Chemical synthesis and tyrosinase inhibitory activity of rhododendrol glycosides.
Bioorg Med Chem Lett
; 24(1): 122-5, 2014 Jan 01.
Article
in En
| MEDLINE
| ID: mdl-24332496
ABSTRACT
The concise synthesis of rhododendrol glycosides 3-8, which are novel derivatives of (+)-epirhododendrin (1) and (-)-rhododendrin (2), has been achieved in six steps from benzaldehyde 9. The key reactions include aldol condensation and trichloroacetimidate glycosylation. From biological studies, it has been determined that synthetic derivatives of 1 and 2 possess potent tyrosinase inhibitory activity. Particularly, the inhibitory activity of cellobioside 8 (IC50=1.51µM) is six times higher than that of kojic acid. The R-epimers (4, 6, and 8) possessed more potent activity than the corresponding S-epimers (3, 5, and 7), indicating that tyrosinase inhibitory activity is significantly governed by stereochemistry of rhododendrol glycosides.
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Monophenol Monooxygenase
/
Butanols
/
Enzyme Inhibitors
/
Glycosides
Language:
En
Journal:
Bioorg Med Chem Lett
Journal subject:
BIOQUIMICA
/
QUIMICA
Year:
2014
Document type:
Article
Affiliation country:
Japan