CN108084137A - A kind of hydroxypropyl isoflavone compound and preparation method and application - Google Patents

A kind of hydroxypropyl isoflavone compound and preparation method and application Download PDF

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Publication number
CN108084137A
CN108084137A CN201711354150.2A CN201711354150A CN108084137A CN 108084137 A CN108084137 A CN 108084137A CN 201711354150 A CN201711354150 A CN 201711354150A CN 108084137 A CN108084137 A CN 108084137A
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medicinal extract
hydroxypropyl
silica gel
organic solvent
weight
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Inventor
陈章玉
向海英
凌军
高茜
张天栋
蒋次清
王晋
许�永
孔维松
周敏
杨叶昆
李雪梅
胡秋芬
杨光宇
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China Tobacco Yunnan Industrial Co Ltd
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China Tobacco Yunnan Industrial Co Ltd
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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
    • 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
    • A24D3/02—Manufacture of tobacco smoke filters
    • A24D3/0204—Preliminary operations before the filter rod forming process, e.g. crimping, blooming
    • A24D3/0212—Applying additives to filter materials
    • A24D3/022—Applying additives to filter materials with liquid additives, e.g. application of plasticisers
    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention relates to a kind of hydroxypropyl isoflavone compounds and preparation method and application, belong to technical field of phytochemistry.The compound is isolated from traditional medicinal and edible plant pawpaw, and Compound nomenclature is：6 hydroxyl 7 (3 hydroxypropyl) 4 ' methoxy isoflavones, English are entitled：6 hydroxy 7 (3 hydroxypropyl) 4 ' methoxy isoflavone, molecular formula C19H18O5, structural formula such as formula（I）It is shown：, formula（I）.The compounds of this invention is using pawpaw as raw material, is extracted through medicinal extract, organic solvent extracts, MCI decolourizes, silica gel column chromatography and high pressure liquid chromatography separating step obtain.The compound is added in cigarette filter to compare with control, and the sweet sense of cigarette smoking has that promotion, the effect of promoting the production of body fluid are apparent, and irritation is reduced, suction comfort be improved significantly.

Description

A kind of hydroxypropyl isoflavone compound and preparation method and application
Technical field
The invention belongs to technical field of phytochemistry, and in particular to one kind is extracted for the first time from medicinal and edible plant pawpaw Hydroxypropyl isoflavone compound, its preparation method and the application arrived.The compound is added in cigarette filter rod, cigarette smoking Sweet sense has that promotion, the effect of promoting the production of body fluid are apparent, and irritation is reduced, suction comfort be improved significantly.
Background technology
Pawpaw (scientific name：Chaenomeles sinensis (Thouin) Koehne), for rosaceae chaenomeles plant patch stalk The fruit of Malus spectabilis.Pawpaw is ellipse, and 10-15 centimetres long, dark yellow is wooden, sweet and sour, and fragrance is strong.It has appetizing, chest enlarge The health-care effects such as beauty, treatment rheumatalgia.Pawpaw can also make preserved fruit, fruit wine, steep in wine, and can also cook, and do various wood Melon chicken, pawpaw fish, pawpaw stewed pig's feet etc..Its delicious flavour is the green fruit that tool is delicious, medical value is the whole body.Pawpaw It is full of nutrition, rich in the multiple efficacies ingredient such as vitamin, organic acid, flavones, triterpenes, saponins, carbohydrate, tannin, have and protect Liver, antibacterial, it is antitumor the effects that, can control arthralgia pain due to rheumatism, vague aching of limbs, muscle arteries and veins contraction, vomit and diarrhoea convulsion and tinea pedis oedema.Pawpaw carries Object is taken also to be commonly used for cigarette additive, papaya extractives are added in cigarette has soft flue gas, reduces flue gas irritation, supplement Cigarette perfume, the effect of plentiful flue gas.
It is mutual by central thricarbon atom that isoflavone compound refers to two phenyl ring (A- and B- rings) with phenolic hydroxyl group A series of compounds to link, basic parent nucleus are 2- phenyl chromones.It is often connected in isoflavone compound structure The functional groups such as phenolic hydroxyl group, methoxyl group, methyl, isopentene group.In addition, it is also often combined into glycosides with sugar.The effect of flavones is multi-party Face, it is a kind of very strong antioxidant, and the ability for preventing oxidation is ten times of vitamin E or more, and this antioxidation can To prevent the degeneration of cell, aging, the generation of cancer can be also prevented.Flavones can improve blood circulation, reduce cholesterol, improve Cardiovascular and cerebrovascular disease.In addition, isoflavone compound also has prominent improvement sense of taste effect, the taste of some isoflavone compounds Feel that performance is very special, there is a kind of natural sweet taste after entrance.Flavones contained by pueraria lobata is exactly that it can be returned the main reason for sweet, and And flavones content is higher, return it is sweet more apparent, smell is more mellow.A kind of present invention isolated different Huang of hydroxypropyl from pawpaw Ketone compounds, the compound are added in cigarette filter, and the moisture feeling of cigarette smoking has promotion, the effect of promoting the production of body fluid apparent, aspirates Comfort be improved significantly.The compound and its application in terms of cigarette smoking are there is not yet relevant report.
The content of the invention
The first object of the present invention is to provide a kind of hydroxypropyl isoflavone compound；Second be designed to provide it is described The preparation method of hydroxypropyl isoflavone compound；3rd, which is designed to provide the hydroxypropyl isoflavone compound conduct, changes The application of kind cigarette suction comfort additive, after adding the compounds of this invention, the sweet sense of cigarette smoking has promotion, promote the production of body fluid work With apparent, irritation is reduced, suction comfort be improved significantly.
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 hydroxypropyl isoflavone compound is same from traditional medicine food Isolated, molecular formula C in the plant pawpaw of source19H18O5, shown in structural formula such as formula (I)：
The compound is light yellow gum object, is named as：6- hydroxyls -7- (3- hydroxypropyls) -4 '-methoxy-isofiavone, English Literary fame is：6-hydroxy-7-(3-hydroxypropyl)-4′-methoxy-isoflavone.
The second object of the present invention is achieved in that the preparation method of the hydroxypropyl isoflavone compound, with Pawpaw is raw material, is extracted through medicinal extract, organic solvent extracts, MCI decolourizes, silica gel column chromatography and high performance liquid chromatography preparative separation walk It is rapid to be made, specifically include following steps：
A, medicinal extract extracts：Fresh pawpaw is crushed to 20~40 mesh, is extracted 2~5 times with solvent supersonic, every time extraction used The quality of solvent is 3-6 times of pawpaw quality, and each extraction time is 30~60 minutes, merges extracting solution and filters, filtrate subtracts Pressure, which is concentrated into be observed visually, just Precipitation, stands 20~60 minutes, filters out sediment, afterwards that gained filtrate decompression is dense Shorten medicinal extract a into；
B, organic solvent extracts：The water that weight is 1~2 times of medicinal extract a weight is added in into medicinal extract a, then uses 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 afterwards Obtained organic solvent extraction phase is concentrated under reduced pressure into medicinal extract b；
C, MCI decolourizes：It is that the volumetric concentration of 3~5 times of medicinal extract b weight is 80% methanol aqueous solution to be added in into medicinal extract b, After medicinal extract b is completely dissolved, upper MCI columns are eluted for 90%~95% methanol aqueous solution with volumetric concentration, merge elution Eluent after merging is concentrated under reduced pressure into medicinal extract c by liquid afterwards；
D, silica gel column chromatography：By silica gel column chromatography on medicinal extract c, column silica gel is filled as 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, each Gradient elution to TLC contact plates without point after, replace next gradient elution；The gradient eluent of each gradient and concentration are collected, is supervised through TLC It surveys, merges identical part；
E, high performance liquid chromatography separation：Volume ratio will be used as 7:3 chloroform-acetone mixed organic solvents afford Part is purified using high performance liquid chromatography separation to get the hydroxypropyl isoflavone compound.
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 stone Oily 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 80~100 mesh silica gel mixed samples of 0.8~1.2 times of medicinal extract c 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 to TLC contact plates without point after, replacement is next Gradient elution.
It is further preferred that the E steps high performance liquid chromatography separation purifying be using volumetric concentration as 54% first Alcohol solution is mobile phase, flow velocity 20ml/min, with 21.2 × 250mm, 5 μm of Zorba x PrepHT GF reverse phase preparative columns For stationary phase, UV detector Detection wavelength is 338nm, each 10~100 μ L of sample introduction, collects the chromatographic peak of 30.2min, repeatedly It is evaporated after cumulative.
The structure of the preparation method for the hydroxypropyl isoflavone compound that method described above is prepared is by the following method It is measured：
The present invention is light yellow gum object；
HRESI-MS shows that its quasi-molecular ion peak is 349.1046 [M+Na]+(calculated value 349.1052), with reference to1H NMR It is composed with DEPT and determines that its molecular formula is C19H18O5, degree of unsaturation 11.
Hydroxyl (3416), carbonyl (1655) and aromatic ring (1614,1563 and 1480cm are shown in infrared spectrum-1) resonance Absworption peak.And ultraviolet spectra has absorption maximum to also illustrate that there may be aromatic ring structures in compound in 210,260,338nm.
Compound1H and13C H NMR spectroscopies data (such as table 1, Fig. 1 and Fig. 2) show that it contains 19 carbon and 18 hydrogen, including 11,2,4,5- quaternary phenyl ring (C-5~C-10, H-5, H-8), 1 Isosorbide-5-Nitrae-disubstituted phenyl ring (C-1'~C-6', H- 2', 6' and H-3', 5'), 1 α, beta-unsaturated carbonyl (C-2, C-3, C-4, H-3), 1 3- hydroxypropyl (C-1 "~C-3 ", H2- 1 "~H2- 3 "), 1 methoxyl group (δC56.4q δH3.79s) and 1 phenolic hydroxyl group (δH10.76s).According to typical 2 A phenyl ring, α, beta-unsaturated carbonyl signal, it is isoflavone compound that can speculate the compound.
According to H-2 and C-3, C-4, C-9, C-1 ', H-5 and C-4, C-9, C-10, H-8 and C-6, C-7, C-9, C-10, with And H-2', 6 ' (such as Fig. 3) related to the HMBC of C-3 may further confirm that compound is osajin structure.The parent of compound After determining, remaining substituent group, 3 hydroxypropyls, methoxyl group and phenolic hydroxyl group can be considered the substituent group on flavones.
Methoxyl group hydrogen (δ can be observed in (such as Fig. 3) in the HMBC spectrums of compoundH3.79) with C-4'(δC160.3) HMBC Correlation can speculate the methoxy substitution at C-4'；According to H2-1”(δH2.72) with C-6 (δC 150.2)、C-7(δC And C-8 (δ 130.3)C116.7), H2-2”(δH1.87) with C-7 (δCAnd H-8 (δ 130.3)HAnd C-1 " (δ 6.70)C 28.9) HMBC is related, it can be verified that 3- hydroxypropyls are substituted in C-7.Phenolic hydroxyl group is substituted in C-6 can be by phenolic hydroxyl group hydrogen (δH And C-5 (δ 10.76)C 114.1)、C-6(δ CAnd C-7 (δ 150.2)C130.3) HMBC correlations are confirmed.In addition it is typical Phenyl ring on proton signal [H-5, δH7.07s；H-8,δH6.70s；H-2 ', 6 ', δH7.72(d)8.8；H-3 ', 5 ', δH 6.79 (d) 8.8] also susceptible of proof compound A rings be 6,7- positions two substitute, B rings for 4'- it is monosubstituted.
So far, the structure of compound is determined, and is named as：6- hydroxyls -7- (3- hydroxypropyls) -4 '-methoxyl group-different Huang Ketone.
1. the compounds of this invention of table1H NMR and13C NMR datas (C5D5N)
No. δC(mult.) δH(mult,J,Hz) No. δC(mult.) δH(mult,J,Hz)
2 152.4d 7.81s 1′ 124.5s
3 123.9s 2′,6′ 129.1d 7.72(d)8.8
4 175.9s 3′,5′ 114.9d 6.79(d)8.8
5 114.1d 7.07s 4′ 160.3s
6 150.2s 1″ 28.9t 2.72(t)7.8
7 130.3s 2″ 38.9t 1.87m
8 116.7d 6.70s 3″ 63.4t 3.60(t)6.6
9 149.1s OMe-4′ 56.4q 3.79s
10 121.2s Ar-OH-6 10.76s
Infrared, the ultraviolet and mass spectrometric data of compound：UV (methanol), λmax(logε)338(3.28)、260(3.64)、210 (4.31)nm；IR (pressing potassium bromide troche)：νmax 3416、3052、2930、1655、1614、1563、1480、1439、1148、 1065cm-1；1H and13C NMR datas (500 and 125MHz, (C5D5N), it is shown in Table 1；349 [M+ of positive ion mode ESIMS m/z Na]+；Positive ion mode HRESIMS m/z 349.1046 [M+Na]+(calculated value C19H18O5, 349.1052).
The third object of the present invention is achieved in that the hydroxypropyl isoflavone compound adds as cigarette filter Add the application of agent.Most common plasticizer is molded for cigarette filter in view of triacetyl glycerine, and the compounds of this invention is molten In triacetyl glycerine, in cigarette filter forming process, the compounds of this invention is added to filter tip by triacetyl glycerine In.Above-mentioned hydroxypropyl isoflavone compound is used to the solution for being made into 0.1-0.5mg/mL with triacetyl glycerine.Press filter tip silk The 5-10% of Shu Chongliang is uniformly sprayed onto on filter tow, and filter stick is made, and the filter stick then is passed through conventional cigarette cigarette It is made cigarette, carries out sensory evaluation, and to be not added with the identical cigarette of the compound as compareing.
Compared with prior art, the present invention its advantage is：
Hydroxypropyl isoflavone compound of the present invention is separated for the first time, passes through nuclear magnetic resonance and mass spectroscopy side Method is determined as isoflavone compound, and characterizes its structure.The compounds of this invention is added to cigarette by triacetyl glycerine In filter tip, the identical cigarette to be not added with the compound carries out sensory evaluation as control.Evaluation and analysis the result shows that：And control It comparing, adds the cigarette of the compounds of this invention, the sweet sense of suction has promotion, the effect of promoting the production of body fluid substantially, and irritation is reduced, Aspirate comfort be improved significantly.
The compounds of this invention is added in cigarette filter, easy to implement in technique, does not increase the additional step in production process Suddenly, cigarette smoking quality can be obviously improved, there is good application prospect.
Description of the drawings
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 related figures of the crucial HMBC of Fig. 3 isoflavone compounds of the present invention.
Specific 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 described technology of document in the art or condition Or it is carried out according to product description.Production firm person is not specified in material therefor or equipment, and being can be by buying what is obtained Conventional products.
Pawpaw platymiscium of the present invention can realize the present invention from area and kind limitation.
Embodiment 1
Pawpaw sample is adopted in Dali.
A kind of preparation method of hydroxypropyl isoflavone compound using pawpaw as raw material, is extracted, organic solvent extraction through medicinal extract Take, MCI decolorations, silica gel column chromatography and high performance liquid chromatography preparative separation step are made, specifically include following steps：
A, medicinal extract extracts：Fresh pawpaw is crushed to 20~40 mesh, is extracted 2 times with solvent supersonic, extraction used is molten every time The quality of agent is 3 times of pawpaw quality, and each extraction time is 30 minutes, merges extracting solution and filters, filtrate decompression is concentrated into Being observed visually just has Precipitation, stands 20 minutes, filters out sediment, gained filtrate decompression is condensed into medicinal extract a afterwards；
B, organic solvent extracts：The water that weight is 1 times of medicinal extract a weight is added in into medicinal extract a, is then extracted with organic solvent 3~5 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 decolourizes：It is that the volumetric concentration of 3 times of medicinal extract b weight is 80% methanol aqueous solution to be added in into medicinal extract b, is treated After medicinal extract b is completely dissolved, upper MCI columns are eluted for 90% methanol aqueous solution with volumetric concentration, merge eluent, afterwards will Eluent after merging is concentrated under reduced pressure into medicinal extract c；
D, silica gel column chromatography：Medicinal extract c is first the acetone or first of 1.5 times of medicinal extract c with weight before through silica gel column chromatography Alcohol dissolves, and is then the 80 mesh silica gel mixed samples of 0.8 times of medicinal extract c with weight, and loading will carry out silica gel column chromatography afterwards, fills column silicon Glue 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 Hes 1:1 chloroform and acetone mixed organic solvents gradient elution, after each gradient elution to TLC contact plates is without point, replaces next gradient Elution；The gradient eluent of each gradient and concentration are collected, is monitored through TLC, merges identical part；
E, high performance liquid chromatography separation：Volume ratio will be used as 7:3 chloroform-acetone mixed organic solvents afford Part is purified using high performance liquid chromatography separation to get the hydroxypropyl isoflavone compound；
The high performance liquid chromatography separation purifying is using the methanol aqueous solution that volumetric concentration is 54% as 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 detects Wavelength is 338nm, each 30 μ L of sample introduction, collects the chromatographic peak of 30.2min, is evaporated after repeatedly adding up.
Wherein, the solvent of the step A is acetone.The organic solvent of the step B is dichloromethane.
Embodiment 2
Pawpaw sample is adopted in Dali.
A kind of preparation method of hydroxypropyl isoflavone compound using pawpaw as raw material, is extracted, organic solvent extraction through medicinal extract Take, MCI decolorations, silica gel column chromatography and high performance liquid chromatography preparative separation step are made, specifically include following steps：
A, medicinal extract extracts：Fresh pawpaw is crushed to 20~40 mesh, is extracted 5 times with solvent supersonic, extraction used is molten every time The quality of agent is 3.5 times of pawpaw quality, and each extraction time is 60 minutes, merges extracting solution and filters, filtrate decompression concentration Just there is Precipitation to being observed visually, stand 60 minutes, filter out sediment, gained filtrate decompression is condensed into medicinal extract a afterwards；
B, organic solvent extracts：The water that weight is 2 times of medicinal extract a weight is added in into medicinal extract a, is then extracted with organic solvent 3~5 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 decolourizes：It is that the volumetric concentration of 5 times of medicinal extract b weight is 80% methanol aqueous solution to be added in into medicinal extract b, is treated After medicinal extract b is completely dissolved, upper MCI columns are eluted for 95% methanol aqueous solution with volumetric concentration, merge eluent, afterwards will Eluent after merging is concentrated under reduced pressure into medicinal extract c；
D, silica gel column chromatography：Medicinal extract c is first the acetone or methanol of 3 times of medicinal extract c with weight before through silica gel column chromatography Dissolving, is then the 100 mesh silica gel mixed samples of 1.2 times of medicinal extract c with weight, and loading will carry out silica gel column chromatography afterwards, fills column silica gel For 200 mesh, the weight of used silica gel is 10 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 Hes 1:1 chloroform and acetone mixed organic solvents gradient elution, after each gradient elution to TLC contact plates is without point, replaces next gradient Elution；The gradient eluent of each gradient and concentration are collected, is monitored through TLC, merges identical part；
E, high performance liquid chromatography separation：Volume ratio will be used as 7:3 chloroform-acetone mixed organic solvents afford Part is purified using high performance liquid chromatography separation to get the hydroxypropyl isoflavone compound；
The high performance liquid chromatography separation purifying is using the methanol aqueous solution that volumetric concentration is 54% as 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 detects Wavelength is 338nm, each 50 μ L of sample introduction, collects the chromatographic peak of 30.2min, is evaporated after repeatedly adding up.
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 chloroform.
Embodiment 3
Pawpaw sample is adopted in enshi.
A kind of preparation method of hydroxypropyl isoflavone compound using pawpaw as raw material, is extracted, organic solvent extraction through medicinal extract Take, MCI decolorations, silica gel column chromatography and high performance liquid chromatography preparative separation step are made, specifically include following steps：
A, medicinal extract extracts：Fresh pawpaw is crushed to 20~40 mesh, is extracted 2~5 times with solvent supersonic, every time extraction used The quality of solvent is 4.5 times of pawpaw quality, and each extraction time is 40 minutes, merges extracting solution and filters, filtrate decompression is dense It is reduced to be observed visually and just has Precipitation, stand 40 minutes, filter out sediment, gained filtrate decompression is condensed into medicinal extract afterwards a；
B, organic solvent extracts：The water that weight is 1.2 times of medicinal extract a weight is added in into medicinal extract a, is then extracted with organic solvent It takes 3~5 times, the volume of organic solvent used is identical with water volume every time, merges organic solvent extraction phase, will merge afterwards To organic solvent extraction phase be concentrated under reduced pressure into medicinal extract b；
C, MCI decolourizes：It is that the volumetric concentration of 4 times of medicinal extract b weight is 80% methanol aqueous solution to be added in into medicinal extract b, is treated After medicinal extract b is completely dissolved, upper MCI columns are eluted for 92% methanol aqueous solution with volumetric concentration, merge eluent, afterwards will Eluent after merging is concentrated under reduced pressure into medicinal extract c；
D, silica gel column chromatography：Medicinal extract c is first the acetone or methanol of 12 times of medicinal extract c with weight before through silica gel column chromatography Dissolving, is then the 90 mesh silica gel mixed samples of 1 times of medicinal extract c with weight, and loading will carry out silica gel column chromatography afterwards, and dress column silica gel is 180 mesh, the weight of used silica gel is 8 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 mixed organic solvents gradient elution, after each gradient elution to TLC contact plates is without point, replaces next gradient and wash It is de-；The gradient eluent of each gradient and concentration are collected, is monitored through TLC, merges identical part；
E, high performance liquid chromatography separation：Volume ratio will be used as 7:3 chloroform-acetone mixed organic solvents afford Part is purified using high performance liquid chromatography separation to get the hydroxypropyl isoflavone compound；
The high performance liquid chromatography separation purifying is using the methanol aqueous solution that volumetric concentration is 54% as 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 detects Wavelength is 338nm, each 80 μ L of sample introduction, collects the chromatographic peak of 30.2min, is evaporated after repeatedly adding up.
Wherein, the solvent of the step A is the ethanol water that volumetric concentration is 90%.The organic solvent of the step B For ethyl acetate.
Embodiment 4
Pawpaw sample is adopted in enshi.
A kind of preparation method of hydroxypropyl isoflavone compound using pawpaw as raw material, is extracted, organic solvent extraction through medicinal extract Take, MCI decolorations, silica gel column chromatography and high performance liquid chromatography preparative separation step are made, specifically include following steps：
A, medicinal extract extracts：Fresh pawpaw is crushed to 20~40 mesh, is extracted 2~5 times with solvent supersonic, every time extraction used The quality of solvent is 4 times of pawpaw quality, and each extraction time is 30~60 minutes, merges extracting solution and filters, filtrate decompression It is concentrated into be observed visually and just has Precipitation, stand 50 minutes, filter out sediment, gained filtrate decompression is condensed into leaching afterwards Cream a；
B, organic solvent extracts：The water that weight is 1.6 times of medicinal extract a weight is added in into medicinal extract a, is then extracted with organic solvent It takes 3~5 times, the volume of organic solvent used is identical with water volume every time, merges organic solvent extraction phase, will merge afterwards To organic solvent extraction phase be concentrated under reduced pressure into medicinal extract b；
C, MCI decolourizes：It is that the volumetric concentration of 4.5 times of medicinal extract b weight is 80% methanol aqueous solution to be added in into medicinal extract b, After medicinal extract b is completely dissolved, upper MCI columns are eluted for 94% methanol aqueous solution with volumetric concentration, merge eluent, afterwards Eluent after merging is concentrated under reduced pressure into medicinal extract c；
D, silica gel column chromatography：Medicinal extract c is first the acetone or first of 2.5 times of medicinal extract c with weight before through silica gel column chromatography Alcohol dissolves, and is then the 80 mesh silica gel mixed samples of 0.9 times of medicinal extract c with weight, and loading will carry out silica gel column chromatography afterwards, fills column silicon Glue is 180 mesh, and the weight of used silica gel is 6~10 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 mixed organic solvents gradient elution after each gradient elution to TLC contact plates is without point, is replaced next Gradient elution；The gradient eluent of each gradient and concentration are collected, is monitored through TLC, merges identical part；
E, high performance liquid chromatography separation：Volume ratio will be used as 7:3 chloroform-acetone mixed organic solvents afford Part is purified using high performance liquid chromatography separation to get the hydroxypropyl isoflavone compound；
The high performance liquid chromatography separation purifying is using the methanol aqueous solution that volumetric concentration is 54% as 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 detects Wavelength is 338nm, each 100 μ L of sample introduction, collects the chromatographic peak of 30.2min, is evaporated after repeatedly adding up.
Wherein, the solvent of the step A is ethyl alcohol.The organic solvent of the step B is ether.
Embodiment 5
Pawpaw sample is adopted in enshi.
A kind of preparation method of hydroxypropyl isoflavone compound using pawpaw as raw material, is extracted, organic solvent extraction through medicinal extract Take, MCI decolorations, silica gel column chromatography and high performance liquid chromatography preparative separation step are made, specifically include following steps：
A, medicinal extract extracts：Fresh pawpaw is crushed to 20~40 mesh, is extracted 2~5 times with solvent supersonic, every time extraction used The quality of solvent is 3 times of pawpaw quality, and each extraction time is 55 minutes, merges extracting solution and filters, filtrate decompression concentration Just there is Precipitation to being observed visually, stand 50 minutes, filter out sediment, gained filtrate decompression is condensed into medicinal extract a afterwards；
B, organic solvent extracts：The water that weight is 1.8 times of medicinal extract a weight is added in into medicinal extract a, is then extracted with organic solvent It takes 3 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 decolourizes：It is that the volumetric concentration of 4.2 times of medicinal extract b weight is 80% methanol aqueous solution to be added in into medicinal extract b, After medicinal extract b is completely dissolved, upper MCI columns are eluted for 90%~95% methanol aqueous solution with volumetric concentration, merge elution Eluent after merging is concentrated under reduced pressure into medicinal extract c by liquid afterwards；
D, silica gel column chromatography：Medicinal extract c is first the acetone or first of 2.5 times of medicinal extract c with weight before through silica gel column chromatography Alcohol dissolves, and is then the 90 mesh silica gel mixed samples of 1.1 times of medicinal extract c with weight, and loading will carry out silica gel column chromatography afterwards, fills column silicon Glue is 200 mesh, and the weight of used silica gel is 9 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 Hes 1:1 chloroform and acetone mixed organic solvents gradient elution, after each gradient elution to TLC contact plates is without point, replaces next gradient Elution；The gradient eluent of each gradient and concentration are collected, is monitored through TLC, merges identical part；
E, high performance liquid chromatography separation：Volume ratio will be used as 7:3 chloroform-acetone mixed organic solvents afford Part is purified using high performance liquid chromatography separation to get the hydroxypropyl isoflavone compound；
The high performance liquid chromatography separation purifying is using the methanol aqueous solution that volumetric concentration is 54% as 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 detects Wavelength is 338nm, each 10 μ L of sample introduction, collects the chromatographic peak of 30.2min, is evaporated after repeatedly adding up.
Wherein, the solvent of the step A is methanol.The organic solvent of the step B is petroleum ether.
Embodiment 6
Pawpaw sample is adopted in enshi.
A kind of preparation method of hydroxypropyl isoflavone compound using pawpaw as raw material, is extracted, organic solvent extraction through medicinal extract Take, MCI decolorations, silica gel column chromatography and high performance liquid chromatography preparative separation step are made, specifically include following steps：
A, medicinal extract extracts：The fresh pawpaw of 4.9kg is crushed to 30 mesh solvent supersonics to extract 4 times, every time extraction used The quality of solvent is 5 times of pawpaw quality, and each extraction time is 60 minutes, merges extracting solution and filters, filtrate decompression concentration Just there is Precipitation to being observed visually, stand 20~60 minutes, filter out sediment, gained filtrate decompression is condensed into leaching afterwards Cream a, weight 150g；
B, organic solvent extracts：The water of 250g is added in into medicinal extract a, is then extracted 5 times with organic solvent, it is used every time to have The volume of solvent is identical with water volume, merges organic solvent extraction phase, will merge obtained organic solvent extraction phase afterwards It is concentrated under reduced pressure into medicinal extract b, weight 63.8g；
C, MCI decolourizes：The volumetric concentration that 240g is added in into medicinal extract b is 80% methanol aqueous solution, treats that medicinal extract b is completely molten Xie Hou, upper MCI columns are eluted for 90% methanol aqueous solution 5L with volumetric concentration, merge eluent, afterwards by washing after merging De- liquid is concentrated under reduced pressure into medicinal extract c, weight 38.2g；
D, silica gel column chromatography：For medicinal extract c before through silica gel column chromatography, then the acetone solution for being first 85g with weight uses weight For 1.1 times of 90 mesh silica gel mixed samples of medicinal extract c, loading will carry out silica gel column chromatography afterwards, and dress column silica gel is 200 mesh, used silica gel Weight be 8 times of medicinal extract c weight amount；20 are followed successively by with volume ratio:1、9:1、8:2、7:3、6:4 and 1:1 chloroform and acetone mixes Organic solvent gradient elution is closed, after each gradient elution to TLC contact plates is without point, replaces next gradient elution；Collect each gradient Gradient eluent simultaneously concentrates, and is monitored through TLC, merges identical part；
E, high performance liquid chromatography separation：Volume ratio will be used as 7:3 chloroform-acetone mixed organic solvents afford Partly (13.6g) is purified using high performance liquid chromatography separation to get the hydroxypropyl isoflavone compound；
The high performance liquid chromatography separation purifying is using the methanol aqueous solution that volumetric concentration is 54% as 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 detects Wavelength is 338nm, each 50 μ L of sample introduction, collects the chromatographic peak of 30.2min, is evaporated 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 ethyl acetate.
Embodiment 7
Pawpaw sample is adopted in Dali.
A kind of preparation method of hydroxypropyl isoflavone compound using pawpaw as raw material, is extracted, organic solvent extraction through medicinal extract Take, MCI decolorations, silica gel column chromatography and high performance liquid chromatography preparative separation step are made, specifically include following steps：
A, medicinal extract extracts：The fresh pawpaws of 10kg are crushed to 40 mesh, are extracted 4 times with solvent supersonic, extraction used is molten every time The quality of agent is 5 times of pawpaw quality, and each extraction time is 50 minutes, merges extracting solution and filters, filtrate decompression is concentrated into Being observed visually just has Precipitation, stands 20~60 minutes, filters out sediment, gained filtrate decompression is condensed into medicinal extract afterwards A, weight 980g；
B, organic solvent extracts：The water of 1.5kg is added in into medicinal extract a, is then extracted 5 times with organic solvent, it is used every time The volume of organic solvent is identical with water volume, merges organic solvent extraction phase, will merge obtained organic solvent extraction afterwards Mutually decompression is condensed into medicinal extract b, weight 460g；
C, MCI decolourizes：It is that the volumetric concentration of 600g is 80% methanol aqueous solution to be added in into medicinal extract b, treats that medicinal extract b is complete After dissolving, upper MCI columns are eluted for 90% methanol aqueous solution 10L with volumetric concentration, merge eluent, after merging afterwards Eluent be concentrated under reduced pressure into medicinal extract c, weight 280g；
D, silica gel column chromatography：Medicinal extract c is then medicinal extract c with weight first with the acetone of 450g before through silica gel column chromatography 1.1 times of 100 mesh silica gel mixed samples, afterwards loading will carry out silica gel column chromatography, dress column silica gel is 200 mesh, the weight of used silica gel For 2.0kg；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-, after each gradient elution to TLC contact plates is without point, replace next gradient elution；The gradient eluent of each gradient and concentration are collected, It is monitored through TLC, merges identical part；
E, high performance liquid chromatography separation：Volume ratio will be used as 7:3 chloroform-acetone mixed organic solvents afford Partly (42.5g) is purified using high performance liquid chromatography separation to get the hydroxypropyl isoflavone compound；
The high performance liquid chromatography separation purifying is using the methanol aqueous solution that volumetric concentration is 54% as 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 detects Wavelength is 338nm, each 80 μ L of sample introduction, collects the chromatographic peak of 30.2min, is evaporated after repeatedly adding up.
Wherein, the solvent of the step A is the methanol aqueous solution that volumetric concentration is 80%.The organic solvent of the step B For ethyl acetate.
Embodiment 8
The structure for the isoflavone compound that embodiment 1 is prepared is measured by the following method：
The compound is light yellow gum object；
HRESI-MS shows that its quasi-molecular ion peak is 349.1046 [M+Na]+(calculated value 349.1052), with reference to1H NMR It is composed with DEPT and determines that its molecular formula is C19H18O5, degree of unsaturation 11.
Hydroxyl (3416), carbonyl (1655) and aromatic ring (1614,1563 and 1480cm are shown in infrared spectrum-1) resonance Absworption peak.And ultraviolet spectra has absorption maximum to also illustrate that there may be aromatic ring structures in compound in 210,260,338nm.
Compound1H and13C H NMR spectroscopies data (such as table 1, Fig. 1 and Fig. 2) show that it contains 19 carbon and 18 hydrogen, including 11,2,4,5- quaternary phenyl ring (C-5~C-10, H-5, H-8), 1 Isosorbide-5-Nitrae-disubstituted phenyl ring (C-1'~C-6', H- 2', 6' and H-3', 5'), 1 α, beta-unsaturated carbonyl (C-2, C-3, C-4, H-3), 1 3- hydroxypropyl (C-1 "~C-3 ", H2- 1 "~H2- 3 "), 1 methoxyl group (δC56.4q δH3.79s) and 1 phenolic hydroxyl group (δH10.76s).According to typical 2 A phenyl ring, α, beta-unsaturated carbonyl signal, it is isoflavone compound that can speculate the compound.
According to H-2 and C-3, C-4, C-9, C-1 ', H-5 and C-4, C-9, C-10, H-8 and C-6, C-7, C-9, C-10, with And H-2', 6 ' (such as Fig. 3) related to the HMBC of C-3 may further confirm that compound is osajin structure.The parent of compound After determining, remaining substituent group, 3 hydroxypropyls, methoxyl group and phenolic hydroxyl group can be considered the substituent group on flavones.
Methoxyl group hydrogen (δ can be observed in (such as Fig. 3) in the HMBC spectrums of compoundH3.79) with C-4'(δC160.3) HMBC Correlation can speculate the methoxy substitution at C-4'；According to H2-1”(δH2.72) with C-6 (δC 150.2)、C-7(δC And C-8 (δ 130.3)C116.7), H2-2”(δH1.87) with C-7 (δCAnd H-8 (δ 130.3)HAnd C-1 " (δ 6.70)C 28.9) HMBC is related, it can be verified that 3- hydroxypropyls are substituted in C-7.Phenolic hydroxyl group is substituted in C-6 can be by phenolic hydroxyl group hydrogen (δH And C-5 (δ 10.76)C 114.1)、C-6(δ CAnd C-7 (δ 150.2)C130.3) HMBC correlations are confirmed.In addition it is typical Phenyl ring on proton signal [H-5, δH7.07s；H-8,δH6.70s；H-2 ', 6 ', δH7.72(d)8.8；H-3 ', 5 ', δH 6.79 (d) 8.8] also susceptible of proof compound A rings be 6,7- positions two substitute, B rings for 4'- it is monosubstituted.
So far, the structure of compound is determined, and is named as：6- hydroxyls -7- (3- hydroxypropyls) -4 '-methoxyl group-different Huang Ketone.
Embodiment 9
Embodiment 8 is repeated, there is following difference：Compound prepared by Example 2-7 is measured, and is light yellow gum Object confirms that compound prepared by embodiment 2-7 is identical isoflavone compound --- 6- hydroxyls -7- (3- hydroxypropyls) -4 ' - Methoxy-isofiavone.
Embodiment 10
The hydroxypropyl isoflavone compound of any preparation in Example 1-7 carries out the additive effect examination of cigarette filter It tests, test situation is as follows：
For the cigarette " purple cloud " that addition cigarette is Hong Yun Red River group, with triacetyl glycerine by the different Huang of above-mentioned hydroxypropyl The ketone compounds solution for being made into 0.1mg/mL.It is uniformly sprayed onto on filter tow, is made by the 8% of filter tow weight Then the filter stick is made cigarette by conventional cigarette cigarette, carries out sensory evaluation by filter stick, and to be not added with the compound Identical cigarette is as control.Evaluation and analysis the result shows that：It compares with control, the sweet sense of cigarette smoking has the promotion, the effect of promoting the production of body fluid bright Aobvious, irritation is reduced, suction comfort be improved significantly.
Embodiment 11
The hydroxypropyl isoflavone compound of any preparation in Example 1-7 carries out the additive effect examination of cigarette filter It tests,
For the cigarette " Camellia is soft " that addition cigarette is Hong Yun Red River group, with triacetyl glycerine by above-mentioned hydroxypropyl The isoflavone compound solution for being made into 0.2mg/mL.It is uniformly sprayed onto by the 5% of filter tow weight on filter tow, Filter stick is made, cigarette then is made by conventional cigarette cigarette in the filter stick, carries out sensory evaluation, and to be not added with the chemical combination The identical cigarette of object is as control.Evaluation and analysis the result shows that：It compares with control, the sweet sense of cigarette smoking has promotion, promote the production of body fluid work With apparent, irritation is reduced, suction comfort be improved significantly.
Basic principle, main feature 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 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 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 (8)

  1. A kind of 1. hydroxypropyl isoflavone compound, which is characterized in that structural formula such as formula（I）It is shown：
    , formula（I）.
  2. 2. the preparation method of hydroxypropyl isoflavone compound described in claim 1, which is characterized in that using pawpaw as raw material, Extracted through medicinal extract, organic solvent extraction, MCI decolorations, silica gel column chromatography and high performance liquid chromatography preparative separation step are made, specifically Comprise the following steps：
    A, medicinal extract extracts：Fresh pawpaw is crushed to 20 ~ 40 mesh, is extracted 2 ~ 5 times with solvent supersonic, each Extraction solvent used Quality is 3-6 times of pawpaw quality, and each extraction time is 30 ~ 60 minutes, merges extracting solution and filters, filtrate decompression is concentrated into Being observed visually just has Precipitation, stands 20 ~ 60 minutes, filters out sediment, gained filtrate decompression is condensed into medicinal extract afterwards a；
    B, organic solvent extracts：Into medicinal extract a add in 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 decolourizes：It is that the volumetric concentration of 3 ~ 5 times of medicinal extract b weight is 80% methanol aqueous solution to be added in into medicinal extract b, treats medicinal extract After b is completely dissolved, upper MCI columns are eluted for 90% ~ 95% methanol aqueous solution with volumetric concentration, merge eluent, will be closed afterwards Eluent after and is concentrated under reduced pressure into medicinal extract c；
    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 amounts of c weight；Using volume ratio as 1:0~0:1 chloroform and acetone mixed organic solvents gradient elution, each gradient elution To TLC contact plates without point after, replace next gradient elution；The gradient eluent of each gradient and concentration are collected, is monitored through TLC, is merged Identical part；
    E, high performance liquid chromatography separation：Volume ratio will be used as 7:The part that 3 chloroform-acetone mixed organic solvents afford It is purified using high performance liquid chromatography separation to get the hydroxypropyl isoflavone compound.
  3. 3. the preparation method of hydroxypropyl isoflavone compound according to claim 2, which is characterized in that the step A Solvent be volumetric concentration be 70 ~ 100% aqueous acetone solution, volumetric concentration be 90 ~ 100% ethanol water or volumetric concentration For 90 ~ 100% methanol aqueous solution.
  4. 4. the preparation method of hydroxypropyl isoflavone compound according to claim 2, which is characterized in that the step B Organic solvent be dichloromethane, chloroform, ethyl acetate, ether or petroleum ether.
  5. 5. the preparation method of hydroxypropyl isoflavone compound according to claim 2, which is characterized in that the D steps Middle medicinal extract c is first that the acetone of 1.5 ~ 3 times of medicinal extract c or methanol dissolve with weight, then uses weight before through silica gel column chromatography It is 80 ~ 100 mesh silica gel mixed samples of 0.8 ~ 1.2 times of medicinal extract c, loading afterwards.
  6. 6. the preparation method of hydroxypropyl isoflavone compound according to claim 2, which is characterized in that the D steps In, 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 to TLC contact plates without point after, replace next gradient elution.
  7. 7. the preparation method of hydroxypropyl isoflavone compound according to claim 2, which is characterized in that the E steps High performance liquid chromatography separation purifying be the flow velocity 20ml/min using the methanol aqueous solution that volumetric concentration is 54% as mobile phase, with 21.2 ' 250 mm, 5mThe Zorbax PrepHT GF reverse phase preparative columns of m are stationary phase, and UV detector Detection wavelength is 338nm, each 10 ~ 100mL of sample introduction collect the chromatographic peak of 30.2min, are evaporated after repeatedly adding up.
  8. 8. hydroxypropyl isoflavone compound described in claim 1 is as the application for preparing cigarette filter-tip additive agent.
CN201711354150.2A 2017-12-15 2017-12-15 A kind of hydroxypropyl isoflavone compound and preparation method and application Pending CN108084137A (en)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102977065A (en) * 2012-12-06 2013-03-20 云南烟草科学研究院 Flavonoid compound and preparation method and application thereof
CN107759554A (en) * 2017-10-18 2018-03-06 云南中烟工业有限责任公司 A kind of hydroxypropyl isoflavonoid and its preparation method and application

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102977065A (en) * 2012-12-06 2013-03-20 云南烟草科学研究院 Flavonoid compound and preparation method and application thereof
CN107759554A (en) * 2017-10-18 2018-03-06 云南中烟工业有限责任公司 A kind of hydroxypropyl isoflavonoid and its preparation method and application

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