CN102796154B - 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 derivative, be specifically related to one from aubergine pigment, be separated the method preparing high purity 3-[4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin.
Background technology
Anthocyanogen (Anthocyanidin) is a kind of natural water colo(u)r, is widespread in nature, belongs to flavonoids.Anthocyanogen is by anthocyanogen aglycon and the polyphenols that is combined into by glycosidic link of sugar, and can also to be formed the anthocyanogen of acylations by ester bond with organic acid on glycosyl or hydroxyl.Research shows the chronic diseases such as anthocyanogen has the multiple physiologically active useful to human body, as cardiovascular in anti-oxidant activity, anti-inflammatory and prevention.Therefore factor application can be added as natural pigment, natural antioxidants and functional food.
Eggplant is a kind of common vegetables, and main being used as eats.In eggplant, in its purple or Black seed coat, be rich in abundant anthocyanogen.In the different Eggplant Varieties of current report, the kind of anthocyanogen mainly contains 3-[L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin of on-acylated and acidylate.The wherein anthocyanogen of acidylate, namely 3-[4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin is relatively stable, and in aubergine pigment rich content, its molecular structure is as follows.
To the extraction of anthocyanogen crude product the most frequently used be solvent-extraction process, common solvent has methyl alcohol, ethanol, acetone etc.What the purifying for anthocyanin class material was conventional is macroreticular resin absorbing method, and its efficiency is high, simple to operate, is applicable to extensive preparation.
High purity anthocyanogen not only has wide application potential at food, medicine, cosmetic field, and has very important value for the further investigation of the aspect such as colour stability and physiological function of single anthocyanogen.Now commercially available anthocyanogen mark product kind is few, and expensive.Especially acylations anthocyanogen standard substance are few.Therefore be that the highly purified acylations anthocyanin monomer of raw material separation preparation has great meaning with aubergine pigment.
Summary of the invention
The object of the present invention is to provide one from aubergine pigment, be separated the method preparing 3-[4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin, described method take eggplant as raw material, by being peeled, lixiviate concentrates, removal of impurities, macroporous resin purification, gel-purified, step in conjunction with half preparative chromatography, obtain 3-[4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin.The method is simple to operate, effectively can be separated from aubergine pigment and obtain highly purified anthocyanin monomer, and can realize extensive preparation.
For achieving the above object, the present invention adopts following scheme:
One is separated the method preparing 3-[4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin from aubergine pigment, comprises the following steps:
(1) raw materials pretreatment: fresh eggplant is carried out clean, peeling, and aubergine pigment is shredded;
(2) aubergine pigment anthocyanogen slightly carries concentrated solution: by the aubergine pigment obtained, according to solid-liquid ratio 1: 2 (w/v, g/mL) ratio adds in 0.01% methanol hydrochloride solution (v/v), under normal temperature, lixiviate, filter, three times repeatedly, then merging filtrate, at 40-45 DEG C, rotary evaporation in vacuo removing methyl alcohol obtains anthocyanogen crude extract, in described crude extract: the volume ratio of ethyl acetate be 1: 2 ratio add extraction into ethyl acetate, stratification, extract three times, collect and merge aqueous phase, the abundant evaporative removal ethyl acetate of vacuum rotating at 40-50 DEG C, obtain anthocyanogen medicinal extract, by the aqueous dissolution of medicinal extract with a small amount of 0.01% (v/v) hydrochloric acid, obtain anthocyanogen sample solution,
(3) macroporous resin adsorption: macroporous adsorbent resin is loaded chromatography column
in, rinse with 0.01% (v/v) salt aqueous acid; Anthocyanogen sample solution is injected macroporous resin column with the flow velocity of 0.5BV/h, first rinse resin with the deionized water of the hydrochloric acid (v/v) containing 0.01% with 1BV/h, the methanol hydrochloride solution of 0.01% (v/v) is used to be resolved from resin by anthocyanogen composition with the flow velocity of 1BV/h again, by the desorbed solution rotary evaporation in vacuo removing methyl alcohol at 40-45 DEG C obtained, obtain anthocyanogen crude product;
(4) gel-purified: the anthocyanogen crude product obtained from macroporous resin purification is injected gel column
methanol-water (v/v) wash-out with 50%, accessed once according to every 15 minutes, collected elutriant, and by the elutriant collected, at 40-45 DEG C, rotary evaporation in vacuo removing methyl alcohol, obtains the Anthocyanin-rich Extract of preliminary purification; Described macroporous adsorbent resin is that (specific surface area is 500m to XAD-7HP
2/ g; Mean pore size is
median size is 560 μm; Dipole moment is 1.8; Coefficient of uniformity D90/D40 is 1.7); Described gel column is Sephadex LH-20 (separating ranges 100-4000; Granular size is 20-150 μm);
(5) monomer preparation: utilize half preparative chromatography to be separated anthocyanin monomer, the anthocyanogen obtained by purifying from gel column extracts sample, is separated, service routine 1 preparative separation by half preparative chromatography; Moving phase in described program l is respectively 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) adopted: 0-3min:40%B phase; 3-10min:40%-50%B phase; 10-12min:50%-70%B phase; 12-15min:70%B phase; 15-17min:70%-30%B phase; Flow velocity 3mL/min, adopts conventional C18 preparative chromatography post; Column temperature 20-40 DEG C; DAD detector: determined wavelength is 520nm; According to appearance time, the anthocyanin monomer absorption peak component collected, concentrated further, at 40-45 DEG C, 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 by mass spectroscopy and according to reference report and determine.
Concentration of hydrochloric acid of the present invention is 12M, and methyl alcohol of the present invention, described ethyl acetate and described formic acid are chromatographically pure.
Advantage of the present invention is:
L, the present invention adopt macroporous resin, attached gel, separation and purification pattern stalk monomer, and finally adopt half preparative chromatography preparation, it is simple to operate, easily implements.
2, the pattern stalk of preparation is high-purity monomer, standard specimen can be elected to be, for the research of physiologically active, pattern stalk stability and color mechanism etc., the purity of the 3-adopting preparation method of the present invention to obtain [4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin is more than 99.79%.
Accompanying drawing explanation
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-in embodiment 1 [4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-Glucopyranose stalk]-5-D-glycopyranoside delphinidin goods.
Embodiment
Below by embodiment, wood invention is specifically described, but technical solution of the present invention is not limited to following cited embodiment.
The preparation flow of following examples as shown in Figure 1.
Embodiment 1:
Fresh eggplant 5kg, cleaning, arranges, and is separated by skin and flesh, obtains aubergine pigment 750g, chopping; With 1.5L, 0.01% methanol hydrochloride solution (v/v) mixes, at room temperature lixiviate 2h; Through Büchner funnel suction filtration after lixiviate, filtrate rotates methanol removed by evaporation at 43 DEG C, obtains anthocyanogen extracting solution 50mL; Add 100mL extraction into ethyl acetate, extract three times, each consumption is 100mL, and the extraction liquid obtained rotates evaporation concentration and obtains anthocyanogen medicinal extract at 42 DEG C; By the aqueous dissolution of 0.01% (v/v) hydrochloric acid of medicinal extract 10-15mL, obtain anthocyanogen sample solution;
XAD-7HP macroporous resin column is rinsed with 0.01% (v/v) salt aqueous acid
carrying out acidifying in advance, is that 0.5BV/h injects anthocyanogen sample solution with flow velocity, after end upon adsorption, rinses resin removal of impurities with the deionized water of the hydrochloric acid containing 0.01% (v/v) with 1BV/h; Anthocyanogen composition is resolved from resin with the flow velocity of 1BV/h with the methanol hydrochloride solution of 0.01% (v/v); Collection elutriant rotates to be evaporated to and obtains anthocyanogen concentrated solution without methyl alcohol at 45 DEG C; Through the Sephadex LH-20 gel column using 50% methanol-water solution (v/v) to process in advance, methanol aqueous solution (v/v) wash-out with 50%, accessed once according to every 15 minutes, collect elutriant, by the elutriant collected, rotary evaporation at 40-45 DEG C, obtains the Anthocyanin-rich Extract of preliminary purification; Use half preparative chromatography separating monomer, chromatographic column is Agilent EclipseXDB-C18 (9.4 × 250mmi.d., 5 μm); Moving phase is respectively A phase: 0.5% formic acid pure water (v/v), B phase: the methyl alcohol of 0.5% formic acid, (chromatographically pure, v/v); The condition of gradient elution (v/v) adopted: 0-3min:40%B phase; 3-10min:40%-50%B phase; 10-12min:50%-70%B phase; 12-15min:70%B phase; 15-17min:70%-30%B phase; Flow velocity 3mL/min; Column temperature 20-40 DEG C; DAD detector: determined wavelength is 520nm; Collect the absorption peak of corresponding retention time 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, namely yield is 7.7mg/100g fresh weight aubergine pigment.According to the maximum absorption peak area of delphinidin at 520nm and the ratio of total material maximum absorption peak area summation within the scope of 280-600nm, can calculate and obtain purity is 99.90%.
Embodiment 2:
Fresh eggplant 10kg, cleaning, arranges, and is separated by skin and flesh, obtains aubergine pigment 1500g, chopping; With 3L, 0.01% methanol hydrochloride solution (v/v) mixes, at room temperature lixiviate 2h; Through Büchner funnel suction filtration after lixiviate, filtrate rotates methanol removed by evaporation at 43 DEG C, obtains anthocyanogen extracting solution 150mL; Add 300mL extraction into ethyl acetate, extract three times, each consumption is 300mL, and the extraction liquid obtained rotates evaporation concentration and obtains anthocyanogen medicinal extract at 42 DEG C; By the aqueous dissolution of 0.01% (v/v) hydrochloric acid of medicinal extract 30-50mL, obtain anthocyanogen sample solution; (specific surface area is 500m to rinse XAD-7HP macroporous resin column with 0.01% (v/v) salt aqueous acid
2/ g; Mean pore size is
median size is 560 μm; Dipole moment is 1.8; Coefficient of uniformity D90/D40 is 1.7;
) carry out acidifying in advance, be that 0.5BV/h injects anthocyanogen sample solution with flow velocity, after end upon adsorption, with the deionized water 1L of the hydrochloric acid containing 0.01% (v/v), rinse resin removal of impurities with 1BV/h; Anthocyanogen composition is resolved from resin with the flow velocity of 1BV/h with the methanol hydrochloride solution of 0.01% (v/v); Collection elutriant rotates to be evaporated to and obtains anthocyanogen concentrated solution without methyl alcohol at 45 DEG C; Through using the Sephadex LH-20 gel column of 50% (v/v) methanol-water solution process in advance
with the methanol-water wash-out of 50% (v/v), accessed once according to every 15 minutes, collect elutriant, by the elutriant collected, rotary evaporation at 40-45 DEG C, obtains the Anthocyanin-rich Extract of preliminary purification; Use half preparative chromatography 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, namely yield is 7.5mg/100g fresh weight aubergine pigment.Utilizing HPLC maximum absorption peak area ratio can obtain purity is 99.79%.
One of the present invention is separated the method preparing high purity 3-[4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin and is described by concrete example from aubergine pigment, those skilled in the art can use for reference content of the present invention, appropriate change raw material, the links such as processing condition realize other object corresponding, its relevant change does not all depart from content of the present invention, all similar replacements and change it will be apparent to those skilled in the art that, all be deemed to be included within scope of the present invention.
Claims (1)
1. from aubergine pigment, be separated the method preparing 3-[4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin, comprise the following steps:
(1) raw materials pretreatment: fresh eggplant is carried out clean, peeling, and aubergine pigment is shredded;
(2) aubergine pigment anthocyanogen slightly carries concentrated solution: by the aubergine pigment obtained, adding volume ratio according to the ratio of solid-liquid ratio 1g ︰ 2mL is in the methanol solution of the hydrochloric acid of 0.01%, under normal temperature, lixiviate, filter, three times repeatedly, then merging filtrate, at 40-45 DEG C, rotary evaporation in vacuo removing methyl alcohol obtains anthocyanogen crude extract, the ratio being 1 ︰ 2 in the volume ratio of described thick Ti Ye ︰ ethyl acetate adds extraction into ethyl acetate, stratification, extract three times, collect and merge aqueous phase, at 40-50 DEG C, vacuum rotating fully evaporates removing ethyl acetate, obtain anthocyanogen medicinal extract, be the aqueous dissolution of the hydrochloric acid of 0.01% by a small amount of volume ratio by medicinal extract, obtain anthocyanogen sample solution,
(3) macroporous resin adsorption: loaded by macroporous adsorbent resin in chromatography column, rinses with the salt aqueous acid that volume ratio is 0.01%; Described anthocyanogen sample solution is injected macroporous resin column with the flow velocity of 0.5BV/h, first rinse resin with the deionized water containing volume ratio being the hydrochloric acid of 0.01% with 1BV/h, be that anthocyanogen composition is resolved from resin with the flow velocity of 1BV/h by the methanol solution of the hydrochloric acid of 0.01% again by volume ratio, by the desorbed solution rotary evaporation in vacuo removing methyl alcohol at 40-45 DEG C obtained, obtain anthocyanogen crude product; Wherein, described macroporous adsorbent resin is XAD-7HP, and specific surface area is 500m
2/ g, mean pore size is
median size is 560 μm, and dipole moment is 1.8, and coefficient of uniformity D90/D40 is 1.7; Wherein, the diameter of described chromatography column is 50mm, and length is 600mm;
(4) gel-purified: the anthocyanogen crude product obtained from macroporous resin purification is injected gel column, with the methanol-water wash-out that volume ratio is 50%, accessed once according to every 15 minutes, collect elutriant, by the elutriant rotary evaporation in vacuo removing methyl alcohol at 40-45 DEG C collected, obtain the Anthocyanin-rich Extract of preliminary purification; Wherein, described gel column is Sephadex LH-20, and described gel column diameter is 15mm, and length is 300mm;
(5) monomer preparation: utilize half preparative chromatography to be separated described Anthocyanin-rich Extract, moving phase is respectively A phase: volume ratio is the pure water of the formic acid of 0.5%, B phase: volume ratio is the methyl alcohol of the formic acid of 0.5%, chromatographically pure; Adopt condition of gradient elution, adopt conventional C18 preparative chromatography post, column temperature 20-40 DEG C; DAD detector: determined wavelength is 520nm; According to appearance time, the anthocyanin monomer absorption peak component collected, concentrates, further at 40-45 DEG C, rotary evaporation in vacuo concentrates, and obtains described 3-[4-p-coumaric acyl-L-rhamanopyranosyl-(1 → 2)-D-glucopyranoside]-5-D-glycopyranoside delphinidin; Wherein, described condition of gradient elution is 0-3min: volume ratio is the B phase of 40%; 3-10min: volume ratio is the B phase of 40%-50%; 10-12min: volume ratio is the B phase of 50%-70%; 12-15min: volume ratio is the B phase of 70%; 15-17min: volume ratio is the B phase of 70%-30%; Flow velocity 3mL/min;
The concentration of described hydrochloric acid is 12M, and described methyl alcohol, described ethyl acetate and described formic acid are chromatographically pure.
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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 |
| CN112175028B (en) * | 2020-09-14 | 2021-09-21 | 浙江大学 | Method for separating and preparing delphinidin-3-O- (6-O-p-coumaroyl) glucoside |
Citations (1)
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| CN102060833A (en) * | 2010-11-29 | 2011-05-18 | 中国科学院西北高原生物研究所 | Method for extracting anthocyanin from lycium ruthenicum fruit |
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| JP2002322055A (en) * | 2001-04-26 | 2002-11-08 | Sanei Gen Ffi Inc | Carciniostatic agent comprising delphinidin compound |
| JP2005304466A (en) * | 2004-04-24 | 2005-11-04 | Yasumasa Tsukuda | Extraction of nasunine or the like and method for producing the same |
| JP2006333862A (en) * | 2004-07-26 | 2006-12-14 | Yasumasa Tsukuda | Food comprising nasunine and method for production of the same |
| JP2007191683A (en) * | 2005-10-07 | 2007-08-02 | Yasumasa Tsukuda | Food containing nasunine or the like and method for producing the same |
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| CN102060833A (en) * | 2010-11-29 | 2011-05-18 | 中国科学院西北高原生物研究所 | Method for extracting anthocyanin from lycium ruthenicum fruit |
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| Nasunin from Eggplant Consists of Cis−Trans Isomers of Delphinidin 3-[4-(p-Coumaroyl)-L-rhamnosyl (1f6)glucopyranoside]-5-glucopyranoside;TAKASHI ICHIYANAGI,等;《J. Agric. Food Chem.》;20051101;第53卷(第24期);第9472-9477页 * |
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