CN105753823B - A kind of purposes in 2 arylbenzofuran class compound, its preparation method and cigarette antibiotic package paper - Google Patents
A kind of purposes in 2 arylbenzofuran class compound, its preparation method and cigarette antibiotic package paper Download PDFInfo
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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
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
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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
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/36—Biocidal agents, e.g. fungicidal, bactericidal, insecticidal agents
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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
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- 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 2 arylbenzofuran class compounds, it has following structures：The compound is named as the dimethyl benzofuran of 7 methoxyl group 2 (4 methoxyphenyl) 3,5, and its molecular formula is C18H18O3.The invention also discloses the preparation method of 2 arylbenzofuran class compounds and the purposes in cigarette antibiotic package paper.
Description
Technical field
The invention belongs to technical field of tobacco chemistry, and in particular to a kind of 2- aryl benzene for extracting to obtain first from tobacco
Benzofuran compound.Meanwhile the application the invention further relates to the preparation method of the compound and in antibiotic package paper.
Background technology
Tobacco is the plant that chemical composition is the most complicated in the world, and secondary metabolite is very abundant, according to nineteen eighty-two Dube
To be reported with Green etc., the chemical composition identified in tobacco is just more than 2549 kinds, by 2008, Rodgman and perfetti
Report, the compound that is found in tobacco, tobacco and cigarette smoke sum is about 8700 kinds.At present, people
The monomer chemistries material come the just kind more than 3000 is identified from tobacco, and also many compositions are not yet identified and.Cigarette
Grass can also therefrom extract a variety of chemical compositions for having value in addition to cigarette smoking purposes is mainly used in, and therefrom find have out
Send out the guiding compound of value.
Furfuran compound exists in many natural plants, and has multiple biological activities.According to the literature, such
Compound have it is antitumor, it is anti-oxidant, Ca2+ influx retardance, angiotensin-ii receptor antagonism, adenosine A l receptor antagonists, resist true
The pharmacological actions such as bacterium, antibacterial activity and platelet aggregation antagonism.Because Benzofurans compound has the pharmacology of such wide spectrum
Activity, domestic and international researcher conduct in-depth research to such compound, in addition to such compound is found from natural products,
The compound with more excellent pharmacological activity is also obtained by structural modification., can in order to study the structure-activity relationship of this kind of compound
More furfuran compounds are further researched and developed, therefrom find effective lead compound and active group.
The content of the invention
The present invention a kind of isolated 2- arylbenzofurans class compound, the chemical combination from Yunnan Flue-cured Tobacco tobacco leaf first
Relevant report is not yet seen in thing, it is worth mentioning at this point that the compound has significant antibacterial activity.
First aspect present invention is related to a kind of 2- arylbenzofurans class compound, it is characterised in that has following structures：
The compound is named as 7- methoxyl groups -2- (4- methoxyphenyls) -3,5- dimethyl benzofurans, its molecular formula
For C18H18O3；English entitled [7-methoxy-2- (4-methoxyphenyl) -3,5-dimethylbenzofuran], the change
Compound is light yellow gum thing.
Second aspect of the present invention is related to the preparation method of described 2- arylbenzofuran compounds, and this method includes following
Step：
(1) medicinal extract extracts：Using tobacco leaf as raw material, crushed with the first solvent soaking and extract the tobacco 3~5
It is secondary, each 24h~72h, extract solution is merged, filtered and the tobacco extract medicinal extract is obtained after concentrating；Wherein described first
Solvent is the mixture selected from methanol, the organic solvent of ethanol or acetone and water, and wherein organic solvent accounts for first solvent
60wt%~100wt%, and the first solvent：The weight ratio of tobacco is 2~4:1；
(2) silica gel column chromatography：The tobacco extract medicinal extract that step (1) is obtained is used selected from pure methanol, straight alcohol or pure third
Silica gel mixed sample after the second solvent dissolving of ketone with 60~120 mesh of 1~1.6 times of weight for tobacco extract medicinal extract, will be mixed
Dry column-packing after mixture after sample mixes with 160~300 mesh silica gel of 2~4 times of weight for tobacco extract medicinal extract again, so
Afterwards 10 are followed successively by with volume ratio:0、9:1、8:2、7:3、6:4 and 5:A series of 5 chloroform-acetone solutions carry out gradient elution, receive
Collection is 8 wherein with volume ratio:The eluent obtained during 2 chloroform-acetone solution elution, referred to as the first eluent；
(3) supercritical fluid chromatography separates：The first eluent that step (2) obtains is passed through into supercritical fluid chromatography to carry out
Separation, the supercritical fluid chromatography use 10mm × 150mm, 5 μm of Silica 2-EP chromatographic columns, mobile phase for carbon dioxide/
Ethanol (90/10, mass ratio), flow rate of mobile phase 20mL/min, UV-detector Detection wavelength are 312nm, the first eluent
Each μ L of sample introduction 200~500, eluent corresponding when chromatographic peak retention time after each sample introduction be 10.4min is collected, referred to as
Second eluent, described 2- arylbenzofuran class compounds will be produced after the second eluent desolvation.
In preferred embodiments, the step of described preparation method also includes purifying further below：Will be described
The 2- arylbenzofurans class compound that supercritical fluid chromatography separation obtains afterwards is again dissolved in methanol solution, and with first
Alcoholic solution is mobile phase, carries out chromatography by gel column, mentions the 2- arylbenzofurans class further purified
Compound.
Third aspect present invention is related to described 2- arylbenzofurans compound and is used in cigarette antibiotic package paper
Purposes.
Beneficial effects of the present invention：
1st, the present invention a kind of isolated 2- arylbenzofurans class compound, change from Yunnan Flue-cured Tobacco tobacco leaf first
Compound is there is not yet relevant report；The raw materials of compound of the present invention is easy to get, and extracting method is simple, can be easily separated to obtain；Molecule knot
Structure is also simple, easily realizes artificial synthesized.The compounds of this invention purity obtained is high, and follow-up industrialized production is easily real
It is existing；
2nd, compound of the invention, shows, it has preferable bacteriostasis and preferable antibacterial activity through active testing；
And it is nontoxic to animal, it is safe to use, good antibacterial activity is shown, to the antibacterial of Escherichia coli, staphylococcus aureus etc.
Rate entirely reaches more than 93%；
3rd, compound of the invention is used in cigarette tipping paper, can eliminate or reduce in cigarette tipping paper bacteria breed and
The possibility of breeding, can avoid cigarette suck, microbial contamination in transmittance process, effectively increase cigarette health and peace
Quan Xing.
Brief description of the drawings
Fig. 1 is the carbon-13 nmr spectra of the 2- arylbenzofuran class compounds of the present invention；
Fig. 2 is the proton nmr spectra of the 2- arylbenzofuran class compounds of the present invention；
Fig. 3 is that the main HMBC of the 2- arylbenzofuran class compounds of the present invention is related.
Fig. 4 is the structure chart of the 2- arylbenzofuran class compounds of the present invention.
Embodiment
The structure for the 2- arylbenzofuran class compounds that the present invention is prepared is measured by the following method.This hair
Bright compound is light yellow gum thing；Ultraviolet spectra (MeOH), λmax(logε)210(4.05)、270(3.08)、312(3.38)
Nm, infrared spectrum (KBr tablettings) λmax 3028、2984、1618、1476、1428、1380、1158、1061、895、784cm-1,
ESIMS (cation collection) m/z 305 [M+Na]+；HRESIMS (cation collection) m/z 305.1162 [M+Na]+Calculated value
305.1154, C18H18NaO3).With reference to1H and13C H NMR spectroscopies determine that molecular formula is C18H18O3, degree of unsaturation 10.Ultraviolet spectra
There is absorption maximum to confirm aromatic ring structure be present in compound in 210,270,312nm.Compound1H、13C NMR and DEPT data
(table -1) shows in compound 18 carbon and 18 hydrogen be present, comprising 11,2,3,5- quaternary phenyl ring (C-1~C-6, H-4
And H-6), phenyl ring (C-1'~C-6', the H of 1 Isosorbide-5-Nitrae-substituted2- 2', 6', and H2- 3', 5'), two methyl (C-7 and C-9',
H3- 7 and H3- 9'), one group of double bond (C-7 and C-8), and 2 methoxyl group (δC56.1 and 55.9q, δH3.85 and 3.81s).Root
According to nuclear magnetic resonance data in compound (two phenyl ring, C-7 '~C-9 ', and H3- 9 ') and known compound methoxy-4 '-
Hydroxy)-aryl-3-methy-6-hydroxybenzofuran is similar, can initial guess compound (1) may be 3- first
Base -2- arylbenzofurans.In addition, compound (1), which is 3- methyl -2- arylbenzofurans, can further pass through H3- 9 ' and C-
1st, C-7 ' and C-8 ', H2- 2 ', 6 ' and C-7 ', and H-6 (figure -2) related to C-8 ' HMBC are confirmed.The bone of compound
After frame is confirmed, remaining substituted radical, methyl (C-7), which is substituted in C-5 positions, can pass through H3- 7 and C-4, C-5 and C-6, H-4
And C-7, and H-6 determinations related to C-7 HMBC；Two methoxy substitutions can lead to two methoxyl group hydrogen in C-3 and C-4 ' positions
(δH3.81) and C-3 (δ 3.85 andCAnd C-4 ' (δ 151.7)C160.6) HMBC is related to be confirmed.
Nuclear magnetic resonance data (the solvent C of the compound of table -1 (1)5D5N)
The compounds of this invention is separated first, by above-mentioned nuclear magnetic resonance and measuring method of mass spectrum determine for
2- arylbenzofuran compounds, and characterize its concrete structure.Antimicrobial Screening is carried out to the compound, it is to golden yellow
Color staphylococcus, Escherichia coli, angstrom uncommon bacterium, hay bacillus, proteus etc. have significant activity.
The compound is applied in cigarette tipping paper, is compared with control, and the tipping paper detection for adding this compound is thin
Bacterium sum, coliform, staphylococcus aureus, Pseudomonas aeruginosa, hemolytic streptococcus, total number of fungi substantially reduce；To large intestine
Bacillus (ATCC25922), the bacteriostasis rate of staphylococcus aureus (ATCC6538) entirely reach more than 93%, can reduce or disappear
Bacteria breed and the possibility of breeding except cigarette tipping paper and in storage process, in addition, in smoking property of cigarette, transmittance process,
The antibacterial action also can play inhibitory action to the contaminated microorganism of tipping paper on Cigarette.
Compared with prior art, the present invention has advantage following prominent：(1) raw materials of compound of the invention is easy to get, and extracts
Method is simple, can be easily separated to obtain；Molecular structure is also simple, easily realizes artificial synthesized.(2) conventional column chromatography and height are employed
The preparation method that effect liquid phase chromatogram combines, compound preparation manipulation flow is simple, and the compounds of this invention purity obtained is high, after
Continuous industrialized production is easily realized.(3) the compounds of this invention is nontoxic to animal, safe to use, shows good antibacterial and lives
Property, more than 93% is entirely reached to the bacteriostasis rate of Escherichia coli, staphylococcus aureus etc.；, can applied to cigarette tipping paper
Inhibitory action is played to the contaminated microorganism of cigarette tipping paper.Cigarette tipping paper is directly being rolled up with oral contact, the compound
Use in cigarette tipping paper can avoid cigarette suck, microbial contamination in transmittance process, effectively increase defending for cigarette
Raw and security.
Raw tobacco material used in the present invention is not limited by area and kind, the present invention can be realized, below with from cloud
The raw tobacco material of cigarette industry Co., Ltd different sources in south, the present invention will be further described.Unless otherwise indicated, originally
Percentage employed in invention is mass percent.
Embodiment 1
Prepare 2- arylbenzofuran class compounds C15H20O2, including medicinal extract extraction, silica gel column chromatography, shooting flow body colour
Spectrum separation, specifically using following steps：
(1) medicinal extract extracts：Using tobacco leaf as raw material, crushed with the first solvent soaking and extract the tobacco 3~5
It is secondary, each 24h~72h, extract solution is merged, filtered and the tobacco extract medicinal extract is obtained after concentrating；Wherein described first
Solvent is the mixture selected from methanol, the organic solvent of ethanol or acetone and water, and wherein organic solvent accounts for first solvent
60wt%~100wt%, and the first solvent：The weight ratio of tobacco is 2~4:1；
(2) silica gel column chromatography：Above-mentioned tobacco extract medicinal extract is molten with second selected from pure methanol, straight alcohol or pure acetone
60~120 mesh silica gel mixed samples after agent dissolving with 1~1.6 times of weight for tobacco extract medicinal extract, the mixture after sample will be mixed
Dry column-packing after being mixed again with 160~300 mesh silica gel of 2~4 times of weight for tobacco extract medicinal extract, then with volume ratio according to
Secondary is 10:0、9:1、8:2、7:3、6:4 and 5:A series of 5 chloroform-acetone solutions carry out gradient elution, and volume is wherein used in collection
Than for 8:The eluent obtained during 2 chloroform-acetone solution elution, referred to as the first eluent；
(3) supercritical fluid chromatography separates：Above-mentioned first eluent is passed through into supercritical fluid chromatography to be separated, this is super
Critical fluids chromatogram uses 10mm × 150mm, 5 μm of Silica 2-EP chromatographic columns, mobile phase carbon dioxide/ethanol (90/
10%, mass ratio), flow rate of mobile phase 20mL/min, UV-detector Detection wavelength is 312nm, and the first eluent liquid is each
The μ L of sample introduction 200~500, collect eluent corresponding when chromatographic peak retention time after each sample introduction is 10.4min, and referred to as second
Eluent, the 2- arylbenzofurans class compound will be produced after the second eluent desolvation.
(4) the 2- arylbenzofurans class compound that supercritical fluid chromatography separation obtains afterwards is again dissolved in first
Alcoholic solution, and using methanol solution as mobile phase, chromatography is carried out by gel column, mentions the 2- aryl further purified
Benzofuran compounds.
Embodiment 2
Tobacco sample derives from Yunnan Yuxi, and kind is Yuxi K326.Tobacco sampling 2.0kg is crushed with 95% methanol
Extraction 5 times, 24h is extracted every time, extract solution merges, and filtering, is concentrated under reduced pressure into medicinal extract, obtains medicinal extract 105g.Medicinal extract is with weight than 2.0
The 120g thick silica gel mixed sample of 100 mesh is used after the pure methanol dissolving of amount again, 0.6kg 160 mesh silica gel fill post progress silica gel column chromatography,
It is 1 with volume proportion:0、20:1、9:1、8:2、7:3、6:4、1:1、1:2 chloroform-acetone gradient elution, TLC monitorings merge phase
Same part, 8 parts are obtained, wherein volume proportion is 8:2 chloroform-acetone elution fraction is carried out with supercritical fluid chromatography
Isolate and purify, the supercritical fluid chromatography uses 10mm × 150mm, 5 μm of Silica 2-EP chromatographic columns, mobile phase titanium dioxide
Carbon/ethanol (90/10%, mass ratio), flow rate of mobile phase 20mL/min, UV-detector Detection wavelength are 312nm, are entered every time
The μ L of sample 500, eluent corresponding when chromatographic peak retention time after each sample introduction is 10.4min is collected, eluent is removed molten
The 2- arylbenzofurans class compound is produced after agent.Products therefrom is dissolved with pure methanol again, then using pure methanol as flowing
Phase, separated with Sephadex LH-20 gel filtration chromatographies, produce the noval chemical compound.
Embodiment 3
Tobacco sample derives from Dali, and kind is cloud and mist 200, tobacco sampling 3.5kg is shredded, with 95% ethanol
Extraction 4 times, 48h is extracted every time, extract solution merges, and filtering, is concentrated under reduced pressure into medicinal extract, obtains medicinal extract 250g.Medicinal extract is with weight than 2.0
The 250g thick silica gel mixed sample of 80 mesh is used after the pure methanol dissolving of amount again, 1.2kg 200 mesh silica gel fill post progress silica gel column chromatography,
It is 1 with volume proportion:0、20:1、9:1、8:2、7:3、6:4、1:1、1:2 chloroform-acetone gradient elution, TLC monitorings merge phase
Same part, 8 parts are obtained, wherein volume proportion is 8:2 chloroform-acetone elution fraction is carried out with supercritical fluid chromatography
Isolate and purify, the supercritical fluid chromatography uses 10mm × 150mm, 5 μm of Silica 2-EP chromatographic columns, mobile phase titanium dioxide
Carbon/ethanol (90/10%, mass ratio), flow rate of mobile phase 20mL/min, UV-detector Detection wavelength are 312nm, are entered every time
The μ L of sample 500, eluent corresponding when chromatographic peak retention time after each sample introduction is 10.4min is collected, eluent is removed molten
The 2- arylbenzofurans class compound is produced after agent.Products therefrom is dissolved with pure methanol again, then using pure methanol as flowing
Phase, separated with Sephadex LH-20 gel filtration chromatographies, produce the noval chemical compound.
Embodiment 4
Tobacco sample derives from Kunming, Yunnan, and kind is the big gold dollar of safflower, tobacco sampling 5kg is crushed, with the third of 75%
Ketone ultrasonic extraction 3 times, 72h is extracted every time, extract solution merges, and filtering, is concentrated under reduced pressure into medicinal extract, obtains medicinal extract 380g.Medicinal extract is used
Weight uses the 400g thick silica gel mixed sample of 90 mesh after the pure methanol dissolving than 1.6 times of amounts, 2.4kg 180 mesh silica gel dress post carries out silicon
Plastic column chromatography, it is 1 with volume proportion:0、20:1、9:1、8:2、7:3、6:4、1:1、1:2 chloroform-acetone gradient elution, TLC
Monitoring merges identical part, obtains 8 parts, and wherein volume proportion is 8:2 chloroform-acetone elution fraction shooting flow
Body colour spectrum is isolated and purified, and the supercritical fluid chromatography uses 10mm × 150mm, 5 μm of Silica 2-EP chromatographic columns, stream
Dynamic phase carbon dioxide/ethanol (90/10%, mass ratio), flow rate of mobile phase 20mL/min, UV-detector Detection wavelength are
312nm, each μ L of sample introduction 500, eluent corresponding when chromatographic peak retention time after each sample introduction is 10.4min is collected, will
The 2- arylbenzofurans class compound is produced after eluent desolvation.Products therefrom is dissolved with pure methanol again, then with
Pure methanol is mobile phase, is separated with Sephadex LH-20 gel filtration chromatographies, produces the noval chemical compound.
Embodiment 5
Compound prepared by Example 1, the knot for the 2- arylbenzofuran class compounds that method described above is prepared
Structure is measured by the following method.The compounds of this invention is light yellow gum thing；Ultraviolet spectra (MeOH), λmax(logε)210
(4.05), 270 (3.08), 312 (3.38) nm, infrared spectrum (KBr tablettings) λmax 3028、2984、1618、1476、1428、
1380、1158、1061、895、784cm-1, ESIMS (cation collection) m/z 305 [M+Na]+；HRESIMS (cation collection)
m/z 305.1162[M+Na]+Calculated value 305.1154, C18H18NaO3).With reference to1H and13C H NMR spectroscopies determine that molecular formula is
C18H18O3, degree of unsaturation 10.Ultraviolet spectra has absorption maximum to confirm aromatic ring knot be present in compound in 210,270,312nm
Structure.Compound1H、13C NMR and DEPT data (table -1) show in compound 18 carbon and 18 hydrogen be present, comprising 11,
2,3,5- quaternary phenyl ring (C-1~C-6, H-4 and H-6), phenyl ring (C-1'~C-6', the H of 1 Isosorbide-5-Nitrae-substituted2- 2', 6',
And H2- 3', 5'), two methyl (C-7 and C-9', H3- 7 and H3- 9'), one group of double bond (C-7 and C-8), and 2 methoxyl group (δC
56.1 and 55.9q, δH3.85 and 3.81s).According to nuclear magnetic resonance data in compound (two phenyl ring, C-7 '~C-9 ', and H3-
9 ') with known compound methoxy-4 '-hydroxy)-aryl-3-methy-6-hydroxybenzofuran is similar, can be first
Step speculates that compound (1) may be 3- methyl -2- arylbenzofurans.In addition, compound (1) is 3- methyl -2- aryl benzos
Furans can further pass through H3- 9 ' and C-1, C-7 ' and C-8 ', H2- 2 ', 6 ' and C-7 ', and H-6 are related to C-8 ' HMBC
(figure -2) is confirmed.After the skeleton of compound is confirmed, remaining substituted radical, methyl (C-7), which is substituted in C-5 positions, to be led to
Cross H3- 7 and C-4, C-5 and C-6, H-4 and C-7, and H-6 is related to C-7 HMBC determines；Two methoxy substitutions are in C-3
It can lead to two methoxyl group hydrogen (δ with C-4 ' positionsH3.81) and C-3 (δ 3.85 andCAnd C-4 ' (δ 151.7)C160.6) HMBC phases
Close and confirm.
Embodiment 6
Compound prepared by Example 3, is yellow jelly.Assay method is same as Example 5, confirms embodiment 3
The compound of preparation is described 2- arylbenzofuran class compounds --- 7- methoxyl groups -2- (4- methoxyphenyls) -3,5-
Dimethyl benzofuran.
Embodiment 7
Compound prepared by Example 4, is yellow jelly.Assay method is same as Example 5, confirms embodiment 4
The compound of preparation is described 7- methoxyl groups -2- (4- methoxyphenyls) -3,5- dimethyl benzofurans.
Embodiment 8
Prepared by Example 1-4 appoints 2- arylbenzofuran classes compound to carry out antibacterial activity experiment, and test situation is such as
Under：
Antimicrobial test is carried out with agar diffusion method, and tested bacterium is equably coated in into plain agar culture medium (ox first
Meat extract, peptone, sodium chloride, serum, agar) flat board on, then by testing compound (benzofuran C prime compound 10mL
DMSO dissolves, and is diluted with water into 50 μ g/mL solution) soaked tablet (diameter 5mm) is placed on the culture medium to carry disease germs, is put into
In insulating box, inhibition zone size is observed after being incubated 24-72h in 25 DEG C.As a result show：The compounds of this invention is to Staphylococcus aureus
Bacterium, Escherichia coli, angstrom uncommon bacterium, hay bacillus, proteus etc. have very strong activity；Inhibiting rate is more than 93%.
Embodiment 9
Safety evaluatio has been carried out to the compounds of this invention, tested by Micronuclei In The Mouse Bone Marrow, Ames is tested and TK genes
Mutating experiment, it was demonstrated that the compounds of this invention is nontoxic to animal, safe to use.This compound is added to cigarette with 50 μ g/mL concentration
On tipping paper；By the People's Republic of China (PRC)《Disposable Sanitary Accessory sanitary standard》GB15979-2002 detection method,
Take the volume cigarette tipping paper for adding the compounds of this invention, 2.0 × 3.0mm sizes, detection bacterium sum, coliform, golden yellow
Staphylococcus, Pseudomonas aeruginosa, hemolytic streptococcus, total number of fungi.As a result show, added the tipping paper bacterium of the compounds of this invention
Fall sum to significantly reduce, this compound has obvious inhibiting effect to the bacterium of several tests, to Escherichia coli, golden yellow grape
The bacteriostasis rate of coccus etc. entirely reaches more than 93%.
Claims (2)
1. a kind of preparation method of 2- arylbenzofurans class compound, the 2- arylbenzofurans class compound have following
Structure：
The compound is named as 7- methoxyl groups -2- (4- methoxyphenyls) -3,5- dimethyl benzofurans, and its molecular formula is
C18H18O3；It is characterized in that this method comprises the following steps：
(1) medicinal extract extracts：Using tobacco leaf as raw material, crushed with the first solvent soaking and extract the tobacco 3~5 times,
Each 24h~72h, extract solution is merged, filtered and the tobacco extract medicinal extract is obtained after concentrating；Wherein described first solvent
It is the mixture selected from methanol, the organic solvent of ethanol or acetone and water, wherein organic solvent accounts for the 60wt% of first solvent
~95wt%, and the first solvent：The weight ratio of tobacco is 2~4:1；
(2) silica gel column chromatography：The tobacco extract medicinal extract that step (1) is obtained is used selected from pure methanol, straight alcohol or pure acetone
Silica gel mixed sample after the dissolving of second solvent with 60~120 mesh of 1~1.6 times of weight for tobacco extract medicinal extract, after sample is mixed
Mixture mixed again with 160~300 mesh silica gel of 2~4 times of weight for tobacco extract medicinal extract after dry column-packing, Ran Houyong
Volume ratio is followed successively by 10:0、9:1、8:2、7:3、6:4 and 5:A series of 5 chloroform-acetone solutions carry out gradient elution, collect it
It is middle to use volume ratio as 8:The eluent obtained during 2 chloroform-acetone solution elution, referred to as the first eluent；
(3) supercritical fluid chromatography separates：The first eluent that step (2) obtains is passed through into supercritical fluid chromatography to be divided
From the supercritical fluid chromatography uses 10mm × 150mm, 5 μm of Silica 2-EP chromatographic columns, and mobile phase is carbon dioxide/second
Alcohol, mass ratio 90/10, flow rate of mobile phase 20mL/min, UV-detector Detection wavelength are 312nm, and the first eluent is every
The secondary μ L of sample introduction 200~500, collect eluent corresponding when chromatographic peak retention time after each sample introduction is 10.4min, and referred to as
Two eluents, described 2- arylbenzofuran class compounds will be produced after the second eluent desolvation.
2. the preparation method of 2- arylbenzofurans class compound according to claim 1, it is also included further below
The step of purification：By the 2- arylbenzofurans class compound obtained afterwards in supercritical fluid chromatography separation again
Methanol solution is dissolved in, and using methanol solution as mobile phase, chromatography is carried out by gel column, what is further purified is described
2- arylbenzofuran class compounds.
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| 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 |
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| 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 |
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