Bromophenols Coupled with Methyl γ-Ureidobutyrate and Bromophenol Sulfates from the Red Alga Rhodomela confervoides

Journal of Natural Products
2006.0

Abstract

Four new bromophenols C-N coupled with methyl gamma-ureidobutyrate (1-4), a phenylethanol bromophenol (5), and three phenylethanol sulfate bromophenols (6-8) have been isolated from polar fractions of an ethanolic extract of the red alga Rhodomela confervoides. On the basis of spectroscopic evidence including HRMS and 2D NMR data, the structures of the new compounds were determined as methyl N'-(2,3-dibromo-4,5-dihydroxybenzyl)-gamma-ureidobutyrate (1), methyl N,N'-bis(2,3-dibromo-4,5-dihydroxybenzyl)-gamma-ureidobutyrate (2), methyl N'-[3-bromo-2-(2,3-dibromo-4,5-dihydroxybenzyl)-4,5-dihydroxybenzyl]-gamma-ureidobutyrate (3), methyl N'-(2,3-dibromo-4,5-dihydroxybenzyl)-N'-[3-bromo-2-(2,3-dibromo-4,5-dihydroxybenzyl)-4,5-dihydroxybenzyl]-gamma-ureidobutyrate (4), 2,3-dibromo-4,5-dihydroxyphenylethanol (5), 2,3-dibromo-4,5-dihydroxyphenylethanol sulfate (6), 3-bromo-4,5-dihydroxyphenylethanol sulfate (7), and 3-bromo-2-(2,3-dibromo-4,5-dihydroxybenzyl)-4,5-dihydroxyphenylethanol sulfate (8). The cytotoxicity of all compounds was evaluated against several human cancer cell lines including human colon cancer (HCT-8), hepatoma (Bel7402), stomach cancer (BGC-823), lung adenocarcinoma (A549), and human ovarian cancer (A2780). Among them, the phenylethanol and the phenylethanol sulfate bromophenols (5-8) showed moderate cytotoxicity against all tested cell lines.

Knowledge Graph

Similar Paper

Bromophenols Coupled with Methyl γ-Ureidobutyrate and Bromophenol Sulfates from the Red Alga <i>Rhodomela </i><i>c</i><i>onfervoides</i>
Journal of Natural Products 2006.0
Bromophenols Coupled with Methyl γ-Ureidobutyrate and Bromophenol Sulfates from the Red Alga <i>Rhodomela </i><i>c</i><i>onfervoides</i>
Journal of Natural Products 2006.0
Bromophenol Derivatives from the Red Alga <i>Rhodomela </i><i>c</i><i>onfervoides</i>
Journal of Natural Products 2004.0
Bromophenols from the Red Alga <i>Rhodomela </i><i>c</i><i>onfervoides</i>
Journal of Natural Products 2003.0
Bromophenols Coupled with Derivatives of Amino Acids and Nucleosides from the Red Alga <i>Rhodomela </i><i>c</i><i>onfervoides</i>
Journal of Natural Products 2005.0
Bromophenols Coupled with Derivatives of Amino Acids and Nucleosides from the Red Alga <i>Rhodomela </i><i>c</i><i>onfervoides</i>
Journal of Natural Products 2005.0
Bromophenols Coupled with Nucleoside Bases and Brominated Tetrahydroisoquinolines from the Red Alga <i>Rhodomela confervoides</i>
Journal of Natural Products 2007.0
Isolation, Characterization, and Antioxidant Activity of Bromophenols of the Marine Red Alga <i>Rhodomela confervoides</i>
Journal of Agricultural and Food Chemistry 2011.0
Isolation, Characterization, and Antioxidant Activity of Bromophenols of the Marine Red Alga <i>Rhodomela confervoides</i>
Journal of Agricultural and Food Chemistry 2011.0
Natural bromophenols from the marine red alga Polysiphonia urceolata (Rhodomelaceae): Structural elucidation and DPPH radical-scavenging activity
Bioorganic &amp; Medicinal Chemistry 2007.0