5-Alkylresorcinols from Hakea amplexicaulis That Cleave DNA

John R. Barr, V. S. Murty, Keiichi Yamaguchi, Shangara Singh, David H. Smith, Sidney M. Hecht

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A dichloromethane extract of Hakea amplexicaulis was found to cause strand scission of ΦX174 replicative form DNA in the presence of Cu(II). Bioassay-guided fractionation of this extract afforded five compounds capable of mediating DNA relaxation. Structure determination of the active principles indicated that they were 5-tridecylresorcinol (1), 5-pentadec-cis-8-enylresorcinol (2), 5-heptadeca-8,11-dienylresorcinol (3), 5-pentadecylresorcinol (4), and 5-heptadec-cis-8-enylresorcinol (5). As noted previously for compounds in this structural series, DNA cleavage was enhanced significantly by incubation under (alkaline) conditions known to promote oxygenation of the parent compounds on the aromatic nucleus.

Original languageEnglish (US)
Pages (from-to)204-207
Number of pages4
JournalChemical Research in Toxicology
Issue number4
StatePublished - Jul 1 1988


ASJC Scopus subject areas

  • Toxicology

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