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Saponin derivatives and uses thereof

A technology of derivatives and saponins, applied in furostane-type saponin derivatives, the application field in the prevention and treatment of depression, can solve the problems of no depression, rare relationship between chemical structure and pharmacodynamic mechanism, etc.

Active Publication Date: 2015-09-09
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far no new traditional Chinese medicine for the treatment of depression has been marketed, and there are few research reports on the relationship between chemical structure and pharmacodynamic mechanism in this regard

Method used

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  • Saponin derivatives and uses thereof
  • Saponin derivatives and uses thereof
  • Saponin derivatives and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Example 1 Preparation of furostane-type saponin monosaccharide derivatives

[0075]

[0076] To prepare furostane-type saponins monosaccharide derivatives with timosaponin B-III as the reaction starting material, the specific steps are as follows:

[0077] (1) Dissolve 0.05mol Zhimu Saponin B-Ⅲ in 300ml methanol solution (water or 30v / v% ethanol solution or 1w / v% Tween solution) with a volume ratio of 10v / v%, and add 0.5ml-1ml Concentrated sulfuric acid, react at 80°C-150°C for 1 hour to 6 hours.

[0078] (2) Adjust the pH of the above reaction solution to 6-7 with sodium hydroxide.

[0079] (3) Use 900ml-1200ml n-butanol to extract the solution obtained after neutralization in step (2) for 3 times, and concentrate the extract under reduced pressure to evaporate to dryness.

[0080] (4) After dissolving the above solid with water and adsorbing the saponin on the ODS column, eluting with 40v / v%-60v / v% methanol, collect the eluate.

[0081] (5) Recover the solution under reduced pr...

Embodiment 2

[0082] Example 2 Preparation of furostane-type saponin derivatives

[0083]

[0084] (1) Dissolve 0.05mol Anemarrhena saponin B-Ⅲ in 300mL methanol solution (water or 30% ethanol solution or 1% Tween solution) with a volume ratio of 10%, add 2mL-4mL concentrated hydrochloric acid, 80-150℃ React for 1 hour to 6 hours.

[0085] (2) Adjust the pH of the above reaction solution to 6-7 with sodium hydroxide.

[0086] (3) Use 900mL-1200mL n-butanol to extract the solution obtained after step (2) neutralization for 3 times, and concentrate the extract under reduced pressure until it is evaporated to dryness.

[0087] (4) After dissolving the above solid with water and adsorbing the saponin on the ODS column, eluting it with 40v / v%~60v / v% methanol, collect the eluate.

[0088] (5) Recover the solution under reduced pressure and evaporate to dryness to obtain furostane-type saponin monosaccharide derivative 2 (NMR: see Table 1 for details).

Embodiment 3

[0089] Example 3 Preparation of furostane-type saponin monosaccharide derivatives

[0090]

[0091] To prepare furostane-type saponins monosaccharide derivatives with timosaponin B-III as the reaction starting material, the specific steps are as follows:

[0092] (1) Dissolve 0.1 mol Zhimu Saponin B-III in 600ml methanol solution with a volume ratio of 10v / v%, add 30ml-50ml concentrated hydrochloric acid, and react at 80℃-100℃ for 2 hours.

[0093] (2) Adjust to pH=6-7 with sodium hydroxide.

[0094] (3) Use 1.8L-2.4L of n-butanol to extract the solution obtained after neutralization in step (2) for 3 times, and concentrate the extract under reduced pressure to evaporate to dryness.

[0095] (4) After dissolving the above solid with water and adsorbing the saponin on the ODS column, eluting with 40v / v%-60v / v% methanol, collect the eluate.

[0096] (5) Recover the solution under reduced pressure, and evaporate to dryness to get the aglycon 3 of mother saponin B-III (NMR: 30.63(1-C); 27.14...

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PUM

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Abstract

A saponin derivative, the structure thereof is as represented by formula (I). Animal experimentation proves that the saponin derivative is provided with significant antidepressant pharmacological activity, can be used as an active ingredient to be prepared into a medicament, food, or healthcare product, and, either separately or in conjunction with other substances, can be used for preventing and treating depression.

Description

Technical field [0001] The present invention relates to a saponin derivative, in particular to a furostane type saponin derivative, and the application of the derivative in the prevention and treatment of depression. Background technique [0002] Anemarrhena asphodeloides (anemarrhena asphodeloides) is the dry rhizome of the Liliaceae plant Anemarrhena asphodeloides. According to the records in "Flora", its sex is bitter and cold, has the effect of nourishing yin and reducing fire, moisturizing dryness and smoothing intestines, and improving bowel movements. [0003] The main chemical components of Chinese herbal medicine Anemarrhena are steroidal saponins, diphenylpyrones, polysaccharides and lignins, such as: Timosaponin A-Ⅰ, A-Ⅱ, A- Ⅲ, A-IV, B-I, B-II and B-III, among them, the structure of timosaponin A-II and A-IV is still unknown. And anemarsaponin (amemarsaponin) A2, namely Marcosaponin-3-O-β-D-glucopyranosyl (1→2)-β-D-galactopyranoside B (marlogenin-3-O- β-D-glucopyranos...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J71/00A61K31/7048A61K31/58A61K31/665A61P25/24A23L1/30
CPCC07G3/00C07H15/26C07J71/00A61K36/8964A61P25/24C07J71/0005
Inventor 黄成钢吴斌范明松李志雄孙兆林陈明苍
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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