Unique Polybrominated Hydrocarbons from the Australian Endemic Red Alga Ptilonia australasica

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• 作者：Trong D. Tran ; Ngoc B. Pham ; Ronald J. Quinn
• 刊名：Journal of Natural Products
• 出版年：2016
• 出版时间：March 25, 2016
• 年：2016
• 卷：79
• 期：3
• 页码：570-577
• 全文大小：409K
• ISSN：1520-6025

文摘

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 (<b>1b>–<b>3b>) and australasol A (<b>4b>). 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 <b>1b>, <b>2b>, and <b>4b> were determined by quantum chemical ECD calculations employing time-dependent density functional theory. Ptilones A–C (<b>1b>–<b>3b>) show unique 4-ethyl-5-methylenecyclopent-2-enone (<b>1b> and <b>2b>) and 2-methyl-6-vinyl-4H-pyran-4-one (<b>3b>) skeletons not previously reported in algal metabolites. Ptilone A displayed the most potent cytotoxicity against the human prostate cancer PC3 cells with an ICb>50b> value of 0.44 μM and induced the PC3 cell cycle arrest in the G0/G1 phase.