CN106916131A - The preparation method and its pharynx-clearing throat-benefiting effect of the isobenzofuran class compound in a kind of root of kudzu vine - Google Patents
The preparation method and its pharynx-clearing throat-benefiting effect of the isobenzofuran class compound in a kind of root of kudzu vine Download PDFInfo
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- CN106916131A CN106916131A CN201710078271.2A CN201710078271A CN106916131A CN 106916131 A CN106916131 A CN 106916131A CN 201710078271 A CN201710078271 A CN 201710078271A CN 106916131 A CN106916131 A CN 106916131A
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- isobenzofuran
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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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- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
- A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
- A24D3/06—Use of materials for tobacco smoke filters
- A24D3/14—Use of materials for tobacco smoke filters of organic materials as additive
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
- A61K36/488—Pueraria (kudzu)
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- Materials Engineering (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention discloses a kind of isobenzofuran class compound and its preparation method and application, the isobenzofuran class compound is isolated from the traditional Chinese medicine root of kudzu vine, is named as：6 hydroxyl 5 (alkene of 3 methyl, 2 oxo fourth 3) isobenzofurans 1 (3H) ketone, it is English entitled：6‑hydroxy‑5‑(3‑methyl‑2‑oxobut‑3‑enyl)‑isobenzofuran‑1(3H) one, its molecular formula is C13H12O4.With following structural formula：（Ⅰ）The preparation method of the isobenzofuran class compound, is, with the traditional Chinese medicine root of kudzu vine as raw material, to be obtained through medicinal extract extraction, organic solvent extraction, MCI decolourings, silica gel column chromatography, high pressure liquid chromatography separating step.The compounds of this invention is added in cigarette filter, can reduce cigarette smoking throat excitant, with obvious pharynx-clearing throat-benefiting effect.
Description
Technical field
The invention belongs to technical field of phytochemistry, and in particular to extract obtain different in a kind of root of kudzu vine from Chinese medicine first
Benzofuran compounds.Meanwhile, the compounds of this invention is added in cigarette filter, can reduce the stimulation of cigarette smoking throat
Property, with obvious pharynx-clearing throat-benefiting effect.
Background technology
The root of kudzu vine is the dry root of legume pueraria lobata, practises and claims elegant jessamine.Autumn, the excavation of season in winter two, take advantage of fresh-cut into sheet or fritter；
Dry.It is sweet, pungent, it is cool.There is expelling pathogenic factors from muscles and skin to bring down a fever, promoting eruption promotes the production of body fluid to quench thirst, the work(of Shengyang Zhixie.It is usually used in table card to generate heat, stiff nape and back,
Measles without adequate eruption, pyreticosis is thirsty, and the deficiency of Yin is quenched one's thirst, and heat is purged heat dysentery, splenasthenic diarrhea.The root of kudzu vine is also a kind of important health food simultaneously,
Containing the sweet sense in oral cavity, action and efficacy of promoting the production of body fluid composition can be increased, the good reputation of " asia ginseng " is have, kudzuvine root starch is referred to as " long-lived powder ",
It is described as " royal specially offered food " in Japan.
Main chemical compositions in the root of kudzu vine are flavonoids, and main active is Dai, daidzin, Puerarin, the root of kudzu vine
Element -7- xylosides etc., also contain the compound of the other structures type such as terpene, lactone, sterol.During lactone refers to same molecule
Carboxyl interacts with hydroxyl and is dehydrated and the ester type compound of formation, such compound generally existing in natural plants, in day
Also there is the document report for being widely present such compound in right plant, except with extensive pharmacological action, lactone or a class weight
The volatile compound wanted, is naturally occurring in various fruit and spice berry, such compound be widely used in various beverages,
In the formula of the flavoring essences such as bakery product.
A kind of present invention isolated benzo lactone compound from the root of kudzu vine, the compound is added to cigarette filter
In, cigarette smoking throat excitant can be reduced, with obvious pharynx-clearing throat-benefiting effect, the suction comfortableness of cigarette can be improved.
The content of the invention
The first object of the present invention is to provide a kind of isobenzofuran class compound；Second purpose is to provide described different
The preparation method of benzofuran compounds；3rd purpose is to provide the isobenzofuran class compound as cigarette filter
The application of additive is used.
The first object of the present invention is achieved in that described isobenzofuran class compound is from traditional Chinese medicine Pueraria lobota
Isolated in root, its molecular formula is C13H12O4, with following structures：
The compound is light yellow gum thing, is named as：6- hydroxyls -5- (3- methyl -2- oxygen
For butyl- 3- alkene)-isobenzofuran -1 (3H) -one, it is English entitled：6-hydroxy-5-(3-methyl-2-oxobut-3-
enyl)isobenzofuran- 1(3H )-one。
The second object of the present invention is achieved in that the preparation method of the isobenzofuran class compound, is with Pueraria lobota
Root block is raw material, is walked through medicinal extract extraction, organic solvent extraction, MCI decolourings, silica gel column chromatography, high performance liquid chromatography preparative separation
Suddenly, specially：
A, medicinal extract are extracted：The root block of the root of kudzu vine is crushed to 20 ~ 40 mesh, with organic solvent ultrasonic extraction 2 ~ 5 times, every time 30 ~ 60 points
Clock, merges extract solution, filtering, and be concentrated under reduced pressure extract solution, stands, and filters sediment, is condensed into medicinal extract a；
B, organic solvent extraction：Weight is added in medicinal extract a than 1 ~ 2 times of water of amount, then with the organic solvent isometric with water
Extraction 3 ~ 5 times, merges organic solvent extraction phase, is concentrated under reduced pressure into medicinal extract b；
C, MCI decolourize：Add weight than 3 ~ 5 times of methyl alcohol water dissolves of amount in medicinal extract b, upper MCI posts are washed with 90%-95% methyl alcohol
It is de-, merge organic phase, it is concentrated under reduced pressure into medicinal extract c;
D, silica gel column chromatography：Silica gel column chromatography on medicinal extract c, dress post silica gel is 160 ~ 200 mesh, and consumption is 6 ~ 10 times of medicinal extract c weight
Amount；It is 1 with volume proportion:0~0:1 chloroform and acetone mixed organic solvents gradient elution, collects gradient eluent, concentration, warp
TLC is monitored, and merges identical part；
E, high performance liquid chromatography separation：Will be with volume content by 7:The eluent that 3 chloroform-acetone is afforded is through efficient liquid phase
Chromatographic separation and purification, obtains final product described isobenzofuran class compound.
The structure of the isobenzofuran class compound that method described above is prepared is to identify to come by the following method：
The compounds of this invention is light yellow gum thing；HRESI-MS shows that its quasi-molecular ion peak is 255.0630 [M+Na]+
(calculated value 255.0633), with reference to1H NMR and DEPT spectrum determine that its molecular formula is C13H12O4, degree of unsaturation is 8.It is infrared
Hydroxyl (3465 cm are shown in spectrum-1), carbonyl (1749 and 1660 cm-1) and aromatic ring (1612,1546 and 1469 cm-1) resonance absorbing peak.And ultraviolet spectra may be deposited in 210,272,308 nm have absorption maximum to also illustrate that compound
In aromatic ring structure.Compound1H and13C H NMR spectroscopies（Table -1）Show that it contains 13 carbon and 12 hydrogen, including 11,2,4,5-
Quaternary phenyl ring (C-4 ~ C-7, C-4a and C-7a, H-4 and H-7), a 3- methyl -2- oxo butyl- 3- alkene structure fragment
(C-1' ~ C-5', H2-1'、H2- 4' and H3- 5), ester carbonyl group (δ C168.8 s), one oxidation methylene (δ C
74.1 t,δ H5.17 s), and phenolic hydroxyl group (δ H10.52 s).Its HMBC coherent signal is further analyzed, according to
H2- 3 and C-1, C-4, C-4a, C-7a, H-7 and C-1, C-4a, C-7a, and H-4 and C-3, C-4a, C-7a HMBC phases
Closing (Fig. 3) can speculate that compound is benzofuran lactone structure.H-1' and C-4, C- can be observed in the HMBC spectrums of compound
5、C-6；And H-4 is long-range related to C-1', can speculate that 3- methyl -2- oxo butyl- 3- alkene structure fragments are substituted in compound
C-5.According to phenolic hydroxyl group signal (δ H10.52 s) have HMBC related to C-5, C-6 and C-7, can speculate that phenolic hydroxyl group is substituted in
C-6.So far, the structure of compound is determined, and is named as 6- hydroxyls -5- (3- methyl -2- oxo butyl- 3- alkene)-different benzene
And furans -1 (3H) -one.
Infrared, the ultraviolet and mass spectrometric data of compound：UV (methyl alcohol),λ max (log ε ) 308 (3.09)、272
(3.69)、210 (4.01) nm；IR (pressing potassium bromide troche)：ν max 3465、3021、2946、1749、1660、1612、1546、
1469、1370、1274、1153、1067、908、859 cm-1；1H and13C NMR data (500 and 125 MHz,
(CDCl3), it is shown in Table -1；Positive ion mode ESIMS m/z 255 [M+Na]+；Positive ion mode HRESIMS m/z 255.0630
[M+Na]+(calculated value C13H12NaO4, 255.0633).
The compounds of this invention of table -1.1H NMR and13C NMR data (CDCl3)
The third object of the present invention is achieved in that described isobenzofuran class compound as cigarette filter-tip additive agent
Using.It is that cigarette filter is molded the most frequently used plasticizer in view of triacetyl glycerine, and the compounds of this invention is dissolved in three vinegar
Acid glyceride, in cigarette filter forming process, the compounds of this invention is added in filter tip by triacetyl glycerine.
Isobenzofuran class compound of the present invention is separated first, by nuclear magnetic resonance and measuring method of mass spectrum
It is defined as isobenzofuran class compound, and characterizes its structure.The compounds of this invention is added to volume by triacetyl glycerine
In tobacco filters, to be not added with the identical cigarette of the compound as control, sensory evaluation is carried out.Evaluation and analysis result shows：With it is right
Photograph is compared, and addition the compounds of this invention can reduce cigarette smoking throat excitant, with obvious pharynx-clearing throat-benefiting effect.The present invention
Compound is added in cigarette filter, is easily realized in technique, and the additional step in production process is not increased, can be obviously improved volume
Cigarette suction quality, there is good application prospect.
Brief description of the drawings
Fig. 1 is the carbon-13 nmr spectra of isobenzofuran class compound of the present invention（13C NMR）；
Fig. 2 is the proton nmr spectra of isobenzofuran class compound of the present invention（1H NMR）；
Fig. 3 is the related figures of crucial HMBC of isobenzofuran class compound of the present invention.
Specific embodiment
The present invention is further illustrated below in conjunction with the accompanying drawings, but the present invention is any limitation as never in any form, base
In present invention teach that any conversion or improvement made, each fall within protection scope of the present invention.
Unless otherwise indicated, percentage of the present invention is mass percent.
Isobenzofuran class compound of the present invention, is isolated from the traditional Chinese medicine root of kudzu vine, its molecular formula
It is C13H12O4, with following structures：
The compound is light yellow gum thing, is named as：6- hydroxyls -5- (3- methyl -2- oxo butyl- 3- alkene) isobenzofuran -
1(3H) -one, it is English entitled：6-hydroxy-5-(3-methyl-2-oxobut-3-enyl)isobenzofuran- 1(3H
)-one。
The preparation method of isobenzofuran class compound of the present invention, be the root block with the root of kudzu vine as raw material, carried through medicinal extract
Take, organic solvent extraction, MCI decolourings, silica gel column chromatography, high performance liquid chromatography preparative separation step, specially：
A, medicinal extract are extracted：The root block of the root of kudzu vine is broken to 20 ~ 40 mesh, with organic solvent ultrasonic extraction 2 ~ 5 times, 30 ~ 60 minutes every time,
Merge extract solution, filtering, be concentrated under reduced pressure extract solution, stands, and filters sediment, is condensed into medicinal extract a；
B, organic solvent extraction：Weight is added in medicinal extract a than 1 ~ 2 times of water of amount, then with the organic solvent isometric with water
Extraction 3 ~ 5 times, merges organic solvent extraction phase, is concentrated under reduced pressure into medicinal extract b；
C, MCI decolourize：Add weight than 3 ~ 5 times of methyl alcohol water dissolves of amount in medicinal extract b, upper MCI posts are washed with 80%-90% methyl alcohol
It is de-, merge organic phase, it is concentrated under reduced pressure into medicinal extract c；
D, silica gel column chromatography：Silica gel column chromatography on medicinal extract c, dress post silica gel is 160 ~ 200 mesh, and consumption is 6 ~ 10 times of medicinal extract c weight
Amount；It is 1 with volume proportion:0~0:1 chloroform and acetone mixed organic solvents gradient elution, collects gradient eluent, concentration, warp
TLC is monitored, and merges identical part；
E, high performance liquid chromatography separation：Will with volume content be by（7:3）The eluent that affords of chloroform-acetone through efficient
Liquid chromatogram is isolated and purified, and obtains final product described isobenzofuran class compound.
The organic solvent of the step A is 70 ~ 100% acetone, 90 ~ 100% ethanol or 90 ~ 100% methyl alcohol.
The organic solvent of the step B is dichloromethane, chloroform, ethyl acetate ether or petroleum ether.
Medicinal extract c is dissolved with weight before through silica gel column chromatography than the acetone or methyl alcohol of 1.5 ~ 3 times of amounts in the D steps,
Then 0.8 ~ 1.2 times of 80 ~ 100 mesh silica gel mixed samples are weighed with medicinal extract.
The chloroform of the D steps and the volume proportion of acetone mixed organic solvents are 20:1, 9:1, 8:2, 7:3, 6:4
With 1:1.
The E steps high performance liquid chromatography separation purifying be the methyl alcohol with 35-46% as mobile phase, the ml/ of flow velocity 15 ~ 25
Min, with 21.2 × 250 mm, 5 μm of Zorbax PrepHT GF reverse phase preparative columns are fixing phase, UV-detector detection ripple
A length of 308 nm, the μ L of each sample introduction 10 ~ 100, collect the chromatographic peak of 20 ~ 40 min, are evaporated after repeatedly adding up.
The compounds of this invention is added in cigarette filter, with preferable flavouring effect；And compared with control, add
Plus the compounds of this invention can reduce cigarette smoking throat excitant, with obvious pharynx-clearing throat-benefiting effect.
The root of kudzu vine of the present invention is not limited by area and kind, can realize the present invention.
Embodiment 1
The dry kg of root of kudzu vine block 4.4 is taken, meal is broken to 30 mesh, with 70% acetone ultrasonic extraction 4 times, 60 minutes every time, extracted
Liquid merges；Extract solution is filtered, and is concentrated under reduced pressure into the 1/4 of volume；Stand, filter sediment, be condensed into the medicinal extract a of 120g；In leaching
250g water is added in cream a, is extracted 5 times with the chloroform isometric with water, merge extraction phase, be concentrated under reduced pressure into 80g medicinal extract b；Medicinal extract b
Post is filled with MCI, the 80% methyl alcohol water dissolves of 240 g is added in medicinal extract b, then upper prop, with 90% methanol-water, 2 to 6 liters of wash-outs, received
Collection eluent, is concentrated under reduced pressure to give 62 g medicinal extract c；Medicinal extract c adds the acetone solution of 120g in medicinal extract c, is subsequently adding 100 mesh
The g of silica gel 62 mixes sample, after mixing sample, post is filled with the g of 200 mesh silica gel 400；20 are respectively with volume ratio:1, 9:1, 8:2, 7:3,
6:4 and 1:1 chloroform-acetone mixed organic solvents gradient elution, collects gradient eluent, concentration, is monitored through TLC, merges phase
Same part, obtains 6 part A-F, wherein, to the sample D (7 being collected into:3) g of part 14, then be to flow with 40% methyl alcohol
Dynamic phase, flow velocity 20 ml/min, 21.2 × 250 mm, 5 μm of Zorbax PrepHT GF reverse phase preparative columns are fixing phase,
UV-detector Detection wavelength is 308 nm, the μ L of each sample introduction 50, collects the chromatographic peak of 33.9 min, is evaporated after repeatedly adding up,
Obtain final product the isobenzofuran class compound.
Embodiment 2
The dry kg of root of kudzu vine block 10 is taken, meal is broken to 40 mesh, extracted 4 times with 80% methyl alcohol cold soaking, 3 days every time, extract solution was closed
And；Extract solution is filtered, and is concentrated under reduced pressure into the 1/4 of volume；Stand, filter sediment, be condensed into 300 g medicinal extract a；In medicinal extract a
350 g water are added, is extracted 5 times with the ethyl acetate isometric with water, merge extraction phase, be concentrated under reduced pressure into 210 g medicinal extract b；Leaching
Cream b fills post with MCI, and the 80% methyl alcohol water dissolves of 600 g are added in medicinal extract b, and then upper prop, is washed for 5 to 15 liters with 90% methanol-water
It is de-, eluent is collected, it is concentrated under reduced pressure to give 150 g medicinal extract c；The acetone solution of 300 g is added in medicinal extract c, 100 mesh are subsequently adding
The g of silica gel 150 mixes sample, and post is filled with the Kg of 200 mesh silica gel 1, mixes upper prop after sample；20 are respectively with volume ratio:1, 9:1, 8:2, 7:
3, 6:4 and 1:1 chloroform-acetone mixed organic solvents gradient elution, collects gradient eluent, concentration, is monitored through TLC, closes
And identical part, 6 part A-F are obtained, wherein, to the sample D (7 being collected into:3) g of part 25, then with 40% methyl alcohol
It is mobile phase, flow velocity 20 ml/min, 21.2 × 250 mm, 5 μm of Zorbax PrepHT GF reverse phase preparative columns are fixing phase,
UV-detector Detection wavelength is 308 nm, the μ L of each sample introduction 80, collects the chromatographic peak of 33.9 min, is evaporated after repeatedly adding up,
Obtain final product the noval chemical compound.
Embodiment 3
Compound prepared by Example 1, is light yellow gum thing；
Assay method is：With nuclear magnetic resonance, structure is identified with reference to other spectroscopic techniques.
HRESI-MS shows that its quasi-molecular ion peak is 255.0630 [M+Na]+(calculated value 255.0633), with reference to1H
NMR and DEPT spectrums determine that its molecular formula is C13H12O4, degree of unsaturation is 8.Hydroxyl (3465 cm are shown in infrared spectrum-1), carbonyl (1749 and 1660 cm-1) and aromatic ring (1612,1546 and 1469 cm-1) resonance absorbing peak.And ultraviolet light
Spectrum there may be aromatic ring structure in 210,272,308 nm have absorption maximum to also illustrate that compound.Compound1H and13C
H NMR spectroscopy（Table -1）Show that it contains 13 carbon and 12 hydrogen, including 11,2,4,5- quaternary phenyl ring (C-4 ~ C-7, C-4a
And C-7a, H-4 and H-7), 3- methyl -2- oxo butyl- 3- alkene structure fragments (C-1' ~ C-5', a H2-1'、H2- 4' and H3-
5), ester carbonyl group (δ C168.8 s), one oxidation methylene (δ C74.1 t,δ H5.17 s), and a phenol
Hydroxyl (δ H10.52 s).Its HMBC coherent signal is further analyzed, according to H2- 3 and C-1, C-4, C-4a, C-7a, H-7
Can speculate that compound is benzofuran with C-1, C-4a, C-7a, and H-4 (Fig. 3) related to the HMBC of C-3, C-4a, C-7a
Lactone structure.H-1' and C-4, C-5, C-6 can be observed in the HMBC spectrums of compound；And H-4 is long-range related to C-1',
Can speculate that 3- methyl -2- oxo butyl- 3- alkene structure fragments are substituted in C-5 of compound.According to phenolic hydroxyl group signal (δ H 10.52
S) there is HMBC related to C-5, C-6 and C-7, can speculate that phenolic hydroxyl group is substituted in C-6.So far, the structure of compound determined,
And it is named as 6- hydroxyls -5- (3- methyl -2- oxo butyl- 3- alkene)-isobenzofuran -1 (3H) -one.
Embodiment 4
Compound prepared by Example 2, is light yellow gum thing.Assay method is same as Example 3, confirms that implementing 2 prepares
Compound be the isobenzofuran class compound --- 6- hydroxyls -5- (3- methyl -2- oxo butyl- 3- alkene)-different benzo furan
Mutter -1 (3H) -one.
Embodiment 5
The isobenzofuran compound of any preparation in Example 1-2 carries out the additive effect experiment of cigarette filter, tests feelings
Condition is as follows：
For the cigarette " purple cloud " that addition cigarette is Hong Yun Red River group, with triacetyl glycerine by above-mentioned isobenzofuran chemical combination
The thing solution for being made into 0.1 mg/mL.Uniformly it is sprayed onto on filter tow by the 8% of filter tow weight, is made filter stick, so
The filter stick is made cigarette by conventional cigarette cigarette afterwards, sensory evaluation is carried out, and to be not added with the same volume of the compound
Cigarette is used as control.Evaluation and analysis result shows：Compared with control, addition the compounds of this invention can reduce the stimulation of cigarette smoking throat
Property, with obvious pharynx-clearing throat-benefiting effect.
Embodiment 6
The isobenzofuran compound of any preparation in Example 1-4 carries out the additive effect experiment of cigarette filter,
For the cigarette " purple cloud " that addition cigarette is Hong Yun Red River group, with triacetyl glycerine by above-mentioned isobenzofuran chemical combination
The thing solution for being made into 0.2 mg/mL.Uniformly it is sprayed onto on filter tow by the 5% of filter tow weight, is made filter stick, so
The filter stick is made cigarette by conventional cigarette cigarette afterwards, sensory evaluation is carried out, and to be not added with the same volume of the compound
Cigarette is used as control.Evaluation and analysis result shows：Compared with control, addition the compounds of this invention can reduce the stimulation of cigarette smoking throat
Property, with obvious pharynx-clearing throat-benefiting effect.
Claims (8)
1. a kind of isobenzofuran class compound, it is characterised in that the isobenzofuran class compound is from traditional Chinese medicine Pueraria lobota
It is isolated in root, it is named as：6- hydroxyls -5- (3- methyl -2- oxo butyl- 3- alkene)-isobenzofuran -1 (3H) -one, English
It is entitled：6-hydroxy-5-(3-methyl-2-oxobut-3-enyl)-isobenzofuran-1(3H)-one, its molecular formula
It is C13H12O4, with following structures：
。
2. the preparation method of isobenzofuran class compound described in a kind of claim 1, it is characterised in that with root of kudzu vine block as raw material,
Through medicinal extract extraction, organic solvent extraction, MCI decolourings, silica gel column chromatography, high performance liquid chromatography preparative separation step, specially：
A, medicinal extract are extracted：The root of kudzu vine is crushed to 20 ~ 40 mesh, with organic solvent ultrasonic extraction 2 ~ 5 times, 30 ~ 60 minutes every time, is merged
Extract solution, filtering, be concentrated under reduced pressure extract solution, stands, and filters sediment, is condensed into medicinal extract a；
B, organic solvent extraction：Weight is added in medicinal extract a than 1 ~ 2 times of water of amount, then with the organic solvent isometric with water
Extraction 3 ~ 5 times, merges organic solvent extraction phase, is concentrated under reduced pressure into medicinal extract b；
C, MCI decolourize：Add weight than 3 ~ 5 times of methyl alcohol water dissolves of amount in medicinal extract b, upper MCI posts are washed with 90%-95% methyl alcohol
It is de-, merge organic phase, it is concentrated under reduced pressure into medicinal extract c;
D, silica gel column chromatography：Silica gel column chromatography on medicinal extract c, dress post silica gel is 160 ~ 200 mesh, and consumption is 6 ~ 10 times of medicinal extract c weight
Amount；It is 1 with volume proportion:0~0:1 chloroform and acetone mixed organic solvents gradient elution, collects gradient eluent, concentration, warp
TLC is monitored, and merges identical part；
E, high performance liquid chromatography separation：By 7:The eluent that 3 chloroform-acetone is afforded is pure through high performance liquid chromatography separation
Change, obtain final product described isobenzofuran class compound.
3. the preparation method of isobenzofuran class compound according to claim 2, it is characterised in that the step A has
Machine solvent is 70 ~ 100% acetone, 90 ~ 100% ethanol or 90 ~ 100% methyl alcohol.
4. the preparation method of isobenzofuran class compound according to claim 2, it is characterised in that the step B has
Machine solvent is dichloromethane, chloroform, ethyl acetate ether or petroleum ether.
5. the preparation method of isobenzofuran class compound according to claim 2, it is characterised in that soaked in the D steps
Cream c is dissolved with weight before through silica gel column chromatography than the acetone or methyl alcohol of 1.5 ~ 3 times of amounts, then weighs 0.8 ~ 1.2 times with medicinal extract
80 ~ 100 mesh silica gel mixed samples.
6. the preparation method of isobenzofuran class compound according to claim 2, it is characterised in that the D steps
The volume proportion of chloroform and acetone mixed organic solvents is 20:1, 9:1, 8:2, 7:3, 6:4 and 1:1.
7. the preparation method of isobenzofuran class class compound according to claim 2, it is characterised in that the E steps
High performance liquid chromatography separation purifying be the methyl alcohol with 35-46% as mobile phase, the ml/min of flow velocity 15 ~ 25, with 21.2 × 250
Mm, 5 μm of Zorbax PrepHT GF reverse phase preparative columns are fixing phase, and UV-detector Detection wavelength is 308 nm, is entered every time
The μ L of sample 10 ~ 100, collect the chromatographic peak of 20 ~ 40 min, are evaporated after repeatedly adding up.
8. the isobenzofuran class compound described in a kind of claim 1 as cigarette filter-tip additive agent application.
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| 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 |
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