CN105152880B - Nicotiana tabacum L. sesquiterpene-F prepared by a kind of supercritical fluid chromatography and application thereof - Google Patents
Nicotiana tabacum L. sesquiterpene-F prepared by a kind of supercritical fluid chromatography and application thereof Download PDFInfo
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Abstract
Present invention supercritical fluid chromatography is prepared for the sesquiterpenoids of a kind of novel structure, and this Compound nomenclature is Nicotiana tabacum L. sesquiterpene F (nicotianasesterpene F), and its molecular formula is C16H20O2, there is following structure.The invention also discloses the purposes of above-claimed cpd, show through active testing, it has good inhibiting effect to tobacco mosaic virus (TMV), can research and develop for resisting tobacco mosaic virus pharmaceutical preparation as the lead compound of resisting tobacco mosaic virus.
Description
Technical field
The invention belongs to technical field of tobacco chemistry, be specifically related to a kind of from Nicotiana tabacum L. first extract obtain times
Half terpenoid.Meanwhile, the invention still further relates to the preparation method of this compound and at resisting tobacco mosaic virus
In application.
Background technology
Nicotiana tabacum L. is the plant that chemical composition is the most complicated in the world, and secondary metabolite is the abundantest, Jing Guoji
The research of 10 years, the monomer chemistries material that people identify out at present from Nicotiana tabacum L. just more than kind more than 3000, and
And also have many compositions not yet to identify out.It is widely recognized although Smoking is harmful to your health, but Nicotiana tabacum L. is still
So there is powerful captivation in thousands of consumer, except nicotine additive in addition to, abundant in Nicotiana tabacum L.
Fragrance matter also play an important role.
Supercritical fluid chromatography is with supercritical fluid (such as CO2) as the chromatographic process of flowing phase, super
Critical fluids has the low viscosity of gas and 10～100 times of high diffusivity coefficient, about liquid concurrently, has again and liquid
High density that body is close and strong solvability, therefore supercritical fluid chromatography has both gas chromatogram and efficient liquid phase
The advantage of both chromatographs.It both can separate the high relative molecular mass compound that liquid chromatograph is not readily separated,
Can also segregation gas chromatography be not readily separated thermally labile, highly polar or non-volatile compounds.Therefore,
Supercritical fluid chromatography is highly suitable for the separation of compound in natural product to be prepared.
Sesquiterpene (sesquiterpenes) refers to the natural terpenoids in molecule containing 15 carbon atoms.Times
Half terpenoid is distributed more widely, is often present in volatile oil with alcohol, ketone, lactone etc. form in plant
In, it is the key component of high-boiling fration in volatile oil.There is stronger fragrance and biological activity more,
It it is the important source material of medicine, food, cosmetics industry.In order to study the structure activity relationship of this compounds, can
Research and develop more sesquiterpenoids further, and therefrom find effective lead compound and work
Property group.The present invention is by supercritical fluid chromatography, and from Yunnan Flue-cured Tobacco Nicotiana tabacum L., isolated is a kind of new
Sesquiterpenoids, this compound it is not yet seen relevant report, it is worth mentioning at this point that this compound has
There is 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 roasting from Yunnan
Isolated in cigarette Nicotiana tabacum L., its molecular formula is C16H20O2, chemical identification by analysis, it has following knot
Structure:
This compound is light yellow gum thing, and the present inventor is by named for its Chinese name Nicotiana tabacum L. sesquiterpene-F, its English
Literary fame is nicotianasesterpene F.
A second aspect of the present invention provides the preparation side of the sesquiterpenoids described in above-mentioned first aspect
Method, the method comprises the steps:
(1) prepare tobacco extract extractum: with tobacco leaf as raw material, pulverized or be cut into segment, and
With the first solvent soaking and extract described Nicotiana tabacum L. 3～5 times, each 24h～72h, extracting solution is merged, filters
And obtain described tobacco extract extractum after concentrating；Wherein said first solvent is selected from methanol, ethanol or third
The organic solvent of ketone and the mixture of water, wherein organic solvent accounts for the preparation method of this terpenoid, should
Method comprises the steps: 60wt%～100wt% of a solvent, and the first solvent: Nicotiana tabacum L.=2～4:1,
Weight ratio；
(2) silica gel column chromatography: by above-mentioned tobacco extract extractum with selected from pure methanol, straight alcohol or pure acetone
The second solvent dissolve after with the 60～120 mesh silica gel mixed samples of 0.8～1.2 times of weight for tobacco extract extractum,
Mixture after mixing sample 160～300 mesh silica gel with 2～4 times of weight for tobacco extract extractum again mix
Rear dry column-packing, is then followed successively by 1:0,20:1,9:1,8:2,7:3,6:4,1:1 and 1:2 by volume ratio
Chloroform-acetone solution carries out gradient elution, obtains during by chloroform-acetone solution eluting that wherein volume is 8:2
Eluent is referred to as the first eluent.
(3) supercritical fluid chromatography is isolated and purified: above-mentioned first eluent is passed through supercritical fluid chromatography and enters
Row is isolated and purified, and this supercritical fluid chromatography uses 10mm × 150mm, the Silica 2-EP chromatograph of 5 μm
Post, flowing phase carbon dioxide/methanol (90/10%, mass ratio), flow rate of mobile phase is 25mL/min, purple
External detector detection wavelength is 254nm, and the first each sample introduction of eluent liquid 200～500 μ L collects to enter every time
The eluent that after sample, chromatographic peak retention time is corresponding when being 16.7min, the referred to as second eluent, by this
Described sesquiterpenoid is i.e. obtained after two eluent desolvations.
In preferred embodiments, present invention additionally comprises the step purified further below: will be described super
The described sesquiterpenoid obtained after critical fluids chromatographic isolation is again dissolved in methanol solution, and with methanol
Solution for flowing phase, carry out chromatography by gel column, the described sesquiterpene purified further
Compound.
The sesquiterpenoids that a third aspect of the present invention provides described in first aspect is preparing anti-Nicotiana tabacum L.
Purposes in 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.
Detailed description of the invention
The structure of the sesquiterpenoids prepared by the present invention measures out by the following method.Of the present inventionization
Compound is light yellow gum thing；Ultraviolet spectra (solvent is methanol), λmax(log ε) 210 (3.18), 265 (3.35),
306(2.38)nm；Infrared spectrum (pressing potassium bromide troche) νmax3436,3087,2926,1625,1548,1465,
1346,1158,1037,892,783cm-1；High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak
m/z 267.1366[M+Na]+(value of calculation 267.1361).In conjunction with1H and13C H NMR spectroscopy provides a molecule
Formula C16H20O2, degree of unsaturation is 7.Its infrared spectrum shows hydroxyl (3436cm-1) and phenyl ring 1625,
1548,1465cm-1) functional group；Ultraviolet spectra has strong absorption at 265 and 306nm, also confirms that chemical combination
Thing exists conjugated structure.From1H and13CNMR spectrum (attribution data is shown in Table-1) signal can be seen that in compound
There are a 2,4,8,9-quaternary indenes parent nucleus, an isobutenyl, 1 methylol, a methyl and a first
Epoxide.HMBC relevant (figure-3) according to H-3 and C-2, C-4, C-1, C-5, and H-6 with C-4 can
Confirm compound exists indenes parent nucleus.After the parent nucleus of compound determines, remaining isobutenyl, methylol, first
Base and methoxyl group are the substituent group on parent nucleus.HMBC according to H-10 with C-1, C-2 with C-3 is relevant can
Confirm that isobutenyl is substituted in the C-2 position of parent nucleus；According to H-14 and C-3, C-4 and C-5 susceptible of proof methylol
It is substituted in the C-4 of parent nucleus, takes according to the HMBC of H-15 with C-7, C-8 with C-9 relevant susceptible of proof methyl
In generation, is in the C-8 position of parent nucleus；Relevant with the HMBC of C-9 according to methoxyl group hydrogen, it can be verified that methoxy substitution exists
The C-9 position of parent nucleus.So far the structure of this compound is determined.
Table 1. compound1H NMR and13C NMR data (C5D5N)
The compounds of this invention is separated first, true by above-mentioned nuclear magnetic resonance, NMR and measuring method of mass spectrum
It is set to sesquiterpenoids, and characterizes its concrete structure.Half leaf method is used to carry out the compounds of this invention
Activity of resisting tobacco mosaic virus test, the relative inhibition of bright compound of result is 33.6%, has exceeded sun
Property comparison Ningnanmycin relative inhibition 31.5%, illustrate compound have good resisting tobacco mosaic virus work
Property.Activity determination result discloses the compound of the present invention to be had well in preparing resisting tobacco mosaic virus medicine
Application prospect.The compounds of this invention simple in construction, activity preferably, can be as resisting tobacco mosaic virus medicines
The guiding compound of 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 never in any form to this
Bright being any limitation as, based on present invention teach that any conversion or improvement made, each falling within the protection model of the present invention
Enclose.
The present invention is raw materials used not to be limited by area and kind, and the Nicotiana tabacum L. in any source place all can realize this
Bright, the present invention is done furtherly deriving from the tobacco material of cigarette industry Co., Ltd in Yunnan below
Bright.Except as otherwise noted, the percent employed in the present invention is mass percent.
Embodiment 1
Tobacco sample derives from Yunnan Yuxi, and kind is Yuxi K326.Nicotiana tabacum L. samples 2.0kg pulverize with 95%
Methanol extraction 5 times, extract 24h every time, extracting solution merges, and filters, and concentrating under reduced pressure becomes extractum, obtains leaching
Cream 105g.The pure methanol of extractum weight ratio 2.0 times amount uses the 100 thick silica gel mixed samples of mesh of 120g after dissolving,
0.4kg 160 mesh silica gel dress posts carry out silica gel column chromatography, with volume proportion be 1:0,20:1,9:1,8:2,
The chloroform of 7:3,6:4,1:1,1:2-acetone gradient elution, thin layer chromatography (TLC) monitoring merges identical portion
Point, obtain 8 parts, wherein volume proportion is chloroform-this SFC 80Q of acetone elution fraction water of 8:2
Supercritical fluid prepares chromatographic isolation, with carbon dioxide/methanol for flowing phase (90/10%, mass ratio), Silica
It is fixing phase that 2-EP (10mm × 150mm, 5 μm) prepares post, and flow rate of mobile phase is 25mL/min,
UV-detector detection wavelength is 254nm, each sample introduction 200 μ L, and after collecting each sample introduction, chromatographic peak retains
The eluent that time is corresponding when being 16.7min, is evaporated after repeatedly adding up, obtains sesquialter of the present invention
Terpene crude compound；This crude product dissolves with pure methanol again, with pure methanol for flowing phase, uses sephadex column
Chromatography purification can obtain sterling.
Embodiment 2
Tobacco sample derives from Dali, and kind is cloud and mist 200, and Nicotiana tabacum L. samples 3.5kg chopping, with
The ethanol extraction of 95% 4 times, extracts 48h every time, and extracting solution merges, and filters, and concentrating under reduced pressure becomes extractum,
Extractum 250g.The pure methanol of extractum weight ratio 2.0 times amount uses the 80 thick silica gel mixed samples of mesh of 250g after dissolving,
0.5kg 200 mesh silica gel dress posts carry out silica gel column chromatography, with volume proportion be 1:0,20:1,9:1,8:2,
The chloroform of 7:3,6:4,1:1,1:2-acetone gradient elution, TLC monitoring merges identical part, obtains 8
Individual part, wherein volume proportion is this SFC 80Q shooting flow of chloroform-acetone elution fraction water of 8:2
Body prepares chromatographic isolation, with carbon dioxide/methanol for flowing phase (90/10%, mass ratio), Silica 2-EP
(10mm × 150mm, 5 μm) prepare post is fixing phase, and flow rate of mobile phase is 25mL/min, ultraviolet
Detector detection wavelength is 254nm, and each sample introduction 200 μ L collects chromatographic peak retention time after each sample introduction
For eluent corresponding during 16.7min, it is evaporated after repeatedly adding up, obtains sesquiterpene of the present invention
Compound crude product；This crude product dissolves with pure methanol again, with pure methanol for flowing phase, coagulates with Sephadex LH-20
Gel column chromatography eluting this noval chemical compound obtaining higher purity.
Embodiment 3
Tobacco sample derives from Kunming, Yunnan, and kind is the big gold dollar of Flos Carthami, Nicotiana tabacum L. samples 5kg and pulverizes, with
The acetone of 75% supersound extraction 3 times, extracts 72h every time, and extracting solution merges, and filters, and concentrating under reduced pressure becomes leaching
Cream, obtains extractum 380g.The pure methanol of extractum weight ratio 1.6 times amount uses the 90 thick silicon of mesh of 400g after dissolving
Sample mixed by glue, 2.4kg 180 mesh silica gel dress posts carry out silica gel column chromatography, with volume proportion be 1:0,20:1,
The chloroform of 9:1,8:2,7:3,6:4,1:1,1:2-acetone gradient elution, TLC monitoring merges identical part,
Obtaining 8 parts, wherein volume proportion is that chloroform-this SFC 80Q of acetone elution fraction water of 8:2 surpasses
Critical fluids preparative hplc separates, with carbon dioxide/methanol for flowing phase (90/10%, mass ratio), Silica
It is fixing phase that 2-EP (10mm × 150mm, 5 μm) prepares post, and flow rate of mobile phase is 25mL/min,
UV-detector detection wavelength is 254nm, each sample introduction 200 μ L, and after collecting each sample introduction, chromatographic peak retains
The eluent that time is corresponding when being 16.7min, is evaporated after repeatedly adding up, obtains sesquialter of the present invention
Terpene crude compound；This crude product dissolves with pure methanol again, with pure methanol for flowing phase, uses Sephadex LH-20
Gel filtration chromatography purification can obtain this noval chemical compound of higher purity.
Embodiment 4
The compound of Example 1 preparation, for light yellow gum thing.
The structure of the sesquiterpenoids prepared by the present invention measures out by the following method.Of the present inventionization
Compound is light yellow gum thing；Ultraviolet spectra (solvent is methanol), λmax(log ε) 210 (3.18), 265 (3.35),
306(2.38)nm；Infrared spectrum (pressing potassium bromide troche) νmax3436,3087,2926,1625,1548,1465,
1346,1158,1037,892,783cm-1；High resolution mass spectrum (HRESIMS) provides quasi-molecular ion peak
m/z 267.1366[M+Na]+(value of calculation 267.1361).In conjunction with1H and13C H NMR spectroscopy provides a molecule
Formula C16H20O2, degree of unsaturation is 7.Its infrared spectrum shows hydroxyl (3436cm-1) and phenyl ring 1625,
1548,1465cm-1) functional group；Ultraviolet spectra has strong absorption at 265 and 306nm, also confirms that chemical combination
Thing exists conjugated structure.From1H and13CNMR spectrum (attribution data is shown in Table-1) signal can be seen that in compound
There are a 2,4,8,9-quaternary indenes parent nucleus, isobutenyl, two methylols, methoxyl groups.Root
According to the HMBC of H-3 and C-2, C-4, C-1, C-5, and H-6 with C-4 relevant (figure-3) susceptible of proof
Compound exists indenes parent nucleus.After the parent nucleus of compound determines, remaining isobutenyl, methylol and methoxyl group
For the substituent group on parent nucleus.HMBC relevant susceptible of proof isobutene. according to H-10 with C-1, C-2 with C-3
Base is substituted in the C-2 position of parent nucleus；It is substituted in parent nucleus according to H-14 and C-3, C-4 and C-5 susceptible of proof methylol
C-4, be substituted in parent nucleus according to the HMBC of H-15 with C-7, C-8 with C-9 relevant susceptible of proof methyl
C-8 position；Relevant with the HMBC of C-9 according to methoxyl group hydrogen, it can be verified that methoxy substitution is at the C-9 of parent nucleus
Position.So far the structure of this compound is determined.
Embodiment 5
The compound of Example 2 preparation, for yellow jelly.Assay method is the same as in Example 4, really
The compound recognizing embodiment 2 preparation is described sesquiterpenoids Nicotiana tabacum L. sesquiterpene-F.
Embodiment 6
The compound of Example 3 preparation, for yellow jelly.Assay method is the same as in Example 4, really
The compound recognizing embodiment 3 preparation is described Nicotiana tabacum L. sesquiterpene-F.
Embodiment 7
Arbitrary sesquiterpenoids prepared by Example 1-3 carries out activity of resisting tobacco mosaic virus test, examination
Test situation as follows:
Using half leaf method, the mass concentration at medicament carries out anti-Nicotiana tabacum L. to the compounds of this invention when being 50mg/L
Mosaic virus determination of activity.5～6 age flue-cured tobacco plant on, choose be applicable to test blade (leaf row is normal,
Anosis without worm), first blade is uniformly sprinkled fine emery powder, with brush pen by standby tobacco mosaic virus (TMV) source
(3.0×10-3) be uniformly put on sprinkled with on the blade of corundum, connect after poison terminates until the blade of all middle choosings, immediately
It is placed on to fill and the culture dish of medicinal liquid processes 20min, take out, wipe the globule and medicinal liquid on blade, by two
Half leaf restores and is emitted in the glass jar being covered with toilet paper moisturizing, and covers glass cover, temperature control (23 ± 2) DEG C,
It being placed on greenhouse natural light irradiation, 2～3d the most visible withered speckles. each process sets second half leaf as compareing, separately
It is externally provided with process that 1 group is commodity Ningnanmycin as a comparison, presses formula and calculate 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 soaks
In medicinal liquid, half connects the withered spot number (individual) of poison leaf.
The relative inhibition of bright compound of result is 33.6%%, exceedes the relative inhibition of comparison Ningnanmycin
31.5%, illustrate that compound has good activity of resisting tobacco mosaic virus.
Claims (4)
1. a sesquiterpenoids with following structural formula:
The named Nicotiana tabacum L. sesquiterpene-F of this compound, its molecular formula is C16H20O2。
2. the method preparing sesquiterpenoid described in claim 1 by supercritical fluid chromatography,
The method comprises the following steps:
(1) prepare tobacco extract extractum: with tobacco leaf as raw material, pulverized or be cut into segment, and
With the first solvent soaking and extract described Nicotiana tabacum L. 3～5 times, each 24h～72h, extracting solution is merged, filters
And obtain described tobacco extract extractum after concentrating；Wherein said first solvent is selected from methanol, ethanol or third
The organic solvent of ketone and the mixture of water, wherein organic solvent accounts for 60wt%～95wt% of this first solvent,
And first solvent: Nicotiana tabacum L.=2～4:1, weight ratio；
(2) silica gel column chromatography: by above-mentioned tobacco extract extractum with selected from pure methanol, straight alcohol or pure acetone
The second solvent dissolve after with the 60～120 mesh silica gel mixed samples of 0.8～1.2 times of weight for tobacco extract extractum,
Mixture after mixing sample 160～300 mesh silica gel with 2～4 times of weight for tobacco extract extractum again mix
Rear dry column-packing, is then followed successively by 1:0,20:1,9:1,8:2,7:3,6:4,1:1 and 1:2 by volume ratio
Chloroform-acetone solution carries out gradient elution, obtains during by chloroform-acetone solution eluting that wherein volume is 8:2
Eluent is referred to as the first eluent；
(3) supercritical fluid chromatography is isolated and purified: above-mentioned first eluent is passed through supercritical fluid chromatography and enters
Row is isolated and purified, and this supercritical fluid chromatography uses 10mm × 150mm, the Silica 2-EP chromatograph of 5 μm
Post, flowing is mutually for carbon dioxide that mass ratio is 90/10 and the mixture of methanol, and flow rate of mobile phase is 25
ML/min, UV-detector detection wavelength is 254nm, and the first each sample introduction of eluent 200～500 μ L receives
After integrating each sample introduction, chromatographic peak retention time is as eluent corresponding during 16.7min, the referred to as second eluent,
Described sesquiterpenoid is i.e. obtained after this second eluent desolvation.
Method the most according to claim 2, it also includes the step purified further below: will be in institute
State the described sesquiterpenoid that obtains after supercritical fluid chromatography separates and be again dissolved in methanol solution, and with
Methanol solution is flowing phase, carries out chromatography by gel column, mentions the described sesquiterpene of purification further
Compound.
Sesquiterpenoids the most according to claim 1 is in preparing resisting tobacco mosaic virus medicine
Purposes.
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| CN105906491B (en) * | 2016-04-20 | 2018-04-17 | 云南中烟工业有限责任公司 | A kind of drop sesquiterpenoids, its preparation method and its application in cigarette humectation |
| CN105837412B (en) * | 2016-04-20 | 2018-04-17 | 云南中烟工业有限责任公司 | A kind of sesquiterpenoids, its preparation method and its application in resisting tobacco mosaic virus medicine is prepared |
| CN106008219B (en) * | 2016-05-20 | 2018-04-17 | 云南中烟工业有限责任公司 | A kind of sesquiterpenoids, its preparation method and the application in anti-rotavirus medicaments are prepared |
| CN105949065B (en) * | 2016-05-20 | 2018-05-18 | 云南中烟工业有限责任公司 | A kind of sesquiterpenoids, its preparation method and its application in resisting tobacco mosaic virus drug is prepared |
| 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 |
| 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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| US4305411A (en) * | 1978-10-20 | 1981-12-15 | International Flavors & Fragrances Inc. | Acetyl hydrindacenes, acetyl indanes, mixtures of same, processes for preparing same and organoleptic uses thereof |
| US4209543A (en) * | 1978-10-20 | 1980-06-24 | International Flavors & Fragrances Inc. | Flavoring with a mixture of acetyl hydrindacenes |
| CN104945360B (en) * | 2015-06-25 | 2017-05-10 | 云南中烟工业有限责任公司 | Preparation method and application of phenylpropanoid compound in tobacco |
| CN104926772B (en) * | 2015-07-02 | 2017-05-17 | 云南中烟工业有限责任公司 | Novel flavonoid compound as well as preparation method and uses thereof |
| CN104974122B (en) * | 2015-07-02 | 2017-03-22 | 云南中烟工业有限责任公司 | Coumarin compound originated from tobacco, and preparation method and application thereof |
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