Dibenzyl bromophenols with diverse dimerization patterns from the brown alga Leathesia nana

J Nat Prod. 2004 Oct;67(10):1661-6. doi: 10.1021/np0400609.

Abstract

Six novel dibenzyl bromophenols (1-6) with different dimerization patterns and two propyl bromophenol derivatives (7 and 8), together with 11 known bromophenol derivatives, were isolated from the ethanolic extract of the brown alga Leathesia nana. On the basis of spectroscopic methods the structures of the new compounds were determined as 5,6'-diethyloxymethyl-3,4,2'-tribromo-2,3',4'-trihydroxydiphenyl ether (1), 2-(2,3-dibromo-4,5-dihydroxybenzyl)-3,5-dihydroxy-4-methoxybenzyl alcohol (2), 6-(2,3-dibromo-4,5-dihydroxybenzyl)-2,3-dibromo-4,5-dihydroxy benzyl methyl ether (3), 9,10-dihydro-9,10-dimethoxy-3,4,7,8-tetrabromo-1,2,5,6-tetrahydroxyanthracene (4), (+)-3-(2,3-dibromo-4,5-dihydroxyphenyl)-4-bromo-5,6-dihydroxy-1,3-dihydroisobenzofuran (5), rel-(4aS,10aR)-(+/-)-6,7-dibromo-4a-hydroxy-3,8-dihydroxymethyl-10a-methoxy-1,4,4a,10a-tetrahydrodibenzo[b,e][1,4]dioxin-1-one (6), (E)-2-methyl-3-(2,3-dibromo-4,5-dihydroxyphenyl)propenal (7), and 2-methyl-3-(2,3-dibromo-4,5-dihydroxyphenyl)-1-propanol (8). Some compounds including 3 showed in vitro selective cytotoxicity against several human cancer cell lines. This is the first brown alga to be reported containing bromophenols.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • China
  • Crystallography, X-Ray
  • Dimerization
  • Drug Screening Assays, Antitumor
  • Humans
  • Hydrocarbons, Brominated / chemistry*
  • Hydrocarbons, Brominated / isolation & purification
  • Hydrocarbons, Brominated / pharmacology
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Phaeophyceae / chemistry*
  • Phenols / chemistry*
  • Phenols / isolation & purification
  • Phenols / pharmacology
  • Stereoisomerism
  • Tumor Cells, Cultured

Substances

  • Hydrocarbons, Brominated
  • Phenols