Method for preparing optically pure L-goitrin and D-goitrin by adopting liquid chromatogram and chiral separation analytical method

A technique for liquid chromatography and expressing Yichun, which is applied in the fields of preparing optically pure Glycin and expressing Yichun and chiral separation and analysis by liquid chromatography.

Inactive Publication Date: 2009-06-03
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Since the physiological effects of D-goitrin and L-goitrin are quite different, and there is no chiral separation of DL-goitrin or L-goitrin extracted from Radix Isatidis purification process

Method used

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  • Method for preparing optically pure L-goitrin and D-goitrin by adopting liquid chromatogram and chiral separation analytical method
  • Method for preparing optically pure L-goitrin and D-goitrin by adopting liquid chromatogram and chiral separation analytical method
  • Method for preparing optically pure L-goitrin and D-goitrin by adopting liquid chromatogram and chiral separation analytical method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Preparation of Optically Pure L-goitrin and D-goitrin Using SHISEIDO CD-PH Analytical Column

[0042] 1. Instruments and Materials

[0043] Reagents: n-hexane, ethanol (Shanghai Zhenxing Factory, analytical grade); DL-goitrin standard sample (Acros Organics Company, >99%).

[0044] Instruments: Waters 600 pump, waters 486 dual-wavelength ultraviolet detector, Junrui chromatographic workstation; CD-PH column (SHISEIDO, 250*4.6mm); rotary evaporator (Shanghai Yuhua Instrument Co., Ltd.); circulating water pump (Shanghai Yuhua Instrument Co., Ltd.); Kang Kejiao Instrument Equipment Co., Ltd.); Jasco P-1000 series digital automatic polarimeter (JASCO Japan).

[0045] 2. Preparation method

[0046] Dissolve 30mg of DL-goitrin standard sample in 15ml of ethanol. Separation with analytical SHISEIDO CD-PH column (250*4.6mm), high performance liquid chromatography conditions: mobile phase adopts n-hexane-ethanol system (70 / 30, v / v), flow rate is 1.0ml / min, detection wavelengt...

Embodiment 2

[0049] Preparation of optically pure L-goitrin and D-goitrin with SHISEIDO CD-PH semi-preparative column

[0050] 1. Instruments and Materials

[0051] Reagents: n-hexane, ethanol (Shanghai Zhenxing Factory, analytical grade); DL-goitrin standard sample (Acros Organics Company, >99%).

[0052] Instruments: Waters 600 pump, waters 486 dual-wavelength ultraviolet detector, Junrui chromatographic workstation; CD-PH column (SHISEIDO, 250*9.4mm); rotary evaporator (Shanghai Yuhua Instrument Co., Ltd.); circulating water pump (Shanghai Yuhua Instrument Co., Ltd.); Kang Kejiao Instrument Equipment Co., Ltd.).

[0053] 2. Preparation method

[0054] Dissolve 120mg of DL-goitrin standard sample in 60ml of ethanol. Separation with preparative SHISEIDO CD-PH semi-preparative column (250*9.4mm), liquid chromatography conditions: mobile phase adopts n-hexane-ethanol system (70 / 30, v / v), flow rate is 4.0ml / min, detection The wavelength is 244nm. Inject 1ml each time, and collect fracti...

example 3

[0056] Preparation of Optically Pure L-goitrin and D-goitrin Using DAICEL CHIRALPAK AD-RH Analytical Column

[0057] 1. Instruments and Materials

[0058] Reagents: Methanol (Merck, chromatographically pure); the mobile phase and the water used for preparing the solution are Watsons distilled water; DL-goitrin standard sample (Acros Organics Company, >99%).

[0059] Instruments: Waters 600 pump, waters 486 dual-wavelength ultraviolet detector; Millenium 32 workstation; CHIRALPAK AD-RH column (Daicel Chemistry Industry, 150*4.6mm); rotary evaporator (Shanghai Yuhua Instrument Co., Ltd.); circulating water pump ( Shanghai Yukang Science and Education Equipment Co., Ltd.).

[0060] 2. Preparation method

[0061] Dissolve 30mg of DL-goitrin standard sample in 4ml of distilled water. With CHIRALPAKAD-RH column (Daicel Chemistry Industry, 150*4.6mm), high-performance liquid chromatography conditions are: mobile phase adopts methanol-water system (30 / 70, v / v), flow rate is 1.0ml / m...

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Abstract

The invention relates to a method for preparing optically pure L-goitrin and D-goitrin by adopting liquid chromatogram and a chiral separation analytical method; the method comprises the following steps: a. DL-goitrin is prepared into solution; b. the liquid chromatogram by adopting chiral stationary chromatogram column based on polysaccharide derivative or the chiral stationary chromatogram column based on cyclodextrin derivative is separated, and flowing components of the L-goitrin and the D-goitrin, corresponding to spectral bands, are respectively on-line collected, the operation is repeated until collecting the required amount; c. solvent in eluant of the corresponding spectral bands of the L-goitrin and the D-goitrin, collected in the step b, is evaporated, thus obtaining the optically pure L-goitrin and D-goitri. The invention provides a chiral separation analytical method of the L-goitrin and the D-goitrin.

Description

technical field [0001] The invention relates to a preparation method and a chiral separation and analysis method of optically pure L-goitrin and D-goitrin. Background technique [0002] Biaogaoyichun is an alkaloid that can be extracted from Radix Radix and has anti-influenza virus effects (People's Republic of China Invention Patent 200410016902.0). Invention patent 200410016902.0 provides the method and application of extracting Yichun from Radix isatidis. However, there is a chiral center in the chemical structure of D-goitrin, and there is a chiral isomer L-goitrin in D-goitrin. L-goitrin, also known as thyrotoxin, has the effect of causing goiter (E.B. Astwood. Journal of Biological Chemistry, 1949, 181, 121). Using the method of the invention patent 200410016902.0, the chiral structure of Biaoyichun extracted from Radix Radix Radix was not involved. Although the chemical structure diagram attached to the patent showed D type, no relevant data was provided. [0003] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/16
Inventor 许旭马东杰
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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