12[beta]-hydroxyandrostane-4,6,8(9),13(14)-tetraene-3,11,16-triketone and application thereof

A technology of hydroxyandrosteroids and triketones, applied in steroidal compounds, medical preparations containing active ingredients, organic chemistry, etc.

Inactive Publication Date: 2013-05-01
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The 12β-hydroxyandrost-4,6,8(9),13(14)-tetraene-3,11,16-trione compound provided by the present invention and its use as an immunosuppressive drug have not been reported yet

Method used

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  • 12[beta]-hydroxyandrostane-4,6,8(9),13(14)-tetraene-3,11,16-triketone and application thereof
  • 12[beta]-hydroxyandrostane-4,6,8(9),13(14)-tetraene-3,11,16-triketone and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010] Example 1: Preparation of 12β-hydroxyandrost-4,6,8(9),13(14)-tetraene-3,11,16-trione

[0011] Take Simao Vine ( Epigynum auritum ) Whole plant dry powder 8.3kg, extracted with ethanol for 3 times, 24 hours each time, concentrated and recovered ethanol to obtain extract after filtering and removing residue, after suspending the extract in water, first extract with petroleum ether to remove low polar components, Carry out extraction with ethyl acetate again, collect ethyl acetate extraction part 150g, carry out crude fractionation with macroporous adsorption resin D101, be elution with the ethanol-water solution of 20%, 35% and 60% respectively with mass percent concentration, collect 60 % ethanol-water eluent, concentrated to get 20 grams of extract, mix the sample with 200-300 mesh silica gel, dry-pack the column and carry out column chromatography, use petroleum ether-acetone (volume ratio is 10:1-1: 1) The two-phase system is the mobile phase for gradient elution, de...

Embodiment 2

[0019] Example 2: 12β-Hydroxyandrosta-4,6,8(9), 13(14)-tetraene-3,11,16-trione immunosuppressive assay

[0020] (1) Preparation of splenocyte suspension

[0021] Healthy Balb / c mice were killed by eyeball bleeding, soaked in 75% alcohol and disinfected for 5 minutes, taken out, placed in a sterile tray with the left side up, and in the ultra-clean bench, use sterilized tweezers to pick up the fur in the middle of the abdomen , make an incision, use another set of instruments to cut open the layers of the abdominal wall, use the third set of instruments to take out the spleen, remove fat and connective tissue, put it in PBS (phosphate buffer saline), wash away the floating blood; then the spleen Move the tissue to a plate containing RPMI 1640 incomplete culture medium, cut it into small pieces with scissors, grind the spleen in a 200-mesh stainless steel screen with a sterile syringe core, wash it with a small amount of PBS several times, and filter to obtain a single cel...

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Abstract

The invention discloses an androstane compound with high polyenoid oxidizability, i.e. 12[beta]-hydroxyandrostane-4,6,8(9), 13(14)-tetraene-3,11,16-triketone. The compound is extracted from epigynum auritum plants. Experiments prove that the compound provided by the invention has immunosuppressive activity.

Description

technical field [0001] The present invention relates to a novel androster compound with high polyene oxidation degree, specifically 12β-hydroxyandrost-4,6,8(9),13(14)-tetraene-3,11,16-trione Compounds and their use as immunosuppressive drugs. Background technique [0002] Simao vine ( Epigynum auritum ) is a species of the genus Simao in the oleander family, which is produced in southern Yunnan. According to our previous research results, Simao contains more novel structures of C 21 Steroids and other compounds. Driven by the interest in discovering new drug lead compounds, we conducted a large number of biological activity screening experiments on these new compounds and found that one of the androsteroids with high saturation and high oxidation degree (12β-hydroxyandroster-4,6,8( 9),13(14)-tetraene-3,11,16-trione) has immunosuppressive activity at a concentration of 40 μg / mL. [0003] Immunosuppression refers to the suppression of immune response. Immunosuppression c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00A61K31/568A61P37/06
Inventor 曹建新姚元成徐琳琳蔡圣宝
Owner KUNMING UNIV OF SCI & TECH
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