CN103265519B - The method of Folium Myricae rubrae proanthocyanidin is prepared in a kind of separation - Google Patents
The method of Folium Myricae rubrae proanthocyanidin is prepared in a kind of separation Download PDFInfo
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Abstract
The invention discloses a kind of method that Folium Myricae rubrae proanthocyanidin is prepared in separation, comprising: Folium Myricae rubrae powder is added in solvent and carries out lixiviate, be separated and obtain extractive substance; By column chromatography, separation and purification is carried out to extractive substance, obtain proanthocyanidins material; Liquid chromatography is utilized to be separated by molecular size range proanthocyanidins material; Wherein, the moving phase of described liquid chromatography is made up of mobile phase A and Mobile phase B, and type of elution is gradient elution; Mobile phase A be normal hexane, methyl alcohol, ethyl acetate by volume 8-11:2-4:1 mix, Mobile phase B be normal hexane, methyl alcohol, ethyl acetate by volume 1-2:2-4:1 mix.The inventive method can be used for separation, the preparation of different molecular weight proanthocyanidin in different plant leaf, and avoid in preparation process using chloride organic reagent, can reduce environmental pollution as far as possible, products therefrom may be used for research different molecular weight to the impact of proanthocyanidin function.
Description
Technical field
The present invention relates to plant function component field, particularly relate to a kind of method that Folium Myricae rubrae proanthocyanidin is prepared in separation.
Background technology
Red bayberry is the local product fruits of south China, at present about the research and utilization of red bayberry is mainly based on Waxberry fruit.Hairy Waxmyrtle is evergreen all the year round, flourishing, has every year and is often taken as waste by the Folium Myricae rubrae pruned in a large number and abandons.There are some researches show in Folium Myricae rubrae and be rich in aldehydes matter, having the biological activitys such as anti-oxidant, anti-bacteria and anti-virus, is a kind of plant resources with potentiality to be exploited.Therefore, if by these wastes in addition Appropriate application, processing raw material of " cheapness " can be become, not only meets the themes of the times of " low-carbon (LC), green, environmental protection ", more while promotion comprehensive utilization of resources, considerable economic benefit can be brought.
Proanthocyanidin is extensively present in one of botanic polyphenols.The experimental results shows that it has the active function of anti-oxidant, anticancer, prevention and therapy cardiovascular disorder, antianaphylaxis and anti-inflammatory, radioprotective, skin care and crease-resistant etc. useful human health, and these functions and its structure form closely related.The proanthocyanidin of same molecular amount in separation and Extraction Folium Myricae rubrae, study the impact of different molecular weight for proanthocyanidin function, contribute to the further understanding to relation between proanthocyanidin active function and molecular weight, for the practical application of proanthocyanidin provides theoretical foundation.The plant proanthocyanidin of current research is maximum with pycnogenols class, and typical example is as grape pip procyanidin.Develop more abundanter proanthocyanidin natural resource, as Folium Myricae rubrae proanthocyanidin, there is wide application and development prospect.
Proanthocyanidin belongs to plant-sourced flavonoid, and except participating in astringent taste in food quality, bitter taste, fragrance and color are formed, and also have a lot of wholesome effect.Proanthocyanidin can be divided into monomer proanthocyanidin, oligomeric proanthocyanidins and height gather proanthocyanidin according to the proanthocyanidin polymerization degree (i.e. the number of component units).Monomer proanthocyanidin comprises flavane-3, 4-glycol and flavane-4-alcohol etc., oligomeric proanthocyanidins refers generally to the proanthocyanidin that the polymerization degree is 2-5, high poly-proanthocyanidin refers generally to the proanthocyanidin of the polymerization degree >=6, oligomeric proanthocyanidins and height to gather between proanthocyanidin not obvious boundary ((a) Rasmussen, S.E., Frederiksen, H., Struntze Krogholm, K., & Poulsen, L. (2005) .Dietary proanthocyanidins:occurrence, dietary intake, bioavailability, and protection against cardiovascular disease.Molecular Nutrition & Food Research, 49 (2), 159-174. (b) Quideau, S., Deffieux, D., Douat-Casassus, C., & Pouysegu, L. (2011) .Plant polyphenols:chemical properties, biological activities, and synthesis.Angew Chem Int Ed Engl, 50 (3), 586-621.).
Because the complicacy of the diversity of proanthocyanidin and structure, analyzing and describe the structure of proanthocyanidin is a difficult task.When molecular weight exceedes tetramer, the possible quantity of structure and steric isomer becomes a lot, and in addition, when gallic acid unit also exists, its separation becomes more difficult.The biological activity of proanthocyanidin is closely related with its polymerization degree, in the market, only has the standard substance of a small amount of procyanidin dimers can supply to buy, and expensive, seriously limits the research and development of proanthocyanidin.
At present in the normal-phase chromatography of proanthocyanidin is separated, usual employing be methylene chloride/methanol/acetic acid/water system (Liu, Y.X., Pan, Q.H., Yan, G.L., He, J.J., & Duan, C.Q. (2010) .Changes of Flavan-3-ols with Different Degrees of Polymerization in Seeds of ' Shiraz ', ' Cabernet Sauvignon ' and ' Marselan ' Grapes after Veraison.Molecules, 15 (11), 7763-7774.), but, strong acid and the stronger chlorinated solvents of toxicity is applied in this system, and the large-scale separation being not suitable for proanthocyanidin is standby.
Summary of the invention
The invention provides a kind of method that Folium Myricae rubrae proanthocyanidin is prepared in separation, for proanthocyanidin oligomer that is quick, that accurately obtain certain molecular weight in a large amount of Folium Myricae rubrae, reagent toxicity is little, security is higher.
A method for Folium Myricae rubrae proanthocyanidin is prepared in separation, comprising:
(1) Folium Myricae rubrae powder is added in solvent carry out lixiviate, be separated and obtain extractive substance;
(2) by column chromatography, separation and purification is carried out to extractive substance, obtain proanthocyanidins material;
(3) liquid chromatography is utilized to be separated by molecular size range proanthocyanidins material;
Wherein, the moving phase of described liquid chromatography is made up of mobile phase A and Mobile phase B, and type of elution is gradient elution;
Mobile phase A be normal hexane, methyl alcohol, ethyl acetate by volume 8-11:2-4:1 mix, Mobile phase B be normal hexane, methyl alcohol, ethyl acetate by volume 1-2:2-4:1 mix;
Condition of gradient elution is: 0-90min, and the volume percent of Mobile phase B in moving phase is 0-20%; 90-130min, the volume percent of Mobile phase B in moving phase is 80-100% by 0-20% linear change; 130-150min, the volume percent of Mobile phase B in moving phase keeps 80-100%.
Be rich in proanthocyanidins material in Folium Myricae rubrae, but proanthocyanidin kind is more, the proanthocyanidin function difference of different molecular weight is larger.With the extractive substance of Folium Myricae rubrae for raw material, by suitable column chromatography and liquid chromatography separating treatment, the proanthocyanidin oligomer of certain molecular weight can be obtained.
In step (1), described Folium Myricae rubrae powder can be prepared by the following method: cleaned by Folium Myricae rubrae, dries or pulverize after 40-45 DEG C of forced air drying or vacuum-drying 12-24h to obtain under the sun.
The particle diameter of described Folium Myricae rubrae powder is preferably 40-60 order.
Described solvent can be aqueous acetone solution.
The concentration of volume percent of described aqueous acetone solution is preferably 60-80%; Be more preferably 70%.The aqueous acetone solution of this concentration range is conducive to the leaching of Folium Myricae rubrae Procyanidins material most.
Described Folium Myricae rubrae powder and the weight ratio of aqueous acetone solution are preferably 1:6-1:10, are more preferably 1:8.
In order to slow down the deterioration by oxidation of leaching process Procyanidins, improving extracting effect, preferably, in described aqueous acetone solution, being added with the xitix that mass percent concentration is 0.01-1%.
Described extraction temperature is 15-35 DEG C, and extraction time is 4-12h, and under this condition, extracting effect is best.
Obtaining proanthocyanidin to fully extract from Folium Myricae rubrae, with aqueous acetone solution lixiviate 1-3 time, each vat liquor after lixiviate, can be merged.
In step (2), described column chromatography is gel permeation chromatography, and eluent used is aqueous acetone solution or methanol aqueous solution.Gel permeation chromatography can adopt Sephadex LH-20 chromatography column, can realize the rough separation of Folium Myricae rubrae proanthocyanidin.
Adopt different eluent to carry out wash-out, can obtain different cuts, cut Procyanidins content can be detected by vanillin-sulfuric acid method.
In order to obtain the higher cut of proanthocyanidin content so that follow-up refining processing, described eluent can be aqueous acetone solution.
Preferably, the aqueous acetone solution of described eluent to be concentration of volume percent be 45-55%, is preferably 50%.Test-results shows, adopts the aqueous acetone solution of this concentration as eluent, and the cut Procyanidins content of wash-out gained can arrive 50-60%.
In step (3), described liquid chromatography is positive preparative chromatography.
Due to methyl alcohol and normal hexane mutual solubility poor, ethyl acetate can make both dissolve each other preferably, adopts normal hexane/methanol/ethyl acetate solvent system to be also divided into mobile phase A and Mobile phase B, can carry out gradient elution operation better, and elute effect is better.
Preferably, mobile phase A be normal hexane, methyl alcohol, ethyl acetate by volume 10:3:1 mix, Mobile phase B be normal hexane, methyl alcohol, ethyl acetate by volume 1:3:1 mix;
Condition of gradient elution is: 0-90min, and the volume percent of Mobile phase B in moving phase is 16.4%; 90-130min, the volume percent of Mobile phase B in moving phase is 80% by 16.4% linear change; 130-150min, the volume percent of Mobile phase B in moving phase keeps 80%.
The determined wavelength of described liquid chromatography is 280nm, and column temperature is 30-40 DEG C, and the flow velocity of moving phase is 18-25mL/min; Preferably, column temperature is 37 DEG C, and the flow velocity of moving phase is 21.6mL/min.
Connexus spectrum analysis, collects effluent liquid respectively at different appearance time when liquid chromatography is separated, can obtain the proanthocyanidin that a large amount of molecular weight is close.May be there are several isomerss in the proanthocyanidin of same molecular amount, adopt the method can obtain the close material of molecular weight, but differ and be decided to be pure substance.
The proanthocyanidin that molecular weight is respectively 578-762,866-914,1034-1066,1155-1219,1323-1370,1443-1523,1627-1675 and 1731-1826 can be obtained after separation.Test-results shows, the molecular weight that can obtain essential substance after separation is respectively the proanthocyanidin of 762,914,1066,1218,1370,1523,1675 and 1826.
This liquid phase chromatography can refine the proanthocyanidin material obtaining and have target molecular weight.In preparation process, moving phase used is normal hexane/methanol/ethyl acetate solvent system, do not adopt this class toxicity of methylene dichloride being usually used at present being separated proanthocyanidin large and the chloro-carbon solvent of contaminate environment, can reduce the pollution to environment, security is higher; And by gradient elution, can quickly and accurately the proanthocyanidins material of several molecular weight effectively be separated.
The present invention take Folium Myricae rubrae as raw material, adopts aqueous acetone solution to carry out lixiviate; Then utilize suitable eluent to carry out column chromatography for separation, obtain the cut that proanthocyanidin content is higher; Afterwards, using normal hexane/methanol/ethyl acetate solvent system as moving phase, carry out liquid chromatography separation, prepare the proanthocyanidin that a large amount of molecular weight is close.
Adopt the inventive method, there is following beneficial effect:
(1) can be used for separation, the preparation of different molecular weight proanthocyanidin in different plant leaf.
(2) avoid in preparation process using chloride organic reagent, environmental pollution can be reduced as far as possible.
(3) products therefrom may be used for research different molecular weight to the impact of proanthocyanidin function.
Accompanying drawing explanation
Fig. 1 is positive preparative separation color atlas in embodiment 1.
Embodiment
Embodiment 1
From Folium Myricae rubrae, be separated the proanthocyanidin preparing different molecular weight, carry out following steps successively:
(1) Folium Myricae rubrae (water chestnut kind) is cleaned, remove disease and pest blade, pulverize after 40 DEG C of vacuum-dryings, cross 40 mesh sieves.
(2) abstraction process: get 4kg Folium Myricae rubrae powder, be placed in 32L70%(v/v) aqueous acetone solution (being added with the xitix that mass percent concentration is 0.5%), lixiviate 4h under room temperature (25 DEG C), lixiviate three times; Collect merging three vat liquors, 40 DEG C of rotary evaporation removing acetone, filtered while hot, obtains the about 30L aqueous solution and lyophilize, obtains about 400g extractive substance, i.e. Folium Myricae rubrae proanthocyanidin crude extract EPAs.
(3) rough operation: get 5g extractive substance, is dissolved in methanol-water (1:1, v/v), is splined on Sephadex LH-20 chromatography column (300 × 25mm).Adopt the methanol aqueous solution of different concns, aqueous acetone solution as eluent successively, elution program, in table 1, collects four cuts called after cut 1, cut 2, cut 3 and the cut 4 respectively obtained.
Adopt vanillin-sulfuric acid method to detect each cut Procyanidins content, draw, in the cut (cut 3) obtained with the aqueous acetone solution wash-out of 50% concentration, proanthocyanidin content is between 50-60%, and content is the highest.For this reason, the cut (cut 3) that obtains of aqueous acetone solution wash-out that concentration of volume percent is 50% is chosen.Elutriant, through rotary evaporation removing organic solvent postlyophilization, obtains proanthocyanidins material.
Table 1Sephadex LH-20 chromatography column is separated the program of EPAs
(4) Folium Myricae rubrae proanthocyanidin component molecules amount measure of spread: using proanthocyanidins material as raw material, with normal hexane/methanol/ethyl acetate for solvent system, adopt positive facies analysis chromatograph-mass spectrometer coupling technology to carry out isolation identification, obtain the distributed data of Folium Myricae rubrae proanthocyanidin molecular weight.
Be specially: positive analytical chromatograph is Agilent1100Series, detector is UV detector, and determined wavelength is 280nm, and chromatographic column model is Luna Silica(250 × 4.6mm, 5 μm, Phenomenex Inc., Torrance, CA, USA), flow velocity is 1mL/min, and column temperature is 37 DEG C; Moving phase is made up of mobile phase A and Mobile phase B, and mobile phase A is that normal hexane/methanol/ethyl acetate obtains according to the volume mixture of 10:3:1, and Mobile phase B is that normal hexane/methanol/ethyl acetate obtains according to the volume mixture of 1:3:1;
Gradient elution method is as follows:
0-90min, the volume percent of Mobile phase B in moving phase is 16.4%;
90-130min, the volume percent of Mobile phase B in moving phase is 80% by 16.4% linear change;
130-150min, the volume percent of Mobile phase B in moving phase keeps 80%;
(5) refining step: be amplified in positive preparative chromatography by positive facies analysis chromatogram, Fractional Collections Folium Myricae rubrae proanthocyanidin, obtains the part of a large amount of same molecular amount Folium Myricae rubrae proanthocyanidin.
Be specially: positive preparative chromatograph is Shimadzu LC-8A type, chromatographic column model is Luna Silica(250 × 21.2mm, 5 μm, Phenomenex Inc., Torrance, CA, USA), flow velocity is 21.6mL/min, and all the other conditions are identical with positive analysis condition.Color atlas as shown in Figure 1.
According to Fig. 1 known each peak time of occurrence: 26-31.4min, 35-41min, 45-50min, 59-66min, 76-82min, 96-103min, 105-110min, 110-120min, by this time period Fractional Collections Folium Myricae rubrae proanthocyanidin, can obtain the Folium Myricae rubrae proanthocyanidin that a large amount of molecular weight is close.According to molecular weight determination, in Fig. 1, the molecular weight of No. 1 essential substance is 762, corresponding (E) GC-(E) GCG, the molecular weight of No. 2 essential substance is 914, corresponding 2 (E) GCG or 3 (E) GC, the molecular weight of No. 3 essential substance is 1066, corresponding 2 (E) GC-(E) GCG, the molecular weight of No. 4 essential substance is 1218, corresponding (E) GC-2 (E) GCG or 4 (E) GC, the molecular weight of No. 5 essential substance is 1370, corresponding 3 (E) GCG or 3 (E) GC-(E) GCG, the molecular weight of No. 6 essential substance is 1523, corresponding 5 (E) GC, or 2 (E) GC-2 (E) GCG, the molecular weight of No. 7 essential substance is 1675, corresponding (E) GC-3GCG or 4 (E) GC-(E) GCG, the molecular weight of No. 8 essential substance is 1826, corresponding 3 (E) GC-2 (E) GCG, 4 (E) GCG, or 3 (E) CG-(E) GCG.Wherein, (E) GC is (table) Cg, and (E) CG is (table) catechin and gallate, and (E) GCG is (table) nutgall catechin gallic acid ester.
Test-results show the present embodiment method can realize the close Folium Myricae rubrae proanthocyanidin of molecular weight quick, accurately prepare, and reagent toxicity is little, security is higher.
Claims (6)
1. a method for Folium Myricae rubrae proanthocyanidin is prepared in separation, comprising:
(1) Folium Myricae rubrae powder is added in solvent carry out lixiviate, be separated and obtain extractive substance;
(2) with concentration of volume percent be the aqueous acetone solution of 45-55% as eluent, by gel permeation chromatography, separation and purification is carried out to extractive substance, obtains proanthocyanidins material;
(3) liquid chromatography is utilized to be separated by molecular size range proanthocyanidins material;
Wherein, the moving phase of described liquid chromatography is made up of mobile phase A and Mobile phase B, and type of elution is gradient elution;
Described mobile phase A be normal hexane, methyl alcohol, ethyl acetate by volume 10:3:1 mix, Mobile phase B be normal hexane, methyl alcohol, ethyl acetate by volume 1:3:1 mix;
Condition of gradient elution is: 0-90min, and the volume percent of Mobile phase B in moving phase is 16.4%; 90-130min, the volume percent of Mobile phase B in moving phase is 80% by 16.4% linear change; 130-150min, the volume percent of Mobile phase B in moving phase keeps 80%;
In step (3), after separation, obtain the proanthocyanidin that molecular weight is respectively 578-762,866-914,1034-1066,1155-1219,1323-1370,1443-1523,1627-1675 and 1731-1826.
2. method according to claim 1, is characterized in that: in step (1), and described solvent is aqueous acetone solution.
3. method according to claim 2, is characterized in that: in step (1), and the concentration of volume percent of described aqueous acetone solution is 60-80%.
4. method according to claim 3, is characterized in that: described Folium Myricae rubrae powder and the weight ratio of aqueous acetone solution are 1:6-1:10.
5. method according to claim 2, is characterized in that: in step (1), is added with the xitix that mass percent concentration is 0.01-1% in described aqueous acetone solution.
6. method according to claim 1, is characterized in that: in step (1), and described extraction temperature is 15-35 DEG C, and extraction time is 4-12h.
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WO2022241749A1 (en) * | 2021-05-21 | 2022-11-24 | 浙江大学 | Method for chemical synthesis of prodelphinidin b9 gallate |
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