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 Hecht

Research output: Contribution to journalArticle

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Abstract

A dichloromethane extract of Hakea trifurcata that mediated relaxation of ∅X174 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]ben zene (3), 1,3-dihyroxy-5-[14'-(3'',5''-dihydroxyphenyl)tetradecyl]benzene (4), and 1,3-dihydroxy-5-[16'-(3'',5''-dihydroxyphenyl)-cis-8'-hexadecenyl]benz ene (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 - Dec 27 1995
Externally publishedYes

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Benzene
DNA
Bioassay
Methylene Chloride
Dichloromethane
Fractionation
Biological Assay
Derivatives
hakea gibbosa gum

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Lytollis, W., Scannell, R. T., An, H., Murty, V. S., Reddy, K. S., Barr, J. R., & Hecht, S. (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

5-Alkylresorcinols from Hakea trifurcata that cleave DNA. / Lytollis, William; Scannell, Ralph T.; An, Haoyun; Murty, V. S.; Reddy, K. Sambi; Barr, John R.; Hecht, Sidney.

In: Journal of the American Chemical Society, Vol. 117, No. 51, 27.12.1995, p. 12683-12690.

Research output: Contribution to journalArticle

Lytollis, W, Scannell, RT, An, H, Murty, VS, Reddy, KS, Barr, JR & Hecht, S 1995, '5-Alkylresorcinols from Hakea trifurcata that cleave DNA', Journal of the American Chemical Society, vol. 117, no. 51, pp. 12683-12690. https://doi.org/10.1021/ja00156a004
Lytollis W, Scannell RT, An H, Murty VS, Reddy KS, Barr JR et al. 5-Alkylresorcinols from Hakea trifurcata that cleave DNA. Journal of the American Chemical Society. 1995 Dec 27;117(51):12683-12690. https://doi.org/10.1021/ja00156a004
Lytollis, William ; Scannell, Ralph T. ; An, Haoyun ; Murty, V. S. ; Reddy, K. Sambi ; Barr, John R. ; Hecht, Sidney. / 5-Alkylresorcinols from Hakea trifurcata that cleave DNA. In: Journal of the American Chemical Society. 1995 ; Vol. 117, No. 51. pp. 12683-12690.
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