CN101585757A - Method for preparing curcumin, demethoxycurcumin and bisdemethoxycurcumin - Google Patents
Method for preparing curcumin, demethoxycurcumin and bisdemethoxycurcumin Download PDFInfo
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Abstract
The present invention discloses a method for preparing curcumin, demethoxycurcumin and bisdemethoxycurcumin, which comprises the following steps: continuously executing countercurrent extraction to the turmeric with the methanol-acid solution or ethanol-acid solution, after filtering the extracted solution, condensing into the oleoresin with the relative density of 0.9-1.2; placing the oleoresin on the chromatographic separation medium for gradient elution, and after fraction-collecting the eluent, respectively obtaining the curcumin crystal, demethoxycurcumin crystal and bisdemethoxycurcumin crystal after condensing. The invention adopts a technique in which HZ-816, HZ-818 or HZ-801 is used as the chromatographic separation medium and the alcohol-water is used as the elution solvent. Three monomeric compounds of curcumin, demethoxycurcumin and bisdemethoxycurcumin are simultaneously obtained. The purity of each monomeric compound is more than 95%, and the recovery rate of the sample is more than 70%. The method of the invention further has the advantages of less intercrossing of compounds in the separation process, short flow path, strong operability, low consumption of the solvent, high extraction rate and excellent stability of the extraction solution. Furthermore the obtained product can be widely applied for the fields of medicament, food, etc., and is suitable for large-scale production.
Description
Technical field
The invention belongs to field of phytochemistry, be specifically related to a kind of separation purification method that from turmeric, prepares high-purity curcumin, demethoxycurcumin and bisdemethoxycurcumin.
Background technology
Curcumine is a kind of phenol pigment that extracts from Zingiber curcuma turmeric rhizome, because its color and luster is stable and the very low (LD50 of mouse stomach＞2g/kg), be widely used in foodstuff additive and the dyestuff at present of toxicity.The yellow substance of turmeric is tart phenolic substance slightly, mainly contains 3 kinds of main components: curcumine I (47%); Curcumine II, i.e. demethoxycurcumin (17%); Curcumine III, i.e. bisdemethoxycurcumin (36%) has effects such as antitumor, anti-inflammatory, anti-oxidant and reducing blood-fat, and its structural formula is as follows:
Curcumine
Demethoxycurcumin
Bisdemethoxycurcumin
Preliminary study shows, turmeric yellow has blood vessel formation against function (Gururaj AE, BelakavadiM, Venkatesh DA, et al.Molecularmechanisms of anti-angiogenic effect ofcurcumin.Biochem Biophys Res Commun, 2002,297 (4): 934-942.), studies show that simultaneously, 3 kinds of monomeric anti-tumor activities of turmeric yellow comprise that the restraining effect to endothelial cell growth has notable difference, wherein the biological activity with curcumine III is the strongest, curcumine III has clear and definite inhibition A549 nude mouse in vivo and suppresses knurl growth and angiogenic action thereof, and traditional Chinese medicine turmeric source is abundant, and toxic side effect is little, is expected to become a kind of new type antineoplastic medicine of low toxic side effect.Along with the further understanding of people to curcumine, Demethoxycurcumin and the different pharmacologically actives of two Demethoxycurcumin monomeric compounds, the separation of monomeric compound will have very important meaning.
Since over the years, because the curcumine monomer is not easily separated and purify, adopted conventional resin to be difficult to turmeric yellow is carried out separation and purification, people mainly extract hybrid pigment from turmeric at present, and domestic do not have a monomeric preparation method of curcumine.United States Patent (USP) CPI (B) 930 reports are with the suitable organic solvent extraction of curcumine, extract is dissolved in and contains aqueous polar solvent, add excessive non-polar solvent, stir the back placement and obtain precipitation, throw out is added in acetone, ethanol or their mixture make it recrystallization; U.S. Pat 6224877 reports extract total curcumin with sodium salicylate solution, the turmeric meal of 5g being crossed 22 mesh sieves joins in the sodium salicylate solution of 100ml3.0mol/l, 30 ℃ were stirred 8 hours, filter, filtrate adds the dilution of 400ml water, obtain purity and be 90.1% total curcumin, yield is 48.11%.The multistage purifying of these leaching process general requirements, technology all belong to solvent and extract crystallization processes, and the quantity of solvent of use is big, and loss is big.Can only obtain total curcumin simultaneously and can not get each monomeric compound.
Chinese patent CN 1554634A discloses a kind of preparation method who extracts curcumine from turmeric, and turmeric is clean through washing, and after pulverizing, fermentation and the acid hydrolysis, centrifugation obtains the total curcumin product with N-BUTYL ACETATE from extraction, reextraction.
Chinese patent CN 10131799A discloses a kind of preparation method of effective component of turmeric, will add 70～95% extraction using alcohols after the turmeric pulverizing medicinal materials, ethanol water elution behind sample on the non-polar macroporous resin.Again by the industrial chromatography preparation, obtain total turmeric yellow behind the elutriant concentrate drying, content reaches 97.3%.Though this method prepares through industrial chromatography, but still can not obtain curcumine, demethoxycurcumin and three kinds of monomer pigments of bisdemethoxycurcumin.
Summary of the invention
The object of the invention provides a kind of favorable reproducibility, and is easy and simple to handle, the separation purification method for preparing three kinds of monomeric compounds of curcumine from turmeric that can accomplish scale production.
Be realization the object of the invention, the preparation method of this curcumine, demethoxycurcumin and the bisdemethoxycurcumin that the present invention relates to, its feature comprises the steps:
A extracts: the turmeric after will pulverizing is with Continuous Countercurrent Extraction under the methyl alcohol-aqueous acid of 50%～80% volumetric concentration of 2～6 times (v/w) or the ethanol-aqueous acid room temperature 3～6 hours, and being concentrated into relative density 50～70 ℃ of negative pressure behind the extracting liquid filtering is 0.9～1.2 oleo-resinous;
B chromatographic separation: above-mentioned curcumine oleo-resinous placed on HZ-816, HZ-818 or the HZ-801 chromatographic separation medium carry out gradient elution, carry out negative pressure behind the elutriant fraction collection respectively and concentrate, behind dehydrated alcohol band water, obtain curcumine, demethoxycurcumin and bisdemethoxycurcumin crystalline powder respectively.
Described methyl alcohol-aqueous acid is methyl alcohol and aqueous hydrochloric acid or the mixing solutions that constitutes with acetic acid aqueous solution; Described ethanol-aqueous acid is ethanol and aqueous hydrochloric acid or the mixed solution that constitutes with acetic acid aqueous solution, and the pH value of described methyl alcohol-aqueous acid or ethanol-aqueous acid is 4.0～5.5.
The spissated vacuum tightness of described negative pressure is-0.08～0.1Mpa.
The mass ratio of the applied sample amount of oleo-resinous and chromatographic separation medium is 1: 20～100 (W/W) in the described gradient elution.
The setting of described gradient eluent gradient is respectively the alcohol solution of volumetric concentration 40%～50%, 70%～80% alcohol solution and 85%～95% alcohol solution.The online detection of HPLC behind the elutriant fraction collection, HPLC content is merged respectively greater than 95% curcumine, demethoxycurcumin and bisdemethoxycurcumin, obtain curcumine elutriant, demethoxycurcumin elutriant and bisdemethoxycurcumin elutriant respectively, then with curcumine elutriant, demethoxycurcumin elutriant and bisdemethoxycurcumin elutriant respectively at 50～70 ℃ of following concentrating under reduced pressure, behind dehydrated alcohol band water, obtain curcumine, demethoxycurcumin and bisdemethoxycurcumin powder respectively.
The technical progress that the present invention obtains:
1) the present invention has abandoned traditional solvent extraction, technologies such as silica gel column chromatography, adopt superfine HZ-816, HZ-818 or HZ-801 are as the chromatographic separation medium, alcohol-water is as the separation-extraction technology of eluting solvent, simultaneously can obtain high-purity curcumin, demethoxycurcumin and three kinds of monomeric compounds of bisdemethoxycurcumin respectively, the purity HPLC purity of each monomeric compound can reach more than 95%, sample recovery rate is all more than 70%, and the intersection in the sepn process between the compound is less, flow process is brief, and is workable.
2) turmeric yellow of the present invention is comparatively carrying out the room temperature Continuous Countercurrent Extraction under the stable p H, solvent consumption is few, and (Continuous Countercurrent Extraction solvent for use amount is 4 times of turmeric weight, it is 20 times of curcumine weight that room temperature is extracted solvent load then), extraction yield height and extracting solution good stability, be applicable to scale operation, products obtained therefrom can be widely used in fields such as medicine, food.
Description of drawings
Fig. 1 is a curcumine oleo-resinous HPLC color atlas.
Fig. 2 separates the curcumine HPLC color atlas that obtains for chromatographic resin of the present invention.
Fig. 3 separates the demethoxycurcumin HPLC color atlas that obtains for chromatographic resin of the present invention.
Fig. 4 separates the bisdemethoxycurcumin HPLC color atlas that obtains for chromatographic resin of the present invention.
Embodiment
To further illustrate the present invention in following examples, these embodiment only are used to the present invention is described and to the present invention without limits.
Except that specifying, content alleged among the present invention is weight percentage, and the per-cent of turmeric yellow content is the area normalization method gained of HPLC.
Embodiment 1:
The a Continuous Countercurrent Extraction: after turmeric (available from Burma) is ground into 40～60 purpose curcuma powders, taking by weighing 4.0 kilograms, under the room temperature is methyl alcohol-4 hours after-filtration of HCL aqueous solution Continuous Countercurrent Extraction of 5.0 with 16L80%, pH value.(0.08～0.1Mpa) to be concentrated into relative density be 0.9 to gained filtrate, obtains curcumine oleo-resinous 200 grams 60 ℃ of down decompressions;
B chromatographic separation: the chromatographic column capital that above-mentioned curcumine oleo-resinous is splined on HZ-816 chromatographic resin (the resin volume is 6L), the chromatographic column column length is preferably 500～1200mm, present embodiment chromatographic column column length 1000mm, the chromatographic column internal diameter is preferably 80～160mm, present embodiment chromatographic column internal diameter is 140mm, and the mass ratio of the applied sample amount of curcumine oleo-resinous and chromatographic separation medium is 1: 100 (W/W).Be 50% methanol aqueous solution, 80% methanol aqueous solution and 90% methanol aqueous solution gradient elution with mobile phase volume concentration respectively then, each elution volume is 4 times (24L) of chromatographic column column volume, flow velocity be 1 column volume/hour.The high polarity impurity part of giving up 50% methanol aqueous solution wash-out behind the above-mentioned gradient elution, after the online detection of HPLC, collect the bisdemethoxycurcumin elutriant of 80% methanol aqueous solution wash-out, the demethoxycurcumin elutriant and the curcumine elutriant of 90% methanol aqueous solution wash-out respectively, and then HPLC content merged respectively greater than 95% curcumine elutriant, demethoxycurcumin elutriant and bisdemethoxycurcumin elutriant obtain highly purified curcumine, demethoxycurcumin and bisdemethoxycurcumin monomer elutriant.With three kinds of pigment monomer elutriants respectively at 60 ℃ of following concentrating under reduced pressure (0.08～0.1Mpa), behind dehydrated alcohol band water, obtain 14g curcumine imperfect crystal formation powder, 5.1g demethoxycurcumin imperfect crystal formation powder and 10.8g bisdemethoxycurcumin imperfect crystal formation powder respectively, each crystalline powder detects with HPLC respectively, content is all greater than 95%, each detected result is seen Fig. 2, Fig. 3, Fig. 4, and Fig. 1 is a curcumine oleo-resinous HPLC collection of illustrative plates.
Above liquid-phase condition is: waters2487 detector, 515 double pumps, λ=420nm, Hypersil C
18Post, 5um, 4.6x250mm.Moving phase: acetonitrile: water=55: 45.
Embodiment 2: the present embodiment difference from Example 1 is,
A Continuous Countercurrent Extraction: after turmeric (available from Burma) is ground into 40～60 purpose curcuma powders, take by weighing 5.0 kilograms, under the room temperature be methyl alcohol-6 hours after-filtration of HCL water Continuous Countercurrent Extraction of 5.0 with 20L80%, pH value, (0.08～0.1Mpa) to be concentrated into relative density be 1.2 to filtrate, obtains curcumine oleo-resinous 250 grams 60 ℃ of down decompressions.
The b chromatographic separation: above-mentioned curcumine oleo-resinous is splined on the chromatographic column capital of HZ-818 chromatographic resin (the resin volume is 8L), and chromatographic column column length 1000mm, internal diameter are 110mm.The mass ratio of curcumine oleo-resinous applied sample amount and chromatographic separation medium is 1: 100 (W/W).Be 50% aqueous ethanolic solution, 80% aqueous ethanolic solution and 90% ethanol water aqueous solution gradient elution with mobile phase volume concentration respectively then, each wash-out body is 4 times (32L) of chromatographic column column volume, flow velocity be 1 column volume/hour.The high polarity impurity part of giving up 50% aqueous ethanolic solution wash-out behind the above-mentioned gradient elution, after the online detection of HPLC, collect the bisdemethoxycurcumin elutriant of 80% aqueous ethanolic solution wash-out, the demethoxycurcumin elutriant and the curcumine elutriant of 90% aqueous ethanolic solution wash-out respectively.Obtain highly purified curcumine, demethoxycurcumin and bisdemethoxycurcumin monomer elutriant after again HPLC content being merged respectively greater than above-mentioned each elutriant of 95%.With three kinds of pigment monomer elutriants respectively at 60 ℃ of following concentrating under reduced pressure (0.08～0.1Mpa), behind dehydrated alcohol band water, obtain 17.6g curcumine imperfect crystal formation powder respectively, 6.4g demethoxycurcumin imperfect crystal formation powder, 13.5g bisdemethoxycurcumin imperfect crystal formation powder.Each crystalline powder detects through HPLC respectively, and content is all greater than 95%, and each detected result is seen Fig. 2～Fig. 4.
Embodiment 3:
A Continuous Countercurrent Extraction: after turmeric (available from Burma) is ground into 40～60 purpose curcuma powders, take by weighing 10.0 kilograms, be that ethanol-HCL aqueous solution of 5.0 carries out 5 hours after-filtration of Continuous Countercurrent Extraction with 40L80%, pH value under the room temperature, (0.08～0.1Mpa) to be concentrated into relative density be 1.1 to filtrate, obtains curcumine oleo-resinous 500 grams 60 ℃ of down decompressions.
The b chromatographic separation: above-mentioned curcumine oleo-resinous is splined on the chromatographic column capital of HZ-801 chromatographic resin (the resin volume is 16L), and chromatographic column column length 1200mm, internal diameter are 200mm.The mass ratio of curcumine oleo-resinous applied sample amount and chromatographic separation medium is 1: 100 (W/W).Be 50% methanol aqueous solution, 80% methanol aqueous solution and 90% methanol aqueous solution gradient elution with mobile phase volume concentration respectively then, each elution volume is 4 times (64L) of chromatographic column column volume, flow velocity be 1 column volume/hour.The high polarity impurity part of giving up 50% methanol aqueous solution wash-out behind the above-mentioned gradient elution, after the online detection of HPLC, collect the bisdemethoxycurcumin elutriant of 80% methanol aqueous solution wash-out, the demethoxycurcumin elutriant and the curcumine elutriant of 90% methanol aqueous solution wash-out respectively.Obtain highly purified curcumine, demethoxycurcumin and bisdemethoxycurcumin monomer elutriant after HPLC content merged respectively greater than above-mentioned each elutriant of 95%.With three kinds of pigment monomer elutriants respectively at 60 ℃ of following concentrating under reduced pressure (0.08～0.1Mpa), behind dehydrated alcohol band water, obtain 36.4g curcumine imperfect crystal formation powder respectively, 13.4g demethoxycurcumin imperfect crystal formation powder, 28.8g bisdemethoxycurcumin imperfect crystal formation powder.Crystalline powder detects through HPLC respectively, and content is all greater than 95%, and each detected result is seen Fig. 2～Fig. 4.
Embodiment 4:
A Continuous Countercurrent Extraction: after turmeric (available from Burma) is ground into 40～60 purpose curcuma powders, take by weighing 10.0 kilograms, under the room temperature be ethanol-4 hours after-filtration of HCL aqueous solution Continuous Countercurrent Extraction of 5.0 with 40L80%, pH value, (0.08～0.1Mpa) to be concentrated into relative density be 1.0 to filtrate, obtains curcumine oleo-resinous 490 grams 60 ℃ of down decompressions.
The b chromatographic separation: above-mentioned curcumine oleo-resinous is splined on the chromatographic column capital of HZ-818 chromatographic resin (the resin volume is 16L), and chromatographic column column length 1200mm, internal diameter are 200mm.The mass ratio of curcumine oleo-resinous applied sample amount and chromatographic separation medium is 1: 100 (W/W).Be 50% aqueous ethanolic solution, 80% aqueous ethanolic solution and 90% aqueous ethanolic solution gradient elution with mobile phase volume concentration respectively then, each elution volume is 4 times (64L) of column volume, flow velocity be 1 column volume/hour.The high polarity impurity part of giving up 50% aqueous ethanolic solution wash-out behind the above-mentioned gradient elution, after the online detection of HPLC, collect the bisdemethoxycurcumin elutriant of 80% aqueous ethanolic solution wash-out, the demethoxycurcumin elutriant and the curcumine elutriant of 90% aqueous ethanolic solution wash-out respectively.Obtain highly purified curcumine, demethoxycurcumin and bisdemethoxycurcumin monomer elutriant after HPLC content merged respectively greater than above-mentioned each elutriant of 95%.With three kinds of pigment monomer elutriants respectively at 60 ℃ of following concentrating under reduced pressure (0.08～0.1Mpa), behind dehydrated alcohol band water, obtain 35.8g curcumine imperfect crystal formation powder respectively, 13.2g demethoxycurcumin imperfect crystal formation powder, 27.6g bisdemethoxycurcumin imperfect crystal formation powder.Crystalline powder detects through HPLC respectively, and content is all greater than 95%, and each detected result is seen embodiment 1HPLC collection of illustrative plates.
Chromatographic resin HZ-816, HZ-818, the HZ-801 that adopts in the various embodiments described above is the 80-100 purpose chromatographic resin that Shanghai China shake chemical plant produces.
Claims (5)
1. the preparation method of a curcumine, demethoxycurcumin and bisdemethoxycurcumin is characterized in that it may further comprise the steps:
A extracts: the turmeric after will pulverizing is with Continuous Countercurrent Extraction under the methyl alcohol-aqueous acid of 50%～80% volumetric concentration of 2～6 times (v/w) or the ethanol-aqueous acid room temperature 3～6 hours, and being concentrated into relative density 50～70 ℃ of negative pressure behind the extracting liquid filtering is 0.9～1.2 oleo-resinous;
B chromatographic separation: above-mentioned curcumine oleo-resinous placed on HZ-816, HZ-818 or the HZ-801 chromatographic separation medium carry out gradient elution, carry out negative pressure behind the elutriant fraction collection respectively and concentrate, behind dehydrated alcohol band water, obtain curcumine, demethoxycurcumin and bisdemethoxycurcumin crystalline powder respectively.
2. the preparation method of curcumine according to claim 1, demethoxycurcumin and bisdemethoxycurcumin is characterized in that described methyl alcohol-aqueous acid is methyl alcohol and aqueous hydrochloric acid or the mixing solutions that constitutes with acetic acid aqueous solution; Described ethanol-aqueous acid is ethanol and aqueous hydrochloric acid or the mixed solution that constitutes with acetic acid aqueous solution, and the pH value of described methyl alcohol-aqueous acid or ethanol-aqueous acid is 4.0～5.5.
3. the preparation method of curcumine according to claim 1, demethoxycurcumin and bisdemethoxycurcumin is characterized in that the spissated vacuum tightness of described negative pressure is-0.08～0.1Mpa.
4. the preparation method of curcumine according to claim 1, demethoxycurcumin and bisdemethoxycurcumin is characterized in that the applied sample amount of oleo-resinous in the described gradient elution and the mass ratio of chromatographic separation medium are 1: 20～100 (W/W).
5. according to the preparation method of claim 1,2,3 or 4 described curcumines, demethoxycurcumin and bisdemethoxycurcumin, it is characterized in that the setting of described gradient eluent gradient is respectively the alcohol solution of volumetric concentration 40%～50%, 70%～80% alcohol solution and 85%～95% alcohol solution.
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| CN102603505A (en) * | 2012-02-09 | 2012-07-25 | 徐宏永 | Method for extracting and separating high-purity curcumin with low heavy-metal residues from turmeric |
| CN103193610A (en) * | 2013-04-11 | 2013-07-10 | 南京慧博生物科技有限公司 | Preparation method for extracting purified curcumin-related compounds from turmeric |
| CN104591987A (en) * | 2013-11-01 | 2015-05-06 | 山东大学（威海） | Preparation method for curcumin, demethoxycurcumin and bisdemethoxycurcumin |
| CN105669410A (en) * | 2016-01-14 | 2016-06-15 | 北京联合大学 | Method for extracting curcumin from turmeric |
| CN107286702A (en) * | 2017-07-28 | 2017-10-24 | 湖北紫鑫生物科技有限公司 | A kind of method that different tone Gardenia Yellows are separated in the dry fruit from Gardenia Yellow |
| CN109970531A (en) * | 2019-04-30 | 2019-07-05 | 广州市科虎生物技术研究开发中心 | A kind of curcumin high extraction preparation method |
| CN111440056A (en) * | 2020-05-12 | 2020-07-24 | 江苏慧博生物科技有限公司 | Preparation method for extracting total curcumin with high yield |
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| CN114539043A (en) * | 2022-03-08 | 2022-05-27 | 晨光生物科技集团股份有限公司 | Preparation method and application of demethoxycurcumin crystal |
| US11434189B1 (en) | 2021-10-20 | 2022-09-06 | I-Mei Foods Co., Ltd. | Method for isolating curcuminoids from turmeric rhizome |
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| CN102603505A (en) * | 2012-02-09 | 2012-07-25 | 徐宏永 | Method for extracting and separating high-purity curcumin with low heavy-metal residues from turmeric |
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| CN104591987A (en) * | 2013-11-01 | 2015-05-06 | 山东大学（威海） | Preparation method for curcumin, demethoxycurcumin and bisdemethoxycurcumin |
| CN105669410A (en) * | 2016-01-14 | 2016-06-15 | 北京联合大学 | Method for extracting curcumin from turmeric |
| CN105669410B (en) * | 2016-01-14 | 2018-05-11 | 北京联合大学 | A kind of method that curcumin is extracted from turmeric |
| CN107286702A (en) * | 2017-07-28 | 2017-10-24 | 湖北紫鑫生物科技有限公司 | A kind of method that different tone Gardenia Yellows are separated in the dry fruit from Gardenia Yellow |
| CN113727723A (en) * | 2018-11-03 | 2021-11-30 | 奥莱妮生命科学私人有限公司 | Method for preparing herbal extracts and compositions thereof |
| CN109970531B (en) * | 2019-04-30 | 2022-03-01 | 广州市科虎生物技术有限公司 | High-extraction-rate curcumin preparation method |
| CN109970531A (en) * | 2019-04-30 | 2019-07-05 | 广州市科虎生物技术研究开发中心 | A kind of curcumin high extraction preparation method |
| CN111440056A (en) * | 2020-05-12 | 2020-07-24 | 江苏慧博生物科技有限公司 | Preparation method for extracting total curcumin with high yield |
| CN112521259A (en) * | 2020-12-24 | 2021-03-19 | 晨光生物科技集团股份有限公司 | Preparation method of natural curcumin without vanillin |
| WO2022232482A1 (en) * | 2021-04-30 | 2022-11-03 | Majeed, Muhammed | Compositions for management of polycystic ovary syndrome |
| US11434189B1 (en) | 2021-10-20 | 2022-09-06 | I-Mei Foods Co., Ltd. | Method for isolating curcuminoids from turmeric rhizome |
| CN114539043A (en) * | 2022-03-08 | 2022-05-27 | 晨光生物科技集团股份有限公司 | Preparation method and application of demethoxycurcumin crystal |
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