Highly Brominated Mono- and Bis-phenols from the Marine Red Alga Symphyocladia latiuscula with Radical-Scavenging Activity
doi: 10.1021/np070061b
pmid: 17602526
Highly Brominated Mono- and Bis-phenols from the Marine Red Alga Symphyocladia latiuscula with Radical-Scavenging Activity
Four new highly brominated and fully substituted mono- and bis-phenols, 1-(2,3,6-tribromo-4,5-dihydroxybenzyl)pyrrolidin-2-one (1), 1,2-bis(2,3,6-tribromo-4,5-dihydroxyphenyl)ethane (2), 6-(2,3,6-tribromo-4,5-dihydroxybenzyl)-2,5-dibromo-3,4-dihydroxybenzyl methyl ether (3), and 2,3,6-tribromo-4,5-dihydroxybenzyl methyl sulfone (4), were characterized from the marine red alga Symphyocladia latiuscula. In addition, five known bromophenols, bis(2,3,6-tribromo-4,5-dihydroxyphenyl)methane (5), bis(2,3,6-tribromo-4,5-dihydroxybenzyl) ether (6), 2,3,6-tribromo-4,5-dihydroxybenzyl methyl ether (7), 2,3,6-tribromo-4,5-dihydroxymethylbenzene (8), and 2,3,6-tribromo-4,5-dihydroxybenzaldehyde (9), were also isolated and identified. The structures of these compounds were elucidated by spectroscopic methods including 1D and 2D NMR as well as by low- and high-resolution mass spectrometric analysis. Structurally, all of these compounds are highly brominated and fully substituted, and contain one or two 2,3,6-tribromo-4,5-dihydroxyphenyl unit(s) in each of the molecules. In addition, compound 4 possesses a unique sulfone structural feature. Each of the isolated compounds was evaluated for alpha,alpha-diphenyl-beta-picrylhydrazyl (DPPH) radical-scavenging activity and all were found to be potent, with IC50 values ranging from 8.1 to 24.7 microM, compared to the known positive control butylated hydroxytoluene (BHT), with an IC50 of 81.8 microM.
- Chinese Academy of Sciences China (People's Republic of)
- Institute of Oceanology China (People's Republic of)
Inhibitory Concentration 50, Molecular Structure, Phenols, Picrates, Biphenyl Compounds, Rhodophyta, Marine Biology, Free Radical Scavengers, Hydrocarbons, Brominated
Inhibitory Concentration 50, Molecular Structure, Phenols, Picrates, Biphenyl Compounds, Rhodophyta, Marine Biology, Free Radical Scavengers, Hydrocarbons, Brominated
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