CN101353362B - Extraction method of cyaniding 3-0-glucoside - Google Patents
Extraction method of cyaniding 3-0-glucoside Download PDFInfo
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Abstract
The invention discloses a method for extracting cyanidin 3-O-glucoside, which comprises the following steps that: (1) extraction: an extraction is executed by adding water or aqueous acid in black soybean hull, etc., which are served as raw materials; (2) after being absorbed by macroporous resin, gradient elution is carried out by using water and an alcohol water solution and then the components rich in cyanidin 3-O-glucoside are collected and concentrated in a depressurized way so as to obtain concentrates; (3) the concentrates are dispersed into the water so as to carry out absorbing by polyamide resin; then, the gradient elution is carried out by using the water and the alcohol water solution and the components rich in cyanidin 3-O-glucoside are collected, concentrated in a depressurized way and dried; (4) Toyopearl volume exclusion-chromatography column-chromatography is carried out and then the cyanidin 3-O-glucoside is obtained. In the method of the invention, the extracts of cyanidin 3-O-glucoside in different contents ranging from 20 to 98 percent can be prepared, thereby enabling the cyanidin 3-O-glucoside to be industrially produced and laying the first stone for further developing and utilizing the extracts of cyanidin 3-O-glucoside.
Description
Technical field
The present invention relates to a kind of extracting method of cyaniding 3-0-glucoside.
Background technology
Cyaniding 3-0-glucoside (Cyanidin-3-O-glucoside is hereinafter to be referred as C3G) is a most representative compound in natural novel pigment-anthocyanidin, is to be the flavonoid class composition of parent nucleus with the flavones.This compounds polarity is big, and is water-soluble very good, is soluble in methyl alcohol, ethanol, the acetone.Be insoluble in the non-polar solvents such as chloroform, ether.Anthocyanidin is to light, thermo-responsive, and heating can be destroyed; Stable in sour environment, to meet alkali and become hyacinthine, chance iron, aluminium then become gray purple.Meeting plumbic acetate reagent can precipitate, and can is 3 apparent bright-coloured roses when following at pH by charcoal absorption.PH be 7 above colors by red purpling look, strengthen color from light to dark with pH, be to become atropurpureus more than 13 at pH.This compound is distributed widely in the multiple black whole food, as black rice, and Testa sojae atricolor, purple Radix Dauci Sativae, purple corn and black currant or the like.Research recently gives special attention to Cyanidin-3-glucoside, is that not only it is widely distributed, and it possesses the advantage proterties of anthocyanidin to the human health function.Serafino etc.
[1]Discover that the processing of Cyanidin-3-glucoside brings out the melanocytoma cytodifferentiation with dosage and time dependent mode.Fimognari research
[2]The ability of Cyanidin-3-glucoside to the apoptotic ability of inducing the T2 lymphoblastoid and cell death inducing and differentiation in HL260 promyelocyte white corpuscle.Cyanidin in 2 systems-equal cell death inducing of 3-glucoside, the HL260 cell is more insensitive than T2 class lymph protoblast.The most outstanding physiological function of Cyanidin-3-glucoside is exactly to have very strong antioxygenation, field, Japanese scholar Tianjin etc.
[3]Discover C3G in the presence of free radical generating agent (AMVN), can produce meta-bolites on the one hand, can produce the Protocatechuic Acid of energy Mulberry Extract simultaneously, thereby think that C3G has dual antioxygenation with inhibited oxidation ability.In addition, it has the improvement effect to eyesight, and the effect of gathering of obvious inhibition weight increase and body fat tissue can be arranged high fat diet, but to normal meals group no significant difference
[4]The content of cyaniding 3-0-glucoside is 1-20% than hanging down in the plant milk extract that contains cyaniding 3-0-glucoside of Xiao Shouing in the market.
Reference:
[1] Takahashi R, Ohmori R.Antioxidant activities of black and yellow soybeans against lowdensity lipoprotein oxidation.J Agric Food Chem.2005,53 (11): 4578-4582. (black soya bean and soya bean suppress the anti-oxidant activity [J] of low-density lipoprotein. the agricultural food product chemistry)
[2] Lin Xiaoxia, Zhu Shoumin. Chinese medicine anthocyan composition anticancer research progress [J]. CHINA JOURNAL OF CHINESE MATERIA MEDICA, 2005,30 (15): 1147-1150.
[3] Xu Lu, Zheng Jianxian. the research overview of Vaccinium myrtillus L. anthocyanogen [J]. Food Additives Used in China, 2005,4:43-47.
[4] Pang Zhishen. anthocyanogen research overview [J]. Beijing agricultural sciences, 2000,18 (5): 37-42.
Summary of the invention
The extracting method that the purpose of this invention is to provide a kind of cyaniding 3-0-glucoside.
Technical scheme of the present invention is summarized as follows:
A kind of extracting method of cyaniding 3-0-glucoside comprises the steps:
(1) extract, the method for extraction is a kind of of following step:
1. really be raw material with Testa sojae atricolor, black rice, purple Radix Dauci Sativae, purple corn palpus, purple corn skin, the Qarnet grain of rice, purple corn rod, Rhizoma Dioscoreae esculentae, mulberry fruit fruit, blue berry, Vaccinium myrtillus L. or indigo, add described raw materials quality 3-12 water or aqueous acid doubly and be the extraction solvent, extract 1-6 time at 20-50 ℃, each 1-8 hour, cross the 80-120 mesh sieve, get extracting solution, the concentration of volume percent of the acid in the described aqueous acid is 1%～5%;
2. with Testa sojae atricolor, black rice, purple Radix Dauci Sativae, purple corn must, the purple corn skin, the Qarnet grain of rice, the purple corn rod, Rhizoma Dioscoreae esculentae, the mulberry fruit fruit, blue berry, Vaccinium myrtillus L. or indigo really are raw material, add described raw materials quality 3-12 concentration of volume percent doubly and be 10%～95% aqueous ethanolic solution or methanol aqueous solution or glycolic acid aqueous solution or the methanolic acid aqueous solution for extracting solvent, extract 1-6 time at 20-50 ℃, each 1-8 hour, cross the 80-120 mesh sieve, in temperature≤60 ℃, vacuum tightness is that 0.06～0.08MPa is evaporated to pol 2-40, obtain extract, is that 1: 1～10 ratio is dispersed in the water with described extract with mass ratio, and the concentration of volume percent of the acid in the described aqueous acid is 1%～5%;
(2) product that described step (1) is obtained is through macroporous resin adsorption, water and concentration of volume percent are that 10%～95% aqueous ethanolic solution or water and concentration of volume percent are 10%～95% methanol aqueous solution gradient elution, the component of cyaniding 3-0-glucoside is rich in collection, concentrating under reduced pressure, pol is 10～40 enriched material;
(3) be 1 with described enriched material in mass ratio: the ratio of 3-5 is dispersed to carries out polyamide resin absorption in the water, water and concentration of volume percent are that the aqueous ethanolic solution of 5%-75% or water and concentration of volume percent are the methanol aqueous solution gradient elution of 5%-75%, the component of cyaniding 3-0-glucoside is rich in collection, concentrating under reduced pressure, to pol be 10-40, drying, the efficient part of cyaniding 3-0-glucoside;
(4) efficient part with described cyaniding 3-0-glucoside carries out Toyopearl volume-exclusion chromatography column chromatography purification, the water removal of contamination, methanol aqueous solution with volume percent 20%-40% carries out the isoconcentration wash-out again, with the pure product of cyaniding 3-0-glucoside product in contrast, the component of cyaniding 3-0-glucoside is rich in collection, with the elutriant concentrating under reduced pressure, obtain the component that pol is 10-20, lyophilize obtains cyaniding 3-0-glucoside.
Described cyaniding 3-0-glucoside can also be carried out MCI gel filtration chromatography purifying, wash with water and remove decon, methyl alcohol with volume percent 10%-30% carries out the isoconcentration wash-out again, with the pure product of cyaniding 3-0-glucoside product in contrast, the component of cyaniding 3-0-glucoside is rich in collection, with the elutriant concentrating under reduced pressure, obtain the component that pol is 10-20, lyophilize obtains the pure product of cyaniding 3-0-glucoside.
Step (1) is extracted preferably: with Testa sojae atricolor, black rice, purple Radix Dauci Sativae, purple corn palpus, purple corn skin, the Qarnet grain of rice, purple corn rod, Rhizoma Dioscoreae esculentae, mulberry fruit fruit, blue berry, Vaccinium myrtillus L. or indigo really is raw material, the aqueous acid that adds 10 times of described raw materials quality is for extracting solvent, extract 3-5 time at 40-45 ℃, each 4-6 hour, cross 100 mesh sieves, get extracting solution, the concentration of volume percent of the acid in the described aqueous acid is 1%～3%.
Step (1) is extracted: with Testa sojae atricolor, black rice, purple Radix Dauci Sativae, purple corn must, the purple corn skin, the Qarnet grain of rice, the purple corn rod, Rhizoma Dioscoreae esculentae, the mulberry fruit fruit, blue berry, Vaccinium myrtillus L. or indigo really are raw material, the concentration of volume percent that adds 10 times of described raw materials quality is that 40%～60% glycolic acid aqueous solution is for extracting solvent, extract 3-5 time at 20-30 ℃, each 4-6 hour, cross 100 mesh sieves, in temperature≤60 ℃, vacuum tightness is that 0.06～0.08MPa is evaporated to pol 2-40, obtain extract, is that 1: 4～5 ratio is dispersed in the water with described extract with mass ratio, and the concentration of volume percent of the acid in the described aqueous acid is 1%～3%.
Acid in the described aqueous acid is hydrochloric acid, sulfuric acid, phosphoric acid, acetate or citric acid.
The model of described macroporous resin is AB-8 type, HP20 type, HPD100 type, HPD100A type, HPD300 type, X-5 type, NKA-II type, D101 type or DA201 type.
Described Toyopearl resin is Toyopearl HW-40S, Toyopearl HW-40F, Toyopearl HW-40C, Toyopearl HW-50S, Toyopearl HW-50F, Toyopearl HW-55S, Toyopearl HW-55F, ToyopearlHW-65S, Toyopearl HW-65F, Toyopearl HW-75S or Toyopearl HW-75F.
Described MCI GEL resin is MCI GEL CHP20P, MCI GEL CHP5C or MCI GEL CHP2MG.
Because the extractive content of selling on the market that contains cyaniding 3-0-glucoside is relatively low, generally has only 1%-10%, and method provided by the invention can prepare the extract of cyaniding 3-0-glucoside of the different content of 20%-98%, make the extract of the cyaniding 3-0-glucoside of 20%-98% different content can reach industrialization production, for the further development and use of the cyaniding 3-0-glucoside extract of 20%-98% different content lay the foundation.
Description of drawings
Fig. 1 is that the polyamide layer TLC of cyaniding 3-0-glucoside of the present invention detects figure
Fig. 2 is the liquid phase analysis collection of illustrative plates of cyaniding 3-0-glucoside of the present invention.
Fig. 3 is the ESI-MS collection of illustrative plates of cyaniding 3-0-glucoside of the present invention.
Embodiment
The molecular structure of cyaniding 3-0-glucoside is as follows:
The present invention is further illustrated below in conjunction with specific embodiment.
Embodiment 1
Cyaniding 3-0-glucoside content HPLC detection method below 90%:
Chromatographic column: C-18 250 * 4.6mm
Detect wavelength: 520nm
Flow velocity: 1.0ml/min
Moving phase: A:5% aqueous formic acid
B: methyl alcohol
Sample dissolves with 1% hydrochloric acid methanol
The HPLC detection method of 98% cyaniding 3-0-glucoside:
Chromatographic column: YMC C-18 (250 * 4.6mm)
Detect wavelength: 520nm
Flow velocity: 0.8ml/min
Sample size: 10ul
Column temperature: 30 ℃
Moving phase: A: contain 0.5% phosphate aqueous solution
B: water: acetonitrile: Glacial acetic acid: phosphoric acid=50: 48.5: 1: 0.5
Gradient such as following table
(1) extraction: the 50 ℃ of warm lixiviates of water normal pressure that add 5000g in the 500g Testa sojae atricolor are got 5 times, and extraction time was respectively 5,4,3,2,1 hours, filter, and the order number of filter screen is 120, and extracting solution merges filtration, and the order number of filter screen is 100, and getting supernatant liquor is extracting solution;
(2) macroporous resin adsorption is separated: will (1) middle extracting solution through HP20 type macroporous resin adsorption, water, concentration of volume percent are 10%, 30%, 50%, 70%, 95% aqueous ethanolic solution gradient elution, every 250ml receives volume as one, detect by thin-layer chromatography method and binding analysis type HPLC, the component of cyaniding 3-0-glucoside is rich in collection, with its merging, in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 40, gets the enriched substance of cyaniding 3-0-glucoside; The content of cyaniding 3-0-glucoside is 31.7%;
(3) polyamide resin separates: the enriched substance of the cyaniding 3-0-glucoside that macroporous resin adsorption obtains after separating is dispersed in the water (1: 4) and carries out polyamide resin and separate, water, concentration of volume percent is 5%, 30%, 50%, 75% aqueous ethanolic solution, by method and binding analysis type HPLC detections such as thin-layer chromatographies, the component of cyaniding 3-0-glucoside is rich in collection, with elutriant in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 10, dry, get the enriched substance of cyaniding 3-0-glucoside, the content of cyaniding 3-0-glucoside is 54.3%;
Thin-layer chromatography detection method described in the step (3) adopts polyamide layer, and launching solvent is that volume ratio is 4: 1 a methanol-water, and developer is that concentration expressed in percentage by weight is 5% iron trichloride ethanolic soln, with the cyaniding 3-0-glucoside standard control.
(4) Toyopearl resin column chromatographic separation: the component that will be rich in cyaniding 3-0-glucoside after will separating by polymeric amide is carried out Toyopearl HW-40S resin column chromatography, wash with water and remove decon, be 20% with volume percent again, 30%, 40% methanol aqueous solution gradient elution, every 50ml receives volume as one, by method and binding analysis type HPLC detections such as thin-layer chromatographies, with the pure product of cyaniding 3-0-glucoside product in contrast, the component of cyaniding 3-0-glucoside is rich in collection, and with it in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 15, and measure with the method for embodiment 1: the content of cyaniding 3-0-glucoside is 77.3%.
Embodiment 4
(1) extraction: the 40 ℃ of warm lixiviates of sour water normal pressure that add 5000g in the 500g Testa sojae atricolor are got 5 times, and extraction time was respectively 6,5,4,4,4 hours, filter, and the order number of filter screen is 100, and extracting solution merges filtration, and the order number of filter screen is 100, and getting supernatant liquor is extracting solution; (aqueous acid is that concentration expressed in percentage by volume is 1% sulfuric acid)
(2)-(4) with embodiment 3;
The product of embodiment 3 preparations is carried out purifying through the MCI gel filtration chromatography, wash with water and remove decon, methyl alcohol with volume percent 30% carries out wash-out again, every 50ml receives volume as one, detect by thin-layer chromatography method and binding analysis type HPLC, with the pure product of cyaniding 3-0-glucoside product in contrast, the component of cyaniding 3-0-glucoside is rich in collection, with elutriant in temperature≤60 ℃, vacuum tightness is the 0.06-0.08MPa concentrating under reduced pressure, obtain pol and be 20 component, lyophilize obtains cyaniding 3-0-glucoside (360mg).
Cyaniding 3-0-glucoside is the dark red powder, and polyamide layer launches with methanol-water (4: 1), and Rf is that 0.5,5% iron trichloride ethanolic soln shows single blue spot (see figure 1).Utilize standard substance (purchase of Norway Polyphenol company) to demarcate according to the method for embodiment 2, measuring the cyaniding 3-0-glucoside samples contg is 98% (Fig. 2).Provided quasi-molecular ion peak [M] among the positively charged ion ESI-MS
+449 (Fig. 3) have reaffirmed the structure of separating the cyaniding 3-0-glucoside that obtains according to aforesaid method.
(1) extract: the 45 ℃ of warm lixiviates of aqueous acid (hydrochloric acid that contains volume ratio 3%) normal pressure that add 1500g in the 500g black rice are got 3 times, and each 4 hours, filter, the order number of filter screen is 80, the extracting solution merging is left standstill, and gets supernatant liquor;
(2) macroporous resin adsorption is separated: extracting solution in (1) is adsorbed through macroporous resin AB-8, water, concentration of volume percent are 10%, 30%, 50%, 70% aqueous ethanolic solution gradient elution, every 250ml receives volume as one, detect by thin-layer chromatography method and binding analysis type HPLC, the component of cyaniding 3-0-glucoside is rich in collection, with its merging, in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 40, gets the enriched substance of cyaniding 3-0-glucoside; The content of cyaniding 3-0-glucoside is 41.2%;
(3) polyamide resin separates: the enriched substance of the cyaniding 3-0-glucoside that macroporous resin adsorption obtains after separating is dispersed in the water (1: 4) and carries out polyamide resin and separate, water, concentration of volume percent is 5%, 30%, 50%, 75% aqueous ethanolic solution gradient elution, elutriant detects by thin-layer chromatography method and binding analysis type HPLC, the component of cyaniding 3-0-glucoside is rich in collection, according to the content height of cyaniding 3-0-glucoside is different elutriant is divided into three components merging, respectively in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 10, dry, get the efficient part of cyaniding 3-0-glucoside, the content of cyaniding 3-0-glucoside is 68.6%;
(4) Toyopearl resin column chromatographic separation: the efficient part of cyaniding 3-0-glucoside is carried out ToyopearlHW-40F volume-exclusion chromatography column chromatography purification, wash with water and remove decon, be 20% with volume percent again, 30%, 40% methanol aqueous solution gradient elution, every 50ml receives volume as one, detect by thin-layer chromatography method and binding analysis type HPLC, with the pure product of cyaniding 3-0-glucoside product in contrast, the component of cyaniding 3-0-glucoside is rich in collection, and with it in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 20, the cyaniding 3-0-glucoside extract that obtains, cyaniding 3-0-glucoside extractive content are 78.1%.
Step (1)-step (4) is with embodiment 5;
(5) the MCI gel filtration chromatography carries out purifying: the product of embodiment 5 preparations is carried out MCI GEL CHP20P gel filtration chromatography purifying, wash with water and remove decon, methyl alcohol with volume percent 30% carries out wash-out again, every 50ml receives volume as one, detect by thin-layer chromatography method and binding analysis type HPLC, with the pure product of cyaniding 3-0-glucoside product in contrast, the component of cyaniding 3-0-glucoside is rich in collection, with elutriant in temperature≤60 ℃, vacuum tightness is the 0.06-0.08MPa concentrating under reduced pressure, obtain pol and be 20 component, lyophilize obtains cyaniding 3-0-glucoside (50mg).
Embodiment 7
(1) extract: the concentration of volume percent that the 500g Qarnet grain of rice adds 5000g is that 20 ℃ of warm lixiviates of aqueous ethanolic solution normal pressure of 10% are got 1 time, lixiviate 5 hours, filter, the order number of filter screen is 100, and extracting solution is in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 10, the enriched substance of cyaniding 3-0-glucoside, be that 1: 3 ratio is dispersed in the water with extract with mass ratio, left standstill 2 hours, and discarded precipitation;
(2) macroporous resin adsorption is separated: supernatant liquor adsorbs through macroporous resin HPD100 type, water, concentration of volume percent are 10%, 30%, 50%, 75%, 95% methanol aqueous solution gradient elution, every 250ml receives volume as one, detect by thin-layer chromatography method and binding analysis type HPLC, the component of cyaniding 3-0-glucoside is rich in collection, with its merging, in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 10, gets the enriched substance of cyaniding 3-0-glucoside;
(3) polyamide resin separates: the enriched substance of the cyaniding 3-0-glucoside that macroporous resin adsorption obtains after separating is dispersed in the water (weight ratio is 1: 3) and carries out polyamide resin and separate, water, concentration of volume percent is 5%, 20%, 50%, 75% methanol aqueous solution gradient elution, elutriant detects by thin-layer chromatography method and binding analysis type HPLC, the component of cyaniding 3-0-glucoside is rich in collection, with elutriant in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 40, get the enriched substance of cyaniding 3-0-glucoside, cyaniding 3-0-glucoside content is 34.9%.
With the raw material of purple corn skin, purple corn palpus, purple corn rod replacement present embodiment, the content that can obtain cyaniding 3-0-glucoside is 29.3%, 32.1%, 38.5%.
(1) extract: with purple Radix Dauci Sativae is raw material, the concentration of volume percent that adds 10 times of described raw materials quality is that 60% glycolic acid aqueous solution is for extracting solvent, extract 3 times at 20 ℃, each 6 hours, cross 100 mesh sieves, in temperature≤60 ℃, vacuum tightness is that 0.06～0.08MPa is evaporated to pol 40, obtains extract, is that 1: 5 ratio is dispersed in the water with described extract with mass ratio, acid in the described aqueous acid is phosphoric acid, and its concentration of volume percent is 1%;
(2)-(3) with embodiment 7;
(4) Toyopearl volume-exclusion chromatography purification: the component that will be rich in cyaniding 3-0-glucoside after step (1)-step (3) is separated is carried out Toyopearl HW-40C resin column chromatography, wash with water earlier and remove decon, be 20% with volume percent again, 30%, 40% methanol aqueous solution gradient elution, every 50ml receives volume as one, detect by thin-layer chromatography method and binding analysis type HPLC, with the pure product of cyaniding 3-0-glucoside product in contrast, the component of cyaniding 3-0-glucoside is rich in collection, and with it in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 10, and the cyaniding 3-0-glucoside extractive content that obtains is 83.2%.
With the raw material of purple corn skin, purple corn palpus, purple corn rod replacement present embodiment, the content that can obtain cyaniding 3-0-glucoside is 71.7%, 74.4%, 81.7%.
Embodiment 9
(1) extract: with the black rice is raw material, the concentration of volume percent that adds 10 times of described raw materials quality is that 40% glycolic acid aqueous solution is for extracting solvent, extract 5 times at 30 ℃, each 4 hours, cross 100 mesh sieves, in temperature≤60 ℃, vacuum tightness is that 0.06～0.08MPa is evaporated to pol 2, obtains extract, is that 1: 4 ratio is dispersed in the water with described extract with mass ratio, acid in the described aqueous acid is hydrochloric acid, and its concentration of volume percent is 3%;
(2)-(4) with embodiment 8;
(5) the MCI gel filtration chromatography carries out purifying: the component that contains cyaniding 3-0-glucoside that obtains in (4) is carried out MCI GEL column chromatography purification, wash with water and remove decon, methyl alcohol with volume percent 20% carries out wash-out again, every 50ml receives volume as one, detect by thin-layer chromatography method and binding analysis type HPLC, with the pure product of cyaniding 3-0-glucoside product in contrast, the component of cyaniding 3-0-glucoside is rich in collection, with elutriant in temperature≤60 ℃, vacuum tightness is the 0.06-0.08MPa concentrating under reduced pressure, obtain pol and be 10 component, lyophilize obtains cyaniding 3-0-glucoside (10mg).
Raw material with purple corn skin, purple corn palpus, purple corn rod replacement present embodiment can obtain cyaniding 3-0-glucoside.
(1) extract: the concentration of volume percent that the purple Radix Dauci Sativae of 500g adds 6000g is that 30 ℃ of warm lixiviates of aqueous ethanolic solution (containing 5% Glacial acetic acid) normal pressure of 10% are got 1 time, 800 mesh sieves are crossed in lixiviate 5 hours, get extracting solution, in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, and pol is 2, is that 1: 10 ratio is dispersed in the water with described extract with mass ratio, left standstill 2 hours, and discarded precipitation, get supernatant liquor;
(2) macroporous resin adsorption is separated: supernatant liquor adsorbs through macroporous resin HPD100A type, water, concentration of volume percent are 10%, 30%, 50%, 70%, 95% aqueous ethanolic solution gradient elution, every 250ml receives volume as one, detect by thin-layer chromatography method and binding analysis type HPLC, the component of cyaniding 3-0-glucoside is rich in collection, with its merging, in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 40, gets the enriched substance of cyaniding 3-0-glucoside;
(3) polyamide resin separates: the enriched substance of the cyaniding 3-0-glucoside that macroporous resin adsorption obtains after separating is dispersed in the water (weight ratio is 1: 5) and carries out polyamide resin and separate, water, concentration of volume percent is 5%, 30%, 50%, 75% aqueous ethanolic solution, detect by thin-layer chromatography method and binding analysis type HPLC, the component of cyaniding 3-0-glucoside is rich in collection, with elutriant in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 10, get the enriched substance of cyaniding 3-0-glucoside, cyaniding 3-0-glucoside content is 21.2%;
(4) Toyopearl resin column chromatographic separation: the component that will be rich in cyaniding 3-0-glucoside after step (1)-step (3) is separated is carried out Toyopearl HW-50S resin column chromatography, wash with water earlier and remove decon, be 20% with volume percent again, 30%, 40% methanol aqueous solution gradient elution, every 50ml receives volume as one, detect by thin-layer chromatography method and binding analysis type HPLC, with the pure product of cyaniding 3-0-glucoside product in contrast, the component of cyaniding 3-0-glucoside is rich in collection, and with it in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 20, and the cyaniding 3-0-glucoside extractive content that obtains is 53.2%.
(5) the MCI gel filtration chromatography carries out purifying: the component that contains cyaniding 3-0-glucoside that obtains in (4) is carried out MCI GEL column chromatography purification, wash with water and remove decon, methyl alcohol with volume percent 10% carries out wash-out again, every 50ml receives volume as one, detect by thin-layer chromatography method and binding analysis type HPLC, with the pure product of cyaniding 3-0-glucoside product in contrast, the component of cyaniding 3-0-glucoside is rich in collection, with elutriant in temperature≤60 ℃, vacuum tightness is the 0.06-0.08MPa concentrating under reduced pressure, obtain pol and be 20 component, lyophilize obtains cyaniding 3-0-glucoside (5mg).The MCI gel column is selected MCI GEL CHP5C for use.
Embodiment 11
(1) extract: the concentration of volume percent that the root of 500g Rhizoma Dioscoreae esculentae adds 5000g is that 50 ℃ of warm lixiviates of aqueous ethanolic solution (containing 1% sulfuric acid) normal pressure of 95% are got 3 times, lixiviate 5 hours, filter, extracting solution merges to leave standstill to temperature and is lower than 50 degree, abandon precipitation, get supernatant liquor, in temperature≤60 ℃, vacuum tightness is that 0.06～0.08MPa is evaporated to nothing alcohol, and pol is 40, gets the enriched substance of cyaniding 3-0-glucoside, is that 1: 10 ratio is dispersed in the water with described enriched substance with mass ratio, left standstill 2 hours, and discarded precipitation, get supernatant liquor;
(2) macroporous resin adsorption is separated: supernatant liquor adsorbs through macroporous resin X-5, water, concentration of volume percent are 10%, 30%, 50%, 70%, 95% aqueous ethanolic solution gradient elution, every 250ml receives volume as one, detect by thin-layer chromatography method and binding analysis type HPLC, the component of cyaniding 3-0-glucoside is rich in collection, with its merging, in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 20, gets the enriched substance of cyaniding 3-0-glucoside;
(3) polyamide resin separates: the enriched substance of the cyaniding 3-0-glucoside that macroporous resin adsorption obtains after separating is dispersed in the water (1: 4) and carries out polyamide resin and separate, water, concentration of volume percent is 5%, 30%, 50%, 75% aqueous ethanolic solution, by method and binding analysis type HPLC detections such as thin-layer chromatographies, the component of cyaniding 3-0-glucoside is rich in collection, with elutriant in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 20, get the enriched substance of cyaniding 3-0-glucoside, cyaniding 3-0-glucoside content is 37.4%;
(4) Toyopearl resin column chromatographic separation: the component that will be rich in cyaniding 3-0-glucoside after step (1)-step (3) is separated is carried out Toyopearl HW-50F resin column chromatography, wash with water earlier and remove decon, be 20% with volume percent again, 30%, 40% methanol aqueous solution gradient elution, every 50ml receives volume as one, by method and binding analysis type HPLC detections such as thin-layer chromatographies, with the pure product of cyaniding 3-0-glucoside product in contrast, the component of cyaniding 3-0-glucoside is rich in collection, and with it in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 20, the cyaniding 3-0-glucoside extractive content difference 75.2% that obtains.
(5) the MCI gel filtration chromatography carries out purifying: the component that contains cyaniding 3-0-glucoside that obtains in (4) is carried out MCI GEL column chromatography purification, wash with water and remove decon, methyl alcohol with volume percent 40% carries out wash-out again, every 50ml receives volume as one, by method and binding analysis type HPLC detections such as thin-layer chromatographies, with the pure product of cyaniding 3-0-glucoside product in contrast, the component of cyaniding 3-0-glucoside is rich in collection, with elutriant in temperature≤60 ℃, vacuum tightness is the 0.06-0.08MPa concentrating under reduced pressure, obtain pol and be 20 component, lyophilize obtains cyaniding 3-0-glucoside (80mg).(model of present embodiment macroporous resin also can be selected NKA-II type or DA201 type for use) MCI gel column is selected MCI GEL CHP2MG for use.
(1) extract: the concentration of volume percent that the 500g mulberry fruit adds 1500g is that 30 ℃ of warm lixiviates of methanol aqueous solution (containing 1% hydrochloric acid) normal pressure of 60% are got 1 time, lixiviate 5 hours, filter, extracting solution is incorporated in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 20, gets the enriched substance of cyaniding 3-0-glucoside;
(2) macroporous resin adsorption is separated: will (1) middle cyaniding 3-0-glucoside extract with water-dispersion (weight ratio is 1: 4), left standstill 2 hours, discard precipitation, supernatant liquor adsorbs through macroporous resin HPD-300, water, concentration of volume percent is 10%, 30%, 50%, 95% aqueous ethanolic solution gradient elution, every 250ml accepts volume as one, detect by thin-layer chromatography method and binding analysis type HPLC, the component of cyaniding 3-0-glucoside is rich in collection, with its merging, in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 40, gets the enriched substance of cyaniding 3-0-glucoside;
(3) polyamide resin separates: the enriched substance of the cyaniding 3-0-glucoside that macroporous resin adsorption obtains after separating is dispersed in the water (1: 4) and carries out polyamide resin and separate, water, concentration of volume percent are 5%, 30%, 50%, 75% aqueous ethanolic solution, detect by thin-layer chromatography method and binding analysis type HPLC, the component of cyaniding 3-0-glucoside is rich in collection, with elutriant in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 10, gets the enriched substance of cyaniding 3-0-glucoside; Cyaniding 3-0-glucoside content is 49.2%;
(4) Toyopearl resin column chromatographic separation: the component that will be rich in cyaniding 3-0-glucoside after step (1)-step (3) is separated is carried out Toyopearl HW-55S resin column chromatography, wash with water earlier and remove decon, be 20% with volume percent again, 30%, 40%, the methanol aqueous solution gradient elution, every 50ml receives volume as one, by method and binding analysis type HPLC detections such as thin-layer chromatographies, with the pure product of cyaniding 3-0-glucoside product in contrast, the component of cyaniding 3-0-glucoside is rich in collection, and with it in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 20, the cyaniding 3-0-glucoside extractive content difference 82.2% that obtains.
(5) the MCI gel filtration chromatography carries out purifying: the component that contains cyaniding 3-0-glucoside that obtains in (4) is carried out MCI GEL column chromatography purification, wash with water and remove decon, methyl alcohol with volume percent 40% carries out wash-out again, every 50ml receives volume as one, by method and binding analysis type HPLC detections such as thin-layer chromatographies, with the pure product of cyaniding 3-0-glucoside product in contrast, the component of cyaniding 3-0-glucoside is rich in collection, with elutriant in temperature≤60 ℃, vacuum tightness is the 0.06-0.08MPa concentrating under reduced pressure, obtain pol and be 20 component, lyophilize obtains cyaniding 3-0-glucoside (55mg).
Embodiment 13
(1) extract: the concentration of volume percent of the bright product adding of 500g blueberry 6000g is that 70 ℃ of warm lixiviates of aqueous ethanolic solution normal pressure of 10% are got 1 time, lixiviate 5 hours, filter, extracting solution is incorporated in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 20, gets the enriched substance of cyaniding 3-0-glucoside.
(2) macroporous resin adsorption is separated: will (1) middle cyaniding 3-0-glucoside extract with water-dispersion (weight ratio is 1: 4), left standstill 2 hours, discard precipitation, supernatant liquor adsorbs through macroporous resin D-101, water, concentration of volume percent is 10%, 30%, 50%, 95% aqueous ethanolic solution gradient elution, every 250ml accepts volume as one, detect by thin-layer chromatography method and binding analysis type HPLC, the component of cyaniding 3-0-glucoside is rich in collection, with its merging, in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 40, gets the enriched substance of cyaniding 3-0-glucoside.
(3) polyamide resin separates: the enriched substance of the cyaniding 3-0-glucoside that macroporous resin adsorption obtains after separating is dispersed in the water (1: 4) and carries out polyamide resin and separate, water, concentration of volume percent are 5%, 30%, 50%, 75% aqueous ethanolic solution, detect by thin-layer chromatography method and binding analysis type HPLC, the component of cyaniding 3-0-glucoside is rich in collection, with elutriant in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 10, get the enriched substance of cyaniding 3-0-glucoside, content is 41.8%
(4) Toyopearl resin column chromatographic separation: the component that will be rich in cyaniding 3-0-glucoside after step (1)-step (3) is separated is carried out Toyopearl HW-55F resin column chromatography, wash with water earlier and remove decon, be 10% with volume percent again, 20%, 30%, 40%, 50% methanol aqueous solution gradient elution, every 50ml receives volume as one, by method and binding analysis type HPLC detections such as thin-layer chromatographies, with the pure product of cyaniding 3-0-glucoside product in contrast, the component of cyaniding 3-0-glucoside is rich in collection, and with it in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 20, the cyaniding 3-0-glucoside extractive content difference 75.2% that obtains.
(5) the MCI gel filtration chromatography carries out purifying: the component that contains cyaniding 3-0-glucoside that obtains in (4) is carried out MCI GEL column chromatography purification, wash with water and remove decon, methyl alcohol with volume percent 40% carries out wash-out again, every 50ml receives volume as one, by method and binding analysis type HPLC detections such as thin-layer chromatographies, with the pure product of cyaniding 3-0-glucoside product in contrast, the component of cyaniding 3-0-glucoside is rich in collection, with elutriant in temperature≤60 ℃, vacuum tightness is the 0.06-0.08MPa concentrating under reduced pressure, obtain pol and be 20 component, lyophilize obtains cyaniding 3-0-glucoside (110mg).
(1) extract: the concentration of volume percent that the 500g Vaccinium myrtillus L. adds 4000g is that 40 ℃ of warm lixiviates of methanol aqueous solution normal pressure of 10% are got 1 time, lixiviate 5 hours, filter, extracting solution is incorporated in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 10, gets the enriched substance of cyaniding 3-0-glucoside;
(2) macroporous resin adsorption is separated: will (1) middle cyaniding 3-0-glucoside extract with water-dispersion (weight ratio is 1: 1), left standstill 2 hours, discard precipitation, supernatant liquor adsorbs through macroporous resin NKA-II, water, concentration of volume percent is 10%, 30%, 50%, 70%, 95% methanol aqueous solution gradient elution, every 250ml accepts volume as one, detect by thin-layer chromatography method and binding analysis type HPLC, the component of cyaniding 3-0-glucoside is rich in collection, with its merging, in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 15, gets the enriched substance of cyaniding 3-0-glucoside;
(3) polyamide resin separates: the enriched substance of the cyaniding 3-0-glucoside that macroporous resin adsorption obtains after separating is dispersed in the water (weight ratio is 1: 4) and carries out polyamide resin and separate, water, concentration of volume percent is 5%, 30%, 50%, 75% aqueous ethanolic solution, by method and binding analysis type HPLC detections such as thin-layer chromatographies, the component of cyaniding 3-0-glucoside is rich in collection, with elutriant in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 10, get the enriched substance of cyaniding 3-0-glucoside, cyaniding 3-0-glucoside content is 39.1%;
(4) Toyopearl resin column chromatographic separation: the component that will be rich in cyaniding 3-0-glucoside after step (1)-step (3) is separated is carried out Toyopearl HW-65S resin column chromatography, wash with water earlier and remove decon, be 10% with volume percent again, 20%, 30%, 40%, 50% methanol aqueous solution gradient elution, every 50ml receives volume as one, by method and binding analysis type HPLC detections such as thin-layer chromatographies, with the pure product of cyaniding 3-0-glucoside product in contrast, the component of cyaniding 3-0-glucoside is rich in collection, and with it in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 20, the cyaniding 3-0-glucoside extractive content difference 73.7% that obtains.
(5) the MCI gel filtration chromatography carries out purifying: the component that contains cyaniding 3-0-glucoside that obtains in (4) is carried out MCI GEL column chromatography purification, wash with water and remove decon, methyl alcohol with volume percent 40% carries out wash-out again, every 50ml receives volume as one, by method and binding analysis type HPLC detections such as thin-layer chromatographies, with the pure product of cyaniding 3-0-glucoside product in contrast, the component of cyaniding 3-0-glucoside is rich in collection, with elutriant in temperature≤60 ℃, vacuum tightness is the 0.06-0.08MPa concentrating under reduced pressure, obtain pol and be 20 component, lyophilize obtains cyaniding 3-0-glucoside (170mg).
(1) extract: the concentration of volume percent that the 500g indigo really adds 3000g is that 40 ℃ of warm lixiviates of methanol aqueous solution (containing 5% citric acid) normal pressure of 95% are got 3 times, lixiviate 3 hours, filter, extracting solution is incorporated in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 40, gets the enriched substance of cyaniding 3-0-glucoside;
(2) macroporous resin adsorption is separated: will (1) middle cyaniding 3-0-glucoside extract with water-dispersion (weight ratio is 1: 10), left standstill 2 hours, discard precipitation, supernatant liquor adsorbs through macroporous resin HPD-300, water, concentration of volume percent is 10%, 30%, 50%, 70%, 95% aqueous ethanolic solution gradient elution, every 250ml accepts volume as one, by method and binding analysis type HPLC detections such as thin-layer chromatographies, the component of cyaniding 3-0-glucoside is rich in collection, with its merging, in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 30, gets the enriched substance of cyaniding 3-0-glucoside;
(3) polyamide resin separates: the enriched substance of the cyaniding 3-0-glucoside that macroporous resin adsorption obtains after separating is dispersed in the water (weight ratio is 1: 4) and carries out polyamide resin and separate, water, concentration of volume percent is 5%, 30%, 50%, 75% aqueous ethanolic solution, by method and binding analysis type HPLC detections such as thin-layer chromatographies, the component of cyaniding 3-0-glucoside is rich in collection, with elutriant in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 10, get the enriched substance of cyaniding 3-0-glucoside, cyaniding 3-0-glucoside content is 54.7%;
(4) Toyopearl resin column chromatographic separation: the component that will be rich in cyaniding 3-0-glucoside after step (1)-step (3) is separated is carried out Toyopearl HW-65F resin column chromatography, wash with water earlier and remove decon, be 10% with volume percent again, 20%, 30%, 40%, 50% methanol aqueous solution gradient elution, every 50ml receives volume as one, by method and binding analysis type HPLC detections such as thin-layer chromatographies, with the pure product of cyaniding 3-0-glucoside product in contrast, the component of cyaniding 3-0-glucoside is rich in collection, and with it in temperature≤60 ℃, vacuum tightness is 0.06～0.08MPa concentrating under reduced pressure, pol is 20, the cyaniding 3-0-glucoside extractive content difference 89.2% that obtains; (model of the Toyopearl resin of present embodiment also can be selected Toyopearl HW-75S or Toyopearl HW-75F for use)
(5) the MCI gel filtration chromatography carries out purifying: the component that contains cyaniding 3-0-glucoside that obtains in (4) is carried out MCI GEL column chromatography purification, wash with water and remove decon, methyl alcohol with volume percent 40% carries out wash-out again, every 50ml receives volume as one, by method and binding analysis type HPLC detections such as thin-layer chromatographies, with the pure product of cyaniding 3-0-glucoside product in contrast, the component of cyaniding 3-0-glucoside is rich in collection, with elutriant in temperature≤60 ℃, vacuum tightness is the 0.06-0.08MPa concentrating under reduced pressure, obtain pol and be 20 component, lyophilize obtains cyaniding 3-0-glucoside (107mg).
(1) extraction: the 40 ℃ of warm lixiviates of water normal pressure that add 1500g in the 500g Testa sojae atricolor are got 6 times, and extraction time was respectively 4,4,4,3,2,1 hours, filter, and the order number of filter screen is 80, and extracting solution merges filtration, and getting supernatant liquor is extracting solution;
(2)-(4) with embodiment 3.
Embodiment 17
(1) extraction: the 20 ℃ of warm lixiviates of water normal pressure that add 6000g in the 500g Testa sojae atricolor are got 1 time, and extraction time is 8 hours, filter, and the order number of filter screen is 100, and extracting solution merges filtration, and getting supernatant liquor is extracting solution;
(3)-(4) with embodiment 3.
(1) extract: the 45 ℃ of warm lixiviates of aqueous acid (hydrochloric acid that contains volume ratio 1%) normal pressure that add 6000g in the 500g black rice are got 3 times, and each 4 hours, filter, the order number of filter screen is 80, the extracting solution merging is left standstill, and gets supernatant liquor;
(3)-(4) with embodiment 5.
Embodiment 19
(1) extract: the 45 ℃ of warm lixiviates of aqueous acid (citric acid that contains volume ratio 5%) normal pressure that add 6000g in the 500g black rice are got 3 times, and each 4 hours, filter, the order number of filter screen is 80, the extracting solution merging is left standstill, and gets supernatant liquor;
(3)-(4) with embodiment 5.
Claims (7)
1. the extracting method of a cyaniding 3-0-glucoside is characterized in that comprising the steps:
(1) extract, the method for extraction is a kind of of following step:
1. really be raw material with Testa sojae atricolor, black rice, purple Radix Dauci Sativae, purple corn palpus, purple corn skin, the Qarnet grain of rice, purple corn rod, Rhizoma Dioscoreae esculentae, mulberry fruit fruit, blue berry, Vaccinium myrtillus L. or indigo, add described raw materials quality 3-12 water or aqueous acid doubly and be the extraction solvent, extract 1-6 time at 20-50 ℃, each 1-8 hour, cross the 80-120 mesh sieve, get extracting solution, the concentration of volume percent of the acid in the described aqueous acid is 1%～5%;
2. with Testa sojae atricolor, black rice, purple Radix Dauci Sativae, purple corn must, the purple corn skin, the Qarnet grain of rice, the purple corn rod, Rhizoma Dioscoreae esculentae, the mulberry fruit fruit, blue berry, Vaccinium myrtillus L. or indigo really are raw material, add described raw materials quality 3-12 concentration of volume percent doubly and be 10%～95% aqueous ethanolic solution or methanol aqueous solution or glycolic acid aqueous solution or the methanolic acid aqueous solution for extracting solvent, extract 1-6 time at 20-50 ℃, each 1-8 hour, cross the 80-120 mesh sieve, in temperature≤60 ℃, vacuum tightness is that 0.06～0.08MPa is evaporated to pol 2-40, obtain extract, is that 1: 1～10 ratio is dispersed in the water with described extract with mass ratio, and the concentration of volume percent of the acid in the described aqueous acid is 1%～5%;
(2) product that described step (1) is obtained is through macroporous resin adsorption, water and concentration of volume percent are that 10%～95% aqueous ethanolic solution or water and concentration of volume percent are 10%～95% methanol aqueous solution gradient elution, the component of cyaniding 3-0-glucoside is rich in collection, concentrating under reduced pressure, pol is 10～40 enriched material;
(3) be 1 with described enriched material in mass ratio: the ratio of 3-5 is dispersed to carries out polyamide resin absorption in the water, water and concentration of volume percent are that the aqueous ethanolic solution of 5%-75% or water and concentration of volume percent are the methanol aqueous solution gradient elution of 5%-75%, the component of cyaniding 3-0-glucoside is rich in collection, concentrating under reduced pressure, to pol be 10-40, drying, the efficient part of cyaniding 3-0-glucoside;
(4) efficient part with described cyaniding 3-0-glucoside carries out Toyopearl volume-exclusion chromatography column chromatography purification, the water removal of contamination, methanol aqueous solution with volume percent 20%-40% carries out the isoconcentration wash-out again, with the pure product of cyaniding 3-0-glucoside product in contrast, the component of cyaniding 3-0-glucoside is rich in collection, with the elutriant concentrating under reduced pressure, obtain the component that pol is 10-20, lyophilize obtains cyaniding 3-0-glucoside.
2. the extracting method of a kind of cyaniding 3-0-glucoside according to claim 1, it is characterized in that comprising the steps: described cyaniding 3-0-glucoside is carried out MCI gel filtration chromatography purifying, wash with water and remove decon, methyl alcohol with volume percent 10%-30% carries out the isoconcentration wash-out again, with the pure product of cyaniding 3-0-glucoside product in contrast, the component of cyaniding 3-0-glucoside is rich in collection, with the elutriant concentrating under reduced pressure, obtain the component that pol is 10-20, lyophilize obtains the pure product of cyaniding 3-0-glucoside, and described MCI gel resin is MCI GEL CHP20P.
3. the extracting method of a kind of cyaniding 3-0-glucoside according to claim 1, it is characterized in that described step (1) is extracted as: with Testa sojae atricolor, black rice, purple Radix Dauci Sativae, purple corn palpus, purple corn skin, the Qarnet grain of rice, purple corn rod, Rhizoma Dioscoreae esculentae, mulberry fruit fruit, blue berry, Vaccinium myrtillus L. or indigo really is raw material, the aqueous acid that adds 10 times of described raw materials quality is for extracting solvent, extract 3-5 time at 40-45 ℃, each 4-6 hour, cross 100 mesh sieves, get extracting solution, the concentration of volume percent of the acid in the described aqueous acid is 1%～3%.
4. the extracting method of a kind of cyaniding 3-0-glucoside according to claim 1, it is characterized in that described step (1) is extracted as: with Testa sojae atricolor, black rice, purple Radix Dauci Sativae, purple corn must, the purple corn skin, the Qarnet grain of rice, the purple corn rod, Rhizoma Dioscoreae esculentae, the mulberry fruit fruit, blue berry, Vaccinium myrtillus L. or indigo really are raw material, the concentration of volume percent that adds 10 times of described raw materials quality is that 40%～60% glycolic acid aqueous solution is for extracting solvent, extract 3-5 time at 20-30 ℃, each 4-6 hour, cross 100 mesh sieves, in temperature≤60 ℃, vacuum tightness is that 0.06～0.08MPa is evaporated to pol 2-40, obtain extract, is that 1: 4～5 ratio is dispersed in the water with described extract with mass ratio, and the concentration of volume percent of the acid in the described aqueous acid is 1%～3%.
5. according to the extracting method of a kind of cyaniding 3-0-glucoside of one of claim 1-4, it is characterized in that the acid in the described aqueous acid is hydrochloric acid, sulfuric acid, phosphoric acid, acetate or citric acid.
6. according to the extracting method of a kind of cyaniding 3-0-glucoside of one of claim 1-4, the model that it is characterized in that described macroporous resin is AB-8 type, HP20 type, HPD100 type, HPD100A type, HPD300 type, X-5 type, NKA-II type, D101 type or DA201 type.
7. according to the extracting method of a kind of cyaniding 3-0-glucoside of claim 1, it is characterized in that described Toyopearl resin is Toyopearl HW-40S, Toyopearl HW-40F, Toyopearl HW-40C, Toyopearl HW-50S, ToyopearlHW-50F, Toyopearl HW-55S, Toyopearl HW-55F, Toyopearl HW-65S, Toyopearl HW-65F, Toyopearl HW-75S or Toyopearl HW-75F.
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