5-Alkylresorcinols from Hakea trifurcata That Cleave DNA

William Lytollis, Ralph T. Scannell, Haoyun An, V. S. Murty, K. Sambi Reddy, John R. Barr, Sidney M. Hecht

Research output: Contribution to journalArticle

69 Scopus citations

Abstract

A dichloromethane extract of Hakea trifurcata that mediated relaxation of ϕX174 replicative form DNA at micromolar concentrations in the presence of Cu2+ was resolved into six active components by bioassay-guided fractionation. Five of the active principles were characterized structurally and shown to be 5-alkylresorcinol derivatives. These included 1,3-dihydroxy-5-tridecylbenzene (1), 1,3-dihydroxy-5-(cis-8’-pentadecenyl)benzene (2), 1,3-dihydroxy-5-[14‘-(3“,5”-dihydroxyphenyl)-cis-6’-tetradecenyl]benzene (3), 1,3-dihyroxy-5-[14‘-(3“,5”-dihydroxyphenyl)tet-radecyl]benzene (4), and 1,3-dihydroxy-5-[16‘-(3“, 5”-dihydroxyphenyl)-cis-8‘-hexadecenyl]benzene (5). The structures of these five natural principles were confirmed by total synthesis; compounds 1—5 were accessible from 3,5-dimethoxybenzaldehyde in overall yields of 59%, 27%, 15%, 16%, and 13%, respectively.

Original languageEnglish (US)
Pages (from-to)12683-12690
Number of pages8
JournalJournal of the American Chemical Society
Volume117
Issue number51
DOIs
StatePublished - Jan 1 1995

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Lytollis, W., Scannell, R. T., An, H., Murty, V. S., Reddy, K. S., Barr, J. R., & Hecht, S. M. (1995). 5-Alkylresorcinols from Hakea trifurcata That Cleave DNA. Journal of the American Chemical Society, 117(51), 12683-12690. https://doi.org/10.1021/ja00156a004