Abstract
The crude dichloromethane bark extract of Pilidiostigma tropicum (Myrtaceae) from north Queensland, Australia, shows antibacterial and cytotoxic activity. Bioactivity-directed separation led to the isolation of rhodomyrtoxin B and ursolic acid-3-p-coumarate as the biologically active materials. The structures of these compounds were elucidated on the basis of spectral analysis. The intercalation interaction of rhodomyrtoxin B with DNA was investigated using molecular mechanics and ab initio molecular-orbital techniques. A favorable pi-pi interaction between rhodomyrtoxin B and the cytosine-guanine base pair is predicted, but the orientation of the interaction cannot be predicted based on frontier molecular orbitals.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Amsacrine / chemistry
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Anti-Bacterial Agents / chemistry
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Anti-Bacterial Agents / isolation & purification
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Anti-Bacterial Agents / pharmacology
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Bacillus cereus / drug effects
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Base Pairing
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Benzofurans / chemistry*
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Benzofurans / isolation & purification
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Benzofurans / pharmacology*
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Cell Line, Tumor
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Cytosine / chemistry
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Doxorubicin / chemistry
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Guanine / chemistry
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Humans
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Models, Molecular
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Molecular Conformation
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Myrtaceae / chemistry*
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Plant Bark / chemistry*
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Plant Extracts / chemistry
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Plant Extracts / pharmacology
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Staphylococcus aureus / drug effects
Substances
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Anti-Bacterial Agents
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Benzofurans
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Plant Extracts
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rhodomyrtoxin B
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Amsacrine
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Guanine
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Doxorubicin
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Cytosine