CN107118194A - A kind of isoflavonoid that can improve cigarette smoking throat comfortableness and preparation method and application - Google Patents
A kind of isoflavonoid that can improve cigarette smoking throat comfortableness and preparation method and application Download PDFInfo
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- CN107118194A CN107118194A CN201710409525.4A CN201710409525A CN107118194A CN 107118194 A CN107118194 A CN 107118194A CN 201710409525 A CN201710409525 A CN 201710409525A CN 107118194 A CN107118194 A CN 107118194A
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- medicinal extract
- isoflavonoid
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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
Abstract
The present invention relates to a kind of isoflavonoid that can improve cigarette smoking throat comfortableness and preparation method and application, belong to Phytochemistry technology technical field.The compound is isolated from the Chinese medicine root of kudzu vine, and its molecular formula is C18H14O5, Compound nomenclature is：The methoxy isoflavone of 7 acetyl 4s ' hydroxyl 6, English is entitled：The methoxy isoflavone of 7 acetyl, 4 ' hodraxy 6, its structural formula such as formula（I）It is shown：, formula（I）.The preparation method of the isoflavonoid, is using the traditional Chinese medicine root of kudzu vine as raw material, is extracted through medicinal extract, organic solvent is extracted, 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 comfortableness, 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
Flavone compound, its preparation method and application.The compound has the effect for significantly improving cigarette smoking throat comfortableness, can
It is used to improve cigarette smoking quality as cigarette filter tip additive.
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 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.The root of kudzu vine is also a kind of important health food simultaneously,
Its medical value is high, have the good reputation of " asia ginseng ", and kudzuvine root starch is referred to as " long-lived powder ", is described as in Japan " royal specially offered
Food ".
Main chemical compositions in the root of kudzu vine are flavones and isoflavonoid (Dai, daidzin, Puerarin, the root of kudzu vine
Element -7- xylosides etc.), the compound also containing the other structures type such as terpene, lactone, sterol.Isoflavones is flavonoid
One kind in thing, during it is plant phenylalanine metabolic process, is cyclized after the extension of cinnamoyl coacetylase side chain and is formed with benzochromone
Phenolic compound based on ring, its 3- phenyl derivatives is isoflavonoid.The life that isoflavonoid is protruded
Reason activity causes the extensive concern of scientific worker.Research shows that kudzuvine root isoflavone has supplement female estrogen, shrinks flat
The effect such as sliding flesh, increase hat CBF, suppression platelet aggregation, hypoglycemic；Isoflavones also has anti-oxidant, antitumor, prevention
Other multiple efficacies such as artery sclerosis, improvement osteoporosis.In addition, isoflavonoid also has the work(for improving people's taste effect
Can, also it is widely used in the food industry.
A kind of present invention isolated isoflavonoid from the root of kudzu vine, the compound is added to cigarette filter
In, cigarette smoking throat excitant can be significantly reduced, with the obvious effect that wets one's whistle.The compounds of this invention is added to cigarette filter
In, cigarette smoking quality can be obviously improved, relevant report is not yet found at present.
The content of the invention
The first object of the present invention is to provide a kind of isoflavonoid；Second purpose is to provide the isoflavones
The preparation method of class compound；3rd purpose is to provide application of the isoflavonoid in cigarette filter, mainly
For reducing cigarette smoking throat excitant, improve cigarette smoking quality.
To achieve the above object, the technical solution adopted by the present invention is as follows：
The first object of the present invention is achieved in that the isoflavonoid is separated from the Chinese medicine root of kudzu vine
Arrive, its molecular formula is C18H14O5, Compound nomenclature is：7- acetyl group -4 '-hydroxyl -6- methoxy-isofiavones, English is entitled：7-
Acetyl-4 '-hodraxy-6-methoxy-isoflavone, shown in its structural formula such as formula (I)：
The compound is light yellow gum thing.
The second object of the present invention is achieved in that the preparation method of the isoflavonoid, be using the root of kudzu vine as
Raw material, is extracted, organic solvent is extracted, MCI decolourizes, silica gel column chromatography and high performance liquid chromatography separation step are made, tool through medicinal extract
Body is：
A, medicinal extract are extracted：The root of kudzu vine is crushed to 20~40 mesh, extracted 2~5 times with solvent supersonic, every time Extraction solvent used
Quality be 2~4 times of root of kudzu vine quality, 30~60 minutes every time, merge extract solution and simultaneously filter, filtrate decompression is concentrated into naked eyes and seen
Observing just has Precipitation, stands 3~5h, filters out sediment, gained filtrate is condensed into medicinal extract a afterwards；
B, organic solvent extraction：The water that weight is 1~2 times of medicinal extract a weight is added into medicinal extract a, organic solvent is then used
Extraction 3~5 times, the volume of organic solvent used is identical with water volume every time, merges organic solvent extraction phase, will merge afterwards
Obtained organic solvent extraction phase is concentrated under reduced pressure into medicinal extract b；
C, MCI decolourize：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 posts, are that 90~95% methanol aqueous solutions are eluted with volumetric concentration, merge eluent, afterwards by the eluent after merging
It is concentrated under reduced pressure into medicinal extract c；
D, silica gel column chromatography：By silica gel column chromatography on medicinal extract c, dress post silica gel is 160~200 mesh, the weight of used silica gel
For 6~10 times of amounts of medicinal extract c weight；Using volume ratio as 1:0~0:1 chloroform and acetone mixed organic solvents gradient elution, is collected
The gradient eluent of each gradient and concentration, are monitored through TLC, merge identical part；Each gradient elution to TLC point plates without point after
(i.e. the gradient elution does not go out after material), changes next gradient elution；
E, high performance liquid chromatography separation：Volume ratio will be used for 7:3 chloroform-acetone mixed organic solvents are afforded
Part produces described isoflavonoid using high performance liquid chromatography separation purifying.
It is further preferred that the aqueous acetone solution that it is 70~100% that the solvent of the step A, which is volumetric concentration, 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 dichloromethane, chloroform, ethyl acetate ether or oil
Ether.
It is further preferred that medicinal extract c is first medicinal extract c 1.5 with weight before through silica gel column chromatography in the D steps
~3 times of acetone or methanol dissolving, is then 0.8~1.2 times of medicinal extract c 80~100 mesh silica gel mixed samples with weight, afterwards
Loading.
It is further preferred that in the D steps, during 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 point plates without (i.e. gradient after point
Can not elute after material), change next gradient elution.
It is further preferred that the high performance liquid chromatography separation purifying of the E steps is the first using volumetric concentration as 48%
Alcohol solution is mobile phase, 15~25ml/min of flow velocity, with 21.2 × 250mm, 5 μm of the anti-phase systems of Zor bax PrepHT GF
Standby post is stationary phase, and UV-detector Detection wavelength is 355nm, each μ L of sample introduction 10~100, collects 38.5min chromatographic peak,
It is evaporated after repeatedly adding up.
Those skilled in the art should know that the technical program is an optimal technical scheme, high performance liquid chromatography separation
Purify the mobile phase not limited to this used.
The structure for the isoflavonoid that method described above is 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), with reference to1H NMR and DEPT spectrum determine that its molecular formula is C18H14O5, degree of unsaturation is 12.
Hydroxyl (3420cm is shown in infrared spectrum-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 that in compound in 210,258,310 and 355nm
It there may be aromatic ring structure.
Compound1H and13C H NMR spectroscopies (such as table 1, Fig. 1 and Fig. 2) show 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) with a phenolic hydroxyl group (δH11.04).Change
The isoflavones skeleton of compound 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 C-3 HMBC 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 correlations can speculate methoxy substitution in the C-6 positions of isoflavones parent nucleus.Phenolic hydroxyl group is substituted in C-4 ' positions can be by phenolic hydroxyl group hydrogen (δH
11.04) with C-3 ', 5 ' (δC116.3) with C-4 ' (δC157.4) HMBC correlations confirm.Finally, acetyl group is substituted in C-7
Can be by H-2 " (δH2.50) with C-7 (δC, and H-8 (δ 125.7)H7.50) with C-1 " (δC198.8) HMBC is related
To determination.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)]
With H-3,5 [(δH6.78 (d, J=8.8)] also support isoflavones parent nucleus on above-mentioned substituent pattern.
So far, the structure of compound is determined, and is named as Compound nomenclature and is：7- acetyl group -4 '-hydroxyl -6- first
Epoxide-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 datas (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).
The compounds of this invention of table 1.1H NMR and13C NMR datas (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. |
What the third object of the present invention was realized in：
The isoflavonoid that the present invention can improve cigarette smoking throat comfortableness is comfortable in improvement cigarette smoking throat
Application in property.
Further, the present invention can improve the isoflavonoid of cigarette smoking throat comfortableness as preparing cigarette filter
The application of additive.The additives of filter tip can be used to improve cigarette smoking throat comfortableness.
The present invention is that cigarette filter is molded the most frequently used plasticizer, and the compounds of this invention in view of triacetyl glycerine
Triacetyl glycerine is dissolved in, in cigarette filter forming process, the compounds of this invention can be added to by triacetyl glycerine
In filter tip.
Compared with prior art, its advantage is the present invention：
Isoflavonoid of the present invention is separated first, is determined by nuclear magnetic resonance and measuring method of mass spectrum
For isoflavonoid, 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 result shows：Compared with control,
Addition the compounds of this invention can reduce cigarette smoking throat excitant, with obvious pharynx-clearing throat-benefiting effect.The compounds of this invention adds
It is added in cigarette filter, is easily realized in technique, do not increase the additional step in production process, cigarette smoking product can be obviously improved
Matter, there is good application prospect.
Brief description of the drawings
Fig. 1 for isoflavonoid of the present invention carbon-13 nmr spectra (13C NMR)；
Fig. 2 for isoflavonoid of the present invention proton nmr spectra (1H NMR)；
The crucial HMBC correlation figures of Fig. 3 isoflavonoids of the present invention.
Embodiment
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 scope.In the examples where no specific technique or condition is specified, according to the technology or condition described by document in the art
Or carried out according to product description.Agents useful for same or the unreceipted production firm person of instrument, are that can be obtained by buying
Conventional products.
The whole common dried products purchased in market of the root of kudzu vine of the present invention.
Isoflavonoid of the present invention, is isolated from the traditional Chinese medicine root of kudzu vine, its molecular formula is
C18H14O5, with following structures：
It is named as：Compound nomenclature is that Compound nomenclature is：7- acetyl group -4 '-hydroxyl -6- methoxy-isofiavones, English
It is entitled：7-acetyl-4′-hodraxy-6-methoxy-isoflavone.
The preparation method of isoflavonoid of the present invention, is using the root of kudzu vine as raw material, is extracted through medicinal extract, organic solvent
Extraction, MCI are decolourized, silica gel column chromatography and high performance liquid chromatography separation step are made, and are specially：
A, medicinal extract are extracted：The root of kudzu vine is crushed to 20~40 mesh, extracted 2~5 times with solvent supersonic, every time Extraction solvent used
Quality be 2~4 times of root of kudzu vine quality, 30~60 minutes every time, merge extract solution and simultaneously filter, filtrate decompression is concentrated into naked eyes and seen
Observing just has Precipitation, stands 3~5h, filters out sediment, gained filtrate is condensed into medicinal extract a afterwards；
B, organic solvent extraction：The water that weight is 1~2 times of medicinal extract a weight is added into medicinal extract a, organic solvent is then used
Extraction 3~5 times, the volume of organic solvent used is identical with water volume every time, merges organic solvent extraction phase, will merge afterwards
Obtained organic solvent extraction phase is concentrated under reduced pressure into medicinal extract b；
C, MCI decolourize：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 posts, are that 90~95% methanol aqueous solutions are eluted with volumetric concentration, merge eluent, afterwards by the eluent after merging
It is concentrated under reduced pressure into medicinal extract c；
D, silica gel column chromatography：By silica gel column chromatography on medicinal extract c, dress post silica gel is 160~200 mesh, the weight of used silica gel
For 6~10 times of amounts of medicinal extract c weight；Using volume ratio as 1:0~0:1 chloroform and acetone mixed organic solvents gradient elution, is collected
The gradient eluent of each gradient and concentration, are monitored through TLC, merge identical part；Each gradient elution to TLC point plates without point after
(i.e. the gradient elution does not go out after material), changes next gradient elution；
E, high performance liquid chromatography separation：Volume ratio will be used for 7:3 chloroform-acetone mixed organic solvents are afforded
Part produces described isoflavonoid using high performance liquid chromatography separation purifying.
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 dichloromethane, chloroform, ethyl acetate ether or petroleum ether.
Medicinal extract c is first 1.5~3 times of medicinal extract c acetone or first with weight before through silica gel column chromatography in the D steps
Alcohol dissolves, and is then 0.8~1.2 times of medicinal extract c 80~100 mesh silica gel mixed samples with weight, afterwards loading.
In the D steps, during 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 point plates without (i.e. the gradient elution does not go out material after point
Afterwards), next gradient elution is changed.
It by 48% methanol aqueous solution of volumetric concentration is flowing that the high performance liquid chromatography separation purifying of the E steps, which is,
Phase, 15~25ml/min of flow velocity, with 21.2 × 250mm, 5 μm of Zorbax PrepHT GF reverse phase preparative columns are stationary phase, purple
External detector Detection wavelength is 355nm, each μ L of sample introduction 10~100, collects 38.5min chromatographic peak, is evaporated after repeatedly adding up.
The compounds of this invention is added in cigarette filter, has the cigarette smoking throat comfortableness effect that improves significantly；
And compared with control, cigarette smoking throat excitant is substantially reduced, with obvious pharynx-clearing throat-benefiting effect.
Embodiment 1
A, medicinal extract are extracted：The root of kudzu vine is crushed to 20 mesh, extracted 2 times with solvent supersonic, every time the quality of Extraction solvent used
For 2 times of root of kudzu vine quality, every time 30 minutes, merge extract solution and filter, filtrate decompression, which is concentrated into be observed visually, just has precipitation
Separate out, stand 3h, filter out sediment, gained filtrate is condensed into medicinal extract a afterwards；
B, organic solvent extraction：The water that weight is 1 times of medicinal extract a weight is added into medicinal extract a, is then extracted with organic solvent
3 times, the volume of organic solvent used is identical with water volume every time, merges organic solvent extraction phase, will merge what is obtained afterwards
Organic solvent extraction phase is concentrated under reduced pressure into medicinal extract b；
C, MCI decolourize：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
Post, is that 90% methanol aqueous solution is eluted with volumetric concentration, merges eluent, the eluent after merging is concentrated under reduced pressure afterwards
Into medicinal extract c；
D, silica gel column chromatography：Medicinal extract c is first 1.5 times of medicinal extract c acetone solution with weight, is then medicinal extract c with weight
0.8 times of 80 mesh silica gel mixed samples, the column chromatography of loading progress afterwards, wherein, dress post silica gel is 160 mesh, and the weight of used silica gel is
6 times of amounts of medicinal extract c weight；20 are followed successively by with volume ratio:1、9:1、8:2、7:3、6:4 and 1:1 chloroform and acetone mixing is organic molten
Agent gradient elution, collects gradient eluent and the concentration of each gradient, is monitored through TLC, merge identical part；Each gradient elution
To TLC point plates without (i.e. the gradient elution does not go out after material) after point, next gradient elution is changed；
E, high performance liquid chromatography separation：Volume ratio will be used for 7:3 chloroform-acetone mixed organic solvents are afforded
Part is using high performance liquid chromatography separation purifying, the specific method of high performance liquid chromatography separation purifying：Using volumetric concentration as
48% methanol aqueous solution be mobile phase, flow velocity 15ml/min, with 21.2 × 250mm, 5 μm of Zorbax PrepHT GF are anti-phase
Post is prepared for stationary phase, UV-detector Detection wavelength is 355nm, each μ L of sample introduction 10, collect 38.5min chromatographic peak, it is many
It is secondary it is cumulative after be evaporated and produce described isoflavonoid.
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 dichloromethane.
Embodiment 2
A, medicinal extract are extracted：The root of kudzu vine is crushed to 40 mesh, extracted 5 times with solvent supersonic, every time the quality of Extraction solvent used
For 4 times of root of kudzu vine quality, every time 60 minutes, merge extract solution and filter, filtrate decompression, which is concentrated into be observed visually, just has precipitation
Separate out, stand 5h, filter out sediment, gained filtrate is condensed into medicinal extract a afterwards；
B, organic solvent extraction：The water that weight is 2 times of medicinal extract a weight is added into medicinal extract a, is then extracted with organic solvent
5 times, the volume of organic solvent used is identical with water volume every time, merges organic solvent extraction phase, will merge what is obtained afterwards
Organic solvent extraction phase is concentrated under reduced pressure into medicinal extract b；
C, MCI decolourize：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
Post, is that 95% methanol aqueous solution is eluted with volumetric concentration, merges eluent, the eluent after merging is concentrated under reduced pressure afterwards
Into 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, afterwards loading carry out column chromatography, wherein, dress post silica gel is 200 mesh, and the weight of used silica gel is medicinal extract c
10 times of amounts of weight；20 are followed successively by with volume ratio:1、9:1、8:2、7:3、6:4 and 1:1 chloroform and acetone mixed organic solvents ladder
Degree elution, collects gradient eluent and the concentration of each gradient, is monitored through TLC, merge identical part；Each gradient elution is arrived
TLC point plates change next gradient elution without (i.e. the gradient elution does not go out after material) after point；
E, high performance liquid chromatography separation：Volume ratio will be used for 7:3 chloroform-acetone mixed organic solvents are afforded
Part is using high performance liquid chromatography separation purifying, the specific method of high performance liquid chromatography separation purifying：Using volumetric concentration as
48% methanol aqueous solution be mobile phase, flow velocity 25ml/min, with 21.2 × 250mm, 5 μm of Zorbax PrepHT GF are anti-phase
Post is prepared for stationary phase, UV-detector Detection wavelength is 355nm, each μ L of sample introduction 100, collect 38.5min chromatographic peak, it is many
It is secondary it is cumulative after be evaporated and produce described isoflavonoid.
Wherein, the solvent of the step A is acetone.The organic solvent of the step B is ether.
Embodiment 3
A, medicinal extract are extracted：The root of kudzu vine is crushed to 30 mesh, extracted 3 times with solvent supersonic, every time the quality of Extraction solvent used
For 3 times of root of kudzu vine quality, every time 40 minutes, merge extract solution and filter, filtrate decompression, which is concentrated into be observed visually, just has precipitation
Separate out, stand 4h, filter out sediment, gained filtrate is condensed into medicinal extract a afterwards；
B, organic solvent extraction：The water that weight is 1.5 times of medicinal extract a weight is added into medicinal extract a, is then extracted with organic solvent
Take 4 times, the volume of organic solvent used is identical with water volume every time, merges organic solvent extraction phase, afterwards obtains merging
Organic solvent extraction phase be concentrated under reduced pressure into medicinal extract b；
C, MCI decolourize：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
Post, is that 92% methanol aqueous solution is eluted with volumetric concentration, merges eluent, the eluent after merging is concentrated under reduced pressure afterwards
Into medicinal extract c；
D, silica gel column chromatography：Medicinal extract c is first 2 times of medicinal extract c acetone solution with weight, is then 1 times of medicinal extract c with weight
90 mesh silica gel mixed samples, afterwards loading carry out column chromatography, wherein, dress post silica gel is 180 mesh, and the weight of used silica gel is medicinal extract c
8 times of amounts of weight；20 are followed successively by with volume ratio:1、9:1、8:2、7:3、6:4 and 1:1 chloroform and acetone mixed organic solvents gradient
Elution, collects gradient eluent and the concentration of each gradient, is monitored through TLC, merge identical part；Each gradient elution is to TLC
Point plate changes next gradient elution without (i.e. the gradient elution does not go out after material) after point；
E, high performance liquid chromatography separation：Volume ratio will be used for 7:3 chloroform-acetone mixed organic solvents are afforded
Part is using high performance liquid chromatography separation purifying, the specific method of high performance liquid chromatography separation purifying：Using volumetric concentration as
48% methanol aqueous solution be mobile phase, flow velocity 20ml/min, with 21.2 × 250mm, 5 μm of Zorbax PrepHT GF are anti-phase
Post is prepared for stationary phase, UV-detector Detection wavelength is 355nm, each μ L of sample introduction 50, collect 38.5min chromatographic peak, it is many
It is secondary it is cumulative after be evaporated and produce described isoflavonoid.
Wherein, volumetric concentration is 90% ethanol water；The organic solvent of the step B is petroleum ether.
Embodiment 4
A, medicinal extract are extracted：The 4.4kg roots of kudzu vine are crushed to 30 mesh, extracted 4 times with solvent supersonic, each Extraction solvent used
Quality is 3 times of root of kudzu vine quality, 60 minutes every time, merges extract solution and filters, 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 afterwards, and medicinal extract a weight is 120g；
B, organic solvent extraction：The water that weight is 2 times of medicinal extract a weight is added into medicinal extract a, is then extracted with organic solvent
5 times, the volume of organic solvent used is identical with water volume every time, merges organic solvent extraction phase, will merge what is obtained afterwards
Organic solvent extraction phase is concentrated under reduced pressure into medicinal extract b, and medicinal extract b weight is 80g；
C, MCI decolourize：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
Post, is that 90% methanol aqueous solution is eluted with volumetric concentration, merges eluent, the eluent after merging is concentrated under reduced pressure afterwards
Into medicinal extract c, medicinal extract c weight is 62g；
D, silica gel column chromatography：Medicinal extract c first uses weight 120g acetone solution, is then mixed with the 100 mesh silica gel that weight is 62g
Sample, the column chromatography of loading progress afterwards, wherein, dress post silica gel is 200 mesh, and the weight of used silica gel is 400g；With volume ratio successively
For 20:1、9:1、8:2、7:3、6:4 and 1:1 chloroform and acetone mixed organic solvents gradient elution, collects the gradient of each gradient
Eluent is simultaneously concentrated, and is monitored through TLC, is merged identical part, is obtained 6 part A-F；Each gradient elution to TLC point plates without
After point (i.e. the gradient elution does not go out after material), next gradient elution is changed；
E, high performance liquid chromatography separation：Volume ratio will be used for 7:3 chloroform-acetone mixed organic solvents afford portion
(D part 12g) is divided to be purified 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 columns are stationary phase, and UV-detector Detection wavelength is 355nm, each μ L of sample introduction 50, collects 38.5min chromatogram
Peak, is evaporated after repeatedly adding up and produces described isoflavonoid.
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 are extracted：The 10kg roots of kudzu vine are crushed to 40 mesh, extracted 4 times with solvent supersonic, each Extraction solvent used
Quality is 2.5 times of root of kudzu vine quality, 48 minutes every time, merges extract solution and filters, 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 afterwards, medicinal extract a weight is 300g；
B, organic solvent extraction：The water that weight is 350g is added into medicinal extract a, then with organic solvent extraction 5 times, every time
The volume of organic solvent used is identical with water volume, merges organic solvent extraction phase, will merge obtained organic solvent afterwards
Extraction phase is concentrated under reduced pressure into medicinal extract b, and medicinal extract b weight is 210g；
C, MCI decolourize：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 posts, are that 90% methanol aqueous solution 15L is eluted with volumetric concentration, merge eluent, afterwards 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 acetone solution with weight, is then 1 times of medicinal extract c with weight
100 mesh silica gel mixed samples, afterwards loading carry out column chromatography, wherein, dress post silica gel is 200 mesh, and the weight of used silica gel is leaching
1000g；20 are followed successively by with volume ratio:1、9:1、8:2、7:3、6:4 and 1:1 chloroform and acetone mixed organic solvents gradient is washed
It is de-, gradient eluent and the concentration of each gradient are collected, is monitored through TLC, merges identical part, obtains 6 part A-F；Each
Gradient elution, without (i.e. the gradient elution does not go out after material) after point, changes next gradient elution to TLC point plates；
E, high performance liquid chromatography separation：Volume ratio will be used for 7:3 chloroform-acetone mixed organic solvents afford portion
(D part 32g) is divided to be purified 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 columns are stationary phase, and UV-detector Detection wavelength is 355nm, each μ L of sample introduction 80, collects 38.5min chromatogram
Peak, is evaporated after repeatedly adding up and produces described isoflavonoid.
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 of the isoflavonoid prepared using the method for embodiment 1 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), with reference to1H NMR and DEPT spectrum determine that its molecular formula is C18H14O5, degree of unsaturation is 12.
Hydroxyl (3420cm is shown in infrared spectrum-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 that in compound in 210,258,310 and 355nm
It there may be aromatic ring structure.
Compound1H and13C H NMR spectroscopies (such as table 1, Fig. 1 and Fig. 2) show 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) with a phenolic hydroxyl group (δH11.04).Change
The isoflavones skeleton of compound 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 C-3 HMBC 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 correlations can speculate methoxy substitution in the C-6 positions of isoflavones parent nucleus.Phenolic hydroxyl group is substituted in C-4 ' positions can be by phenolic hydroxyl group hydrogen (δH
11.04) with C-3 ', 5 ' (δC116.3) with C-4 ' (δC157.4) HMBC correlations confirm.Finally, acetyl group is substituted in C-7
Can be by H-2 " (δH2.50) with C-7 (δC, and H-8 (δ 125.7)H7.50) with C-1 " (δC198.8) HMBC is related
To determination.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)]
With H-3,5 [(δH6.78 (d, J=8.8)] also support isoflavones parent nucleus on above-mentioned substituent pattern.
So far, the structure of compound is determined, and is named as Compound nomenclature and is：7- acetyl group -4 '-hydroxyl -6- first
Epoxide-isoflavones.
Embodiment 7
Compound prepared by Example 2-5, is light yellow gum thing.Assay method is same as Example 6, confirms to implement
Compound prepared by example 2-5 is the isoflavonoid --- 7- acetyl group -4 '-hydroxyl -6- methoxy-isofiavones.
Embodiment 8
The isoflavonoid of any preparation in Example 1-5 carries out the additive effect experiment of cigarette filter, experiment
Situation is as follows：
For the cigarette " purple cloud " that addition cigarette is Hong Yun Red River group, with triacetyl glycerine by above-mentioned isoflavones chemical combination
The thing solution for being made into 0.1mg/mL.Uniformly it is sprayed onto by the 8% of filter tow weight on filter tow, filter stick is made, so
Cigarette is made by conventional cigarette cigarette in the filter stick 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, add the compounds of this invention cigarette smoking moisture feeling have lifting,
The effect of promoting the production of body fluid is obvious, and throat's excitant is substantially reduced, and with obvious pharynx-clearing throat-benefiting effect, the results are shown in Table 2.
Embodiment 9
The isoflavonoid of any preparation in Example 1-5 carries out the additive effect experiment of cigarette filter, experiment
Situation is as follows：
For the cigarette " purple cloud " that addition cigarette is Hong Yun Red River group, with triacetyl glycerine by above-mentioned osajin
The compound solution for being made into 0.2mg/mL.Uniformly it is sprayed onto by the 5% of filter tow weight on filter tow, 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 used as control.Evaluation and analysis result shows：Adding the moisture feeling of the cigarette smoking of the compounds of this invention has lifting, the effect of promoting the production of body fluid bright
Aobvious, cigarette smoking throat excitant is substantially reduced, and with obvious pharynx-clearing throat-benefiting effect, the results are shown in Table 2.
The cigarette sense organ Comfort Evaluation of table 2
Note：Fraction is higher, and product sensory quality is better.
The compounds of this invention application process not limited to this, may also be added to internal lining paper first-class.
General principle, principal character and the advantages of the present invention of the present invention has 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 simply explanation described in above-described embodiment and specification is originally
The principle of invention, without departing from the spirit and scope of the present invention, various changes and modifications of the present invention are possible, 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 (9)
1. a kind of can improve the isoflavonoid of cigarette smoking throat comfortableness, it is characterised in that the osajin
The molecular formula of compound is C18H14O5, Compound nomenclature is：7- acetyl group -4 '-hydroxyl -6- methoxy-isofiavones, English is entitled：
7-acetyl-4 '-hodraxy-6-methoxy-isoflavone, its structural formula such as formula（I）It is shown：
, formula（I）.
2. the preparation method of the isoflavonoid that can improve cigarette smoking throat comfortableness described in claim 1, it is special
Levy and be, using the root of kudzu vine as raw material, extracted through medicinal extract, organic solvent extraction, MCI decolourize, silica gel column chromatography and high performance liquid chromatography
Separating step is made, and is specially：
A, medicinal extract are extracted：The root of kudzu vine is crushed to 20 ~ 40 mesh, extracted 2 ~ 5 times with solvent supersonic, every time the quality of Extraction solvent used
For 2 ~ 4 times of root of kudzu vine quality, every time 30 ~ 60 minutes, merge extract solution and filter, 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 afterwards；
B, organic solvent extraction：Into medicinal extract a add 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 with water volume every time, merges organic solvent extraction phase, will merge what is obtained afterwards
Organic solvent extraction phase is concentrated under reduced pressure into medicinal extract b；
C, MCI decolourize：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
Post, is that 90 ~ 95% methanol aqueous solutions are eluted with volumetric concentration, merges eluent, afterwards 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 post silica gel is 160 ~ 200 mesh, and the weight of used silica gel is medicinal extract
6 ~ 10 times of amounts of c weight；Using volume ratio as 1:0~0:1 chloroform and acetone mixed organic solvents gradient elution, collects each gradient
Gradient eluent is simultaneously concentrated, and is monitored through TLC, merges identical part；Each gradient elution to TLC point plates without point after, under replacing
One gradient elution；
E, high performance liquid chromatography separation：Volume ratio will be used for 7:The part that 3 chloroform-acetone mixed organic solvents are afforded
Purified using high performance liquid chromatography separation, produce described isoflavonoid.
3. the preparation method of the isoflavonoid according to claim 2 that cigarette smoking throat comfortableness can be improved,
Characterized in that, the aqueous acetone solution that it is 70 ~ 100% that the solvent of the step A, which is volumetric concentration, volumetric concentration are 90 ~ 100%
Ethanol water or the methanol aqueous solution that volumetric concentration is 90 ~ 100%.
4. the preparation method of the isoflavonoid according to claim 2 that cigarette smoking throat comfortableness can be improved,
Characterized in that, the organic solvent of the step B is dichloromethane, chloroform, ethyl acetate, ether or petroleum ether.
5. the preparation method of the isoflavonoid according to claim 2 that cigarette smoking throat comfortableness can be improved,
Characterized in that, in the D steps medicinal extract c before through silica gel column chromatography, first with weight be 1.5 ~ 3 times of medicinal extract c acetone or
Methanol dissolves, and is then 0.8 ~ 1.2 times of medicinal extract c 80 ~ 100 mesh silica gel mixed samples with weight, afterwards loading.
6. the preparation method of the isoflavonoid according to claim 2 that cigarette smoking throat comfortableness can be improved,
Characterized in that, in the D steps, during 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 point plates without point after, the next gradient elution of replacing.
7. the preparation method of the isoflavonoid according to claim 2 that cigarette smoking throat comfortableness can be improved,
Characterized in that, it by 48% methanol aqueous solution of volumetric concentration is flowing that the high performance liquid chromatography separation purifying of the E steps, which is,
Phase, 15 ~ 25ml/min of flow velocity, with 21.2 × 250mm, 5 μm of Zorbax PrepHT GF reverse phase preparative columns are stationary phase, ultraviolet
Detector Detection wavelength is 355nm, each μ L of sample introduction 10 ~ 100, collects 38.5min chromatographic peak, is evaporated after repeatedly adding up.
8. the isoflavonoid that can improve cigarette smoking throat comfortableness described in claim 1 is as preparing cigarette filter
The application of additive.
9. the isoflavonoid that can improve cigarette smoking throat comfortableness described in claim 1 is improving cigarette smoking larynx
Application in portion's comfortableness.
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