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Senegenin derivative, as well as preparation method and application thereof

A technology of polysapogenin and derivatives, applied in steroids, measuring devices, instruments, etc., can solve the problems of large baseline drift, solvent interference, low sensitivity, etc., and achieve the effect of avoiding absorption detection defects

Inactive Publication Date: 2012-01-04
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the maximum ultraviolet absorption wavelength of polygagenin is 210nm, which belongs to terminal absorption, and there are problems such as large baseline drift, large solvent interference, and low sensitivity during HPLC-UV detection.

Method used

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  • Senegenin derivative, as well as preparation method and application thereof
  • Senegenin derivative, as well as preparation method and application thereof
  • Senegenin derivative, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) Synthesis of Polysapogenin Derivatives

[0027] Weigh 0.1 g of polysapogenin, put it in a flask, add 15 mL of dichloromethane, 5 mL of pyridine, 4 mL of benzoyl chloride, 0.005 g of 4-dimethylaminopyridine, ice-water bath, and stir for 0.5 h to obtain crude polysaccharide derivative. .

[0028] (2) Separation by silica gel column chromatography

[0029] Take the silica gel, accurately weigh it, put it in an evaporating dish, slowly pour the crude polysapogenin derivative solution into the evaporating dish, stir with a glass rod, dry it, and accurately weigh it. Another appropriate amount of silica gel (200-300 mesh) was taken, swelled with petroleum ether-acetone (volume ratio 100:10), and packed into a column.

[0030] Load the sample, and sequentially use petroleum ether-acetone (volume ratios of 100:10, 100:15, 100:20, 100:25, 100:30, 100:35) to elute with a gradient of 3 column volumes each. The fractions of petroleum ether-acetone (volume ratio 100:35) were ...

Embodiment 2

[0037] (1) Synthesis of Polysapogenin Derivatives

[0038] Weigh 0.3 g of polysapogenin, put it in a flask, add 45 mL of dichloromethane, 10 mL of pyridine, 8 mL of benzoyl chloride, 0.005 g of 4-dimethylaminopyridine, stir in an ice-water bath, and stir with a magnetic stirrer for 1 h to obtain the derivative of polysapogenin. Crude goods.

[0039] (2) Separation by silica gel column chromatography

[0040] Weigh an appropriate amount of silica gel, accurately weigh it, place it in an evaporating dish, slowly pour the crude polysapogenin derivative solution into the evaporating dish, stir with a glass rod, dry it, and accurately weigh it. Take an appropriate amount of silica gel (200-300 mesh), swell with petroleum ether-acetone (volume ratio 100:10), and pack the column.

[0041] Load the sample, and sequentially use petroleum ether-acetone (volume ratios of 100:10, 100:15, 100:20, 100:25, 100:30, 100:35) to elute with a gradient of 3 column volumes each. The fractions of...

Embodiment 3

[0048] (1) Synthesis of Polysapogenin Derivatives

[0049] Weigh 0.5 g of polysapogenin, put it in a flask, add 75 mL of dichloromethane, 15 mL of pyridine, 12 mL of benzoyl chloride, 0.01 g of 4-dimethylaminopyridine, stir in an ice-water bath, and stir with a magnetic stirrer for 1 h to obtain the derivative of polysapogenin. Crude goods.

[0050] (2) Separation by silica gel column chromatography

[0051] Weigh an appropriate amount of silica gel, accurately weigh it, place it in an evaporating dish, slowly pour the crude polysapogenin derivative solution into the evaporating dish, stir with a glass rod, dry it, and accurately weigh it. Take an appropriate amount of silica gel (200-300 mesh), swell with petroleum ether-acetone (volume ratio 100:10), and pack the column.

[0052]Load the sample, and sequentially use petroleum ether-acetone (volume ratios of 100:10, 100:15, 100:20, 100:25, 100:30, 100:35) to elute with a gradient of 3 column volumes each. The fractions of ...

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Abstract

The invention provides a senegenin derivative, as well as a preparation method and application thereof. In the senegenin derivative, the molecular formula is C44H52ClO8, and the name is 2,3-diphenyl formyloxy-senegenin. The preparation method comprises the following steps of: adding senegenin, dichloromethane, pyridine, benzoyl chloride and 4-dimethylamino pyridine into a reactor, stirring, and performing an ice water bath reaction; performing silicagel column chromatography and gel column chromatography to the prepared product; separating through semi-preparative high-efficiency liquid-phase chromatography; and collecting eluent of a corresponding chromatographic peak; concentrating in reduced pressure until the eluent is dry to obtain the senegenin derivative pure product with purity of over 98 percent. The pure product serving as a chemical reference substance can be used in content measurement of senegenin, and the ultraviolet maximum absorption wavelength of the senegenin derivative is 230nm and compared with 210nm of senegenin, so that the problems of specificity and stability in HPLC (High Performance Liquid Chromatography)-UV (ultraviolet) detection are solved. Therefore, the senegenin derivative, as well as the preparation method and application have practical values in quality control of the thinleaf milkwort rootbark medicinal material and thinleaf milkwort rootbark set prescription preparation.

Description

technical field [0001] The invention relates to a polysapogenin derivative, in particular to a polysapogenin derivative and a preparation method thereof, as well as the application of the polysapogenin derivative as a chemical reference substance in the determination of polysapogenin content. Background technique [0002] Radix polygalae (Radix polygalae) is a kind of commonly used traditional Chinese medicine, which has the effects of calming the nerves and nourishing the mind, expectorating phlegm, and reducing swelling. The 2010 edition of "Chinese Pharmacopoeia" records its source as Polygala tenuifolia Willd. or Polygala ovalifolia. The dried root of sibirica L.. Polygala saponin is the main chemical component and important active ingredient in Polygala, and senegenin is the hydrochloric acid hydrolyzed aglycone of Polygala saponin, which is often used as an indicator component to evaluate the quality of Polygala, and its structural formula is as follows: [0003] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00G01N30/74
Inventor 秦雪梅李震宇张丽增孙晋鹏邢婕
Owner SHANXI UNIV
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