CN102229631A - 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 the 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 to be that the residue after manufacturing Sucus Vitis viniferae or the grape wine is removed seed and foreign material, makes with extra care and gets through lixiviate, filtration, concentrate etc., belongs to anthocyanin class pigment.Anthocyanogen belongs to the flavonoid class material, has anti-inflammatory, improves immunizing power, and is anti-oxidant, eliminates free radical, improves the lipid in liver and the serum, prevents arteriosclerosis, improves functions such as eyesight.
Malvidin Glucoside (malvidin-3-O-glucoside) is to be the flavonoid class composition of parent nucleus with the flavones, and its structural formula is as follows:
This compound polarity is big, and good water solubility is soluble in methyl alcohol and the ethanol, is insoluble in the non-polar solvents such as chloroform and ether.
Rheumatoid arthritis is a kind of common sacroiliitis, the participation of multiple pro-inflammatory cytokine is arranged, as tumor necrosis factor-alpha (TNF-α) and interleukin-11 L-1,1L-6,1L-15 etc. in its morbidity.Generation or the effect of blocking-up gas by suppressing pro-inflammatory cytokine can improve the arthritis reaction.In addition, modern study thinks that nitric oxide production excessively synthesizing also is 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, prevent or improve rheumatoid arthritis, be made into different formulations and can be used for oral, external application and intradermal injection.
The method of the separation purification Malvidin Glucoside of having reported at present, mainly contains paper chromatography, column chromatography and preparative chromatography.Le Traon-Masson M P. etc. crosses polymeric amide (Polyclar AT) chromatography column with the Pericarpium Vitis viniferae methanol extract, and first water washes away sugar, tannin and phenolic acid, is CH with volume ratio again
3OH: H
2O: HCl=70: 30: 1 mixed solution wash-out, then through separating repeatedly, concentrate and lyophilize obtaining 42% Malvidin Glucoside.Spagna G. and Piffer P.G. extract the back with the grape wine pigment with anhydrous methanol and go up SE 52 fiber cation displacement chromatography posts, use the hydrochloric acid of 0.02mol/l then respectively, 80% ethanol-water solution, 45% ethanol-water solution and the methyl alcohol that contain 0.2mol/l hydrochloric acid carry out wash-out.Elutriant analyzes by TLC and HPLC detects, and collection obtains 48% Malvidin Glucoside after concentrating.Tatsuzawa F. etc. extract the 20g Impatiens textori Miq. with 5% aqueous acetic acid after, extract is analysed (BAW wash-out), thin-layer chromatography (15% acetic acid wash-out), preparative chromatography and Diaion HP-20 macroporous adsorbent resin column chromatography through Diaion HP-20 macroporous adsorbent resin column chromatography (5% acetic acid-methanol-eluted fractions), ply of paper respectively, and separation and purification obtains Malvidin Glucoside 5mg.
Because paper chromatography only is used for semi-quantitative analysis, can not make the purity high product, is of limited application.Add that its volume containing the sample is few, be not suitable for purifying extensive the separation.The amount of filler of preparative chromatography is big and cost an arm and a leg, and 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 kind of from Pericarpium Vitis viniferae is red the method for separation and purification Malvidin Glucoside, its step is as follows:
1) with Pericarpium Vitis viniferae red be 1: 8～1: 10 macroporous adsorption resin chromatography post with going up blade diameter length ratio after the water dissolution, with the pH value is 2～5 water and/or alcoholic solution gradient elution, and elutriant is collected the component that is rich in Malvidin Glucoside by Liquid Detection, the heating concentrating under reduced pressure gets crude product I;
2) repeatedly the crude product I that obtains of macroporous adsorbent resin column chromatography merges the back to cross mass ratio is 1: 1～1: 3 gac and diatomite mixings chromatography column, with chloroform and/or ethanolic soln wash-out, elutriant is heated concentrating under reduced pressure, gets coarse-grain II;
3) crude product II dissolves back adding 80-100 order polymeric amide mixing and stirring with ethanol in the ratio of 1g: 5～15ml, must mix the sample polymeric amide after doing with Rotary Evaporators is concentrated, and the mass ratio of crude product II and polymeric amide is 0.5～2.0: 1; Add polymeric amide in the chromatography column successively and mix the 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 the sample polymeric amide; Use the aqueous ethanolic solution gradient elution, elutriant is collected in batches, by the Liquid Detection result, merges the close component of content, behind its concentrating under reduced pressure, after 3～5 polymeric amide chromatography posts, obtains Malvidin Glucoside content and be 95% elaboration with aforesaid method;
4) elaboration obtains the Malvidin Glucoside of content more than 98% by the heavy periodic crystallisation of ethanol-butanone.
The model of the macroporous adsorbent resin described in the described step 1) is one of D101, D201, Diaion HP-20, NKA-II, HPD100, AB-8, X-5 or S8.
Alcohol described in the described step 1) is one of methyl alcohol, ethanol or propyl alcohol.
The concentration of volume percent of alcohol is 0～100% in water described in the described step 1) and/or the pure mixed solvent.
Described step 2) the alcoholic acid concentration of volume percent is 0～100% in chloroform described in and the alcohol mixed solvent.
Alcohol is one of methyl alcohol, ethanol or propyl alcohol in eluent water described in the described step 3) and/or the alcoholic solution.
The concentration of volume percent of alcohol is 0～100% in water described in the described step 3) and/or the pure mixed solvent.
The recrystallization time described in the described step 4) is 6～48h.
Solvent load is during recrystallization described in the described step 4): sample: ethanol: butanone=1g: 5ml: 5ml～1g: 5ml: 30ml.
Characteristics of the present invention are: column chromatography high-efficient simple, separation capacity are big, are fit to complex sample and separate and purifying; Macroporous adsorbent resin and polymeric amide can reduce cost by simple method regeneration and recycling, and equipment used is simple, suitability for industrialized production; Can obtain high-load Malvidin Glucoside by polymeric amide adsorption column purifying.The present invention be advantageous in that: the product purity height, 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, suitability for industrialized production.The present invention separates from Pericarpium Vitis viniferae is red, the purifying Malvidin Glucoside, has advantages such as with low cost, that raw material sources are extensive, market outlook are wide.
Embodiment
Embodiment 1:
(1) with the 500.0g Pericarpium Vitis viniferae is red dissolve fully with 5L water after, go up treated D101 macroporous adsorptive resins, and with the elutriant of collecting after the drip washing pillar fully adsorbs it repeatedly, with pH is that 3 water 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, with it in temperature≤70 ℃, vacuum tightness is to get crude product I3.1g under 0.05～0.08MPa behind the concentrating under reduced pressure, and its Malvidin Glucoside content is 21.8%.
(2) 250.0g gac and 250.0g diatomite are mixed after, soak 30min with chloroform, wet method dress post, blade diameter length ratio is 1: 8.Get crude product I (average content of Malvidin Glucoside is 22.3%) 50.0g that the macroporous adsorbent resin enrichment obtains with the 250ml dissolve with ethanol after upper prop, treat that the abundant back of its absorption is ethanol-chloroformic solution wash-out of 8% with volume percent, elutriant is in temperature≤45 ℃, vacuum tightness is to get crude product II39.2g under 0.05～0.08MPa behind the concentrating under reduced pressure, 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 behind the 210ml dissolve with ethanol, and in temperature≤50 ℃, vacuum tightness 0.06～0.08Mpa concentrates down and does to such an extent that mix the sample polymeric amide with Rotary Evaporators.Add polymeric amide in chromatography column, then add and mix the sample polymeric amide, the real back of dress 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, with it in temperature≤70 ℃, vacuum tightness is to get crude product III 9.7g under 0.05～0.08MPa behind the concentrating under reduced pressure, and its Malvidin Glucoside content is 67.3%.
With aforementioned proportion and method with crude product III after 3 polymeric amide chromatography posts, obtain Malvidin Glucoside content and reach 95% elaboration 1.2g.
(4) elaboration with dissolve with ethanol after, press elaboration: ethanol: butanone=1g: 5ml: 10ml is recrystallization 3 times (normal-temperature dissolution ,-25～-30 ℃ of freezing 12h) repeatedly, obtains content and reaches Malvidin Glucoside more than 98%.
Embodiment 2:
(1) with the 500.0g Pericarpium Vitis viniferae is red dissolve fully with 5L water after, go up treated D201 macroporous adsorptive resins, and with the elutriant of collecting after the drip washing pillar fully adsorbs it repeatedly, with pH is that 4 water 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, with it in temperature≤70 ℃, vacuum tightness is to get crude product I2.8g under 0.05～0.08MPa behind the concentrating under reduced pressure, and its Malvidin Glucoside content is 23.2%.
(2) 250.0g gac and 250.0g diatomite are mixed after, 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%) the 50.0g 250ml alcohol at normal temperature dissolving back upper prop down that the macroporous adsorbent resin enrichment obtains, treat that the abundant back of its absorption is ethanol-chloroformic solution wash-out of 15% with volume percent, elutriant is in temperature≤45 ℃, vacuum tightness is to get crude product II39.6g under 0.05～0.08MPa behind the concentrating under reduced pressure, and its Malvidin Glucoside content is 38.9%.
(3) crude product II is with adding 71.2g polymeric amide (80-100 order) mixing and stirring behind the 178ml dissolve with ethanol, and in temperature≤50 ℃, vacuum tightness 0.05～0.08Mpa must mix the sample polymeric amide after concentrating down and doing with Rotary Evaporators.Add polymeric amide in chromatography column, then add and mix the sample polymeric amide, the real back of dress blade diameter length ratio is 1: 6.It with water and volume percent 5%, 15%, 20%, 25%, 50% 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, with it in temperature≤70 ℃, vacuum tightness is to get crude product III8.4g under 0.05～0.08MPa behind the concentrating under reduced pressure, and its Malvidin Glucoside content is 71.5%.
With aforementioned proportion and method with crude product III after 4 polymeric amide chromatography posts, obtain Malvidin Glucoside content and reach 95% elaboration 2.1g.
(4) elaboration is pressed elaboration after with dissolve with ethanol: ethanol: butanone=1g: 5ml: 15ml recrystallization 3 times (normal-temperature dissolution ,-25～-30 ℃ of freezing 6h) obtains content and reaches Malvidin Glucoside more than 98%.
Embodiment 3:
(1) with the 500.0g Pericarpium Vitis viniferae is red dissolve fully with 5L water after, go up treated Diaion HP-20 macroporous adsorptive resins, and with the elutriant of collecting after the drip washing pillar fully adsorbs it repeatedly, with pH is that 5 water 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, with it in temperature≤70 ℃, vacuum tightness is to get crude product I4.1g under 0.05～0.08MPa behind the concentrating under reduced pressure, and its Malvidin Glucoside content is 21.9%.
(2) 250.0g gac and 250.0g diatomite are mixed after, soak 30min with chloroform, wet method dress post, blade diameter length ratio is 1: 8.Get crude product I (average content of Malvidin Glucoside is 26.4%) 50.0g that the macroporous adsorbent resin enrichment obtains with the 250ml dissolve with ethanol after upper prop, treat that the abundant back of its absorption is ethanol-chloroformic solution wash-out of 20% with volume percent, elutriant is in temperature≤45 ℃, vacuum tightness is to get crude product II35.6g under 0.05～0.08MPa behind the concentrating under reduced pressure, and its Malvidin Glucoside content is 39.6%.
(3) crude product II is with adding 53.4g polymeric amide (80-100 order) mixing and stirring behind the 178ml dissolve with ethanol, and in temperature≤50 ℃, vacuum tightness 0.05～0.08Mpa must mix the sample polymeric amide after concentrating down and doing with Rotary Evaporators.Add polymeric amide in chromatography column, then add and mix the sample polymeric amide, the real back of dress blade diameter length ratio is 1: 5.It with water and volume percent 5%, 15%, 20%, 50% 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, with it in temperature≤70 ℃, vacuum tightness is to get crude product III7.5g under 0.05～0.08MPa behind the concentrating under reduced pressure, and its Malvidin Glucoside content is 66.8%.
With aforementioned proportion and method with crude product III after 4 polymeric amide chromatography posts, obtain Malvidin Glucoside content and reach 95% elaboration 2.7g.
(4) elaboration dissolve with ethanol, press elaboration: ethanol: butanone=1g: 5ml: 30ml recrystallization 3 times (normal-temperature dissolution ,-25～-30 ℃ of freezing 24h) obtains content and reaches Malvidin Glucoside more than 98%.
Embodiment 4:
(1) with the 500.0g Pericarpium Vitis viniferae is red dissolve fully with 5L water after, go up treated NKA-II macroporous adsorptive resins, and with the elutriant of collecting after the drip washing pillar fully adsorbs it repeatedly, with pH is that 5 water 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, with it in temperature≤70 ℃, vacuum tightness is to get crude product I2.3g under 0.05～0.08MPa behind the concentrating under reduced pressure, and its Malvidin Glucoside content is 29.8%.
(2) 250.0g gac and 250.0g diatomite are mixed after, 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 27.9%) 50.0g that the macroporous adsorbent resin enrichment obtains with the 250ml dissolve with ethanol after upper prop, treat that it fully adsorbs the back is ethanol-chloroformic solution wash-out of 25% with volume percent, elutriant is in temperature temperature≤45 ℃, vacuum tightness is to get crude product II39.6g under 0.05～0.08MPa behind the concentrating under reduced pressure, and its Malvidin Glucoside content is 35.6%.
(3) crude product II is with adding 79.2g polymeric amide (80-100 order) mixing and stirring behind the 198ml dissolve with ethanol, and in temperature≤50 ℃, vacuum tightness 0.05～0.08Mpa must mix the sample polymeric amide after concentrating down and doing with Rotary Evaporators.Add polymeric amide in chromatography column, then add and mix the sample polymeric amide, the real back of dress blade diameter length ratio is 1: 7.It with water and volume percent 10%, 20%, 30%, 50%, 70% 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, with it in temperature≤70 ℃, vacuum tightness is to get crude product III8.9g under 0.05～0.08MPa behind the concentrating under reduced pressure, and its Malvidin Glucoside content is 71.4%.
With aforementioned proportion and method with crude product III after 4 polymeric amide chromatography posts, obtain Malvidin Glucoside content and reach 95% elaboration 2.3g.
(4) elaboration dissolve with ethanol, press elaboration: ethanol: butanone=1g: 5ml: 30ml recrystallization 3 times (normal-temperature dissolution ,-25～-30 ℃ of freezing 48h) obtains content and reaches Malvidin Glucoside more than 98%.
Embodiment 5:
(1) with the 500.0g Pericarpium Vitis viniferae is red dissolve fully with 5L water after, go up treated HPD-100 macroporous adsorptive resins, and with the elutriant of collecting after the drip washing pillar fully adsorbs it repeatedly, with pH is that 3 water 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, with it in temperature≤70 ℃, vacuum tightness is to get crude product I 3.1g under 0.05～0.08MPa behind the concentrating under reduced pressure, and its Malvidin Glucoside content is about 21.7%.
(2) 250.0g gac and 250.0g diatomite are mixed after, 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%) the 50.0g 250ml alcohol at normal temperature dissolving back upper prop down that the macroporous adsorbent resin enrichment obtains, treat that the abundant back of its absorption is ethanol-chloroformic solution wash-out of 15% with the volume percent degree, elutriant is in temperature≤45 ℃, vacuum tightness is to get crude product II37.1g under 0.05～0.08MPa behind the concentrating under reduced pressure, and its Malvidin Glucoside content is 48.6%.
(3) crude product II is with adding 56.7g polymeric amide (80-100 order) mixing and stirring behind the 185ml dissolve with ethanol, and in temperature≤50 ℃, vacuum tightness 0.05～0.08Mpa must mix the sample polymeric amide after concentrating down and doing with Rotary Evaporators.Add polymeric amide in chromatography column, then add and mix the sample polymeric amide, the real back of dress blade diameter length ratio is 1: 7.It with water and volume percent 10%, 20%, 40%, 60%, 80% 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, with it in temperature≤70 ℃, vacuum tightness is to get crude product III7.7g under 0.05～0.08MPa behind the concentrating under reduced pressure, and its Malvidin Glucoside content is about 74.8%.
With aforementioned proportion and method with crude product III after 3 polymeric amide chromatography posts, obtain Malvidin Glucoside content and reach 95% elaboration 2.5g.
(4) elaboration dissolve with ethanol, press elaboration: ethanol: butanone=1g: 5ml: 20ml recrystallization 3 times (normal-temperature dissolution ,-25～-30 ℃ of freezing 24h) 3 times obtains content and reaches Malvidin Glucoside more than 98%.
Claims (9)
1. the method for a separation and purification Malvidin Glucoside from Pericarpium Vitis viniferae is red, its step is as follows:
1) with Pericarpium Vitis viniferae red be 1: 8～1: 10 macroporous adsorption resin chromatography post with going up blade diameter length ratio after the water dissolution, with the pH value is 2～5 water and/or alcoholic solution gradient elution, and elutriant is collected the component that is rich in Malvidin Glucoside by Liquid Detection, the heating concentrating under reduced pressure gets crude product I;
2) repeatedly the crude product I that obtains of macroporous adsorbent resin column chromatography merges the back to cross mass ratio is 1: 1～1: 3 gac and diatomite mixings chromatography column, with chloroform and/or ethanolic soln wash-out, elutriant is heated concentrating under reduced pressure, gets crude product II;
3) crude product II dissolves back adding 80-100 order polymeric amide mixing and stirring with ethanol in the ratio of 1g: 5～15ml, must mix the sample polymeric amide after doing with Rotary Evaporators is concentrated, and the mass ratio of crude product II and polymeric amide is 0.5～2.0: 1; Add polymeric amide in the chromatography column successively and mix the 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 the sample polymeric amide; Use the aqueous ethanolic solution gradient elution, elutriant is collected in batches, by the Liquid Detection result, merges the close component of content, behind its concentrating under reduced pressure, after 3～5 polymeric amide chromatography posts, obtains Malvidin Glucoside content and be 95% elaboration with aforesaid method;
4) elaboration obtains the Malvidin Glucoside of content more than 98% by the heavy periodic crystallisation of ethanol-butanone.
2. 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: the model of the macroporous adsorbent resin described in the described step 1) is one of D101, D201, Diaion HP-20, NKA-II, HPD100, AB-8, X-5 or S8.
3. 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: the alcohol described in the described step 1) is one of methyl alcohol, ethanol or propyl alcohol.
4. 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: the concentration of volume percent of alcohol is 0～100% in water described in the described step 1) and/or the pure mixed solvent.
5. 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: the alcoholic acid concentration of volume percent is 0～100% in chloroform described step 2) and the alcohol mixed solvent.
6. 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: alcohol is one of methyl alcohol, ethanol or propyl alcohol in eluent water described in the described step 3) and/or the alcoholic solution.
7. 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: the concentration of volume percent of alcohol is 0～100% in water described in the described step 3) and/or the pure mixed solvent.
8. 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: the recrystallization time described in the described step 4) is 6～48h.
9. 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: solvent load is during recrystallization described in the described step 4): sample: ethanol: butanone=1g: 5ml: 5ml～1g: 5ml: 30ml.
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| CN102229633A (en) * | 2011-05-31 | 2011-11-02 | 江南大学 | Method for separating and preparing five high-purity anthocyanidin monomers from grape skins |
| CN104138367A (en) * | 2014-08-15 | 2014-11-12 | 江苏省中国科学院植物研究所 | Application of kosteletzkya malvidin in preparation of medicines for preventing and treating inflammation-related diseases |
| CN104177460A (en) * | 2014-07-17 | 2014-12-03 | 中国农业大学 | Preparation method of 3,5-disaccharide anthocyanin |
| CN108976268A (en) * | 2018-06-21 | 2018-12-11 | 湖南农业大学 | A method of preparing Vitis davidii Foex two main anthocyanin standard items |
| CN116333009A (en) * | 2023-02-24 | 2023-06-27 | 新疆科技学院 | Method for separating and purifying malvidin-3-O-glucoside from berberis thunbergii fruits |
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