon dioxide/methanol as moving phase (90/10%, mass ratio), Silica2-EP (10mm × 150mm, 5 μm) preparative column is stationary phase, flow rate of mobile phase is 25mL/min, UV-detector determined wavelength is 254nm, each sample introduction 200 μ L, elutriant corresponding when to collect chromatographic peak retention time after each sample introduction be 16.7min, repeatedly cumulative rear evaporate to dryness, obtain sesquiterpenoid crude product of the present invention, this crude product uses pure dissolve with methanol again, with pure methyl alcohol for moving phase, purifies can obtain this new compound more highly purified with SephadexLH-20 gel filtration chromatography.
Embodiment 4
Compound prepared by Example 1 is light yellow gum thing.
The structure of the sesquiterpenoids prepared by the present invention measures out by the following method.The compounds of this invention is light yellow gum thing; UV spectrum (solvent is methyl alcohol), λ
max(log ε) 210 (3.18), 265 (3.35), 306 (2.38) nm; Infrared spectra (pressing potassium bromide troche) ν
max3436,3087,2926,1625,1548,1465,1346,1158,1037,892,783cm
-1; High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak m/z267.1366 [M+Na]
+(calculated value 267.1361).In conjunction with
1h and
13cNMR spectrum provides a molecular formula C
16h
20o
2, degree of unsaturation is 7.Its infrared spectra shows hydroxyl (3436cm
-1) and phenyl ring 1625,1548,1465cm
-1) functional group; UV spectrum has strong absorption in 265 and 306nm place, also confirms to there is conjugated structure in compound.From
1h and
13cNMR composes (attribution data is in Table-1) signal can find out in compound have 2,4,8,9-quaternary indenes parent nucleus, an isobutenyl, two methylols, methoxyl groups.According to H-3 and C-2, C-4, C-1, C-5, and there is indenes parent nucleus in the HMBC of H-6 with C-4 relevant (figure-3) susceptible of proof compound.After the parent nucleus of compound is determined, remaining isobutenyl, methylol and methoxyl group are the substituting group on parent nucleus.The C-2 position of parent nucleus is substituted according to the relevant susceptible of proof isobutenyl of the HMBC of H-10 with C-1, C-2 with C-3; The C-4 of parent nucleus is substituted in, according to the relevant susceptible of proof methyl substituted of the HMBC of H-15 with C-7, C-8 with C-9 in the C-8 position of parent nucleus according to H-14 and C-3, C-4 and C-5 susceptible of proof methylol; Relevant with the HMBC of C-9 according to methoxyl group hydrogen, susceptible of proof methoxy substitution is in the C-9 position of parent nucleus.So far the structure of this compound is determined.
Embodiment 5
Compound prepared by Example 2 is yellow jelly.Measuring method is identical with embodiment 4, confirms that compound prepared by embodiment 2 is described sesquiterpenoids---tobacco sesquiterpene-F.
Embodiment 6
Compound prepared by Example 3 is yellow jelly.Measuring method is identical with embodiment 4, confirms that compound prepared by embodiment 3 is described tobacco sesquiterpene-F.
Embodiment 7
Arbitrary sesquiterpenoids prepared by Example 1-3 carries out activity of resisting tobacco mosaic virus test, and test situation is as follows:
Adopt half leaf method, when the mass concentration of medicament is 50mg/L, activity of resisting tobacco mosaic virus mensuration is carried out to the compounds of this invention.5 ~ 6 age flue-cured tobacco plant on, choose the blade (leaf capable normal, anosis without worm) being applicable to test, first blade evenly sprinkled fine emery powder, with writing brush by tobacco mosaic virus (TMV) source (3.0 × 10 for subsequent use
-3) be evenly put on sprinkled with silicon carbide blade on, connect after poison terminates until the blade of all middle choosings, be placed on immediately in the culture dish filling liquid and process 20min, take out, wipe the globule and liquid on blade, being restored by two and half leaves is emitted in the glass jar being covered with toilet paper moisturizing, and cover glass cover, temperature control (23 ± 2) DEG C, be placed on greenhouse natural light irradiation, 2 ~ 3d and visible withered spot. each process set second half leaf as contrast, be provided with in addition 1 group be the process of commodity Ningnanmycin as a comparison, press formulae discovery relative inhibition.
XI％＝(CK-T)/CK×100％
X: relative inhibition (%), CK: be soaked in the withered spot number (individual) that half in clear water connects malicious leaf, T is soaked in the withered spot number (individual) that half in liquid connects malicious leaf.
The relative inhibition of result bright compound is 33.6%%, exceedes the relative inhibition 31.5% of contrast Ningnanmycin, illustrates that compound has good activity of resisting tobacco mosaic virus.
Claims (4)
1. one kind has the sesquiterpenoids of following structural formula:
The called after tobacco sesquiterpene-F of this compound, its molecular formula is C
16h
20o
2.
2. prepare a method for sesquiterpenoid according to claim 1 by supercritical fluid chromatography, the method comprises the following steps:
(1) tobacco extract medicinal extract is prepared: take tobacco leaf as raw material, pulverized or be cut into segment, and extract described tobacco 3 ~ 5 times, each 24h ~ 72h with the first solvent soaking, extracting solution is merged, filters and obtain described tobacco extract medicinal extract after concentrating; Wherein said first solvent is selected from the organic solvent of methyl alcohol, ethanol or acetone and the mixture of water, and wherein organic solvent accounts for the 60wt% ~ 100wt% of this first solvent, and the first solvent: tobacco=2 ~ 4:1, weight ratio;
(2) silica gel column chromatography: by above-mentioned tobacco extract medicinal extract with being selected from pure methyl alcohol, with 60 ~ 120 order silica gel mixed samples of 0.8 ~ 1.2 times of weight being tobacco extract medicinal extract after second dissolution with solvents of straight alcohol or pure acetone, rear dry column-packing is mixed again with 160 ~ 300 order silica gel of 2 ~ 4 times of weight for tobacco extract medicinal extract by mixing the mixture after sample, then 1:0 is followed successively by by volume ratio, 20:1, 9:1, 8:2, 7:3, 6:4, the chloroform-acetone solution of 1:1 and 1:2 carries out gradient elution, the elutriant obtained when wherein volume is the chloroform-acetone solution wash-out of 8:2 is called the first elutriant.
(3) supercritical fluid chromatography separation and purification: above-mentioned first elutriant is passed into supercritical fluid chromatography and carries out separation and purification, this supercritical fluid chromatography adopts 10mm × 150mm, the Silica2-EP chromatographic column of 5 μm, moving phase carbon dioxide/methanol (90/10%, mass ratio), flow rate of mobile phase is 25mL/min, UV-detector determined wavelength is 254nm, first elutriant liquid each sample introduction 200 ~ 500 μ L, elutriant corresponding when to collect chromatographic peak retention time after each sample introduction be 16.7min, be called the second elutriant, namely described sesquiterpenoid is obtained by after this second elutriant desolvation.
3. method according to claim 2, it also comprises the step of following further purification: the described sesquiterpenoid obtained after described supercritical fluid chromatography separation is dissolved in methanol solution again, and be moving phase with methanol solution, carry out chromatographic separation by gel column, mention the described sesquiterpenoid of purifying further.
4. sesquiterpenoids according to claim 1 is preparing the purposes in resisting tobacco mosaic virus medicine.
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| CN105837412A (en) * | 2016-04-20 | 2016-08-10 | 云南中烟工业有限责任公司 | Sesquiterpene compound, preparation method thereof and application thereof to preparation of tobacco mosaic virus resisting medicine |
| CN105906491A (en) * | 2016-04-20 | 2016-08-31 | 云南中烟工业有限责任公司 | Norsesquiterpenoids compound, preparation method thereof and application of norsesquiterpenoids compound to cigarette moisture retention |
| CN105949065A (en) * | 2016-05-20 | 2016-09-21 | 云南中烟工业有限责任公司 | Sesquiterpenoids, preparation method thereof and application of sesquiterpenoids to preparation of medicine for resisting tobacco mosaic viruses |
| CN106008219A (en) * | 2016-05-20 | 2016-10-12 | 云南中烟工业有限责任公司 | Sesquiterpenoid compound, preparation method of sesquiterpenoid compound and application of sesquiterpenoid compound to preparation of anti-rotavirus medicines |
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| CN105837412A (en) * | 2016-04-20 | 2016-08-10 | 云南中烟工业有限责任公司 | Sesquiterpene compound, preparation method thereof and application thereof to preparation of tobacco mosaic virus resisting medicine |
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| CN106117062B (en) * | 2016-06-24 | 2018-05-18 | 云南中烟工业有限责任公司 | A kind of preparation method of Phenylpropanoid Glycosides class fumet and its use in conjunction with cigarette humectant |
| KR102051783B1 (en) * | 2019-09-02 | 2019-12-03 | 부산대학교 산학협력단 | New Synthetic Method of 3,10-disubstituted benzofulvene derivatives |
| CN115745759A (en) * | 2022-12-30 | 2023-03-07 | 云南民族大学 | Methylpropylidene indene sesquiterpene compound extracted from sun-cured tobacco stem bark and preparation method and application thereof |
| CN115745759B (en) * | 2022-12-30 | 2024-01-26 | 云南民族大学 | A sesquiterpene compound extracted from sun-cured tobacco stem bark, and its preparation method and application |
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