CN103468767A - Method for preparing orcinol glucoside - Google Patents

Method for preparing orcinol glucoside Download PDF

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Publication number
CN103468767A
CN103468767A CN 201310423503 CN201310423503A CN103468767A CN 103468767 A CN103468767 A CN 103468767A CN 201310423503 CN201310423503 CN 201310423503 CN 201310423503 A CN201310423503 A CN 201310423503A CN 103468767 A CN103468767 A CN 103468767A
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Prior art keywords
concentrated
ethanolic soln
column volume
orcinol
solution
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杨存
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Nanjing Tongze Agricultural Science and Technology Co Ltd
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Nanjing Tongze Agricultural Science and Technology Co Ltd
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Abstract

The invention discloses a method for preparing orcinol glucoside. The method comprises the following steps of: 1) crushing raw material which is rhizoma curculiginis, adding bio-enzyme for enzymolysis, adding 5-10 times 30-90% ethanol solution into the raw mateiral subjected to enzymolysis, backflowing and extracting for 2-3 times, filtering and concentrating the extract, diluting the concentrated liquid by using an appropriate amount of water, absorbing by using a large-pore resin, carrying out gradient elution by using an ethanol solution, and concentrating the eluant so as to obtain a concentrated solution; and 2) diluting the concentrated solution by using an appropriate amount of water, absorbing by using the large-pore resin, eluting impurities by using 4-7 times by column volume of a 20-40% ethanol solution, further eluting by using 5-8 times by column volume of 50-70% ethanol solution, concentrating the eluant, extracting by using a n-butyl alcohol solution, concentrating the extract to be a small volume, standing and crystallizing; recrystalizing the crystal substance by using ethyl acetate, and drying at a low temperature so as to obtain the orcinol glucoside. When the preparation method is used for producing orcinol glucoside, the process is simple to operate, the production cost is low, and the industrial production is easy to carry out.

Description

A kind of preparation method of orcinol glucoside
Technical field
The invention belongs to the Natural Medicine Chemistry field, be specifically related to a kind of preparation method of orcinol glucoside.
Background technology
The orcinol glucoside, CAS 21082-33-7, molecular weight is C13H18O7, molecular weight is 286.28 molecular structural formulas:
Figure 2013104235035100002DEST_PATH_IMAGE002
The orcinol glucoside is white powder, the mixed solvent of water soluble and methyl alcohol, DMSO, hot methanol solvent.Be insoluble to sherwood oil, chloroform.The orcinol glucoside is present in the amrallid thizoma curculiginis, chemical composition to thizoma curculiginis has been carried out systematic research, and the compound of isolation identification mainly contains Cyclolanstane triterpenic glycosides, contains chlorophenol, phenolic glycoside, lignanoid's glycosides, flavones, alkaloid, long-chain fat same clan compound etc.By literature search, not yet there is the industrialized process for preparing of orcinol glucoside to disclose.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of preparation method who is easy to the orcinol glucoside of suitability for industrialized production.
The present invention is achieved by the following technical solutions: a kind of preparation method of orcinol glucoside is characterized in that comprising the following steps:
1) get the thizoma curculiginis raw material, pulverize, add the biological enzyme enzymolysis, the enzymolysis raw material adds 5-10 doubly to measure 30-90% ethanolic soln refluxing extraction 2-3 time, and extracting liquid filtering is concentrated, and concentrated solution above adsorbs in macroporous resin after adding the suitable quantity of water dilution, the ethanolic soln gradient elution, elutriant concentrates to obtain concentrated solution;
2) above-mentioned concentrated solution adds the suitable quantity of water solution dilution, add in macroporous resin and adsorb, with 4-7 times of column volume 20-40% ethanolic soln wash-out impurity, again with 5-8 times of column volume 50-70% ethanol elution, elutriant is concentrated to be extracted with butanol solution, extraction liquid is concentrated into small volume and places crystallization, and crystallisate is used re-crystallizing in ethyl acetate again, cryodrying and get final product.
A kind of in the optional amylase of biological enzyme in described step 1), polygalacturonase or cellulase.
Described step 1) and 2) a kind of in the optional ADS-21 of macroporous resin model, AB-8, NK-9 and HPD400 in.
Described step 1) ethanolic soln gradient elution is 5-10 times of column volume 10-30% ethanolic soln wash-out impurity, then by 5-10 times of column volume 50-70% ethanol elution effective constituent.
Adopt technique scheme to produce the orcinol glucoside, method is simple to operate, and production cost is low, is easy to realize industrialization.
Embodiment
below in conjunction with specific embodiment, the invention will be further described.
Embodiment 1:
Getting thizoma curculiginis raw material 10kg pulverizes, add 2L water and 15g cellulase degradation 3 hours, the enzymolysis raw material adds 7 times of amount 60% ethanolic soln refluxing extraction 3 times, concentrated solution adds after suitable quantity of water is diluted to add in the ADS-21 macroporous resin and adsorbs, first use 5 times of column volumes, 30% ethanolic soln wash-out impurity, use again 8 times of column volumes, 60% ethanol elution effective constituent, the dilution of concentrated solution suitable quantity of water, add in the AB-8 macroporous resin and adsorb, with 6 times of column volumes, 30% ethanolic soln wash-out impurity, use again 8 times of column volume 55% ethanol elutions, collect the elutriant concentrating under reduced pressure, concentrated with butanol solution extraction 3 times, extraction liquid is concentrated into 50ml and places crystallization, crystallisate leaches uses the acetic acid ethyl dissolution recrystallization, cryodrying obtains orcinol glucoside 16g, through hplc, detect, content 98.2%.
Embodiment 2:
Getting thizoma curculiginis raw material 10kg pulverizes, add 3L water and 20g pectinase enzymatic hydrolysis 5 hours, the enzymolysis raw material adds 8 times of amount 90% ethanolic soln refluxing extraction 3 times, concentrated solution adds after suitable quantity of water is diluted to add in the AB-8 macroporous resin and adsorbs, first use 5 times of column volumes, 30% ethanolic soln wash-out impurity, use again 8 times of column volumes, 60% ethanol elution effective constituent, the dilution of concentrated solution suitable quantity of water, add in the NK-9 macroporous resin and adsorb, with 6 times of column volumes, 40% ethanolic soln wash-out impurity, use again 6 times of column volume 60% ethanol elutions, collect the elutriant concentrating under reduced pressure, concentrated with butanol solution extraction 3 times, extraction liquid is concentrated into 70ml and places crystallization, crystallisate leaches uses the acetic acid ethyl dissolution recrystallization, cryodrying obtains orcinol glucoside 17g, through hplc, detect, content 98.3%.
Embodiment 3:
Getting thizoma curculiginis raw material 10kg pulverizes, add 2L water and 20g amylase enzymolysis 4 hours, the enzymolysis raw material adds 6 times of amount 30% ethanolic soln refluxing extraction 3 times, concentrated solution adds after suitable quantity of water is diluted to add in the NK-9 macroporous resin and adsorbs, first use 5 times of column volumes, 30% ethanolic soln wash-out impurity, use again 6 times of column volumes, 60% ethanol elution effective constituent, the dilution of concentrated solution suitable quantity of water, add in the HPD400 macroporous resin and adsorb, with 5 times of column volumes, 30% ethanolic soln wash-out impurity, use again 5 times of column volume 70% ethanol elutions, collect the elutriant concentrating under reduced pressure, concentrated with butanol solution extraction 3 times, extraction liquid is concentrated into 60ml and places crystallization, crystallisate leaches uses the acetic acid ethyl dissolution recrystallization, cryodrying obtains orcinol glucoside 19g, through hplc, detect, content 97.5%.
Embodiment 4:
Getting thizoma curculiginis raw material 10kg pulverizes, add 2L water and 20g cellulase degradation 3 hours, the enzymolysis raw material adds 7 times of amount 70% ethanolic soln refluxing extraction 3 times, concentrated solution adds after suitable quantity of water is diluted to add in the HPD400 macroporous resin and adsorbs, first use 5 times of column volumes, 40% ethanolic soln wash-out impurity, use again 8 times of column volumes, 50% ethanol elution effective constituent, the dilution of concentrated solution suitable quantity of water, add in the AB-8 macroporous resin and adsorb, with 5 times of column volumes, 20% ethanolic soln wash-out impurity, use again 8 times of column volume 50% ethanol elutions, collect the elutriant concentrating under reduced pressure, concentrated with butanol solution extraction 3 times, extraction liquid is concentrated into 60ml and places crystallization, crystallisate leaches uses the acetic acid ethyl dissolution recrystallization, cryodrying obtains orcinol glucoside 15g, through hplc, detect, content 98.5%.

Claims (4)

1. the preparation method of an orcinol glucoside is characterized in that comprising the following steps:
1) get the thizoma curculiginis raw material, pulverize, add the biological enzyme enzymolysis, the enzymolysis raw material adds 5-10 doubly to measure 30-90% ethanolic soln refluxing extraction 2-3 time, and extracting liquid filtering is concentrated, and concentrated solution above adsorbs in macroporous resin after adding the suitable quantity of water dilution, the ethanolic soln gradient elution, elutriant concentrates to obtain concentrated solution;
2) above-mentioned concentrated solution adds the suitable quantity of water solution dilution, add in macroporous resin and adsorb, with 4-7 times of column volume 20-40% ethanolic soln wash-out impurity, again with 5-8 times of column volume 50-70% ethanol elution, elutriant is concentrated to be extracted with butanol solution, extraction liquid is concentrated into small volume and places crystallization, and crystallisate is used re-crystallizing in ethyl acetate again, cryodrying and get final product.
2. the preparation method of orcinol glucoside according to claim 1, is characterized in that a kind of in the optional amylase of biological enzyme, polygalacturonase or the cellulase in described step 1).
3. the preparation method of orcinol glucoside according to claim 1, is characterized in that described step 1) and 2) in the optional ADS-21 of macroporous resin model, AB-8, NK-9 and HPD400 in a kind of.
4. the preparation method of orcinol glucoside according to claim 1, it is characterized in that described step 1) ethanolic soln gradient elution is 5-10 times of column volume 10-30% ethanolic soln wash-out impurity, then by 5-10 times of column volume 50-70% ethanol elution effective constituent.
CN 201310423503 2013-09-17 2013-09-17 Method for preparing orcinol glucoside Pending CN103468767A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113667655A (en) * 2021-08-24 2021-11-19 云南农业大学 Curculigo orchioides glycosyltransferase Co84A-471 gene and application thereof in preparation of orcinol glucoside

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113667655A (en) * 2021-08-24 2021-11-19 云南农业大学 Curculigo orchioides glycosyltransferase Co84A-471 gene and application thereof in preparation of orcinol glucoside
CN113667655B (en) * 2021-08-24 2023-03-14 云南农业大学 Curculigo orchioides glycosyltransferase Co84A-471 gene and application thereof in preparation of orcinol glucoside

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