5-Alkylresorcinols from Hakea amplexicaulis That Cleave DNA

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

doi:10.1021/tx00004a003

5-Alkylresorcinols from Hakea amplexicaulis That Cleave DNA

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

Research output: Contribution to journal › Article › peer-review

45 Scopus citations

Abstract

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 language	English (US)
Pages (from-to)	204-207
Number of pages	4
Journal	Chemical Research in Toxicology
Volume	1
Issue number	4
DOIs	https://doi.org/10.1021/tx00004a003
State	Published - Jul 1 1988
Externally published	Yes

ASJC Scopus subject areas

Toxicology

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10.1021/tx00004a003

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title = "5-Alkylresorcinols from Hakea amplexicaulis That Cleave DNA",

abstract = "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.",

author = "Barr, {John R.} and Murty, {V. S.} and Keiichi Yamaguchi and Shangara Singh and Smith, {David H.} and Hecht, {Sidney M.}",

year = "1988",

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T1 - 5-Alkylresorcinols from Hakea amplexicaulis That Cleave DNA

AU - Barr, John R.

AU - Murty, V. S.

AU - Yamaguchi, Keiichi

AU - Singh, Shangara

AU - Smith, David H.

AU - Hecht, Sidney M.

PY - 1988/7/1

Y1 - 1988/7/1

N2 - 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.

AB - 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.

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IS - 4

ER -

5-Alkylresorcinols from Hakea amplexicaulis That Cleave DNA

Abstract

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