CN109293509A - A method of preparing high-purity chlorogenic acid from bamboo extractive - Google Patents
A method of preparing high-purity chlorogenic acid from bamboo extractive Download PDFInfo
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- CN109293509A CN109293509A CN201811457262.5A CN201811457262A CN109293509A CN 109293509 A CN109293509 A CN 109293509A CN 201811457262 A CN201811457262 A CN 201811457262A CN 109293509 A CN109293509 A CN 109293509A
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- chlorogenic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Abstract
A method of it preparing high-purity chlorogenic acid from bamboo extractive, belongs to technical field of natural product extraction.It is comprised the following steps that: 1) macroreticular resin separates: using bamboo extractive as raw material, it is splined on macroporous absorbent resin, distilled water, 60% ethyl alcohol, 95% ethanol elution are successively used, part unadsorbed after loading and water elution part are collected respectively, obtain concentrate A and concentrate B after concentration respectively;2) high speed adverse current chromatogram separates: taking acetate-methanol or acetonitrile-acetic acid-water two phase solvent system to carry out separation and purification treatment to concentrate A and concentrate B in HSCCC chromatograph, obtains chlorogenic acid monomer.The present invention can simply, efficiently obtain Chlorogenic acid compound from bamboo extractive; its efficiently separating with the bamboo-leaves flavones ingredient of bamboo extractive is realized simultaneously; small-scale or industrialized application suitable for the two production preparation process, helps to improve the added value of production.
Description
Technical field
The invention belongs to technical field of natural product extraction, and in particular to utilize macroporous resin column chromatography combination high-speed counter-current
Chromatography (HSCCC) technology, prepares the method for high-purity chlorogenic acid from bamboo extractive.
Background technique
Bamboo is grass family Bambusoideae perennial plant, has long edible and medicinal history in China.Studies have shown that
Containing there are many chemical component abundant in the leaf of bamboo, including flavonoids, phenolic acid class, polysaccharide, cumarin lactone, Anthraquinones, amino acid,
Aromatic substance and manganese, zinc, selenium and other trace elements.Wherein bamboo-leaves flavones are mainly with orientoside, Lutonaretin, Vitexina, different Vitex negundo var cannabifolia
Based on glycosides etc., have the function of restraining and sterilizing bacteria, anti-inflammatory, detumescence, reducing blood lipid and scavenging activated oxygen etc..And chlorogenic acid is the leaf of bamboo
One of the important activity ingredient of a kind of main phenolic acid components and traditional Chinese medicine honeysuckle, folium cortex eucommiae etc., has extensive biology
Activity, have antibacterial, it is antiviral, increase white blood cell, Hepatoprotective cholagogue, antitumor, lowering blood pressure and blood fat, remove free radical and emerging
The effects of central nervous system of putting forth energy;Modern science has been deep into food, health care, doctor to the research and application of chlorogenic acid bioactivity
The multiple fields such as medicine and daily-use chemical industry.Thus, the isolation and purification method of exploitation bamboo extractive Content of Chlorogenic Acid has very big reality
With value.
Macroporous absorbent resin is common Separation of Natural Products material, choose with absorption, is at low cost, is easy to operate etc.
Many-sided advantage.In the patent of invention of Chinese Patent Application No. 200910223926.6, a kind of HP-20 macroporous absorption is disclosed
The method that resin prepares bamboo-leaves flavones.
High speed adverse current chromatogram (HSCCC) is a kind of new chromatographic separating and purifying technology based on liquid-liquid distribution mechanism, due to
It does not have to any solid supporter or carrier, has many advantages, such as that sample recovery rate is high, operating procedure is few, particularly suitable for natural
The separation of active monomer component.Has the correlative study report using HSCCC separating chlorogenic acid before this.Chinese Patent Application No. is
201010542548.0, which disclose one kind, carries out HSCCC from eucommia leaf extract from application ethyl acetate-n-butanol-water system
The method for obtaining chlorogenic acid.The disclosure of the invention that Chinese Patent Application No. is 201510316229.0 is a kind of from applying n-hexane-
Acetate-methanol-aqueous systems carry out the method that HSCCC obtains chlorogenic acid from Chinese mahonia leaf extract.Chinese patent Shen
Number a kind of HSCCC please be carried out from fructus arctii from application acetate-methanol-aqueous systems for 201710120670.0 disclosure of the invention
The method of chlorogenic acid is obtained in extract.
Although the above method can obtain bamboo-leaves flavones or chlorogenic acid ingredient respectively, without for bamboo extractive
Own characteristic, macroreticular resin separating chlorogenic acid and bamboo-leaves flavones can be efficiently used and utilize HSCCC efficient by developing one kind
Remove the method that leaf of bamboo pigment and impurity obtain high-purity chlorogenic acid.
Summary of the invention
In view of the problems of the existing technology, it is an object of the invention to design to provide one kind and prepare from bamboo extractive
The technical solution of the method for high-purity chlorogenic acid.This method passes through preferred macroreticular resin first and isolates and purifies, and efficiently separates and obtains
Obtain chlorogenic acid;Then HSCCC separation is carried out using acetate-methanol (or acetonitrile)-acetic acid-aqueous solvent system, from chlorogenic acid
The chlorogenic acid of high-purity in enriched substance acquisition.This method can effectively obtain chlorogenic acid, while realize itself and bamboo extractive
Bamboo-leaves flavones ingredients efficiently separate.
A kind of method preparing high-purity chlorogenic acid from bamboo extractive, it is characterised in that including following technique
Step:
1) macroreticular resin separates: using bamboo extractive as raw material, being splined on macroporous absorbent resin, successively uses distilled water, 60% second
Alcohol, 95% ethanol elution, part unadsorbed after loading and water elution part are collected respectively, obtained respectively after concentration concentrate A and
Concentrate B;Through analyzing, concentrate A and concentrate B contain a large amount of chlorogenic acid ingredient (overall recovery >=90%), only containing few
The bamboo leave flavone ingredient (overall recovery≤10%) of amount.60% ethanol elution part (flow point C) is collected, is concentrated after concentration
Object C is analyzed containing a large amount of bamboo leave flavone (overall recovery >=80%) ingredient in the enriched substance, only containing a small amount of (total recycling
Rate≤5%) chlorogenic acid ingredient;
2) high speed adverse current chromatogram separates: taking acetate-methanol or acetonitrile-acetic acid-water two phase solvent system in HSCCC chromatograph
In separation and purification treatment is carried out to concentrate A and concentrate B, and collect outlet automatically according to the chromatographic runing time of HSCCC
Locate efflux, HPLC detection is carried out to efflux, the collection liquid by chlorogenic acid purity greater than 90% merges respectively, uses rotary evaporation
Instrument recycling design, obtains chlorogenic acid monomer;
The two phase solvent system is ethyl acetate: methanol: acetic acid: water volume percentage is 30~45:5~15:5~15:
30~50 or ethyl acetate: acetonitrile: acetic acid: water volume percentage is 30~45:5~15:5~15:30~50, and upper phase is solid
Determine phase, lower phase is mobile phase.
A kind of method preparing high-purity chlorogenic acid from bamboo extractive, it is characterised in that the step 1)
The concentration of middle bamboo extractive are as follows: the aqueous solution of 5~100 mg/mL in terms of extract dry weight.
A kind of method preparing high-purity chlorogenic acid from bamboo extractive, it is characterised in that the step 1)
Middle macroreticular resin is D101 or XAD-7HP.
A kind of method preparing high-purity chlorogenic acid from bamboo extractive, it is characterised in that the step 1)
Middle loading flow velocity is 1~4BV/h, and the elution volume of loading extract quality≤1 g/g resin, water is 3~6BV, and 60% ethyl alcohol is washed
Lift-off product >=4BV, elution flow rate are 1~4BV/h.
A kind of method preparing high-purity chlorogenic acid from bamboo extractive, it is characterised in that the step 2)
High speed adverse current chromatogram separation specifically: take acetate-methanol or acetonitrile-acetic acid-water two phase solvent system in separatory funnel
In be configured to mixed solution, take upper layer be stationary phase, lower layer is mobile phase;With the speed of 10~20mL/min to HSCCC chromatography
It is pumped into stationary phase in instrument, host is rotated with 600~1000rpm after pipeline is completely filled with stationary phase, while with 1~3mL/min
Speed be pumped into mobile phase, until mobile phase flow out and UV detector monitor display baseline it is steady after, take and be dissolved in stream in right amount
The concentrate A or B of dynamic phase injects HSCCC chromatograph with sample injector, collects exit efflux, convection current automatically according to runing time
Liquid carries out HPLC detection out, and the collection liquid by chlorogenic acid purity greater than 90% merges respectively, with Rotary Evaporators recycling design, obtains
To chlorogenic acid monomer.
The present invention can simply, efficiently obtain Chlorogenic acid compound from bamboo extractive, while realize itself and bamboo
The bamboo-leaves flavones ingredient of leaf extract efficiently separates, small-scale or industrialized answering suitable for the two production preparation process
With helping to improve the added value of production.
Detailed description of the invention
Fig. 1 is the HPLC spectrogram of bamboo extractive, and peak 1-5 is respectively chlorogenic acid, Lutonaretin, orientoside, Vitex negundo var cannabifolia in figure
Glycosides, Saponaretin;
Fig. 2 is the HPLC figure that 1 macropore of embodiment separates flow point A, and peak 1 is respectively chlorogenic acid in figure;
Fig. 3 is the HPLC figure that 1 macropore of embodiment separates flow point B, and peak 1 is respectively chlorogenic acid in figure;
Fig. 4 is the HPLC figure that 1 macropore of embodiment separates flow point C, in figure peak 1-4 be respectively Lutonaretin, orientoside, Vitexina,
Saponaretin;
Fig. 5 is the HSCCC separation chromatogram of macroreticular resin flow point A in embodiment 1, and peak 1 is respectively the chlorogenic acid peak collected in figure;
Fig. 6 is the HPLC chromatogram of chlorogenic acid standard items;
Fig. 7 is that macroreticular resin flow point A HSCCC separates the HPLC chromatogram that chlorogenic acid is made in embodiment 1.
Specific embodiment
Further illustrate the present invention with reference to embodiments.
Bamboo extractive in the present invention is substance of the leaf of bamboo after water extracts concentration, if Fig. 1 is the bamboo extractive
HPLC spectrogram, peak 1-5 is respectively chlorogenic acid, Lutonaretin, orientoside, Vitexina, Saponaretin in figure.
Embodiment 1
(1) macroreticular resin separates
16.8 grams of bamboo extractive, 20 mg/mL bamboo extractive, 840 mL being diluted with water to after taking freeze-drying, with
2BV/h flow velocity is splined on 50g D101 macroporous absorbent resin (mL of 1BV=40), then successively uses 5BV distilled water, 4BV 60%
Ethyl alcohol, 95% ethanol elution of 4BV, elution flow rate 2BV/h.By efflux (flow point A) after loading and water elution part (flow point B)
It collects respectively, obtains concentrate A and B after concentration respectively;60% ethanol elution part (flow point C) is collected, concentration obtains bamboo-leaves flavones
Enriched substance C.Fig. 2 is the HPLC figure that macropore separates flow point A, and peak 1 is chlorogenic acid in figure;Fig. 3 is the HPLC that macropore separates flow point B
Scheme, peak 1 is respectively chlorogenic acid in figure;Fig. 4 is the HPLC figure that 1 macropore of embodiment separates flow point C, and peak 1-4 is respectively different Polygonum in figure
Careless glycosides, orientoside, Vitexina, Saponaretin.
Experiment is using liquid chromatogram (HPLC) condition for analyzing extract solution of bamboo leaves Content of Chlorogenic Acid and 4 kinds of flavones are as follows: with Shimadzu
C18 chromatographic column (4.6mm × 250mm, 5 μm) is filler, using acetonitrile A as mobile phase, to be stream containing 0.1% formic acid solution
Dynamic phase B, gradient elution time-program(me) are as follows: 0~10 minute mobile phase A is 15%, and 10~30 minutes mobile phase As are 15 → 30%.Inspection
Survey wavelength be 325nm, flow velocity 1.0mL/min, 30 DEG C of column temperature, 20 μ l of sample volume.
(2) high speed adverse current chromatogram isolates and purifies
With ethyl acetate: acetonitrile: acetic acid: water (volume ratio 35:10:5:50) is that HSCCC solvent system is abundant in separatory funnel
Half an hour is placed after shaking, is layered it sufficiently.Then two-phase is separated, in upper phase as stationary phase, lower phase as mobile phase,
30 min of ultrasonic degassing.510 mg of concentrate A is taken, is dissolved in 10 mL mobile phases, sample to be separated is used as after filtering.To
Stationary phase is pumped into the speed of 20 mL/min in HSCCC chromatograph, is rotated after pipeline is sufficiently full of stationary phase with 850rpm
Host, while 2 mL/min are pumped into mobile phase, Detection wavelength is set as 325 nm, reaches balance to two-phase, after baseline stability with into
Sample device injects sample;Effluent is collected automatically from exit, is tested and analyzed and is merged in 140-160min flow point through HPLC, concentration is dry
Dry acquisition purity is 90.5% chlorogenic acid, 28 mg.Concentrate B 634mg separately is taken, is dissolved in 10 mL mobile phases, use is identical
HSCCC condition collects 140-160min flow point, and being concentrated and dried and obtaining purity is 92.1% chlorogenic acid, 24 mg.
Experiment is using liquid chromatogram (HPLC) condition for analyzing extract solution of bamboo leaves Content of Chlorogenic Acid purity are as follows: with Shimadzu C18 color
Composing column (4.6mm × 250mm, 5 μm) is filler, with -0.1% formic acid solution of acetonitrile (15:85) for mobile phase.Detection wavelength is
325nm, flow velocity 1.0mL/min, 30 DEG C of column temperature, 20 μ l of sample volume.Fig. 5 is HSCCC points of macroreticular resin flow point A in embodiment 1
From chromatogram, peak 1 is respectively the chlorogenic acid peak collected in figure.Fig. 6 is the HPLC chromatogram of chlorogenic acid standard items.Fig. 7 is real
It applies macroreticular resin flow point A HSCCC in example 1 and separates the HPLC chromatogram that chlorogenic acid is made.
Embodiment 2
(1) macroreticular resin separates
16.1 grams of bamboo extractive, 20 mg/mL leaf of bamboo extract, 805 mL after being diluted with water to after taking freeze-drying, with
2BV/h flow velocity is splined on 50g XAD-7HP macroporous absorbent resin (mL of 1BV=35), then successively uses 5BV distilled water, 6BV
60% ethyl alcohol, 95% ethanol elution of 4BV mL, elution flow rate 2BV/h.By efflux (flow point A) after loading and water elution part
(flow point B) is collected respectively, obtains concentrate A and B after concentration respectively;60% ethanol elution part (flow point C) is collected, concentration obtains
Bamboo-leaves flavones enriched substance C.Experiment is same using liquid chromatogram (HPLC) condition of analysis extract solution of bamboo leaves Content of Chlorogenic Acid and 4 kinds of flavones
On.
(2) high speed adverse current chromatogram isolates and purifies
With ethyl acetate: methanol: acetic acid: water (volume ratio 40:10:5:45) is that HSCCC solvent system is abundant in separatory funnel
Half an hour is placed after shaking, is layered it sufficiently.Then two-phase is separated, in upper phase as stationary phase, lower phase as mobile phase,
30 min of ultrasonic degassing.523 mg of concentrate A is taken, is dissolved in 10 mL mobile phases, sample to be separated is used as after filtering.To
Stationary phase is pumped into the speed of 20 mL/min in HSCCC chromatograph, is rotated after pipeline is sufficiently full of stationary phase with 850rpm
Host, while 2 mL/min are pumped into mobile phase, Detection wavelength is set as 325 nm, reaches balance to two-phase, after baseline stability with into
Sample device injects sample;Effluent is collected automatically from exit, is tested and analyzed and is merged in 165-185 min flow point, concentration through HPLC
The dry purity that obtains is 93.5% chlorogenic acid, 7 mg.Concentrate B 634mg separately is taken, is dissolved in 10 mL mobile phases, use is identical
HSCCC condition collects 165-185 min flow point, and being concentrated and dried and obtaining purity is 95.1% chlorogenic acid, 20 mg.Experiment is using analysis
Liquid chromatogram (HPLC) condition of extract solution of bamboo leaves Content of Chlorogenic Acid purity is same as above.
Claims (5)
1. a kind of method for preparing high-purity chlorogenic acid from bamboo extractive, it is characterised in that comprise the following steps that:
1) macroreticular resin separates: using bamboo extractive as raw material, being splined on macroporous absorbent resin, successively uses distilled water, 60% second
Alcohol, 95% ethanol elution, part unadsorbed after loading and water elution part are collected respectively, obtained respectively after concentration concentrate A and
Concentrate B;
2) high speed adverse current chromatogram separates: taking acetate-methanol or acetonitrile-acetic acid-water two phase solvent system in HSCCC chromatograph
In separation and purification treatment is carried out to concentrate A and concentrate B, and collect outlet automatically according to the chromatographic runing time of HSCCC
Locate efflux, HPLC detection is carried out to efflux, the collection liquid by chlorogenic acid purity greater than 90% merges respectively, uses rotary evaporation
Instrument recycling design, obtains chlorogenic acid monomer;
The two phase solvent system is ethyl acetate: methanol: acetic acid: water volume percentage is 30~45:5~15:5~15:
30~50 or ethyl acetate: acetonitrile: acetic acid: water volume percentage is 30~45:5~15:5~15:30~50, and upper phase is solid
Determine phase, lower phase is mobile phase.
2. a kind of method for preparing high-purity chlorogenic acid from bamboo extractive as described in claim 1, it is characterised in that institute
The concentration of bamboo extractive in the step 1) stated are as follows: the aqueous solution of 5~100 mg/mL in terms of extract dry weight.
3. a kind of method for preparing high-purity chlorogenic acid from bamboo extractive as described in claim 1, it is characterised in that institute
Macroreticular resin is D101 or XAD-7HP in the step 1) stated.
4. a kind of method for preparing high-purity chlorogenic acid from bamboo extractive as described in claim 1, it is characterised in that institute
Loading flow velocity is 1~4BV/h in the step 1) stated, loading extract quality≤1 g/g resin, the elution volume of water is 3~
6BV, 60% ethanol elution volume >=4BV, elution flow rate are 1~4BV/h.
5. a kind of method for preparing high-purity chlorogenic acid from bamboo extractive as described in claim 1, it is characterised in that institute
Step 2) the high speed adverse current chromatogram separation stated specifically: take acetate-methanol or acetonitrile-acetic acid-water two phase solvent system
Mixed solution is configured in separatory funnel, taking upper layer is stationary phase, and lower layer is mobile phase;With the speed of 10~20mL/min
It is pumped into stationary phase into HSCCC chromatograph, with 600~1000rpm rotation host after pipeline is completely filled with stationary phase, while with
The speed of 1~3mL/min is pumped into mobile phase, until mobile phase flows out and after UV detector monitors and shows that baseline is steady, takes
The concentrate A or B for being dissolved in mobile phase in right amount injects HSCCC chromatograph with sample injector, collects exit automatically according to runing time
Efflux carries out HPLC detection to efflux, and the collection liquid by chlorogenic acid purity greater than 90% merges respectively, uses Rotary Evaporators
Recycling design obtains chlorogenic acid monomer.
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Cited By (3)
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CN109809996A (en) * | 2019-02-19 | 2019-05-28 | 西昌学院 | A method of preparing high-purity chlorogenic acid from jacket |
CN110015959A (en) * | 2019-03-26 | 2019-07-16 | 北京林业大学 | A method of efficiently separating purifying caffeoyl quinic acid isomers from mulberry leaf |
CN115433085A (en) * | 2022-10-17 | 2022-12-06 | 南京久安源环保科技有限公司 | Production process for extracting bamboo leaf flavone and/or chlorogenic acid from bamboo leaves |
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CN110015959A (en) * | 2019-03-26 | 2019-07-16 | 北京林业大学 | A method of efficiently separating purifying caffeoyl quinic acid isomers from mulberry leaf |
CN110015959B (en) * | 2019-03-26 | 2021-09-24 | 北京林业大学 | Method for efficiently separating and purifying caffeoylquinic acid isomers from mulberry leaves |
CN115433085A (en) * | 2022-10-17 | 2022-12-06 | 南京久安源环保科技有限公司 | Production process for extracting bamboo leaf flavone and/or chlorogenic acid from bamboo leaves |
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