Bioactive principles in the bark of Pilidiostigma tropicum

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 π−π 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.