CN102229631B - Method for separating and purifying malvidin glucoside from grape-skin red - Google Patents
Method for separating and purifying malvidin glucoside from grape-skin red Download PDFInfo
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Abstract
The invention relates to a method for separating and purifying malvidin glucoside from grape-skin red, which has the following advantages that: products are high in purity and low in cost; raw materials are easily available and are free of pollution; and used equipment is simple and is suitable for industrial production. The method comprises the following steps of: processing grape-skin red after dissolved with water by a macroporous adsorbent resin chromatographic column, carrying out gradient elution by using an aqueous and/or alcoholic solution, collecting components containing the malvidin glucoside, and carrying out pressurized concentration to obtain a crude product I; processing the crude product I by an activated carbon and diatomite mixed chromatographic column, eluting by using a chloroform and alcohol solution, and carrying out heating and reduced-pressure concentrating on eluent to obtain a crude product II; and processing the crude product II by a polyamide chromatographic column, carrying out gradient elution by using an aqueous and/or alcoholic solution, combining components with similar contents, repeatedly processing the combined components by the polyamide chromatographic column to obtain the malvidin glucoside with the content of 95%, and recrystallizing repeatedly through butanone-alcohol to obtain the malvidin glucoside with the content of more than 98%.
Description
Technical field
The invention belongs to natural drug and extract field, particularly a kind of from Pericarpium Vitis viniferae is red the method for separating and purifying high-purity Malvidin Glucoside.
Background technology
Pericarpium Vitis viniferae is red is that the residue of manufacturing after Sucus Vitis viniferae or grape wine is removed to seed and foreign material, refines and obtains through lixiviate, filtration, concentrate etc., belongs to anthocyanin class pigment.Anthocyanogen belongs to flavonoid class material, has anti-inflammatory, improves immunizing power, anti-oxidant, eliminates free radical, improves the lipid in liver and serum, prevents arteriosclerosis, improves the functions such as eyesight.
Malvidin Glucoside (malvidin-3-O-glucoside) is the flavonoid class composition take flavones as parent nucleus, and its structural formula is as follows:
This compound polarity is large, and good water solubility is soluble in methyl alcohol and ethanol, is insoluble in the non-polar solvent such as chloroform and ether.
Rheumatoid arthritis is a kind of common sacroiliitis, has the participation of multiple pro-inflammatory cytokine, as tumor necrosis factor-alpha (TNF-α) and interleukin-11 L-1,1L-6,1L-15 etc. in its morbidity.By suppressing generation or the effect of blocking-up gas of pro-inflammatory cytokine, can improve arthritis reaction.In addition, modern study thinks, nitric oxide production excessively synthetic be also one of pathogenetic important factor of rheumatoid arthritis.Studies have shown that, Malvidin Glucoside can suppress the expression of TNF-alpha active and nitric oxide synthetase, thereby treatment, prevents or improve rheumatoid arthritis, is made into different formulations and can be used for oral, external application and intradermal injection.
The method of the separating-purifying Malvidin Glucoside of having reported at present, mainly contains paper chromatography, column chromatography and preparative chromatography.Pericarpium Vitis viniferae methanol extract is crossed polymeric amide (Polyclar AT) chromatography column by Le Traon-Masson M P. etc., and first water washes away sugar, tannin and phenolic acid, then with volume ratio be CH
3oH: H
2o: HCl=70: the mixed solution wash-out of 30: 1, then through repeatedly separating, concentrated and lyophilize obtains 42% Malvidin Glucoside.Upper SE 52 fiber cation displacement chromatography posts Spagna G. and Piffer P.G. extract grape wine pigment with anhydrous methanol after, then use respectively the hydrochloric acid of 0.02mol/l, carry out wash-out containing 80% ethanol-water solution, 45% ethanol-water solution and the methyl alcohol of 0.2mol/l hydrochloric acid.Elutriant is analyzed by TLC and HPLC detects, and after collection is concentrated, obtains 48% Malvidin Glucoside.Tatsuzawa F. etc. extract 20g Impatiens textori Miq. with 5% aqueous acetic acid after, extract is respectively through Diaion HP-20 macroporous adsorbent resin column chromatography (5% acetic acid-methanol-eluted fractions), paper chromatography (BAW wash-out), thin-layer chromatography (15% acetic acid wash-out), preparative chromatography and Diaion HP-20 macroporous adsorbent resin column chromatography, and separation and purification obtains Malvidin Glucoside 5mg.
Because paper chromatography is only for semi-quantitative analysis, can not make the product that purity is higher, be of limited application.Add that its volume containing the sample is few, be not suitable for extensive separating-purifying.The amount of filler of preparative chromatography is large and expensive, causes production cost too high.
Summary of the invention
The object of the present invention is to provide a kind of from Pericarpium Vitis viniferae is red the method for separation and purification Malvidin Glucoside.
Technical scheme of the present invention is as follows:
A method for separation and purification Malvidin Glucoside from Pericarpium Vitis viniferae is red, its step is as follows:
1) by red Pericarpium Vitis viniferae with upper blade diameter length ratio after water dissolution be 1: 8~1: 10 macroporous adsorption resin chromatography post, the water that is 2~5 by pH value and/or alcoholic solution gradient elution, elutriant, by Liquid Detection, is collected the component that is rich in Malvidin Glucoside, heating concentrating under reduced pressure, obtains crude product I;
2) after repeatedly macroporous adsorbent resin column chromatography obtains crude product I merges, cross mass ratio and be 1: 1~1: 3 gac and diatomite mixings chromatography column, use chloroform and/or ethanolic soln wash-out, elutriant is heated to concentrating under reduced pressure, obtain coarse-grain II;
3) crude product II adds 80-100 order polymeric amide mixing and stirring after dissolving in the ratio of 1g: 5~15ml with ethanol, after doing, must mix sample polymeric amide with Rotary Evaporators is concentrated, and the mass ratio of crude product II and polymeric amide is 0.5~2.0: 1; In chromatography column, add successively polymeric amide and mix sample polymeric amide, adopt dry column-packing; The blade diameter length ratio of dry column-packing is 1: 3~1: 8, and polymeric amide is 3~8 with the aspect ratio of mixing sample polymeric amide; Use aqueous ethanolic solution gradient elution, elutriant is collected in batches, by Liquid Detection result, merges content close component, by after its concentrating under reduced pressure, after 3~5 polymeric amide chromatography posts, obtains Malvidin Glucoside content and be 95% fine work with aforesaid method;
4) fine work, by the heavy periodic crystallisation of ethanol-butanone, obtains more than 98% Malvidin Glucoside of content.
Described step 1) described in the model of macroporous adsorbent resin be one of D101, D201, Diaion HP-20, NKA-II, HPD100, AB-8, X-5 or S8.
Described step 1) described in alcohol be one of methyl alcohol, ethanol or propyl alcohol.
Described step 1) described in water and/or alcohol mixed solvent in the concentration of volume percent of alcohol be 0~100%.
Described step 2) described in chloroform and alcohol mixed solvent in the concentration of volume percent of ethanol be 0~100%.
Described step 3) described in eluent water and/or alcoholic solution in alcohol be one of methyl alcohol, ethanol or propyl alcohol.
Described step 3) described in water and/or alcohol mixed solvent in the concentration of volume percent of alcohol be 0~100%.
Described step 4) described in the recrystallization time be 6~48h.
Described step 4) described in when recrystallization solvent load be: sample: ethanol: butanone=1g: 5ml: 5ml~1g: 5ml: 30ml.
Feature of the present invention is: column chromatography high-efficient simple, separation capacity are large, is applicable to complex sample and separates and purifying; Macroporous adsorbent resin and polymeric amide can be regenerated and be reused by simple method, reduce costs, and equipment used is simple, and suitability for industrialized is produced; Can obtain the Malvidin Glucoside of high-content by polycaprolactam column purification.The present invention be advantageous in that: product purity is high, Malvidin Glucoside content reaches more than 98%; Macroporous adsorbent resin and polyamide resin can reuse, and cost is low; Raw material is easy to get pollution-free; Equipment used is simple, and suitability for industrialized is produced.The present invention's separation from Pericarpium Vitis viniferae is red, purifying Malvidin Glucoside, have the advantages such as with low cost, raw material sources are extensive, market outlook are wide.
Embodiment
Embodiment 1:
(1) by red 500.0g Pericarpium Vitis viniferae dissolve completely with 5L water after, upper treated D101 macroporous adsorptive resins, and after with the elutriant of collecting, drip washing pillar fully adsorbs it repeatedly, the water that is 3 with pH and volume percent are 20%, 40%, 60%, the gradient elution of 80% and 95% aqueous ethanolic solution, every 1L receives volume as one, detect by HPLC, merge the component that is rich in Malvidin Glucoside, by it in temperature≤70 ℃, vacuum tightness is under 0.05~0.08MPa, after concentrating under reduced pressure, to obtain crude product I3.1g, its Malvidin Glucoside content is 21.8%.
(2), after 250.0g gac and 250.0g diatomite are mixed, soak 30min with chloroform, wet method dress post, blade diameter length ratio is 1: 8.Get upper prop after crude product I (average content of Malvidin Glucoside is 22.3%) the 50.0g 250ml dissolve with ethanol that macroporous adsorbing resin for purification obtains, ethanol-chloroformic solution the wash-out that is 8% by volume percent after its absorption fully, elutriant is in temperature≤45 ℃, vacuum tightness is under 0.05~0.08MPa, after concentrating under reduced pressure, to obtain crude product II39.2g, and its Malvidin Glucoside content is 36.5%.
(3) crude product II is with adding 39.2g polymeric amide (80-100 order) mixing and stirring after 210ml dissolve with ethanol, with Rotary Evaporators in temperature≤50 ℃, concentrated dry the sample polymeric amide of mixing under vacuum tightness 0.06~0.08Mpa.In chromatography column, add polymeric amide, then add and mix sample polymeric amide, after dress is real, blade diameter length ratio is 1: 5.Water and volume percent are 5%, 8%, 10%, 15%, 25% and 95% aqueous ethanolic solution gradient elution, every 250ml receives volume as one, detect by HPLC, merge the component that is rich in Malvidin Glucoside, by it in temperature≤70 ℃, vacuum tightness is under 0.05~0.08MPa, after concentrating under reduced pressure, to obtain crude product III 9.7g, and its Malvidin Glucoside content is 67.3%.
By aforementioned proportion and method by crude product III after 3 polymeric amide chromatography posts, obtain Malvidin Glucoside content and reach 95% fine work 1.2g.
(4) fine work is with after dissolve with ethanol, by fine work: ethanol: butanone=1g: 5ml: 10ml is recrystallization 3 times (normal-temperature dissolution ,-25~-30 ℃ of freezing 12h) repeatedly, obtains content and reaches more than 98% Malvidin Glucoside.
Embodiment 2:
(1) by red 500.0g Pericarpium Vitis viniferae dissolve completely with 5L water after, upper treated D201 macroporous adsorptive resins, and after with the elutriant of collecting, drip washing pillar fully adsorbs it repeatedly, the water that is 4 with pH and volume percent are 15%, 30%, 45%, 60%, 75% and 95% aqueous ethanolic solution gradient elution, every 1L receives volume as one, detect by HPLC, merge the component that is rich in Malvidin Glucoside, by it in temperature≤70 ℃, vacuum tightness is under 0.05~0.08MPa, after concentrating under reduced pressure, to obtain crude product I2.8g, its Malvidin Glucoside content is 23.2%.
(2), after 250.0g gac and 250.0g diatomite are mixed, soak 30min with chloroform, wet method dress post, blade diameter length ratio is 1: 4.Get crude product I (average content of Malvidin Glucoside is 24.1%) 50.0g rear upper prop of dissolving under 250ml alcohol at normal temperature that macroporous adsorbing resin for purification obtains, ethanol-chloroformic solution the wash-out that is 15% by volume percent after its absorption fully, elutriant is in temperature≤45 ℃, vacuum tightness is under 0.05~0.08MPa, after concentrating under reduced pressure, to obtain crude product II39.6g, and its Malvidin Glucoside content is 38.9%.
(3) crude product II, with adding 71.2g polymeric amide (80-100 order) mixing and stirring after 178ml dissolve with ethanol, in temperature≤50 ℃, concentrated do after must mix sample polymeric amide under vacuum tightness 0.05~0.08Mpa with Rotary Evaporators.In chromatography column, add polymeric amide, then add and mix sample polymeric amide, after dress is real, blade diameter length ratio is 1: 6.Aqueous ethanolic solution gradient elution take water and volume percent as 5%, 15%, 20%, 25%, 50% and 95%, every 250ml receives volume as one, detect by HPLC, merge the component that is rich in Malvidin Glucoside, by it in temperature≤70 ℃, vacuum tightness is under 0.05~0.08MPa, after concentrating under reduced pressure, to obtain crude product III8.4g, and its Malvidin Glucoside content is 71.5%.
By aforementioned proportion and method by crude product III after 4 polymeric amide chromatography posts, obtain Malvidin Glucoside content and reach 95% fine work 2.1g.
(4) fine work is with pressing fine work after dissolve with ethanol: ethanol: butanone=1g: 5ml: 15ml recrystallization 3 times (normal-temperature dissolution ,-25~-30 ℃ of freezing 6h), obtains content and reach more than 98% Malvidin Glucoside.
Embodiment 3:
(1) by red 500.0g Pericarpium Vitis viniferae dissolve completely with 5L water after, upper treated Diaion HP-20 macroporous adsorptive resins, and after with the elutriant of collecting, drip washing pillar fully adsorbs it repeatedly, the water that is 5 with pH and volume percent are 20%, 40%, 60%, the gradient elution of 80% and 95% aqueous ethanolic solution, every 1L receives volume as one, detect by HPLC, merge the component that is rich in Malvidin Glucoside, by it in temperature≤70 ℃, vacuum tightness is under 0.05~0.08MPa, after concentrating under reduced pressure, to obtain crude product I4.1g, its Malvidin Glucoside content is 21.9%.
(2), after 250.0g gac and 250.0g diatomite are mixed, soak 30min with chloroform, wet method dress post, blade diameter length ratio is 1: 8.Get upper prop after crude product I (average content of Malvidin Glucoside is 26.4%) the 50.0g 250ml dissolve with ethanol that macroporous adsorbing resin for purification obtains, ethanol-chloroformic solution the wash-out that is 20% by volume percent after its absorption fully, elutriant is in temperature≤45 ℃, vacuum tightness is under 0.05~0.08MPa, after concentrating under reduced pressure, to obtain crude product II35.6g, and its Malvidin Glucoside content is 39.6%.
(3) crude product II, with adding 53.4g polymeric amide (80-100 order) mixing and stirring after 178ml dissolve with ethanol, in temperature≤50 ℃, concentrated do after must mix sample polymeric amide under vacuum tightness 0.05~0.08Mpa with Rotary Evaporators.In chromatography column, add polymeric amide, then add and mix sample polymeric amide, after dress is real, blade diameter length ratio is 1: 5.Aqueous ethanolic solution gradient elution take water and volume percent as 5%, 15%, 20%, 50% and 95%, every 250ml receives volume as one, detect by HPLC, merge the component that is rich in Malvidin Glucoside, by it in temperature≤70 ℃, vacuum tightness is under 0.05~0.08MPa, after concentrating under reduced pressure, to obtain crude product III7.5g, and its Malvidin Glucoside content is 66.8%.
By aforementioned proportion and method by crude product III after 4 polymeric amide chromatography posts, obtain Malvidin Glucoside content and reach 95% fine work 2.7g.
(4) fine work dissolve with ethanol, by fine work: ethanol: butanone=1g: 5ml: 30ml recrystallization 3 times (normal-temperature dissolution ,-25~-30 ℃ of freezing 24h), obtains content and reach more than 98% Malvidin Glucoside.
Embodiment 4:
(1) by red 500.0g Pericarpium Vitis viniferae dissolve completely with 5L water after, upper treated NKA-II macroporous adsorptive resins, and after with the elutriant of collecting, drip washing pillar fully adsorbs it repeatedly, the water that is 5 with pH and volume percent are 10%, 30%, 50%, the gradient elution of 70% and 95% aqueous ethanolic solution, every 1L receives volume as one, detect by HPLC, merge the component that is rich in Malvidin Glucoside, by it in temperature≤70 ℃, vacuum tightness is under 0.05~0.08MPa, after concentrating under reduced pressure, to obtain crude product I2.3g, its Malvidin Glucoside content is 29.8%.
(2), after 250.0g gac and 250.0g diatomite are mixed, soak 30min with chloroform, wet method dress post, blade diameter length ratio is 1: 5.Get upper prop after crude product I (average content of Malvidin Glucoside is 27.9%) the 50.0g 250ml dissolve with ethanol that macroporous adsorbing resin for purification obtains, ethanol-chloroformic solution the wash-out that is 25% by volume percent after it fully adsorbs, elutriant is in temperature temperature≤45 ℃, vacuum tightness is under 0.05~0.08MPa, after concentrating under reduced pressure, to obtain crude product II39.6g, and its Malvidin Glucoside content is 35.6%.
(3) crude product II, with adding 79.2g polymeric amide (80-100 order) mixing and stirring after 198ml dissolve with ethanol, in temperature≤50 ℃, concentrated do after must mix sample polymeric amide under vacuum tightness 0.05~0.08Mpa with Rotary Evaporators.In chromatography column, add polymeric amide, then add and mix sample polymeric amide, after dress is real, blade diameter length ratio is 1: 7.Aqueous ethanolic solution gradient elution take water and volume percent as 10%, 20%, 30%, 50%, 70% and 95%, every 250ml receives volume as one, detect by HPLC, merge the component that is rich in Malvidin Glucoside, by it in temperature≤70 ℃, vacuum tightness is under 0.05~0.08MPa, after concentrating under reduced pressure, to obtain crude product III8.9g, and its Malvidin Glucoside content is 71.4%.
By aforementioned proportion and method by crude product III after 4 polymeric amide chromatography posts, obtain Malvidin Glucoside content and reach 95% fine work 2.3g.
(4) fine work dissolve with ethanol, by fine work: ethanol: butanone=1g: 5ml: 30ml recrystallization 3 times (normal-temperature dissolution ,-25~-30 ℃ of freezing 48h), obtains content and reach more than 98% Malvidin Glucoside.
Embodiment 5:
(1) by red 500.0g Pericarpium Vitis viniferae dissolve completely with 5L water after, upper treated HPD-100 macroporous adsorptive resins, and after with the elutriant of collecting, drip washing pillar fully adsorbs it repeatedly, the water that is 3 with pH and volume percent are 10%, 25%, 40%, the gradient elution of 55% and 95% aqueous ethanolic solution, every 1L receives volume as one, detect by HPLC, merge the component that is rich in Malvidin Glucoside, by it in temperature≤70 ℃, vacuum tightness is under 0.05~0.08MPa, after concentrating under reduced pressure, to obtain crude product I 3.1g, its Malvidin Glucoside content is about 21.7%.
(2), after 250.0g gac and 250.0g diatomite are mixed, soak 30min with chloroform, wet method dress post, blade diameter length ratio is 1: 5.Get crude product I (average content of Malvidin Glucoside is 22.3%) 50.0g rear upper prop of dissolving under 250ml alcohol at normal temperature that macroporous adsorbing resin for purification obtains, ethanol-chloroformic solution the wash-out that is 15% with volume percent degree after its absorption fully, elutriant is in temperature≤45 ℃, vacuum tightness is under 0.05~0.08MPa, after concentrating under reduced pressure, to obtain crude product II37.1g, and its Malvidin Glucoside content is 48.6%.
(3) crude product II, with adding 56.7g polymeric amide (80-100 order) mixing and stirring after 185ml dissolve with ethanol, in temperature≤50 ℃, concentrated do after must mix sample polymeric amide under vacuum tightness 0.05~0.08Mpa with Rotary Evaporators.In chromatography column, add polymeric amide, then add and mix sample polymeric amide, after dress is real, blade diameter length ratio is 1: 7.Aqueous ethanolic solution gradient elution take water and volume percent as 10%, 20%, 40%, 60%, 80% and 95%, every 250ml receives volume as one, detect by HPLC, merge the component that is rich in Malvidin Glucoside, by it in temperature≤70 ℃, vacuum tightness is under 0.05~0.08MPa, after concentrating under reduced pressure, to obtain crude product III7.7g, and its Malvidin Glucoside content is about 74.8%.
By aforementioned proportion and method by crude product III after 3 polymeric amide chromatography posts, obtain Malvidin Glucoside content and reach 95% fine work 2.5g.
(4) fine work dissolve with ethanol, by fine work: ethanol: butanone=1g: 5ml: 20ml recrystallization 3 times (normal-temperature dissolution ,-25~-30 ℃ of freezing 24h) 3 times, obtains content and reach more than 98% Malvidin Glucoside.
Claims (4)
1. a method for separation and purification Malvidin Glucoside from Pericarpium Vitis viniferae is red, its step is as follows:
1) by red Pericarpium Vitis viniferae with upper blade diameter length ratio after water dissolution be 1:8~1:10 macroporous adsorption resin chromatography post, the water that is 2~5 by pH value and aqueous ethanolic solution gradient elution, the concentration of volume percent of aqueous ethanolic solution is 0~100%, elutriant passes through Liquid Detection, the component of Malvidin Glucoside is rich in collection, heating concentrating under reduced pressure, obtains crude product I;
2) after the crude product I that repeatedly macroporous adsorbent resin column chromatography obtains merges, crossing mass ratio is 1:1~1:3 gac and diatomite mixing chromatography column, with ethanol-chloroformic solution wash-out, the concentration of volume percent of ethanol-chloroformic solution is 8~25%, elutriant is heated to concentrating under reduced pressure, obtain crude product II;
3) crude product II adds 80-100 order polymeric amide mixing and stirring after dissolving in the ratio of 1g:5~15ml with ethanol, after doing, must mix sample polymeric amide with Rotary Evaporators is concentrated, and the mass ratio of crude product II and polymeric amide is 0.5~2.0:1; In chromatography column, add successively polymeric amide and mix sample polymeric amide, adopt dry column-packing; The blade diameter length ratio of dry column-packing is 1:3~1:8, and polymeric amide is 3~8 with the aspect ratio of mixing sample polymeric amide; Use aqueous ethanolic solution gradient elution, the concentration of volume percent of aqueous ethanolic solution is 0~100%, elutriant is collected in batches, by Liquid Detection result, merge the close component of content, by after its concentrating under reduced pressure, after 3~5 polymeric amide chromatography posts, obtain Malvidin Glucoside content and be 95% fine work with aforesaid method;
4) fine work, by ethanol-butanone recrystallization repeatedly, obtains more than 98% Malvidin Glucoside of content.
According to claim 1 a kind of from Pericarpium Vitis viniferae is red the method for separation and purification Malvidin Glucoside, it is characterized in that: described step 1) described in the model of macroporous adsorbent resin be one of D101, D201, Diaion HP-20, NKA-II, HPD100, AB-8, X-5 or S8.
According to claim 1 a kind of from Pericarpium Vitis viniferae is red the method for separation and purification Malvidin Glucoside, it is characterized in that: described step 4) described in the recrystallization time be 6~48h.
According to claim 1 a kind of from Pericarpium Vitis viniferae is red the method for separation and purification Malvidin Glucoside, it is characterized in that: described step 4) described in when recrystallization solvent load be: sample: ethanol: butanone=1g:5ml:5ml~1g:5ml:30ml.
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CN104177460B (en) * | 2014-07-17 | 2016-06-08 | 中国农业大学 | The preparation method of a kind of 3,5-disaccharides anthocyanin |
CN104138367B (en) * | 2014-08-15 | 2016-03-09 | 江苏省中国科学院植物研究所 | The purposes of Kosteletzkya virginica element in preparation control inflammation related disease medicine |
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