CN108409817A - A method of preparing Quercetin -3-D- xylosides and Quercetin -3-D- Arabinosides - Google Patents

A method of preparing Quercetin -3-D- xylosides and Quercetin -3-D- Arabinosides Download PDF

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Publication number
CN108409817A
CN108409817A CN201810464120.5A CN201810464120A CN108409817A CN 108409817 A CN108409817 A CN 108409817A CN 201810464120 A CN201810464120 A CN 201810464120A CN 108409817 A CN108409817 A CN 108409817A
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quercetin
arabinosides
xylosides
purity
phase
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魏芸
路艳珍
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Beijing University of Chemical Technology
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Beijing University of Chemical Technology
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    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00Processes for the preparation of sugar derivatives
    • C07H1/06Separation; Purification
    • C07H1/08Separation; Purification from natural products
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C07H17/06Benzopyran radicals
    • C07H17/065Benzo[b]pyrans
    • C07H17/07Benzo[b]pyran-4-ones

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Abstract

The method for preparing 3 D Arabinosides of 3 D xylosides of high-purity monomer Quercetin and Quercetin being detached from 75% ethyl alcohol water extract of agricultural product castoff apple leaf with the positive reverse phase high-speed countercurrent chromatography of cycle joint the present invention relates to a kind of;It is that the positive reverse phase high-speed countercurrent chromatography of joint detaches preparation 3 D xylosides of high-purity quercetin from 75% ethyl alcohol water extract of apple leaf and 3 D Arabinosides of Quercetin, solvent composition are made of three components using recycling:It is made of ethyl acetate, methanol or acetonitrile or ethyl alcohol or n-butanol and water;Volume ratio is:10‑25:1‑4:10‑25;It is suitable for preparing 3 D Arabinosides of 3 D xylosides of Quercetin and Quercetin using the high-speed counter-current chromatograph separation of various models, directly it can reach 96% or more into a large amount of crude products, 3 D xylosides of Quercetin and 3 D Arabinosides separation purity of Quercetin.This method is easy to operate, and cost is relatively low, good separating effect, in agricultural product active ingredient isolate and purify and high value added utilization provides new thinking.

Description

A kind of Quercetin -3-D- xylosides and Quercetin -3-D- Arabinosides of preparing Method
Technical field
Positive reverse phase high-speed countercurrent chromatography is combined from agricultural product castoff apple leaf 75% using cycle the present invention relates to a kind of Separation prepares the side of high-purity monomer Quercetin -3-D- xylosides and Quercetin -3-D- Arabinosides in alcohol-water extract Method.
Background technology
Apple rose section(Rosaceae)Malus(Malus)Plant is the first big fruit variety in current China, is born in Plain wilderness, loess hill and the hillside etc. of 50-2500 meters of height above sea level, originate in Europe and Asia middle part, China Gansu, The extensive growing and cultivation in the ground such as Shaanxi, Shandong, Hebei, Liaoning, Sichuan, Jiangsu, Yunnan, Tibet, nearly 2,000,000 square thousand of cultivated area Rice, cultivated area and yield accounts for the 40% of the world, occupies China first place, is that rare to occupy competition in the international market excellent in China The agricultural product of gesture.Apple leaf is the leaf of rosaceous plant apple, apple leaf taste bitter and cold, and removing pattogenic heat from the blood and toxic material from the body cures mainly postpartum anemic fainting, the moon Through uncomfortable, fever, heat toxin sore valve, scald etc..It falls leaves every year as the harvest of apple can all generate a large amount of apple, only Shaanxi Province The annual apple leaf for just generating ten thousand tons about more than 200, the probability that apple leaf is used effectively is very low, can be taken as on a small quantity medicinal material, Feed, fertilizer, fuel, other are largely all directly taken as garbage disposal, cause massive losses and the waste of resource, simultaneously also Can rot, souring, fouling, serious pollution is caused to environment.The study found that containing a large amount of more in these discarded apple leafs Phenolic active components, such as phloridzin, quercitin, isoquercitrin, Quercetin -3-D- xylosides, Quercetin -3-D- Arabinosides Deng, and show anti-oxidant, antibacterial anti-inflammatory, antiviral, antiallergy, protect liver, protection angiocarpy, anticancer, anti-diabetic and god Through bioactivity such as protective effects, it is with a wide range of applications in newtype drug and natural health care exploitation.Therefore, from Extracting and developing, purified polyphenol active constituent, probe into its bioactivity in apple leaf, develop its practical application, can not only become useless High-valued utilization for precious, raising apple utilization ratio, realization to agricultural food product, while can also reduce and environment is made At pollution, have great economic value and social benefit.Quercetin -3-D- xylosides in main extraction apple leaf herein With Quercetin -3-D- Arabinosides, they belong to the flavonoid glycoside compound in polyphenol, have very strong antioxidant activity.
Existing literature reports the method master for isolating and purifying Quercetin -3-D- xylosides and Quercetin -3-D- Arabinosides There are Amberlyst process, preparative liquid chromatography and high-speed countercurrent chromatography etc., wherein Amberlyst process disengaging time is long, operation Complex steps consume a large amount of organic solvent, it is difficult to obtain the monomer of extreme high purity, there are instrument and equipments for preparative liquid chromatography The problems such as costliness, sample preparation amount is few, it is difficult to which for isolating and purifying for a large amount of samples, and prepared by high speed adverse current chromatogram separation Method then can be with simple and quick cheap acquisition high-purity monomer.High speed adverse current chromatogram is that one kind for growing up in recent years is continuous Efficient, the quick liquid liquid partition chromatography isolation technics without any solid support, it avoids solid state adhesion body or load The various problems that body is brought --- sample ensures higher peak type resolution easily by absorption, loss and denaturation, fractional dose is big, sample without Loss, rate of recovery height, isolating environment mitigate, and save solvent.High-speed counter-current chromatograph can directly into a large amount of Natural Product Samples or Synthetic mixture, separating resulting can reach quite high purity, or even can directly connect the instruments such as mass spectrograph, be widely used to give birth to The preparative separation of the fields such as object, medicine, environmental protection chemical substance and purifying.
The present invention establishes cycle and combines positive 75% alcohol-water of reverse phase high-speed countercurrent chromatography separation and purification of apple leaf extraction The method of Quercetin -3-D- xylosides and Quercetin -3-D- Arabinosides in object.This method is easy to operate, simple and easy to do, and Process is mild, and separative efficiency is high, has to Quercetin -3-D- xylosides and isolating and purifying for Quercetin -3-D- Arabinosides Practical significance also provides for the high value added utilization of agricultural product with reference to thinking.
Invention content
The purpose of the present invention is the apple leaf crude products extracted using 75% alcohol-water as raw material, combines positive reverse phase height by recycling The method of fast adverse current chromatogram isolates and purifies to obtain Quercetin -3-D- xylosides and Quercetin -3-D- Arabinoside monomers, purity 96% or more.
The scheme of the invention is:The apple leaf extract that 75% alcohol-water refluxing extraction obtains, it is positive and negative by recycling joint Phase high-speed countercurrent chromatography detaches the Quercetin -3-D- xylosides and Quercetin -3-D- Arabinosides for preparing high-purity.Choosing Immiscible two phase solvent system is selected, is made of three components, component A is ethyl acetate, and B component is methanol or acetonitrile or second Alcohol or n-butanol, component C are water, adjust A:B:The volume ratio of tri- components of C is 10-25:1-4:10-25.It is washed first using reverse phase Mold-relieving type, i.e., upper to be mutually used as stationary phase, lower phase isolates Quercetin -3-D- Arabinosides and phloridzin as mobile phase Mixture, then the modal cutoff by recycling high speed adverse current chromatogram go out Quercetin -3-D- Arabinosides, then invert instrument, It is using positive elution mode, i.e., upper to be mutually used as mobile phase, Quercetin -3-D- xylosides are isolated, by this cycle joint The high speed adverse current chromatogram elution mode of lower phase isolates and purifies to obtain high-purity quercetin -3-D- xylosides and Quercetin -3-D- Ahs Draw primary glucosides.
Above-mentioned dicyandiamide solution is formulated in separatory funnel by volume first, shakes up rear stratification.One section of ready to balance After time, upper and lower phase is separated.Using analytic type or semi-preparative high-speed counter-current chromatograph, pumped equipped with NS-1007,2mL Or 20mL sampling valves, polytetrafluoroethylene (PTFE) column, column volume 40mL, 220 or 240mL, 500mL, 8823A-UV UV detector, 3057 Portable type recorders of Yokogawa.Apple Leave extract is dissolved in mobile phase for use.Before sample introduction, stationary phase is first used It is filled with entire pillar, adjustment engine speed is 500-1800 rpm, and mobile phase is pumped into column with the flow velocity of 0.5-3.0mL/min It is interior, after whole system establishes dynamic equilibrium, by sample introduction valve injection;Then according to detector uv atlas, target component is received.
With this method detach Quercetin -3-D- xylosides and Quercetin -3-D- Arabinoside purity can reach 96% with On.Suitable for preparing Quercetin -3-D- xylosides and Quercetin -3-D- Arab using the counter-current chromatograph separation of various models Glucosides monomer, can be directly into the product that largely slightly get sample, and separating resulting can reach high purity.
Specific implementation mode
Embodiment 1
It chooses acetate-methanol-water and carrys out separation and purification of apple leaf extract on semi-preparative counter-current chromatograph GS10AB (The apple leaf raw material of 75% alcohol-water extraction), 10 are pressed first:1:Above-mentioned solvent composition is formulated in separatory funnel by 10 volume ratios In, shake up rear stratification.Ready to balance for a period of time after, upper and lower phase is separated spare.Using semi-preparative high-speed counter-current Chromatograph pumps, 20 mL sampling valves, polytetrafluoroethylene (PTFE) column equipped with NS-1007, and column volume is 240 mL, 8823A-UV ultraviolet detections Device, 3057 Portable type recorders of Yokogawa.The apple Leave extract for weighing the extraction of 200 mg, 75% alcohol-waters is dissolved in 5mL It is mixed in solution for use under upper phase and 5mL.Before sample introduction, it first is filled with entire pillar with stationary phase, adjustment engine speed is Mobile phase is pumped into column by 800rpm with the flow velocity of 2.0 mL/min;After whole system establishes dynamic equilibrium, by sampling valve into Sample;Reverse phase elution mode is used first, i.e., lower is mutually mobile phase, isolates Quercetin -3-D- Arabinosides and phloridzin Mixture, then the modal cutoff by recycling high speed adverse current chromatogram go out Quercetin -3-D- Arabinosides, then invert instrument, Using positive elution mode, i.e., upper is mutually mobile phase, isolates Quercetin -3-D- xylosides;It is connect according to detector uv atlas Receive target component;HPLC detects Quercetin -3-D- xylosides and Quercetin -3-D- Arabinoside purity reaches 96% or more.
Embodiment 2
It chooses ethyl acetate-acetonitrile-water and carrys out separation and purification of apple leaf extract on semi-preparative counter-current chromatograph GS10A(75% The apple leaf raw material of alcohol-water extraction), 10 ︰ 1 are pressed first:Above-mentioned solvent composition is formulated in separatory funnel by 25 volume ratios, is shaken Stratification after even.Ready to balance for a period of time after, upper and lower phase is separated spare.Using semi-preparative high speed adverse current chromatogram Instrument pumps, 20mL sampling valves, polytetrafluoroethylene (PTFE) column, column volume 220mL, 8823A-UV UV detector equipped with NS-1007, 3057 Portable type recorders of Yokogawa.The apple Leave extract for weighing the extraction of 179.5 mg, 75% alcohol-waters is dissolved in 5 mL Upper phase with mixed under 5 mL in solution it is for use.Before sample introduction, it first is filled with entire pillar with stationary phase, adjustment engine speed is 800 Mobile phase is pumped into column by rpm with the flow velocity of 1.5 mL/min;After whole system establishes dynamic equilibrium, by sample introduction valve injection; Reverse phase elution mode is used first, i.e., lower is mutually mobile phase, isolates the mixing of Quercetin -3-D- Arabinosides and phloridzin Object, then the modal cutoff by recycling high speed adverse current chromatogram go out Quercetin -3-D- Arabinosides, then invert instrument, use Positive elution mode, i.e., it is upper to be mutually used as mobile phase, isolate Quercetin -3-D- xylosides;It is received according to detector uv atlas Target component;HPLC detects Quercetin -3-D- xylosides and Quercetin -3-D- Arabinoside purity reaches 96% or more.
Embodiment 3
It chooses acetate-methanol-water and carrys out separation and purification of apple leaf extract on semi-preparative counter-current chromatograph EMC-500 (The apple leaf raw material of 75% alcohol-water extraction), 10 are pressed first:3:Above-mentioned solvent composition is formulated in separatory funnel by 10 volume ratios In, shake up rear stratification.Ready to balance for a period of time after, upper and lower phase is separated spare.Using semi-preparative high-speed counter-current Chromatograph pumps, 20 mL sampling valves, polytetrafluoroethylene (PTFE) column equipped with NS-1007, and column volume is 500 mL, 8823A-UV ultraviolet detections Device, 3057 Portable type recorders of Yokogawa.The apple Leave extract for weighing the extraction of 400.1 mg, 75% alcohol-waters is dissolved in 5mL it is upper mutually with mixed under 5mL in solution it is for use.Before sample introduction, it first is filled with entire pillar with stationary phase, adjustment engine speed is Mobile phase is pumped into column by 1000 rpm with the flow velocity of 2.5 mL/min;After whole system establishes dynamic equilibrium, by sampling valve Sample introduction;Reverse phase elution mode is used first, i.e., lower is mutually mobile phase, isolates Quercetin -3-D- Arabinosides and phloridzin Mixture, then by recycle high speed adverse current chromatogram modal cutoff go out Quercetin -3-D- Arabinosides, then invert instrument Device, it is using positive elution mode, i.e., upper to be mutually used as mobile phase, isolate Quercetin -3-D- xylosides;According to detector UV spectrum Figure receives target component;HPLC detects Quercetin -3-D- xylosides and Quercetin -3-D- Arabinoside purity reaches 96% More than.
Embodiment 4
It chooses ethyl acetate-acetonitrile-water and carrys out separation and purification of apple leaf extract on semi-preparative counter-current chromatograph GS10AB (The apple leaf raw material of 75% alcohol-water extraction), 10 are pressed first:3:Above-mentioned solvent composition is formulated in separatory funnel by 25 volume ratios In, shake up rear stratification.Ready to balance for a period of time after, upper and lower phase is separated spare.Using semi-preparative high-speed counter-current Chromatograph pumps, 20 mL sampling valves, polytetrafluoroethylene (PTFE) column equipped with NS-1007, and column volume is 240 mL, 8823A-UV ultraviolet detections Device, 3057 Portable type recorders of Yokogawa.The apple Leave extract for weighing the extraction of 134.6 mg, 75% alcohol-waters is dissolved in 5 ML it is upper mutually with mixed under 5 mL in solution it is for use.Before sample introduction, it first is filled with entire pillar with stationary phase, adjustment engine speed is Mobile phase is pumped into column by 1000 rpm with the flow velocity of 2.0 mL/min;After whole system establishes dynamic equilibrium, by sampling valve Sample introduction;Reverse phase elution mode is used first, i.e., lower is mutually mobile phase, isolates Quercetin -3-D- Arabinosides and phloridzin Mixture, then by recycle high speed adverse current chromatogram modal cutoff go out Quercetin -3-D- Arabinosides, then invert instrument Device, it is using positive elution mode, i.e., upper to be mutually used as mobile phase, isolate Quercetin -3-D- xylosides;According to detector UV spectrum Figure receives target component;HPLC detects Quercetin -3-D- xylosides and Quercetin -3-D- Arabinoside purity reaches 96% More than.
Embodiment 5
It chooses acetate-methanol-water and carrys out separation and purification of apple leaf extract on semi-preparative counter-current chromatograph GS10AB (The apple leaf raw material of 75% alcohol-water extraction), 25 are pressed first:1:Above-mentioned solvent composition is formulated in separatory funnel by 10 volume ratios In, shake up rear stratification.Ready to balance for a period of time after, upper and lower phase is separated spare.Using semi-preparative high-speed counter-current Chromatograph pumps, 20 mL sampling valves, polytetrafluoroethylene (PTFE) column equipped with NS-1007, and column volume is 240 mL, 8823A-UV ultraviolet detections Device, 3057 Portable type recorders of Yokogawa.The apple Leave extract for weighing the extraction of 299.7 mg, 75% alcohol-waters is dissolved in 5 ML it is upper mutually with mixed under 5 mL in solution it is for use.Before sample introduction, it first is filled with entire pillar with stationary phase, adjustment engine speed is Mobile phase is pumped into column by 800 rpm with the flow velocity of 2.0 mL/min;After whole system establishes dynamic equilibrium, by sampling valve Sample introduction;Reverse phase elution mode is used first, i.e., lower is mutually mobile phase, isolates Quercetin -3-D- Arabinosides and phloridzin Mixture, then by recycle high speed adverse current chromatogram modal cutoff go out Quercetin -3-D- Arabinosides, then invert instrument Device, it is using positive elution mode, i.e., upper to be mutually used as mobile phase, isolate Quercetin -3-D- xylosides;According to detector UV spectrum Figure receives target component;HPLC detects Quercetin -3-D- xylosides and Quercetin -3-D- Arabinoside purity reaches 96% More than.
Embodiment 6
It chooses acetate-methanol-water and carrys out separation and purification of apple leaf extract on semi-preparative counter-current chromatograph GS10A(75% The apple leaf raw material of alcohol-water extraction), 25 are pressed first:1:Above-mentioned solvent composition is formulated in separatory funnel by 25 volume ratios, is shaken Stratification after even.Ready to balance for a period of time after, upper and lower phase is separated spare.Using semi-preparative high speed adverse current chromatogram Instrument, equipped with NS-1007 pump, 20 mL sampling valves, polytetrafluoroethylene (PTFE) column, column volume be 220 mL, 8823A-UV UV detector, 3057 Portable type recorders of Yokogawa.The apple Leave extract for weighing the extraction of 150.7 mg, 75% alcohol-waters is dissolved in 5 mL Upper phase with mixed under 5 mL in solution it is for use.Before sample introduction, it first is filled with entire pillar with stationary phase, adjustment engine speed is 800 Mobile phase is pumped into column by rpm with the flow velocity of 3.0mL/min;After whole system establishes dynamic equilibrium, by sample introduction valve injection; Reverse phase elution mode is used first, i.e., lower is mutually mobile phase, isolates the mixing of Quercetin -3-D- Arabinosides and phloridzin Object, then the modal cutoff by recycling high speed adverse current chromatogram go out Quercetin -3-D- Arabinosides, then invert instrument, use Positive elution mode, i.e., it is upper to be mutually used as mobile phase, isolate Quercetin -3-D- xylosides;It is received according to detector uv atlas Target component;HPLC detects Quercetin -3-D- xylosides and Quercetin -3-D- Arabinoside purity reaches 96% or more.
Embodiment 7
It chooses acetate-methanol-water and carrys out separation and purification of apple leaf extract on analytic type counter-current chromatograph GS20(75% second The apple leaf raw material of alcohol-water extraction), 25 are pressed first:3:Above-mentioned solvent composition is formulated in separatory funnel by 10 volume ratios, is shaken up Stratification afterwards.Ready to balance for a period of time after, upper and lower phase is separated spare.Using analytic type counter-current chromatograph, it is furnished with NS- 1007 pumps, 2mL sampling valves, polytetrafluoroethylene (PTFE) column, column volume are 40 mL, 8823A-UV UV detector, Yokogawa 3057 Portable type recorder.The apple Leave extract for weighing the extraction of 30.1mg75% alcohol-waters is dissolved in 1 mL on phase and is mutually mixed under 1 mL It closes for use in solution.Before sample introduction, it first is filled with entire pillar with stationary phase, adjustment engine speed is 1800rpm, with 0.5mL/min Flow velocity mobile phase is pumped into column;After whole system establishes dynamic equilibrium, by sample introduction valve injection;Reverse phase is used to elute first Pattern, i.e., lower is mutually mobile phase, isolates the mixture of Quercetin -3-D- Arabinosides and phloridzin, then high by recycling The modal cutoff of fast adverse current chromatogram goes out Quercetin -3-D- Arabinosides, then inverts instrument, using positive elution mode, i.e., Upper phase isolates Quercetin -3-D- xylosides as mobile phase;Target component is received according to detector uv atlas;HPLC is examined It surveys Quercetin -3-D- xylosides and Quercetin -3-D- Arabinoside purity reaches 96% or more.
Embodiment 8
It chooses acetate-methanol-water and carrys out separation and purification of apple leaf extract on semi-preparative counter-current chromatograph GS10AB (The apple leaf raw material of 75% alcohol-water extraction), 25 are pressed first:3:Above-mentioned solvent composition is formulated in separatory funnel by 25 volume ratios In, shake up rear stratification.Ready to balance for a period of time after, upper and lower phase is separated spare.Using semi-preparative high-speed counter-current Chromatograph pumps, 20 mL sampling valves, polytetrafluoroethylene (PTFE) column equipped with NS-1007, and column volume is 240 mL, 8823A-UV ultraviolet detections Device, 3057 Portable type recorders of Yokogawa.The apple Leave extract for weighing the extraction of 240 mg, 75% alcohol-waters is dissolved in 5mL It is mixed in solution for use under upper phase and 5mL.Before sample introduction, it first is filled with entire pillar with stationary phase, adjustment engine speed is Mobile phase is pumped into column by 725rpm with the flow velocity of 2.1 mL/min;After whole system establishes dynamic equilibrium, by sampling valve into Sample;Reverse phase elution mode is used first, i.e., lower is mutually mobile phase, isolates Quercetin -3-D- Arabinosides and phloridzin Mixture, then the modal cutoff by recycling high speed adverse current chromatogram go out Quercetin -3-D- Arabinosides, then invert instrument, It is using positive elution mode, i.e., upper to be mutually used as mobile phase, isolate Quercetin -3-D- xylosides;According to detector uv atlas Receive target component;HPLC detect Quercetin -3-D- xylosides and Quercetin -3-D- Arabinosides purity reach 96% with On.
Embodiment 9
It chooses acetate-methanol-water and carrys out separation and purification of apple leaf extract on semi-preparative counter-current chromatograph GS10AB (The apple leaf raw material of 75% alcohol-water extraction), 5 are pressed first:2:Above-mentioned solvent composition is formulated in separatory funnel by 5 volume ratios, Shake up rear stratification.Ready to balance for a period of time after, upper and lower phase is separated spare.Using semi-preparative high speed adverse current chromatogram Instrument, equipped with NS-1007 pump, 20 mL sampling valves, polytetrafluoroethylene (PTFE) column, column volume be 240 mL, 8823A-UV UV detector, 3057 Portable type recorders of Yokogawa.The apple Leave extract for weighing the extraction of 230 mg, 75% alcohol-waters is dissolved on 5mL Mutually with mixed under 5mL in solution it is for use.Before sample introduction, it first is filled with entire pillar with stationary phase, adjustment engine speed is 725rpm, Mobile phase is pumped into column with the flow velocity of 2.1 mL/min;After whole system establishes dynamic equilibrium, by sample introduction valve injection;First Using reverse phase elution mode, i.e., lower is mutually mobile phase, isolates the mixture of Quercetin -3-D- Arabinosides and phloridzin, Go out Quercetin -3-D- Arabinosides by recycling the modal cutoff of high speed adverse current chromatogram again, instrument is then inverted, using positive Elution mode, i.e., it is upper to be mutually used as mobile phase, isolate Quercetin -3-D- xylosides;Target is received according to detector uv atlas Ingredient;HPLC detects Quercetin -3-D- xylosides and Quercetin -3-D- Arabinoside purity reaches 96% or more.

Claims (1)

1. a kind of method preparing Quercetin -3-D- xylosides and Quercetin -3-D- Arabinosides, it is characterised in that:It is Positive reverse phase high-speed countercurrent chromatography separation from 75% alcohol-water extract of apple leaf is combined using cycle and prepares Quercetin -3-D- Xyloside and Quercetin -3-D- Arabinosides, separation purity can reach 96% or more, and solvent composition is by three component structures At:Ethyl acetate, methanol or acetonitrile or ethyl alcohol or n-butanol and water, volume ratio are followed successively by 10-25:1-4 :10-25.
CN201810464120.5A 2018-05-15 2018-05-15 A method of preparing Quercetin -3-D- xylosides and Quercetin -3-D- Arabinosides Pending CN108409817A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108997455A (en) * 2018-09-07 2018-12-14 淮安安莱生物科技有限公司 A kind of preparation method of tobira glycosides A1

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108997455A (en) * 2018-09-07 2018-12-14 淮安安莱生物科技有限公司 A kind of preparation method of tobira glycosides A1

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Application publication date: 20180817