CN104447270A - Method of purifying rheum emodin from by-product after extracting resveratrol from polygonum cuspidatum - Google Patents
Method of purifying rheum emodin from by-product after extracting resveratrol from polygonum cuspidatum Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/10—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
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Abstract
The invention discloses a method of purifying rheum emodin from a by-product after extracting resveratrol from polygonum cuspidatum. The method comprises the following steps: carrying out reflux extraction on an industrial by-product after extracting resveratrol from polygonum cuspidatum by ethyl acetate, and removing precipitates to obtain an extract at first; then adding an alkaline solution in the extract, extracting for many times, adding a potassium chloride saturated solution while extracting until layering, and combining the alkaline solution layers; then adding an acidic solution in the alkaline solution layers, carrying out suction filtration, collecting precipitates, and washing the precipitates by deionized water to obtain a rheum emodin crude product; finally crystallizing and re-crystallizing the rheum emodin crude product by virtue of an organic solvent, and volatilizing the solvent from the obtained crystal, thus obtaining a high-purity rheum emodin pure product. The invention provides an economic and efficient method of separating and enriching rheum emodin, so that the additional value of polygonum cuspidatum resources is increased, the deep development and utilization of the polygonum cuspidatum resources in China are promoted, environmental protection is promoted, and moreover, a reference is provided for increasing the profits of enterprises and solving the problem of rheum emodin treatment which plagues the enterprises for a long time.
Description
Technical field
The present invention relates to a kind of method of abstraction and purification functionality active component Schuttgelb from the industry byproduct after giant knotweed purification trans-resveratrol.
Technical background
Giant knotweed is polygonaceae (Polygonaceae) Polygonum (Polygonum) per nnial herb, the root and rhizome of giant knotweed (Polygonumcuspidatum Sieb.et Zucc.), main product in Jiangsu, Zhejiang, Anhui, Guangdong, Guangxi, Sichuan, Yunnan, Henan, Jiangxi, the ground such as Fujian.Giant knotweed contains number of chemical composition, as diphenylethylene (as trans-resveratrol etc.), Anthraquinones (as Schuttgelb etc.), phenols, flavonoid, polyose etc., there is analgesic therapy of invigorating blood circulation, clearing heat and promoting diuresis, the effect such as relieving cough and reducing sputum, tcm clinical practice be used for the treatment of jaundice due to damp-heat, cough due to lung-heat, sore and toxic, arthralgia, through diseases such as amenorrhoea pain, burn due to hot liquid or fire, wounies.
Schuttgelb is anthraquinone analog compound; be soluble in the organic solvents such as ethanol, acetone, ethyl acetate, chloroform; poorly water-soluble, has the effects such as antitumor, anti-inflammatory, antibacterial, immunomodulatory, protection liver kidney, anti-oxidant and scavenging free radicals, has very high pharmaceutical use.
Current China focuses mostly on in the research and development of trans-resveratrol for the research of giant knotweed.Investigation finds, containing Schuttgelb in the industry byproduct that enterprise produces in purification trans-resveratrol process, but because it is byproduct intensive amount relatively low (purity is approximately about 45%), utility value is also little, this industry byproduct containing Schuttgelb is all treated as refuse process by general enterprises, make Schuttgelb in giant knotweed fail to be utilized effectively, cause the waste of resource, and contaminate environment.
Reference:
[1] Xue Lan. pharmacological research progress [J] of Polygonum cuspidatum Sieb. et Zucc. CHINA JOURNAL OF CHINESE MATERIA MEDICA, 2000,25 (11): 651-653;
[2]KumarA,DhawansS,Aggarwal BB.Emodin(3-methyl-1,6,8-trihydroxyanthraquinone)inhibits TNF-induced NF-kB activation,IkB degradation,and expression of cellsurface adhesion protein in human vadcular endothlelical cells[J].Oncogene,1998,17(7)：913-918；
[3] Zhan Yutao, Wei Xinge, Chen Yingwei, etc. Schuttgelb is on the impact [J] of hepatic fibrosis rats Serum hyaluronic acid. combination of Chinese tradiational and Western medicine hepatopathy magazine, 1999,9 (4): 27;
[4] Liu Guanxian, Ye Rengao, Tan Zhiming, etc. Schuttgelb delays the research [J] of systemic lupus erythematosus kidney region fibrosis effect. Chinese experimental clinical immunology magazine, 1999,11 (3): 24-27;
[5]Huang SS,Yeh SF,Hong CY.Effect of anthraquinone derivatives on lipidperoxidation in rat heart mitochondria:Structure-activity relationship[J].J NatProd,1995,58(9)：1365-1371；
[6] Wu Jianxin, Xu Jiayu, Yuan Yaozong. the impact of Schuttgelb and Sandostatin on Pancreatic Ischemia in Acute Haemorrhagic Necrotizing Pancreatitis and mechanism [J]. Chinese combination of Chinese tradiational and Western medicine magazine, 1997,17 (6): 356-359.
Summary of the invention
Technical problem to be solved by this invention is, not enough for prior art, provides a kind of simple efficient, low cost and is suitable for the method extracting extraction purification Schuttgelb the byproduct after trans-resveratrol from giant knotweed of suitability for industrialized production.
For solving the problems of the technologies described above, the technical solution used in the present invention is: a kind of method extracting purifying Schuttgelb the byproduct after trans-resveratrol from giant knotweed, it comprises: first carry out refluxing extraction by ethyl acetate to from the industry byproduct after giant knotweed extraction trans-resveratrol, abandon precipitation, obtain extracting solution; In extracting solution, add basic solution again, repeatedly extract, while extraction, add saturated potassium chloride solution, until layering, merge basic solution layer; Then in basic solution layer, add acidic solution, suction filtration, precipitation is also cleaned with deionized water by collecting precipitation, obtains Schuttgelb crude product; Finally utilize organic solvent to carry out crystallization and recrystallization to Schuttgelb crude product, the crystal of acquisition volatilizes solvent, namely obtains highly purified Schuttgelb sterling.
More specifically step is as follows for the method for above-mentioned purifying Schuttgelb from the byproduct after giant knotweed extraction trans-resveratrol:
(1) refluxing extraction: adopt the ethyl acetate of 8 ~ 10 times amount to carry out refluxing extraction to extracting the industry byproduct after trans-resveratrol from giant knotweed, bath temperature be 80 ~ 90 DEG C (micro-boil); Time 3 ~ 4h, suction filtration, abandons precipitation, collect extracting solution, and by extracting solution water bath heat preservation, bath temperature is 85 ~ 95 DEG C.The ethyl acetate wherein used is analytical pure.
(2) alkali proposes extraction: extract extracting solution with the basic solution that 1.5 ~ 2.5 times amount mass percent concentrations are 4% ~ 8%, add the saturated potassium chloride solution of 0.1 ~ 0.3 times amount while extraction, until layering, collects basic solution layer.Continue extraction 2 ~ 3 times as stated above, merge basic solution layer.
Above-mentioned basic solution is the sodium carbonate of mass percent concentration 3% ~ 8%, sodium bicarbonate, SODIUM PHOSPHATE, MONOBASIC or disodium phosphate soln, and sodium carbonate, sodium bicarbonate, SODIUM PHOSPHATE, MONOBASIC and Sodium phosphate dibasic are all analytical pure.
(3) acid solution precipitation: adding mass percent concentration 5 ~ 10% acidic solution in extraction liquid, and constantly stir, is 2.0 ~ 4.5 to pH value, and room temperature leaves standstill 30 ~ 40mim, separates out precipitation.
Above-mentioned acidic solution is hydrochloric acid, sulfuric acid or the phosphoric acid solution of 5 ~ 10%, and hydrochloric acid, sulfuric acid and phosphoric acid are all analytical pure.
(4) collecting precipitation: remove supernatant liquor, careful collection precipitates, and carefully rinses precipitation 2 times with 2 ~ 3 times of deionized waters, makes precipitation dry, obtains Schuttgelb crude product.
Make the method for precipitation drying: lyophilize or oven drying.Cryodesiccated method is be deposited in-21 DEG C of pre-freeze 10-24h by what clean, under vacuum condition, on freeze drier, carries out lyophilize.The method of oven drying is for be placed in baking oven by precipitation, and temperature 40 ~ 50 DEG C, the time is 1 ~ 2h.
(6) crystallization and recrystallization: by Schuttgelb dissolving crude product in organic solvent, peak concentration dissolves, or rotary evaporation in vacuo (bath temperature is lower than 50 DEG C) is to just generating and precipitating, room temperature or putting into refrigerator carries out crystallization.After 3 ~ 7 days, during thing not regrowth to be crystallized, vacuum filtration, and carefully rinse crystal 2 times with 2 ~ 3 times of deionized waters, obtain Schuttgelb crystal.Obtained crystal can be carried out recrystallization as stated above, obtain more highly purified Schuttgelb crystal.
Above-mentioned organic solvent is methyl alcohol, glacial acetic acid, ethyl acetate, acetone.Methyl alcohol, glacial acetic acid, ethyl acetate, acetone are all analytical pure.
The invention has the advantages that with the byproduct in industrial production trans-resveratrol process as raw material; purifying is carried out to Schuttgelb wherein; establish the process for purification that trans-resveratrol produces Schuttgelb in byproduct; the purity of Schuttgelb is made significantly to be increased to more than 80%; not only increase the added value of giant knotweed resource; facilitate deep development and the utilization of China's giant knotweed resource, also help protection of the environment, and for increasing enterprise profit, solve puzzlement enterprise Schuttgelb process problem for a long time reference be provided.The present invention adopts solvent extraction process, alkali carries the heavy technique of acid, crystallization and recrystallizing technology, effectively improves extraction yield and the rate of recovery.The present invention adopts the low temperature treatment technology such as the evaporation of frozen drying, low-temperature rotary, normal temperature or refrigerator freezing crystallization, greatly reduces the degradation problem of Schuttgelb product.
The feature that the present invention is different from traditional extracting and developing and purification process is that the method operational condition is gentle, and production technique is simple, and the cycle is short, and organic solvent residual is low, and energy consumption is low, and production cost is low, the Schuttgelb outward appearance obtained and quality better.
Accompanying drawing explanation
Fig. 1 is present invention process schema.
Fig. 2 is that Schuttgelb product content analyzes HPLC collection of illustrative plates (glacial acetic acid).
Fig. 3 is that Schuttgelb product content analyzes HPLC collection of illustrative plates (methyl alcohol)
Fig. 4 is that Schuttgelb product content analyzes HPLC collection of illustrative plates (acetone)
Fig. 5 is that Schuttgelb product content analyzes HPLC collection of illustrative plates (ethyl acetate)
Embodiment
Below, the present invention will further illustrate with embodiment.
Embodiment 1:
Get trans-resveratrol and produce byproduct 100g, carry out refluxing extraction by the ethyl acetate of 800mL, bath temperature is 90 DEG C, extraction time 4h, filters, abandons precipitation, obtain extracting solution.With the water of 90 DEG C, water bath heat preservation is carried out to extracting solution.In extracting solution, add 4% sodium carbonate solution of 1.6L and the saturated potassium chloride solution of 80mL successively, after layering, collect sodium carbonate solution layer.And then in ethyl acetate layer, add 4% sodium carbonate solution of 800mL and the saturated potassium chloride solution of 80mL successively, until layering, collect sodium carbonate solution layer, abandon ethyl acetate layer, merge sodium carbonate solution layer solution.In sodium carbonate solution, adding 10%HCl solution, and constantly stir, is 2.0 to solution ph, leaves standstill 30min.Filter, precipitate 2 times with the deionized water wash of 70mL.Precipitation is placed in baking oven and carries out drying, drying temperature is 45 DEG C, and time of drying, 1h, precipitated heavy 37.64g.Dried precipitation glacial acetic acid peak concentration is dissolved, leaves standstill crystallization.Room temperature is placed, and ambient temperature is 25 DEG C ~ 30 DEG C, observes little orange-yellow needle crystal and generate after 1 day, and post crystallization growth in 4 days is no longer obvious, filters, and then uses the washed with de-ionized water crystallization 2 times of 40mL, the heavy 18.75g of crystal.Crystal glacial acetic acid peak concentration is dissolved, leaves standstill crystallization.Room temperature is placed, and ambient temperature is 25 DEG C ~ 30 DEG C, observes little orange-yellow needle crystal and generate after 1 day, and post crystallization growth in 4 days is no longer obvious.Filter, then use the washed with de-ionized water crystallization 2 times of 20mL, the heavy 9.01g of recrystallization crystal.
Product HPLC detection method is: chromatographic column: C18 reverse-phase chromatographic column (150mm × 4.6mm, 5 μm); Moving phase: methyl alcohol: 0.1% phosphoric acid (80:20); Flow velocity: 1ml/min; Column temperature: 30 DEG C; Determined wavelength: 254nm; Sample size: 10 μ L.Concrete operations are as follows: get 10mg Schuttgelb crystal, are dissolved in 50mL methanol solution, 0.45 μm of filtering with microporous membrane, get 10 μ L and detect.As shown in Figure 2, the content of Schuttgelb is 87.22% to detected result.
Embodiment 2:
Get trans-resveratrol and produce byproduct 0.5kg, carry out refluxing extraction by the ethyl acetate of 4.5L, bath temperature is 85 DEG C, extraction time 3.5h, filters, abandons residue, obtain extracting solution.With the water of 85 DEG C, water bath heat preservation is carried out to extracting solution.In extracting solution, add 6% sodium hydrogen carbonate solution of 9L and the saturated potassium chloride solution of 0.9L successively, after layering, collect sodium bicarbonate layer.Then in ethyl acetate layer, add 6% sodium hydrogen carbonate solution of 8L and the saturated potassium chloride solution of 0.8L successively, until layering, collect sodium bicarbonate layer.And then in ethyl acetate layer, add 6% sodium hydrogen carbonate solution of 7L and the saturated potassium chloride solution of 0.7L successively, until layering, collect sodium bicarbonate layer, abandon ethyl acetate layer, merge sodium bicarbonate layer solution.In sodium bicarbonate layer solution, add 6% sulphuric acid soln, be 3.5 to solution ph, leaves standstill 30min.Filter, precipitate 2 times with the deionized water wash of 300mL.Be deposited in-21 DEG C of pre-freeze 12h by what clean, under vacuum condition, on freeze drier, carry out lyophilize, the heavy 162.59g of precipitation.Dried precipitation methyl alcohol peak concentration is dissolved, leaves standstill crystallization.Room temperature is placed, and room temperature is 25 DEG C ~ 30 DEG C, observes little yellow needles and generate after 1 day, and post crystallization growth in 7 days is no longer obvious.Filter, then use the washed with de-ionized water crystallization 2 times of 150mL, the weight of crystal is 81.71g.Crystal methyl alcohol is carried out recrystallization as stated above, obtains recrystallization crystal.With 100mL washed with de-ionized water crystal 2 times, the weight of crystal is 52.24g.Product detects through HPLC, and as shown in Figure 3, detection method is identical with embodiment 1 for detected result, and the content of Schuttgelb is 82.22%.
Embodiment 3:
Get trans-resveratrol and produce byproduct 100g, carry out refluxing extraction by the ethyl acetate of 1L, bath temperature is 90 DEG C, extraction time 3h, filters, abandons residue, obtain extracting solution.With the water of 90 DEG C, water bath heat preservation is carried out to extracting solution.In extracting solution, add 8% sodium dihydrogen phosphate of 2.5L and the saturated potassium chloride solution of 0.3L successively, after layering, collect SODIUM PHOSPHATE, MONOBASIC layer.And then in ethyl acetate layer, add 8% sodium dihydrogen phosphate of 1.5L and the saturated potassium chloride solution of 0.3L successively, until layering, collect SODIUM PHOSPHATE, MONOBASIC layer, abandon ethyl acetate layer.Merge SODIUM PHOSPHATE, MONOBASIC layer solution.In SODIUM PHOSPHATE, MONOBASIC layer solution, adding 8% phosphoric acid solution, and constantly stir, is 4.5 to solution ph, leaves standstill 35min.Filtering-depositing, precipitates 2 times with the deionized water wash of 80mL.Be deposited in-21 DEG C of pre-freeze 12h by what clean, under vacuum condition, on freeze drier, carry out lyophilize, the heavy 33.59g of precipitation.Dried precipitation acetone peak concentration is dissolved, is statically placed in crystallization in-10 DEG C of refrigerators.Observe little orange-yellow needle crystal after 1 day to generate, post crystallization growth in 5 days no longer obviously time filter, then use the washed with de-ionized water crystallization 2 times of 40mL, the weight of crystal is 17.71g.Product detects through HPLC, and as shown in Figure 4, detection method is identical with embodiment 1 for detected result, and the content of Schuttgelb is 81.97%.
Embodiment 4:
Get trans-resveratrol and produce byproduct 200g, carry out refluxing extraction by the ethyl acetate of 2L, bath temperature is 80 DEG C, extraction time 4h, filters, abandons residue, obtain extracting solution.With the water of 80 DEG C, water bath heat preservation is carried out to extracting solution.In extracting solution, add 6% disodium phosphate soln of 5L and the saturated potassium chloride solution of 0.4L successively, after layering, collect Sodium phosphate dibasic layer.Continue extraction 2 times by above method, collect Sodium phosphate dibasic layer, abandon ethyl acetate layer.Merge Sodium phosphate dibasic layer solution, in Sodium phosphate dibasic layer solution, adding 8% phosphoric acid solution, and constantly stir, is 2.0 to pH value, leaves standstill 40min.Filtering-depositing, precipitates 2 times with the deionized water wash of 80mL.Be deposited in-21 DEG C of pre-freeze 12h by what clean, under vacuum condition, on freeze drier, carry out lyophilize, the heavy 81.71g of precipitation.By dried precipitation acetic acid ethyl dissolution, rotary evaporation in vacuo is to just generating precipitation, and bath temperature is 45 DEG C.By solution left standstill crystallization in-10 DEG C of refrigerators after allowing.Observe little orange-yellow needle crystal after 1 day to generate, post crystallization growth in 6 days no longer obviously time filter, then use the washed with de-ionized water crystallization 2 times of 120mL, the weight of crystal is 46.67g.By crystal with re-crystallizing in ethyl acetate once, filter after growth to be crystallized no longer obviously, with 40mL washed with de-ionized water crystallization 2 times, the weight of recrystallization crystal is 22.89g.Product detects through HPLC, and as shown in Figure 5, detection method is identical with embodiment 1 for detected result, and the content of Schuttgelb is 85.70%.
Claims (10)
1. extract a method for purifying Schuttgelb the byproduct after trans-resveratrol from giant knotweed, it is characterized in that comprising: first carry out refluxing extraction by ethyl acetate to from the industry byproduct after giant knotweed extraction trans-resveratrol, abandon precipitation, obtain extracting solution; In extracting solution, add basic solution again, repeatedly extract, while extraction, add saturated potassium chloride solution, until layering, merge basic solution layer; Then in basic solution layer, add acidic solution, suction filtration, precipitation is also cleaned with deionized water by collecting precipitation, obtains Schuttgelb crude product; Finally utilize organic solvent to carry out crystallization and recrystallization to Schuttgelb crude product, the crystal of acquisition volatilizes solvent, namely obtains highly purified Schuttgelb sterling.
2. a kind of method extracting purifying Schuttgelb the byproduct after trans-resveratrol from giant knotweed according to claim 1, is characterized in that concrete step is as follows:
1) adopt the ethyl acetate of 8 ~ 10 times amount to carry out refluxing extraction to from the industry byproduct after giant knotweed extraction trans-resveratrol, bath temperature is 80 ~ 90 DEG C, water bath time 3 ~ 4h, suction filtration, abandons precipitation, collects extracting solution, and by extracting solution water bath heat preservation, bath temperature is 85 ~ 95 DEG C;
2) with the basic solution that 1.5 ~ 2.5 times amount mass percent concentrations are 4% ~ 8%, extracting solution is extracted, add the saturated potassium chloride solution of 0.1 ~ 0.3 times amount while extraction, until layering, collect basic solution layer, according to said method continue extraction 2 ~ 3 times, merge basic solution layer;
3) in basic solution layer, adding the acidic solution that mass percent concentration is 5 ~ 10%, and constantly stir, is 2.0 ~ 4.5 to pH value, and room temperature leaves standstill 30 ~ 40mim, separates out precipitation;
4) remove supernatant liquor, careful collection precipitates, and carefully rinses precipitation 2 times with 2 ~ 3 times of deionized waters, makes precipitation dry, obtains Schuttgelb crude product;
5) by Schuttgelb dissolving crude product in organic solvent, peak concentration dissolves, or rotary evaporation in vacuo is to just generating precipitation, room temperature or putting into refrigerator carries out crystallization, after 3 ~ 7 days, during thing not regrowth to be crystallized, vacuum filtration, and carefully rinse crystal 2 times with 2 ~ 3 times of deionized waters, obtain Schuttgelb crystal.
3. a kind of method extracting purifying Schuttgelb the byproduct after trans-resveratrol from giant knotweed according to claim 2, it is characterized in that, obtained Schuttgelb crystal is carried out recrystallization by the method for above-mentioned steps (5), obtains more highly purified Schuttgelb crystal.
4. a kind of method extracting purifying Schuttgelb the byproduct after trans-resveratrol from giant knotweed according to claim 2, it is characterized in that, described ethyl acetate is analytical pure.
5. a kind of method extracting purifying Schuttgelb the byproduct after trans-resveratrol from giant knotweed according to claim 2, it is characterized in that, described basic solution is the sodium carbonate of mass percent concentration 3% ~ 8%, sodium bicarbonate, SODIUM PHOSPHATE, MONOBASIC or disodium phosphate soln, and sodium carbonate, sodium bicarbonate, SODIUM PHOSPHATE, MONOBASIC and Sodium phosphate dibasic are all analytical pure.
6. a kind of method extracting purifying Schuttgelb the byproduct after trans-resveratrol from giant knotweed according to claim 2, it is characterized in that, described acidic solution to be mass percent concentration be 5 ~ 10% hydrochloric acid, sulfuric acid or phosphoric acid solution, hydrochloric acid, sulfuric acid and phosphoric acid are all analytical pure.
7. a kind of method extracting purifying Schuttgelb the byproduct after trans-resveratrol from giant knotweed according to claim 2, it is characterized in that, the described method of precipitation drying that makes is freeze-drying, it is deposited in-21 DEG C of pre-freeze 10-24h by what clean, under vacuum condition, on freeze drier, carry out lyophilize.
8. a kind of method extracting purifying Schuttgelb the byproduct after trans-resveratrol from giant knotweed according to claim 2, it is characterized in that, described in make the method for precipitation drying be oven method, precipitation is placed in baking oven by it, temperature 40 ~ 50 DEG C, the time is 1 ~ 2h.
9. a kind of method extracting purifying Schuttgelb the byproduct after trans-resveratrol from giant knotweed according to claim 2, it is characterized in that, the bath temperature of described rotary evaporation in vacuo is lower than 50 DEG C.
10. a kind of method extracting purifying Schuttgelb the byproduct after trans-resveratrol from giant knotweed according to claim 1 and 2, it is characterized in that, described organic solvent is methyl alcohol, glacial acetic acid, ethyl acetate, acetone, and methyl alcohol, glacial acetic acid, ethyl acetate, acetone are all analytical pure.
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| CN101857538A (en) * | 2010-06-10 | 2010-10-13 | 成都市翻鑫家科技有限公司 | Method for extracting frangula emodin from giant knotweed |
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| US1844389A (en) * | 1928-08-15 | 1932-02-09 | Selden Co | Purification of anthraquinone |
| US3907836A (en) * | 1972-12-23 | 1975-09-23 | Bayer Ag | Process for purifying anthraquinone |
| CN102010316A (en) * | 2009-09-04 | 2011-04-13 | 中国药科大学 | Method for extracting high-purity frangula emodin from polygonum cuspidatum |
| CN101857538A (en) * | 2010-06-10 | 2010-10-13 | 成都市翻鑫家科技有限公司 | Method for extracting frangula emodin from giant knotweed |
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Application publication date: 20150325 |