CN102796154A - Method for separating and preparing high-purity acylated delphinidin derivatives from eggplant peel - Google Patents
Method for separating and preparing high-purity acylated delphinidin derivatives from eggplant peel Download PDFInfo
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Abstract
The invention relates to a method for separating and preparing 3-[4-p-coumaroyl-L-rhamnosyl-(1-2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin from eggplant peel, which comprises the following steps: peeling the raw material eggplants, concentrating by extraction, removing impurities, purifying with macroporous resin, purifying with a gel, and combining a semipreparative chromatograph to obtain the 3-[4-p-coumaroyl-L-rhamnosyl-(1-2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin. The method is simple to operate, can effectively separate high-purity anthocyanin monomer from eggplant peel, and can implement large-scale preparation; and the purity of the prepared 3-[4-p-coumaroyl-L-rhamnosyl-(1-2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin is higher than 99.79%.
Description
Technical field
The present invention relates to a kind of preparation method of delphinidin verivate, be specifically related to a kind of method for preparing high purity 3-[4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin of from the eggplant skin, separating.
Background technology
Anthocyanogen (Anthocyanidin) is a kind of natural water colo(u)r, is widespread in nature, and belongs to flavonoids.Anthocyanogen is by anthocyanogen aglycon and the polyphenols of sugar through the glycosidic link be combined into, and on glycosyl or hydroxyl, can also form the anthocyanogen of acylations with organic acid through ester bond.Research shows that anthocyanogen has multiple physiologically active to the human body beneficial, like chronic diseases such as anti-oxidant activity, anti-inflammatory and Prevention of Cardiovascular.Therefore can be used as natural pigment, natural antioxidants and functional food and add factor application.
Eggplant is a kind of common vegetables, and is main as edible.In eggplant, be rich in abundant anthocyanogen in its purple or the black kind skin.The kind of anthocyanogen mainly contains 3-[L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin of on-acylated and acidylate in the different eggplant kinds of reporting at present.The anthocyanogen of acidylate wherein, promptly [4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin is more stable relatively for 3-, and content is abundant in the eggplant skin, and its molecular structure is as follows.
To the extraction of anthocyanogen bullion the most frequently used be solvent-extraction process, common solvent has methyl alcohol, ethanol, acetone etc.For the purifying of anthocyanin class material commonly used be macroreticular resin absorbing method, its efficient is high, and is simple to operate, is fit to mass preparation.
The high purity anthocyanogen not only has wide application potential at food, medicine, cosmetic field, and for the further investigation of aspects such as the colour stability of single anthocyanogen and physiological function very significant values is arranged.Now commercially available anthocyanogen mark article kind is few, and costs an arm and a leg.Especially acylations anthocyanogen standard substance are few.Therefore be that the highly purified acylations anthocyanogen monomer of raw material separation preparation has significant meaning with the eggplant skin.
Summary of the invention
The object of the present invention is to provide a kind of method for preparing 3-[4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin of from the eggplant skin, separating; Said method is raw material with the eggplant; Through it is peeled; Lixiviate concentrates, the step of removal of impurities, macroporous resin purification, gel-purified, combination half preparative hplc, obtains 3-[4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin.This method is simple to operate, can effectively from the eggplant skin, separate to obtain highly purified anthocyanogen monomer, and can realize mass preparation.
For realizing above-mentioned purpose, the present invention adopts following scheme:
A kind of method for preparing 3-[4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin of from the eggplant skin, separating may further comprise the steps:
(1) raw materials pretreatment: with fresh eggplant clean, peeling, and the eggplant skin shredded;
(2) the eggplant pericarp anthocyanin is slightly carried liquid concentrator: with the eggplant skin that obtains, according to solid-liquid ratio 1: 2 (w/v, ratio g/mL) adds in 0.01% methanol hydrochloride solution (v/v); Under the normal temperature, lixiviate is filtered; Three times repeatedly, merging filtrate is removed methyl alcohol at 40-45 ℃ of following rotary evaporation in vacuo and is obtained the anthocyanogen crude extract then; In said crude extract: the volume ratio of ETHYLE ACETATE is that 1: 2 ratio adds ethyl acetate extraction, and standing demix extracts three times; Collect the merging water, rotate abundant evaporative removal ETHYLE ACETATE, obtain anthocyanogen medicinal extract in 40-50 ℃ of following vacuum; Medicinal extract with the dissolving of a spot of 0.01% (v/v) aqueous solution of hydrochloric acid, is obtained the anthocyanogen sample solution;
(3) macroporous resin adsorption: macroporous adsorbent resin is packed in the chromatography column
, wash with 0.01% (v/v) aqueous solution of hydrochloric acid; With the flow velocity injection macroporous resin column of anthocyanogen sample solution with 0.5BV/h; Earlier wash resin with 1BV/h with the deionized water that contains 0.01% hydrochloric acid (v/v); Use 0.01% methanol hydrochloride solution (v/v) the anthocyanogen composition to be resolved from resin again with the flow velocity of 1BV/h; The desorbed solution that obtains is removed methyl alcohol at 40-45 ℃ of following rotary evaporation in vacuo, obtain the anthocyanogen bullion;
(4) gel-purified: will inject gel column from the anthocyanogen bullion that macroporous resin purification obtains
Methanol-water with 50% (v/v) wash-out accesses once according to per 15 minutes, collects elutriant, with the elutriant of collecting, removes methyl alcohol at 40-45 ℃ of following rotary evaporation in vacuo, obtains the anthocyanogen extract of preliminary purification; Said macroporous adsorbent resin is that (specific surface area is 500m to XAD-7HP
2/ g; Mean pore size does
Median size is 560 μ m; Dipole moment is 1.8; Coefficient of uniformity D90/D40 is 1.7); Said gel column is Sephadex LH-20 (separating ranges 100-4000; Particle size is 20-150 μ m);
(5) monomer preparation: utilize half preparative hplc to separate the anthocyanogen monomer, anthocyanogen that will purifying obtains from gel column is extracted appearance, separates service routine 1 preparation separation with half preparative hplc; Moving phase among the said program l is respectively the A phase: 0.5% formic acid pure water, B phase: the methyl alcohol of 0.5% formic acid, chromatographically pure, V/V; The condition of gradient elution (v/v) that adopts: 0-3min:40%B phase; The 3-10min:40%-50%B phase; The 10-12min:50%-70%B phase; The 12-15min:70%B phase; The 15-17min:70%-30%B phase; Flow velocity 3mL/min adopts conventional C18 preparative hplc post; Column temperature 20-40 ℃; The DAD detector: the detection wavelength is 520nm; According to appearance time; The anthocyanogen monomer absorption peak component of collecting; Further concentrate, under 40-45 ℃, rotary evaporation in vacuo concentrates; Obtain highly purified 3-[4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin monomer goods, this monomer structure is confirmed by mass spectroscopy and according to the reference report.
Concentration of hydrochloric acid according to the invention is 12M, and methyl alcohol according to the invention, said ETHYLE ACETATE and said formic acid are chromatographically pure.
Advantage of the present invention is:
L, the present invention adopt macroporous resin, attached gel, and separation and purification pattern stalk monomer adopts the preparation of half preparative hplc at last, and it is simple to operate, is prone to implement.
2, the pattern stalk of preparation is a high-purity monomer; Can be elected to be standard specimen; Be used for the research of physiologically active, pattern stalk stability and color mechanism etc., adopting the purity of 3-[4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin that preparation method of the present invention obtains is more than 99.79%.
Description of drawings
Figure l is the method preparation flow figure of 3-[4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin.
Fig. 2 is the high-efficient liquid phase chromatogram (520nm) of 3-among the embodiment 1 [4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-Glucopyranose stalk]-5-D-glycopyranoside delphinidin goods.
Embodiment
Invention specifically describes to wood through embodiment below, but technical scheme of the present invention is not limited to following cited embodiment.
The preparation flow of following examples is as shown in Figure 1.
Embodiment 1:
Fresh eggplant 5kg cleans, and arrangement separates skin and flesh, obtains eggplant skin 750g, chopping; With 1.5L, 0.01% methanol hydrochloride solution (v/v) mixes, at room temperature lixiviate 2h; Lixiviate obtains anthocyanogen extracting solution 50mL after the B suction filtration is filtrated and removed methyl alcohol at 43 ℃ of following rotary evaporations; Add the 100mL ethyl acetate extraction, extract three times, each consumption is 100mL, and the extraction liquid that obtains rotates evaporation concentration down at 42 ℃ and obtains anthocyanogen medicinal extract; With 0.01% (v/v) aqueous solution of hydrochloric acid dissolving of medicinal extract, obtain the anthocyanogen sample solution with 10-15mL;
Carry out acidifying in advance with 0.01% (v/v) aqueous solution of hydrochloric acid flushing XAD-7HP macroporous resin column
; With the flow velocity is that 0.5BV/h injects the anthocyanogen sample solution; After treating that absorption finishes, the deionized water of using the hydrochloric acid that contains 0.01% (v/v) is with the removal of impurities of 1BV/h flushing resin; Methanol hydrochloride solution with 0.01% (v/v) is resolved the anthocyanogen composition with the flow velocity of 1BV/h from resin; The rotation under 45 ℃ of collection elutriant is evaporated to no methyl alcohol and obtains the anthocyanogen liquid concentrator; Through the Sephadex LH-20 gel column of using 50% methanol-water solution (v/v) to handle in advance; Methanol aqueous solution with 50% (v/v) wash-out; Access once according to per 15 minutes, collect elutriant, the elutriant of collecting; At 40-45 ℃ of following rotary evaporation, obtain the anthocyanogen extract of preliminary purification; Use half preparative hplc separating monomer, chromatographic column is Agilent Eclipse XDB-C18 (9.4 * 250mmi.d., 5 μ m); Moving phase is respectively the A phase: 0.5% formic acid pure water (v/v), and the B phase: the methyl alcohol of 0.5% formic acid, (chromatographically pure, v/v); The condition of gradient elution (v/v) that adopts: 0-3min:40%B phase; The 3-10min:40%-50%B phase; The 10-12min:50%-70%B phase; The 12-15min:70%B phase; The 15-17min:70%-30%B phase; Flow velocity 3mL/min; Column temperature 20-40 ℃; The DAD detector: the detection wavelength is 520nm; Collect the absorption peak of corresponding RT 7.976min, obtain 3-[4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin (as shown in Figure 2) of 58mg, promptly yield is a 7.7mg/100g fresh weight eggplant skin.At the maximum absorption peak area of 520nm and the ratio of total material maximum absorption peak area summation in the 280-600nm scope, can calculate and obtain purity is 99.90% according to delphinidin.
Embodiment 2:
Fresh eggplant 10kg cleans, and arrangement separates skin and flesh, obtains eggplant skin 1500g, chopping; With 3L, 0.01% methanol hydrochloride solution (v/v) mixes, at room temperature lixiviate 2h; Lixiviate obtains anthocyanogen extracting solution 150mL after the B suction filtration is filtrated and removed methyl alcohol at 43 ℃ of following rotary evaporations; Add the 300mL ethyl acetate extraction, extract three times, each consumption is 300mL, and the extraction liquid that obtains rotates evaporation concentration down at 42 ℃ and obtains anthocyanogen medicinal extract; With 0.01% (v/v) aqueous solution of hydrochloric acid dissolving of medicinal extract, obtain the anthocyanogen sample solution with 30-50mL; (specific surface area is 500m with 0.01% (v/v) aqueous solution of hydrochloric acid flushing XAD-7HP macroporous resin column
2/ g; Mean pore size does
Median size is 560 μ m; Dipole moment is 1.8; Coefficient of uniformity D90/D40 is 1.7;
) carry out acidifying in advance, be that 0.5BV/h injects the anthocyanogen sample solution with the flow velocity, after waiting to adsorb end, with the deionized water 1L of the hydrochloric acid that contains 0.01% (v/v), with the removal of impurities of 1BV/h flushing resin; Methanol hydrochloride solution with 0.01% (v/v) is resolved the anthocyanogen composition with the flow velocity of 1BV/h from resin; The rotation under 45 ℃ of collection elutriant is evaporated to no methyl alcohol and obtains the anthocyanogen liquid concentrator; Through using the Sephadex LH-20 gel column of 50% (v/v) methanol-water solution-treated in advance
With the methanol-water wash-out of 50% (v/v), access once according to per 15 minutes, collect elutriant, with the elutriant of collecting,, obtain the anthocyanogen extract of preliminary purification at 40-45 ℃ of following rotary evaporation; Use half preparative hplc separating monomer, step is with embodiment 1.Obtain 3-[4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin of 113mg, promptly yield is a 7.5mg/100g fresh weight eggplant skin.Utilizing HPLC maximum absorption peak area ratio can obtain purity is 99.79%.
A kind of method for preparing high purity 3-[4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin of from the eggplant skin, separating of the present invention is described through concrete instance; Those skilled in the art can use for reference content of the present invention; Links such as appropriate change raw material, processing condition realize corresponding other purpose; Its relevant change does not all break away from content of the present invention; All similar replacements and change will become apparent to those skilled in the art that all to be regarded as and are included within the scope of the present invention.
Claims (5)
1. one kind is separated the method for preparing 3-[4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin from the eggplant skin, may further comprise the steps:
(1) raw materials pretreatment: with fresh eggplant clean, peeling, and the eggplant skin shredded;
(2) the eggplant pericarp anthocyanin is slightly carried liquid concentrator: with the eggplant skin that obtains, add according to the ratio of solid-liquid ratio 1g: 2mL in the methanol solution of 0.01% (v/v) hydrochloric acid, under the normal temperature; Lixiviate is filtered three times repeatedly; Merging filtrate is removed methyl alcohol at 40-45 ℃ of following rotary evaporation in vacuo and is obtained the anthocyanogen crude extract then, and in said crude extract: the volume ratio of ETHYLE ACETATE is that 1: 2 ratio adds ethyl acetate extraction; Standing demix extracts three times, collects to merge water; Remove ETHYLE ACETATE the 40-50 ℃ of abundant evaporation of following vacuum rotation, obtain anthocyanogen medicinal extract; Medicinal extract with the dissolving of a spot of 0.01% (v/v) aqueous solution of hydrochloric acid, is obtained the anthocyanogen sample solution;
(3) macroporous resin adsorption: macroporous adsorbent resin is packed in the chromatography column, wash with 0.01% (v/v) aqueous solution of hydrochloric acid; With the flow velocity injection macroporous resin column of said anthocyanogen sample solution with 0.5BV/h; Earlier wash resin with 1BV/h with the deionized water that contains 0.01% hydrochloric acid (v/v); Use the methanol solution of the hydrochloric acid of 0.01% (v/v) the anthocyanogen composition to be resolved from resin again with the flow velocity of 1BV/h; The desorbed solution that obtains is removed methyl alcohol at 40-45 ℃ of following rotary evaporation in vacuo, obtain the anthocyanogen bullion;
(4) gel-purified: will inject gel column from the anthocyanogen bullion that macroporous resin purification obtains; Methanol-water with 50% (v/v) wash-out; Accessed once according to per 15 minutes; Collect elutriant, the elutriant of collecting is removed methyl alcohol at 40-45 ℃ of following rotary evaporation in vacuo, obtain the anthocyanogen extract of preliminary purification;
(5) monomer preparation: utilize half preparative hplc to separate said anthocyanogen extract, moving phase is respectively the A phase: the pure water of 0.5% (v/v) formic acid, and the B phase: the methyl alcohol of 0.5% (v/v) formic acid, chromatographically pure; Adopt condition of gradient elution, adopt conventional C18 preparative hplc post, column temperature 20-40 ℃; The DAD detector: the detection wavelength is 520nm; According to appearance time; The anthocyanogen monomer absorption peak component of collecting further concentrates, under 40-45 ℃; Rotary evaporation in vacuo concentrates, and obtains said 3-[4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin;
The concentration of said hydrochloric acid is 12M, and said methyl alcohol, said ETHYLE ACETATE and said formic acid are chromatographically pure.
2. the method for claim 1, wherein said macroporous adsorbent resin is XAD-7HP, and specific surface area is 500m
2/ g, mean pore size does
Median size is 560 μ m, and dipole moment is 1.8, and coefficient of uniformity D90/D40 is 1.7.
3. the method for claim 1, wherein the diameter of said chromatography column is 50mm, and length is 600mm.
4. the method for claim 1, wherein said gel column is Sephadex LH-20, and said gel column diameter is 15mm, and length is 300mm.
5. the method for claim 1, wherein said condition of gradient elution is 0-3min:40% (v/v) B phase; 3-10min:40%-50% (v/v) B phase; 10-12min:50%-70% (v/v) B phase; 12-15min:70% (v/v) B phase; 15-17min:70%-30% (v/v) B phase; Flow velocity 3mL/min.
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Cited By (2)
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| CN108586414A (en) * | 2018-04-18 | 2018-09-28 | 安徽农业大学 | The method for preparing high-purity delphinidin from purple eggplant |
| CN112175028A (en) * | 2020-09-14 | 2021-01-05 | 浙江大学 | Method for separating and preparing delphinidin-3-O- (6-O-p-coumaroyl) glucoside |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108586414A (en) * | 2018-04-18 | 2018-09-28 | 安徽农业大学 | The method for preparing high-purity delphinidin from purple eggplant |
| CN112175028A (en) * | 2020-09-14 | 2021-01-05 | 浙江大学 | Method for separating and preparing delphinidin-3-O- (6-O-p-coumaroyl) glucoside |
| US11981697B2 (en) | 2020-09-14 | 2024-05-14 | Zhejiang University | Method for preparing delphinium acylated anthocyanin |
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