CN108586415A - The method for preparing high-purity cyanidin from violet cabbage - Google Patents
The method for preparing high-purity cyanidin from violet cabbage Download PDFInfo
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- CN108586415A CN108586415A CN201810345770.8A CN201810345770A CN108586415A CN 108586415 A CN108586415 A CN 108586415A CN 201810345770 A CN201810345770 A CN 201810345770A CN 108586415 A CN108586415 A CN 108586415A
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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
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
- C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
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Abstract
High-purity cyanidin is expensive, but is required reference substance in research and production.The invention discloses a kind of method preparing high-purity cyanidin from violet cabbage, the concrete operation step of this method is as follows：1. cyanin solution is made from fresh violet cabbage extraction；2. cyanin crude product is made in preliminary purification；3. cyanin is prepared into cyanidin (aglycon) solution through sour water solution；4. purifying again, being refined, the cyanidin powder that purity is more than 98% is obtained.Raw material of the present invention are cheap and easily-available, and method is easy to operate, and organic solvent used is cheap, and cyanidin standard items yield is high.
Description
Technical field
The present invention relates to field of natural product chemistry, and in particular to a kind of to prepare high-purity cyanidin from violet cabbage
Method.
Background technology
Anthocyanidin (Anthocyanidin) is a kind of natural pigment and plant petals being widely present in nature
Main color-generation substance.All there is anthocyanidin in belonging in 27 sections 72 of flowering plant (angiosperm), as violet cabbage, purple sweet potato,
Grape, rose, blueberry, eggplant etc..According to the difference of substituent group, a variety of anthocyanidin can be formed, such as delphinidin, corn flower
Pigment, pelargonidin etc..The anthocyanidin aglycon of free state is very rare under field conditions (factors), often passes through sugar with various monosaccharide
Glycosidic bond connects to form anthocyanidin glucosides, and glycosylation rear polarity and water solubility all can accordingly increase.Hydroxyl in anthocyanidin glucosides is also
The anthocyanin being acylated can be formed by ester bond with the coumaric acid, ferulic acid, caffeic acid of one or more molecules etc..
Nature is abundant, the anthocyanidin of Nantural non-toxic is not only edible, but also has superior nutrition and health care effect.
The significant physiological function of anthocyanidin one is antioxidant activity, in addition, it also has antibacterial, anti-aging, reduces cancer
The important physiological function with the incidence of angiocardiopathy etc..These physiological activity based on anthocyanidin, the correlation of anthocyanidin are ground
Study carefully and has become hot spot.The research in relation to anthocyanidin both at home and abroad is concentrated mainly on research, the cyanine of anthocyanin extraction purification at present
The research of plain physicochemical property and stability, the research of anthocyanidin physiological activity, the application of anthocyanidin product and exploitation and cyanine
Anabolic regulation and control of element etc..Wherein it is the basis of other anthocyanidin research, therefore people to the extraction purification of anthocyanin
It is very big for the research input of various anthocyanidin extraction purifications.Existing patent report be also focus mostly in natural anthocyanin and
On the extracting and developing and purifying of its derivative, such as the preparation method (CN102229632A) of C-3-G；Portugal
The extracting method (CN1634915A) of anthocyanidin in grape seed；Extracting method (CN101914304A) of blueberry anthocyanin etc..
Edible vegetable violet cabbage abundance, the same with other cyanine glycoside pigments, purple cabbage pigment has very strong anti-
Oxidability, also antitumor, prevention cardiovascular and cerebrovascular disease and other effects, has very high researching value.And liquid chromatography-mass spectrography
Method (LC-MS) analysis shows, in violet cabbage anthocyanidin contain 16 kinds of components, they are substantially a series of sugar of cyanidin
Glycosides and its acylate.The extraction purification technology of anthocyanin has been mature on the whole in violet cabbage, but related preparation high-purity anthocyanidin
The method of plain aglycon, document report are less.And anthocyanidin aglycon, as the precursor that anthocyanin and catechin synthesize,
It studies in the regulation and control of flavonoids biosynthetic metabolism, it is essential as standard substance.But anthocyanidin element aglycon is expensive, example
If the cyanidin monomer of cyanidin, commercially available 95% purity is 842.4 yuan/milligram (http of RMB://
Www.sigmaaldrich.com/china-mainland.html), the cyanin of inexpensive high-purity is utilized
Member has prodigious market prospects.
From violet cabbage, then extraction purification anthocyanin hydrolyzes to obtain anthocyanin the present invention using sour technology for hydrolyzing
Member using purifying, refines, high-purity free state cyanidin aglycon is prepared.Raw material of the present invention are cheap and easily-available, side
Method is easy to operate, and organic solvent used is cheap, and cyanidin standard items yield is high.
Invention content
Technical problem to be solved by the present invention lies in provide a kind of side preparing high-purity cyanidin from violet cabbage
Method, to prepare the cyanidin standard items of high-purity.
The technical problems to be solved by the invention are realized using following technical scheme：
The method for preparing high-purity cyanidin from violet cabbage, including following operating procedure：
Bu Sudden 1, it takes violet cabbage blade to be put into extracting solution, obtains the homogenate of cyanin after crushed, it will be even
Slurries centrifuging and taking supernatant, obtains cyanin solution；
Bu Sudden 2, pure water is added in cyanin solution, after mixing upper AB-8 macroporous resin columns, after absorption
It is eluted, and collects eluent, obtain the cyanin solution of preliminary purification；
Concentrated hydrochloric acid is added in the cyanin solution of preliminary purification in step 3, through hydrolyzing to obtain cyanidin hydrolysis
Solution；
Pure water is added in step 4 in cyanidin hydrating solution, and upper C18 columns, are washed after absorption after mixing
It is de-, and collect eluent；
The eluent that step 4 is collected is crossed AB-8 macroreticular resins and is purified and concentrated by step 5, then is eluted with pure methanol,
Collect to obtain cyanidin solution；
Step 6 evaporates cyanidin solution, stops evaporation when having Precipitation, and concentrated hydrochloric acid is added, is put after shaking up
Enter deepfreeze, precipitation is collected by centrifugation after refrigeration, most obtains the cyanidin that purity is more than 98% through drying afterwards.
Further improvement lies in that the extracting solution is 60% ethanol water for 1% (w/v) with concentration of hydrochloric acid.
Further improvement lies in that in cyanin solution and the pure water volume ratio of addition being 1 in step 2:3；Step 4
In in cyanidin hydrating solution and the pure water volume ratio of addition be 1:3.
Further improvement lies in that described in step 2 elute the step of for successively respectively use pure water, 20% ethanol solution,
60% ethanol solution elutes, and collects 60% high ethanol solution eluent of cyanin content.
Further improvement lies in that the cyanin solution of the preliminary purification and the volume ratio of concentrated hydrochloric acid are 4:1.
Further improvement lies in that the step of hydrolysis is to hydrolyze 1h in 90 DEG C of constant water bath box.
Further improvement lies in that the step of being eluted described in step 4 is successively respectively with pure water, 20% methanol solution, 50%
Methanol solution elutes, and collects 50% high methanol solution eluent of cornflowerblue cellulose content.
Further improvement lies in that the step of evaporation is using Rotary Evaporators, 10- is evaporated under 40 DEG C of water-baths
30min。
Further improvement lies in that the step of deepfreeze is to be put into 4 DEG C of refrigeration 1h in refrigerator.
Further improvement lies in that the step of drying is to be dried up using nitrogen evaporator.
The principle of the present invention is：
Anthocyanidin is a kind of natural pigment being widely present in nature, under field conditions (factors), the anthocyanidin of free state
Aglycon is very rare, mainly forms anthocyanidin glucosides by glucosides key connection with various sugar.Glycosidic bond under strong acid hot conditions,
It can hydrolyze, form anthocyanidin aglycon.Violet cabbage is rich in cyanin, can first pass through extraction purification and obtain cyanidin
Then glycosides utilizes sour technology for hydrolyzing, hydrolyzes to obtain cyanidin aglycon, be further purified to obtain cyanidin standard items.
The beneficial effects of the invention are as follows：
1, this method is easy to operate, does not need Large expensive laboratory apparatus, organic solvent used is cheap, and recyclable
It uses, it is at low cost；
2, violet cabbage is Vegetables, and experiment material derives from a wealth of sources；
3, this method can effectively remove sugar, albumen, other types anthocyanin and flavone compound in extract, obtain
High-purity corn flower standard items are used for scientific research and production；
Description of the drawings
Fig. 1 is the optimization comparison diagram that cyanin condition is extracted from violet cabbage；
Fig. 2 is the optimization comparison diagram of AB-8 macroreticular resin preliminary purification cyanin conditions；
Fig. 3 is the optimization comparison diagram of C18 column purification cyanidin conditions；
The cyanidin two-dimensional highly effective liquid phase chromatographic figure that Fig. 4 is obtained after purification；
The cyanidin three dimension high efficiency liquid chromatogram that Fig. 5 is obtained after purification.
Specific implementation mode
In order to make the technical means, the creative features, the aims and the efficiencies achieved by the present invention be easy to understand, tie below
Conjunction is specifically illustrating and embodiment, and the present invention is further explained.
Embodiment：
Capital equipment：1. high performance liquid chromatograph (HPLC)；2. thermostat water bath；3. Rotary Evaporators；4. centrifuge；5.
Bruisher；6. chromatographing glass column；7. nitrogen evaporator.
Material and reagent：
1, it is detected material：Violet cabbage (is bought) in the market.
2, main agents：
Ethyl alcohol (analysis is pure), methanol (analysis is pure), concentrated hydrochloric acid；
Extracting solution：It takes 60 milliliters of ethyl alcohol that 39 milliliters of water and 1 milliliter of concentrated hydrochloric acid is added, shakes up.
Eluent：It takes 40 milliliters of ethyl alcohol that 59 milliliters of water and 1 milliliter of concentrated hydrochloric acid is added, shakes up.
20% methanol：20 ml methanols are added in 80 milliliters of water, shake up.
50% methanol：50 ml methanols are added in 50 milliliters of water, shake up.
The method concrete operation step that high-purity cyanidin is prepared from violet cabbage is as follows：
The extraction of step 1, cyanin
First pass through contrast experiment detects influence of the acidic alcohol extracting solution of various concentration to recovery rate respectively in advance, obtains reality
Test data as shown in Figure 1, wherein Figure 1A be concentration of hydrochloric acid it is identical, the extraction effect in the case of concentration of alcohol difference can be seen
It is best to go out extraction effect under the conditions of 60% concentration of alcohol；Figure 1B is that concentration of alcohol is identical, in the case of concentration of hydrochloric acid difference
Extraction effect, it can be seen that extraction effect is best under the conditions of 1% concentration of hydrochloric acid；Fig. 1 C are the extraction in the case of different feed liquid ratio
Effect, it can be seen that solid-liquid ratio 1:Recovery rate highest when 30.For this purpose, taking 100g violet cabbage blades, it is put into the tissue of 2L volumes
In bruisher, 60% ethanol water that addition 1L concentration of hydrochloric acid is 1% (w/v) is as extracting solution, 1000r/min homogenate
5min.Homogenate is collected, 5000r/min centrifuges 10min at 4 DEG C, collects supernatant, obtains cyanin solution.
Step 2, cyanin preliminary purification
AB-8 macroreticular resin preliminary purification cyanins under contrast experiment's detection different ethanol concentration are first passed through in advance to obtain
Scheme to cyanin crude product solution efficiency comparative, the experimental data obtained is as shown in Figure 2, it can be seen that when concentration of alcohol exists
Efficiency highest when 40%.For this purpose, by volume, cyanin solution：Pure water=1:3 are added pure water 3L, are uniformly mixed, on
AB-8 macroporous resin columns.Successively 1L pure water, 1L20% ethanol solutions is used to elute respectively after absorption, then molten with 500mL60% ethyl alcohol
Liquid elutes, and makes average ethanol a concentration of 40% or so in solution, then collects 60% high ethyl alcohol of content containing cyanin
Solution eluent obtains cyanin crude product solution about 200mL.
The preparation of step 3, cyanidin solution
By volume, cyanin solution：Concentrated hydrochloric acid=4:1,50mL concentrated hydrochloric acids are added, are placed on 90 DEG C of waters bath with thermostatic control
1h is hydrolyzed in case, obtains cyanidin hydrating solution about 250mL.
The purifying of step 4, cyanidin
First passing through contrast experiment detects different methanol concentrations to the purification effect of C18 column purification cyanidins in advance, obtains
Experimental data it is as shown in Figure 3, wherein A：30% meoh eluate purification effect；B：50% meoh eluate purification effect；C：
70% meoh eluate purification effect.It can be seen that 50% meoh eluate purification effect is best.For this purpose, by arrow obtained above
Vehicle asterin solution, by volume, cyanin solution：Pure water=1:3 are added pure water 750mL, and C18 columns are gone up after mixing,
It successively uses the methanol of 500mL pure water, 500mL20% and 200mL50% to elute after absorption respectively, it is high to collect cornflowerblue cellulose content
50% meoh eluate about 200mL.
Obtained cyanidin solution is crossed AB-8 macroreticular resins by step 2 again and is purified and concentrated by step 5.Most
The pure methanol elutions of 100mL are used afterwards, collect to obtain cyanidin solution about 100mL.
The preparation of step 6, cyanidin sterling
Cyanidin solution evaporates 10-30min using Rotary Evaporators under 40 DEG C of water-baths, Precipitation to be had stops
Only evaporate.Concentrated hydrochloric acid 1mL is added, 4 DEG C of refrigerators 1h, 5000r/min is put into after shaking up, precipitation is collected by centrifugation, nitrogen evaporator drying obtains
Obtain cyanidin sterling.
In conjunction with shown in Fig. 4 to Fig. 5, the HPLC of cyanidin obtained above is analyzed：
Utilize the purity for the cyanidin sterling that high-efficient liquid phase chromatogram technology (HPLC) detection purifying obtains.
HPLC chromatogram condition：Japanese Shimadzu 20AD high performance liquid chromatographs；Chromatographic column：The holy and pure orchid 4u spoke depths 250* of Féraud door
4.6mm(PhenomenexSynergi4uFusion250*4.6mm)；Detector：The Japanese ultraviolet inspection of Shimadzu SPD6AV wavelengthtunables
Survey device；Sensitivity：0.01；Detection wavelength：530nm；Flow velocity：1.0 ml/min；Sample size：5 microlitres；Using gradient elution item
Part A phases：1% acetic acid, B phases：Trifluoroacetic acid aqueous solution, gradient be first 30 minutes in A phases by 87% to 70%, B phases by 13% to
30%；30 minutes to 33 minutes, A phases were by 70% to 87%, B phases by 30% to 13%.
Testing result finds that there are one single absorption peaks, analysis to be found to be arrow vehicle at 12.05min or so, 530nm
Asterin peak.The purity of the cyanidin obtained using present invention extraction is more than 98%, very high purity.It is sent out through quantitative analysis
Existing, the cyanidin that extraction purification of the present invention obtains reaches 20mg/100g violet cabbage fresh leafs, and yield is 0.2mg/g (fresh weight).
The basic principles, main features and advantages of the invention have been shown and described above.The technical staff of the industry should
Understand, the present invention only illustrates the present invention not by the exemplary limitation of above-mentioned implementation described in above-mentioned implementation example and specification
Principle, without departing from the spirit and scope of the present invention, various changes and improvements may be made to the invention, these variation and
Improvement all fall within the protetion scope of the claimed invention.The claimed scope of the invention is by appended claims and its equivalent
Object defines.
Claims (10)
1. the method for preparing high-purity cyanidin from violet cabbage, which is characterized in that including following operating procedure：
Bu Sudden 1, it takes violet cabbage blade to be put into extracting solution, obtains the homogenate of cyanin after crushed, by homogenate
Centrifuging and taking supernatant obtains cyanin solution；
Step Sudden 2, pure water is added in cyanin solution, upper AB-8 macroporous resin columns, carry out after absorption after mixing
Elution, and eluent is collected, obtain the cyanin solution of preliminary purification；
Concentrated hydrochloric acid is added in the cyanin solution of preliminary purification in step 3, through hydrolyze cyanidin hydrolysis it is molten
Liquid；
Pure water is added in step 4 in cyanidin hydrating solution, and upper C18 columns, are eluted after absorption after mixing, and
Collect eluent；
The eluent that step 4 is collected is crossed AB-8 macroreticular resins and is purified and concentrated by step 5, then is eluted with pure methanol, is collected
Obtain cyanidin solution；
Step 6 evaporates cyanidin solution, stops evaporation when having Precipitation, and concentrated hydrochloric acid is added, is put into after shaking up low
Temperature refrigeration, is collected by centrifugation precipitation after refrigeration, most obtain cyanidin through drying afterwards.
2. the method according to claim 1 for preparing high-purity cyanidin from violet cabbage, it is characterised in that：It is described to carry
It takes liquid and is with 60% ethanol water that concentration of hydrochloric acid is 1% (w/v).
3. the method according to claim 1 for preparing high-purity cyanidin from violet cabbage, it is characterised in that：Step 2
In in cyanin solution and the pure water volume ratio of addition be 1:3；In cyanidin hydrating solution and addition in step 4
Pure water volume ratio be 1:3.
4. the method according to claim 1 for preparing high-purity cyanidin from violet cabbage, it is characterised in that：Step 2
Described in the step of eluting successively to use pure water, 20% ethanol solution, the elution of 60% ethanol solution respectively, and collect cornflowerblue
60% high ethanol solution eluent of plain glycosides content.
5. the method according to claim 1 for preparing high-purity cyanidin from violet cabbage, it is characterised in that：It is described first
The volume ratio of the cyanin solution and concentrated hydrochloric acid that walk purifying is 4:1.
6. the method according to claim 1 for preparing high-purity cyanidin from violet cabbage, it is characterised in that：The water
The step of solution is to hydrolyze 1h in 90 DEG C of constant water bath box.
7. the method according to claim 1 for preparing high-purity cyanidin from violet cabbage, it is characterised in that：Step 4
The step of elution is successively to use pure water, 20% methanol solution, the elution of 50% methanol solution respectively, and collect cyanidin
50% high methanol solution eluent of content.
8. the method according to claim 1 for preparing high-purity cyanidin from violet cabbage, it is characterised in that：The steaming
The step of hair is to evaporate 10-30min under 40 DEG C of water-baths using Rotary Evaporators.
9. the method according to claim 1 for preparing high-purity cyanidin from violet cabbage, it is characterised in that：It is described low
The step of temperature refrigeration, refrigerates 1h for 4 DEG C to be put into refrigerator.
10. the method according to claim 1 for preparing high-purity cyanidin from violet cabbage, it is characterised in that：It is described
The step of drying is to be dried up using nitrogen evaporator.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102229632A (en) * | 2011-05-25 | 2011-11-02 | 北京市农林科学院 | Preparation method of cyaniding-3-O-glucoside chloride |
| CN102746266A (en) * | 2012-07-13 | 2012-10-24 | 安徽农业大学 | Method for preparing high-purity cornflower pigment |
| CN107686473A (en) * | 2017-09-26 | 2018-02-13 | 福州大学 | A kind of gynura bicolor polysaccharide polyphenol combined preparation process |
-
2018
- 2018-04-18 CN CN201810345770.8A patent/CN108586415A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102229632A (en) * | 2011-05-25 | 2011-11-02 | 北京市农林科学院 | Preparation method of cyaniding-3-O-glucoside chloride |
| CN102746266A (en) * | 2012-07-13 | 2012-10-24 | 安徽农业大学 | Method for preparing high-purity cornflower pigment |
| CN107686473A (en) * | 2017-09-26 | 2018-02-13 | 福州大学 | A kind of gynura bicolor polysaccharide polyphenol combined preparation process |
Non-Patent Citations (1)
| Title |
|---|
| ISADORA R. N. DE OLIVEIRA ET AL.: "Evaluation of potential interfering agents on in vitro methods for the determination of the antioxidant capacity in anthocyanin extracts", 《INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY》 * |
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Application publication date: 20180928 |