CN105924482A - Method for extracting phloretin from camellia oleifera leaves - Google Patents
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- CN105924482A CN105924482A CN201610281277.5A CN201610281277A CN105924482A CN 105924482 A CN105924482 A CN 105924482A CN 201610281277 A CN201610281277 A CN 201610281277A CN 105924482 A CN105924482 A CN 105924482A
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- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
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- 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 provides a method for extracting phloretin from camellia oleifera leaves. The method comprises the following steps: with an ethanol solution as a solvent, and subjecting the camellia oleifera leaves to extraction so as to obtain a crude extract; and carrying out separation with D101 macroporous adsorption resin as a filling material, then carrying out silica-gel chromatographic separation, and carrying out DAC column chromatographic separation, silica-gel chromatographic separation and C18 column chromatographic separation so as to obtain a mixture only containing phloretin. The method provided by the invention successfully extracts phloretin from genus camellia plants for the first time; meanwhile, the extraction method provided by the invention has the advantages of high yield, high product purity, etc.
Description
Technical field
The present invention relates to medicine extractive technique field, especially relate to a kind of method extracting phloridzin from Camellia Leaves.
Background technology
Camellia Leaves is the leaf of plant of theaceae oil tea, and it is rich in multiple effective component, especially flavone compound, glycosides compound.Flavone compound has multiple biologically active, such as cardiovascular system activity, antibacterial and antiviral activity, antitumor activity, resisting oxidation free radical activity, analgesic activities, liver-protecting activity etc..Glycosides compound has the biologically actives such as expelling phlegm and arresting coughing, antitumor, antimycotic, antibacterial and norcholesterol.
How from Camellia Leaves, to extract the bioactive ingredients such as phloridzin, of crucial importance to deep development oil tea crop.
Summary of the invention
It is an object of the invention to provide the method extracting phloridzin from Camellia Leaves, described extracting method has successfully extracted phloridzin first from Camellia Leaves, and this extracting method has yield height, product purity advantages of higher.
For solving above-mentioned technical problem, the invention provides techniques below scheme:
The method extracting phloridzin from Camellia Leaves, comprises the following steps:
A: with ethanol solution as solvent, extracts Camellia Leaves, obtains crude extract；
B: with D101 macroporous absorbent resin as filler, carries out constant wash-out with water, 15-25wt% ethanol solution, 75-85wt% ethanol solution to described crude extract successively；
C: the eluent that described 75-85wt% ethanol solution affords is carried out silica gel column chromatography separation, methylene chloride-methanol with 10: 1～1: 3 carries out gradient elution, and Fractional Collections eluent, through chromatography, merge the stream part section containing phloridzin, named first order component；
D: use DAC chromatographic column, is that the most described first order component of flowing carries out constant wash-out, Fractional Collections eluent with 55-65% methanol-water, through chromatography, merges the stream part section containing phloridzin, named second order component；
E: described second order component is carried out silica gel column chromatography, carries out constant wash-out, Fractional Collections eluent with the methylene chloride-methanol-water of 90-110:10-14:1, through chromatography, merges the stream part section containing phloridzin, named 3rd order component；
F: use C18 chromatographic column, carries out constant wash-out, Fractional Collections eluent with 15-25% acetonitrile-water to described 3rd order component, through chromatography, merges the stream part section containing phloridzin.
Said extracted method is progressively isolated the pure substance of phloridzin by the thick mode to essence from Camellia Leaves.
On the basis of drier oil tealeaves, the present invention is to the recovery rate of phloridzin at more than 10.1mg/kg, and the purity of front and back product is all more than 90%.
The ratio of flowing phase of the present invention (i.e. eluting liquid used) refers both to volume ratio, " % " in flowing mutually refers to the percentage by volume shared by non-water substance, ethanol solution refers both to the aqueous solution of ethanol, such as, 15-25% ethanol solution refers to that ethanol percent by volume is the 15-25% aqueous solution.55-65% methanol-water nail alcohol percent by volume is the aqueous solution of 55-65%.
Constant wash-out of the present invention refers to that the proportion of composing of flowing phase is fixed.
Gradient elution of the present invention refers to constantly change the concentration proportioning of flowing phase in elution process, but initial concentration and endpoint concentration are fixing, such as the gradient elution in step C refers to: methylene chloride-methanol according to initial concentration be 9-11: 1, wash-out endpoint concentration be 1: 2.5-3.5 mode carry out gradient elution.
DAC chromatographic column spindle of the present invention is to dynamic compression process-scale chromatography post.
Extracting method of the present invention is applicable to the Camellia Leaves of different genera, is especially suitable for C. olelfera (Camellia oleifera Abel), and its recovery rate is high.
Each step of extracting method of the present invention can be improved, such as further:
In step A, the recovery rate of the impurity content in crude extract and active ingredient is all had an impact by the solvent used by extraction, solid-liquid ratio, temperature.Solvent is preferably with the ethanol-water solution of 40-60%, the ethanol-water solution of more preferably 50%.Solid-liquid ratio is preferably 1:2.5-3.5 (1g solid: 2.5-3.5mL solvent), more preferably 1:2.5-3.Extraction temperature is preferably 70-80 DEG C, and is optimal with backflow extraction.Use above extracting condition can reduce the impurity content in crude extract, improve the recovery rate of phloridzin.
It addition, for the difficulty reducing later stage separation, ethanol can be removed with concentrate drying crude extract after leaching.
In step B, the volume of each gradient elution flowing used phase is preferably 3.5-4.5 times of column volume, more preferably 4-4.5 times, it is ensured that composition to be extracted can be fully eluted out.The flowing preferred water of concentration of phase, 15-20% ethanol solution, 75-80% ethanol solution used.
In step C, silica gel column chromatography is separated into separation means, and chromatography is the means evaluating separating resulting, and both work in coordination, and filter out the eluent containing phloridzin Objective extraction thing.Screening usually coarse sizing, is usually through chromatography, is first merged by eluent similar for chromatogram, and then the standard items chromatogram with Objective extraction thing contrasts, and therefrom filters out the eluent containing Objective extraction thing, is merged.It is of course also possible to without merging, useful eluent is selected in direct and Objective extraction thing standard items chromatogram contrast, and this way workload is relatively big, but result is more accurate.
In described step C, the particle diameter of silica gel used is preferably 200-300 mesh, described gradient elution is preferably: carry out gradient elution with the methylene chloride-methanol of 9-10: 1 to 1: 2.5-3 gradient, uses the condition optimized further above, can improve separating degree and post effect.
In described step C, described silica gel column chromatography also includes before separating: the eluent concentrate drying afforded by described 75-85% ethanol solution, can avoid the ethanol interference to follow-up silica gel column chromatography.
It addition, the chromatography in described step C can be thin-layer chromatography (TLC), high performance liquid chromatography etc. arbitrarily can be used for method qualitatively, latter of which is more accurate.
It addition, when carrying out silica gel column chromatography, in order to ensure that material to be separated is dispersed among silica gel, preferably methylene chloride-methanol is diluted material to be separated, admixes silica gel, the most again water bath method simultaneously.Material after above process reinstalls in silicagel column and chromatographs.
Equally, in described step D, through chromatography can be: efficient liquid phase chromatographic analysis, and/or tlc analysis etc..
In described step D, flowing phase concentration preferred 55-60% methanol-water time, there is higher separating degree.
In described step E, the particle diameter of silica gel used is preferably 200-300 mesh, and the ratio of described methylene chloride-methanol-water is preferably 90-100:10-12:1, to improve separating degree and post effect.The chromatography used can be efficient liquid phase chromatographic analysis, tlc analysis etc..
In described step F, the concentration preferred 15-20% acetonitrile-water of flowing phase.The pure substance of phloridzin can be obtained in this step, as long as after chromatography, the stream part section containing only phloridzin is merged." only containing " herein, as long as referring to that the content of phloridzin reaches the general purity of extract, on this basis, can select to purify further according to Production requirement.
Compared with prior art, the present invention can reach techniques below effect:
(1) from Camellia Leaves, highly purified phloridzin it is extracted out first；
(2) by the large-scale promotion being slightly beneficial to extracting method to smart extracting mode；
(3) extract yield is high.
Accompanying drawing explanation
In order to be illustrated more clearly that the specific embodiment of the invention or technical scheme of the prior art, the accompanying drawing used required in detailed description of the invention or description of the prior art will be briefly described below, apparently, accompanying drawing in describing below is some embodiments of the present invention, for those of ordinary skill in the art, on the premise of not paying creative work, it is also possible to obtain other accompanying drawing according to these accompanying drawings.
The liquid chromatogram of the sample collected after 80% ethanol elution that Fig. 1 provides for the embodiment of the present invention 1；
Fig. 2 is final stream part that embodiment 1 obtains1H-NMR spectrum；
Fig. 3 is final stream part that embodiment 1 obtains13C-NMR spectrogram.
Detailed description of the invention
Below in conjunction with the drawings and specific embodiments, technical scheme is clearly and completely described, but it will be understood to those of skill in the art that, following described embodiment is a part of embodiment of the present invention, rather than whole embodiments, it is merely to illustrate the present invention, and is not construed as limiting the scope of the present invention.Based on the embodiment in the present invention, the every other embodiment that those of ordinary skill in the art are obtained under not making creative work premise, broadly fall into the scope of protection of the invention.Unreceipted actual conditions person in embodiment, the condition advised according to normal condition or manufacturer is carried out.Agents useful for same or instrument unreceipted production firm person, being can be by the commercially available conventional products bought and obtain.
The ratio of heretofore described flowing phase refers both to volume ratio.
Embodiment 1
The first step:
Naturally the oil tea dried in the shade is dried leaf and pulverizes 60 mesh sieves, take 20kg to be heated to reflux at 70-80 DEG C by solid-liquid ratio 1: 3 with 50% ethanol in two batches, repeat to extract 2 times, extract 2h every time, merge gained supernatant, filter and obtain supernatant, be evaporated to without alcohol taste, obtain about half crude extract sample of original volume, standby.
Second step:
With the D101 type macroporous absorbent resin of industry ethanol postincubation about 10L, wash with water without alcohol taste, the extract that the first step is obtained loading at twice, successively with water, 20% ethanol, 80% ethanol elution, 4 times of column volumes of each gradient elution, according to TLC and HPLC analysis result, each position merges concentration.
The sample concentration collected after 80% ethanol elution is dried that (about 150g, its HPLC spectrogram is as it is shown in figure 1, elution program: 0-10min50% methanol aqueous solution, 10-20min80% methanol aqueous solution, 20-21min100% methyl alcohol；Detection wavelength 254nm, sample size 10 μ L), it is dissolved in the methylene chloride-methanol of 10: 1, admixes 300g tlc silica gel (200～300 mesh), water-bath volatilizes, and fills post at twice, and wherein blanket layer loads silica gel about 800g every time.
nullFlow phase system is methylene chloride-methanol (10: 1 to 1: 3 gradient elution)，Every 500mL is collected as once，It is that 1-2+2 ' (represents: by first stream part of first time silicagel column through TLC combining data detection、Second stream part of second stream part and second time silicagel column merges)，3-7+3’-7’，8-10+8’-10’，11-13+11’，14-16+12’-13’，17-19+14’，20-22+15’-18’，19’-21’，23-26+22’-27’，27-40，28’-34’，35’-44’，41-47，48-64，65，66-67，68-70，71，72-78，45’-51’，52’-63’，64’-67’，68’-71’，72 '-84 ' amount to 24 components (stream part sequence number symbol " ' below of twice silicagel column " be distinguish between，Part stream part carries out cross-combining，With plus sige linking (using-linking with stream part of a silicagel column)，Such as，The extract of dress post is after wash-out for the first time，The liquid numbering collected is respectively 1、2……78，The extract of second time dress post is after wash-out，The liquid numbering collected is respectively 1 '、2’……84’).
3rd step:
27-40 utilizes DAC preparative chromatography to separate, the 60% constant wash-out of methanol-water, obtains compound CO-1 (56.4mg), CO-2 (39.2mg), CO-3 (9.1mg), and a complex component fr.A (865mg) containing multiple compounds.
4th step:
Fr.A flowing part be dissolved in a certain proportion of methylene chloride-methanol, admix 2.5g tlc silica gel (200-300 mesh), water-bath volatilizes, blanket layer filling silica gel about 40g.Flow phase system is methylene chloride-methanol-water (the constant wash-out of 100:12:1), and every 40mL is collected as a stream part, is 1,2,3,4-12 (the same second steps of method for numbering serial) through TLC combining data detection.
5th step:
The stream part 1 utilizing C18 chromatographic column to obtain the 4th step separates, the 20% constant wash-out of acetonitrile-water, compares HPLC spectrum analysis, collects the stream part (10.1mg) only containing phloridzin.
6th step: characterize extract
Final stream part is carried out nuclear magnetic resonance map detection,1H-NMR、13C-NMR is the most as shown in Figures 2 and 3.
?1In H-NMR, it is seen that two phenyl ring meta proton signal δ 5.95 (1H, d, J=2.0Hz) and δ 6.17 (1H, d, J=2.0Hz) are respectively belonging to H-3 ' and H-5 '；The aromatic signal δ 7.05 (1H, d, J=8.6Hz) of one group of AA ' BB ' Coupling System, δ 6.68 (1H, d, J=8.6Hz) is separately had to be respectively belonging to H-2,6 and H-3,5；δ 5.02 (1H, d, J=7.2Hz) is the anomeric proton signal of glucose.?13In C-NMR, it is seen that a ketone carbonyl carbon signals δ 205.1 and one group of glucosyl group carbon signal δ 100.5,73.2,77.0,69.6,76.9,60.9.The nuclear-magnetism figure of phloridzin carbon spectrum and hydrogen modal data reported with existing document compares, basically identical.Therefore, it is possible to identify the stream part finally given is phloridzin.
May determine that the final molecular formula such as following formula () flowing part in conjunction with above-mentioned characterization result, be phloridzin.
After testing, the purity of the phloridzin obtained is respectively 95.6%.
Embodiment 2
The first step:
Naturally the oil tea dried in the shade is dried leaf and pulverizes 60 mesh sieves, take 20kg to be heated to reflux at 70-80 DEG C by solid-liquid ratio 1: 2.5 with 40% ethanol in two batches, repeat to extract 2 times, extract 2h every time, merge gained supernatant, filter and obtain supernatant, be evaporated to without alcohol taste, obtain about half crude extract sample of original volume, standby.
Second step:
With the D101 type macroporous absorbent resin of industry ethanol postincubation about 10L, wash with water without alcohol taste, the extract that the first step is obtained loading at twice, successively with water, 15% ethanol, 75% ethanol elution, 4.5 times of column volumes of each gradient elution, according to TLC and HPLC analysis result, each position merges concentration.
The sample concentration collected after 80% ethanol elution is dried (about 150g), being dissolved in the methylene chloride-methanol of 10: 1, admix 300g tlc silica gel (200～300 mesh), water-bath volatilizes, filling post at twice, wherein blanket layer loads silica gel about 800g every time.
Flow phase system is methylene chloride-methanol (9: 1 to 1: 2.5 gradient elution), and every 500mL is collected as once, contains stream part section of phloridzin, named first order component through TLC combining data detection.
3rd step:
First order component utilizes DAC preparative chromatography to separate, the 55% constant wash-out of methanol-water, through chromatography, merges the complex component containing phloridzin, named second order component.
4th step:
Second order component being dissolved in a certain proportion of methylene chloride-methanol, admix 2.5g tlc silica gel (200-300 mesh), water-bath volatilizes, blanket layer filling silica gel about 40g.Flow phase system is methylene chloride-methanol-water (the constant wash-out of 90:10:1), and every 40mL is collected as a stream part, through TLC combining data detection, obtains the stream part section containing phloridzin, named 3rd order component.
5th step:
Utilize C18 chromatographic column that the 3rd order component is separated, the 15% constant wash-out of acetonitrile-water, compare HPLC spectrum analysis, collect the stream part (10.4) only containing phloridzin.
6th step: characterize extract
Equally, use mass spectrum and1H-NMR、13C-NMR characterizes, and result is same as in Example 1, and final stream part is phloridzin.
Embodiment 3
The first step:
Naturally the oil tea dried in the shade is dried leaf and pulverizes 60 mesh sieves, take 20kg to be heated to reflux at 70-80 DEG C by solid-liquid ratio 1: 3.5 with 60% ethanol in two batches, repeat to extract 2 times, extract 2h every time, merge gained supernatant, filter and obtain supernatant, be evaporated to without alcohol taste, obtain about half crude extract sample of original volume, standby.
Second step:
With the D101 type macroporous absorbent resin of industry ethanol postincubation about 10L, wash with water without alcohol taste, the extract that the first step is obtained loading at twice, successively with water, 25% ethanol, 85% ethanol elution, 3.5 times of column volumes of each gradient elution, according to TLC and HPLC analysis result, each position merges concentration.
The sample concentration collected after 80% ethanol elution is dried (about 150g), being dissolved in the methylene chloride-methanol of 10: 1, admix 300g tlc silica gel (200～300 mesh), water-bath volatilizes, filling post at twice, wherein blanket layer loads silica gel about 800g every time.
Flow phase system is methylene chloride-methanol (11: 1 to 1: 3.5 gradient elution), and every 500mL is collected as once, contains stream part section of phloridzin, named first order component through TLC combining data detection.
3rd step:
First order component utilizes DAC preparative chromatography to separate, the 65% constant wash-out of methanol-water, through chromatography, merges the complex component containing phloridzin glycosides, named second order component.
4th step:
Second order component being dissolved in a certain proportion of methylene chloride-methanol, admix 2.5g tlc silica gel (200-300 mesh), water-bath volatilizes, blanket layer filling silica gel about 40g.Flow phase system is methylene chloride-methanol-water (the constant wash-out of 110:14:1), and every 40mL is collected as a stream part, through TLC combining data detection, obtains the stream part containing phloridzin, named 3rd order component.
5th step:
Utilize C18 chromatographic column that the 3rd order component is separated, the 25% constant wash-out of acetonitrile-water, compare HPLC spectrum analysis, collect the stream part (9.7mg) only containing phloridzin.
6th step: characterize extract
Equally, use mass spectrum and1H-NMR、13C-NMR characterizes, and result is same as in Example 1, and final stream part is phloridzin.
Last it is noted that various embodiments above is only in order to illustrate technical scheme, it is not intended to limit；Although the present invention being described in detail with reference to foregoing embodiments, it will be understood by those within the art that: the technical scheme described in foregoing embodiments still can be modified by it, or the most some or all of technical characteristic is carried out equivalent；And these amendments or replacement, do not make the essence of appropriate technical solution depart from the scope of various embodiments of the present invention technical scheme.
Claims (10)
1. the method extracting phloridzin from Camellia Leaves, it is characterised in that comprise the following steps:
A: with ethanol solution as solvent, extracts Camellia Leaves, obtains crude extract；
B: with D101 macroporous absorbent resin as filler, successively with water, 15-25wt% ethanol solution,
75-85wt% ethanol solution carries out constant wash-out to described crude extract；
C: the eluent that described 75-85wt% ethanol solution affords is carried out silica gel column chromatography separation, uses
The methylene chloride-methanol of 10: 1～1: 3 carries out gradient elution, Fractional Collections eluent, divides through chromatogram
Analysis, merges the stream part section containing phloridzin, named first order component；
D: use DAC chromatographic column, is the most described first order component of flowing with 55-65% methanol-water
Carry out constant wash-out, Fractional Collections eluent, through chromatography, merge the stream part section containing phloridzin,
Named second order component；
E: described second order component is carried out silica gel column chromatography, with the dichloromethane of 90-110:10-14:1
Alkane-methanol-water carries out constant wash-out, Fractional Collections eluent, through chromatography, merges containing root skin
Stream part section of glucoside, named 3rd order component；
F: use C18 chromatographic column, carries out constant with 15-25% acetonitrile-water to described 3rd order component
Wash-out, Fractional Collections eluent, through chromatography, merge the stream part section containing phloridzin.
The method extracting phloridzin from Camellia Leaves the most according to claim 1, it is characterised in that
In described step A, the method for extraction is: solid-liquid ratio is 1:3, refluxing extraction at 70-80 DEG C,
Ethanol solution is preferably the ethanol-water solution of 40-60%.
The method extracting phloridzin from Camellia Leaves the most according to claim 1, it is characterised in that
In described step B, 3.5-4.5 times that volume is column volume of each gradient elution flowing used phase.
The method extracting phloridzin from Camellia Leaves the most according to claim 1, it is characterised in that
In described step C, the particle diameter of silica gel used is 200-300 mesh；Chromatography used is preferably
TLC。
The method extracting phloridzin from Camellia Leaves the most according to claim 1, it is characterised in that
In described step D, described 55-65% methanol-water is preferably 55-60% methanol-water.
The method extracting phloridzin from Camellia Leaves the most according to claim 1, it is characterised in that
In described step E, the particle diameter of silica gel used is 200-300 mesh, described methylene chloride-methanol-water
Ratio be preferably 90-100:10-12:1.
The method extracting phloridzin from Camellia Leaves the most according to claim 1, it is characterised in that
In described step F, merge the stream part section containing phloridzin and be preferably: through liquid-phase chromatographic analysis, merge
Contain only stream part section of phloridzin.
The method extracting phloridzin from Camellia Leaves the most according to claim 1, it is characterised in that
In described step F, described acetonitrile-water is: 15-20% acetonitrile-water.
The method extracting phloridzin from Camellia Leaves the most according to claim 1, it is characterised in that
In described step C, described silica gel column chromatography also includes before separating: by molten for described 75-85wt% ethanol
The eluent concentrate drying that liquid affords.
The method extracting phloridzin from Camellia Leaves the most according to claim 1, its feature exists
In, in described step A, also include after described extraction: concentrate except alcohol.
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Application publication date: 20160907 |