New lupane bidesmosides exhibiting strong cytotoxic activities in vitro.
Bioorg Chem
; 100: 103868, 2020 07.
Article
em En
| MEDLINE
| ID: mdl-32388425
ABSTRACT
Triterpene bidesmosides are considered as highly cytotoxic saponins, usually less toxic against normal cells than monodesmosides, and less haemolytic. Biological activity of the betulin-type bidesmosides, rarely found in Nature, and seldom prepared due to serious synthetic problems, is poorly recognized. We report herein a protocol for the preparation of disubstituted lupane saponins (betulin bidesmosides) by treatment of their benzoates with potassium carbonate in dichloromethane / methanol solution. Cytotoxicity of all compounds was tested in vitro for a series of cancer cell lines, as well as normal human skin BJ fibroblasts. Presence of l-rhamnose moiety is crucial for cytotoxicity of betulin bidesmosides. On the other hand, l-arabinose fragment connected to lupane C-3 carbon atom significantly decreases activity. Presented results clearly show that betulin bidesmosides have significant clinical potential as anticancer agents.
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Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Triterpenos
/
Antineoplásicos
Tipo de estudo:
Guideline
Limite:
Humans
Idioma:
En
Ano de publicação:
2020
Tipo de documento:
Article