CN104152508A - Method for direct extraction of genipin from waste liquid in gardenia yellow pigment production - Google Patents
Method for direct extraction of genipin from waste liquid in gardenia yellow pigment production Download PDFInfo
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Abstract
The invention relates to a method for direct extraction of genipin from a waste liquid in gardenia yellow pigment production. The method includes the following steps: A, concentrating the waste liquid in gardenia yellow pigment production to obtain a dilute extract; B, adding alcohol to precipitate out plenty of carbohydrate impurity precipitates, filtering, and conducting decompressing concentration to obtain an extract containing geniposide; C, dissolving the extract enriched with geniposide in a citric acid-sodium citrate buffer, adding acidic cellulase, and carrying out hydrolysis by continuous stirring; D, extracting the hydrolysate with an organic solvent under continuous stirring; E, decolorizing by with granular activated carbon; and F, crystallizing, recrystallizing and drying to obtain a finished product of genipin. The invention directly uses waste liquor from gardenia yellow pigment production as the raw material, and omits the extraction purification process of genipin; the invention uses different distribution coefficients of genipin and other compounds in a two-phase solvent, and employs a continuous dynamic extraction method, so as to reduce the consumption of solvent, shorten extraction time and obtain the optimal extraction effect.
Description
Technical field
The present invention relates to a kind of preparation method of genipin, the waste liquid that particularly a kind of direct utilization production Gardenia Yellow produces is prepared the method for genipin.
Background technology
Genipin (Genipin) is the product of Geniposide after enzymic hydrolysis, it is a kind of good natural biological linking agent, can with the crosslinked making biomaterials such as protein, collagen, gelatin and chitosan, as artificial skelecton, wound dressing material etc., its toxicity is far below glutaraldehyde and other conventional chemical cross-linking agents.Also can be used for treating hepatic diseases, step-down, defaecation etc.The result of study of a medical centre of Israel shows, genipin can be alleviated the symptom of type ii diabetes.Genipin also can be used as fingerprint collecting reagent and prepares the linking agent of immobilized enzyme.
The preparation method of genipin generally adopts and from cape jasmine, extracts Geniposide, then uses beta-glucoside enzymic hydrolysis, then adsorbs purification with macroporous resin and makes, and also can adopt microbe transformation method preparation.The preparation method of existing genipin has the following disadvantages: be all 1, to prepare genipin taking Geniposide as raw material, must first prepare Geniposide and could prepare genipin, preparation technology's relative complex.2, preparation process is used macroporous resin, the regenerative process of macroporous resin need to be used the solution such as acid, alkali on the one hand, environment is caused to certain pollution, the absorption refining effect of macroporous resin is not desirable especially on the other hand, the purification time is also relatively long, extend manufacture cycle, increase energy consumption, improve productive expense.
Summary of the invention
The technical problem to be solved in the present invention is: provide a kind of Geniposide that omits to extract purifying technique, the simple method of directly extracting genipin from the waste liquid of production Gardenia Yellow of technique, the method utilizes genipin to follow the partition ratio difference of other compound in two-phase solvent, adopt the method for continuous dynamic extraction, not only can obtain optimum extraction effect, can also reduce environmental pollution.
The technical scheme solving the problems of the technologies described above is: a kind of method of directly extracting genipin from the waste liquid of production Gardenia Yellow, comprises the following steps:
A, membrane concentration: concentrate by nanofiltration membrane producing the waste liquid that Gardenia Yellow produces, obtain solid quality content and be rare medicinal extract of 40～50%;
B, removal of impurities: adding the purity of 2～4 times of volumes of rare medicinal extract is more than 90% ethanol, make it separate out a large amount of carbohydrate contamination precipitations, filters, and filtrate decompression is condensed into the medicinal extract containing Geniposide 55～65%;
C, enzymolysis: it is 4.5～5 citric acid-sodium citrate damping fluid that the medicinal extract of getting enrichment Geniposide is dissolved in pH value, and the proportioning of medicinal extract and citric acid-sodium citrate damping fluid is: 1g:1～3ml; Add 0.3～0.8g acidic cellulase to add the active acidic cellulase for 10000U/g～30000U/g by 1g medicinal extract, under lasting stirring, be hydrolyzed, hydrolysis temperature is 30～40 DEG C, hydrolysis time 2～4h;
D, dynamically continuous extraction: hydrolyzed solution extracts with organic solvent under lasting stirring, extraction at every turn, the volume ratio of organic solvent and hydrolyzed solution is 1:1～3, extraction time 30～60 minutes, continuous extraction 2～4 times, combining extraction liquid;
E, decolouring: it is qualified decolouring to clear with granular carbon;
F, crystallization, recrystallization, dry: after extraction liquid concentrating under reduced pressure after decolouring is cooling, separate out genipin crude product, after filtration, genipin crude product is dissolved in to the organic solvent of 2～4 times of volumes of genipin crude product, concentrating under reduced pressure recrystallization after filtering, obtains finished product genipin after cryodrying;
Described organic solvent is propyl carbinol, primary isoamyl alcohol, methyl acetate or acetone, and step D is identical with the organic solvent using in step F.
In described C, enzymolysis step, hydrolysis is to carry out under rotating speed is the agitation condition of 40-70 rev/min.
Described D, dynamically in continuous extraction step, extraction is to carry out under rotating speed is the agitation condition of 100-120 rev/min.
In step F, the temperature of described cryodrying is 60～70 DEG C.
Further technical scheme of the present invention is: in steps A, producing the waste liquid that Gardenia Yellow produces, is to obtain by the following method:
(1) pure water lixiviate: clean cape jasmine is ground into the particle of 1～3mm, then adds the pure water of 8～12 times of cape jasmine weight, add polygalacturonase and proteolytic enzyme, lixiviate 2～3 times, each 2～4 hours, merges extracting solution at 45～55 DEG C of temperature;
(2) roughing out removal of impurities: extracting solution is separated with butterfly chip whizzer through dull and stereotyped whizzer, horizontal spiral centrifuge respectively successively;
(3) membrane sepn is purified: the extracting solution after the whizzer of three kinds of different sizes separates, and the inorganic ceramic micro-filtration membrane that is first 0.1～0.6um with aperture filters, 35～45 DEG C of service temperatures, pressure: 0.4～0.8Mpa; The filtrate obtaining is further filtered with the daltonian polysulphones hyperfiltration membrane of molecular weight cut-off 6000～10000,35～45 DEG C of service temperatures, pressure: 0.55～0.85Mpa; The filtrate obtaining is further filtered with the daltonian sulfonated polyether sulfone filtering film of molecular weight cut-off 500～700 more again, 40～50 DEG C of service temperatures, pressure: 1.5～2.5Mpa; Nanofiltration membrane is filtered the liquid of removing and is the waste liquid of producing Gardenia Yellow generation.
Owing to adopting technique scheme, the present invention has following beneficial effect:
1, directly with producing the waste liquid of Gardenia Yellow as raw material, omit Geniposide and extract purifying technique, relatively have efficiently with existing production technique and patented technology, technique is simple, equipment occupation space is little, be easy to realize the advantages such as continuous and automatic.
2, utilize genipin to follow the partition ratio difference of other compound in two-phase solvent, adopt the method for continuous dynamic extraction, solvent can Reusability, reduces the consumption of solvent, shortens extraction time, obtains optimum extraction effect; In addition, compared with using macroporous resin purification techniques with prior art, the solvent that dynamic extraction of the present invention uses on the one hand can repeatedly use, can omit the regenerating acid, the alkali lye that in the step of macroporous resin regeneration and regenerative process, use, reduce the pollution to environment, dynamic extraction of the present invention can shorten the production cycle on the other hand, reduces energy consumption, reduces production cost.
3, in technique, filter out the solvent that is applicable to concentration, adjust the potential of hydrogen (left and right, ph value=5) of solvent, can effectively improve the yield of genipin.
Below, the technical characterictic of the method for genipin of directly extracting from the waste liquid of production Gardenia Yellow to the present invention is further described in conjunction with the accompanying drawings and embodiments.
Brief description of the drawings
Fig. 1: the present invention's the Gardenia Yellow waste liquid that directly utilizes is prepared the process flow sheet of genipin.
Embodiment
Embodiment 1:
The waste liquid of producing Gardenia Yellow generation is concentrated by nanofiltration membrane, obtaining solid substance weight content is rare medicinal extract of 45% left and right, add 3 times of volume 95% ethanol to make it separate out a large amount of carbohydrate contamination precipitations, filter, filtrate decompression is condensed into the medicinal extract containing Geniposide 60% left and right.Get the medicinal extract 100g of enrichment Geniposide, be dissolved in 200ml, pH value is 4.5～5 citric acid-sodium citrate damping fluid, adding active is 20000U/g acidic cellulase 50g, be under 60 revs/min of conditions, to stir hydrolysis at rotating speed, 38 DEG C of hydrolysis temperatures, hydrolysis time 2 hours, then be to extract under 100 revs/min of conditions with the propyl carbinol of two volumes hydrolyzed solution at rotating speed at every turn, each extraction 30 minutes, continuous extraction 3 times, combining extraction liquid, it is qualified decolouring to clear with granular carbon.After extraction liquid concentrating under reduced pressure after decolouring is cooling, separate out genipin crude product, after filtration, genipin crude product is dissolved in to the propyl carbinol of 3 times of volumes, concentrating under reduced pressure recrystallization after filtering, can obtain the genipin 6.3g of purity >=98.4% after cryodrying, and productive rate is 6.3%.
Embodiment 2:
The waste liquid of producing Gardenia Yellow generation is concentrated by nanofiltration membrane, obtaining solid substance weight content is rare medicinal extract of 45% left and right, add 3 times of volume 95% ethanol to make it separate out a large amount of carbohydrate contamination precipitations, filter, filtrate decompression is condensed into the medicinal extract containing Geniposide 60% left and right.Get the medicinal extract 100g of enrichment Geniposide, be dissolved in 200ml, the citric acid-sodium citrate damping fluid that pH value is 4.5～5, adding active is 20000U/g acidic cellulase 50g, be under 60 revs/min of conditions, to stir hydrolysis at rotating speed, 38 DEG C of hydrolysis temperatures, hydrolysis time 2 hours, is then to extract under 100 revs/min of conditions with the primary isoamyl alcohol of two volumes hydrolyzed solution at rotating speed, each extraction 30 minutes, continuous extraction 3 times, combining extraction liquid, it is qualified decolouring to clear with granular carbon.After extraction liquid concentrating under reduced pressure after decolouring is cooling, separate out genipin crude product, after filtration, genipin crude product is dissolved in to the primary isoamyl alcohol of 3 times of volumes, concentrating under reduced pressure recrystallization after filtering, can obtain the genipin 5.1g of purity >=97.7% after cryodrying, and productive rate is 5.1%.
Embodiment 3:
The waste liquid of producing Gardenia Yellow generation is concentrated by nanofiltration membrane, obtaining solid substance weight content is rare medicinal extract of 45% left and right, add 3 times of volume 95% ethanol to make it separate out a large amount of carbohydrate contamination precipitations, filter, filtrate decompression is condensed into the medicinal extract containing Geniposide 60% left and right.Get the medicinal extract 100g of enrichment Geniposide, be dissolved in 200ml, the citric acid-sodium citrate damping fluid that pH value is 4.5～5, adding active is 20000U/g acidic cellulase 50g, be under 60 revs/min of conditions, to stir hydrolysis at rotating speed, 38 DEG C of hydrolysis temperatures, hydrolysis time 2 hours, is then to extract under 100 revs/min of conditions with the methyl acetate of two volumes hydrolyzed solution at rotating speed, each extraction 30 minutes, continuous extraction 3 times, combining extraction liquid, it is qualified decolouring to clear with granular carbon.After extraction liquid concentrating under reduced pressure after decolouring is cooling, separate out genipin crude product, after filtration, genipin crude product is dissolved in to the methyl acetate of 3 times of volumes, concentrating under reduced pressure recrystallization after filtering, can obtain the genipin 4.3g of purity >=98.4% after cryodrying, and productive rate is 4.3%.
Embodiment 4:
The waste liquid of producing Gardenia Yellow generation is concentrated by nanofiltration membrane, obtaining solid substance weight content is rare medicinal extract of 45% left and right, add 3 times of volume 95% ethanol to make it separate out a large amount of carbohydrate contamination precipitations, filter, filtrate decompression is condensed into the medicinal extract containing Geniposide 60% left and right.Get the medicinal extract 100g of enrichment Geniposide, be dissolved in 200ml, the citric acid-sodium citrate damping fluid that pH value is 4.5～5, adding active is 20000U/g acidic cellulase 50g, be under 60 revs/min of conditions, to stir hydrolysis at rotating speed, 38 DEG C of hydrolysis temperatures, hydrolysis time 2 hours, is then to extract under 100 revs/min of conditions with the acetone of two volumes hydrolyzed solution at rotating speed, each extraction 30 minutes, continuous extraction 3 times, combining extraction liquid, it is qualified decolouring to clear with granular carbon.After extraction liquid concentrating under reduced pressure after decolouring is cooling, separate out genipin crude product, after filtration, genipin crude product is dissolved in to the acetone of 3 times of volumes, concentrating under reduced pressure recrystallization after filtering, can obtain the genipin 5.4g of purity >=98.1% after cryodrying, and productive rate is 5.4%.
Embodiment 5:
The waste liquid of producing Gardenia Yellow generation is concentrated by nanofiltration membrane, obtain solid substance weight content and be 45% the rare medicinal extract in left and right, add 3 times of volume 95% ethanol to make it separate out a large amount of carbohydrate contamination precipitations, filter, filtrate decompression is condensed into the medicinal extract containing Geniposide 60% left and right.Get the medicinal extract 100g of enrichment Geniposide, be dissolved in 200ml, the citric acid-sodium citrate damping fluid that pH value is 4.5～5, adding active is 20000U/g acidic cellulase 50g, be under 60 revs/min of conditions, to stir hydrolysis at rotating speed, 38 DEG C of hydrolysis temperatures, hydrolysis time 4 hours, is then to extract under 100 revs/min of conditions with the propyl carbinol of two volumes hydrolyzed solution at rotating speed, each extraction 60 minutes, continuous extraction 4 times, combining extraction liquid, it is qualified decolouring to clear with granular carbon.After extraction liquid concentrating under reduced pressure after decolouring is cooling, separate out genipin crude product, after filtration, genipin crude product is dissolved in to the propyl carbinol of 3 times of volumes, concentrating under reduced pressure recrystallization after filtering, can obtain the genipin 8.1g of purity >=99.1% after cryodrying, and productive rate is 8.1%.
In various embodiments of the present invention, stirring velocity when stirring velocity when described hydrolysis and dynamic extraction can be according to practical situation adjustment, hydrolysis is generally to carry out under rotating speed is the agitation condition of 40-70 rev/min, and extraction is generally to carry out under rotating speed is the agitation condition of 100-120 rev/min.The temperature of described cryodrying is 60～70 DEG C.
The waste liquid that production Gardenia Yellow of the present invention produces is mainly to obtain by the following method:
(1) pure water lixiviate: clean cape jasmine is ground into the particle of 1～3mm, then adds the pure water of 8～12 times of cape jasmine weight, add polygalacturonase and proteolytic enzyme, lixiviate 2～3 times, each 2～4 hours, merges extracting solution at 45～55 DEG C of temperature;
(2) roughing out removal of impurities: extracting solution is separated with butterfly chip whizzer through dull and stereotyped whizzer, horizontal spiral centrifuge respectively successively;
(3) membrane sepn is purified: the extracting solution after the whizzer of three kinds of different sizes separates, and the inorganic ceramic micro-filtration membrane that is first 0.1～0.6um with aperture filters, 35～45 DEG C of service temperatures, pressure: 0.4～0.8Mpa; The filtrate obtaining is further filtered with the daltonian polysulphones hyperfiltration membrane of molecular weight cut-off 6000～10000,35～45 DEG C of service temperatures, pressure: 0.55～0.85Mpa; The filtrate obtaining is further filtered with the daltonian sulfonated polyether sulfone filtering film of molecular weight cut-off 500～700 more again, 40～50 DEG C of service temperatures, pressure: 1.5～2.5Mpa; Nanofiltration membrane is filtered the liquid of removing and is the waste liquid of producing Gardenia Yellow generation.
The present invention is applicable in addition to the above methods too, adopts additive method to produce the waste liquid that Gardenia Yellow produces.
Claims (5)
1. a method of directly extracting genipin from the waste liquid of production Gardenia Yellow, is characterized in that: comprise the following steps:
A, membrane concentration: concentrate by nanofiltration membrane producing the waste liquid that Gardenia Yellow produces, obtain solid substance weight content and be rare medicinal extract of 40～50%;
B, removal of impurities: adding the purity of 2～4 times of volumes of rare medicinal extract is more than 90% ethanol, make it separate out a large amount of carbohydrate contamination precipitations, filters, and filtrate decompression is condensed into the medicinal extract containing Geniposide 55～65%;
C, enzymolysis: it is 4.5～5 citric acid-sodium citrate damping fluid that the medicinal extract of getting enrichment Geniposide is dissolved in pH value, and the proportioning of medicinal extract and citric acid-sodium citrate damping fluid is: 1g:1～3ml; Add 0.3～0.8g acidic cellulase to add the active acidic cellulase for 10000U/g～30000U/g by 1g medicinal extract, under lasting stirring, be hydrolyzed, hydrolysis temperature is 30～40 DEG C, hydrolysis time 2～4h;
D, dynamically continuous extraction: hydrolyzed solution extracts with organic solvent under lasting stirring, extraction at every turn, the volume ratio of organic solvent and hydrolyzed solution is 1:1～3, extraction time 30～60 minutes, continuous extraction 2～4 times, combining extraction liquid;
E, decolouring: it is qualified decolouring to clear with granular carbon;
F, crystallization, recrystallization, dry: after extraction liquid concentrating under reduced pressure after decolouring is cooling, separate out genipin crude product, after filtration, genipin crude product is dissolved in to the organic solvent of 2～4 times of volumes of genipin crude product, concentrating under reduced pressure recrystallization after filtering, obtains finished product genipin after cryodrying;
Described organic solvent is propyl carbinol, primary isoamyl alcohol, methyl acetate or acetone, and step D is identical with the organic solvent using in step F.
2. the method for directly extracting genipin from produce the waste liquid of Gardenia Yellow according to claim 1, is characterized in that: in described C, enzymolysis step, hydrolysis is to carry out under rotating speed is the agitation condition of 40-70 rev/min.
3. the method for directly extracting genipin from produce the waste liquid of Gardenia Yellow according to claim 1, is characterized in that: described D, dynamically in continuous extraction step, extraction is to carry out under rotating speed is the agitation condition of 100-120 rev/min.
4. the method for directly extracting genipin from the waste liquid of production Gardenia Yellow according to claim 1, is characterized in that: in step F, the temperature of described cryodrying is 60～70 DEG C.
5. according to the method for directly extracting genipin from the waste liquid of production Gardenia Yellow described in claim 1-4 any one, it is characterized in that: in steps A, producing the waste liquid that Gardenia Yellow produces, is to obtain by the following method:
(1) pure water lixiviate: clean cape jasmine is ground into the particle of 1～3mm, then adds the pure water of 8～12 times of cape jasmine weight, add polygalacturonase and proteolytic enzyme, lixiviate 2～3 times, each 2～4 hours, merges extracting solution at 45～55 DEG C of temperature;
(2) roughing out removal of impurities: extracting solution is separated with butterfly chip whizzer through dull and stereotyped whizzer, horizontal spiral centrifuge respectively successively;
(3) membrane sepn is purified: the extracting solution after the whizzer of three kinds of different sizes separates, and the inorganic ceramic micro-filtration membrane that is first 0.1～0.6um with aperture filters, 35～45 DEG C of service temperatures, pressure: 0.4～0.8Mpa; The filtrate obtaining is further filtered with the daltonian polysulphones hyperfiltration membrane of molecular weight cut-off 6000～10000,35～45 DEG C of service temperatures, pressure: 0.55～0.85Mpa; The filtrate obtaining is further filtered with the daltonian sulfonated polyether sulfone filtering film of molecular weight cut-off 500～700 more again, 40～50 DEG C of service temperatures, pressure: 1.5～2.5Mpa; Nanofiltration membrane is filtered the liquid of removing and is the waste liquid of producing Gardenia Yellow generation.
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| CN105294640A (en) * | 2015-11-30 | 2016-02-03 | 云南麦瑞科生物科技有限公司 | Crystallization method of high-purity genipin |
| CN108794551A (en) * | 2018-08-28 | 2018-11-13 | 郑州中科新兴产业技术研究院 | A method of preparing high-purity gardenoside from gardenia yellow pigment waste liquor |
| CN113861253A (en) * | 2021-10-20 | 2021-12-31 | 广东省科学院测试分析研究所(中国广州分析测试中心) | Preparation method and application of genipin nucleotide monomer |
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| CN113861253A (en) * | 2021-10-20 | 2021-12-31 | 广东省科学院测试分析研究所(中国广州分析测试中心) | Preparation method and application of genipin nucleotide monomer |
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Address after: 545600 Luzhai County Industrial Park, Liuzhou City, Guangxi Zhuang Autonomous Region Patentee after: Guangxi Shanyun Biochemical Technology Co., Ltd. Address before: 545600 Luzhai County Industrial Park, Liuzhou City, Guangxi Zhuang Autonomous Region Patentee before: Guangxi Shanyun Biochemistry Technology Co., Ltd. |