CN106117171A - A kind of supercritical fluid chromatography prepares the benzisoxa furfuran compound methods and applications in Nicotiana tabacum L. with antibacterial activity - Google Patents
A kind of supercritical fluid chromatography prepares the benzisoxa furfuran compound methods and applications in Nicotiana tabacum L. with antibacterial activity Download PDFInfo
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- CN106117171A CN106117171A CN201610493313.4A CN201610493313A CN106117171A CN 106117171 A CN106117171 A CN 106117171A CN 201610493313 A CN201610493313 A CN 201610493313A CN 106117171 A CN106117171 A CN 106117171A
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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
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
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- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H27/00—Special paper not otherwise provided for, e.g. made by multi-step processes
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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Abstract
The invention discloses a kind of benzisoxa furfuran compound, have a structure in whichThis compound named: 2 hydroxyl 1 isopentene group isobenzofuran 5 (3H) ketone.The invention also discloses the preparation method of described benzisoxa furfuran compound and the application in Medicated cigarette antibiotic package paper.
Description
Technical field
The invention belongs to technical field of tobacco chemistry, be specifically related to a kind of benzisoxa furan extracting first from Nicotiana tabacum L. and obtaining
Mutter compounds.Meanwhile, the invention still further relates to the preparation method of this compound and the application in antibiotic package paper.
Background technology
Nicotiana tabacum L. is the plant that chemical composition is the most complicated in the world, and secondary metabolite is the abundantest, according to nineteen eighty-two Dube
Reporting with Green etc., the chemical composition identified in Nicotiana tabacum L. is just more than 2549 kinds, by 2008, Rodgman and perfetti
Report, in Nicotiana tabacum L., tobacco and cigarette smoke find compound sum be about 8700 kinds.At present, people
The monomer chemistries material identifying out from Nicotiana tabacum L. is just more than kind more than 3000, and also has many compositions not yet to identify out.Cigarette
Grass, in addition to being mainly used in cigarette smoking purposes, also can therefrom extract the multiple chemical composition having value, therefrom be found to have out
Send out the guiding compound of value.
Furfuran compound exists in a lot of natural plants, and has multiple biological activity.According to the literature, such
Compound has antitumor, antioxidation, and Ca2+ influx blocks, angiotensin-ii receptor antagonism, adenosine A l receptor antagonist, anti-true
The pharmacological actions such as bacterium, antibacterial activity and platelet aggregation antagonism.Owing to Benzofurans compound has the pharmacology of such wide spectrum
Activity, this compounds is conducted in-depth research by domestic and international researcher, in addition to finding this compounds from natural product,
The compound with more excellent pharmacologically active is also obtained through structural modification.In order to study the structure activity relationship of this compounds, can
Research and develop more furfuran compound further, therefrom find effective lead compound and active group.The present invention
A kind of new benzisoxa furfuran compound of isolated from Yunnan Flue-cured Tobacco Nicotiana tabacum L., this compound it is not yet seen relevant
Report, it is worth mentioning at this point that this compound has significant antibacterial activity.
Summary of the invention
A first aspect of the present invention is to provide a kind of new benzisoxa furfuran compound.This compound is from cured tobacco leaf
Middle isolated, its molecular formula is C13H14O3, chemical identification by analysis, it has a structure in which
This compound is light yellow gum thing, and the present inventor is by named for its Chinese name 2-hydroxyl-1-isopentene group-different benzene
And furan-5 (3H)-one, English entitled 2-hydroxy-1-prenyl-isobenzofuran-5 (3H)-one.
Second aspect present invention provides the preparation method of the benzisoxa furfuran compound described in above-mentioned first aspect, should
Method comprises the steps:
(1) extractum extracts: with tobacco leaf as raw material, is pulverized or is cut into segment, with the first solvent soaking and extract
Described Nicotiana tabacum L. 3～5 times, each 24h～72h, obtain described tobacco extract extractum after being merged, filter and concentrate by extracting solution；
Wherein said first solvent is the methanol selected from concentration expressed in percentage by weight 80%～100% or ethanol, or concentration expressed in percentage by weight 60%
～the acetone of 90%, and the first solvent: Nicotiana tabacum L.=2～4:1, weight ratio；
(2) silica gel column chromatography: by second molten with selected from pure methanol, straight alcohol or pure acetone of above-mentioned tobacco extract extractum
Agent dissolve after with the 80～100 mesh silica gel mixed samples of 0.8～1.2 times of weight for tobacco extract extractum, the mixing after sample will be mixed
Thing 160～300 mesh silica gel with 2～4 times of weight for tobacco extract extractum again mix after dry column-packing, then use volume ratio
The a series of chloroform-acetone solution being followed successively by 1:0,20:1,9:1,8:2,7:3,6:4,1:1 and 1:2 carry out gradient elution, collect
The eluent obtained time wherein with the chloroform-acetone solution eluting that volume ratio is 7:3, the referred to as first eluent；
(3) supercritical fluid chromatography is isolated and purified: above-mentioned first eluent is passed through supercritical fluid chromatography and separates
Purification, this supercritical fluid chromatography uses 10mm × 150mm, the Silica 2-EP chromatographic column of 5 μm, and flow phase carbon dioxide/second
Alcohol (85/15, mass ratio), flow rate of mobile phase is 20mL/min, and UV-detector detection wavelength is 305nm, the first eluent liquid
Every time sample introduction 200～500 μ L, collects eluent corresponding when chromatographic peak retention time after each sample introduction is 11.5min, is referred to as
Second eluent, i.e. obtains described benzisoxa furfuran compound after this second eluent desolvation.
In preferred embodiments, present invention additionally comprises the step purified further below: will be at described shooting flow
The described benzisoxa furfuran compound obtained after body chromatographic isolation is again dissolved in methanol solution, and with methanol solution for flowing
Phase, carries out chromatography by gel column, with the most isolated and purified.
A third aspect of the present invention provides the application in antibiotic package paper of the described benzisoxa furan compound.
Accompanying drawing explanation
Fig. 1 is the carbon-13 nmr spectra of benzisoxa furfuran compound of the present invention；
Fig. 2 is the proton nmr spectra of benzisoxa furfuran compound of the present invention；
Fig. 3 is that the main HMBC of benzisoxa furfuran compound of the present invention is correlated with.
Detailed description of the invention
The structure of the benzisoxa furfuran compound that the present invention prepares is measured by the following method.For light yellow
Jelly；HR-ESI-MS shows that its quasi-molecular ion peak is 241.0832 [M+Na]+, in conjunction with1H-and13C-NMR spectrum determines molecule
Formula is C13H14O3, degree of unsaturation is 7.Its infrared spectrum display compound there is hydroxyl (3389cm-1), carbonyl (1715 Hes
1650cm-1), and aromatic ring (1610,1566 and 1467cm-1) signal, ultraviolet spectra has absorption maximum also in 305,272 and 210nm
Confirm compound exists aromatic ring structure.From1H and13Signal can be seen that in compound CNMR spectrum (attribution data is shown in Table-1) has
One 1,2,4,5-quaternary phenyl ring (δC126.0s, 159.2s, 111.2d, 144.7s, 116.4s and 130.2d；δH
6.74s and 7.78s), an isopentene group (δC27.2t, 124.2d, 133.3s, 17.6q and 25.8q；δH 3.27(d)6.8、
5.30 (t) 6.8,1.57s and 1.81s), one oxidation methylene (δC68.9t and δH5.52s), an ester carbonyl group (δC
168.6s), 1 phenolic hydroxyl group (δH10.44s).According to H2-1′(δH5.52) and C-2 ' (δC 168.6)、C-3(δC 111.2)、
C-4(δC 144.7)、C-5(δC116.4), H-3 (δH6.74) and C-1 (δC, and H-6 (δ 111.2)H7.78) and C-2 '
(δC168.6) HMBC susceptible of proof compound of being correlated with is lipoid substance [6] in isobenzofuran, C-1' and C-2' passes through oxygen
Atom constitutes lactone ring five membered.After the precursor skeleton of compound is confirmed, the position of other substituted radicals also can lead to
Cross the relevant confirmation of HMBC；According to H-8 (δH5.30) and C-1 (δC126.0), H-7 (δH3.27) and C-1 (δC 126.0)、C-2
(δC 159.2)、C-6(δC, and H-6 (δ 130.2)H7.78) and C-7 (δC27.2) HMBC is correlated with susceptible of proof iso-amylene
Base is connected to-1 of phenyl ring, according to phenolic hydroxyl group hydrogen (δH10.44) and C-1 (δC 126.0)、C-2(δC159.2) and C-3 (δC
111.2) HMBC susceptible of proof phenolic hydroxyl group of being correlated with is substituted in C-2 position.So far (1) structure of compound is determined, this compound
Named 2-hydroxyl-1-isopentene group-isobenzofuran-5 (3H)-one.
Infrared, the ultraviolet of compound and mass spectrometric data:: for light yellow gum thing；UV (MeOH), λmax(logε)305
(2.60)、272(3.43)、210(3.86)nm；IR(KBr)λmax 3389、3086、2953、1715、1650、1610、1566、
1467,1352,1278,1156,1055,920 and 775cm-1；ESIMS (positive ion mode) m/z 241 [M+Na]+；HRESIMS
(positive ion mode) m/z 241.0832 [M+Na]+(value of calculation 241.0841, C13H14NaO3)。
(solvent is C to the nuclear magnetic resonance data of table-1 compound (1)5D5N)
The compounds of this invention is separated first, by above-mentioned nuclear magnetic resonance, NMR and measuring method of mass spectrum determine into
Benzisoxa furfuran compound, and characterize its concrete structure.This compound has been carried out Antimicrobial Screening, and it is to golden yellow
Staphylococcus, escherichia coli, angstrom uncommon bacterium, bacillus subtilis, a Bacillus proteus etc. have significant activity.
This compound is applied in cigarette tipping paper, compares with comparison, and the tipping paper detection adding this compound is thin
Bacterium sum, coliform, staphylococcus aureus, bacillus pyocyaneus, Hemolytic streptococcus, total number of fungi substantially reduce；To large intestine
Bacillus (ATCC25922), the bacteriostasis rate of staphylococcus aureus (ATCC6538) entirely reach more than 92.2%, it is possible to reduce or
Eliminate cigarette tipping paper and in storage process bacteria breed and the probability of breeding, it addition, at smoking property of cigarette, transmittance process
In, this antibacterial action also is able to microorganism contaminated to the tipping paper on Cigarette and plays inhibitory action.
Compared with prior art, the present invention has advantage highlighted below: the raw materials of compound of (1) present invention is easy to get, and extracts
Method is simple, can be easily separated and obtains；Molecular structure is also simple, easily realizes synthetic.(2) have employed conventional column chromatography and height
The preparation method that effect liquid phase chromatogram combines, compound preparation manipulation flow process is simple, and the compounds of this invention purity obtained is high, after
Continuous industrialized production easily realizes.(3) the compounds of this invention is nontoxic to animal, uses safety, shows good antibacterial work
Property, the bacteriostasis rate of escherichia coli, staphylococcus aureus etc. is entirely reached more than 92.2%；It is applied to cigarette tipping paper, energy
Inhibitory action is played in enough microorganisms contaminated to cigarette tipping paper.Directly and oral contact, this compound exists cigarette tipping paper
Use in cigarette tipping paper can be avoided at Medicated cigarette sucking, microbial contamination in transmittance process, is effectively increased Medicated cigarette
Health and safety.
Raw tobacco material used by the present invention is not limited by area and kind, all can realize the present invention, below to derive from cloud
The raw tobacco material of cigarette industry Co., Ltd different sources in south, the present invention will be further described.Except as otherwise noted, originally
Percent employed in invention is mass percent.
Embodiment 1
Prepare benzisoxa furfuran compound C13H14O3, divide including extractum extraction, silica gel column chromatography, supercritical fluid chromatography
From, specifically use following steps:
(1) extractum extracts: with tobacco leaf as raw material, is pulverized or is cut into segment, with the first solvent soaking and extract
Described Nicotiana tabacum L. 3～5 times, each 24h～72h, obtain described tobacco extract extractum after being merged, filter and concentrate by extracting solution；
Wherein said first solvent is the methanol selected from concentration expressed in percentage by weight 80%～100% or ethanol, or concentration expressed in percentage by weight 60%
～the acetone of 90%, and the first solvent: Nicotiana tabacum L.=2～4:1, weight ratio；
(2) silica gel column chromatography: by second molten with selected from pure methanol, straight alcohol or pure acetone of above-mentioned tobacco extract extractum
Agent dissolve after with the 80～100 mesh silica gel mixed samples of 0.8～1.2 times of weight for tobacco extract extractum, the mixing after sample will be mixed
Thing 160～300 mesh silica gel with 2～4 times of weight for tobacco extract extractum again mix after dry column-packing, then use volume ratio
The a series of chloroform-acetone solution being followed successively by 1:0,20:1,9:1,8:2,7:3,6:4,1:1 and 1:2 carry out gradient elution, collect
The eluent obtained time wherein with the chloroform-acetone solution eluting that volume ratio is 7:3, the referred to as first eluent；
(3) supercritical fluid chromatography is isolated and purified: above-mentioned first eluent is passed through supercritical fluid chromatography and separates
Purification, this supercritical fluid chromatography uses 10mm × 150mm, the Silica 2-EP chromatographic column of 5 μm, and flow phase carbon dioxide/second
Alcohol (85/15, mass ratio), flow rate of mobile phase is 20mL/min, and UV-detector detection wavelength is 305nm, the first eluent liquid
Every time sample introduction 200～500 μ L, collects eluent corresponding when chromatographic peak retention time after each sample introduction is 11.5min, is referred to as
Second eluent, i.e. obtains described benzisoxa furfuran compound after this second eluent desolvation.
In preferred embodiments, present invention additionally comprises the step purified further below: will be at described shooting flow
The described benzisoxa furfuran compound obtained after body chromatographic isolation is again dissolved in methanol solution, and with methanol solution for flowing
Phase, carries out chromatography by gel column, with the most isolated and purified.
Embodiment 2
Tobacco sample derives from Yunnan Yuxi, and kind is Yuxi K326.Nicotiana tabacum L. is sampled 2.0kg and pulverizes the methanol with 95%
Extracting 5 times, extract 24h every time, extracting solution merges, and filters, and concentrating under reduced pressure becomes extractum, obtains extractum 105g.Extractum weight ratio 2.0
The pure methanol of times amount carries out silica gel column chromatography with the 100 thick silica gel mixed samples of mesh of 120g, the 160 mesh silica gel dress posts of 0.6kg after dissolving,
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 phase
With part, obtain 8 parts, wherein volume proportion is that the chloroform-acetone elution fraction supercritical fluid chromatography of 7:3 is carried out
Isolated and purified, this supercritical fluid chromatography uses 10mm × 150mm, the Silica 2-EP chromatographic column of 5 μm, and flow phase titanium dioxide
Carbon/ethanol (85/15, mass ratio), flow rate of mobile phase is 20mL/min, and UV-detector detection wavelength is 305nm, each sample introduction
200 μ L, collect eluent corresponding when chromatographic peak retention time after each sample introduction is 11.5min, by eluent desolvation
After i.e. obtain described benzisoxa furfuran compound.Products therefrom dissolves with pure methanol again, then with pure methanol for flowing phase, uses
Sephadex LH-20 gel filtration chromatography separates, and obtains this noval chemical compound.
Embodiment 3
Tobacco sample derives from Dali, and kind is cloud and mist 200, Nicotiana tabacum L. samples 3.5kg chopping, with the ethanol of 95%
Extracting 4 times, extract 48h every time, extracting solution merges, and filters, and concentrating under reduced pressure becomes extractum, obtains extractum 250g.Extractum weight ratio 2.0
The pure methanol of times amount carries out silica gel column chromatography with the 80 thick silica gel mixed samples of mesh of 250g, the 200 mesh silica gel dress posts of 1.2kg after dissolving,
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 phase
With part, obtain 8 parts, wherein volume proportion is that the chloroform-acetone elution fraction supercritical fluid chromatography of 7:3 is carried out
Isolated and purified, this supercritical fluid chromatography uses 10mm × 150mm, the Silica 2-EP chromatographic column of 5 μm, and flow phase titanium dioxide
Carbon/ethanol (85/15, mass ratio), flow rate of mobile phase is 20mL/min, and UV-detector detection wavelength is 305nm, each sample introduction
200 μ L, collect eluent corresponding when chromatographic peak retention time after each sample introduction is 11.5min, by eluent desolvation
After i.e. obtain described benzisoxa furfuran compound.Products therefrom dissolves with pure methanol again, then with pure methanol for flowing phase, uses
Sephadex LH-20 gel filtration chromatography separates, and obtains this noval chemical compound.
Embodiment 4
Tobacco sample derives from Kunming, Yunnan, and kind is the big gold dollar of Flos Carthami, Nicotiana tabacum L. is sampled 5kg pulverize, with 75% third
Ketone supersound extraction 3 times, extracts 72h every time, and extracting solution merges, and filters, and concentrating under reduced pressure becomes extractum, obtains extractum 380g.Extractum is used
The pure methanol of weight ratio 1.6 times amount carries out silicon with the 90 thick silica gel mixed samples of mesh of 400g, the 180 mesh silica gel dress posts of 2.4kg after dissolving
Plastic 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, obtains 8 parts, and wherein volume proportion is the chloroform-acetone elution fraction shooting flow of 7:3
Body colour spectrum carries out isolated and purified, and this supercritical fluid chromatography uses 10mm × 150mm, the Silica 2-EP chromatographic column of 5 μm, stream
Dynamic phase carbon dioxide/ethanol (85/15, mass ratio), flow rate of mobile phase is 20mL/min, and UV-detector detection wavelength is
305nm, each sample introduction 200 μ L, collect eluent corresponding when chromatographic peak retention time after each sample introduction is 11.5min, will
Described benzisoxa furfuran compound is i.e. obtained after eluent desolvation.Products therefrom dissolves with pure methanol again, then with pure first
Alcohol is flowing phase, separates with Sephadex LH-20 gel filtration chromatography, obtains this noval chemical compound.
Embodiment 5
The qualification of------compound structure
Compound prepared by Example 1-4, the structure of the benzisoxa furfuran compound that method described above prepares
It is measured by the following method.Compound is light yellow gum thing；HR-ESI-MS shows that its quasi-molecular ion peak is
241.0832[M+Na]+, in conjunction with1H-and13C-NMR spectrum determines that molecular formula is C13H14O3, degree of unsaturation is 7.Its infrared spectrum shows
Show that compound has hydroxyl (3389cm-1), carbonyl (1715 and 1650cm-1), and aromatic ring (1610,1566 and 1467cm-1) letter
Number, ultraviolet spectra has absorption maximum to also confirm that in compound in 305,272 and 210nm to there is aromatic ring structure.From1H and13CNMR composes
(attribution data is shown in Table-1) signal can be seen that a 1,2,4,5-quaternary phenyl ring (δ in compoundC 126.0s、
159.2s, 111.2d, 144.7s, 116.4s and 130.2d；δH6.74s and 7.78s), an isopentene group (δC 27.2t、
124.2d, 133.3s, 17.6q and 25.8q；δH3.27 (d) 6.8,5.30 (t) 6.8,1.57s and 1.81s), one oxidation Asia
Methyl (δC68.9t and δH5.52s), an ester carbonyl group (δC168.6s), 1 phenolic hydroxyl group (δH10.44s).According to H2-1′
(δH5.52) and C-2 ' (δC168.6)、C-3(δC 111.2)、C-4(δC 144.7)、C-5(δC116.4), H-3 (δH 6.74)
With C-1 (δC, and H-6 (δ 111.2)H7.78) and C-2 ' (δC168.6) HMBC susceptible of proof compound of being correlated with is different benzo
Lipoid substance [6] in furan, C-1' and C-2' constitutes lactone ring five membered by oxygen atom.The precursor skeleton of compound
After being confirmed, the position of other substituted radicals also can confirm by HMBC is relevant；According to H-8 (δH5.30) and C-1 (δC
126.0), H-7 (δH3.27) and C-1 (δC126.0)、C-2(δC 159.2)、C-6(δC, and H-6 (δ 130.2)H 7.78)
With C-7 (δC27.2) HMBC susceptible of proof isopentene group of being correlated with is connected to-1 of phenyl ring, according to phenolic hydroxyl group hydrogen (δH 10.44)
With C-1 (δC 126.0)、C-2(δC159.2) and C-3 (δC111.2) HMBC susceptible of proof phenolic hydroxyl group of being correlated with is substituted in C-2 position.
So far (1) structure of compound is determined, this Compound nomenclature be 2-hydroxyl-1-isopentene group-isobenzofuran-5 (3H)-
Ketone.
Embodiment 6
The compound of Example 3 preparation, for yellow jelly.Assay method is same as in Example 5, confirms embodiment 3
The compound of preparation be described benzisoxa furfuran compound 2-hydroxyl-1-isopentene group-isobenzofuran-5 (3H)-
Ketone.
Embodiment 7
The compound of Example 4 preparation, for yellow jelly.Assay method is same as in Example 5, confirms embodiment 4
The compound of preparation is described 2-hydroxyl-1-isopentene group-isobenzofuran-5 (3H)-one.
Embodiment 8
Prepared by Example 1-4 appoints benzisoxa furfuran compound to carry out antibacterial activity test, and test situation is as follows:
Antimicrobial test agar diffusion method is carried out, and first tested bacterium is coated in plain agar culture medium (cattle equably
Meat extract, peptone, sodium chloride, serum, agar) flat board on, then by testing compound (benzofuran C prime compound 10mL
DMSO dissolves, and dilute becomes the solution of 50 μ g/mL) soaked tablet (diameter 5mm) is placed in the culture medium carried disease germs, puts into
In calorstat, after hatching 24-72h in 25 DEG C, observe inhibition zone size.Result shows: the compounds of this invention is to Staphylococcus aureus
Bacterium, escherichia coli, angstrom uncommon bacterium, bacillus subtilis, a Bacillus proteus etc. have the strongest activity；Suppression ratio is more than 92.2%.
Embodiment 9
The compounds of this invention is carried out safety evaluatio, has been tested and TK gene by Micronuclei In The Mouse Bone Marrow experiment, Ames
Mutating experiment, it was demonstrated that the compounds of this invention is nontoxic to animal, uses safety.This compound is added to Medicated cigarette with the concentration of 50 μ g/mL
On tipping paper；By the detection method of the People's Republic of China's " Disposable Sanitary Accessory sanitary standard " GB15979-2002,
Take the volume cigarette tipping paper adding the compounds of this invention, 2.0 × 3.0mm size, detect total number of bacteria, coliform, golden yellow
Staphylococcus, bacillus pyocyaneus, Hemolytic streptococcus, total number of fungi.Result shows, adds the tipping paper bacterium of the compounds of this invention
The sum that falls significantly reduces, and this compound has obvious inhibiting effect to the antibacterial of several tests, to escherichia coli, golden yellow Fructus Vitis viniferae
The bacteriostasis rate of coccus etc. entirely reaches more than 92.2%.
Claims (4)
1. a benzisoxa furfuran compound, it is characterised in that have a structure in which
This compound named: 2-hydroxyl-1-isopentene group-isobenzofuran-5 (3H)-one.
2. the preparation method of a benzisoxa furan compound according to claim 1, it is characterised in that the method includes
Following steps:
(1) extractum extracts: with tobacco leaf as raw material, is pulverized or is cut into segment, described with the first solvent soaking extraction
Nicotiana tabacum L. 3～5 times, each 24h～72h, obtain described tobacco extract extractum after being merged, filter and concentrate by extracting solution；Wherein
Described first solvent is the methanol selected from concentration expressed in percentage by weight 80%～100% or ethanol, or concentration expressed in percentage by weight 60%～
The acetone of 90%, and the first solvent: weight ratio=2 of Nicotiana tabacum L.～4:1；
(2) silica gel column chromatography: by step (1) described tobacco extract extractum with selected from the of pure methanol, straight alcohol or pure acetone
80～100 mesh silica gel mixed samples of 0.8～1.2 times of weight after two solvents dissolve and for tobacco extract extractum, after mixing sample
Mixture 160～300 mesh silica gel with 2～4 times of weight for tobacco extract extractum again mix after dry column-packing, then use body
A series of chloroform-acetone solution that long-pending ratio is followed successively by 1:0,20:1,9:1,8:2,7:3,6:4,1:1 and 1:2 carry out gradient elution,
The eluent obtained when collecting wherein with the chloroform-acetone solution eluting that volume ratio is 7:3, the referred to as first eluent；
(3) supercritical fluid chromatography is isolated and purified: the first eluent that step (2) obtains is passed through supercritical fluid chromatography and carries out
Isolated and purified, this supercritical fluid chromatography uses 10mm × 150mm, the Silica 2-EP chromatographic column of 5 μm, and flow phase titanium dioxide
Carbon/ethanol (85/15, mass ratio), flow rate of mobile phase is 20mL/min, and UV-detector detection wavelength is 305nm, the first eluting
The each sample introduction of liquid liquid 200～500 μ L, collects eluent corresponding when chromatographic peak retention time after each sample introduction is 11.5min,
It is referred to as the second eluent, after this second eluent desolvation, i.e. obtains described benzisoxa furfuran compound.
Preparation method the most according to claim 2, it is characterised in that in described step (3), supercritical fluid chromatography separates
Compound after purification dissolves with pure methanol again, then with pure methanol for flowing phase, separates with gel filtration chromatography, to divide further
From purification.
The benzisoxa furfuran compound the most according to claim 1 application in Medicated cigarette antibiotic package paper.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610493313.4A CN106117171B (en) | 2016-06-29 | 2016-06-29 | It is a kind of that the benzisoxa furfuran compound methods and applications in tobacco with antibacterial activity are prepared with supercritical fluid chromatography |
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|---|---|---|---|
| CN201610493313.4A CN106117171B (en) | 2016-06-29 | 2016-06-29 | It is a kind of that the benzisoxa furfuran compound methods and applications in tobacco with antibacterial activity are prepared with supercritical fluid chromatography |
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| CN106117171A true CN106117171A (en) | 2016-11-16 |
| CN106117171B CN106117171B (en) | 2018-05-25 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106858710A (en) * | 2017-04-01 | 2017-06-20 | 云南中烟工业有限责任公司 | It is a kind of to improve benzisoxa furfuran compound of cigarette smoking effect and preparation method and application |
| CN106883245A (en) * | 2017-04-01 | 2017-06-23 | 云南中烟工业有限责任公司 | A kind of benzisoxa furfuran compound with removing free radical effect and preparation method and application |
| CN106916131A (en) * | 2017-02-14 | 2017-07-04 | 云南民族大学 | The preparation method and its pharynx-clearing throat-benefiting effect of the isobenzofuran class compound in a kind of root of kudzu vine |
| CN115772173A (en) * | 2022-12-20 | 2023-03-10 | 武汉国粹医药科技有限公司 | Benzofuran compound, preparation method and application thereof, and antibacterial agent |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104945360A (en) * | 2015-06-25 | 2015-09-30 | 云南中烟工业有限责任公司 | Preparation method and application of phenylpropanoid compound in tobacco |
| CN105001186A (en) * | 2015-06-25 | 2015-10-28 | 云南中烟工业有限责任公司 | Preparation method and application of isopentenyl benzolactone compound in tobacco |
| CN105017190A (en) * | 2015-06-25 | 2015-11-04 | 云南中烟工业有限责任公司 | Preparation method and use of benzolactone compound in tobacco |
-
2016
- 2016-06-29 CN CN201610493313.4A patent/CN106117171B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104945360A (en) * | 2015-06-25 | 2015-09-30 | 云南中烟工业有限责任公司 | Preparation method and application of phenylpropanoid compound in tobacco |
| CN105001186A (en) * | 2015-06-25 | 2015-10-28 | 云南中烟工业有限责任公司 | Preparation method and application of isopentenyl benzolactone compound in tobacco |
| CN105017190A (en) * | 2015-06-25 | 2015-11-04 | 云南中烟工业有限责任公司 | Preparation method and use of benzolactone compound in tobacco |
Non-Patent Citations (2)
| Title |
|---|
| AU SHEN 等: "Phenylpropanoids from the leaves of Nicotiana tabacum and their anti-tobacco mosaic virus activities", 《HETEROCYCLES》 * |
| 董伟 等: "傣药竹叶兰中1 个新苯丙素及其抗烟草花叶病毒活性", 《中草药》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106916131A (en) * | 2017-02-14 | 2017-07-04 | 云南民族大学 | The preparation method and its pharynx-clearing throat-benefiting effect of the isobenzofuran class compound in a kind of root of kudzu vine |
| CN106858710A (en) * | 2017-04-01 | 2017-06-20 | 云南中烟工业有限责任公司 | It is a kind of to improve benzisoxa furfuran compound of cigarette smoking effect and preparation method and application |
| CN106883245A (en) * | 2017-04-01 | 2017-06-23 | 云南中烟工业有限责任公司 | A kind of benzisoxa furfuran compound with removing free radical effect and preparation method and application |
| CN106858710B (en) * | 2017-04-01 | 2018-03-09 | 云南中烟工业有限责任公司 | A kind of benzisoxa furfuran compound that can improve cigarette smoking effect and preparation method and application |
| CN115772173A (en) * | 2022-12-20 | 2023-03-10 | 武汉国粹医药科技有限公司 | Benzofuran compound, preparation method and application thereof, and antibacterial agent |
| CN115772173B (en) * | 2022-12-20 | 2024-04-16 | 武汉国粹医药科技有限公司 | Benzofuran compound, preparation method and application thereof, and antibacterial agent |
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| CN106117171B (en) | 2018-05-25 |
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