CN110320307A - A kind of low temperature sample injection method of controllable punicalagins isomer proportion - Google Patents
A kind of low temperature sample injection method of controllable punicalagins isomer proportion Download PDFInfo
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- CN110320307A CN110320307A CN201910713229.2A CN201910713229A CN110320307A CN 110320307 A CN110320307 A CN 110320307A CN 201910713229 A CN201910713229 A CN 201910713229A CN 110320307 A CN110320307 A CN 110320307A
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- punicalagins
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/16—Injection
Abstract
The present invention relates to a kind of low temperature sample injection methods of controllable punicalagins isomer proportion, this method is based on the isomerization dynamics and thermodynamic study between two epimers of punicalagins, will be enriched in punicalagins pomegranate rind extract stable ratio is isomerizated into methanol, ethyl alcohol, isopropanol, acetonitrile, methanol-water or water respectively after, sample introduction to liquid chromatogram carries out separation analysis again, by applying low temperature environment during sample introduction to prevent its isomerization dynamic process, so that punicalagins be made to maintain the isomer proportion before sample introduction on a column.The result shows that low temperature sampling technique can effectively fix in the pomegranate rind extract after isomerization α-punicalagins and β-punicalagins ratio between 32-50:50-68.This method can make α-punicalagins or β punicalagins carry out artificial control increase and not reduce because of isomerization in chromatographic separation process, improve the yield in individual isomer α-punicalagins and β-punicalagins preparation process.
Description
Technical field
The present invention relates to a kind of low temperature sample injection method of controllable punicalagins isomer proportion, this method is based on pomegranate
Isomerization dynamics and thermodynamic study between two epimers of glycosides, will be enriched in the pomegranate rind extract of punicalagins molten
After being isomerizated into stable ratio in agent, then sample introduction to liquid chromatogram carries out separation analysis, by applying low temperature during sample introduction
Environment is to prevent its isomerization dynamic process, so that punicalagins be made to maintain the ratios of the isomers before sample introduction on a column
Example.This method can keep isomerization ratio of the punicalagins isomers in chromatographic separation process, can make α-punicalagins or β
Punicalagins carry out artificial control and increase and do not reduce because of isomerization in chromatographic separation process, and individual isomer can be improved
Yield in α-punicalagins and β-punicalagins preparation process.
Background technique
Isomer is that molecular weight is identical, and the different compound of structure, is widely present in natural products.Same point
Isomers it is many kinds of, wherein the structure for having several classes special, such as certain epimers and cis-trans-isomer, in certain condition
Under can mutually convert, ultimately form the admixture that two or more isomers coexists.Currently, to this isomerization
The research of reaction have been relatively mature deeply.The ratio formed after converting between isomers is a thermodynamic problems, mainly with molten
Agent type, pH, illumination, temperature are related.And by changing compound condition of storage, another fixed proportion is converted into from fixed proportion
Rate speed, then be a dynamics problem, depend primarily on type and temperature, sample concentration of catalyst etc..Temperature is got over
Height, conversion rate are faster.Can bioactivity between the isomers of isomerization it is often different, thus isomers mixing coexisting state
The ratio of lower mixture, Isomers is different, can also cause the difference of its bioactivity.Therefore, by isomers isomerization
The exploration of thermodynamics and kinetics rule, by the isomer mixture under coexisting state artificially, be selectively transformed into fixation
Ratio, then its secondary isomerization is prevented by applying low temperature environment, it can be made to can be controlled in fixed proportion within a certain period of time.This
The fixed method of kind ratio has positive meaning to the raising of the higher isomers yield of activity in the split process of isomers
Justice.
Punicalagins are a kind of using ellagic acid as parent nucleus, and the plant polyphenol of rich content, has in granatum medicinal material
The bioactivity such as good anti-inflammatory, antibacterial, antiviral, tissue cancer cell proliferation, are a kind of compounds for having very much patent medicine potentiality.Peace
In the structure of pomegranate glycosides, there are a glucosides, have an end carbon, can produce anomer, i.e. α-punicalagins
With two isomers of β-punicalagins, two individual isomers peaks are presented in chromatography.Can mutually it turn between two isomers
Change.Artificial control is carried out to α-punicalagins in punicalagins and β-punicalagins ratio there has been no document and is adjusted to fixed ratio
Example.The present invention is directed to the two isomers α-punicalagins and β-punicalagins thermodynamics and kinetics feature of punicalagins,
Sample introduction after punicalagins isomerization to fixed proportion is implemented into separation into liquid chromatogram, low temperature control is implemented during sample introduction
System guarantees stability of ratio during sample introduction between two isomers of punicalagins, can effectively hinder two between isomers
Secondary conversion, and then influence α-punicalagins and β-punicalagins preparation efficiency.The key point entirely invented is exactly low temperature sample introduction
The foundation of method simultaneously is used to maintain the ratio between punicalagins isomers, the fractionation to punicalagins isomers during sample introduction
In the process, there is positive meaning to the raising of the higher isomers yield of activity.The low temperature sample injection method established is suitable for can
Isomer proportion control during the separation of isomerization compound, strong innovation have certain demonstration.
Summary of the invention
The object of the present invention is to provide a kind of low temperature sample injection method of controllable punicalagins isomer proportion, the party
Method will be enriched in the pomegranate of punicalagins based on isomerization dynamics and thermodynamic study between two epimers of punicalagins
After bark extract is isomerizated into stable ratio respectively in methanol, ethyl alcohol, isopropanol, acetonitrile, methanol-water or water, then sample introduction is extremely
Liquid chromatogram carries out separation analysis, by application low temperature environment during sample introduction to prevent its isomerization dynamic process,
To make punicalagins maintain the isomer proportion before sample introduction on a column.The result shows that low temperature sampling technique can be effective
α-punicalagins and β-punicalagins ratio are between 32-50:50-68 in pomegranate rind extract after fixed isomerization.It should
Method can make α-punicalagins or β punicalagins carry out artificial control increase and in chromatographic separation process not because of isomerization
And reduce, improve the yield in individual isomer α-punicalagins and β-punicalagins preparation process.
A kind of low temperature sample injection method of controllable punicalagins isomer proportion of the present invention, follow these steps into
Row:
1mg pomegranate rind extract is weighed, is dissolved in water, methanol, ethyl alcohol, isopropanol, acetonitrile or the methanol-water of 1mL, Yu Wen
It spends in 70 DEG C of water-baths and heats 1h to drying, add 1mL water to dissolve, cross 0.45 μm of organic filter, placed at -4-10 DEG C of temperature
5min-5h, obtains that wherein punicalagins content is 32%, α-punicalagins and β-punicalagins ratio is 32-50:50-68；
Or 1mg pomegranate rind extract is taken, and it is dissolved in water, methanol, ethyl alcohol, isopropanol, acetonitrile or the methanol-water of 1mL, it is molten
In 1mL water, 0.45 μm of organic filter is crossed, 4 DEG C of refrigerator overnights of Yu Wendu are placed, and place 5min- at -4-10 DEG C of temperature
5h, obtains that wherein punicalagins content is 32%, α-punicalagins and β-punicalagins ratio is 32-50:50-68.
A kind of low temperature sample injection method of controllable punicalagins isomer proportion of the present invention, this method utilize peace stone
The characteristics of two isomers α-punicalagins of pomegranate glycosides and β punicalagins can mutually convert, by changing solvent condition isomerization extremely
Fixed proportion recycles the characteristics of isomerization rate is greatly lowered under low temperature environment, is first subject to low temperature control again to sample introduction process
Sample introduction is able to maintain the isomerization ratio before sample introduction during sample introduction.The low temperature sample injection method is controllable can isomerization substance
Isomer proportion during sample introduction, strong innovation have certain demonstration.
Specific embodiment
Combined with specific embodiments below, it is further elaborated on the present invention.
Embodiment 1
Weigh the granatum that punicalagins content is about 32%, α-punicalagins and β-punicalagins ratio is 42:58
Extract 1mg is dissolved in 1mL methanol, and 1h is heated in temperature 70 C water-bath to drying, adds 1mL water to dissolve, 0.45 μm excessively organic
Filter places 1h at 0 DEG C of temperature, is designated as sample 1；
Take analytic type reverse phase C18 chromatographic column, specification column length 250mm × internal diameter 4.6mm, 10 μm of packing material size, mobile phase is
- 0.1% formic acid water of methanol of volume ratio 12:88, flow velocity 0.6min/mL, 30 DEG C of temperature, ultraviolet detection wavelength is 254nm, is put down
Weigh 15min, for use；Take 20 μ L sample, 1 sample introduction into the chromatographic column balanced, wherein 12.5min to the peak between 15min is α-
Punicalagins, 27min to the peak between 32.5min are β-punicalagins.Measure wherein α-punicalagins (Aα) and β-punicalagins
(Aβ) peak area, calculate α-punicalagins and β-punicalagins ratio are 50:50.
Embodiment 2
Weigh the granatum that punicalagins content is about 32%, α-punicalagins and β-punicalagins ratio is 42:58
Extract 1mg is dissolved in 1mL water, crosses 0.45 μm of organic filter, is placed in 4 DEG C of refrigerator overnights of temperature, is transferred at 0 DEG C of temperature
30min is set, sample 2 is designated as；
Take analytic type reverse phase C18 chromatographic column, specification column length 250mm × internal diameter 4.6mm, 10 μm of packing material size, mobile phase is
- 0.1% formic acid water of methanol of volume ratio 12:88, flow velocity 0.6min/mL, 30 DEG C of temperature, ultraviolet detection wavelength is 254nm, is put down
Weigh 15min, for use；Take 20 μ L sample, 2 sample introduction into the chromatographic column balanced, wherein 12.5min to the peak between 15min is α-
Punicalagins, 27min to the peak between 32.5min are β-punicalagins, measure wherein α-punicalagins (Aα) and β-punicalagins
(Aβ) peak area, calculate α-punicalagins and β-punicalagins ratio are 32:68.
Embodiment 3
Weigh the granatum that punicalagins content is about 32%, α-punicalagins and β-punicalagins ratio is 42:58
Extract 1mg is dissolved in 1mL water, crosses 0.45 μm of organic filter, is placed in 4 DEG C of refrigerator overnights of temperature, is transferred at 10 DEG C of temperature
5h is set, sample 3 is designated as；
Take analytic type reverse phase C18 chromatographic column, specification column length 250mm × internal diameter 4.6mm, 10 μm of packing material size, mobile phase is
- 0.1% formic acid water of methanol of volume ratio 12:88, flow velocity 0.6min/mL, 30 DEG C of temperature, ultraviolet detection wavelength is 254nm, is put down
Weigh 15min, for use；Take 20 μ L sample, 3 sample introduction into the chromatographic column balanced, wherein 12.5min to the peak between 15min is α-
Punicalagins, 27min to the peak between 32.5min are β-punicalagins, measure wherein α-punicalagins (Aα) and β-punicalagins
(Aβ) peak area, calculate α-punicalagins and β-punicalagins ratio are 37:63.
Embodiment 4
Weigh the granatum that punicalagins content is about 32%, α-punicalagins and β-punicalagins ratio is 42:58
Extract 1mg is dissolved in 1mL water, crosses 0.45 μm of organic filter, and 4 DEG C of refrigerator overnights of Yu Wendu are placed, transferred at -4 DEG C of temperature
5min is set, sample 4 is designated as；
Take analytic type reverse phase C18 chromatographic column, specification column length 250mm × internal diameter 4.6mm, 10 μm of packing material size, mobile phase is
- 0.1% formic acid water of methanol of volume ratio 12:88, flow velocity 0.6min/mL, 30 DEG C of temperature, ultraviolet detection wavelength is 254nm, is put down
Weigh 15min, for use；Take 20 μ L sample, 4 sample introduction into the chromatographic column balanced, wherein 12.5min to the peak between 15min is α-
Punicalagins, 27min to the peak between 32.5min are β-punicalagins, measure wherein α-punicalagins (Aα) and β-punicalagins
(Aβ) peak area, calculate α-punicalagins and β-punicalagins ratio are 32:68.
Embodiment 5
Weigh the granatum that punicalagins content is about 32%, α-punicalagins and β-punicalagins ratio is 42:58
Extract 1mg is dissolved in 1mL methanol, and 1h is heated in temperature 70 C water-bath to drying, adds 1mL water to dissolve, 0.45 μm excessively organic
Filter places 5h at 10 DEG C of Yu Wendu, is designated as sample 5；
Take analytic type reverse phase C18 chromatographic column, specification column length 250mm × internal diameter 4.6mm, 10 μm of packing material size, mobile phase is
- 0.1% formic acid water of methanol of volume ratio 12:88, flow velocity 0.6min/mL, 30 DEG C of temperature, ultraviolet detection wavelength is 254nm, is put down
Weigh 15min, for use；Take 20 μ L sample, 5 sample introduction into the chromatographic column balanced, wherein 12.5min to the peak between 15min is α-
Punicalagins, 27min to the peak between 32.5min are β-punicalagins.Measure wherein α-punicalagins (Aα) and β-punicalagins
(Aβ) peak area, calculate α-punicalagins and β-punicalagins ratio are 48:52.
Embodiment 6
Weigh the granatum that punicalagins content is about 32%, α-punicalagins and β-punicalagins ratio is 42:58
Extract 1mg is dissolved in 1mL methanol, and 1h is heated in temperature 70 C water-bath to drying, adds 1mL water to dissolve, 0.45 μm excessively organic
Filter places 30min at Yu Wendu -4 DEG C, is designated as sample 6；
Take analytic type reverse phase C18 chromatographic column, specification column length 250mm × internal diameter 4.6mm, 10 μm of packing material size, mobile phase is
- 0.1% formic acid water of methanol of volume ratio 12:88, flow velocity 0.6min/mL, 30 DEG C of temperature, ultraviolet detection wavelength is 254nm, is put down
Weigh 15min, for use；Take 20 μ L sample, 6 sample introduction into the chromatographic column balanced, wherein 12.5min to the peak between 15min is α-
Punicalagins, 27min to the peak between 32.5min are β-punicalagins.Measure wherein α-punicalagins (Aα) and β-punicalagins
(Aβ) peak area, calculate α-punicalagins and β-punicalagins ratio are 50:50.
Embodiment 7
Weigh the granatum that punicalagins content is about 32%, α-punicalagins and β-punicalagins ratio is 42:58
Extract 1mg is dissolved in 1mL ethyl alcohol, and 1h is heated in temperature 70 C water-bath to drying, adds 1mL water to dissolve, 0.45 μm excessively organic
Filter places 2h at Yu Wendu -4 DEG C, is designated as sample 7；
Take analytic type reverse phase C18 chromatographic column, specification column length 250mm × internal diameter 4.6mm, 10 μm of packing material size, mobile phase is
- 0.1% formic acid water of methanol of volume ratio 12:88, flow velocity 0.6min/mL, 30 DEG C of temperature, ultraviolet detection wavelength is 254nm, is put down
Weigh 15min, for use；Take 20 μ L sample, 7 sample introduction into the chromatographic column balanced, wherein 12.5min to the peak between 15min is α-
Punicalagins, 27min to the peak between 32.5min are β-punicalagins.Measure wherein α-punicalagins (Aα) and β-punicalagins
(Aβ) peak area, calculate α-punicalagins and β-punicalagins ratio are 48:52.
Embodiment 8
Weigh the granatum that punicalagins content is about 32%, α-punicalagins and β-punicalagins ratio is 42:58
Extract 1mg is dissolved in 1mL isopropanol, and 1h is heated in temperature 70 C water-bath to drying, adds 1mL water to dissolve, crossing 0.45 μm has
Machine filter head places 3h at Yu Wendu -4 DEG C, is designated as sample 8；
Take analytic type reverse phase C18 chromatographic column, specification column length 250mm × internal diameter 4.6mm, 10 μm of packing material size, mobile phase is
- 0.1% formic acid water of methanol of volume ratio 12:88, flow velocity 0.6min/mL, 30 DEG C of temperature, ultraviolet detection wavelength is 254nm, is put down
Weigh 15min, for use；Take 20 μ L sample, 8 sample introduction into the chromatographic column balanced, wherein 12.5min to the peak between 15min is α-
Punicalagins, 27min to the peak between 32.5min are β-punicalagins.Measure wherein α-punicalagins (Aα) and β-punicalagins
(Aβ) peak area, calculate α-punicalagins and β-punicalagins ratio are 46:54.
Embodiment 9
Weigh the granatum that punicalagins content is about 32%, α-punicalagins and β-punicalagins ratio is 42:58
Extract 1mg is dissolved in 1mL acetonitrile, and 1h is heated in temperature 70 C water-bath to drying, adds 1mL water to dissolve, 0.45 μm excessively organic
Filter places 1h at 0 DEG C of Yu Wendu, is designated as sample 6；
Take analytic type reverse phase C18 chromatographic column, specification column length 250mm × internal diameter 4.6mm, 10 μm of packing material size, mobile phase is
- 0.1% formic acid water of methanol of volume ratio 12:88, flow velocity 0.6min/mL, 30 DEG C of temperature, ultraviolet detection wavelength is 254nm, is put down
Weigh 15min, for use；Take 20 μ L sample, 5 sample introduction into the chromatographic column balanced, wherein 12.5min to the peak between 15min is α-
Punicalagins, 27min to the peak between 32.5min are β-punicalagins.Measure wherein α-punicalagins (Aα) and β-punicalagins
(Aβ) peak area, calculate α-punicalagins and β-punicalagins ratio are 36:64.
Embodiment 10
Weigh the granatum that punicalagins content is about 32%, α-punicalagins and β-punicalagins ratio is 42:58
Extract 1mg is dissolved in the methanol-water of 1mL volume ratio 1:1, and 1h is heated in temperature 70 C water-bath to drying, adds 1mL water-soluble
Solution crosses 0.45 μm of organic filter, places 5min at Yu Wendu -4 DEG C, be designated as sample 10；
Take analytic type reverse phase C18 chromatographic column, specification column length 250mm × internal diameter 4.6mm, 10 μm of packing material size, mobile phase is
- 0.1% formic acid water of methanol of volume ratio 12:88, flow velocity 0.6min/mL, 30 DEG C of temperature, ultraviolet detection wavelength is 254nm, is put down
Weigh 15min, for use；Take 20 μ L sample, 10 sample introduction into the chromatographic column balanced, wherein 12.5min to the peak between 15min is α-
Punicalagins, 27min to the peak between 32.5min are β-punicalagins.Measure wherein α-punicalagins (Aα) and β-punicalagins
(Aβ) peak area, calculate α-punicalagins and β-punicalagins ratio are 48:52.
It is demonstrated experimentally that first designated solvent, at a temperature of isomerization, then by low temperature control sample introduction process, can efficiently use
The thermodynamics and kinetics feature of punicalagins isomerization, to realize prepared by α-punicalagins and β-punicalagins isomers
The variation of the isomery scale of construction in journey, to improve its preparation efficiency.
A kind of low temperature sample injection method of controllable punicalagins isomer proportion of the present invention, this method are not only suitable for
The isomerization process of methanol, aqueous systems, similarly suitable 1,2-PD, ethyl acetate, acetone, tetrahydrofuran, dimethyl sulfoxide,
Acetonitrile, isopropanol, propyl alcohol, ethyl alcohol, methanol-water mixtures (arbitrary proportion), ethanol-water mixture (arbitrary proportion), propyl alcohol-water
Mixture (arbitrary proportion), isopropanol-water mixture (arbitrary proportion), acetonitrile-water mixture (arbitrary proportion), dimethyl are sub-
Sulfone-aqueous mixtures (arbitrary proportion), acetone-water mixture (arbitrary proportion), tetrahydrofuran-aqueous mixtures (arbitrary proportion), 1,
The isomerization of punicalagins and low temperature empty wagons sample introduction process in 2- propylene glycol -- water mixture (arbitrary proportion).The low temperature sample introduction
Technology is also suitable for the isomer proportion sample introduction process control with isomers transferring structure in addition to suitable punicalagins.
A kind of low temperature sample injection method of controllable punicalagins isomer proportion of the present invention, low temperature control should control
It is between 10 DEG C to -100 DEG C in range.
A kind of low temperature sample injection method of controllable punicalagins isomer proportion of the present invention is low after sample isomerization
The temperature control time should control between 0 to 10 hour.
Claims (1)
1. a kind of low temperature sample injection method of controllable punicalagins isomer proportion, it is characterised in that follow these steps to carry out:
1 mg pomegranate rind extract is weighed, is dissolved in water, methanol, ethyl alcohol, isopropanol, acetonitrile or the methanol-water of 1mL, Yu Wendu
1h is heated in 70 DEG C of water-baths to drying, is added 1 mL water to dissolve, is crossed 0.45 μm of organic filter, place 5 at -4-10 DEG C of temperature
Min-5h, obtains that wherein punicalagins content is 32%, α-punicalagins and β-punicalagins ratio is 32-50:50-68；
Or 1 mg pomegranate rind extract is taken, it is dissolved in water, methanol, ethyl alcohol, isopropanol, acetonitrile or the methanol-water of 1mL, is dissolved in 1
In mL water, 0.45 μm of organic filter is crossed, 4 DEG C of refrigerator overnights of Yu Wendu are placed, 5 min-5h are placed at -4-10 DEG C of temperature,
Obtain that wherein punicalagins content is 32%, α-punicalagins and β-punicalagins ratio is 32-50:50-68.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110801460A (en) * | 2019-11-18 | 2020-02-18 | 中国科学院新疆理化技术研究所 | Preparation method of pomegranate bark active component with strong antioxidant and staphylococcus aureus inhibiting activity |
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| US20140011241A1 (en) * | 2011-12-22 | 2014-01-09 | Christopher Charles Beatty | Method enabling isomerization process flows at lower pH, lower temperature, and in the presence of certain inhibiting compounds by using the xylose isomerase enzyme from the microorganism Fulvimarina pelagi |
| CN104080757A (en) * | 2011-12-22 | 2014-10-01 | 艾勒旺斯可再生科学公司 | Methods for suppressing isomerization of olefin metathesis products, methods of refining natural oils, and methods of producing fuel compositions |
| CN108250256A (en) * | 2018-03-05 | 2018-07-06 | 北京化工大学 | A kind of method for preparing high-purity punicalagins crystalline powder |
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| EP0949317A1 (en) * | 1998-03-31 | 1999-10-13 | Total Raffinage Distribution S.A. | Process and apparatus for the isomerisation of gasolines with high benzene content |
| US20140011241A1 (en) * | 2011-12-22 | 2014-01-09 | Christopher Charles Beatty | Method enabling isomerization process flows at lower pH, lower temperature, and in the presence of certain inhibiting compounds by using the xylose isomerase enzyme from the microorganism Fulvimarina pelagi |
| CN104080757A (en) * | 2011-12-22 | 2014-10-01 | 艾勒旺斯可再生科学公司 | Methods for suppressing isomerization of olefin metathesis products, methods of refining natural oils, and methods of producing fuel compositions |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110801460A (en) * | 2019-11-18 | 2020-02-18 | 中国科学院新疆理化技术研究所 | Preparation method of pomegranate bark active component with strong antioxidant and staphylococcus aureus inhibiting activity |
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