CN107400107A - A kind of flavone compound in rose waste residue and preparation method and application - Google Patents
A kind of flavone compound in rose waste residue and preparation method and application Download PDFInfo
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- CN107400107A CN107400107A CN201710620512.1A CN201710620512A CN107400107A CN 107400107 A CN107400107 A CN 107400107A CN 201710620512 A CN201710620512 A CN 201710620512A CN 107400107 A CN107400107 A CN 107400107A
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- medicinal extract
- waste residue
- flavone compound
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- organic solvent
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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
- C07D311/28—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 2 only
- C07D311/30—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 2 only not hydrogenated in the hetero ring, e.g. flavones
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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
-
- 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 flavone compound in a kind of rose waste residue and preparation method and application, belong to technical field of phytochemistry.The flavone compound is isolated from the waste residue after way of distillation production Rosa Damascana, and Compound nomenclature is：5 hydroxyl 2', the methyl flavones of 7 dimethoxy 6, its molecular formula are C18H16O5, its structural formula such as formula（I）It is shown：, formula（I）；Preparation method is to produce the waste residue after Rosa Damascana as raw material, is extracted through medicinal extract, organic solvent extraction, MCI decolourizes, silica gel column chromatography and high performance liquid chromatography separation step are made.The compounds of this invention is added in cigarette filter, can coordinate this perfume with tobacco, increase the sweet sense of flue gas, and alleviating the throat after smoking stimulates, and has the obvious pharynx-clearing throat-benefiting effect of energy, and can improve the suction quality of cigarette.
Description
Technical field
The invention belongs to technical field of phytochemistry, is related to the flavone compound in a kind of rose waste residue and its preparation side
Method and application, and in particular to extract obtained flavone compound in the waste residue after a kind of Rosa Damascana from production first.The change
Compound is added in cigarette filter, can coordinate this perfume with tobacco, and alleviating the throat after smoking stimulates, and has obvious clearing profit
Larynx effect, and the suction quality of cigarette can be improved.
Background technology
Damask Rose（Scientific nameRosa Damascena, common first names Damask rose）, also known as Tujue rose, rose
Section's Rosa, belong to classic garden rose, bush plant, originate in Syria, started in 14th century widely to plant in France, greatly
Ma Shige roses are the main rose varieties of Bulgaria's plantation, open hose-in-hose, petal edge color is slightly shallow, has as silks and satins
Texture；Purely, the careful fragrance of a flower makes its hat pressure beautiful and fragrant flowers, turns into the top grade in rose for oil, thus is widely cultivated to extract
Rosa Damascana.Rosa Damascana is the essential oil of most expensive in the world, is referred to as " after essential oil ".Except being widely used in food and cosmetic
Outside product, Rosa Damascana is also widely used in perfuming cigarette；There is cigarette after addition Rosa Damascana tobacco to add answering for Rose Essentielle
Blending type feature, jealous abundant sweetness, smoke is pure and fresh light refreshing, and unique enjoyment of graceful fragrance can be brought to consumer.
Rosa Damascana is usually using the fresh rose flower plucked in the morning as raw material, passes through distillation or the method for supercritical extract
Prepare, the yield of Rosa Damascana is extremely low, and the flower of about five tons of weights can only extract two pounds of attar of rose.It is useless after essential oil generation
A large amount of chemical compositions with value of exploiting and utilizing are also rich in slag, such as：Quercitrin, amaroid, tannin, fat oil, organic acid
（Gallic acid）, haematochrome, uranidin, beta carotene etc..Rose waste residue after production essential oil is comprehensively utilized, to comprehensive
Conjunction utilizes resource, and the added value for improving rose processing has important practical significance.
Research shows, outside the routine chemical componentses such as isolating protein, amino acid, sugar, phosphorus, calcium, potassium, after producing Rosa Damascana
Also contain a large amount of secondary metabolites in waste residue, type of compounds include flavones, cumarin, tannin, furans, flavones, Phenylpropanoid Glycosides,
Terpene, alkaloid etc..These compounds have multiple biological activities, in antibacterial, anti-inflammatory, anti-mutation, decompression, clearing heat and detoxicating, town
Quiet, diuresis, anti-oxidant, anticancer, anti-cancer, suppression lipase etc. many aspects have remarkable result.
Flavone compound refers to two phenyl ring with phenolic hydroxyl group（A- and B- rings）Mutually interconnected by central thricarbon atom
A series of compounds formed are tied, its basic parent nucleus is 2- phenyl chromones.Phenol hydroxyl is often connected with flavone compound structure
The functional groups such as base, methoxyl group, methyl, isopentene group.In addition, it is also often combined into glycosides with sugar.The effect of flavones be it is many,
It is a kind of very strong antioxidant, and the ability for preventing oxidation is more than ten times of vitamin E, and this antioxidation can prevent
Degeneration, the aging of cell, can also prevent the generation of cancer.Flavones can improve blood circulation, reduce cholesterol, improve heart and brain blood
Pipe disease.In addition, flavone compound also has prominent improvement sense of taste effect, the Gustatory Representation of some flavone compounds is very
Especially, there is a kind of natural sweet taste after entrance.Flavones contained by olive is exactly that it can be returned the main reason for sweet, and flavones content
It is higher, return it is sweet more obvious, smell is more mellow.A kind of present invention isolated flavonoids from production Rosa Damascana waste residue
Compound, the compound are added in cigarette filter, can dramatically increase the sweet sense of flue gas, and alleviating the throat after smoking stimulates,
The effect of with the suction quality for improving cigarette.
The content of the invention
The first object of the present invention is in the flavone compound in a kind of rose waste residue is provided；Second purpose is to provide
The preparation method of the flavone compound；3rd purpose is in providing the flavone compound in cigarette filter perfuming
Using for increasing the sweet sense of flue gas, alleviating the throat after smoking stimulates, and improves cigarette smoking quality.
To achieve the above object, the technical solution adopted by the present invention is as follows：
The flavone compound that the first object of the present invention is achieved in that in a kind of rose waste residue is from production Rosa Damascana
It is isolated in waste residue afterwards, it is named as：5- hydroxyls -2', 7- dimethoxy -6- methyl-flavones, English are entitled：5-
Hydroxy-2', 7-dimethoxy-6-methyl-flavone, its molecular formula are C18H16O5, its structural formula such as formula（I）It is shown：
, formula（I）.
The compound is light yellow gum thing, is named as：Compound nomenclature is：5- hydroxyls -2', 7- dimethoxy -6- methyl-Huang
Ketone, English are entitled：5-hydroxy-2',7-dimethoxy-6-methyl-flavone.
The second object of the present invention is achieved in that the preparation method of the flavone compound, is to produce rose
Waste residue after essential oil is raw material, is extracted through medicinal extract, organic solvent extracts, MCI decolourizes, silica gel column chromatography and high performance liquid chromatography divide
It is made from step, is specially：
A, medicinal extract extracts：Waste residue powder after production Rosa Damascana is extracted 2 ~ 5 times with solvent supersonic, each Extraction solvent used
Quality is 2 ~ 6 times of waste residue powder quality, and each extraction time is 30 ~ 60 minutes, merges extract solution and filters, filtrate decompression concentration
To just there is sediment precipitation, 20 ~ 60 minutes are stood, sediment is filtered out, gained filtrate decompression is condensed into medicinal extract a afterwards；
B, organic solvent extracts：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 decolourizes：Into medicinal extract b, addition is that the volumetric concentration of 3 ~ 5 times of medicinal extract b weight is 95% methanol aqueous solution, treats medicinal extract b
After being completely dissolved, upper MCI posts, it is that 90% ~ 95% methanol aqueous solution is eluted with volumetric concentration, merges eluent, will close 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 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, each gradient elution
To TLC point plates without point after, change 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 6:The part that 4 chloroform-acetone mixed organic solvents afford
Purified using high performance liquid chromatography separation, produce described flavone 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 are dense
The ethanol water or volumetric concentration spent for 90 ~ 100% are 90 ~ 100% methanol aqueous solution.
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 in the D steps medicinal extract c before through silica gel column chromatography, first with weight be medicinal extract c 1.5 ~
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 to TLC point plates without point after, replacing is next
Gradient elution.
It is further preferred that the E steps high performance liquid chromatography separation purifying be using volumetric concentration as 40% first
Alcohol solution is mobile phase, 15 ~ 25ml/min of flow velocity, with 21.2 × 250mm, 5 μm of the anti-phase preparations of Zorbax PrepHT GF
Post is stationary phase, and UV-detector Detection wavelength is 365nm, each μ L of sample introduction 50 ~ 200, collects 39.6min chromatographic peak, more
It is secondary it is cumulative after be evaporated.
The present invention is unrestricted to the granularity of waste residue powder.
Flavone compound of the present invention can increase the sweet sense of cigarette smoke, and alleviating the throat after smoking stimulates, and has
Pharynx-clearing throat-benefiting effect.
The structure for the flavone compound that method described above is prepared is measured by the following method：
The compounds of this invention is light yellow gum thing；HRESI-MS shows that its quasi-molecular ion peak is 335.0886 [M+Na]+
(calculated value 335.0895), with reference to1H NMR and DEPT spectrum determine that its molecular formula is C18H16O5, degree of unsaturation 11.
Hydroxyl (3428), carbonyl (1665) and aromatic ring (1618,1459 and 1410cm are shown in infrared spectrum-1) resonance
Absworption peak.And ultraviolet spectra there may be aromatic ring structure in 210,262,365nm have absorption maximum to also illustrate that compound.
Compound1H and13C H NMR spectroscopies（Such as table 1, Fig. 1 and Fig. 2）Show that it contains 17 carbon and 14 hydrogen, including 1
The phenyl ring (C-5 ~ C-10, H-8) of 1,2,3,4,5- five substitution, 1 the dibasic phenyl ring of 1,2- (C-1' ~ C-6', H-3' ~ H-
6'), 1 α, beta-unsaturated carbonyl (C-4), 1 group of double bond (C-2 and C-3, H-3), 1 methyl (d C 7.91 q,d H2.49 s),
Two methoxyl groups (d C56.4 q and 55.9 q,d H3.82 s and 3.85 s), and 1 phenolic hydroxyl group (d H13.93 s).Root
According to typical 2 phenyl ring, α, beta-unsaturated carbonyl and double bond signal, it is flavone compound that can speculate compound.According to H-3 and
C-1', and H-6' are related to C-2 HMBC（Such as Fig. 3）May further confirm that compound is flavonoid structure.
After the parent of compound determines, remaining substituent, methyl, methoxyl group and phenolic hydroxyl group can be considered the substitution on flavones
Base.In the HMBC spectrums of compound（Such as Fig. 3）Can be observed two methoxyl group hydrogen (d H3.85) and C-2'(3.82 andd C
156.3) and C-7 (d C 165.9) HMBC is related, can speculate that two methoxyl groups are substituted in C-2' and C-7 positions respectively；According to methyl
Hydrogen (d H2.48) it is related to C-5, C-6, C-7 HMBC, it can be verified that methyl is substituted in C-6 positions；According to phenolic hydroxyl group hydrogen (d H
13.93) it is related to C-10 HMBC to C-5, C-6, it can be verified that the phenolic hydroxyl group is substituted in C-5 positions respectively.Other typical phenyl ring
Upper proton signal (H-8,d H6.82 s；H-3 ',d H7. 13(d) 7.6；H-4 ',d H7.32 (t) 7.6；H-5 ',d H
6.88 (t) 7.6；H-6 ',d H7.91 (d) 7.6) also the B rings of susceptible of proof chromocor compound of the present invention are that 5,6,7- positions three take
Generation, C rings are that 2'- positions are monosubstituted.
So far, the structure of compound is determined, and is named as Compound nomenclature and is：5- hydroxyls -2', 7- dimethoxy -
6- methyl-flavones.
Infrared, the ultraviolet and mass spectrometric data of compound：UV (methanol),λ max (log ε) 210 (4.73)、262
(4.35)、365 (3.82)nm；IR (pressing potassium bromide troche)：ν max 3428、1665、1618、1459、1410、1362、1172、
1038、846、785 cm-1；1H and13C NMR data (400 and 100 MHz, (C5D5N), it is shown in Table -1；Positive ion mode
ESIMS m/z 335 [M+Na]+；Positive ion mode HRESIMSm/z 335.0886 [M+Na]+(calculated value C18H16NaO5,
335.0895)。
The compounds of this invention of table 1.1H NMR and13C NMR data (C5D5N)
What the third object of the present invention was realized in：
Flavone compound in described rose waste residue is as the application for preparing cigarette filter-tip additive agent.
The present invention considers that triacetyl glycerine is that cigarette filter is molded the most frequently used plasticizer, and the compounds of this invention
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.
For cigarette that addition cigarette is Hongta Group " Hongta is classical ", with triacetyl glycerine by above-mentioned flavones chemical combination
The thing solution for being made into 0.5mg/mL.Uniformly it is sprayed onto by the 5-8% of filter tow weight on filter tow, filter stick is made, so
Cigarette is made by the cigarette cigarette of routine in the filter stick afterwards, carries out sensory evaluation, and to be not added with the same volume of the compound
Cigarette is as control.Evaluation and analysis result shows：Compared with control, the compounds of this invention is added in cigarette filter, increases flue gas
Sweet sense, alleviating the throat after smoking stimulates, and can be obviously improved the suction quality of cigarette.
Compared with prior art, its advantage is the present invention：
The compounds of this invention is isolated in the waste residue after Rosa Damascana to produce, and raw material sources are very extensive, and cost is low；It is raw
Waste resource can be comprehensively utilized by producing the compound, and the added value for improving rose processing is had important practical significance.
The compounds of this invention is simple in construction, can also be produced by artificial synthesized, be easier to realize, carried for tobacco industry
For new additive., can be sweet by three acetic acid in cigarette filter forming process and the compounds of this invention is dissolved in triacetyl glycerine
Grease is added in filter tip, does not increase extra process, and the application in cigarette is easily realized.
Compared with control, the compounds of this invention is added in cigarette filter, increases the sweet sense of flue gas, after alleviating smoking
Throat stimulate, there is obvious pharynx-clearing throat-benefiting effect, improve the effect of cigarette smoking quality clearly.
Brief description of the drawings
The carbon-13 nmr spectra of Fig. 1 flavone compounds of the present invention（13C NMR）；
Fig. 2 is the proton nmr spectra of flavone compound of the present invention（1H NMR）；
The related figures of the crucial HMBC of Fig. 3 flavone compounds 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.Material therefor or the unreceipted production firm person of equipment, it is that can be obtained by buying
Conventional products.
Flavone compound in rose waste residue of the present invention is separated from the waste residue after production Rosa Damascana
Arrive, be named as：5- hydroxyls -2', 7- dimethoxy -6- methyl-flavones, English are entitled：5-hydroxy-2',7-dimethoxy-
6-methyl-flavone, its molecular formula are C18H16O5, its structural formula such as formula（I）It is shown：
, formula（I）.
The compound is light yellow gum thing, is named as：Compound nomenclature is：5- hydroxyls -2', 7- dimethoxy -6- methyl-Huang
Ketone, English are entitled：5-hydroxy-2',7-dimethoxy-6-methyl-flavone.
The preparation method of flavone compound of the present invention, it is to produce the waste residue after Rosa Damascana as raw material, through leaching
Cream extraction, organic solvent extraction, MCI decolourizes, silica gel column chromatography and high performance liquid chromatography separation step are made, and is specially：
A, medicinal extract extracts：Waste residue powder after production Rosa Damascana is extracted 2 ~ 5 times with solvent supersonic, each Extraction solvent used
Quality is 2 ~ 6 times of waste residue powder quality, and each extraction time is 30 ~ 60 minutes, merges extract solution and filters, filtrate decompression concentration
To just there is sediment precipitation, 20 ~ 60 minutes are stood, sediment is filtered out, gained filtrate decompression is condensed into medicinal extract a afterwards；
B, organic solvent extracts：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 decolourizes：Into medicinal extract b, addition is that the volumetric concentration of 3 ~ 5 times of medicinal extract b weight is 95% methanol aqueous solution, treats medicinal extract b
After being completely dissolved, upper MCI posts, it is that 90% ~ 95% methanol aqueous solution is eluted with volumetric concentration, merges eluent, will close 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 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, each gradient elution
To TLC point plates without point after, change 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 6:The part that 4 chloroform-acetone mixed organic solvents afford
Purified using high performance liquid chromatography separation, produce described flavone compound.
The solvent of the step A be volumetric concentration be 70 ~ 100% aqueous acetone solution, volumetric concentration be 90 ~ 100% second
Alcohol solution or the methanol aqueous solution that volumetric concentration is 90 ~ 100%.
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 to TLC point plates without point after, change next gradient elution.
The E steps high performance liquid chromatography separation purifying be using the methanol aqueous solution that volumetric concentration is 40% as mobile 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 inspection
It is 365nm to survey device Detection wavelength, each μ L of sample introduction 50 ~ 200, collects 39.6min 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, it can coordinate this perfume with tobacco, increase the sweet sense of flue gas, alleviating the throat after smoking stimulates, tool
There is obvious pharynx-clearing throat-benefiting effect, and the suction quality of cigarette can be improved.
Embodiment 1
The waste residue sample source after Rosa Damascana is produced in Yunnan Yuxi, kind is Damask Rose.
A, medicinal extract extracts：Waste residue powder after production Rosa Damascana is extracted 2 times with solvent supersonic, every time Extraction solvent used
Quality be 2 times of waste residue powder quality, each extraction time is 30 minutes, merges extract solution and simultaneously filters, filtrate decompression is concentrated into
Just there is sediment precipitation, stand 20 minutes, filter 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 into medicinal extract a, is then extracted 3 times with organic solvent,
The volume of organic solvent used is identical with water volume every time, merges organic solvent extraction phase, will merge afterwards obtain it is organic
Solvent extraction, which is mutually depressurized, is condensed into medicinal extract b；
C, MCI decolourizes：Into medicinal extract b, addition is that the volumetric concentration of 3 times of medicinal extract b weight is 95% methanol aqueous solution, treats that medicinal extract b is complete
After fully dissolved, upper MCI posts, it is that 90% methanol aqueous solution is eluted with volumetric concentration, merges eluent, afterwards by after merging
Eluent is concentrated under reduced pressure into medicinal extract c；
D, silica gel column chromatography：Medicinal extract c is first that 1.5 times of medicinal extract c acetone or methanol dissolve with weight, is then leaching with weight
0.8 times of cream c 80 mesh silica gel mixed samples, the column chromatography of loading progress afterwards, dress post silica gel are 160 mesh, and the weight of used silica gel is leaching
6 times of amounts of cream c weight；Using volume ratio as 20:1、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 point plates is without point, changes next gradient elution；Collect the gradient eluent of each gradient and dense
Contracting, is monitored through TLC, merges identical part；
E, high performance liquid chromatography separation：Volume ratio will be used as 6:The part that 4 chloroform-acetone mixed organic solvents afford
Purified using high performance liquid chromatography separation, the specific method of high performance liquid chromatography separation purifying is：Using volumetric concentration as 40% first
Alcohol solution is mobile phase, and flow velocity 15ml/min, with 21.2 × 250mm, 5 μm of Zorbax PrepHT GF reverse phase preparative columns are
Stationary phase, UV-detector Detection wavelength are 365nm, each μ L of sample introduction 50, collect 39.6min chromatographic peak, after repeatedly adding up
It is evaporated, produces described flavone compound.
Wherein, the solvent of step A is the aqueous acetone solution that volumetric concentration is 70%.The organic solvent of the step B is chlorine
It is imitative.
Embodiment 2
The waste residue sample source after Rosa Damascana is produced in Yunnan Yuxi, kind is Damask Rose.
A, medicinal extract extracts：Waste residue powder after production Rosa Damascana is extracted 5 times with solvent supersonic, every time Extraction solvent used
Quality be 6 times of waste residue powder quality, each extraction time is 60 minutes, merges extract solution and simultaneously filters, filtrate decompression is concentrated into
Just there is sediment precipitation, 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 into medicinal extract a, is then extracted 5 times with organic solvent,
The volume of organic solvent used is identical with water volume every time, merges organic solvent extraction phase, will merge afterwards obtain it is organic
Solvent extraction, which is mutually depressurized, is condensed into medicinal extract b；
C, MCI decolourizes：Into medicinal extract b, addition is that the volumetric concentration of 5 times of medicinal extract b weight is 95% methanol aqueous solution, treats that medicinal extract b is complete
After fully dissolved, upper MCI posts, it is that 95% methanol aqueous solution is eluted with volumetric concentration, merges eluent, afterwards by after merging
Eluent is concentrated under reduced pressure into medicinal extract c；
D, silica gel column chromatography：Medicinal extract c is first that 3 times of medicinal extract c acetone or methanol dissolve with weight, is then medicinal extract c with weight
1.2 times of 100 mesh silica gel mixed samples, the column chromatography of loading progress afterwards, dress post silica gel is 200 mesh, and the weight of used silica gel is medicinal extract c
10 times of amounts of weight；Using volume ratio as 20:1、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 point plates is without point, change next gradient elution；The gradient eluent of each gradient and concentration are collected,
Monitored through TLC, merge identical part；
E, high performance liquid chromatography separation：Volume ratio will be used as 6:The part that 4 chloroform-acetone mixed organic solvents afford
Purified using high performance liquid chromatography separation, the specific method of high performance liquid chromatography separation purifying is：Using volumetric concentration as 40% first
Alcohol solution is mobile phase, and flow velocity 25ml/min, with 21.2 × 250mm, 5 μm of Zorbax PrepHT GF reverse phase preparative columns are
Stationary phase, UV-detector Detection wavelength are 365nm, each μ L of sample introduction 200, collect 39.6min chromatographic peak, after repeatedly adding up
It is evaporated, produces described flavone compound.
Wherein, the solvent of step A is acetone.The organic solvent of the step B is dichloromethane.
Embodiment 3
The waste residue sample source after Rosa Damascana is produced in Yunnan Yuxi, kind is Damask Rose.
A, medicinal extract extracts：Waste residue powder after production Rosa Damascana is extracted 3 times with solvent supersonic, every time Extraction solvent used
Quality be 3 times of waste residue powder quality, each extraction time is 40 minutes, merges extract solution and simultaneously filters, filtrate decompression is concentrated into
Just there is sediment precipitation, stand 40 minutes, filter out sediment, gained filtrate decompression is condensed into medicinal extract a afterwards；
B, organic solvent extracts：The water that weight is 1.5 times of medicinal extract a weight is added into medicinal extract a, then extracts 4 with organic solvent
Secondary, the volume of organic solvent used is identical with water volume every time, merges organic solvent extraction phase, has afterwards by what merging obtained
Solvent extraction phase is concentrated under reduced pressure into medicinal extract b；
C, MCI decolourizes：Into medicinal extract b, addition is that the volumetric concentration of 4 times of medicinal extract b weight is 95% methanol aqueous solution, treats that medicinal extract b is complete
After fully dissolved, upper MCI posts, it is that 93% methanol aqueous solution is eluted with volumetric concentration, merges eluent, afterwards by after merging
Eluent is concentrated under reduced pressure into medicinal extract c；
D, silica gel column chromatography：Medicinal extract c is first that 2 times of medicinal extract c acetone or methanol dissolve with weight, is then medicinal extract c with weight
1 times of 90 mesh silica gel mixed samples, the column chromatography of loading progress afterwards, dress post silica gel are 180 mesh, and the weight of used silica gel is medicinal extract c weights
8 times of amounts of amount；Using volume ratio as 20:1、9:1、8:2、7:3、6:4 and 1:1 chloroform and acetone mixed organic solvents gradient elution,
Each gradient elution to TLC point plates without point after, change next gradient elution；The gradient eluent of each gradient and concentration are collected, is passed through
TLC is monitored, and merges identical part；
E, high performance liquid chromatography separation：Volume ratio will be used as 6:The part that 4 chloroform-acetone mixed organic solvents afford
Purified using high performance liquid chromatography separation, the specific method of high performance liquid chromatography separation purifying is：Using volumetric concentration as 40% first
Alcohol solution is mobile phase, and flow velocity 20ml/min, with 21.2 × 250mm, 5 μm of Zorbax PrepHT GF reverse phase preparative columns are
Stationary phase, UV-detector Detection wavelength are 365nm, each μ L of sample introduction 100, collect 39.6min chromatographic peak, after repeatedly adding up
It is evaporated, produces described flavone compound.
Wherein, the solvent of step A is ethanol.The organic solvent of the step B is ethyl acetate.
The present embodiment uses waste residue powder 4.4kg, obtains medicinal extract a 120g, medicinal extract b 80g, medicinal extract c 62g, volume ratio 6:
The part 18g that 4 chloroform-acetone mixed organic solvents afford.
Embodiment 4
The waste residue sample source after Rosa Damascana is produced in hotan, kind is Damask Rose.
A, medicinal extract extracts：Waste residue powder after production Rosa Damascana is extracted 4 times with solvent supersonic, every time Extraction solvent used
Quality be 4 times of waste residue powder quality, each extraction time is 50 minutes, merges extract solution and simultaneously filters, filtrate decompression is concentrated into
Just there is sediment precipitation, stand 40 minutes, filter out sediment, gained filtrate decompression is condensed into medicinal extract a afterwards；
B, organic solvent extracts：The water that weight is 1.2 times of medicinal extract a weight is added into medicinal extract a, then extracts 4 with organic solvent
Secondary, the volume of organic solvent used is identical with water volume every time, merges organic solvent extraction phase, has afterwards by what merging obtained
Solvent extraction phase is concentrated under reduced pressure into medicinal extract b；
C, MCI decolourizes：Into medicinal extract b, addition is that the volumetric concentration of 4.5 times of medicinal extract b weight is 95% methanol aqueous solution, treats medicinal extract b
After being completely dissolved, upper MCI posts, it is that 92% methanol aqueous solution is eluted with volumetric concentration, merges eluent, after merging afterwards
Eluent be concentrated under reduced pressure into medicinal extract c；
D, silica gel column chromatography：Medicinal extract c is first that 2.5 times of medicinal extract c acetone or methanol dissolve with weight, is then leaching with weight
0.9 times of cream c 80 mesh silica gel mixed samples, the column chromatography of loading progress afterwards, dress post silica gel are 160 mesh, and the weight of used silica gel is leaching
8 times of amounts of cream c weight；Using volume ratio as 20:1、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 point plates is without point, changes next gradient elution；Collect the gradient eluent of each gradient and dense
Contracting, is monitored through TLC, merges identical part；
E, high performance liquid chromatography separation：Volume ratio will be used as 6:The part that 4 chloroform-acetone mixed organic solvents afford
Purified using high performance liquid chromatography separation, the specific method of high performance liquid chromatography separation purifying is：Using volumetric concentration as 40% first
Alcohol solution is mobile phase, and flow velocity 23ml/min, with 21.2 × 250mm, 5 μm of Zorbax PrepHT GF reverse phase preparative columns are
Stationary phase, UV-detector Detection wavelength are 365nm, each μ L of sample introduction 80, collect 39.6min chromatographic peak, after repeatedly adding up
It is evaporated, produces described flavone compound.
Wherein, the solvent of step A is methanol.The organic solvent of the step B is ether.
The present embodiment uses waste residue powder 10kg, obtains medicinal extract a 350g, medicinal extract b 210g, medicinal extract c 150g, and volume ratio is
6:The part 55g that 4 chloroform-acetone mixed organic solvents afford.
Embodiment 5
The waste residue sample source after Rosa Damascana is produced in hotan, kind is Damask Rose.
A, medicinal extract extracts：Waste residue powder after production Rosa Damascana is extracted 4 times with solvent supersonic, every time Extraction solvent used
Quality be 5 times of waste residue powder quality, each extraction time is 35 minutes, merges extract solution and simultaneously filters, filtrate decompression is concentrated into
Just there is sediment precipitation, stand 55 minutes, filter out sediment, gained filtrate decompression is condensed into medicinal extract a afterwards；
B, organic solvent extracts：The water that weight is 1.6 times of medicinal extract a weight is added into medicinal extract a, then extracts 4 with organic solvent
Secondary, the volume of organic solvent used is identical with water volume every time, merges organic solvent extraction phase, has afterwards by what merging obtained
Solvent extraction phase is concentrated under reduced pressure into medicinal extract b；
C, MCI decolourizes：Into medicinal extract b, addition is that the volumetric concentration of 4.5 times of medicinal extract b weight is 95% methanol aqueous solution, treats medicinal extract b
After being completely dissolved, upper MCI posts, it is that 94% methanol aqueous solution is eluted with volumetric concentration, merges eluent, after merging afterwards
Eluent be concentrated under reduced pressure into medicinal extract c；
D, silica gel column chromatography：Medicinal extract c is first that 2.4 times of medicinal extract c acetone or methanol dissolve with weight, is then leaching with weight
1 times of cream c 100 mesh silica gel mixed samples, the column chromatography of loading progress afterwards, dress post silica gel are 200 mesh, and the weight of used silica gel is leaching
7 times of amounts of cream c weight；Using volume ratio as 20:1、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 point plates is without point, changes next gradient elution；Collect the gradient eluent of each gradient and dense
Contracting, is monitored through TLC, merges identical part；
E, high performance liquid chromatography separation：Volume ratio will be used as 6:The part that 4 chloroform-acetone mixed organic solvents afford
Purified using high performance liquid chromatography separation, the specific method of high performance liquid chromatography separation purifying is：Using volumetric concentration as 40% first
Alcohol solution is mobile phase, and flow velocity 18ml/min, with 21.2 × 250mm, 5 μm of Zorbax PrepHT GF reverse phase preparative columns are
Stationary phase, UV-detector Detection wavelength are 365nm, each μ L of sample introduction 120, collect 39.6min chromatographic peak, after repeatedly adding up
It is evaporated, produces described flavone compound.
Wherein, the solvent of step A is the methanol aqueous solution that volumetric concentration is 95%.The organic solvent of the step B is oil
Ether.
Embodiment 6
The structure for the flavone compound being prepared using the method for embodiment 1 is measured by the following method：
The compounds of this invention is light yellow gum thing；HRESI-MS shows that its quasi-molecular ion peak is 335.0886 [M+Na]+
(calculated value 335.0895), with reference to1H NMR and DEPT spectrum determine that its molecular formula is C18H16O5, degree of unsaturation 11.
Hydroxyl (3428), carbonyl (1665) and aromatic ring (1618,1459 and 1410cm are shown in infrared spectrum-1) resonance
Absworption peak.And ultraviolet spectra there may be aromatic ring structure in 210,262,365nm have absorption maximum to also illustrate that compound.
Compound1H and13C H NMR spectroscopies（Such as table 1, Fig. 1 and Fig. 2）Show that it contains 17 carbon and 14 hydrogen, including 1
The phenyl ring (C-5 ~ C-10, H-8) of 1,2,3,4,5- five substitution, 1 the dibasic phenyl ring of 1,2- (C-1' ~ C-6', H-3' ~ H-
6'), 1 α, beta-unsaturated carbonyl (C-4), 1 group of double bond (C-2 and C-3, H-3), 1 methyl (d C 7.91 q,d H2.49 s),
Two methoxyl groups (d C56.4 q and 55.9 q,d H3.82 s and 3.85 s), and 1 phenolic hydroxyl group (d H13.93 s).Root
According to typical 2 phenyl ring, α, beta-unsaturated carbonyl and double bond signal, it is flavone compound that can speculate compound.According to H-3 and
C-1', and H-6' are related to C-2 HMBC（Such as Fig. 3）May further confirm that compound is flavonoid structure.
After the parent of compound determines, remaining substituent, methyl, methoxyl group and phenolic hydroxyl group can be considered the substitution on flavones
Base.In the HMBC spectrums of compound（Such as Fig. 3）Can be observed two methoxyl group hydrogen (d H3.85) and C-2'(3.82 andd C
156.3) and C-7 (d C 165.9) HMBC is related, can speculate that two methoxyl groups are substituted in C-2' and C-7 positions respectively；According to methyl
Hydrogen (d H2.48) it is related to C-5, C-6, C-7 HMBC, it can be verified that methyl is substituted in C-6 positions；According to phenolic hydroxyl group hydrogen (d H
13.93) it is related to C-10 HMBC to C-5, C-6, it can be verified that the phenolic hydroxyl group is substituted in C-5 positions respectively.Other typical phenyl ring
Upper proton signal (H-8,d H6.82 s；H-3 ',d H7. 13(d) 7.6；H-4 ',d H7.32 (t) 7.6；H-5 ',d H
6.88 (t) 7.6；H-6 ',d H7.91 (d) 7.6) also the B rings of susceptible of proof chromocor compound of the present invention are that 5,6,7- positions three take
Generation, C rings are that 2'- positions are monosubstituted.
So far, the structure of compound is determined, and is named as Compound nomenclature and is：5- hydroxyls -2', 7- dimethoxy -
6- methyl-flavones.
Embodiment 7
Compound prepared by Example 2-5, is light yellow gum thing.Assay method is same as Example 6, confirms embodiment 2-
5 compounds prepared are the flavone compound --- 5- hydroxyls -2', 7- dimethoxy -6- methyl-flavones.
Embodiment 8
The chromocor compound of any preparation in Example 1-5 carries out the additive effect experiment of cigarette filter, and test situation is as follows：
For the cigarette " Hongta is classical " that addition cigarette is Hongta Group, above-mentioned chromocor compound is used with triacetyl glycerine
It is made into 0.1 mg/mL solution.Uniformly it is sprayed onto by the 8% of filter tow weight on filter tow, filter stick is made, then will
Cigarette is made by the cigarette cigarette of routine in the filter stick, carries out sensory evaluation, and to be not added with the identical cigarette of compound work
For control.Evaluation and analysis result shows：It can coordinate this perfume with tobacco, increase the sweet sense of flue gas, alleviating the throat after smoking stimulates,
With the obvious pharynx-clearing throat-benefiting effect of energy, and the suction quality of cigarette can be improved.
Embodiment 9
The flavone compound of any preparation in Example 1-5 carries out the additive effect experiment of cigarette filter：
For the cigarette " purple cloud " that addition cigarette is Hong Yun Red River group, above-mentioned flavone compound is used with triacetyl glycerine
It is made into 0.5 mg/mL solution.Uniformly it is sprayed onto by the 5% of filter tow weight on filter tow, filter stick is made, then will
Cigarette is made by the cigarette cigarette of routine in the filter stick, carries out sensory evaluation, and to be not added with the identical cigarette of compound work
For control.Evaluation and analysis result shows：The compounds of this invention can be coordinated this perfume with tobacco, increase the sweet sense of flue gas, alleviate smoking
Throat afterwards stimulates, and having can significantly pharynx-clearing throat-benefiting effect, and can improve the suction quality of cigarette.
The compounds of this invention application process not limited to this, it is first-class to may also be added to internal lining paper.
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 (8)
1. the flavone compound in a kind of rose waste residue, it is characterised in that the flavone compound is named as：5- hydroxyls-
2', 7- dimethoxy -6- methyl-flavones, English are entitled：5-hydroxy-2', 7-dimethoxy-6-methyl-flavone,
Its molecular formula is C18H16O5, its structural formula such as formula（I）It is shown：
, formula（I）.
2. the preparation method of the flavone compound in rose waste residue described in claim 1, it is characterised in that to produce rose
Waste residue after essential oil is raw material, is extracted through medicinal extract, organic solvent extracts, MCI decolourizes, silica gel column chromatography and high performance liquid chromatography divide
It is made from step, is specially：
A, medicinal extract extracts：Waste residue powder after production Rosa Damascana is extracted 2 ~ 5 times with solvent supersonic, each Extraction solvent used
Quality is 2 ~ 6 times of waste residue powder quality, and each extraction time is 30 ~ 60 minutes, merges extract solution and filters, filtrate decompression concentration
To just there is sediment precipitation, 20 ~ 60 minutes are stood, sediment is filtered out, gained filtrate decompression is condensed into medicinal extract a afterwards；
B, organic solvent extracts：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 decolourizes：Into medicinal extract b, addition is that the volumetric concentration of 3 ~ 5 times of medicinal extract b weight is 95% methanol aqueous solution, treats medicinal extract b
After being completely dissolved, upper MCI posts, it is that 90% ~ 95% methanol aqueous solution is eluted with volumetric concentration, merges eluent, will close 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 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, each gradient elution
To TLC point plates without point after, change 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 6:The part that 4 chloroform-acetone mixed organic solvents afford
Purified using high performance liquid chromatography separation, produce described flavone compound.
3. the preparation method of the flavone compound in rose waste residue according to claim 2, it is characterised in that the A
The solvent of step is aqueous acetone solution, the ethanol water that volumetric concentration is 90 ~ 100% or the volume that volumetric concentration is 70 ~ 100%
Concentration is 90 ~ 100% methanol aqueous solution.
4. the preparation method of the flavone compound in rose waste residue according to claim 2, it is characterised in that the B
The organic solvent of step is dichloromethane, chloroform, ethyl acetate, ether or petroleum ether.
5. the preparation method of the flavone compound in rose waste residue according to claim 2, it is characterised in that the D
Medicinal extract c is first that 1.5 ~ 3 times of medicinal extract c acetone or methanol dissolve with weight before through silica gel column chromatography in step, Ran Houyong
Weight is 0.8 ~ 1.2 times of medicinal extract c 80 ~ 100 mesh silica gel mixed samples, afterwards loading.
6. the preparation method of the flavone compound in rose waste residue according to claim 2, it is characterised in that the D
In step, 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 point plates without point after, change next gradient elution.
7. the preparation method of the flavone compound in rose waste residue according to claim 2, it is characterised in that the E
The high performance liquid chromatography separation purifying of step is 15 ~ 25ml/ of flow velocity using the methanol aqueous solution that volumetric concentration is 40% as mobile phase
Min, with 21.2 × 250mm, 5 μm of Zorbax PrepHT GF reverse phase preparative columns are stationary phase, UV-detector Detection wavelength
For 365nm, each μ L of sample introduction 50 ~ 200,39.6min chromatographic peak is collected, is evaporated after repeatedly adding up.
8. the flavone compound in rose waste residue described in claim 1 is as the application for preparing cigarette filter-tip additive agent.
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