CN107118194B - A kind of isoflavone compound and the preparation method and application thereof that can improve cigarette smoking throat comfort - Google Patents
A kind of isoflavone compound and the preparation method and application thereof that can improve cigarette smoking throat comfort Download PDFInfo
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- CN107118194B CN107118194B CN201710409525.4A CN201710409525A CN107118194B CN 107118194 B CN107118194 B CN 107118194B CN 201710409525 A CN201710409525 A CN 201710409525A CN 107118194 B CN107118194 B CN 107118194B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/34—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only
- C07D311/36—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only not hydrogenated in the hetero ring, e.g. isoflavones
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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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
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Abstract
The present invention relates to a kind of isoflavone compounds and the preparation method and application thereof that can improve cigarette smoking throat comfort, belong to Phytochemistry technology technical field.The compound is isolated from Chinese medicine pueraria lobata, molecular formula C18H14O5, Compound nomenclature are as follows: and 7- acetyl group -4 '-hydroxyl -6- methoxy-isofiavone, English name are as follows: 7-acetyl-4 '-hodraxy-6-methoxy-isoflavone, structural formula are as shown in the formula (I):, formula (I).The preparation method of the isoflavone compound is using traditional Chinese medicine pueraria lobata as raw material, is extracted through medicinal extract, organic solvent extraction, MCI decolourizes, silica gel column chromatography and high performance liquid chromatography separation step are made.The compounds of this invention is added in cigarette filter, can increase cigarette smoking throat comfort, has apparent pharynx-clearing throat-benefiting effect.
Description
Technical field
The invention belongs to technical field of phytochemistry, and in particular to it is a kind of extracted for the first time from Chinese medicine pueraria lobata it is different
Flavone compound, preparation method and application.The compound has the effect of significantly improving cigarette smoking throat comfort, can
As cigarette filter tip additive for improving cigarette smoking quality.
Background technique
Pueraria lobata is the dry root of legume pueraria lobata, practises and claims elegant jessamine.Autumn, the excavation of two season of winter, fresh-cut is taken advantage of into sheet or fritter；
It is 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 function of Shengyang Zhixie.It is usually used in exterior syndrome 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.Pueraria lobata is also a kind of important health food simultaneously,
Its medical value is high, is known as the good reputation of " asia ginseng ", and kudzuvine root starch is referred to as " long-lived powder ", is known as in Japan " royal specially offered
Food ".
Main chemical compositions in pueraria lobata are flavones and isoflavone compound (daidzein, daidzin, Puerarin, pueraria lobata
Element -7- xyloside etc.), the compound also containing the other structures type such as terpene, lactone, sterol.Isoflavones is flavonoid
One of object, it is cyclized and is formed with benzochromone after being extended by cinnamoyl coacetylase side chain in plant phenylalanine metabolic process
Phenolic compound based on ring, 3- phenyl derivatives are isoflavone compound.Isoflavone compound life outstanding
Reason activity causes the extensive concern of scientific worker.Research shows that pueraria isoflavone has supplement female estrogen, shrinks and put down
Sliding flesh increases the effects of being preced with blood flow, inhibiting platelet aggregation, is hypoglycemic；Isoflavones also has anti-oxidant, antitumor, prevention
Artery sclerosis improves other multiple efficacies such as osteoporosis.In addition, there are also the function for improving people's taste effect for isoflavone compound
Can, it is also widely used in the food industry.
The present invention isolated a kind of isoflavone compound, the compound from pueraria lobata are added to cigarette filter
In, it can significantly reduce cigarette smoking throat irritation, there is apparent throat soothing effect.The compounds of this invention is added to cigarette filter
In, it can be obviously improved cigarette smoking quality, not yet find relevant report at present.
Summary of the invention
The first object of the present invention is to provide a kind of isoflavone compound；Second is designed to provide the isoflavones
The preparation method of class compound；Third is designed to provide application of the isoflavone compound in cigarette filter, mainly
For reducing cigarette smoking throat irritation, improve cigarette smoking quality.
To achieve the above object, The technical solution adopted by the invention is as follows:
The first object of the present invention is achieved in that the isoflavone compound is separated from Chinese medicine pueraria lobata
It arrives, molecular formula C18H14O5, Compound nomenclature are as follows: 7- acetyl group -4 '-hydroxyl -6- methoxy-isofiavone, English name are as follows: 7-
Acetyl-4 '-hodraxy-6-met hoxy-isoflavone, shown in structural formula such as formula (I):
The compound is light yellow gum object.
The second object of the present invention is achieved in that the preparation method of the isoflavone compound, is to be with pueraria lobata
Raw material is extracted through medicinal extract, organic solvent extraction, MCI decolourizes, silica gel column chromatography and high performance liquid chromatography separation step are made, tool
Body are as follows:
A, medicinal extract extracts: pueraria lobata being crushed to 20~40 mesh, is extracted 2~5 times with solvent supersonic, every time Extraction solvent used
Quality be 2~4 times of pueraria lobata quality, 30~60 minutes every time, combined extract simultaneously filtered, and filtrate decompression is concentrated into naked eyes and sees
Observing just has Precipitation, stands 3~5h, filters out sediment, gained filtrate is condensed into medicinal extract a later；
B, organic solvent extracts: the water that weight is 1~2 times of medicinal extract a weight being added into medicinal extract a, then uses organic solvent
Extraction 3~5 times, the volume of organic solvent used is identical as water volume every time, merges organic solvent extraction phase, will merge later
Obtained organic solvent extraction phase is concentrated under reduced pressure into medicinal extract b；
C, MCI decolourizes: into medicinal extract b, addition is the pure methanol of 3~5 times of medicinal extract b weight, after medicinal extract b is completely dissolved, on
MCI column is that 90~95% methanol aqueous solutions are eluted with volumetric concentration, merges eluent, later by the eluent after merging
Medicinal extract c is concentrated under reduced pressure into；
D, silica gel column chromatography: by silica gel column chromatography on medicinal extract c, dress column silica gel is 160~200 mesh, the weight of used silica gel
It is measured for 6~10 times of medicinal extract c weight；It is the chloroform and acetone mixed organic solvents gradient elution of 1:0~0:1 with volume ratio, collects
The gradient eluent of each gradient and concentration, monitor through TLC, merge identical part；Each gradient elution to TLC contact plate without point after
(after i.e. the gradient elution does not go out substance), replaces next gradient elution；
E, high performance liquid chromatography separation: volume ratio will be used to afford for the chloroform of 7:3-acetone mixed organic solvents
Part is purified using high performance liquid chromatography separation to get the isoflavone compound.
It is further preferred that the solvent of the step A be volumetric concentration be 70~100% aqueous acetone solution, volume
The methanol aqueous solution that the ethanol water or volumetric concentration that concentration is 90~100% are 90~100%.
It is further preferred that the organic solvent of the step B is methylene chloride, chloroform, ethyl acetate ether or petroleum
Ether.
It is further preferred that in the D step medicinal extract c before through silica gel column chromatography, first with weight be medicinal extract c1.5~
3 times of acetone or methanol dissolution, is then 0.8~1.2 times of medicinal extract c of 80~100 mesh silica gel mixed samples, Zhi Houshang with weight
Sample.
It is further preferred that in the D step, when gradient elution, used chloroform and acetone mixed organic solvents
Volume ratio be followed successively by 20:1,9:1,8:2,7:3,6:4 and 1:1；Each gradient elution is to TLC contact plate without (i.e. gradient after point
After can not eluting substance), replace next gradient elution.
It is further preferred that the high performance liquid chromatography separation purifying of the E step is the first for being 48% with volumetric concentration
Alcohol solution is mobile phase, 15~25ml/min of flow velocity, with 21.2 × 250mm, 5 μm of Zorbax PrepHT GF reverse phase preparation
Column is stationary phase, and UV detector Detection wavelength is 355nm, and each 10~100 μ L of sample introduction collects the chromatographic peak of 38.5min, more
It is secondary it is cumulative after be evaporated.
Those skilled in the art should know that the technical program is an optimal technical scheme, high performance liquid chromatography separation
It is without being limited thereto to purify the mobile phase used.
The structure for the isoflavone compound being in the above way prepared is measured by the following method:
The compounds of this invention is yellow jelly；HRESI-MS shows that its quasi-molecular ion peak is 333.0746 [M+Na]+
(calculated value 333.0739), in conjunction with1H NMR and DEPT, which are composed, determines that its molecular formula is C18H14O5, degree of unsaturation 12.
Hydroxyl (3420cm is shown in infrared spectroscopy-1), carbonyl (1718 and 1650cm-1) and aromatic ring (1612,1527 and
1430cm-1) resonance absorbing peak.And ultraviolet spectra has absorption maximum to also illustrate in compound in 210,258,310 and 355nm
There may be aromatic ring structures.
Compound1H and13C H NMR spectroscopy (such as table 1, Fig. 1 and Fig. 2) shows that it contains 18 carbon and 14 hydrogen, including 1
Isoflavones skeleton (C-1~C-10 and C-1 '~C-6 ', H-5, H-8, H-2 ', 6 ' and H-2 ', 6 '), a methoxyl group (δC
56.2 δH3.81s), an acetyl group (δC198.8s and 29.9q, δH2.48s) and a phenolic hydroxyl group (δH11.04).Change
The isoflavones skeleton for closing object can be further by H-5 and C-4, C-6, C-7, C-9, C-10, H-8 and C-1 ", C-6, C-7, C-9, C-
10, H-2 and C-1 ', C-3, C-4, C-9 and H-2 ', 6 ' related to the HMBC of C-3 are confirmed.
Its HMBC Correlated Spectroscopy (such as Fig. 3) is further analyzed, according to methoxyl group hydrogen (δH3.81) with C-6 (δC154.9)
HMBC correlation can speculate methoxy substitution in the position C-6 of isoflavones parent nucleus.Phenolic hydroxyl group is substituted in the position C-4 ' can be by phenolic hydroxyl group hydrogen (δH
11.04) with C-3 ', 5 ' (δCAnd C-4 ' (δ 116.3)C157.4) HMBC correlation confirmation.Finally, acetyl group is substituted in C-7
It can be by H-2 " (δH2.50) with C-7 (δCAnd H-8 (δ 125.7)H7.50) with C-1 " (δC198.8) HMBC correlation obtains
It determines.Typical proton signal H-5 (δ on phenyl ringH 7.30)、H-8(δH 7.50)、H-2,6[δH7.75 (d, J=8.8)] and
H-3,5[(δH(6.78 d, J=8.8)] also support isoflavones parent nucleus on above-mentioned substituent group mode.
So far, the structure of compound is determined, and is named as Compound nomenclature are as follows: 7- acetyl group -4 '-hydroxyl -6- first
Oxygroup-isoflavones.
Infrared, the ultraviolet and mass spectrometric data of compound: UV (methanol), λmax(logε)355(3.68、310(3.12)、258
(3.90),210(4.28)nm；IR (pressing potassium bromide troche): νmax 3420、3085、2928、1718、1650,1612、1547、
1516、1430、1365、1264、1147、1063、920、853cm-1；1H and13C NMR data (500 and 125MHz, (C5D5N),
It is shown in Table 1；Positive ion mode ESIMS m/z 333 [M+Na]+；Positive ion mode HRESIMS m/z 333.0746 [M+Na]+(meter
Calculation value C18H14O5, 333.0739).
1. the compounds of this invention of table1H NMR and13C NMR data (C5D5N)
| No. | δC | δH | No. | δC | δH |
| 2 | 153. | 7.83 | 1′ | 12 | |
| 3 | 122. | 2′6′ | 12 | 7.75 | |
| 4 | 175. | 3′5′ | 11 | 6.78 | |
| 5 | 115. | 7.30 | 4′ | 15 | |
| 6 | 154. | 1″ | 19 | ||
| 7 | 125. | 2″ | 2 | 2.50s | |
| 8 | 118. | 7.50 | OMe | 5 | 3.81s |
| 9 | 150. | Ar- | 11.04s | ||
| 10 | 130. |
The third object of the present invention is achieved in that
The isoflavone compound that the present invention can improve cigarette smoking throat comfort is comfortable in improvement cigarette smoking throat
Application in property.
Further, the isoflavone compound that the present invention can improve cigarette smoking throat comfort, which is used as, prepares cigarette filter
The application of additive.The additives of filter tip can be used to improve cigarette smoking throat comfort.
The present invention is that cigarette filter forms most common plasticizer, and the compounds of this invention in view of triacetyl glycerine
It is dissolved in triacetyl glycerine, in cigarette filter forming process, the compounds of this invention can be added to by triacetyl glycerine
In filter tip.
Compared with prior art, the present invention has the advantages that:
Isoflavone compound of the present invention is separated for the first time, is determined by nuclear magnetic resonance and measuring method of mass spectrum
For isoflavone compound, and characterize its structure.The compounds of this invention is added to cigarette filter by triacetyl glycerine
In, the identical cigarette to be not added with the compound carries out sensory evaluation as control.Evaluation and analysis the result shows that: compare with control,
Addition the compounds of this invention can reduce cigarette smoking throat irritation, have obvious pharynx-clearing throat-benefiting effect.The compounds of this invention adds
It is added in cigarette filter, it is easy to accomplish in technique, do not increase the additional step in production process, cigarette smoking product can be obviously improved
Matter has good application prospect.
Detailed description of the invention
Fig. 1 be isoflavone compound of the present invention carbon-13 nmr spectra (13C NMR)；
Fig. 2 be isoflavone compound of the present invention nuclear magnetic resonance spectroscopy (1H NMR)；
The crucial HMBC correlation figure of Fig. 3 isoflavone compound of the present invention.
Specific embodiment
Below with reference to embodiment, the present invention is described in further detail.
It will be understood to those of skill in the art that the following example is merely to illustrate the present invention, and it should not be regarded as limiting this hair
Bright range.In the examples where no specific technique or condition is specified, described technology or conditions according to the literature in the art
Or it is carried out according to product description.Reagents or instruments used without specified manufacturer is that can be obtained by purchase
Conventional products.
The whole common commercially available dried products of pueraria lobata of the present invention.
Isoflavone compound of the present invention, be it is isolated from traditional Chinese medicine pueraria lobata, molecular formula is
C18H14O5, have a structure in which
Name are as follows: Compound nomenclature is Compound nomenclature are as follows: 7- acetyl group -4 '-hydroxyl -6- methoxy-isofiavone, English
Name are as follows: 7-acetyl-4 '-hodraxy-6-methoxy-isoflavone.
The preparation method of isoflavone compound of the present invention is extracted through medicinal extract, organic solvent using pueraria lobata as raw material
Extraction, MCI decoloration, silica gel column chromatography and high performance liquid chromatography separation step are made, specifically:
A, medicinal extract extracts: pueraria lobata being crushed to 20~40 mesh, is extracted 2~5 times with solvent supersonic, every time Extraction solvent used
Quality be 2~4 times of pueraria lobata quality, 30~60 minutes every time, combined extract simultaneously filtered, and filtrate decompression is concentrated into naked eyes and sees
Observing just has Precipitation, stands 3~5h, filters out sediment, gained filtrate is condensed into medicinal extract a later；
B, organic solvent extracts: the water that weight is 1~2 times of medicinal extract a weight being added into medicinal extract a, then uses organic solvent
Extraction 3~5 times, the volume of organic solvent used is identical as water volume every time, merges organic solvent extraction phase, will merge later
Obtained organic solvent extraction phase is concentrated under reduced pressure into medicinal extract b；
C, MCI decolourizes: into medicinal extract b, addition is the pure methanol of 3~5 times of medicinal extract b weight, after medicinal extract b is completely dissolved, on
MCI column is that 90~95% methanol aqueous solutions are eluted with volumetric concentration, merges eluent, later by the eluent after merging
Medicinal extract c is concentrated under reduced pressure into；
D, silica gel column chromatography: by silica gel column chromatography on medicinal extract c, dress column silica gel is 160~200 mesh, the weight of used silica gel
It is measured for 6~10 times of medicinal extract c weight；It is the chloroform and acetone mixed organic solvents gradient elution of 1:0~0:1 with volume ratio, collects
The gradient eluent of each gradient and concentration, monitor through TLC, merge identical part；Each gradient elution to TLC contact plate without point after
(after i.e. the gradient elution does not go out substance), replaces next gradient elution；
E, high performance liquid chromatography separation: volume ratio will be used to afford for the chloroform of 7:3-acetone mixed organic solvents
Part is purified using high performance liquid chromatography separation to get the isoflavone compound.
The solvent of the step A be volumetric concentration be 70~100% aqueous acetone solution, volumetric concentration be 90~100%
Ethanol water or volumetric concentration be 90~100% methanol aqueous solution.
The organic solvent of the step B is methylene chloride, chloroform, ethyl acetate ether or petroleum ether.
Medicinal extract c is first the acetone or first of medicinal extract c1.5~3 times with weight before through silica gel column chromatography in the D step
Alcohol dissolution, is then 0.8~1.2 times of medicinal extract c of 80~100 mesh silica gel mixed samples with weight, later loading.
In the D step, when gradient elution, the volume ratio of used chloroform and acetone mixed organic solvents is followed successively by
20:1,9:1,8:2,7:3,6:4 and 1:1；Each gradient elution is to TLC contact plate without (i.e. the gradient elution does not go out substance after point
Afterwards), next gradient elution is replaced.
The high performance liquid chromatography separation purifying of the E step is using the methanol aqueous solution that volumetric concentration is 48% as flowing
Phase, 15~25ml/min of flow velocity, with 21.2 × 250mm, 5 μm of Z orbax PrepHT GF reverse phase preparative column is stationary phase, purple
External detector Detection wavelength is 355nm, and each 10~100 μ L of sample introduction collects the chromatographic peak of 38.5min, is evaporated after repeatedly adding up.
The compounds of this invention is added in cigarette filter, has the cigarette smoking throat comfort effect that improves significantly；
And compare with control, cigarette smoking throat irritation is substantially reduced, and has obvious pharynx-clearing throat-benefiting effect.
Embodiment 1
A, medicinal extract extracts: pueraria lobata being crushed to 20 mesh, is extracted 2 times with solvent supersonic, every time the quality of Extraction solvent used
It is 2 times of pueraria lobata quality, 30 minutes every time, combined extract simultaneously filtered, and filtrate decompression, which is concentrated into be observed visually, just precipitating
It is precipitated, stands 3h, filter out sediment, gained filtrate is condensed into medicinal extract a later；
B, organic solvent extracts: the water that weight is 1 times of medicinal extract a weight being added into medicinal extract a, is then extracted with organic solvent
3 times, the volume of organic solvent used is identical as water volume every time, merges organic solvent extraction phase, later obtains merging
Organic solvent extraction phase is concentrated under reduced pressure into medicinal extract b；
C, MCI decolourizes: into medicinal extract b, addition is the pure methanol of 3 times of medicinal extract b weight, after medicinal extract b is completely dissolved, upper MCI
Column is that 90% methanol aqueous solution is eluted with volumetric concentration, merges eluent, the eluent after merging is concentrated under reduced pressure later
At medicinal extract c；
D, silica gel column chromatography: medicinal extract c is first c1.5 times of medicinal extract of acetone solution with weight, is then medicinal extract c with weight
0.8 times of 80 mesh silica gel mixed samples, loading carries out column chromatography later, wherein dress column silica gel is 160 mesh, and the weight of used silica gel is
6 times of medicinal extract c weight amounts；With volume ratio be followed successively by 20:1,9:1,8:2,7:3,6:4 and 1:1 chloroform and acetone mixing it is organic molten
Agent gradient elution is collected the gradient eluent of each gradient and concentration, is monitored through TLC, and identical part is merged；Each gradient elution
To TLC contact plate without after point (i.e. the gradient elution not go out substance after), replace next gradient elution；
E, high performance liquid chromatography separation: volume ratio will be used to afford for the chloroform of 7:3-acetone mixed organic solvents
Part is purified using high performance liquid chromatography separation, and the specific method of high performance liquid chromatography separation purifying is: being with volumetric concentration
48% methanol aqueous solution is mobile phase, flow velocity 15ml/min, with 21.2 × 250mm, 5 μm of Zorbax PrepHT GF reverse phase
Preparing column is stationary phase, and UV detector Detection wavelength is 355nm, and each 10 μ L of sample introduction collects the chromatographic peak of 38.5min, more
It is secondary it is cumulative after be evaporated up to the isoflavone compound.
Wherein, the solvent of the step A is the aqueous acetone solution that volumetric concentration is 80%.The organic solvent of the step B
For methylene chloride.
Embodiment 2
A, medicinal extract extracts: pueraria lobata being crushed to 40 mesh, is extracted 5 times with solvent supersonic, every time the quality of Extraction solvent used
It is 4 times of pueraria lobata quality, 60 minutes every time, combined extract simultaneously filtered, and filtrate decompression, which is concentrated into be observed visually, just precipitating
It is precipitated, stands 5h, filter out sediment, gained filtrate is condensed into medicinal extract a later；
B, organic solvent extracts: the water that weight is 2 times of medicinal extract a weight being added into medicinal extract a, is then extracted with organic solvent
5 times, the volume of organic solvent used is identical as water volume every time, merges organic solvent extraction phase, later obtains merging
Organic solvent extraction phase is concentrated under reduced pressure into medicinal extract b；
C, MCI decolourizes: into medicinal extract b, addition is the pure methanol of 5 times of medicinal extract b weight, after medicinal extract b is completely dissolved, upper MCI
Column is that 95% methanol aqueous solution is eluted with volumetric concentration, merges eluent, the eluent after merging is concentrated under reduced pressure later
At medicinal extract c；
D, silica gel column chromatography: medicinal extract c is first dissolved with the methanol that weight is 3 times of medicinal extract c, then with weight be medicinal extract c.2 times
100 mesh silica gel mixed samples, loading carries out column chromatography later, wherein dress column silica gel is 200 mesh, and the weight of used silica gel is medicinal extract c
10 times of weight amounts；The chloroform and acetone mixed organic solvents ladder of 20:1,9:1,8:2,7:3,6:4 and 1:1 are followed successively by with volume ratio
Degree elution, collects the gradient eluent of each gradient and concentration, monitors through TLC, merge identical part；Each gradient elution arrives
TLC contact plate without after point (i.e. the gradient elution not go out substance after), replace next gradient elution；
E, high performance liquid chromatography separation: volume ratio will be used to afford for the chloroform of 7:3-acetone mixed organic solvents
Part is purified using high performance liquid chromatography separation, and the specific method of high performance liquid chromatography separation purifying is: being with volumetric concentration
48% methanol aqueous solution is mobile phase, flow velocity 25ml/min, with 21.2 × 250mm, 5 μm of Zorbax PrepHT GF reverse phase
Preparing column is stationary phase, and UV detector Detection wavelength is 355nm, and each 100 μ L of sample introduction collects the chromatographic peak of 38.5min, more
It is secondary it is cumulative after be evaporated up to the isoflavone compound.
Wherein, the solvent of the step A is acetone.The organic solvent of the step B is ether.
Embodiment 3
A, medicinal extract extracts: pueraria lobata being crushed to 30 mesh, is extracted 3 times with solvent supersonic, every time the quality of Extraction solvent used
It is 3 times of pueraria lobata quality, 40 minutes every time, combined extract simultaneously filtered, and filtrate decompression, which is concentrated into be observed visually, just precipitating
It is precipitated, stands 4h, filter out sediment, gained filtrate is condensed into medicinal extract a later；
B, organic solvent extracts: the water that weight is 1.5 times of medicinal extract a weight being added into medicinal extract a, is then extracted with organic solvent
It takes 4 times, the volume of organic solvent used is identical as water volume every time, merges organic solvent extraction phase, later obtains merging
Organic solvent extraction phase be concentrated under reduced pressure at medicinal extract b；
C, MCI decolourizes: into medicinal extract b, addition is the pure methanol of 4 times of medicinal extract b weight, after medicinal extract b is completely dissolved, upper MCI
Column is that 92% methanol aqueous solution is eluted with volumetric concentration, merges eluent, the eluent after merging is concentrated under reduced pressure later
At medicinal extract c；
D, silica gel column chromatography: medicinal extract c is first 2 times of medicinal extract c of acetone solution with weight, is then c1 times of medicinal extract with weight
90 mesh silica gel mixed samples, loading carries out column chromatography later, wherein dress column silica gel is 180 mesh, and the weight of used silica gel is medicinal extract c
8 times of weight amounts；The chloroform and acetone mixed organic solvents gradient of 20:1,9:1,8:2,7:3,6:4 and 1:1 are followed successively by with volume ratio
Elution, collects the gradient eluent of each gradient and concentration, monitors through TLC, merge identical part；Each gradient elution is to TLC
Contact plate without after point (i.e. the gradient elution not go out substance after), replace next gradient elution；
E, high performance liquid chromatography separation: volume ratio will be used to afford for the chloroform of 7:3-acetone mixed organic solvents
Part is purified using high performance liquid chromatography separation, and the specific method of high performance liquid chromatography separation purifying is: being with volumetric concentration
48% methanol aqueous solution is mobile phase, flow velocity 20ml/min, with 21.2 × 250mm, 5 μm of Zorbax PrepHT GF reverse phase
Preparing column is stationary phase, and UV detector Detection wavelength is 355nm, and each 50 μ L of sample introduction collects the chromatographic peak of 38.5min, more
It is secondary it is cumulative after be evaporated up to the isoflavone compound.
Wherein, the ethanol water that volumetric concentration is 90%；The organic solvent of the step B is petroleum ether.
Embodiment 4
A, medicinal extract extracts: 4.4kg pueraria lobata is crushed to 30 mesh, is extracted 4 times with solvent supersonic, each Extraction solvent used
Quality is 3 times of pueraria lobata quality, and 60 minutes every time, combined extract simultaneously filtered, and filtrate decompression, which is concentrated into be observed visually, just to be had
Precipitation stands 4h, filters out sediment, and gained filtrate is condensed into medicinal extract a later, and medicinal extract a weight is 120g；
B, organic solvent extracts: the water that weight is 2 times of medicinal extract a weight being added into medicinal extract a, is then extracted with organic solvent
5 times, the volume of organic solvent used is identical as water volume every time, merges organic solvent extraction phase, later obtains merging
Organic solvent extraction phase is concentrated under reduced pressure into medicinal extract b, and medicinal extract b weight is 80g；
C, MCI decolourizes: into medicinal extract b, addition is the pure methanol of 3 times of medicinal extract b weight, after medicinal extract b is completely dissolved, upper MCI
Column is that 90% methanol aqueous solution is eluted with volumetric concentration, merges eluent, the eluent after merging is concentrated under reduced pressure later
At medicinal extract c, medicinal extract c weight is 62g；
D, silica gel column chromatography: medicinal extract c first uses the acetone solution of weight 120g, is then mixed with the 100 mesh silica gel that weight is 62g
Sample, loading carries out column chromatography later, wherein dress column silica gel is 200 mesh, and the weight of used silica gel is 400g；Successively with volume ratio
For the chloroform and acetone mixed organic solvents gradient elution of 20:1,9:1,8:2,7:3,6:4 and 1:1, the gradient of each gradient is collected
Eluent is simultaneously concentrated, and monitors through TLC, merges identical part, obtains 6 part A-F；Each gradient elution to TLC contact plate without
After point (after i.e. the gradient elution does not go out substance), next gradient elution is replaced；
E, high performance liquid chromatography separation: volume ratio will be used to afford portion for the chloroform of 7:3-acetone mixed organic solvents
(D part 12g) is divided to purify using high performance liquid chromatography separation, the specific method of high performance liquid chromatography separation purifying is: with volume
The methanol aqueous solution that concentration is 48% is mobile phase, flow velocity 20ml/min, with 21.2 × 250mm, 5 μm of Zorbax PrepHT
GF reverse phase preparative column is stationary phase, and UV detector Detection wavelength is 355nm, and each 50 μ L of sample introduction collects the chromatography of 38.5min
Peak is evaporated up to the isoflavone compound after repeatedly adding up.
Wherein, the solvent of the step A is the aqueous acetone solution that volumetric concentration is 70%.The organic solvent of the step B
For chloroform.
Embodiment 5
A, medicinal extract extracts: 10kg pueraria lobata is crushed to 40 mesh, is extracted 4 times with solvent supersonic, each Extraction solvent used
Quality is 2.5 times of pueraria lobata quality, and 48 minutes every time, combined extract simultaneously filtered, and filtrate decompression, which is concentrated into, to be observed visually just
There is Precipitation, stand 4.5h, filter out sediment, gained filtrate is condensed into medicinal extract a later, medicinal extract a weight is 300g；
B, organic solvent extract: into medicinal extract a be added weight be 350g water, then with organic solvent extract 5 times, every time
The volume of organic solvent used is identical as water volume, merges organic solvent extraction phase, the organic solvent for later obtaining merging
Extraction phase is concentrated under reduced pressure into medicinal extract b, and medicinal extract b weight is 210g；
C, MCI decolourizes: into medicinal extract b, addition is the pure methanol of 3.5 times of medicinal extract b weight, after medicinal extract b is completely dissolved, on
MCI column is that 90% methanol aqueous solution 15L is eluted with volumetric concentration, merges eluent, later subtract the eluent after merging
Pressure is condensed into medicinal extract c, and medicinal extract c weight is 150g；
D, silica gel column chromatography: medicinal extract c is first 2 times of medicinal extract c of acetone solution with weight, is then c1 times of medicinal extract with weight
100 mesh silica gel mixed samples, loading carries out column chromatography later, wherein dress column silica gel is 200 mesh, and the weight of used silica gel is to soak
1000g；The chloroform of 20:1,9:1,8:2,7:3,6:4 and 1:1 are followed successively by with volume ratio and acetone mixed organic solvents gradient is washed
It is de-, the gradient eluent of each gradient and concentration are collected, is monitored through TLC, identical part is merged, obtains 6 part A-F；Each
Gradient elution to TLC contact plate without after point (i.e. the gradient elution not go out substance after), replace next gradient elution；
E, high performance liquid chromatography separation: volume ratio will be used to afford portion for the chloroform of 7:3-acetone mixed organic solvents
(D part 32g) is divided to purify using high performance liquid chromatography separation, the specific method of high performance liquid chromatography separation purifying is: with volume
The methanol aqueous solution that concentration is 48% is mobile phase, flow velocity 20ml/min, with 21.2 × 250mm, 5 μm of Zorbax PrepHT
GF reverse phase preparative column is stationary phase, and UV detector Detection wavelength is 355nm, and each 80 μ L of sample introduction collects the chromatography of 38.5min
Peak is evaporated up to the isoflavone compound after repeatedly adding up.
The solvent of the step A is that volumetric concentration is methanol.The organic solvent of the step B is ethyl acetate.
Embodiment 6
The structure for the isoflavone compound being prepared using 1 method of embodiment is measured by the following method:
The compounds of this invention is yellow jelly；HRESI-MS shows that its quasi-molecular ion peak is 333.0746 [M+Na]+
(calculated value 333.0739), in conjunction with1H NMR and DEPT, which are composed, determines that its molecular formula is C18H14O5, degree of unsaturation 12.
Hydroxyl (3420cm is shown in infrared spectroscopy-1), carbonyl (1718 and 1650cm-1) and aromatic ring (1612,1527 and
1430cm-1) resonance absorbing peak.And ultraviolet spectra has absorption maximum to also illustrate in compound in 210,258,310 and 355nm
There may be aromatic ring structures.
Compound1H and13C H NMR spectroscopy (such as table 1, Fig. 1 and Fig. 2) shows that it contains 18 carbon and 14 hydrogen, including 1
Isoflavones skeleton (C-1~C-10 and C-1 '~C-6 ', H-5, H-8, H-2 ', 6 ' and H-2 ', 6 '), a methoxyl group (δC
56.2 δH3.81s), an acetyl group (δC198.8s and 29.9q, δH2.48s) and a phenolic hydroxyl group (δH11.04).Change
The isoflavones skeleton for closing object can be further by H-5 and C-4, C-6, C-7, C-9, C-10, H-8 and C-1 ", C-6, C-7, C-9, C-
10, H-2 and C-1 ', C-3, C-4, C-9 and H-2 ', 6 ' related to the HMBC of C-3 are confirmed.
Its HMBC Correlated Spectroscopy (such as Fig. 3) is further analyzed, according to methoxyl group hydrogen (δH3.81) with C-6 (δC154.9)
HMBC correlation can speculate methoxy substitution in the position C-6 of isoflavones parent nucleus.Phenolic hydroxyl group is substituted in the position C-4 ' can be by phenolic hydroxyl group hydrogen (δH
11.04) with C-3 ', 5 ' (δCAnd C-4 ' (δ 116.3)C157.4) HMBC correlation confirmation.Finally, acetyl group is substituted in C-7
It can be by H-2 " (δH2.50) with C-7 (δCAnd H-8 (δ 125.7)H7.50) with C-1 " (δC198.8) HMBC correlation obtains
It determines.Typical proton signal H-5 (δ on phenyl ringH 7.30)、H-8(δH 7.50)、H-2,6[δH7.75 (d, J=8.8)] and
H-3,5[(δH6.78 (d, J=8.8)] also support isoflavones parent nucleus on above-mentioned substituent group mode.
So far, the structure of compound is determined, and is named as Compound nomenclature are as follows: 7- acetyl group -4 '-hydroxyl -6- first
Oxygroup-isoflavones.
Embodiment 7
The compound of Example 2-5 preparation is light yellow gum object.Measuring method is same as Example 6, and confirmation is implemented
The compound of example 2-5 preparation is the isoflavone compound --- 7- acetyl group -4 '-hydroxyl -6- methoxy-isofiavone.
Embodiment 8
The isoflavone compound of any preparation in Example 1-5 carries out the additive effect test of cigarette filter, test
Situation is as follows:
For the cigarette " purple cloud " that addition cigarette is the Red River Hong Yun group, with triacetyl glycerine by above-mentioned isoflavones chemical combination
The object solution for being made into 0.1mg/mL.It is uniformly sprayed on filter tow by the 8% of filter tow weight, filter stick is made, so
Cigarette is made by conventional cigarette cigarette in the filter stick afterwards, carries out sensory evaluation, and to be not added with the same volume of the compound
Cigarette is as control.Evaluation and analysis the result shows that: compare with control, add the cigarette smoking of the compounds of this invention moisture feeling have promotion,
Promoting the production of body fluid, it is obvious to act on, and throat's irritation is substantially reduced, and has obvious pharynx-clearing throat-benefiting effect, the results are shown in Table 2.
Embodiment 9
The isoflavone compound of any preparation in Example 1-5 carries out the additive effect test of cigarette filter, test
Situation is as follows:
For the cigarette " purple cloud " that addition cigarette is the Red River Hong Yun group, with triacetyl glycerine by above-mentioned osajin
Close the object solution for being made into 0.2mg/mL.It is uniformly sprayed on filter tow by the 5% of filter tow weight, filter stick is made,
Then cigarette is made by conventional cigarette cigarette in the filter stick, carries out sensory evaluation, and to be not added with the identical of the compound
Cigarette is as control.Evaluation and analysis the result shows that: the moisture feeling for adding the cigarette smoking of the compounds of this invention has promotion, promotes the production of body fluid that it is bright to act on
Aobvious, cigarette smoking throat irritation is substantially reduced, and is had obvious pharynx-clearing throat-benefiting effect, be the results are shown in Table 2.
2 cigarette sense organ Comfort Evaluation of table
Note: score is higher, and product sensory quality is better.
The compounds of this invention application method is without being limited thereto, may also be added on internal lining paper etc..
The basic principles, main features and advantages of the present invention have been shown and described above.The technology of the industry
Personnel are it should be appreciated that the present invention is not limited to the above embodiments, and the above embodiments and description only describe this
The principle of invention, without departing from the spirit and scope of the present invention, various changes and improvements may be made to the invention, these changes
Change and improvement all fall within the protetion scope of the claimed invention.The claimed scope of the invention by appended claims and its
Equivalent thereof.
Claims (7)
1. a kind of isoflavone compound that can improve cigarette smoking throat comfort, which is characterized in that the osajin
The molecular formula for closing object is C18H14O5, Compound nomenclature are as follows: 7- acetyl group -4 '-hydroxyl -6- methoxy-isofiavone, English name are as follows:
7-acetyl-4 '-hydroxyl -6-methoxy-isoflavone, structural formula are as shown in the formula (I):
, formula (I).
2. the preparation method of the isoflavone compound described in claim 1 that can improve cigarette smoking throat comfort, special
Sign is, using pueraria lobata as raw material, through medicinal extract extraction, organic solvent extraction, MCI decoloration, silica gel column chromatography and high performance liquid chromatography
Separating step is made, specifically:
A, medicinal extract extracts: pueraria lobata being crushed to 20 ~ 40 mesh, is extracted 2 ~ 5 times with solvent supersonic, every time the quality of Extraction solvent used
It is 2 ~ 4 times of pueraria lobata quality, 30 ~ 60 minutes every time, combined extract simultaneously filtered, and filtrate decompression, which is concentrated into be observed visually, just to be had
Precipitation stands 3 ~ 5h, filters out sediment, gained filtrate is condensed into medicinal extract a later；
B, organic solvent extract: into medicinal extract a be added weight be 1 ~ 2 times of medicinal extract a weight water, then with organic solvent extraction 3 ~
5 times, the volume of organic solvent used is identical as water volume every time, merges organic solvent extraction phase, later obtains merging
Organic solvent extraction phase is concentrated under reduced pressure into medicinal extract b；
C, MCI decolourizes: into medicinal extract b, addition is the pure methanol of 3 ~ 5 times of medicinal extract b weight, after medicinal extract b is completely dissolved, upper MCI
Column is that 90 ~ 95% methanol aqueous solutions are eluted with volumetric concentration, merges eluent, later that the eluent decompression after merging is dense
Shorten medicinal extract c into；
D, silica gel column chromatography: by silica gel column chromatography on medicinal extract c, dress column silica gel is 160 ~ 200 mesh, and the weight of used silica gel is medicinal extract
6 ~ 10 times of c weight amounts；It is the chloroform and acetone mixed organic solvents gradient elution of 1:0 ~ 0:1 with volume ratio, collects each gradient
Gradient eluent is simultaneously concentrated, and monitors through TLC, merges identical part；Each gradient elution to TLC contact plate without point after, under replacement
One gradient elution；
E, high performance liquid chromatography separation: the part that volume ratio will be used to afford for the chloroform of 7:3-acetone mixed organic solvents
It is purified using high performance liquid chromatography separation to get the isoflavone compound；
The solvent of the step A be volumetric concentration be 70 ~ 100% aqueous acetone solution, volumetric concentration be 90 ~ 100% ethanol water
The methanol aqueous solution that solution or volumetric concentration are 90 ~ 100%；
The organic solvent of the step B is methylene chloride, chloroform, ethyl acetate, ether or petroleum ether.
3. the preparation method of the isoflavone compound according to claim 2 that cigarette smoking throat comfort can be improved,
It is characterized in that, in the D step medicinal extract c before through silica gel column chromatography, first with weight be 1.5 ~ 3 times of medicinal extract c acetone or
Methanol dissolution, is then 0.8 ~ 1.2 times of medicinal extract c of 80 ~ 100 mesh silica gel mixed samples with weight, later loading.
4. the preparation method of the isoflavone compound according to claim 2 that cigarette smoking throat comfort can be improved,
It is characterized in that, in the D step, when gradient elution, the volume ratio of used chloroform and acetone mixed organic solvents is successively
For 20:1,9:1,8:2,7:3,6:4 and 1:1；Each gradient elution to TLC contact plate without point after, replace next gradient elution.
5. the preparation method of the isoflavone compound according to claim 2 that cigarette smoking throat comfort can be improved,
It is characterized in that, the high performance liquid chromatography separation purifying of the E step is using the methanol aqueous solution that volumetric concentration is 48% as flowing
Phase, 15 ~ 25ml/min of flow velocity, with 21.2 × 250mm, 5 μm of Zorbax PrepHT GF reverse phase preparative column is stationary phase, ultraviolet
Detector Detection wavelength is 355nm, and each 10 ~ 100 μ L of sample introduction collects the chromatographic peak of 38.5min, is evaporated after repeatedly adding up.
6. the isoflavone compound described in claim 1 that can improve cigarette smoking throat comfort, which is used as, prepares cigarette filter
The application of additive.
7. the isoflavone compound described in claim 1 that can improve cigarette smoking throat comfort is improving cigarette smoking larynx
Application in portion's comfort.
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| CN107573315B (en) * | 2017-09-13 | 2020-04-21 | 云南中烟工业有限责任公司 | Flavonoid compound in hawthorn as well as preparation method and application thereof |
| CN107573314B (en) * | 2017-09-13 | 2020-04-21 | 云南中烟工业有限责任公司 | Isoamyl flavonoid compound in rose waste residue and preparation method and application thereof |
| CN107778275B (en) * | 2017-10-18 | 2020-08-25 | 云南中烟工业有限责任公司 | Isoflavone compound extracted from rose waste residue and preparation method and application thereof |
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