CN108440477B - A method of preparing Quercetin from tungoiltree juvenile leaf - Google Patents
A method of preparing Quercetin from tungoiltree juvenile leaf Download PDFInfo
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- CN108440477B CN108440477B CN201810364204.1A CN201810364204A CN108440477B CN 108440477 B CN108440477 B CN 108440477B CN 201810364204 A CN201810364204 A CN 201810364204A CN 108440477 B CN108440477 B CN 108440477B
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
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Abstract
The method that the invention discloses a kind of to prepare Quercetin from tungoiltree juvenile leaf, comprising the following steps: take tungoiltree juvenile leaf, crushed, put into ultrasonic wave preparing device, certain density alcoholic solution is added, be concentrated after intensified by ultrasonic wave extraction；Aqueous acid hydrolysis is added into concentrate；The pH value of hydrolyzate is adjusted to neutrality with lye；Then it is extracted with ethyl acetate, is concentrated, it is dry, MCI column chromatography and polyamide column chromatography separation are pressed in obtained extract warp, then uses Sephadex LH-20 gel and silica gel chromatography, obtains Quercetin product of the content 95% or more.The present invention has many advantages, such as that apparatus and process is simple, energy consumption is small, extraction efficiency is high, selected chromatographic material MCI, polyamide and gel can Reusability, be suitable for industrialized production.
Description
Technical field
The invention belongs to active components of plants extracting methods, are specifically related to a kind of side that Quercetin is prepared from tungoiltree juvenile leaf
Method.
Background technique
Tung oil tree is Euphorbiaceae tung tree defoliation small arbor, abundant in china natural resources.A kind of not still important stemness oil plant
Plant, and be a kind of practical medicinal plant, root, leaf, fruit are pharmaceutically acceptable, and civil usage history is long.Especially tung oil tree
Leaf, " Fujian traditional herbal medicine ", " vegetation is just square " record tungoiltree juvenile leaf have the effect of subdhing swelling and detoxicating, can treat carbuncle swells, erysipelas, scabies
Tinea, enteritis.
Quercetin also known as Quercetin are dissolved in glacial acetic acid, and alkaline aqueous solution is in yellow, are practically insoluble in water, ethanol solution
Taste is very bitter.It can be used as drug, there is preferable eliminating the phlegm, antitussive action, and have certain antiasthmatic effect.In addition there are reduce blood
Pressure, reduces capillary fragility, reducing blood lipid, coronary artery dilator at enhancing capillary resistance, increases coronary blood flow etc. and makees
With.For treating chronic bronchitis.Also there is auxiliary therapeutic action to coronary heart disease and hypertensive patient.Quercetin can significantly inhibit
The effect of carcinogenic promoting agent, the growth for inhibiting in vitro malignant cell inhibit ehrlich ascites cell DNA, RNA and protein synthesis.Mongolian oak
There are also the release actions for inhibiting platelet aggregation and serotonin (5-HT) by Pi Su.Quercetin is living to ADP, fibrin ferment and blood platelet
The platelet aggregation for changing the factor (PAF) induction has obvious inhibiting effect, wherein the inhibiting effect to PAF is most strong, Quercetin
The rabbit platelet 3H-5-HT of thrombin induction can be obviously inhibited to discharge.Quercetin is not soluble in water, therefore imports hydrophilic radical, closes
At Quercetin fluoroacetic acid lysine salt, water solubility increase, convenient for absorb, it is athero- for hemorrhagic disease, dyshaemia, artery
Hardening etc. has higher curative effect.
It is existing the study found that in tung oil tree blade contain Quercetin -3-O- α-L- rhamnopyranosyloxyhy glucosides.Quercetin methods of glycosides
It is that plant kingdom is distributed most common, widest flavonoid drugs, is ground extensively because it is with significant antioxidation
Study carefully, furthermore, it may have bacteriostatic activity is a kind of spectrum antibacterial substance, to common pathogenic bacteria such as staphylococcus aureus, large intestine
Bacillus, shigella dysenteriae all have efficient antibacterial activity, can be used for preventing and treating various bacterial infection diseases, also can be preparation plant
Source natural antiseptic agent provides raw material.
Currently, the preparation method of Quercetin has: 1, separating preparation from natural plants, such as " recycled from bioflavonoid
The methods of isoquercitin " (CN1355797), but such methods will use a large amount of organic solvent, pollute the environment, and
Low yield, it is at high cost, it is difficult to realize industrialization production.2, isoquercitrin and Quercetin, such as " enzyme are prepared with enzymatic hydrolysis rutin
The method that method hydrolysis prepares isoquercitin and Quercetin " (CN03133636.1), " from plant biomass preparation, purifying and conversion
Flavonoids " (CN1685053A), such method are needed using expensive biological enzyme formulation, and process equipment is more complex, raw
Produce higher cost.3, the industrialized production of Quercetin generally uses the technique of strong acid hydrolysis rutin (referring to Liu Yaping, Quercetin
The research of preparation method, when treasure's traditional Chinese medical science traditional Chinese medicines, 2004,15 (10): 657-658；He Qin, Xu Xiongliang etc., orthogonal experiment is preferred
The preparation process of analysis of quercetin in bud of Sophora japonica, Chinese herbal medicine, 2003,34 (5): 409-412), but to the requirement for anticorrosion of production equipment compared with
Height, and the three wastes are easy to produce, it is unfavorable for environmental protection.
Summary of the invention
Goal of the invention: the present invention provides a kind of method that Quercetin is prepared from tungoiltree juvenile leaf, and this method can effectively improve
The recovery rate of Quercetin and the purity of Quercetin, have many advantages, such as that preparation process is simple, are suitble to industrialized production.
A kind of technical solution: method preparing Quercetin from tungoiltree juvenile leaf of the present invention, comprising the following steps: (1)
Tungoiltree juvenile leaf is taken, is crushed, is put into 30-80Hz ultrasonic wave preparing device, 20-70% alcoholic solution is added, in intensified by ultrasonic wave
It is concentrated after extraction；(2) 1-5% aqueous acid hydrolysis 1-5h is added into the concentrate of step (1)；(3) it is adjusted and is walked with 1-5%NaOH
Suddenly the pH value of the hydrolyzate of (2) is to neutrality；(4) ethyl acetate extraction is added into hydrolyzate obtained in step (3), is concentrated,
It is dry, obtain Quercetin extract A；(5) methanol is added into Quercetin extract A to be completely dissolved to it, polyamide mixes sample, will
Methanol evaporates into dry, dress column, presses separation in connection MCI column progress, is for the methanol aqueous solution of 40-100% with percent by volume
Eluent gradient elution, thin-layered chromatography detection collect and merge the eluent that flowing phase concentration is 65-69%, be concentrated under reduced pressure, obtain
Obtain crude product A；(6) methanol is added into crude product A to being completely dissolved, mixes sample with polyamide, methanol is evaporated into dry, be transferred to polyamide
Chromatographic column is separated, and is eluted with the chloroform-methanol that volume ratio is 3-1:1, thin-layered chromatography detection, is collected to merge and be contained
The eluent of Quercetin is concentrated under reduced pressure, and obtains crude product B；(7) crude product B is dissolved in methanol, the water system of equivalent methanol volume is added
It is eluted with Sephadex LH-20 gel chromatography column purification with methanol at suspension, thin-layered chromatography detection is collected merging and contained
There is the eluent of Quercetin, be concentrated under reduced pressure, obtains crude product C；(8) by gained crude product C through silica gel chromatography, it is with volume ratio
The chloroform of 9-7:1-3-acetone elution, collects and merges the eluent containing Quercetin, be concentrated under reduced pressure, dry, obtains Quercetin and produces
Product.
In step (1), the alcoholic solution is any one or more in methanol, ethyl alcohol and n-butanol；The alcohol
The weight ratio of solution and tungoiltree juvenile leaf is 3:1.The temperature of the extraction is 40 DEG C~50 DEG C；The time of the extraction be 20~
40min。
In step (2), the acid solution is HCl or H2SO4In any one.
In step (4), the volume ratio of the hydrolyzate and ethyl acetate is 1:1-2.
In step (5), the mass ratio of the Quercetin extract A and polyamide is 1:2-4.The MCI column specification is
70 × 460mm, packing material are MCI-gel CHP-20P, column chromatography condition are as follows: column pressure is 80Psi, and flow rate of mobile phase is
50mL/min, Detection wavelength 245nm；The mobile phase is the methanol aqueous solution that percent by volume is 40-100%.
In step (6), the mass ratio of the crude product A and polyamide is 1:2-4.The specification of the polyamide is 200-300
Mesh；Eluent used is the chloroform-methanol that volume ratio is 3-1:1.
In step (7), the weight ratio of the crude product B and methanol is 1:4-8.
The utility model has the advantages that (1) is compared with prior art, the present invention uses the cavitation effect of ultrasonic wave, reinforces extract solutes
Mass-transfer efficiency promotes solvent to penetrate into plant tissue, thus achieve the effect that it is efficient, quickly prepare active constituent.(2) originally
Invention preparation method is not necessarily to high temperature, and intensified by ultrasonic wave extraction is carried out under the conditions of 40 DEG C~50 DEG C of temperature, will not be to Chinese medicine
Middle facile hydrolysis, oxidizable or to thermally labile active constituent generation destruction；(3) safety of the present invention is good, atmospheric extraction, operation
Simple and easy, maintenance is convenient；(4) extraction efficiency of the present invention is high, and ultrasonic energy promotes plant cell wall to rupture, strengthening extraction
20~40min can be obtained best preparation rate, and extraction quantity is the 2 times or more of conventional method, and extraction time is only boiling, alcohol deposition method
One third or less；(5) preparation method applicability of the present invention is wide, and ultrasound can be used in most each constituents of Chinese medicine
Wave extraction；(6) ultrasonic extraction of the invention is little to property (such as polarity) relationship of solvent and target extract, therefore, can
Selective extractant type is more, target extract is in extensive range；(7) energy consumption of the present invention is small, since ultrasonic extraction is without adding
Heat or heating temperature are low, and extraction time is short, therefore substantially reduces energy consumption, and extraction process is at low cost, and overall economic efficiency is significant；
(8) the Quercetin purity is high that the present invention obtains；(9) the suitable industrialized production of the present invention, can carry out a large amount of medicinal raw material
Processing, and impurity produced during the preparation process is few, effective component is easily isolated and purifies.
Specific embodiment
Below with reference to embodiment, the invention will be further described, and embodiments of the present invention are not limited thereto.
One, raw material sources
(1) MCI column column specification is 70mm × 460mm, and packing material is the MCI-gel of Mitsubishi chemical company production
CHP-20P, column chromatography condition are as follows: column pressure is 80Psi, flow rate of mobile phase 50mL/min, Detection wavelength 254nm.
(2) Sephadex LH-20 gel chromatographic columns are the production of Sweden Amersham Pharmacia Biotech company.
Two, sample preparation
Embodiment 1: the fresh tungoiltree juvenile leaf of 8kg is crushed, is put into 40Hz ultrasonic wave preparing device, 24L50% volume is added
The ethanol water of percentage is concentrated after intensified by ultrasonic wave extraction 20min, coextraction 3 times, filtering, merging filtrate at 40 DEG C,
Paste is concentrated under reduced pressure, obtains extract 1.05kg, 5.0LH is added in extract2SO41h is hydrolyzed in solution water, uses 5.0L5%
NaOH adjusts the pH value of hydrolyzate to neutrality, is extracted 3 times, combining extraction liquid, is concentrated under reduced pressure with 5.0L ethyl acetate, obtains quercitrin
Plain extract A120g to 120g Quercetin extract A, is added the dissolution of 300mL methanol, mixes sample with 260g polyamide, methanol is waved
It is sent to dry, dress column, separation is pressed in connection MCI column progress, the methanol aqueous solution with 40-100% percent by volume is that mobile phase is terraced
Degree elution, is collected by every part of 500mL, thin-layered chromatography detection, collects the elution for merging that flowing phase concentration is 65-69% percentage
Liquid is concentrated under reduced pressure, and obtains crude product A9.8g.
Crude product A is dissolved in 20mL methanol, 20g polyamide is added and mixes sample, methanol is volatilized dry, polyamide column progress is transferred to
Separation is eluted with the chloroform-methanol that volume ratio is 2:1, and thin-layered chromatography detection collects and merges the elution containing Quercetin
Liquid is concentrated under reduced pressure, and obtains crude product B 0.32g.
Crude product B is dissolved in the methanol of 1.0mL, 1.0mL water is added, suspension is made, with SephadexLH-20 gel color
Column purification is composed, is eluted with methanol, crude product C 0.90mg is obtained.
It by gained crude product C through silica gel chromatography, is eluted with the chloroform-methanol that volume ratio is 9:1, thin-layered chromatography inspection
It surveys, collects and merge the eluent containing Quercetin, be concentrated under reduced pressure, it is dry, obtain Quercetin product 35mg.
Embodiment 2: the fresh tungoiltree juvenile leaf of 8kg is crushed, is put into 40Hz ultrasonic wave preparing device, 24L70% volume is added
The ethanol water of percentage is concentrated after intensified by ultrasonic wave extraction 20min, coextraction 3 times, filtering, merging filtrate at 40 DEG C,
Paste is concentrated under reduced pressure, obtains extract 1.53kg, extract is added in 5.0L HCL solution water and hydrolyzes 1h, with 5.0L 5%
NaOH adjusts the pH value of hydrolyzate to neutrality, is extracted 3 times, combining extraction liquid, is concentrated under reduced pressure with 5.0L ethyl acetate, obtains quercitrin
The dissolution of 300mL methanol is added into Quercetin extract A, mixes sample with 260g polyamide, methanol is volatilized by plain extract A150g
To dry, dress column, separation is pressed in connection MCI column progress, the methanol aqueous solution with 40-100% percent by volume is eluent gradient
Elution is collected by every part of 500mL, thin-layered chromatography detection, collects the elution for merging that flowing phase concentration is 65-69% percentage
Liquid is concentrated under reduced pressure, and obtains crude product A13.4g.
Crude product A is dissolved in 20mL methanol, 20g polyamide is added and mixes sample, methanol is volatilized dry, polyamide column progress is transferred to
Separation is eluted with the chloroform-methanol that volume ratio is 3:1, and thin-layered chromatography detection collects and merges the elution containing Quercetin
Liquid is concentrated under reduced pressure, and obtains crude product B 0.43g.
Crude product B is dissolved in the methanol of 1.5mL, 1.5mL water is added, suspension is made, with SephadexLH-20 gel color
Column purification is composed, is eluted with methanol, crude product C1.21mg is obtained.
It by gained crude product C through silica gel chromatography, is eluted with the chloroform-methanol that volume ratio is 9:1, thin-layered chromatography inspection
It surveys, collects and merge the eluent containing Quercetin, be concentrated under reduced pressure, it is dry, obtain Quercetin product 42mg.
Embodiment 3: the fresh tungoiltree juvenile leaf of 8kg is crushed, is put into 40Hz ultrasonic wave preparing device, 24L70% volume is added
The ethanol water of percentage is concentrated after intensified by ultrasonic wave extraction 40min, coextraction 3 times, filtering, merging filtrate at 40 DEG C,
Paste is concentrated under reduced pressure, obtains extract 1.93kg.Extract is added in 5.0LHCL solution water and hydrolyzes 1h, uses 5.0L5%NaOH
The pH value of hydrolyzate is adjusted to neutrality, is extracted 3 times, combining extraction liquid, is concentrated under reduced pressure with 5.0L ethyl acetate, obtain Quercetin extraction
Take object A179g, into Quercetin extract A be added 300mL methanol dissolution, mix sample with 360g polyamide, methanol is evaporated into it is dry,
Column is filled, separation is pressed in connection MCI column progress, the methanol aqueous solution with 40-100% percent by volume is eluent gradient elution,
It is collected by every part of 500mL, thin-layered chromatography detection, collects the eluent for merging that flowing phase concentration is 65-69% percentage, decompression
Concentration obtains crude product A16.5g.
Crude product A is dissolved in 20mL methanol, 20g polyamide is added and mixes sample, methanol is volatilized dry, polyamide column progress is transferred to
Separation is eluted with the chloroform-methanol that volume ratio is 3:1, and thin-layered chromatography detection collects and merges the elution containing Quercetin
Liquid is concentrated under reduced pressure, and obtains crude product B 0.61g.
Crude product B is dissolved in the methanol of 1.5mL, 1.5mL water is added, suspension is made, with SephadexLH-20 gel color
Column purification is composed, is eluted with methanol, crude product C1.49mg is obtained.
It by gained crude product C through silica gel chromatography, is eluted with the chloroform-methanol that volume ratio is 9:1, thin-layered chromatography inspection
It surveys, collects and merge the eluent containing Quercetin, be concentrated under reduced pressure, it is dry, obtain Quercetin product 49mg.
Three, result detects
The Quercetin prepared in above-described embodiment 1-3 is detected, testing result is shown in Table 1.
The purity detecting result of the Quercetin prepared by the present invention of table 1
| Sample | Quercetin content (%) in sample |
| Embodiment 1 | 97 |
| Embodiment 2 | 95.3 |
| Embodiment 3 | 96.2 |
The Preparation Method of Quercetin extracted from tungoiltree juvenile leaf by the present invention it can be seen from the above results is simple, and recovery rate is high, and ties
Method of purification is closed, extracting cycle is short, and can get the Quercetin product of high-purity.
Claims (10)
1. a kind of method for preparing Quercetin from tungoiltree juvenile leaf, which comprises the following steps:
(1) tungoiltree juvenile leaf is taken, is crushed, is put into 30-80Hz ultrasonic wave preparing device, 20-70% alcoholic solution is added, in ultrasound
It is concentrated after wave strengthening extraction；
(2) 1-5% aqueous acid hydrolysis 1-5h is added into the concentrate of step (1)；
(3) use the pH value of the hydrolyzate of 1-5%NaOH regulating step (2) to neutrality；
(4) ethyl acetate extraction is added into hydrolyzate obtained in step (3), is concentrated, it is dry, obtain Quercetin extract A；
(5) methanol being added into Quercetin extract A to be completely dissolved to it, polyamide mixes sample, methanol is evaporated into dry, dress column,
It connects in the progress of MCI column and presses separation, eluted using percent by volume for the methanol aqueous solution of 40-100% as eluent gradient, thin layer
Chromatography detection collects and merges the eluent that flowing phase concentration is 65-69%, is concentrated under reduced pressure, obtains crude product A；
(6) methanol is added into crude product A to being completely dissolved, mixes sample with polyamide, methanol is evaporated into dry, be transferred to polyamide chromatography
Column is separated, and is eluted with the chloroform-methanol that volume ratio is 3-1:1, thin-layered chromatography detection, is collected to merge and is contained Mongolian oak
The eluent of Pi Su is concentrated under reduced pressure, and obtains crude product B；
(7) crude product B is dissolved in methanol, suspension is made in the water that equivalent methanol volume is added, with Sephadex LH-20 gel
Chromatography is eluted with methanol, and thin-layered chromatography detection collects and merges the eluent containing Quercetin, be concentrated under reduced pressure, obtains
Crude product C；
(8) gained crude product C is eluted with chloroform-acetone that volume ratio is 9-7:1-3 through silica gel chromatography, is collected and merges
Eluent containing Quercetin is concentrated under reduced pressure, dry, obtains Quercetin product.
2. the method according to claim 1 for preparing Quercetin from tungoiltree juvenile leaf, it is characterised in that described in step (1)
Alcoholic solution is any one or more in methanol, ethyl alcohol and n-butanol.
3. the method according to claim 1 for preparing Quercetin from tungoiltree juvenile leaf, it is characterised in that described in step (1)
The weight ratio of alcoholic solution and tungoiltree juvenile leaf is 3:1.
4. the method according to claim 1 for preparing Quercetin from tungoiltree juvenile leaf, it is characterised in that described in step (1)
The temperature of extraction is 40 DEG C ~ 50 DEG C；The time of the extraction is 20 ~ 40min.
5. the method according to claim 1 for preparing Quercetin from tungoiltree juvenile leaf, it is characterised in that described in step (2)
Acid solution is HCl solution or H2SO4Any one in solution.
6. the method according to claim 1 for preparing Quercetin from tungoiltree juvenile leaf, it is characterised in that described in step (4)
The volume ratio of hydrolyzate and ethyl acetate is 1:1-2.
7. the method according to claim 1 for preparing Quercetin from tungoiltree juvenile leaf, it is characterised in that described in step (5)
The mass ratio of Quercetin extract A and polyamide is 1:2-4.
8. the method for Quercetin is prepared in the slave tungoiltree juvenile leaf according to claim 1, it is characterised in that in step (5),
The MCI column specification is 70 × 460mm, and packing material is MCI-gel CHP-20P, column chromatography condition are as follows: column pressure is
80Psi, flow rate of mobile phase 50mL/min, Detection wavelength 245nm；The mobile phase is that percent by volume is 40-
100% methanol aqueous solution.
9. the method according to claim 1 for preparing Quercetin from tungoiltree juvenile leaf, it is characterised in that described in step (6)
The mass ratio of crude product A and polyamide is 1:2-4.
10. the method according to claim 1, it is characterised in that in step (6), the specification of the polyamide is 200-
300 mesh.
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