Bromophenols coupled with derivatives of amino acids and nucleosides from the red alga Rhodomela confervoides

J Nat Prod. 2005 May;68(5):691-4. doi: 10.1021/np040234m.

Abstract

Three new bromophenols coupled with pyroglutamic acid derivatives and one bromophenol coupled with deoxyguanosine were obtained from the red alga Rhodomela confervoides. By spectroscopic methods including 2D NMR and single-crystal X-ray structure analysis their structures were elucidated as N-(2,3-dibromo-4,5-dihydroxybenzyl)methyl pyroglutamate (1), N-(2,3-dibromo-4,5-dihydroxybenzyl)pyroglutamic acid (2), N-[3-bromo-2-(2,3-dibromo-4,5-dihydroxybenzyl)-4,5-dihydroxybenzyl]methyl pyroglutamate (3), and 2-N-(2,3-dibromo-4,5-dihydroxybenzylamino)deoxyguanosine (4), respectively. Compounds 1-4 were evaluated against several microorganisms and human cancer cell lines, but found inactive. To our knowledge this is the first report of bromophenols coupled with amino acid or nucleoside derivatives through the C-N bond.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids
  • China
  • Deoxyguanosine / chemistry
  • Drug Screening Assays, Antitumor
  • Humans
  • Hydrocarbons, Brominated / chemistry
  • Hydrocarbons, Brominated / isolation & purification*
  • Hydrocarbons, Brominated / pharmacology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Pyrrolidonecarboxylic Acid / chemistry
  • Rhodophyta / chemistry*
  • Tumor Cells, Cultured

Substances

  • Amino Acids
  • Hydrocarbons, Brominated
  • Deoxyguanosine
  • Pyrrolidonecarboxylic Acid