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A method for separating 25r- and 25s- epimers of ergostane-type triterpenes

An epimer, ergostane-type technology is applied in the field of splitting ergostane-type triterpenes 25R- and 25S-epimer, and can solve the problem of poor solubility and limitation of ergostane-type triterpenes. High efficiency and cost of separation and purification

Active Publication Date: 2020-01-31
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods all require the use of expensive instruments, and the cost is relatively high
For the most commonly used RP-HPLC preparation method, due to the poor solubility of ergostane-type triterpenes, the sample concentration and injection volume limit the efficiency of separation and purification

Method used

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  • A method for separating 25r- and 25s- epimers of ergostane-type triterpenes
  • A method for separating 25r- and 25s- epimers of ergostane-type triterpenes
  • A method for separating 25r- and 25s- epimers of ergostane-type triterpenes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1. Effects of different organic reagents on the separation of 25R / S-antcin K epimers.

[0030] 1. Experimental materials and methods.

[0031] All chemical reagents mentioned in this method were purchased from Beijing Chemical Plant.

[0032] 25R-antcin K and 25S-antcin K standard curves: Accurately weigh 25R-antcin K and 25S-antcin K reference substances, dissolve in methanol, make 5.00mg / mL mother solution, and dilute step by step with methanol to 2.5, 1, 0.5 ,0.25,0.1,0.05mg / mL concentration, 0.22μm microporous membrane filtration, 10μL injection detection.

[0033] Detection of antcin K crude extract: Weigh 1.00 mg of antcin K crude extract powder, dissolve in 1000 μL methanol, filter through a 0.22 μm microporous membrane, and inject 10 μL for detection.

[0034]Chromatographic conditions:

[0035] Instrument: Agilent 1100 high performance liquid chromatography;

[0036] Chromatographic column: YMC-Pack ODS-A column (5μm, 4.6×250mm);

[0037] Elution p...

Embodiment 2

[0049] Example 2. Effects of different volumes of ethanol on the separation of 25R / S-antcin K epimers.

[0050] 1. Experimental materials and methods.

[0051] Weigh 1g of antcin K crude extract solid powder, add 10, 15, 20, 40, 60mL of ethanol respectively, stir evenly, let stand for 15min, and vacuum filter to dryness. The filter residue was dissolved in methanol and injected for analysis.

[0052] 2. Experimental results

[0053] The experimental results are shown in Table 2 and image 3 . As the volume of ethanol increases, the relative content of 25S-antcin K also increases, but the quality of filter residue decreases and the yield decreases. 15 times the volume of ethanol has a good effect on the separation of antcin K.

[0054] Table 2

[0055]

[0056]

Embodiment 3

[0057] Example 3. Effects of different dissolution times on the separation of 25R / S-antcin K epimers.

[0058] 1. Experimental materials and methods.

[0059] Weigh 10.0 mg of antcin K pure solid powder (relative purity >90%), add 150 μL of ethanol, vortex evenly, let stand, and wait for 20s, 30s, 1min, 2min, 5min, 15min, 30min, 1h, 2h, 4h , 8h, 12h, 24h, 36h, 48h, 72h membrane filtration. The filtrate was diluted 50 times with methanol and injected for analysis.

[0060] 2. Experimental results

[0061] The experimental results are shown in Table 3 and Figure 4 . The relative content of 25R-antcin K in ethanol solution gradually increased with time, but the total dissolved mass of 25R / S-antcin K remained basically unchanged. The relative content of 25R-antcin K in the solution can reach a higher level after 15 minutes of dissolution.

[0062] table 3

[0063]

[0064]

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Abstract

The invention provides a method for splitting 25R- and 25S- ergosterane type triterpene epimers. The method includes: dissolving an isomer mixture sample with an organic solvent of certain volume, and performing filtering, thus acquiring a single epimer with high purity respectively from the filter residue and filtrate. The method provided by the invention splits three pairs of epimers (with a relative content close to 1:1) purified from antrodia camphorate, can acquire 25R-antcin K with relative purity of more than 75%, 25S-antcin K with relative purity of more than 87%, 25R-antcin C with relative purity of 65%, 25S-antcin C with relative purity of 70%, and 25S-antcin H with relative purity of more than 80%. The method utilizes the solubility difference of epomers in specific solvent to achieve the purpose of separation, has the advantages of simple and fast separation process, no need for complex experimental equipment, low cost and no loss, and environmental friendliness, and can be used for mass preparation of 25R- and 25S- epimers.

Description

technical field [0001] The invention relates to a method for splitting 25R- and 25S- epimers of ergostane triterpenes. Taking three pairs of ergostane-type triterpenes 25R / S-antcin K, 25R / S-antcin C and 25R / S-antcin H in Antrodia camphorata as examples, the method utilizes the solubility difference of epimers in specific solvents The separation is achieved, the separation process is simple and fast, no complicated experimental equipment is required and a large amount of 25R- and 25S-isomers with higher purity can be obtained. Background technique [0002] Chirality is a common phenomenon in nature, and many natural products exist mixedly in the form of chiral isomers. With the in-depth study of chiral isomers, it has been found that there are significant differences in the biological activities and chemical properties of many chiral isomers. However, because they have the same planar structure and only differ in stereo configuration, the separation and purification of many...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J9/00
CPCC07B57/00C07B2200/07C07J9/00
Inventor 叶敏匡易李斌乔雪
Owner PEKING UNIV
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