CN103695494A - Method for integral preparation of products such as crocetin, genipin, gardenia blue and the like - Google Patents
Method for integral preparation of products such as crocetin, genipin, gardenia blue and the like Download PDFInfo
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- CN103695494A CN103695494A CN201310666965.XA CN201310666965A CN103695494A CN 103695494 A CN103695494 A CN 103695494A CN 201310666965 A CN201310666965 A CN 201310666965A CN 103695494 A CN103695494 A CN 103695494A
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Abstract
The invention relates to the fields of biotechnology and comprehensive utilization of a natural product, and particularly relates to a method for integral preparation of a plurality of products with high additional value, such as crocetin, genipin, gardenia blue and the like by taking jasmine as a raw material through crushing, alcohol extraction and concentration without complicated separation means of resin, silica gel and the like by adopting simple chemical modification and biological catalysis technologies through a set of production technology. The purities of the prepared crocetin and genipin can be up to over 95%, and the color value E590 of the gardenia blue is greater than 110.
Description
Technical field
The present invention relates to biotechnology and natural product comprehensive utilization field, be specifically related to a kind ofly take cape jasmine as the method for raw material integration system for multiple hi-tech value-added products such as bayer acid, genipin and gardenia blues.The method equipment requirements is low, easy and simple to handle, does not need through complex separations means such as resin, silica gel, can, in a set of technological process of production, produce multiple deep processed product simultaneously.
Background technology
cape jasmine (Gardenia jasminoides Ellis), has another name called SHANZHIZI, Yellow Fructus Gardeniae, red cape jasmine, white cicada etc., is a kind of evergreen shrubs of Rubiaceae Gardenia Ellis.Cape jasmine property bitter cold, nontoxic, is commonly used to heat-clearing and fire-purging, Xie Yu props up poison, clearing stomach gastral cavity blood etc.Modern pharmacology research shows, cape jasmine has the effects such as antipyretic calmness, hepatic cholagogic, is used for the treatment of clinically acute icterohepatitisshock, pain relieving, sprain and contusion, coronary heart disease etc.
the chemical composition of cape jasmine is comparatively complicated, reaches kind more than 100.Up to the present, from Gardenia Ellis plant, the compound of isolation identification has iridoids, flavonoid, organic acid ester, long chain alkane class etc.To the utilization of cape jasmine, be mainly to extract Gardenia Yellow and jasminoidin from cape jasmine fruit at present, and the deep processed product based on these two kinds of raw materials, as bayer acid, genipin and gardenia blue pigment etc.
the multiple pharmacological functions such as bayer acid is the product after Crocin hydrolysis, is one of effective constituent of Stigma Croci, has protection liver, suppresses tumour, anti-oxidant.But Stigma Croci is column cap to be used as medicine, and output is extremely low, because its resource is extremely limited, in China, be difficult to commerial growing again, cause its expensive being described as " plant gold ", there is high medical value.In cape jasmine, having in a large number Gardenia Yellow is a series of carotenoid derivatives, structurally to bayer acid and similar, so people to attempt adopting cape jasmine be that raw material is prepared the demand that bayer acid makes up market.
genipin (Genipin) is the product of jasminoidin after beta-glucoside 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.Meanwhile, pharmaceutical research shows, it has treatment hepatic diseases, alleviates the effect of the symptom of type ii diabetes.
gardenia blue pigment has strong coloring force, nature bright in colour, free from extraneous odour, heat-resisting, fast light, good stability, tone is not affected by pH value, to advantages such as human body have no side effect, the natural additive for foodstuff of current international popular, can also be for the dyeing of grade textiles, makeup etc.Its maximum absorption band adopt high-purity crystallized jasminoidin, suitable annesl enzyme, refining amino acid to prepare gardenia blue pigment, more than can reach 600nm; The price of this high-end gardenia blue is common variety 2-3 times in the world, can be described as a kind of hi-tech high value-added product.
Summary of the invention
the invention provides the method for directly utilizing cape jasmine fruit alcohol extract simultaneously to prepare the multiple products such as bayer acid, genipin and gardenia blue.The method equipment requirements is low, and operating process is easy, can produce the deep processed product of multiple high economic value added simultaneously, resource is received rational application, by maximization of economic benefit.
the object of the invention realizes by the following method: comprise the extraction of main component in cape jasmine fruit, the preparation of bayer acid and purifying, the preparation of the preparation of genipin and purifying and gardenia blue and refining these several partial contents.
(1) extraction of main component in cape jasmine fruit: cape jasmine fruit adopts 70-100% methanol solution to extract after pulverizing 20 orders, extracts and finishes the rear removal dregs of a decoction concentrated extracting solution.
(2) preparation of bayer acid and purifying: in concentrated solution, add highly basic, Stigma Croci methods of glycosides is wherein carried out to alkaline hydrolysis, filter and collect filter residue, filtrate for later use.Filter residue produces precipitation again add strong acid after buck fully dissolves after.Precipitation is bayer acid crude product after a large amount of clear water washings, and purity reaches more than 70%; Adopt ethanol, ethyl acetate, DMF bayer acid crude product to be carried out to recrystallization and purity can be promoted to more than 95%.
(3) preparation of genipin and purifying: will after the filtrate evaporate to dryness of alkaline hydrolysis reaction end gained, adopt pure water to redissolve, and build and stablize organic solvent/aqueous two phase system with organic solvent.In biphasic system, add the enzyme that can be hydrolyzed β (1-4) glycosidic link, and the factors such as the temperature of reaction process and pH of controlling are hydrolyzed to jasminoidin.After hydrolytic process finishes, separated organic phase solution concentrated evaporate to dryness, obtain genipin crude product, and purity reaches more than 60%.To crude product, adopt organic recrystallizations that carry out such as ethanol, acetone purity can be promoted to more than 95%.
(4) preparation of gardenia blue pigment and refining: the genipin crude product of preparation is after water redissolves, and the amino acid adding forms gardenia blue pigment crude product solution in the auxiliary lower complexing of ultrasonic wave; Adopt membrane separation technique to refine and can obtain high look valency gardenia blue pigment, look valency >110 the crude product solution of gardenia blue pigment.
during the invention process, comprise the steps: (1) cape jasmine fruit mistake 20 mesh sieves after crushed, adopt solvent to extract 3 times, it is 10-30% that the removal dregs of a decoction united extraction liquid are concentrated into solid content.Described solvent is that alcohol content is the methanol/water mixed solvent of 70-100%.
(2) in the extract after concentrated, add NaOH, KOH or Na
2
cO
3
deng, regulate extract solution pH within the scope of 9-11, adopt ultrasonic generator to react and carry out catalysis acceleration alkaline hydrolysis.The temperature of reaction process is controlled at 10-40 ℃, and ultrasonic frequency is 40kHz, and power is 50-100W, and the reaction times is 10-30 minute.
(3) after reaction finishes, by suction filtration, collect the tawny producing in solution and precipitate, filtrate for later use.
(4) getting tawny precipitation, to add pH be the buck of 9-11 until no longer dissolve, then add sour water to regulate pH between 3-4, until no longer produce brick-red precipitation.Buck used can be by NaOH, KOH or Na
2
cO
3
etc. water-soluble, be configured, sour water used is HCl or H
2
sO
4
.The brick-red precipitation of gained is bayer acid crude product after a large amount of clear water washings, and purity reaches more than 70%.
(5) bayer acid crude product being carried out to recrystallization can be promoted to purity more than 95%.Employing solvent is ethanol, ethyl acetate or DMF.
(6) will after the filtrate evaporate to dryness of alkaline hydrolysis reaction end gained, adopt pure water to redissolve, and build and stablize organic solvent/aqueous two phase system with organic solvent.Described organic solvent can be ethyl acetate, a kind of in sherwood oil or methylene dichloride.
(7) in biphasic system, add the enzyme that can be hydrolyzed β (1-4) glycosidic link, and adopt ultrasonic wave to accelerate the generation of enzyme digestion reaction, the temperature of reaction process is controlled at 40-55 ℃, adopting second acid for adjusting pH is 4.5-5.5, ultrasonic frequency is 40kHz, power is 50-100W, and the reaction times is 4 to 12 hours, and final transformation efficiency can reach more than 85%.The described enzyme that can be hydrolyzed β (1-4) glycosidic link can be β glucuroide (enzyme 2 wU alive, enzyme dosage is 0.5%), cellulase (enzyme 20 wU alive, enzyme dosage is 5%) or hemicellulase (enzyme 20 wU alive, enzyme dosage is 5%).
(8) organic layer of negate after should finishing, adopts after equal-volume pure water washing 3 times, and concentrated solvent evaporated, obtains genipin crude product, and purity reaches more than 75%.
(9) adopting organic solvent system to carry out recrystallization to genipin crude product can be increased to purity more than 95%.Described organic solvent system is a kind of in petroleum ether-ethyl acetate, sherwood oil-acetone, ethanol-water system.
(10) get genipin crude product and adopt pure water to redissolve, add can with the a-amino acid of genipin complexing, as one or more kilnitamins in L-glutamic acid, glycine, Methionin.Adopt ultrasonic wave to accelerate the complex reaction process of gardenia blue pigment, the temperature of reaction process is controlled at 40-55 ℃, and ultrasonic frequency is 40kHz, power is 50-100W, reaction times is 12 to 24 hours, gained gardenia blue solution, look valency E590>60.
(11) the gardenia blue solution reacting after finishing passes through membrane separation technique, and employing is held back aperture and removed small molecular weight impurity wherein and gardenia blue solution concentrated simultaneously at hollow cellulose film or the organic membrane of 3000-5000, until solid content surpasses 15 %.The spray-dried gardenia blue powder that obtains of gardenia blue solution after processing, look valency E590>110.
advantage of the present invention and positively effect: the present invention adopts Catalyzed by Ultrasonic Wave means are directly prepared the multiple high value added products such as bayer acid, genipin and gardenia blue by methods such as alkaline hydrolysis, enzymolysis from cape jasmine fruit simultaneously.
(1), due to complicated component in cape jasmine, it is by first extract Purification of Fructus Gardeniae yellow pigment (being Stigma Croci glycosides compound) from cape jasmine that traditional technology is prepared bayer acid, then prepares bayer acid through methods such as alkaline hydrolysis.This production process is complicated, complex operation, and production cost is higher.It is raw material by direct alcohol extract of take cape jasmine that this patent provides a kind of, by transesterification reaction, effectively Stigma Croci glycosides compound is formed to the precipitated product be insoluble to alcohol, then by filter and hydrolysis etc. extremely simple operation can obtain bayer acid crude product; A whole set of production technique has easy and simple to handle, with short production cycle, many-sided advantage such as reduces costs.
(2) the invention allows for the approach that the waste liquid that produces producing bayer acid fully utilizes.By adopting organic solvent/water biphasic catalysis method, can utilize the waste liquid that contains jasminoidin to prepare important biological medicine material genipin.The method is utilized the difference of jasminoidin and the genipin solubleness in different solvents, can effectively the product genipin of enzymatic reaction be enriched in organic phase, thereby make the content of genipin in water for a long time in lower level, play the effect that promotes that reaction occurs, improves transformation efficiency.Moreover, because can complex reaction occurring with the amino acid, protein etc. that exist in liquid environment, genipin forms pigment; Therefore, the present invention adopts the means of organic solvent/water biphasic catalysis to carry out this hydrolytic process, can effectively avoid reaction product genipin to contact with amino acid and protein in water, thereby guarantee the stable existence of product genipin, improve the yield of reaction.By the technology such as immobilized enzyme, produce genipin with tradition and compare, there is yield high, the advantage such as equipment requirements is low, easy and simple to handle.
(3) the present invention is applied to Catalyzed by Ultrasonic Wave in the production technique of cape jasmine deep processed product first, has effectively realized completing fast of the important reaction process of multistep wherein.For example, the alkaline hydrolysis of traditional Stigma Croci glycosides compound adopts thermal backflow method often to need a few hours just can react completely, and by ultrasonic wave auxiliary catalysis means, only needs to get final product for 1 hour termination reaction at normal temperatures; For another example, in existing technique, adopt β glucuroide often to need to continue 24 to 48 hours to the enzymolysis process of jasminoidin, and assist and reaction process can be shortened and completed within 6 to 12 hours by ultrasonic wave.Therefore, the present invention is applied to Catalyzed by Ultrasonic Wave in the production technique of cape jasmine deep processed product, has the shortening production cycle, reduces energy consumption, dwindles many-sided advantages such as cost.
accompanying drawing explanation:
fig. 1 is bayer acid standard substance liquid chromatograms.
fig. 2 is the bayer acid liquid chromatogram after exquisite recrystallization.
fig. 3 is genipin standard substance liquid chromatograms.
fig. 4 is the genipin liquid chromatogram after exquisite recrystallization.
embodiment:
the present invention can specifically implement by the technology illustrating in summary of the invention, and the example by below can conduct further description the present invention, yet scope of the present invention is not limited to following embodiment.
embodiment 1: the preparation of bayer acid.
(1) cape jasmine fruit 200g adopts 1000 ml methanol extraction 2 times after crushed, removes after filtration after the dregs of a decoction, and extracted twice liquid is merged and is concentrated into 200ml.
(2) in concentrated solution, adding NaOH to regulate pH is 10.0, is placed in ultrasonic generator and reacts.The temperature of reaction process is controlled at 28 ℃, and ultrasonic frequency is 40kHz, and power is 100W, and the reaction times is 10 minutes.
(3) after reaction finishes, by suction filtration, collect the tawny producing in solution and precipitate.
(4) getting tawny precipitation, to add pH be 10 buck 100 ml, after all dissolving, then adds the HCl aqueous solution of 2mol/L to regulate pH to 3, now in solution, produces a large amount of brick-red precipitations.The brick-red precipitation of gained is bayer acid crude product 1.7g after a large amount of clear water washings.
(5) get bayer acid crude product 100mg, at 65 ℃, adopt 20ml DMF to dissolve, and be concentrated into after original volume 1/3, at 4 ℃, carry out recrystallization, obtain crystallization bayer acid 36mg.
(6) bayer acid after adopting HPLC to recrystallization carries out purity detecting, and purity is more than 95%.
detected result is as shown in accompanying drawing 1,2.
embodiment 2: the preparation of genipin.
(1) get the methyl alcohol filtrate that 200 ml alkaline hydrolysis reactions finish gained, adopt 200ml pure water to redissolve after evaporate to dryness methyl alcohol, 1:1 adds ethyl acetate to build biphasic system by volume.
(2) in biphasic system, adding enzyme work is the middle temperature cellulase (consumption 5%) of 20wU, and is placed in ultrasonic generator and reacts, and the temperature of reaction process is controlled at 50 ℃, adopting second acid for adjusting pH is 4.5, ultrasonic frequency is 40kHz, and power is 100W, and the reaction times is 8 hours.
(3) organic layer of negate after should finishing, adopts after equal-volume pure water washing 3 times, and concentrated solvent evaporated, obtains genipin crude product 6.3 g, and purity reaches more than 75%.
(4) get genipin crude product 2.0 g, after adopting methanol-water system to dissolve at 50 ℃, put into 4 ℃ of refrigerators and carry out recrystallization, obtain crystallization genipin 1.3 g.
(5) genipin after adopting HPLC to recrystallization carries out purity detecting, and purity is 95～98%.
detected result is as shown in accompanying drawing 3,4.
embodiment 3: the preparation of gardenia blue pigment.
(1) get genipin crude product 100.0g, (content 75%) adopts 10L distilled water to dissolve.
(2) in the aqueous solution, adding 200.0g purity is more than 99% Sodium Glutamate, and is placed in ultrasonic generator and reacts, and the temperature of reaction process is controlled at 50 ℃, and ultrasonic frequency is 40kHz, and power is 100W, and the reaction times is 24 hours.After reaction finishes, gained solution is gardenia blue crude product aqueous solution solution, look valency E590>60.
(3) the gardenia blue crude product aqueous solution of reaction after finishing, adopt hold back aperture at the hollow cellulose film of 3000-5000, hold back concentrated, until stop when in trapped fluid, solid content surpasses 15%.
(4) spray-dried gardenia blue powder 164.7 g that obtain of trapped fluid, look valency E590>110.(look valency is measured and is carried out according to method in GB 28311-2012).
Claims (6)
1. one kind is utilized cape jasmine alcohol extract integration system for the method for the products such as bayer acid, genipin and gardenia blue, it is characterized in that: cape jasmine is pulverized by after ethanol-extracted, concentrating, concentrated solution is directly reached and is prepared trans-crocetin simultaneously separated with jasminoidin object by twice alkaline hydrolysis, then, further by water-organic solvent two-phase enzyme catalysis means hydrolysis jasminoidin, prepare genipin and gardenia blue pigment.
2. in claim 1, prepare in twice alkaline hydrolysis of trans-crocetin, alkaline hydrolysis is as follows for the first time: (1) cape jasmine fruit is crossed 20 mesh sieves after crushed, adopt under the methanol/water mixed solvent normal temperature that alcohol content is 70-100% and extract 3 times, remove the dregs of a decoction, united extraction liquid, and to be concentrated into solid content be 10-30%; (2) in the extract after concentrated, add NaOH, KOH or Na2CO3, regulate extract solution pH within the scope of 9-13, temperature is controlled at 20-60 ℃, and the time is 10-30 minute, and ultrasonic frequency is 40kHz, and power is the tawny precipitation of 20-100W suction filtration.
3. in claim 1, prepare in twice alkaline hydrolysis of trans-crocetin, alkaline hydrolysis is as follows for the second time: getting tawny precipitation, to add pH be that the buck of 9-11 is until no longer dissolve, add again sour water to regulate pH between 3-4, until no longer produce brick-red precipitation, be purity and reach more than 70% bayer acid crude product, buck used can be by water-soluble being configured such as NaOH, KOH or Na2CO3, and sour water used is HCl or the H2SO4 aqueous solution.
In claim 1 water-organic solvent biphasic catalysis system hydrolysis jasminoidin to prepare genipin method as follows: will isolate the filtrate evaporate to dryness of gained after trans-crocetin, employing pure water redissolves, and and ethyl acetate, a kind of structure in the organic solvent such as sherwood oil or methylene dichloride is stablized organic solvent/aqueous two phase system, in add the enzyme that can be hydrolyzed β (1-4) glycosidic link, and adopt ultrasonic wave to accelerate the generation of enzyme digestion reaction, the temperature of reaction process is controlled at 40-55 ℃, adopting second acid for adjusting pH is 4.5-5.5, reaction times is 4 to 12 hours, final transformation efficiency can reach more than 85%.
5. in claim 1, the preparation method of gardenia blue pigment is: get the filtrate of isolating gained after trans-crocetin, add enzyme and the L-glutamic acid that can be hydrolyzed β (1-4) glycosidic link, glycine, one or more kilnitamins in Methionin, reaction times is 12 to 24 hours, the employing of gained gardenia blue solution is held back aperture and is removed small molecular weight impurity wherein and gardenia blue solution concentrated simultaneously at hollow cellulose film or the organic membrane of 3000-5000, until solid content surpasses 15 %, the spray-dried gardenia blue powder that obtains, look valency E590>110.
6. the enzyme that can be hydrolyzed β (1-4) glycosidic link described in claim 4 and 5 can be β glucuroide (enzyme 2 wU alive, enzyme dosage is 0.5-5%), cellulase (enzyme 20 wU that live, enzyme dosage is 5-20%) or hemicellulase (enzyme 20 wU alive, enzyme dosage is 5-20%).
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Cited By (6)
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| CN104152508A (en) * | 2014-08-14 | 2014-11-19 | 广西山云生化科技有限公司 | Method for direct extraction of genipin from waste liquid in gardenia yellow pigment production |
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| CN105063119A (en) * | 2015-08-31 | 2015-11-18 | 桂林茗兴生物科技有限公司 | Method for extracting genipin from gardenias |
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| CN112608620A (en) * | 2014-10-30 | 2021-04-06 | 三荣源有限公司 | Method for removing geniposide, genipin or both |
| CN113817357A (en) * | 2021-09-27 | 2021-12-21 | 武汉淡雅香生物科技有限公司 | Natural pigment water-based ink for cigarette tipping paper and preparation method thereof |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104152508A (en) * | 2014-08-14 | 2014-11-19 | 广西山云生化科技有限公司 | Method for direct extraction of genipin from waste liquid in gardenia yellow pigment production |
| CN112608620A (en) * | 2014-10-30 | 2021-04-06 | 三荣源有限公司 | Method for removing geniposide, genipin or both |
| CN104480154A (en) * | 2014-12-30 | 2015-04-01 | 成都普思生物科技有限公司 | Method for separating and purifying crocetin monomer from crocus sativus |
| CN105063119A (en) * | 2015-08-31 | 2015-11-18 | 桂林茗兴生物科技有限公司 | Method for extracting genipin from gardenias |
| CN105063107A (en) * | 2015-08-31 | 2015-11-18 | 桂林茗兴生物科技有限公司 | Method for preparing crocetin through gardenias |
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| CN105063107B (en) * | 2015-08-31 | 2019-03-05 | 桂林三叶生物科技有限责任公司 | A method of preparing bayer acid from cape jasmine |
| CN113817357A (en) * | 2021-09-27 | 2021-12-21 | 武汉淡雅香生物科技有限公司 | Natural pigment water-based ink for cigarette tipping paper and preparation method thereof |
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