CN108358944A - A kind of preparation method of pyranoid form anthocyanidin aglycon - Google Patents
A kind of preparation method of pyranoid form anthocyanidin aglycon Download PDFInfo
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- CN108358944A CN108358944A CN201810377217.2A CN201810377217A CN108358944A CN 108358944 A CN108358944 A CN 108358944A CN 201810377217 A CN201810377217 A CN 201810377217A CN 108358944 A CN108358944 A CN 108358944A
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- anthocyanidin
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
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Abstract
The invention discloses a kind of preparation method of pyranoid form anthocyanidin aglycon, method is:Step 1: extraction:Homogenate is made in Blueberry raw material after crushing, filters out extracting solution, residue extracts 23 times again;Step 2: extraction:Extracting solution after reduced pressure is subjected to liquid-liquid extraction with ethyl acetate;Step 3: column chromatography is concentrated under reduced pressure, blueberry anthocyanin refined solution is made;Step 4: sour water solution:It is concentrated under reduced pressure, blueberry anthocyanin aglycon hydrolyzate is made;Step 5: column chromatography:It is concentrated under reduced pressure, blueberry anthocyanin aglycon refined solution is made;Step 6: chemical synthesis:After drying, the pyranoid form anthocyanidin aglycon that purity is 60 70% is made.Beneficial effects of the present invention:Pyranoid form anthocyanidin aglycon product obtained by the present invention, had not only remained the multiple efficacies of original anthocyanidin, but also increase significantly in stability than original anthocyanidin, and can expand application of the anthocyanidin in fields such as food, drug, cosmetics, chemical industry.
Description
Technical field
The present invention relates to a kind of preparation method of anthocyanidin aglycon, more particularly to a kind of preparation of pyranoid form anthocyanidin aglycon
Method.
Background technology
In recent years, with the fast development of China's food industry, food colour industry is also gradually developed.Due to
Synthetic food color stability is good, strong coloring force, and synthetic food color has dominated the city of China's food colour in very large range
.But since synthetic dyestuff generally carries certain toxicity, or even there is carcinogenesis, in contrast, natural pigment has peace
The advantages that Quan Xinggao, high nutritive value, with the food-safe attention of people, natural pigment is expected to gradually replace artificial synthesized
Pigment is studied, develops the trend that nontoxic natural pigment has become food colour industry development.Anthocyanidin is as a kind of
Natural food colour has shown good ecology potential because of its abundance, safe and non-toxic in food colour application field
Head;In addition, lot of domestic and foreign research report shows that anthocyanidin has anti-oxidant, anti-inflammatory, anticancer, anti-lipid, improvement eyesight etc.
Multiple functions activity, has wider application prospect in health food, medicine, cosmetics, bioengineering and chemical field.But
It is more sensitive to light, heat, metal, pH value since that there are stability is poor for anthocyanidin, it is received so as to cause its application serious
Limitation.The stability for how improving anthocyanidin has become the urgent task of scientific research personnel faced.
The cyanine prime form to dissociate under natural conditions is extremely rare, and anthocyanidin is mainly in the form of glycosides derivatives (anthocyanin)
It is present in the plants such as fruit or vegetables, such as anthocyanidin glycosylation, is acylated form, it is known that naturally occurring anthocyanin has 500
Remaining kind.Pyranoid form anthocyanidin (Pyranoanthocyanins) is a kind of novel anthocyanidin derivative, after being primarily present in fermentation
Fruit wine or fruit juice in, be between C4 and C5 of original anthocyanidin hydroxyls through be cyclized addition reaction increase newly a pyranoid ring,
A kind of more stable anthocyanidin configuration formed.Naturally occurring pyranoid form anthocyanidin is more rare, it has now been found that pyrans
Type anthocyanidin is mostly derived from grape wine, such as methyl type, carboxyl type, phenolic group type, flavane alcohol type, Portisins type pyrans cyanine
Element.Compared with the anthocyanidin of general configuration, pyranoid form anthocyanidin, can be with because foring new pyranoid form between C4 and C5 hydroxyl
Directly protection anthocyanidin molecule is by water or SO2Nucleophillic attack so that pyranoid form anthocyanidin is to pH and SO2Have stronger resistance to
Stress will be shown huge in view of the higher stability of pyranoid form anthocyanidin in fields such as food, drug and cosmetics
Application potential.
Currently, existing more money anthocyanidin products on domestic and international market, such as extract, soft capsule, oral solution, MASQUE APAISANT HYDRATANT
Etc. various forms of anthocyanidin products.With the continuous deepening of research, the product of more anthocyanidin will moves towards market.By right
The anthocyanidin product of market is analyzed, we send out the glycoside forms that now nearly all anthocyanidin product belongs to anthocyanidin
(anthocyanin).Up to the present, it there is no the sale of pyranoid form anthocyanidin product, exploitation high stability, height living on domestic and international market
Property pyranoid form anthocyanidin product have great market potential and application space.It is in recent years, existing that some literature reports pyrroles
The preparation method of type of muttering anthocyanidin prepares pyranoid form cyanine such as using the grape wine after ageing as raw material by isolating and purifying means
Element, or using Grape Skin cyanidin extract as raw material by chemical synthesis and isolates and purifies means and prepares pyranoid form anthocyanidin.It is logical
Cross access patented technology, the country's only 1 related patents report, such as Chinese patent (patent name:A kind of Methylpyrane anthocyanin
Preparation method and applications, application number:CN201610556696.5 a kind of preparation method of pyrans anthocyanidin) is related to, it should
Method for raw material, after being mixed with a certain amount of acetone, is passed through with anthocyanidin standard items (Cyanidin -3-O- glucosides)
After standing 30 days, using chromatography post separation, and then Methylpyrane anthocyanin is made in ultrasonication.This method with it is existing
Technology is compared, and the rate of synthesizing methyl pyrans anthocyanin is very fast, and yield is high, product purity is high, is a kind of promising preparation
The method of Methylpyrane anthocyanin.But since this method depends on the limitation of anthocyanidin standard items raw material, and reaction time nearly 1
A month or so, reaction time was longer, was not suitable for preparing pyrans anthocyanidin product on a large scale, gained sample can not directly apply to
Food, medicine and other fields.In addition, the Methylpyrane anthocyanidin obtained by this method is glycoside forms.
Invention content
The purpose of the present invention is to solve existing preparation methods to be not suitable for preparing pyrans anthocyanidin product on a large scale,
Gained sample can not directly apply to the problem of food, medicine and other fields and the preparation of a kind of pyranoid form anthocyanidin aglycon that provides
Method.
The preparation method of pyranoid form anthocyanidin aglycon provided by the invention, preparation method are as described below:
Step 1: extraction:Homogenate is made in Blueberry raw material after crushing, with 1:3-1:5 volume ratio is even to fruit
The ethanol solution of 60-80% is added in slurry, adjusting pH value is 1.0-3.0, and after stirring 0.5 hour, black out impregnates 24- at room temperature
72 hours;Extracting solution is filtered out, residue extracts 2-3 times again;
Step 2: extraction:Extracting solution after reduced pressure is subjected to liquid-liquid extraction with ethyl acetate, volume ratio is by extraction
Liquid:Ethyl acetate is 1:2-1:4, black out extraction 2-3 times at room temperature, the time is 24 hours/time, collects water layer anthocyanidin part
It is spare;
Step 3: column chromatography:Water layer anthocyanidin obtained in step 2 is partially loaded macroporous resin column, single loading body
Product is the 1/8-1/12 of resin volume, first rinses pillar, then the salt containing 0.01-0.05% with concentration 35-45% with deionized water
The ethanol solution elution of acid, collects the ethanol eluate of 35-45%, is concentrated under reduced pressure, blueberry anthocyanin refined solution is made;
Step 4: sour water solution:By blueberry anthocyanin refined solution obtained in step 3 and 2.5-4.0mol/L hydrochloric acid solutions
By volume 1:4-1:8 mixings, and the absolute ethyl alcohol of 10-20% is added, heating water bath 1-1.5 hours at 95-100 DEG C, take
Rapid cooling room temperature, is concentrated under reduced pressure, blueberry anthocyanin aglycon hydrolyzate is made after going out;
Step 5: column chromatography:By solid phase extraction column or upper macropore on anthocyanidin aglycon hydrolyzate obtained in step 4
Resin column, applied sample amount are the 1/3-1/5 of column volume, are first eluted with deionized water, elute 3-5 times of column volume, then use concentration
The ethanol solution of the hydrochloric acid containing 0.01-0.05% of 60-80% elutes, and collects the ethanol eluate of 60-80%, is concentrated under reduced pressure, system
Obtain blueberry anthocyanin aglycon refined solution;
Step 6: chemical synthesis:By the acetone water of blueberry anthocyanin aglycon refined solution obtained and 50-80% in step 5
Solution by volume 1:30-1:50 mixings, and the absolute ethyl alcohol of 10-20% is added, adjust reacting solution pH value range with hydrochloric acid
Between 1.5-4.5, heating water bath 3-8 days at 30-55 DEG C, after reaction, reaction solution is through being concentrated under reduced pressure, and after dry, is made
Purity is the pyranoid form anthocyanidin aglycon of 60-70%.
Blueberry raw material described in step 1 is by blueberry fresh fruit or blueberry freeze fruit or blueberry powder or blueberry pomace
It is made.
The condition of reduced pressure in step 2 to step 6 is:40-55 DEG C of temperature range, vacuum degree<0.09MPa is dense
Final volume reaches the 1/5-1/10 for original solution volume after contracting.
Model Amberlite XAD-7HP of big pore resin in step 3 and step 5, AB-8, NKA-9 and
One kind in D101;The model SEP-PAK C of solid phase extraction column described in step 518。
Dried forms are vacuum freeze drying in step 6, and drying condition is:- 45 DEG C to -55 DEG C of temperature range, vacuum degree
<50Pa, time 24-48h.
Step 4 should be prior to chemical synthesis step with acid hydrolysis step involved in step 6, and the two sequencing is not
It can overturn.
Beneficial effects of the present invention:The preparation method of pyranoid form anthocyanidin aglycon provided by the invention is original with Blueberry
Material has synthesized pyranoid form anthocyanidin aglycon, pyranoid form cyanine on the basis of anthocyanidin glucosides, anthocyanidin aglycon is made in priority
The chemical constitution and preparation process of plain aglycon are specific as follows:
Due to domestic at present only for the report of pyranoid form anthocyanidin glucosides, there has been no for pyranoid form anthocyanidin aglycon
Document or patent of invention report, further investigation or developing pyranoid form anthocyanidin aglycon potential function and application value have
Significance.
Pyranoid form anthocyanidin aglycon product obtained by the present invention had both remained the multiple efficacies of original anthocyanidin (as resisted
Oxidation, antitumor, anti-inflammatory etc.), and increase significantly in stability than original anthocyanidin, such as more resistant to neutral or alkalescent
PH environment, to SO2There is stronger tolerance to act on, anthocyanidin answering in fields such as food, drug, cosmetics, chemical industry can be expanded
With.
Description of the drawings
Fig. 1 is the high-efficient liquid phase chromatogram that anthocyanidin aglycon is made in blueberry anthocyanin of the present invention after sour water solution.(figure
Middle No. 1-5 is respectively:1, delphinidin;2, Cyanidin;3, florigen of leading a cow;4, paeonidin;5, malvidin).
Fig. 2 is the ultraviolet-visible spectrogram that No. 1 peak corresponds to monomer (delphinidin) in Fig. 1.
Fig. 3 is the ultraviolet-visible spectrogram that No. 2 peaks correspond to monomer (Cyanidin) in Fig. 1.
Fig. 4 is the ultraviolet-visible spectrogram that No. 3 peaks correspond to monomer (florigen of leading a cow) in Fig. 1.
Fig. 5 is the ultraviolet-visible spectrogram that No. 4 peaks correspond to monomer (paeonidin) in Fig. 1.
Fig. 6 is the ultraviolet-visible spectrogram that No. 5 peaks correspond to monomer (malvidin) in Fig. 1.
Fig. 7 is efficient liquid of the blueberry anthocyanin aglycon of the present invention through pyranoid form anthocyanidin aglycon made from chemical synthesis
Phase chromatogram.(No. 1-5 is respectively in figure:1, pyranoid form delphinidin;2, pyranoid form Cyanidin;3, pyranoid form is led a cow florigen;
4, pyranoid form paeonidin;5, pyranoid form malvidin)
Fig. 8 is the ultraviolet-visible spectrogram that No. 1 peak corresponds to monomer (pyranoid form delphinidin) in Fig. 7.
Fig. 9 is the ultraviolet-visible spectrogram that No. 2 peaks correspond to monomer (pyranoid form Cyanidin) in Fig. 7.
Figure 10 is the ultraviolet-visible spectrogram that No. 3 peaks correspond to monomer (pyranoid form lead a cow florigen) in Fig. 7.
Figure 11 is the ultraviolet-visible spectrogram that No. 4 peaks correspond to monomer (pyranoid form paeonidin) in Fig. 7.
Figure 12 is the ultraviolet-visible spectrogram that No. 5 peaks correspond to monomer (pyranoid form malvidin) in Fig. 7.
Figure 13 is the High Performance Liquid Chromatography/Mass Spectrometry figure that No. 1 peak corresponds to monomer (pyranoid form delphinidin) in Fig. 7.
Figure 14 is the High Performance Liquid Chromatography/Mass Spectrometry figure that No. 2 peaks correspond to monomer (pyranoid form Cyanidin) in Fig. 7.
Figure 15 is the High Performance Liquid Chromatography/Mass Spectrometry figure that No. 3 peaks correspond to monomer (pyranoid form lead a cow florigen) in Fig. 7.
Figure 16 is the High Performance Liquid Chromatography/Mass Spectrometry figure that No. 4 peaks correspond to monomer (pyranoid form paeonidin) in Fig. 7.
Figure 17 is the High Performance Liquid Chromatography/Mass Spectrometry figure that No. 5 peaks correspond to monomer (pyranoid form malvidin) in Fig. 7.
Specific implementation mode
It please refers to Fig.1 to shown in Figure 17:
Embodiment 1
Step 1: extraction:Homogenate is made in freezing Blueberry raw material after crushing, is added in glass container with cover, with
1:70% ethanol solution is added in 5 volume ratio in being homogenized to Blueberry, with salt acid for adjusting pH value 3.0, stir 0.5 hour
Afterwards, black out impregnates 72 hours at room temperature;Extracting solution is filtered out, residue extracts 2 times again;
Step 2: extraction:Extracting solution after reduced pressure is poured into separatory funnel, liquid liquid extraction is carried out with ethyl acetate
It takes, volume ratio presses extracting solution:Ethyl acetate is 1:2, black out extraction 3 times at room temperature, the time is 24 hours/time, first will every time
Ester layer is poured out through top, then water layer is collected by lower section spare;
Step 3: column chromatography:Aqueous fraction anthocyanidin extraction solution is packed into Amberlite XAD-7 macropores by wet method
Resin column, single loading volume are the 1/10 of resin volume, first rinse pillar with the deionized water that 0.01% hydrochloric acid is acidified, are used for
The water-soluble impurity such as reduced sugar, albumen, organic acid in sample is removed, after eluting 5 times of column volumes, then containing with concentration 40%
The ethanol solution of 0.01% hydrochloric acid elutes, and collects 40% ethanol eluate, is concentrated under reduced pressure, and blueberry anthocyanin refined solution is made.
Step 4: sour water solution:By blueberry anthocyanin refined solution and 3.0mol/L hydrochloric acid solutions and by volume 1:5 with cover
Mixing in glass container, and 10% absolute ethyl alcohol is added, it is configured to reaction solution, is placed in 100 DEG C of water-bath a point reaction 1
Hour, room temperature is cooled down after taking-up rapidly, is concentrated under reduced pressure, blueberry anthocyanin aglycon hydrolyzate is made.
Step 5: column chromatography:By Sep-Pak C18 solid phase extraction columns on anthocyanidin aglycon hydrolyzate for removing aglycon
The recuding sugars of excessive hydrochloric acid and generation in hydrolyzate, applied sample amount are the 1/5 of column volume, the water being first acidified with 0.01% hydrochloric acid
It is eluted, elutes 4 times of column volumes, then eluted with the ethanol solution containing 0.01% hydrochloric acid of concentration 70%, collect 70% second
Alcohol eluen is concentrated under reduced pressure, and blueberry anthocyanin aglycon refined solution, high performance liquid chromatography detection the result is shown in Figure 1, gained aglycon is made
The uv-vis spectra analysis result of different monomers is shown in Fig. 2 to Fig. 6 in sample.
Step 6: chemical synthesis:By blueberry anthocyanin aglycon refined solution and 60% aqueous acetone solution by volume 1:40
The mixing in glass container with cover, and 10% absolute ethyl alcohol is added, it is configured to reaction solution, reaction solution pH is adjusted with hydrochloric acid
It is worth range 3.0, in 40 DEG C of heating water baths 7 days, is stirred daily during reaction 3 times, utilize high performance liquid chromatography (480nm) prison
Reaction process is surveyed, after reaction, is concentrated under reduced pressure, after dry, pyranoid form anthocyanidin aglycon is made, is surveyed through high performance liquid chromatography
Its purity is 67.5%, the high performance liquid chromatography detection result for obtaining sample is shown in Fig. 7, different monomers in gained pyrans sample
Uv-vis spectra analysis result is shown in that Fig. 8 to Figure 12, the High Performance Liquid Chromatography/Mass Spectrometry testing result of gained monomer are shown in Figure 13 to figure
17。
Embodiment 2
Step 1: extraction:Homogenate is made in fresh Blueberry raw material after crushing, is added in glass container with cover, with
1:65% ethanol solution is added in 3 volume ratio in being homogenized to Blueberry, with salt acid for adjusting pH value 2.5, stir 0.5 hour
Afterwards, black out impregnates 48 hours at room temperature;Extracting solution is filtered out, residue extracts 3 times again;
Step 2: extraction:Extracting solution after reduced pressure is poured into separatory funnel, liquid liquid extraction is carried out with ethyl acetate
It takes, volume ratio presses extracting solution:Ethyl acetate is 1:3, black out extraction 3 times at room temperature, the time is 24 hours/time, first will every time
Ester layer is poured out through top, then water layer is collected by lower section spare;
Step 3: column chromatography:Aqueous fraction anthocyanidin extraction solution is packed into AB-8 macroporous resin columns, single by wet method
Loading volume is the 1/12 of resin volume, first pillar is rinsed with the deionized water that 0.03% hydrochloric acid is acidified, for removing in sample
The water-soluble impurity such as reduced sugar, albumen, organic acid after eluting 5 times of column volumes, then with concentration 35% contains 0.03% hydrochloric acid
Ethanol solution elutes, and collects 35% ethanol eluate, is concentrated under reduced pressure, and blueberry anthocyanin refined solution is made;
Step 4: sour water solution:By blueberry anthocyanin refined solution and 2.5mol/L hydrochloric acid solutions and by volume 1:4 with cover
Mixing in glass container, and 20% absolute ethyl alcohol is added, it is configured to reaction solution, is placed in 95 DEG C of water-bath a point reaction
1.5 hours, room temperature is cooled down after taking-up rapidly, is concentrated under reduced pressure, blueberry anthocyanin aglycon hydrolyzate is made;
Step 5: column chromatography:By AB-8 macroreticular resins on anthocyanidin aglycon hydrolyzate, for removing in aglycon hydrolyzate
Excessive hydrochloric acid and the recuding sugars of generation, applied sample amount are the 1/5 of column volume, and the water being first acidified with 0.03% hydrochloric acid is eluted,
4 times of column volumes are eluted, then are eluted with the ethanol solution containing 0.03% hydrochloric acid of concentration 80%, 80% ethanol eluate is collected,
It is concentrated under reduced pressure, blueberry anthocyanin aglycon refined solution is made;
Step 6: chemical synthesis:By blueberry anthocyanin aglycon refined solution and 70% aqueous acetone solution by volume 1:50
The mixing in glass container with cover, and 20% absolute ethyl alcohol is added, it is configured to reaction solution, reaction solution pH is adjusted with hydrochloric acid
It is worth range 3.5, in 45 DEG C of heating water baths 5 days, is stirred daily during reaction 3 times, utilize high performance liquid chromatography (480nm) prison
Reaction process is surveyed, after reaction, is concentrated under reduced pressure, after dry, pyranoid form anthocyanidin aglycon is made, is surveyed through high performance liquid chromatography
It is 62.8% to obtain its purity.
Claims (5)
1. a kind of preparation method of pyranoid form anthocyanidin aglycon, it is characterised in that:Preparation method is as described below:
Step 1: extraction:Homogenate is made in Blueberry raw material after crushing, with 1:3-1:During 5 volume ratio is homogenized to fruit
The ethanol solution of 60-80% is added, adjusting pH value is 1.0-3.0, and after stirring 0.5 hour, it is small to impregnate 24-72 for black out at room temperature
When;Extracting solution is filtered out, residue extracts 2-3 times again;
Step 2: extraction:Extracting solution after reduced pressure is subjected to liquid-liquid extraction with ethyl acetate, volume ratio presses extracting solution:Second
Acetoacetic ester is 1:2-1:4, black out extraction 2-3 times at room temperature, the time is 24 hours/time, and it is spare to collect water layer anthocyanidin part;
Step 3: column chromatography:Water layer anthocyanidin obtained in step 2 is partially loaded macroporous resin column, single loading volume is
The 1/8-1/12 of resin volume first rinses pillar with deionized water, then with the hydrochloric acid containing 0.01-0.05% of concentration 35-45%
Ethanol solution elutes, and collects the ethanol eluate of 35-45%, is concentrated under reduced pressure, and blueberry anthocyanin refined solution is made;
Step 4: sour water solution:Blueberry anthocyanin refined solution obtained in step 3 and 2.5-4.0mol/L hydrochloric acid solutions are pressed into body
Product ratio 1:4-1:8 mixings, and the absolute ethyl alcohol of 10-20% is added, heating water bath 1-1.5 hours at 95-100 DEG C, after taking-up
Rapid cooling room temperature, is concentrated under reduced pressure, blueberry anthocyanin aglycon hydrolyzate is made;
Step 5: column chromatography:By solid phase extraction column or upper macroreticular resin on anthocyanidin aglycon hydrolyzate obtained in step 4
Column, applied sample amount are the 1/3-1/5 of column volume, are first eluted with deionized water, elute 3-5 times of column volume, then with concentration 60-
The ethanol solution of 80% hydrochloric acid containing 0.01-0.05% elutes, and collects the ethanol eluate of 60-80%, is concentrated under reduced pressure, and indigo plant is made
Certain kind of berries anthocyanidin aglycon refined solution;
Step 6: chemical synthesis:By the aqueous acetone solution of blueberry anthocyanin aglycon refined solution and 50-80% obtained in step 5
By volume 1:30-1:50 mixings, and the absolute ethyl alcohol of 10-20% is added, adjusting reacting solution pH value range with hydrochloric acid exists
Between 1.5-4.5, heating water bath 3-8 days at 30-55 DEG C, after reaction, reaction solution is through being concentrated under reduced pressure, and after dry, is made pure
Degree is the pyranoid form anthocyanidin aglycon of 60-70%.
2. a kind of preparation method of pyranoid form anthocyanidin aglycon according to claim 1, it is characterised in that:The step
Blueberry raw material described in one is made of blueberry fresh fruit or blueberry freeze fruit or blueberry powder or blueberry pomace.
3. a kind of preparation method of pyranoid form anthocyanidin aglycon according to claim 1, it is characterised in that:The step
The condition of reduced pressure in two to step 6 is:40-55 DEG C of temperature range, vacuum degree<0.09MPa, final volume reaches after concentration
For the 1/5-1/10 of original solution volume.
4. a kind of preparation method of pyranoid form anthocyanidin aglycon according to claim 1, it is characterised in that:The step
Three and step 5 in one kind in model Amberlite XAD-7HP of big pore resin, AB-8, NKA-9 and D101;Step
The model SEP-PAK C of solid phase extraction column described in rapid five18。
5. a kind of preparation method of pyranoid form anthocyanidin aglycon according to claim 1, it is characterised in that:The step
Dried forms are vacuum freeze drying in six, and drying condition is:- 45 DEG C to -55 DEG C of temperature range, vacuum degree<50Pa, time
24-48h。
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CN109393482A (en) * | 2018-12-07 | 2019-03-01 | 吉林大学 | A kind of blueberry pyrans anthocyanidin aglycon microcapsules and preparation method |
CN113549515A (en) * | 2021-07-23 | 2021-10-26 | 暨南大学 | Color-protecting fermentation method of anthocyanin-containing fruit wine |
WO2022172170A1 (en) * | 2021-02-09 | 2022-08-18 | Universidade Do Porto | Process for extraction and hemi-synthesis of pyranoanthocyanins and skincare cosmetic formulations containing them |
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CN109393482A (en) * | 2018-12-07 | 2019-03-01 | 吉林大学 | A kind of blueberry pyrans anthocyanidin aglycon microcapsules and preparation method |
WO2022172170A1 (en) * | 2021-02-09 | 2022-08-18 | Universidade Do Porto | Process for extraction and hemi-synthesis of pyranoanthocyanins and skincare cosmetic formulations containing them |
CN113549515A (en) * | 2021-07-23 | 2021-10-26 | 暨南大学 | Color-protecting fermentation method of anthocyanin-containing fruit wine |
CN113549515B (en) * | 2021-07-23 | 2023-11-03 | 暨南大学 | Color protection fermentation method of anthocyanin-containing fruit wine |
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