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25-hydroxy dioscin ketone, and its preparing method and use

A technology of diosgenone and hydroxyl diosgen, which is applied in the application field of 25-hydroxydioscinone, can solve problems such as poor selectivity, and achieve the effect of improving solubility

Inactive Publication Date: 2006-10-25
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The biggest limitation of the chemical synthesis method applied to steroidal compounds is that it has poor selectivity, and it is impossible or difficult to introduce substituents of specific configurations at specific positions. It is precisely because the microbial transformation method is applied to the production of steroidal drugs , which solves the difficulty for organic chemists to synthesize steroid compounds, especially the difficulty of introducing specific functional groups (chemoselectivity and stereoselectivity) at specific positions on some steroid drugs, making industrial production of various steroid hormones a possible, thus laying an important foundation for the development of the steroid pharmaceutical industry

Method used

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  • 25-hydroxy dioscin ketone, and its preparing method and use
  • 25-hydroxy dioscin ketone, and its preparing method and use
  • 25-hydroxy dioscin ketone, and its preparing method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation of 25-hydroxydiosgenone:

[0028] The microorganism used: Streptomyces virginiae IBL-14, the preservation number is CCTCC M206045.

[0029] Streptomyces virginiana was cultured at 29°C to the end logarithmic phase of growth, and diosgenin dissolved in hot ethanol was added at a concentration of 0.4 g / ml to a final concentration of 0.0015 mol / L, transformed for 48 hours, and the reaction was stopped. The volume of ethyl acetate was extracted three times, the extract was concentrated, concentrated under reduced pressure, passed through a silica gel column, and 0.0050 mol of 25-hydroxydiosgenone could be obtained per liter of reaction solution.

[0030] The components and content of the culture medium are as follows:

[0031] Ammonium chloride 3 grams per liter; dipotassium hydrogen phosphate 1.55 grams per liter; sodium dihydrogen phosphate 0.85 grams per liter; glucose 3 grams per liter; yeast powder 3 grams per liter; corn steep liquor 3 grams per liter; cy...

Embodiment 2

[0036] Preparation of 25-hydroxydiosgenone:

[0037] Microorganism used: Streptomyces virginiae, selected from the Culture Collection.

[0038] Streptomyces virginiana was cultured at 29°C to the end logarithmic phase of growth, and diosgenin dissolved in hot ethanol was added at a concentration of 0.4 g / ml to a final concentration of 0.0015 mol / L, transformed for 48 hours, and the reaction was stopped. The volume of ethyl acetate was extracted three times, the extract was concentrated, concentrated under reduced pressure, passed through a silica gel column, and 0.0040 mol of 25-hydroxydiosgenone could be obtained per liter of reaction solution.

[0039] The components and contents of the culture medium are the same as in Example 1.

Embodiment 3

[0041] Preparation of 25-hydroxydiosgenone:

[0042] Microorganisms used: Streptomyces lavendulae, selected from the Culture Collection.

[0043] Streptomyces lavender was cultured at 28°C to the end of logarithmic growth, and diosgenin dissolved in hot ethanol was added at a concentration of 0.4 g / ml to a final concentration of 0.0015 mol / L, transformed for 48 hours, and the reaction was stopped with an equal volume of Ethyl acetate was extracted three times, the extract was concentrated, concentrated under reduced pressure, passed through a silica gel column, and 0.0040 mol of 25-hydroxydiosgenone could be obtained per liter of reaction solution.

[0044] Component and content of culture medium are the same as example 1:

[0045] Identification of the obtained product: colorless needle-like crystals; mp234-236°C; MS (EI) m / z (%): 428 (0.19) (M+, C27H40O4), 397 (66.90), 343 (3.43), 340 (94.49) , 298 (13.63), 283 (2.11), 269 (100.00), 155 (73.85).

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Abstract

The invention discloses a 25-hydroxide radical canaigre soap alkone and the manufacture method and the application. It uses canaigre ssapogenin as raw material to take hydroxylating through streptomycete at 25 tertiary carbon site to gain 25-hydroxide radical canaigre soap alkone. It could be used to make new compound and drug to anti malaria and restrict the growth of tumor.

Description

technical field [0001] The invention belongs to the field of bio-organic chemical industry, and relates to 25-hydroxydiosgenone, a preparation method of 25-hydroxydioscinone and an application of 25-hydroxydioscinone. Background technique [0002] Diosgenin (diosgenin), namely diosgenin, is the product of diosgenin hydrolyzing the 3-position sugar group. With the large-scale screening of natural product active ingredients at home and abroad, it has been discovered that diosgenin and its structural analogues (or derivatives) ) have a wide range of pharmacological activities. For example, diosgenin has broad-spectrum anti-tumor activity; many functions such as cardiovascular activity, such as Di'ao Xinxuekang and Guanxinning, etc., which have been listed in recent years, the main ingredient is diosgenin (yuan); its derivative diosgenin has antimalarial activity, etc. . [0003] In addition, steroid drugs play a very important regulatory function on the body. Since the 1950s...

Claims

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Application Information

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IPC IPC(8): C07J53/00A61K31/58A61P33/06A61P35/00C12P33/20C12R1/465C12R1/56
CPCY02A50/30
Inventor 童望宇魏东芝王风清
Owner EAST CHINA UNIV OF SCI & TECH
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