Synthesis of Lanostane-Type Triterpenoid N-Glycosides and Their Cytotoxicity against Human Cancer Cell Lines.
Chem Biodivers
; 15(7): e1800113, 2018 Jul.
Article
en En
| MEDLINE
| ID: mdl-29734526
ABSTRACT
Seventeen lanostane-type triterpenoid derivatives (2 - 18), including 11N-glycosides (8 - 18), were synthesized from the natural triterpenoid, lanosterol (1), and were evaluated for their cytotoxicity against the human cancer cell lines, HL-60, A549, and MKN45, as well as the normal human lung cells, WI-38. Among them, N-ß-d-2-acetamido-2-deoxyglucoside (10) showed cytotoxicity against HL-60, A549, MKN45, and WI-38 cells (IC50 0.0078 - 2.8 µm). However, N-ß-d-galactoside (12) showed cytotoxicity against HL-60 and MKN45 cells (IC50 0.0021 - 4.0 µm), but not the normal WI-38 cells. Furthermore, Western blot analysis suggested that 12 induces apoptosis by activation of caspases-3, 8, and 9. These results will be useful for the synthesis of other tetracyclic triterpenoids or steroid N-glycosides to increase their cytotoxicity and apoptosis-inducing activities.
Palabras clave
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Triterpenos
/
Glicósidos
/
Lanosterol
/
Antineoplásicos Fitogénicos
Límite:
Humans
Idioma:
En
Revista:
Chem Biodivers
Asunto de la revista:
BIOQUIMICA
/
QUIMICA
Año:
2018
Tipo del documento:
Article
País de afiliación:
Japón