CN103641867A - High-speed counter-current chromatography separation method and application of phenolic acid glycoside compounds in traditional Chinese medicine lily - Google Patents
High-speed counter-current chromatography separation method and application of phenolic acid glycoside compounds in traditional Chinese medicine lily Download PDFInfo
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Abstract
The invention relates to a high-speed counter-current chromatography separation method and an application of phenolic acid glycoside compounds in traditional Chinese medicine lily. The method is characterized by comprising the steps of mixing ethyl acetate, normal butanol and 0.5% acetic acid aqueous solution in a volume ratio of 3: 1.5: 5 to obtain a high-speed counter-current solvent system, and separating the traditional Chinese medicine lily extract through a high-speed counter-current chromatography way so as to prepare three phenolic acid glycoside compounds in the traditional Chinese medicine lily. Research on the biological activities of the compounds shows that the three compounds have certain removal effect on DPPH free radicals, can inhibit the fat peroxide to some extent and can promote the activity of alpha-diastasum diastace.
Description
Technical field
The present invention relates to the separation method of phenolic acid glyceryl ester glycoside compound in Bulbus Lilii, be specifically related to a kind of with high-speed countercurrent chromatography separated method of preparing phenolic acid glyceryl ester glycoside compound from Bulbus Lilii.
Background technology
Lily (Liliaceae) is per nnial herb, approximately there is lily kind more than 90 in the whole world, approximately there are 46 kinds of 18 mutation in China, wherein tiger lily (Lilium lancifolium Thunb), lily (Lilium brownii F.E.Brown var.viridulum Baker) or the dry meat bulb of Lilium tenuifolium (L.pumilum DC.) are the medicinal kinds of recording in China's pharmacopeia, also be extensive medicinal and edible plant among the people, there is the merit of nourishing YIN and clearing away lung-heat, clearing away the heart fire and tranquillizing.In prior art generally by silica gel repeatedly the multiple coupling technique such as column chromatography, gel chromatography and Preparative TLC chromatogram from different varieties lily plant, isolate the number of chemical compositions such as phenolic acid glyceryl ester glycosides, phenolic acid glyceryl ester, steroidal saponin, alkaloid, glycerine glycosides, flavones.But chemical composition and biological activity thereof in three medicinal kinds of China rarely have report.
High speed adverse current chromatogram (HSCCC) is that development in recent years a kind of is widely used in liquid luquid partition chromatography technology prepared by Separation of Natural Products, has easy and simple to handle, favorable reproducibility, feature that preparation amount is large, is widely used in the preparation of natural active matter.But the method for preparing phenolic acid glyceryl ester glycoside compound from Bulbus Lilii separation with this high-speed countercurrent chromatography is not reported.
Summary of the invention
Technical problem to be solved by this invention is: for above-mentioned the deficiencies in the prior art, provide high speed adverse current chromatogram separation method and the application of phenolic acid glyceryl ester glycoside compound in a kind of Bulbus Lilii.
In order to solve the problems of the technologies described above, the technical solution adopted in the present invention is: the high speed adverse current chromatogram separation method of phenolic acid glyceryl ester glycoside compound in a kind of Bulbus Lilii, and the method step is as follows:
A. prepare Bulbus Lilii extract: get lily bulb powder, the ethanol that the mass concentration that is incorporated as 5-10 times of quality is 40-60% is in 50-70 ℃ of water-bath lixiviate 3 times, each 0.5-1h, merging filtrate, filtrate decompression is concentrated into without alcohol taste; By this extracting solution with 1-3BV/h flow velocity by the chromatography column of D101 macroporous adsorbent resin is housed, standing 0.5-1h after absorption, with distilled water, with the drip washing of 2-4BV/h flow velocity, remove impurity, with the ethanol of 70% mass concentration, with 2-4BV/h flow velocity, be washed till elutriant without color again, by ethanol eluate concentrating under reduced pressure postlyophilization, obtain Bulbus Lilii extract;
B. high-speed countercurrent chromatography is separated: by ethyl acetate, propyl carbinol and 0.5% acetic acid aqueous solution by volume 3:1.5:5 form high-speed counter-current solvent system, fully mix, stratification spends the night, by upper with under be separated, upper is stationary phase mutually, and lower is moving phase mutually, ultrasonic degas 10-20min, the ratio that the Bulbus Lilii extract making is added to phase under 10-20mL in every 200mg-250mg with lower phased soln as sample solution, flow velocity injection high-speed counter-current chromatograph by upper phase solvent with 20mL/min, after upper phase solvent is full of, under the rotating speed of 800-900rpm/min, the flow velocity with 1.5-2mL/min under residue is injected, detection wavelength is 280nm, after balance by sample solution sample introduction, after 80-100min, carry out collection of illustrative plates collection (different according to the flow velocity different acquisition time), according to the manual Fractional Collections effluent liquid of peak shape, by the effluent liquid concentrating under reduced pressure postlyophilization of collecting, obtain powdered compounds regaloside A, compd A cetylregaloside C and compound regaloside B.
Above-mentioned lily bulb powder is to get fresh Bulbus Lilii in 50-60 ℃ of baking oven, to be dried to water content be 7-9%, and being crushed to particle diameter is 10-20 order.This Bulbus Lilii refers to the lily (Lilium brownii F.E.Brown var.viridulum Baker) in tiger lily (Lilium lancifolium Thunb), lily (Lilium brownii F.E.Brown var.viridulum Baker) and three the medicinal kinds of Lilium tenuifolium (L.pumilum DC.) in lily.
The present invention utilizes HSCCC technology from Bulbus Lilii, to prepare separation and obtains 3 compounds, and the method is easy, efficient, a large amount of preparations of suitable compound; , on the oxidation-resistance of these 3 kinds of compounds and on the impact of amylase activity, be studied, Regaloside A and Regaloside B have certain restraining effect to lipid peroxidation meanwhile; Acetylregaloside C is all stronger to the effect of the two, and three kinds of compounds all have certain promoter action to alpha-amylase activity, show that Bulbus Lilii may have the function helping digestion, for the further pharmacological research of Bulbus Lilii and quality control lay the foundation.
Accompanying drawing explanation
Fig. 1 is lily extracting solution HPLC spectrogram.
Fig. 2 is the HPLC color atlas of the color atlas of Bulbus Lilii extract employing HSCCC separation 3 compounds separated with HSCCC.
Wherein: A is the color atlas of HSCCC separation; B-C is HPLC color atlas, and B represents compound 1; C represents compound 2; D represents compound 3.
Fig. 3 is that 3 compounds are to diastatic promoter action.
Embodiment
The raw material of using in following examples and instrument and HPLC analysis condition:
Lily is purchased from lily planting base, Longshan County, Hunan Province, kind Lilium brownii F.E.Brown var.viridulum Baker.
LC10AT-VP Plus highly effective liquid phase chromatographic system (Japanese Shimadzu company), is furnished with: LC-10AT high-pressure pump, SPD-10A VP UV-detector, wondasil
tMc
18reverse-phase chromatographic column (150mm * 4.6mm, 5 μ m).
TBE-300A type high speed adverse current chromatogram (HSCCC) instrument (tetrafluoroethylene post, internal diameter 1.6mm, column volume 280mL, rotating speed 0-1000r/min) (Chinese Shanghai Tong Tian biochemical technology company limited), be furnished with: TBD-2000 Ultraviolet Detector, LX-300 thermostatted, TBP-50A constant flow pump (Beijing scientific and technological instrument company of long stream).
High performance liquid chromatography (HPLC) analysis condition: adopt wondasil
tMc18(4.6 * 250mm) chromatographic column; Moving phase is A pump: water, and B pump: methyl alcohol, adopts gradient elution method wash-out: 0-40min(B:20% → 80%), flow velocity 1.0mL/min; Column temperature: 30 ℃, sample size 20 μ L.
The preparation of phenolic acid glyceryl ester glycoside compound in embodiment 1 Bulbus Lilii
1. the preparation of Bulbus Lilii extract
Getting new fresh Bulbus Lilii phosphorus stem puts in 50 ℃ of baking ovens and dry, pulverize; Get the dry lily bulb powder of 830g, add the ethanol of 60% mass concentration of 6 times of quality to soak 3 times in 60 ℃ of water-baths, each 1h, merging filtrate, filtrate decompression is concentrated into without alcohol taste, obtains 3200mL extracting solution.By this extracting solution with 2BV/h flow velocity by the chromatography column (4.6cm * 48cm) of 800mL D101 macroporous adsorbent resin is housed, standing 0.5h after absorption, with 1600mL distilled water, with the drip washing of 2BV/h flow velocity, remove impurity, with the ethanol of 70% mass concentration, with 2BV/h flow velocity, be washed till elutriant more colourless, by the ethanol eluate 2900mL concentrating under reduced pressure postlyophilization obtaining, obtain Bulbus Lilii extract 6.5g, be placed in refrigerator and keep in Dark Place, as the sample introduction raw material of HSCCC.
The HPLC of lily phosphorus stem extract analyzes: the HPLC figure of lily 60% ethanol extract making under above-mentioned efficient liquid phase chromatographic analysis condition is shown in Fig. 1.As seen from the figure, in extracting solution, contain multiple compounds, PDA detector shows the ultra-violet absorption spectrum of each main chromatographic peak, a plurality of compounds in color atlas all have similar ultra-violet absorption spectrum, in 310nm left and right, there is maximum absorption, at 220nm, have more by force and absorb, wherein compound 1,2,3 relative contents are higher, as HSCCC separate targets.
2. high speed adverse current chromatogram (HSCCC) sepn process
By ethyl acetate-propyl carbinol-0.5% acetic acid aqueous solution (3:1.5:5, V/V) preparation solvent system, all solvents are fully mixed by volume, after stratification spends the night, by upper with under be separated; Get the Bulbus Lilii extract 250mg making, with phased soln under 20mL as sample solution, after ultrasonic degas 15min, upper phase solvent is entered to main frame pipeline with the flow pump of 20mL/min, until upper phase solvent, be full of after pipeline, instrument is rotated in the forward with 850rpm/min rotating speed, 25 ℃ of column ovens, again the lower flow pump with 2mL/min is entered to main frame pipeline, detect wavelength 280nm.Extracting sample solution sample introduction after balance, after 80min, carry out collection of illustrative plates collection, the color atlas of HSCCC separation is shown in Fig. 2 A, according to the manual Fractional Collections effluent liquid of peak shape, obtain 3 compounds, through concentrated, lyophilize and carry out HPLC analysis (analysis condition see on) to obtain 4.2mg purity be 96.2% compound 1, the compound 2 that 2.3mg purity is 95.1%, 5.8mg purity is that 98.8% compound 3(adopts area normalization method to calculate under 254nm wavelength), referring to Fig. 2 B-Fig. 2 D.
Employing MS,
1h NMR and
13c NMR carries out Structural Identification to 3 compounds.Mass spectrum adopts electron spray ionisation source ESI, and negative ion mode, is completed by Institute of Analysis of Agricultural University Of Hunan; Nuclear magnetic resonance sample CD
3oD dissolves, and frequency is 400MHz, by Institute of Analysis of chemical engineering institute of Hunan University, is completed.
Determine that these 3 compounds are phenolic acid glyceryl ester glycoside compound, wherein:
The compound 1 of buff powder is
(2S)-1-O-p-coumaroyl-3-O-β-D-glucopyranosylylycerol(regaloside A), molecular formula: C
18h
24o
10;
The compound 2 of yellow powder is (2S)-1-O-acetyl
Caffeoyl-3-O-β-D-glucopyranosylylycerol, i.e. Acetylregaloside C, molecular formula: C
20h
26o
12;
The compound 3 of buff powder is
(2S)-1-O-p-coumaroyl-2-O-β-D-glucopyranosylylycerol-3-O-acetylglycerol(regaloside B), molecular formula: C
20h
26o
11.
The structure of 3 compounds is as follows:
33 compounds of embodiment are to the scavenging(action) of DPPH free radical and the restraining effect to lipid peroxidation
Scavenging(action) reference literature G.A.Garz ó n to DPPH free radical, R E.Wrolstad.Major anthocyanins and antioxidant activity of Nasturtium flowers (Tropaeolum majus) .Food Chem., 2009,114 (1): the method for 44-49 is carried out.
Restraining effect reference literature Zhang Erxian, Yu Lijun, Zhou Yilin etc. to lipid peroxidation, Fe2+ brings out lipid protein PUFA peroxidation system and to the evaluation of some natural product antioxygenations [J]. Acta Biochimica et Biophysica Sinica (Acta Biochimica et Biophysica Sinica), 1996,2 (28): the method for 218-222 is carried out.
The results are shown in following table 1, as seen from table, 2 pairs of lipid peroxidations of compound have very strong restraining effect, also stronger to DPPH free radical scavenging effect, when sample concentration is respectively 20 μ g/mL, 100 μ g/mL, Lipid peroxidation is respectively to 84.9% and 97.9%, is far longer than with isocyatic V
c, DPPH free radical scavenging effect is respectively to 20.2% and 84.2%, be weaker than with isocyatic V
c.1,3 pairs of DPPH scavenging(action)s of compound are very weak, but lipid peroxidation is had to certain restraining effect.Compound and positive control V
cto DPPH, free radical scavenging act as: V
c> compound 2 > compound 1 ≈ compounds 3, and Lipid peroxidation is respectively: compound 2 > V
c> compound 3 ≈ compounds 1.
Table 13 compound is to DPPH free radical scavenging effect and to Lipid peroxidation
The impact of 43 compounds of embodiment on pig pancreaticα-amylase activity
Present method reference literature S.L.Udupa, A.R.Prabhakar, S.Tandon. α-Amylase inhibitors in foodstuffs[J] .Food Chem., the method for 1989,34:95-101 is measured.
According to light absorption value, judge that sample has promoter action to enzymic activity, according to following formula, calculate promotion rate:
Alpha-amylase activity promotion rate (%)=(A
1-A
2-A
0)/A
0* 100.
The results are shown in Figure 3, as seen from the figure, within the scope of experimental concentration, 3 compounds all can strengthen alpha-amylase activity, and these 3 compounds have certain promoter action to alpha-amylase activity.Along with sample concentration increases 1.67mg/ml from 0.33mg/ml, the promoter action of compound 1 rises to 36.6% from 10.3%, and compound 2 rises to 28.9%, compound 3 from 21.2% to 30.2% from 6.4%.
Claims (4)
1. a high speed adverse current chromatogram separation method for phenolic acid glyceryl ester glycoside compound in Bulbus Lilii, is characterized in that: the method step is as follows:
A. prepare Bulbus Lilii extract: get Bulbus Lilii powder, the ethanol that the mass concentration that adds 5-10 times of quality is 40-60% is in 50-70 ℃ of water-bath lixiviate 3 times, each 0.5-1h, merging filtrate, filtrate decompression is concentrated into without alcohol taste; By this extracting solution with 1-3BV/h flow velocity by the chromatography column of D101 macroporous adsorbent resin is housed, standing 0.5-1h after absorption, with distilled water, with the drip washing of 2-4BV/h flow velocity, remove impurity, with the ethanol of 70% mass concentration, with 2-4BV/h flow velocity, be washed till elutriant without color again, by ethanol eluate concentrating under reduced pressure postlyophilization, obtain Bulbus Lilii extract;
B. high-speed countercurrent chromatography is separated: by ethyl acetate, propyl carbinol and 0.5% acetic acid aqueous solution by volume 3:1.5:5 form high-speed counter-current solvent system, fully mix, stratification spends the night, by upper with under be separated, ultrasonic degas, the ratio that the Bulbus Lilii extract making is added to phase under 10-20mL in every 200mg-250mg with lower phased soln as sample solution, flow velocity injection high-speed counter-current chromatograph by upper phase solvent with 20mL/min, after upper phase solvent is full of, under the rotating speed of 800-900rpm/min, the flow velocity with 1.5-2mL/min under residue is injected, detection wavelength is 280nm, after balance by sample solution sample introduction, after 80-100min, carry out collection of illustrative plates collection, according to the manual Fractional Collections effluent liquid of peak shape, by the effluent liquid concentrating under reduced pressure postlyophilization of collecting, obtain powdered compounds regaloside A, compd A cetylregaloside C and compound regaloside B.
2. the high speed adverse current chromatogram separation method of phenolic acid glyceryl ester glycoside compound in Bulbus Lilii as claimed in claim 1, it is characterized in that: described Bulbus Lilii powder is to get fresh Bulbus Lilii in 50 ℃ of-60 ℃ of baking ovens, to be dried to water content be 7-9%, and being crushed to particle diameter is 10-20 order.
3. the application of the compound that method obtains as claimed in claim 1 in DPPH free radical scavenging effect and Lipid peroxidation.
4. the compound that method obtains is as claimed in claim 1 in the application in the promoter action of alpha-amylase activity.
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Cited By (4)
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| CN104892687A (en) * | 2015-06-11 | 2015-09-09 | 淮阴师范学院 | Method for separating and purifying monomeric compound from Chinese mahonia leaves through high-speed counter-current chromatography |
| CN107698637A (en) * | 2017-10-27 | 2018-02-16 | 张良波 | A kind of Asiatic sweet leaf fruit compound high speed adverse current chromatogram preparation method |
| CN109180584A (en) * | 2018-07-25 | 2019-01-11 | 湖南农业大学 | A method of separating norisoboldine from the root of three-nerved spicebush |
| CN117659102A (en) * | 2024-01-11 | 2024-03-08 | 北京林业大学 | Method for simultaneously separating and purifying 10 kinds of lilac glycoside compounds from lily |
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| US20070037756A1 (en) * | 2005-08-12 | 2007-02-15 | Leadtrek, Inc | Compositions and methods for the prevention and treatment of circulatory conditions |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104892687A (en) * | 2015-06-11 | 2015-09-09 | 淮阴师范学院 | Method for separating and purifying monomeric compound from Chinese mahonia leaves through high-speed counter-current chromatography |
| CN104892687B (en) * | 2015-06-11 | 2017-12-08 | 淮阴师范学院 | The method that high speed adverse current chromatogram isolates and purifies monomeric compound in Chinese mahonia leaf |
| CN107698637A (en) * | 2017-10-27 | 2018-02-16 | 张良波 | A kind of Asiatic sweet leaf fruit compound high speed adverse current chromatogram preparation method |
| CN107698637B (en) * | 2017-10-27 | 2019-11-12 | 张良波 | A kind of Asiatic sweet leaf fruit compound high speed adverse current chromatogram preparation method |
| CN109180584A (en) * | 2018-07-25 | 2019-01-11 | 湖南农业大学 | A method of separating norisoboldine from the root of three-nerved spicebush |
| CN117659102A (en) * | 2024-01-11 | 2024-03-08 | 北京林业大学 | Method for simultaneously separating and purifying 10 kinds of lilac glycoside compounds from lily |
| CN117659102B (en) * | 2024-01-11 | 2024-05-07 | 北京林业大学 | Method for simultaneously separating and purifying 10 kinds of lilac glycoside compounds from lily |
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