Unique Polybrominated Hydrocarbons from the Australian Endemic Red Alga Ptilonia australasica.
J Nat Prod
; 79(3): 570-7, 2016 Mar 25.
Article
em En
| MEDLINE
| ID: mdl-26904921
ABSTRACT
The red alga Ptilonia australasica is endemic to Australian temperate waters. Chemical investigation of P. australasica led to the identification of four new polybrominated compounds, ptilones A-C (1-3) and australasol A (4). Their planar structures were established by extensive NMR and MS analyses. The low H/C ratio and the presence of a large number of heteroatoms made the structure elucidation challenging. The absolute configurations of 1, 2, and 4 were determined by quantum chemical ECD calculations employing time-dependent density functional theory. Ptilones A-C (1-3) show unique 4-ethyl-5-methylenecyclopent-2-enone (1 and 2) and 2-methyl-6-vinyl-4H-pyran-4-one (3) skeletons not previously reported in algal metabolites. Ptilone A displayed the most potent cytotoxicity against the human prostate cancer PC3 cells with an IC50 value of 0.44 µM and induced the PC3 cell cycle arrest in the G0/G1 phase.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Rodófitas
/
Hidrocarbonetos Bromados
/
Antineoplásicos
Limite:
Humans
/
Male
País/Região como assunto:
Oceania
Idioma:
En
Ano de publicação:
2016
Tipo de documento:
Article