CN106526025A - Separation method for phenolic compounds in rubus corchorifolius - Google Patents
Separation method for phenolic compounds in rubus corchorifolius Download PDFInfo
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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
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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
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Abstract
A separation method for phenolic compounds in rubus corchorifolius comprises the following steps: 1) rubus corchorifolius samples are dissolved with a ketone solvent and mixed uniformly; 2) a filtrate is taken after filtering and is concentrated, and the filtrate is diluted with an organic acid; 3) the diluted filtrate is purified by a solid-phase extraction column, and an acidified alcohol solvent is added; 4) HPLC (high-performance liquid chromatography) is adopted for detection and separation of a sample mixture. In the separation method, the rubus corchorifolius pretreatment method is simple and effective; the separation method is implemented via HPLC, the process is easy to control, and the method is stable and reliable. Eight phenolics in the rubus corchorifolius can be obtained with the method, and powerful guidance is provided for detection of the phenolic compounds.
Description
Technical field
The present invention relates to field of natural medicinal chemistry, in particular to a kind of separation side of phenolic compound in raspberry
Method.
Background technology
Raspberry (scientific name：Rubus corchorifolius L.f.), also known as Rubus corchorifolius, mountain throw son, milk bubble, spread seedling bubble, three
Month bubble, April bubble, dragon-boat bubble, barley bubble, bubble youngster thorn, thorn cucurbit, steamed bun spinach, high pin ripple, upright shrub, high 1-3 rice；Branch tool skin
Thorn, is pubescence when young.Dan Ye, it is avette to ovum shape lanceolar, give birth in endroit, mountain valley, wasteland, small stream side and density shrubbery more
At humidity, at present not yet by artificial introducing and planting.The month at florescence 2-3, the fruiting period 4-6 month.With the supporing yang improving eyesight of puckery lean kidney, only sober up
Yearningly, the effect of resolving sputum is detoxified, cures mainly the disease such as kidney deficiency, seminal emission, drunk, erysipelas.Leaf slight bitter, removing toxic substances, detumescence, sore etc., throat
Swell and ache, the disease such as multiple abscess, mastitis.In addition to northeast, Gansu, Qinghai, Xinjiang, Tibet, Chinese remaining province, Korea, day
Sheet, Burma, Vietnam are distributed.
In raspberry contain eight kinds of aldehydes matters, respectively, i.e., anthocyanidin (cyanidin 3-sophoroside,
Cyaniding 3-glucoside and pelargonidin 3-glucoside), OPC (epicatechin and catechin),
Flavonols (quercetin 3-glucoside), ellagic acid and resveratrol.Above aldehydes matter has biologically active, has
Many effects such as antitumor, but determine its content and to carry out detached difficulty to which higher, there are no relevant report.
In view of this, it is special to propose the present invention.
The content of the invention
The first object of the present invention is the separation method for providing phenolic compound in a kind of raspberry, and methods described is by closing
Eight kinds of aldehydes matters in raspberry are finally separated by the pretreatment of reason and supporting subsequent treatment using HPLC.
In order to realize the above-mentioned purpose of the present invention, spy employs the following technical solutions：
One aspect of the present invention is related to a kind of separation method of classification compound in raspberry, and methods described includes following step
Suddenly：
1) raspberry sample is dissolved using ketones solvent and mix；
2) filtrate is taken after filtering, after concentration filtrate, organic acid dilute filtrate is used；
3) filtrate after dilution is purified using solid-phase extraction column, add alcohol-sour solvent；
4) detected using HPLC and separate sample mixture.
The present invention is by pre-processing raspberry sample so that the preferably dissolution of the aldehydes matter in sample is simultaneously stably deposited in
In solvent, aldehydes matter in raspberry is kept to stablize using acidifying alcohols solvent.Realize in sample eventually through the means of HPLC
The separation of each aldehydes matter.
Preferably, the step 1) in organic solvent be organic solvent of ketone, it is preferable that the ketones solvent is third
Ketone.
Preferably, it is described to mix specifically, in refiner stirring, wherein the rotating speed for stirring is 15000-20000rpm, stirring
The time is mixed for the 40-80 seconds.
Rotating speed is too fast can to make some aldehydes matter degraded losses, and pretreatment time is too short can not fully to extract phenolic material
Matter, it is long some aldehydes matters is easily aoxidized.
Preferably, the step 2) in filter under vacuum, filter residue use step 1) in organic solvent cleaning, receive
Collection cleaning fluid, it is preferable that cleaning is carried out 3-5 time.
Preferably, the step 2) in be concentrated in temperature 30-40 DEG C, pressure less than carrying out under conditions of 1MPa, preferably
Ground, stops when being concentrated into outlet yellow little particle.
Preferably, the step 2) in organic acid be diluted with water to volumn concentration for 2-5%, it is preferable that it is described
Organic acid is the organic acid containing 1-3 carbon atom, it is highly preferred that the organic acid is formic acid.
Preferably, the step 3) in alcohol-sour solvent in, alcohol is the alcohols containing 1-3 carbon atom, and acid is containing 1-
The organic acid of 3 carbon atoms, it is preferable that in the alcohol-sour solvent, the volumn concentration of acid is 2-5%.
Preferably, the step 3) used in solid-phase extraction column before purification, line activating is entered to solid-phase extraction column, it is preferable that
The detailed process of activation is to use the methyl alcohol equivalent to column capacity 1-2 times, the deionized water equivalent to column capacity 1-2 times successively
The solid-phase extraction column is processed with 3% aqueous formic acid equivalent to column capacity 1-2 times.
Preferably, the step 4) in HPLC carried out by the way of gradient elution, the mobile phase of the gradient elution
It is made up of methyl alcohol and heavy water, in elution process, percent by volume of the methyl alcohol in the mobile phase is within the 45-55 minutes by 15%
100% is incremented to progressively, it is preferable that the formic acid in the mobile phase also containing volume percentage 2-3%.
Preferably, the step 4) in the column temperature of HPLC be 38-42 DEG C, the flow velocity of mobile phase is 0.8-1.2ml/min.
Another aspect of the present invention is related to application of the methods described in other hollow certain kind of berries in the separation of phenolic compound.
Compared with prior art, beneficial effects of the present invention are：
(1), in separation method of the invention, the method for pre-processing raspberry sample is simple and effective；
(2) separation method of the invention is carried out by high performance liquid chromatography, and process is easily controllable, and method is reliable and stable；
(3) method of the present invention can obtain eight kinds of aldehydes matters in raspberry, be that the detection of phenolic compound is provided with
Power is instructed.
Specific embodiment
Embodiment of the present invention is described in detail below in conjunction with embodiment, but those skilled in the art will
Understand, the following example is merely to illustrate the present invention, and is not construed as limiting the scope of the present invention.It is unreceipted concrete in embodiment
Condition person, the condition advised according to normal condition or manufacturer are carried out.Agents useful for same or the unreceipted production firm person of instrument, are
The conventional products that commercially available purchase is obtained can be passed through.
Embodiment 1
Pre-process before following the steps below the separation of various phenolic compounds in raspberry
1) 3g raspberries sample is placed on refiner stirring used in the centrifuge tube of 50mL with 15mL acetone, stirs under 15000rpm
Mix 80 seconds, obtain the mixture of sample and acetone；
2) mixture obtained in and by step 1) is filtered under vacuo, and with 5mL acetone wash residuals thing 3 times, and by 3
Secondary filtered fluid merges, and wherein filter operation is carried out using funnel filter paper, also, one layer of mineral wool is covered on funnel filter paper；
3) using rotary condensation evaporimeter in 35 DEG C of evaporative filtration liquid, until the little particle for yellow occur stops evaporation；
4) sample of concentration is dissolved in 2% acetic acid of 5mL after evaporating, and by C18Sep-Pak posts, wherein,
C18Sep-Pak posts using front, successively using the methyl alcohol of 5ml, the deionized water of 6ml, 3% formic acid activation.；
5) anthocyanin and other phenolic compounds are brought back to life with the acidified methanol that 2mL contains 2% acetic acid and is reclaimed, it is all of
Recovery sample is filtered by 0.45 μm of syringe-driven filter, and the extract of 10 μ L of each sample is used for high-performance liquid chromatogram determination
Analysis；
6) using high performance liquid chromatograph respectively under wavelength 280nm, 365nm with 520nm while the different phenol generalizations of detection
Compound, obtains 8 different raspberry aldehydes matters, and is classified as 5 groups, i.e., anthocyanidin (cyanidin-3sophoroside,
Cyanidin-3glucoside and pelargonidin-3glucoside), OPC (epicatechin and catechin), flavones
Alcohol (quercetin-3glucoside), ellagic acid and resveratrol.
Embodiment 2
Pre-process before following the steps below the separation of various phenolic compounds in raspberry
1) 3g raspberries sample is placed on refiner stirring used in the centrifuge tube of 50mL with 15mL acetone, stirs under 17500rpm
Mix 1 minute, obtain the mixture of sample and acetone；
2) mixture obtained in and by step 1) is filtered under vacuo, and with 5mL acetone wash residuals thing 5 times, and by 5
Secondary filtered fluid merges, and wherein filter operation is carried out using funnel filter paper, also, one layer of mineral wool is covered on funnel filter paper；
3) using rotary condensation evaporimeter in 30 DEG C of evaporative filtration liquid, until the little particle for yellow occur stops evaporation；
4) sample of concentration is dissolved in 3% formic acid of 5mL after evaporating, and by C18Sep-Pak posts, wherein
C18Sep-Pak posts using front, successively using the methyl alcohol of 5ml, the deionized water of 6ml, 3% formic acid activation；
5) anthocyanin and other phenolic compounds are brought back to life with the acidified methanol that 2mL contains 3% formic acid and is reclaimed, it is all of
Recovery sample is filtered by 0.45 μm of syringe-driven filter, and the extract of 10 μ L of each sample is used for high-performance liquid chromatogram determination
Analysis；
6) using high performance liquid chromatograph respectively under wavelength 280nm, 365nm with 520nm while the different phenol generalizations of detection
Compound, obtains 8 different raspberry aldehydes matters, and is classified as 5 groups, i.e., anthocyanidin (cyanidin 3-sophoroside,
Cyaniding 3-glucoside and pelargonidin 3-glucoside), OPC (epicatechin and catechin),
Flavonols (quercetin 3-glucoside), ellagic acid and resveratrol.
Embodiment 3
Pre-process before following the steps below the separation of various phenolic compounds in raspberry
1) 3g raspberries sample is placed on refiner stirring used in the centrifuge tube of 50mL with 15mL acetone, stirs under 20000rpm
Mix 40 seconds, obtain the mixture of sample and acetone；
2) and by the mixture obtained in step (1) filter under vacuo, and with 5mL acetone wash residuals thing 3 times, and general
3 times filtered fluid merges；
3) using rotary condensation evaporimeter in 40 DEG C of evaporative filtration liquid, until the little particle for yellow occur stops evaporation；
4) sample of concentration is dissolved in 5% formic acid of 5mL after evaporating, and passes through C18Sep-Pak posts；
5) anthocyanin and other phenolic compounds are brought back to life with the acidified methanol that 2mL contains 5% formic acid and is reclaimed, it is all of
Recovery sample is filtered by 0.45 μm of syringe-driven filter, and the extract of 10 μ L of each sample is used for high-performance liquid chromatogram determination
Analysis；
6) using high performance liquid chromatograph respectively under wavelength 280nm, 365nm with 520nm while the different phenol generalizations of detection
Compound, obtains 8 different raspberry aldehydes matters, and is classified as 5 groups, i.e., anthocyanidin (cyanidin-3sophoroside,
Cyanidin-3glucoside and pelargonidin-3glucoside), OPC (epicatechin and catechin), flavones
Alcohol (quercetin-3glucoside), ellagic acid and resveratrol.
Comparative example 1
Pre-process before following the steps below the separation of various phenolic compounds in raspberry
1) 3g raspberries sample is placed on refiner stirring used in the centrifuge tube of 50mL with 15mL acetone, stirs under 17500rpm
Mix 1 minute, obtain the mixture of sample and acetone；
2) mixture obtained in and by step 1) is filtered under vacuo, and with 5mL acetone wash residuals thing 5 times, and by 5
Secondary filtered fluid merges, and wherein filter operation is carried out using funnel filter paper, also, one layer of mineral wool is covered on funnel filter paper；
3) using rotary condensation evaporimeter in 30 DEG C of evaporative filtration liquid, until the little particle for yellow occur stops evaporation；
4) sample of concentration is dissolved in 3% formic acid of 5mL after evaporating, and passes through C18Sep-Pak posts；
5) anthocyanin and other phenolic compounds are brought back to life with the acidified methanol that 2mL contains 3% formic acid and is reclaimed, it is all of
Recovery sample is filtered by 0.45 μm of syringe-driven filter, and the extract of 10 μ L of each sample is used for high-performance liquid chromatogram determination
Analysis；
6) using high performance liquid chromatograph respectively under wavelength 280nm, 365nm with 520nm while the different phenol generalizations of detection
Compound, obtains 8 different raspberry aldehydes matters, and is classified as 5 groups, i.e., anthocyanidin (cyanidin-3sophoroside,
Cyanidin-3glucoside and pelargonidin-3glucoside), OPC (epicatechin and catechin), flavones
Alcohol (quercetin-3glucoside), ellagic acid and resveratrol.
Comparative example 2
Pre-process before following the steps below the separation of various phenolic compounds in raspberry
1) 3g raspberries sample is placed on refiner stirring used in the centrifuge tube of 50mL with 15mL acetone, stirs under 17500rpm
Mix 1 minute, obtain the mixture of sample and acetone；
2) using rotary condensation evaporimeter in 30 DEG C of evaporative filtration liquid, until the little particle for yellow occur stops evaporation；
3) sample of concentration is dissolved in 3% formic acid of 5mL after evaporating, and by C18Sep-Pak posts, wherein
C18Sep-Pak posts using front, successively using the methyl alcohol of 5ml, the deionized water of 6ml, 3% formic acid activation；
4) sample is filtered by 0.45 μm of syringe-driven filter, and the extract of 10 μ L of each sample is used for high performance liquid chromatography
Determine analysis；
5) using high performance liquid chromatograph respectively under wavelength 280nm, 365nm with 520nm while the different phenol generalizations of detection
Compound, obtains 8 different raspberry aldehydes matters, and is classified as 5 groups, i.e., anthocyanidin (cyanidin-3sophoroside,
Cyanidin-3glucoside and pelargonidin-3glucoside), OPC (epicatechin and catechin), flavones
Alcohol (quercetin-3glucoside), ellagic acid and resveratrol.
Experimental example
HPLC is carried out with pretreated sample in comparative example 1,2 to embodiment 1-3 to separate, the laboratory apparatus for using is such as
Under：
Pillar：Polaris C-18A, 5u, 300X 4,6mm,
Guard column：MetaGuard 4,6mm Polaris C18-A, 5u,
Detector device：PDA (two pole official's array detector of photoelectricity)
Detection wavelength：200-750nm (254,320,365,503 and 519nm)
The condition of HPLC is as follows：
Embodiment 1：
Mobile phase
Flow velocity：1.2ml/min
Run time：45min
Equilibration time：15min
Wash-out type：Gradient
Solvent：A：2% water -2D- formic acid, B:2% methyl alcohol-formic acid
Elution requirement：
Efficient liquid phase good separating effect, the difference of each component retention time are larger, intersect few between the peak of each component.
Embodiment 2：
Mobile phase
Flow velocity：1ml/min
Run time：52min
Equilibration time：15min
Wash-out type：Gradient
Solvent：A：2.45% water -2D- formic acid, B:2.45% methyl alcohol-formic acid
Elution requirement：
Efficient liquid phase good separating effect, the difference of each component retention time are larger, intersect few between the peak of each component.
Embodiment 3：
Mobile phase
Flow velocity：1.2ml/min
Run time：55min
Equilibration time：15min
Wash-out type：Gradient
Solvent：A：Water -2D, B:Methyl alcohol
Elution requirement：
Efficient liquid phase good separating effect, the difference of each component retention time are larger, intersect few between the peak of each component.
Comparative example 1,2：
Mobile phase
Flow velocity：1ml/min
Run time：52min
Equilibration time：15min
Wash-out type：Gradient
Solvent：A：2.45% water -2D- formic acid, B:2.45% methyl alcohol-formic acid
Elution requirement：
Efficient liquid phase separating effect is general, and the difference of each component retention time is little, has intersection between the peak of each component.
Wherein, the HPLC results in embodiment 3 are as shown in table 1 below, and the HPLC results in comparative example 1 are as shown in table 2 below, right
HPLC results in ratio 2 are as shown in table 3 below.
Table 1
| Product result | Λmax(nm) | Retention time (min) |
| Anthocyanidin 3- sophoroside | 520 | 17.2 |
| Anthocyanidin 3- glucosides | 520 | 18.6 |
| - 3 glucoside of pelargonidin | 520 | 20.7 |
| Epicatechin | 365 | 21.6 |
| Catechin | 365 | 22.8 |
| Quercetin 3- glucosides | 365 | 28.1 |
| Ellagic acid | 365 | 29.5 |
| Resveratrol | 280 | 31.1 |
Table 2
Table 3
| Product result | Λmax(nm) | Retention time (min) |
| Anthocyanidin 3- sophoroside | 520 | 20.1 |
| Anthocyanidin 3- glucosides | 520 | 20.6 |
| - 3 glucoside of pelargonidin | 520 | 20.7 |
| Epicatechin | 365 | 22.6 |
| Catechin | 365 | 22.6 |
| Quercetin 3- glucosides | 365 | 28.5 |
| Ellagic acid | 365 | 28.8 |
| Resveratrol | 280 | 28.8 |
Can be seen that by the data in above table and processed after sample using the method in comparative example, cannot in HPLC
Phenols in sample is kept completely separate, it can be seen that the retention time of many phenols is overlapped or closely, it is impossible to effectively point
From.
Although with specific embodiment illustrate and describing the present invention, but it will be appreciated that without departing substantially from the present invention's
Many other changes and modification can be made in the case of spirit and scope.It is, therefore, intended that in the following claims
Including all such changes and modifications belonged in the scope of the invention.
Claims (10)
1. in a kind of raspberry phenolic compound separation method, it is characterised in that the method comprising the steps of：
1) raspberry sample is dissolved using ketones solvent and mix；
2) filtrate is taken after filtering, after concentration filtrate, organic acid dilute filtrate is used；
3) filtrate after dilution is purified using solid-phase extraction column, add the alcohols solvent of acidifying；
4) detected using HPLC and separate sample mixture.
2. method according to claim 1, it is characterised in that the step 1) in ketones solvent be acetone.
3. method according to claim 1, it is characterised in that the mixing specifically, stir in refiner, wherein stirring
Rotating speed be 15000-20000rpm, mixing time be the 40-80 seconds.
4. method according to claim 1, it is characterised in that the step 2) in filter under vacuum, filter residue makes
With step 1) in organic solvent clean, collect cleaning fluid, it is preferable that cleaning carry out 3-5 time.
5. method according to claim 1, it is characterised in that the step 2) in be concentrated in temperature 30-40 DEG C, pressure
Carry out less than under conditions of 1MPa, it is preferable that be concentrated into when there is yellow little particle and stop.
6. method according to claim 1, it is characterised in that the step 2) in organic acid for volumn concentration be
The aqueous solution of 2-5%, it is preferable that the organic acid is the organic acid containing 1-3 carbon atom, it is highly preferred that the organic acid
It is formic acid.
7. method according to claim 1, it is characterised in that the step 3) described in acidifying alcohols solvent, alcohol
It is the alcohols containing 1-3 carbon atom, acid is the organic acid containing 1-3 carbon atom, it is preferable that the alcohols solvent of the acidifying
In, the volumn concentration of acid is 2-5%.
8. method according to claim 1, it is characterised in that the step 3) used in solid-phase extraction column before purification, it is right
Solid-phase extraction column enters line activating, it is preferable that the detailed process of activation is, successively using methyl alcohol, deionized water and aqueous formic acid
The solid-phase extraction column is processed；It is highly preferred that using the methyl alcohol equivalent to column capacity 1-2 times successively, holding equivalent to post
The deionized water of 1-2 times of amount and 3% aqueous formic acid equivalent to column capacity 1-2 times process the solid-phase extraction column.
9. method according to claim 1, it is characterised in that the step 4) in HPLC by the way of gradient elution
Carry out, the mobile phase of the gradient elution is made up of methyl alcohol and heavy water, in elution process, volume of the methyl alcohol in the mobile phase
Percentage is progressively incremented to 100% by 15% within 45-55 minutes, it is preferable that also contain percent by volume in the mobile phase
The formic acid of meter 2-3%, it is preferable that the step 4) in the column temperature of HPLC be 38-42 DEG C, the flow velocity of mobile phase is 0.8-1.2ml/
min。
10. application of the method in claim 1-9 described in any one in other hollow certain kind of berries in the separation of phenolic compound.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112129851A (en) * | 2020-08-23 | 2020-12-25 | 浙江省农业科学院 | Establishment method of raspberry polyphenol fingerprint spectrum |
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| CN112129851A (en) * | 2020-08-23 | 2020-12-25 | 浙江省农业科学院 | Establishment method of raspberry polyphenol fingerprint spectrum |
| CN112129851B (en) * | 2020-08-23 | 2022-09-09 | 浙江省农业科学院 | Establishment method of raspberry polyphenol fingerprint spectrum |
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Application publication date: 20170322 |