CN104356184A - Method for separating and purifying geniposide by using isopropanol-salt double-aqueous-phase system - Google Patents

Method for separating and purifying geniposide by using isopropanol-salt double-aqueous-phase system Download PDF

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CN104356184A
CN104356184A CN201410721860.4A CN201410721860A CN104356184A CN 104356184 A CN104356184 A CN 104356184A CN 201410721860 A CN201410721860 A CN 201410721860A CN 104356184 A CN104356184 A CN 104356184A
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jasminoidin
salt
phase system
double
separation
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CN104356184B (en
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张红萍
李婷
李永斌
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Shaoyang University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification
    • C07H1/08—Separation; Purification from natural products

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Abstract

The invention relates to a method for separating and purifying geniposide by using an isopropanol-salt double-aqueous-phase system. The invention provides an efficient and gentle method for separating and purifying geniposide by using a double-aqueous-phase technique. The method comprises the following steps: producing a waste gardenia yellow liquid from a cape jasmine fruit raw material, performing extraction separation and concentration drying on the waste gardenia yellow liquid by using the isopropanol-salt double-aqueous-phase system, thereby obtaining a primary geniposide crystal product, and further recrystallizing, thereby obtaining geniposide crystal of which the purity is greater than 98.5%. By adopting the method, a natural geniposide product with high purity is separated and purified from a medical resource for both food and medicine. The method is simple and convenient to operate, environmentally friendly, high in efficiency, economical, time-saving and easy to amplify. The method is not only used for widening the double-aqueous-phase system for extracting geniposide and improving the efficiency in separating and purifying geniposide, but also is used for extracting and producing other pigments.

Description

The method of a kind of Virahol-salt double-aqueous phase system separation and purification jasminoidin
Technical field
The invention belongs to the technical field that natural product active ingredient extracts, be specifically related to a kind of method of high yield and purity extraction jasminoidin from cape jasmine fruit.
Background technology
Jasminoidin is a kind of effective constituent in cape jasmine fruit, has the effects such as anti-oxidant, anti-inflammatory, extensive application in medicine, health care, biological detection etc.Jasminoidin is iridoid glycoside compounds, different name Geniposide.Mainly natural edible coloring agent gardenia blue and gardenia red can be made in foodstuffs industry.In the 56 kinds of pigments listed in China GB2760-2007 " foodstuff additive use hygienic standard ", cyanine only has gardenia blue pigment and phycocyanin (i.e. Phycocyanins, C-pigment) two kinds.At present, at home and abroad all supply falls short of demand on market for natural blue pigment, and therefore active development high efficiency extraction jasminoidin technology, will have great realistic meaning and considerable market outlook.The China that is extracted in about jasminoidin has patent report, but the method for these patents uses Flavonoids by Macroporous Adsorption Resin to prepare jasminoidin mostly.As patent CN1939458A adopts macroporous absorption to prepare Fructus Gardeniae extract, because the remaining inert solvent of macroporous adsorbent resin endoporus is high, pre-treatment difficulty is large, and desorb is insufficient, affects separating effect, and resin regeneration difficulty, production cost increases.And the same model resin that same manufacturing enterprise produces, between each batch, greatly, poor reproducibility in separation and purification, is unfavorable for continuous prodution for specific surface area and functional group content difference.Double-aqueous phase system (ATPE) has easy to operate with it, separation efficiency is high, to many characteristics such as separate substance zero destructions, is widely used in product separation and the extraction in the fields such as biological chemistry, cytobiology and biochemical industry.Although existing bibliographical information utilizes ethanol/dipotassium hydrogen phosphate double-aqueous phase system to carry out the research of jasminoidin extraction, the jasminoidin purity obtained only has 62.12%, and yield is 96.32%.The factor affecting double-aqueous phase system extraction efficiency mainly contains solvent species, the kind of salt and the mass ratio of solvent and salt.Even if same double-aqueous phase system extraction different substances time, because the structures and characteristics of extract is on the impact of dissolution with solvents ability, the solvent in its system and the mass ratio of salt also variant.Virahol has the advantages such as inexpensive, low toxicity, viscosity are less, utilizes Virahol to make extraction agent and inorganic salt at present and forms double-aqueous phase system separation and purification jasminoidin there is not been reported.For this reason, we by Virahol with the stability of the double-aqueous phase system of sylvite, sodium salt and ammonium salt and study the alkoxide ratio in system and pH value, set up the Virahol/salt double water-phase new system of separation and purification jasminoidin.The method is easy and simple to handle, green high-efficient, and economy saves time, be easy to amplification.It has not only widened the double-aqueous phase system kind of extraction jasminoidin, improve the efficiency of jasminoidin separation and purification, and this technique also can be applicable to extraction and the production of other pigments.
Summary of the invention
The object of this invention is to provide a kind of method utilizing aqueous two phase extraction technique height yield and purity to extract jasminoidin.Utilize cape jasmine fruit raw material production Gardenia Yellow waste liquid, it is obtained jasminoidin crystallization first product through Virahol-salt double-aqueous phase system extracting and separating, concentrate drying, then after recrystallization, obtains high-purity gardenoside crystal.
The method of described a kind of separation and purification jasminoidin, is characterized in that: prepare Virahol and salt double-aqueous phase system under room temperature and drawing diagram, determines that the double-aqueous phase system be suitable for is Virahol/salt double-aqueous phase system according to one-tenth phase stability.
The method of described a kind of separation and purification jasminoidin, is characterized in that: the salt drawing double-aqueous phase system phasor used is sylvite, sodium salt or ammonium salt.Described sylvite is K 2hPO 4, K 2cO 3, KCl; Sodium salt is Na 2cO 3, NaCl, Na 2sO 4; Ammonia salt is NH 4cl, (NH 4) 2sO 4, NH 4hCO 3deng.
The method of described a kind of separation and purification jasminoidin, it is characterized in that: under room temperature, prepare Virahol and sodium salt double-aqueous phase system, Gardenia Yellow waste liquid is joined this double-aqueous phase system, at 10 ~ 50 DEG C, temperature constant magnetic stirring 30 ~ 60min under 300r/min condition, regulate pH simultaneously, make jasminoidin enrichment, leave standstill 60 ~ 100min, through the centrifugal 20 ~ 40min of 1000 ~ 2000rpm, isolate jasminoidin enrichment phase, at-0.04 ~-0.09MPa, under 20 ~ 90 DEG C of conditions, obtain jasminoidin crystal crude product through vacuum rotating concentrate drying.Carry out recrystallization with organic solvent, obtain highly purified jasminoidin crystal.
The method of described a kind of separation and purification jasminoidin, it is characterized in that described Virahol and sodium salt double-aqueous phase system specifically can be Virahol and sodium carbonate, described sodium carbonate and Virahol mass percent can be 5% ~ 30%, and system pH can be 9 ~ 12.
The method of described a kind of separation and purification jasminoidin, it is characterized in that the solvent of described recrystallization specifically can be in acetone, ethyl acetate or sherwood oil any one, the volume of described recrystallization solvent is 4 ~ 10 times of the first quality of jasminoidin.
The present invention utilizes Virahol-salt Two-phase system separation and purification Gardenia Yellow waste liquid, obtains high-purity gardenoside crystal through recrystallization with high yield.The method is easy and simple to handle, green high-efficient, and economy saves time, be easy to amplification.It has not only widened the double-aqueous phase system kind of extraction jasminoidin, improve the efficiency of jasminoidin separation and purification, and this technique also can be applicable to extraction and the production of other pigments.The present invention, relative to Two-phase system separation and purification Gardenia Yellow waste liquid of the prior art, achieves following effect:
1. the present invention have developed a kind of Virahol-salt Two-phase system separation and purification Gardenia Yellow waste liquid, is specially Virahol-sodium carbonate double-aqueous phase system, not relevant report in prior art;
2., under condition of the present invention, crystal, the yield that can reach 98.5% with purity are up to 98.2% acquisition target product jasminoidin, create unforeseeable technique effect compared to prior art.
Embodiment
Below by specific embodiment, method of the present invention is described, but the present invention is not limited thereto.
Experimental technique described in following embodiment, if no special instructions, is ordinary method; Described reagent and material, if no special instructions, all can obtain from commercial channels.
embodiment 1
Double-aqueous phase system 20mL is prepared by sodium carbonate and Virahol mass percent 10% under room temperature, concentrated Gardenia Yellow waste liquid 5mL is joined this double-aqueous phase system, temperature constant magnetic stirring (10 DEG C, 300r/min) 40min, regulates pH=9 simultaneously, make jasminoidin enrichment, leave standstill 80min, through the centrifugal 30min of 1500rpm, isolate jasminoidin enrichment phase, at-0.06MPa, under 20 DEG C of conditions, obtain jasminoidin crystal crude product through vacuum rotating concentrate drying.Carry out recrystallization by the ethyl acetate of 8 times of volumes and obtain jasminoidin crystal.The purity measuring jasminoidin is 98.5%, and product yield reaches 98.2%.
embodiment 2
Double-aqueous phase system 20mL is prepared by sodium carbonate and Virahol mass percent 30% under room temperature, concentrated Gardenia Yellow waste liquid 5mL is joined this double-aqueous phase system, temperature constant magnetic stirring (35 DEG C, 300r/min) 30min, regulates pH=9 simultaneously, make jasminoidin enrichment, leave standstill 60min, through the centrifugal 20min of 1000rpm, isolate jasminoidin enrichment phase, at-0.04MPa, under 50 DEG C of conditions, obtain jasminoidin crystal crude product through vacuum rotating concentrate drying.Carry out recrystallization with the sherwood oil of 4 times of volumes and obtain jasminoidin crystal.The purity measuring jasminoidin is 96.7%, and product yield reaches 96.6%.
embodiment 3
Double-aqueous phase system 20mL is prepared by sodium carbonate and Virahol mass percent 30% under room temperature, concentrated Gardenia Yellow waste liquid 5mL is joined this double-aqueous phase system, temperature constant magnetic stirring (50 DEG C, 300r/min) 60min, regulates pH=12 simultaneously, make jasminoidin enrichment, leave standstill 100min, through the centrifugal 40min of 2000rpm, isolate jasminoidin enrichment phase, at-0.09MPa, under 90 DEG C of conditions, obtain jasminoidin crystal crude product through vacuum rotating concentrate drying.Carry out recrystallization with the acetone of 10 times of volumes and obtain jasminoidin crystal.The purity measuring jasminoidin is 96.9%, and product yield reaches 95.4%.
embodiment 4
Double-aqueous phase system 20mL is prepared by dipotassium hydrogen phosphate and Virahol mass percent 10% under room temperature, concentrated Gardenia Yellow waste liquid 5mL is joined this double-aqueous phase system, temperature constant magnetic stirring (50 DEG C, 300r/min) 60min, regulates pH=9 simultaneously, make jasminoidin enrichment, leave standstill 100min, through the centrifugal 40min of 2000rpm, isolate jasminoidin enrichment phase, at-0.09MPa, under 90 DEG C of conditions, obtain jasminoidin crystal crude product through vacuum rotating concentrate drying.Carry out recrystallization with the acetone of 10 times of volumes and obtain jasminoidin crystal.The purity measuring jasminoidin is 93.6%, and product yield reaches 95.5%.

Claims (9)

1. the method for Virahol-salt double-aqueous phase system separation and purification jasminoidin, it is characterized in that utilizing cape jasmine fruit raw material production Gardenia Yellow waste liquid, it is obtained jasminoidin first product through Virahol-salt double-aqueous phase system extracting and separating, concentrate drying, then obtain high-purity gardenoside crystallization after organic solvent recrystallization.
2. the method for separation and purification jasminoidin according to claim 1, it is characterized in that comprising following concrete steps: under room temperature, prepare Virahol-salt double-aqueous phase system, Gardenia Yellow waste liquid is joined this double-aqueous phase system, at 10 ~ 50 DEG C, temperature constant magnetic stirring 30 ~ 60min under 300r/min condition, regulate pH=9 ~ 12 simultaneously, make jasminoidin enrichment, leave standstill 60 ~ 100min, through the centrifugal 20 ~ 40min of 1000 ~ 2000rpm, isolate jasminoidin enrichment phase, at-0.04 ~-0.09MPa, jasminoidin crystal crude product is obtained through vacuum rotating concentrate drying under 20 ~ 90 DEG C of conditions, recrystallization is carried out with organic solvent, obtain highly purified jasminoidin crystal.
3. the method for separation and purification jasminoidin according to claim 1 and 2, is characterized in that: described organic solvent is the mixture of one or more of ethyl acetate, acetone or sherwood oil.
4. the method for separation and purification jasminoidin according to claims 1 or 2, is characterized in that: described Virahol-salt double-aqueous phase system salt is sylvite, sodium salt or ammonium salt.
5. the method for separation and purification jasminoidin according to claims 4, is characterized in that: in described salt, sylvite is K 2hPO 4, K 2cO 3, KCl; Sodium salt is Na 2cO 3, NaCl, Na 2sO 4; Ammonium salt is NH 4cl, (NH 4) 2sO 4, NH 4hCO 3.
6. the method for separation and purification jasminoidin according to claim 5, is characterized in that: described salt more preferably sodium carbonate.
7. the method for separation and purification jasminoidin according to claims 6, it is characterized in that: described Virahol-salt double-aqueous phase system is Virahol-sodium carbonate system, wherein the mass percent of sodium carbonate and Virahol is 5% ~ 30%, system pH is 9 ~ 12.
8. the method for separation and purification jasminoidin according to claims 3, it is characterized in that: described recrystallization solvent solvent is ethyl acetate, add-on is 4 ~ 10 times of jasminoidin crude product quality.
9. the method for separation and purification jasminoidin according to above-mentioned any one claim, is characterized in that: jasminoidin crystal purity is up to more than 98.5%, and product yield reaches 98.2%.
CN201410721860.4A 2014-12-03 2014-12-03 A kind of method of isopropanol-isolated and purified jasminoidin of salt double-aqueous phase system Expired - Fee Related CN104356184B (en)

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CN105037461A (en) * 2015-07-08 2015-11-11 邵阳学院 Multistage aqueous two-phase synchronous separation for geniposide and gardenia yellow
CN107325859A (en) * 2017-08-16 2017-11-07 杨杰东 Antifriction antiwear type lubricating oil additive and preparation method thereof
CN107722078A (en) * 2017-10-18 2018-02-23 青岛大学 The method of normal propyl alcohol sodium potassium tartrate tetrahydrate double-aqueous phase system extraction separation and purification phloridzin
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Publication number Priority date Publication date Assignee Title
CN105037461A (en) * 2015-07-08 2015-11-11 邵阳学院 Multistage aqueous two-phase synchronous separation for geniposide and gardenia yellow
CN105037461B (en) * 2015-07-08 2018-06-05 邵阳学院 Multistage aqueous two-phase separated in synchronization Gardenoside and Gardenia Yellow
CN107325859A (en) * 2017-08-16 2017-11-07 杨杰东 Antifriction antiwear type lubricating oil additive and preparation method thereof
CN107722078A (en) * 2017-10-18 2018-02-23 青岛大学 The method of normal propyl alcohol sodium potassium tartrate tetrahydrate double-aqueous phase system extraction separation and purification phloridzin
CN107722078B (en) * 2017-10-18 2020-07-10 青岛大学 Method for extracting, separating and purifying phlorizin by n-propanol-potassium sodium tartrate aqueous two-phase system
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CN112480194A (en) * 2020-11-26 2021-03-12 浙江工业大学 Method for simultaneously preparing high-purity geniposide and gardenia yellow by one-step two-aqueous-phase extraction
CN112480194B (en) * 2020-11-26 2022-05-31 浙江工业大学 Method for simultaneously preparing high-purity geniposide and gardenia yellow by one-step two-aqueous-phase extraction
CN114702836A (en) * 2022-04-23 2022-07-05 南京林业大学 Method for extracting and purifying pigment from jujube residues
CN116495753A (en) * 2023-04-26 2023-07-28 中国科学院生态环境研究中心 Method for recycling industrial waste salt through recrystallization and purification

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