Journal article
Unique Polybrominated Hydrocarbons from the Australian Endemic Red Alga Ptilonia australasica
Journal of Natural Products, Vol.79(3), pp.570-577
2016
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. © 2016 The American Chemical Society and American Society of Pharmacognosy.
Details
- Title
- Unique Polybrominated Hydrocarbons from the Australian Endemic Red Alga Ptilonia australasica
- Authors
- Trong D Tran (Author) - Griffith UniversityN B Pham (Author) - Griffith UniversityR J Quinn (Author) - Griffith University
- Publication details
- Journal of Natural Products, Vol.79(3), pp.570-577
- Publisher
- American Chemical Society
- Date published
- 2016
- DOI
- 10.1021/acs.jnatprod.5b00989
- ISSN
- 0163-3864
- Organisation Unit
- School of Science and Engineering - Legacy; University of the Sunshine Coast, Queensland; School of Science, Technology and Engineering; Centre for Bioinnovation
- Language
- English
- Record Identifier
- 99451301402621
- Output Type
- Journal article
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