CN108760948A - A kind of preparation method of 1,2,3,4,6-O- Penta-O-galloyl-D-glucopyranoses standard sample - Google Patents

A kind of preparation method of 1,2,3,4,6-O- Penta-O-galloyl-D-glucopyranoses standard sample Download PDF

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CN108760948A
CN108760948A CN201810815957.XA CN201810815957A CN108760948A CN 108760948 A CN108760948 A CN 108760948A CN 201810815957 A CN201810815957 A CN 201810815957A CN 108760948 A CN108760948 A CN 108760948A
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methanol
galloyl
pentagluacyl
acetone
penta
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张亮亮
汪咏梅
徐曼
胡新宇
刘瑜琛
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Institute of Chemical Industry of Forest Products of CAF
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    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
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    • 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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    • 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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    • G01N30/02—Column chromatography
    • G01N30/04—Preparation or injection of sample to be analysed
    • G01N30/06—Preparation
    • G01N30/12—Preparation by evaporation
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Abstract

The invention discloses one kind 1, 2, 3, 4, the preparation method and application of 6-O- Penta-O-galloyl-D-glucopyranose standard samples, by Chinese gallotanninic acid after the degradation of methanol acetum, it is evaporated under reduced pressure and removes organic solvent, ether and ethyl acetate is used to extract respectively again, ethyl acetate portion, which is evaporated under reduced pressure, removes organic solvent, it is freeze-dried to obtain crude product, then pass through sephadex chromatography pillar layer separation after being dissolved with methanol, collect 70% acetone elution fraction, it is evaporated under reduced pressure and removes acetone, 1 is obtained after water phase is freeze-dried, 2, 3, 4, 6-O- Penta-O-galloyl-D-glucopyranose standard samples.1,2,3,4,6-O-pentagluacyl glucose standard sample uniformity prepared by this method is good, magnitude is accurate, stability is good, to detect, quantify etc. and provide good standard items for 1,2,3,4,6-O-pentagluacyl glucose content in plant sample.

Description

A kind of preparation method of 1,2,3,4,6-O-pentagluacyl glucose standard sample
Technical field
The present invention relates to a kind of preparation methods of 1,2,3,4,6-O-pentagluacyl glucose standard sample, belong to analysis Detection technique field.
Technical background
Tannic acid (Tannic acid) be from Chinese gall, tower draw etc. rich in tannin plant sample in extraction prepare by A kind of natural polyphenol compound of the polymer for the ester that different number galloyl bases and glucose are formed.Therefore, chemically on ingredient See that tannic acid is by the mixture of the gallate of different polymerization degree.Wherein again with 1,2,3,4,6-O-pentagluacyl glucose (PGG) content is main component.1,2,3,4,6-O-pentagluacyl glucose has stronger bioactivity, is widely present In various plants, while it being also the important indicator of traditional Chinese medicine quality control.But due to lacking reference substance, give the quality of Related product Control brings certain difficulty.Therefore it provides a kind of method preparing 1,2,3,4,6-O-pentagluacyl glucose reference substance Have great importance.1,2,3,4,6-O-pentagluacyl glucose content in Chinese medicine Chinese gall is higher, due to Chinese gall In there is also similar other chemical compositions, cause its separation to prepare difficult.The present invention provides a kind of using tannic acid as raw material, profit With the tannic acid method that 1,2,3,4,6-O-pentagluacyl glucose is prepared in alcoholysis in the methanol of heat.It is prepared by this method Process is as follows：
Invention content
The object of the present invention is to provide a kind of preparation methods of 1,2,3,4,6-O-pentagluacyl glucose standard sample.
The present invention is prepared especially by following steps：
(1) using tannic acid as material, by tannic acid according to tannic acid: methanol acetum=1: 5-20's (g/mL) Ratio is dissolved in methanol acetum reacts 15h in 65 DEG C.Wherein methanol concentration of volume percent is in methanol acetum 70%, the acetic acid of a concentration of 0.1M.
(2) rotary evaporation being depressurized at 30-40 DEG C after reaction and removing methanol, water is added to be supplemented to original solution volume.
(3) above-mentioned acquired solution is extracted 3 times with isometric ether and ethyl acetate respectively.
(4) through solvent removed by evaporation at reduced pressure after ethyl acetate extraction part being merged, and it is freeze-dried after obtain 1,2, 3,4,6-O- Penta-O-galloyl-D-glucopyranose crude products.
(5) crude product is dissolved with a small amount of methanol, upper sephadex chromatography column, and it is 50% first first to use concentration of volume percent Alcoholic solution (containing 2% formic acid) rinses impurity elimination, then the acetone for being 70% with concentration of volume percent elutes, and collects acetone elution portion Point, it is evaporated under reduced pressure and removes acetone, 1,2,3,4,6-O- Penta-O-galloyl-D-glucopyranose sterlings are obtained after water phase is freeze-dried, are in White powdery solids.
The effect and advantage of the present invention：1,2,3,4,6-O-pentagluacyl glucose standard sample prepared by this method is equal Even property is good, magnitude is accurate, stability is good, to detecting, quantifying for 1,2,3,4,6-O-pentagluacyl glucose content Good standard items are provided.
Description of the drawings
Fig. 1 tannic acid alcoholysis prepares 1,2,3,4,6-O-pentagluacyl glucose process flow chart
Fig. 2 1,2,3,4,6-O-pentagluacyl glucose ESI-MS mass spectrograms (negative ion mode)
The infrared spectrogram of Fig. 3 1,2,3,4,6-O-pentagluacyl glucose
Fig. 4 1,2,3,4,6-O-pentagluacyl glucose1H NMR spectras
Fig. 5 1,2,3,4,6-O-pentagluacyl glucose13C NMR spectras
Fig. 6 uniformity tendency charts
The standard curve of Fig. 7 1,2,3,4,6-O-pentagluacyl glucose standard samples
Fig. 8 radix paeoniae alba extraction HPLC chromatograms detect under 280nm wavelength
Specific implementation mode
This specific embodiment is only the explanation to invention, is not limitation of the present invention, and those skilled in the art are readding Can as needed the present embodiment be made the modification of not creative contribution after this specification by running through, but as long as in the power of the present invention It is all protected by Patent Law in sharp claimed range.
Embodiment 1：
The process flow chart that 1,2,3,4,6-O- Penta-O-galloyl-D-glucopyranose standard samples are prepared using tannic acid alcoholysis is shown in Fig. 1.It weighs tannin acid starting material 25.0g to be placed in 500mL round-bottomed flasks, it is that 70% methanol acetic acid is molten that concentration of volume percent, which is added, In liquid (0.1M, pH 5.0) 20h is reacted in 65 DEG C.After reaction, reacting liquid pH value is adjusted to 6.0 immediately, and at 30 DEG C It depressurizes rotary evaporation and removes methanol, water is added to be supplemented to original solution volume.By above-mentioned acquired solution respectively with isometric ether and Ethyl acetate extracts 3 times.It is chilled dry through solvent removed by evaporation at reduced pressure at 30 DEG C after 3 ethyl acetate extraction parts are merged 1,2,3,4,6-O- Penta-O-galloyl-D-glucopyranose crude products are obtained after dry.Crude product upper sephadex after being dissolved with a small amount of methanol Chromatographic column first uses 500mL concentration of volume percent to be that 50% methanol solution (contain 2% formic acid) rinses impurity elimination, then with 300mL volumes The acetone that percent concentration is 70% elutes, and collects acetone elution fraction, and 30 DEG C are evaporated under reduced pressure removing acetone, and water phase is chilled White powdery solids 1,2,3,4,6-O- Penta-O-galloyl-D-glucopyranose standard samples 3.2g is obtained after drying.Its ESI-MS mass spectrum Figure (negative ion mode) is shown in that Fig. 2, infrared spectrogram are shown in Fig. 3.
Embodiment 2：
It weighs tannin acid starting material 25.0g to be placed in 500mL round-bottomed flasks, it is 70% that 500mL concentration of volume percent, which is added, Methanol acetum (0.1M, pH 5.0) reacts 15h in 65 DEG C.Rotary evaporation is depressurized at 40 DEG C after reaction removes first Alcohol adds water to be supplemented to original solution volume.Above-mentioned acquired solution is extracted 3 times with isometric ether and ethyl acetate respectively.By 3 Through solvent removed by evaporation at reduced pressure at 40 DEG C after secondary ethyl acetate extraction part merging, 1,2,3,4,6-O- is obtained after freeze-dried Penta-O-galloyl-D-glucopyranose crude product.Crude product upper Sephardex LH_20 sephadex chromatographies after being dissolved with a small amount of methanol Column first uses 500mL concentration of volume percent to be that 50% methanol solution (contain 2% formic acid) rinses impurity elimination, then with 300mL volumes hundred Divide the acetone that specific concentration is 70% to elute, collect acetone elution fraction, 40 DEG C are evaporated under reduced pressure removing acetone, and water phase is freeze-dried After obtain 1,2,3,4,6-O-pentagluacyl glucose standard sample 4.1g, white powdery solids.
Embodiment 3：
It weighs tannin acid starting material 25.0g to be placed in 500mL round-bottomed flasks, it is 70% that 500mL concentration of volume percent, which is added, Methanol acetum (0.1M, pH 5.0) reacts 15h in 65 DEG C.Rotary evaporation is depressurized at 40 DEG C after reaction removes first Alcohol adds water to be supplemented to original solution volume.Above-mentioned acquired solution is extracted 3 times with isometric ether and ethyl acetate respectively.By 3 Through solvent removed by evaporation at reduced pressure at 40 DEG C after secondary ethyl acetate extraction part merging, 1,2,3,4,6-O- is obtained after freeze-dried Penta-O-galloyl-D-glucopyranose crude product.Crude product upper Sephardex LH_20 sephadex chromatographies after being dissolved with a small amount of methanol Column first uses 500mL concentration of volume percent to be that 50% methanol solution (contain 2% formic acid) rinses impurity elimination, then with 300mL volumes hundred Divide the acetone that specific concentration is 70% to elute, collect acetone elution fraction, 40 DEG C are evaporated under reduced pressure removing acetone, and water phase is freeze-dried After obtain 1,2,3,4,6-O-pentagluacyl glucose standard sample 4.5g, white powdery solids.
Embodiment 4：The Structural Identification of 1,2,3,4,6-O- Penta-O-galloyl-D-glucopyranoses
1H-NMR(500MHz,methanol-d4)δ:4.42(2H,m,H-6),4.53(1H,m,H-5),5.62(1H,dd, J=1.6,8.4Hz, H-2), 5.64 (1H, t, J=9.6Hz, H-4), 5.93 (1H, t, J=9.6Hz, H-3), 6.27 (1H, d, J=8.4Hz, H-1), 6.93,6.98,7.01,7.08,7.14 (each 2H, s, H-galloyl-2,6)；13C-NMR (100MHz, methanol-d4)δ:61.76(C-6),68.46(C-4),70.83(C-2),72.75(C-3),73.05(C- 5),92.46(C-1), 109.00,109.04,109.12,109.28(each 2C,C-galloyl-2,6),118.37, 118.85,118.89,119.00, 119.69(each 1C,C-galloyl-1),138.62,138.74,138.92, 138.97,139.38(each 1C,C-galloyl-4), 144.89,144.98,145.04,145.07,145.16(each 2C,C-galloyl-3,5),164.85,165.55,165.64, 165.92,166.56(each 1C,C-galloyl-7).On The structure for stating data and document report is almost the same, therefore is accredited as 1,2,3,4,6-O-pentagluacyl glucose.Hydrogen spectrum is shown in figure 4, carbon spectrum is shown in Fig. 5.
Zhang Xiaoyan, Wang Jinhui, chemical constitution study [J] the Shenyang Pharmaceutical Universities journal of Lee milling Radix Paeoniae Albas, 2001,18 (1): 30-32.
Embodiment 5：The uniformity testing of 1,2,3,4,6-O- Penta-O-galloyl-D-glucopyranose standard samples
1. the selection of detection method
Technical basis：The 7th chapters of GB/T15000.3-2008；
Assay method：The purity of HPLC area normalization method bioassay standard samples.
2. the acquisition of detection data
Using random sequence duplicate measurements method, 10 bottles of samples are randomly selected from the sample after packingIt presses Three kinds of programs weigh 3 parts of 1.0mg samples from every bottle respectively, and every part of sample uses 1.0mL methanol to dissolve respectively, carries out HPLC points Analysis, calculates its purity.It is tested using method of analysis of variance, its uniformity is judged.
Data are recorded in table 1.
3. data processing
3.1 trend analysis
Come the trend in prepared by study sample and packing process using the average value of every bottle of content as the function to bottle serial number Logical relation.The result shows that：Trend stability in sample preparation；Dispense uniform, data stabilization (as shown in Figure 6).
3.2 variance analysis
The measurement data of 1 uniformity testing of table
Bottle number Test 1 Test 2 Test 3 Average value
1 99.93 99.90 99.89
2 99.86 99.84 99.89
3 99.89 99.91 99.86
4 99.91 99.91 99.86
5 99.90 99.93 99.88 99.89
6 99.92 99.88 99.91
7 99.88 99.90 99.89
8 99.89 99.88 99.92
9 99.88 99.90 99.88
10 99.91 99.88 99.92
Variance analysis is carried out to above-mentioned data and F is examined, the results are shown in Table 2, table 3.
Average value, variance and the pendulous frequency of every bottle of table 2
Bottle number Average value % Variance Pendulous frequency
1 99.91 0.020817 3
2 99.86 0.025166 3
3 99.89 0.025166 3
4 99.89 0.028868 3
5 99.90 0.025166 3
6 99.90 0.020817 3
7 99.89 0.01 3
8 99.90 0.020817 3
9 99.89 0.011547 3
10 99.90 0.020817 3
The analysis of variance table of 3 uniform Journal of Sex Research of table
Variation source Quadratic sum df It is square F
Between bottle 0.04 9 0.000 1.056
In bottle 0.09 20 0.000
Summation 0.014 29
According to data in table, with v1(i.e. between group)=9 and v2F dividing value tables are looked into (i.e. in group)=20, obtain F0.05(9,20)= 2.94, due to F=1.056<F0.05(9,20) illustrate that 1,2,3,4,6-O-pentagluacyl glucose standard sample is uniform 's.
4. stability test
After sample packing, dry be protected from light is sealed at room temperature.This research was scheduled to last with 3 months, to the 1 of preparation, 2,3, 4,6-O- Penta-O-galloyl-D-glucopyranose standard samples took a sample to examine per two weeks or 1 month, and every part of sample is to measure 5 times Average value be its definite value result.Test result is shown in Table 4.
4 stability test test result of table
In terms of upper table data, the average value measured every time does not change with time in minute and significantly increases Or reduce, by calculate, measured value should and in 99.89% ± 0.014%, which is stable in 3 months.
5. statistical analysis
It will show the class mean in similar subset.
1. harmomic mean sample size=5.000 will be used.
Variance analysis is carried out to above-mentioned data using 19.0 statistical analysis softwares of SPSS and shows F=2.359, P=0.088> 0.05, therefore there was no significant difference for above-mentioned data, which is stable in 3 months.
Embodiment 6：Application of the 1,2,3,4,6-O- Penta-O-galloyl-D-glucopyranoses standard sample in Chinese medicine quality control
Radix Paeoniae Alba derives from the dry root of cohosh Chinese herbaceous peony (Paeonia lactifloria Pall.).With it is calm, Analgesia, anti-inflammatory, liver protection isoreactivity.1,2,3,4,6-O-pentagluacyl glucose is a main active in Radix Paeoniae Alba, It is an important indicator of its quality control.
1. experimental method
The making of 1.1 standard curves
It accurately weighs a certain amount of 1,2,3,4,6-O- Penta-O-galloyl-D-glucopyranoses standard sample and is dissolved in methanol solution and match At the prepare liquid that concentration gradient is 31.25 μ g/mL, HPLC measurement is carried out.HPLC chromatogram condition is：Chromatographic column BDS Hypersil, C18 5 μ, 250mm × 4.6mm；Mobile phase is 60% methanol (containing 0.1% trifluoroacetic acid) solution.10 μ of sample size L；Flow velocity 1mL/min；23 DEG C of column temperature；Detection wavelength 280nm.
The preparation of 1.2 samples to be tested
The ethanol solution ultrasonic extraction 10min of sample 1g 100mL a concentration of 50% after taking Radix Paeoniae Alba to crush, waits for that room temperature is cold But it mends afterwards and adds water to original volume.High performance liquid chromatograph is carried out after filtering to be analyzed.
1.3 sample analysis
The HPLC that sample to be tested is carried out according to above-mentioned PGG standard samples analysis method analyzes detection.
2. experimental result
The standard curve of 1,2,3,4,6-O- Penta-O-galloyl-D-glucopyranose standard samples is shown in Fig. 7.Radix paeoniae alba extraction and 1,2, The HPLC chromatogram of 3,4,6-O- Penta-O-galloyl-D-glucopyranose standard samples is shown in Fig. 8.Radix Paeoniae Alba ethyl alcohol is calculated by external standard method to carry It is 1.8 μ g/mL to take the content of PGG in thing liquid, therefore the content that PGG in white paeony root sample is calculated is 0.18%.

Claims (9)

1. a kind of preparation method and application of 1,2,3,4,6-O-pentagluacyl glucose standard sample, which is characterized in that system Preparation Method includes the following steps：
(1) using tannic acid as material, by tannic acid according to tannic acid: methanol acetum=1: the ratio of 5-20 (g/mL) is molten Solution reacts 15h in methanol acetum in 65 DEG C.Methanol concentration of volume percent is 70% wherein in methanol acetum, dense Degree is the acetic acid of 0.1M.
(2) rotary evaporation being depressurized at 30-40 DEG C after reaction and removing methanol, water is added to be supplemented to original solution volume.
(3) above-mentioned (2) acquired solution is extracted 3 times with isometric ether and ethyl acetate respectively.
(4) through solvent removed by evaporation at reduced pressure after ethyl acetate extraction part being merged, and it is freeze-dried after obtain 1,2,3,4, 6-O- Penta-O-galloyl-D-glucopyranose crude products.
(5) crude product is dissolved with a small amount of methanol, upper sephadex chromatography column, and it is that 50% methanol is molten first to use concentration of volume percent Liquid (containing 2% formic acid) rinses impurity elimination, then the acetone for being 70% with concentration of volume percent elutes, and collects acetone elution fraction, subtracts Pressure evaporation removes acetone, and 1,2,3,4,6-O-pentagluacyl glucose sterling, white powder are obtained after water phase is freeze-dried Last shape solid.
2. according to method of claim 1, which is characterized in that the tannic acid in step (1) is to extract system by raw material of Chinese gall Standby obtained tannic acid.
3. according to method of claim 1, which is characterized in that the reaction temperature in step (1) is 60-65 DEG C, excellent by condition It is 65 DEG C to change final determining optimal reaction temperature.
4. according to method of claim 1, which is characterized in that the reaction time in step (1) is 5-20h, by condition optimizing It is final to determine that optimum reacting time is 15h.
5. according to method of claim 1, which is characterized in that the pH of acetum described in step (2) is 5.0.
6. according to method of claim 1, which is characterized in that extractant described in step (3) is ether and ethyl acetate.
7. according to method of claim 1, which is characterized in that chromatographic column filler used is Sephardex LH-20 in step (5) Sephadex chromatography filler.
8. according to method of claim 1, which is characterized in that acetone soln concentration of volume percent used is in step (5) 70%.
9. according to method of claim 1, it is characterised in that the application in terms of traditional Chinese medicine quality control.
CN201810815957.XA 2017-09-05 2018-07-24 A kind of preparation method of 1,2,3,4,6-O- Penta-O-galloyl-D-glucopyranoses standard sample Pending CN108760948A (en)

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Citations (8)

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