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5-Alkylresorcinols from Hakea amplexicaulis that cleave DNA
J R Barr1, V S Murty, K Yamaguchi
1Department of Chemistry, University of Virginia, Charlottesville 22901.
Chemical Research in Toxicology
|July 1, 1988
Summary
This study identified five compounds from Hakea amplexicaulis that can break DNA strands, especially under alkaline conditions that promote oxygenation. These natural compounds show potential for DNA-damaging applications.
Area of Science:
- Natural Product Chemistry
- Molecular Biology
- Biochemistry
Background:
- The plant Hakea amplexicaulis produces extracts with DNA-damaging properties.
- Copper(II) ions are known to facilitate DNA cleavage by certain compounds.
Purpose of the Study:
- To isolate and identify compounds from Hakea amplexicaulis responsible for DNA strand scission.
- To investigate the structure-activity relationship of these compounds in mediating DNA relaxation.
Main Methods:
- Dichloromethane extraction of Hakea amplexicaulis.
- Bioassay-guided fractionation to isolate active compounds.
- Structure determination using spectroscopic methods.
- DNA strand scission assays in the presence of Cu(II) and under alkaline conditions.
Main Results:
- Five alkylresorcinols were isolated: 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).
- All five compounds mediated DNA relaxation (strand scission) of phi X174 replicative form DNA in the presence of Cu(II).
- DNA cleavage activity was significantly enhanced under alkaline conditions, which promote compound oxygenation.
Conclusions:
- Hakea amplexicaulis contains alkylresorcinols with DNA strand scission activity.
- The DNA-damaging mechanism involves Cu(II) and is enhanced by alkaline-induced oxygenation.
- These findings contribute to understanding the bioactivity of Hakea amplexicaulis constituents.