CN104152508B - The method directly extracting genipin from the waste liquid producing Gardenia Yellow - Google Patents
The method directly extracting genipin from the waste liquid producing Gardenia Yellow Download PDFInfo
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- CN104152508B CN104152508B CN201410399596.7A CN201410399596A CN104152508B CN 104152508 B CN104152508 B CN 104152508B CN 201410399596 A CN201410399596 A CN 201410399596A CN 104152508 B CN104152508 B CN 104152508B
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Abstract
The present invention relates to a kind of directly utilizing and produce the method that gardenia yellow pigment waste liquor prepares genipin.Comprise the following steps: A, by produce Gardenia Yellow produce waste liquid be concentrated to give dilute extractum；B, addition ethanol make it separate out a large amount of saccharide contamination precipitation, and filtration, concentrating under reduced pressure become the extractum Han geniposide；C, the extractum taking enrichment geniposide are dissolved in citric acid sodium citrate buffer solution, add acidic cellulase, are hydrolyzed under continuous stirring；D, hydrolyzed solution extract with organic solvent under continuous stirring；E, use granular active carbon decoloring；F, through crystallization, recrystallization, dry, obtain finished product genipin.The present invention directly extracts purifying technique with the waste liquid producing Gardenia Yellow as raw material, omission geniposide；And utilize genipin different with other compound partition coefficient in two-phase solvent, the method using continuous dynamic extraction, reduces the consumption of solvent, shortens extraction time, it is thus achieved that optimum extraction effect.
Description
Technical field
The present invention relates to the preparation method of a kind of genipin, produce, particularly to a kind of directly utilizing, the method that the waste liquid of Gardenia Yellow generation prepares genipin.
Background technology
Genipin (Genipin) is geniposide product after enzyme hydrolysis, it it is a kind of excellent natural biological cross-linking agent, can cross-link with protein, collagen, gelatin and chitosan etc. and make biomaterial, such as artificial skelecton, wound dressing materials etc., its toxicity is far below glutaraldehyde and other conventional chemical cross-linking agents.Can also be used for treating hepatic disease, blood pressure lowering, relieving constipation etc..The result of study of one medical centre of Israel shows, genipin can alleviate the symptom of type ii diabetes.Genipin also can be used as fingerprint collecting reagent and prepares the cross-linking agent of immobilized enzyme.
The preparation method of genipin typically uses extraction geniposide from Fructus Gardeniae, then uses beta-glucosidase enzyme hydrolysis, then carries out absorption purification with macroporous resin and prepares, it would however also be possible to employ be prepared by microbe transformation method.The preparation method of existing genipin has the following disadvantages: 1, be all to prepare genipin with geniposide for raw material, i.e. must first prepare geniposide and could prepare genipin, and preparation technology is relative complex.2, preparation process uses macroporous resin, on the one hand the regenerative process of macroporous resin needs to use the solution such as acid, alkali, environment is caused certain pollution, on the other hand the absorption refining effect of macroporous resin is not especially desirable, the purification time is the most relatively long, extend manufacture cycle, increase energy consumption, improve producing cost.
Summary of the invention
The technical problem to be solved in the present invention is: provides one to omit geniposide and extracts purifying technique, technique simply directly extracts the method for genipin from the waste liquid producing Gardenia Yellow, the method utilizes genipin different with other compound partition coefficient in two-phase solvent, the method using continuous dynamic extraction, it is possible not only to obtain optimum extraction effect, it is also possible to reduce environmental pollution.
The technical scheme solving above-mentioned technical problem is: a kind of method directly extracting genipin from the waste liquid producing Gardenia Yellow, comprises the following steps:
A, membrance concentration: the waste liquid producing Gardenia Yellow generation is concentrated by NF membrane, obtains dilute extractum that solid quality content is 40～50%；
B, remove impurity: add the ethanol that purity is more than 90% of dilute extractum 2～4 times of volumes so that it is separate out a large amount of saccharide contamination precipitation, filter, and filtrate reduced in volume becomes containing geniposide 55～the extractum of 65%；
C, enzymolysis: the extractum taking enrichment geniposide is dissolved in the citric acid-sodium citrate buffer that pH value is 4.5～5, and extractum with the proportioning of citric acid-sodium citrate buffer is: 1g:1～3ml；Adding by 1g extractum and add the acidic cellulase that activity is 10000U/g～30000U/g based on 0.3～0.8g acidic cellulase, be hydrolyzed under continuous stirring, hydrolysis temperature is 30～40 DEG C, hydrolysis time 2～4h；
D, dynamic continuous extraction: hydrolyzed solution extracts with organic solvent under continuous stirring, extracts every time, organic solvent is 1:1～3 with the volume ratio of hydrolyzed solution, extraction time 30～60 minutes, continuous extraction 2～4 times, combining extraction liquid；
E, decolouring: be qualified with granular active carbon decoloring to clear；
F, crystallization, recrystallization, it is dried: after the cooling of extract concentrating under reduced pressure after decolouring, separate out genipin crude product, after filtration, genipin crude product is dissolved in genipin crude product 2～the organic solvent of 4 times of volumes, concentrating under reduced pressure recrystallization after filtration, after cold drying, obtains finished product genipin；
Described organic solvent is n-butyl alcohol, isoamyl alcohol, methyl acetate or acetone, and step D is identical with the organic solvent used in step F.
In described C, enzymolysis step, hydrolysis is to carry out under the stirring condition that rotating speed is 40-70 rev/min.
In described D, dynamic continuous extraction step, extraction is to carry out under the stirring condition that rotating speed is 100-120 rev/min.
In step F, the temperature of described cold drying is 60～70 DEG C.
The further technical scheme of the present invention is: in step A, produces the waste liquid that Gardenia Yellow produces, is to obtain by the following method:
(1) pure water extraction: clean gardenia powder is broken into the granule of 1～3mm, is subsequently adding Fructus Gardeniae weight 8～the pure water of 12 times, adds pectase and protease, extracts 2～3 times, each 2～4 hours, merged by extracting solution at temperature 45～55 DEG C；
(2) crude separation remove impurity: extracting solution is sequentially passed through respectively plate centrifuge, horizontal spiral centrifuge and tab (s) formula centrifuge and separates；
(3) membrance separation purifies: the extracting solution after the centrifuge of three kinds of different sizes separates, and first filters with the inorganic ceramic micro-filtration membrane that aperture is 0.1～0.6um, operation temperature 35～45 DEG C, pressure: 0.4～0.8Mpa；The filtrate obtained is filtered further with the daltonian polysulphones hyperfiltration membrane of molecular cut off 6000～10000, operation temperature 35～45 DEG C, pressure: 0.55～0.85Mpa；The filtrate obtained further is filtered with the daltonian sulfonated polyether sulfone filtering film of molecular cut off 500～700 again, operation temperature 40～50 DEG C, pressure: 1.5～2.5Mpa；The liquid that nanofiltration membrane is removed is and produces the waste liquid that Gardenia Yellow produces.
Owing to using technique scheme, the method have the advantages that
1, directly with producing the waste liquid of Gardenia Yellow as raw material, omit geniposide and extract purifying technique, compare with existing production technology and patented technology have efficiently, technique is simple, equipment occupation space is little, be easily achieved the advantages such as continuous and automatic.
2, utilizing genipin different with other compound partition coefficient in two-phase solvent, the method using continuous dynamic extraction, solvent with Reusability, can reduce the consumption of solvent, shorten extraction time, it is thus achieved that optimum extraction effect；Additionally, compared with using macroporous resin purification technique with prior art, the solvent that on the one hand dynamic extraction of the present invention uses can repeatedly use, can omit macroporous resin regeneration step and regenerative process in use regenerated acid, alkali liquor, decrease the pollution to environment, dynamic extraction the most of the present invention can shorten the production cycle, reduces energy consumption, reduces production cost.
3, filter out the solvent of applicable concentration in process, adjust the acid-base value (about ph value=5) of solvent, the yield of genipin can be effectively improved.
Below, in conjunction with the accompanying drawings and embodiments the technical characteristic of the method directly extracting genipin from the waste liquid producing Gardenia Yellow of the present invention is further described.
Accompanying drawing explanation
The gardenia yellow pigment waste liquor that directly utilizes of Fig. 1: the present invention prepares the process chart of genipin.
Detailed description of the invention
Embodiment 1:
The waste liquid producing Gardenia Yellow generation is concentrated by NF membrane, obtain dilute extractum that solid content weight content is about 45%, adding 3 times of volume 95% ethanol makes it separate out a large amount of saccharide contamination precipitation, filters, and filtrate reduced in volume becomes the extractum containing geniposide about 60%.Take the extractum 100g of enrichment geniposide, being dissolved in 200ml, pH value is the citric acid-sodium citrate buffer of 4.5～5, and adding activity is 20000U/g acidic cellulase 50g, stirring hydrolysis under the conditions of rotating speed is 60 revs/min, hydrolysis temperature 38 DEG C, hydrolysis time 2 hours, then extract under the conditions of rotating speed is 100 revs/min with the n-butyl alcohol of two volumes hydrolyzed solution every time, extraction 30 minutes every time, continuous extraction 3 times, combining extraction liquid, is qualified with granular active carbon decoloring to clear.Separate out genipin crude product after extract concentrating under reduced pressure cooling after decolouring, after filtration, genipin crude product is dissolved in the n-butyl alcohol of 3 times of volumes, concentrating under reduced pressure recrystallization after filtration, the genipin 6.3g of purity >=98.4% can be obtained after cold drying, productivity is 6.3%.
Embodiment 2:
The waste liquid producing Gardenia Yellow generation is concentrated by NF membrane, obtain dilute extractum that solid content weight content is about 45%, adding 3 times of volume 95% ethanol makes it separate out a large amount of saccharide contamination precipitation, filters, and filtrate reduced in volume becomes the extractum containing geniposide about 60%.Take the extractum 100g of enrichment geniposide, being dissolved in 200ml, pH value is the citric acid-sodium citrate buffer of 4.5～5, and adding activity is 20000U/g acidic cellulase 50g, stirring hydrolysis under the conditions of rotating speed is 60 revs/min, hydrolysis temperature 38 DEG C, hydrolysis time 2 hours, then extract under the conditions of rotating speed is 100 revs/min with the isoamyl alcohol of two volumes hydrolyzed solution, extraction 30 minutes every time, continuous extraction 3 times, combining extraction liquid, is qualified with granular active carbon decoloring to clear.Separate out genipin crude product after extract concentrating under reduced pressure cooling after decolouring, after filtration, genipin crude product is dissolved in the isoamyl alcohol of 3 times of volumes, concentrating under reduced pressure recrystallization after filtration, the genipin 5.1g of purity >=97.7% can be obtained after cold drying, productivity is 5.1%.
Embodiment 3:
The waste liquid producing Gardenia Yellow generation is concentrated by NF membrane, obtain dilute extractum that solid content weight content is about 45%, adding 3 times of volume 95% ethanol makes it separate out a large amount of saccharide contamination precipitation, filters, and filtrate reduced in volume becomes the extractum containing geniposide about 60%.Take the extractum 100g of enrichment geniposide, being dissolved in 200ml, pH value is the citric acid-sodium citrate buffer of 4.5～5, and adding activity is 20000U/g acidic cellulase 50g, stirring hydrolysis under the conditions of rotating speed is 60 revs/min, hydrolysis temperature 38 DEG C, hydrolysis time 2 hours, then extract under the conditions of rotating speed is 100 revs/min with the methyl acetate of two volumes hydrolyzed solution, extraction 30 minutes every time, continuous extraction 3 times, combining extraction liquid, is qualified with granular active carbon decoloring to clear.Separate out genipin crude product after extract concentrating under reduced pressure cooling after decolouring, after filtration, genipin crude product is dissolved in the methyl acetate of 3 times of volumes, concentrating under reduced pressure recrystallization after filtration, the genipin 4.3g of purity >=98.4% can be obtained after cold drying, productivity is 4.3%.
Embodiment 4:
The waste liquid producing Gardenia Yellow generation is concentrated by NF membrane, obtain dilute extractum that solid content weight content is about 45%, adding 3 times of volume 95% ethanol makes it separate out a large amount of saccharide contamination precipitation, filters, and filtrate reduced in volume becomes the extractum containing geniposide about 60%.Take the extractum 100g of enrichment geniposide, being dissolved in 200ml, pH value is the citric acid-sodium citrate buffer of 4.5～5, and adding activity is 20000U/g acidic cellulase 50g, stirring hydrolysis under the conditions of rotating speed is 60 revs/min, hydrolysis temperature 38 DEG C, hydrolysis time 2 hours, then extract under the conditions of rotating speed is 100 revs/min with the acetone of two volumes hydrolyzed solution, extraction 30 minutes every time, continuous extraction 3 times, combining extraction liquid, is qualified with granular active carbon decoloring to clear.Separate out genipin crude product after extract concentrating under reduced pressure cooling after decolouring, after filtration, genipin crude product is dissolved in the acetone of 3 times of volumes, concentrating under reduced pressure recrystallization after filtration, the genipin 5.4g of purity >=98.1% can be obtained after cold drying, productivity is 5.4%.
Embodiment 5:
The waste liquid producing Gardenia Yellow generation is concentrated by NF membrane, obtain the dilute extractum in left and right that solid content weight content is 45%, adding 3 times of volume 95% ethanol makes it separate out a large amount of saccharide contamination precipitation, filters, and filtrate reduced in volume becomes the extractum containing geniposide about 60%.Take the extractum 100g of enrichment geniposide, being dissolved in 200ml, pH value is the citric acid-sodium citrate buffer of 4.5～5, and adding activity is 20000U/g acidic cellulase 50g, stirring hydrolysis under the conditions of rotating speed is 60 revs/min, hydrolysis temperature 38 DEG C, hydrolysis time 4 hours, then extract under the conditions of rotating speed is 100 revs/min with the n-butyl alcohol of two volumes hydrolyzed solution, extraction 60 minutes every time, continuous extraction 4 times, combining extraction liquid, is qualified with granular active carbon decoloring to clear.Separate out genipin crude product after extract concentrating under reduced pressure cooling after decolouring, after filtration, genipin crude product is dissolved in the n-butyl alcohol of 3 times of volumes, concentrating under reduced pressure recrystallization after filtration, the genipin 8.1g of purity >=99.1% can be obtained after cold drying, productivity is 8.1%.
In various embodiments of the present invention, mixing speed during described hydrolysis and mixing speed during dynamic extraction can adjust according to practical situation, hydrolysis is usually and carries out under the stirring condition that rotating speed is 40-70 rev/min, and extraction is usually and carries out under the stirring condition that rotating speed is 100-120 rev/min.The temperature of described cold drying is 60～70 DEG C.
The waste liquid that production Gardenia Yellow of the present invention produces, mainly obtains by the following method:
(1) pure water extraction: clean gardenia powder is broken into the granule of 1～3mm, is subsequently adding Fructus Gardeniae weight 8～the pure water of 12 times, adds pectase and protease, extracts 2～3 times, each 2～4 hours, merged by extracting solution at temperature 45～55 DEG C；
(2) crude separation remove impurity: extracting solution is sequentially passed through respectively plate centrifuge, horizontal spiral centrifuge and tab (s) formula centrifuge and separates；
(3) membrance separation purifies: the extracting solution after the centrifuge of three kinds of different sizes separates, and first filters with the inorganic ceramic micro-filtration membrane that aperture is 0.1～0.6um, operation temperature 35～45 DEG C, pressure: 0.4～0.8Mpa；The filtrate obtained is filtered further with the daltonian polysulphones hyperfiltration membrane of molecular cut off 6000～10000, operation temperature 35～45 DEG C, pressure: 0.55～0.85Mpa；The filtrate obtained further is filtered with the daltonian sulfonated polyether sulfone filtering film of molecular cut off 500～700 again, operation temperature 40～50 DEG C, pressure: 1.5～2.5Mpa；The liquid that nanofiltration membrane is removed is and produces the waste liquid that Gardenia Yellow produces.
Present invention is equally applicable in addition to the above methods, use additive method to produce the waste liquid that Gardenia Yellow produces.
Claims (4)
1. the method directly extracting genipin from the waste liquid producing Gardenia Yellow, it is characterised in that: comprise the following steps:
A, membrance concentration: the waste liquid producing Gardenia Yellow generation is concentrated by NF membrane, obtains dilute extractum that solid content weight content is 40～50%；
B, remove impurity: add the ethanol that purity is more than 90% of dilute extractum 2～4 times of volumes so that it is separate out a large amount of saccharide contamination precipitation, filter, and filtrate reduced in volume becomes containing geniposide 55～the extractum of 65%；
C, enzymolysis: the extractum taking enrichment geniposide is dissolved in the citric acid-sodium citrate buffer that pH value is 4.5～5, and extractum with the proportioning of citric acid-sodium citrate buffer is: 1g:1～3ml；Adding by 1g extractum and add the acidic cellulase that activity is 10000U/g～30000U/g based on 0.3～0.8g acidic cellulase, be hydrolyzed under continuous stirring, hydrolysis temperature is 30～40 DEG C, hydrolysis time 2～4h；
D, dynamic continuous extraction: hydrolyzed solution extracts with organic solvent under continuous stirring, extracts every time, organic solvent is 1:1～3 with the volume ratio of hydrolyzed solution, extraction time 30～60 minutes, continuous extraction 2～4 times, combining extraction liquid；
E, decolouring: be qualified with granular active carbon decoloring to clear；
F, crystallization, recrystallization, it is dried: after the cooling of extract concentrating under reduced pressure after decolouring, separate out genipin crude product, after filtration, genipin crude product is dissolved in genipin crude product 2～the organic solvent of 4 times of volumes, concentrating under reduced pressure recrystallization after filtration, after cold drying, obtains finished product genipin；
Described organic solvent is n-butyl alcohol, isoamyl alcohol, methyl acetate or acetone, and step D is identical with the organic solvent used in step F；
In step A, produce the waste liquid that Gardenia Yellow produces, be to obtain by the following method:
(1) pure water extraction: clean gardenia powder is broken into the granule of 1～3mm, is subsequently adding Fructus Gardeniae weight 8～the pure water of 12 times, adds pectase and protease, extracts 2～3 times, each 2～4 hours, merged by extracting solution at temperature 45～55 DEG C；
(2) crude separation remove impurity: extracting solution is sequentially passed through respectively plate centrifuge, horizontal spiral centrifuge and tab (s) formula centrifuge and separates；
(3) membrance separation purifies: the extracting solution after the centrifuge of three kinds of different sizes separates, and first filters with the inorganic ceramic micro-filtration membrane that aperture is 0.1～0.6um, operation temperature 35～45 DEG C, pressure: 0.4～0.8Mpa；The filtrate obtained is filtered further with the daltonian polysulphones hyperfiltration membrane of molecular cut off 6000～10000, operation temperature 35～45 DEG C, pressure: 0.55～0.85Mpa；The filtrate obtained further is filtered with the daltonian sulfonated polyether sulfone filtering film of molecular cut off 500～700 again, operation temperature 40～50 DEG C, pressure: 1.5～2.5Mpa；The liquid that nanofiltration membrane is removed is and produces the waste liquid that Gardenia Yellow produces.
The method directly extracting genipin from the waste liquid producing Gardenia Yellow the most according to claim 1, it is characterised in that: in described C, enzymolysis step, hydrolysis is to carry out under the stirring condition that rotating speed is 40-70 rev/min.
The method directly extracting genipin from the waste liquid producing Gardenia Yellow the most according to claim 1, it is characterised in that: in described D, dynamic continuous extraction step, extraction is to carry out under the stirring condition that rotating speed is 100-120 rev/min.
The method directly extracting genipin from the waste liquid producing Gardenia Yellow the most according to claim 1, it is characterised in that: in step F, the temperature of described cold drying is 60～70 DEG C.
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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 |
| CN108794551B (en) * | 2018-08-28 | 2020-09-15 | 郑州中科新兴产业技术研究院 | Method for preparing high-purity geniposide from gardenia yellow pigment waste liquid |
| 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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| WO2008116319A1 (en) * | 2007-03-27 | 2008-10-02 | The Royal Institution For The Advancement Of Learning/Mcgill University | Bioproduction of ferulic acid and uses thereof |
| CN102925508A (en) * | 2011-08-10 | 2013-02-13 | 浙江毕尔锐思生物技术股份有限公司 | Method for preparing iridoid aglycone |
| CN103305555B (en) * | 2013-06-28 | 2014-12-31 | 西安纽赛生物科技有限公司 | Method for converting geniposide into genipin |
| CN103525883B (en) * | 2013-10-23 | 2015-06-03 | 宁德师范学院 | Method for preparing high-color-value gardenia blue pigment |
| CN103695494B (en) * | 2013-12-11 | 2016-06-22 | 中华全国供销合作总社南京野生植物综合利用研究所 | A kind of integration system is for the method for the products such as bayer acid, genipin and gardenia blue |
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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. |