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Bioactive principles in the bark of Pilidiostigma tropicum

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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.

HF 3-21G(*) optimized structure and numbering scheme of rhodomyrtoxin B

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Acknowledgements

Support for this research was provided in part by a grant from the National Institutes of Health (Grant No. 1 R15 AIOD39740-01). We are grateful to the Queensland Forest Service for allowing us access to the Curtain Fig State Forest. We thank Ms. Susan M. Fields for assistance with the cytotoxicity screening.

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Authors and Affiliations

  1. Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL, 35899, USA

    William N. Setzer, Glenn F. Rozmus, Mary C. Setzer, Jennifer M. Schmidt & Bernhard Vogler

  2. Institut für Chemie, Universität Hohenheim, 70599, Stuttgart, Germany

    Sabine Reeb

  3. School of Tropical Biology, James Cook University, Townsville, Queensland, 4811, Australia

    Betsy R. Jackes

  4. C. S. I. R. O., Tropical Forest Research Centre, Atherton, Queensland, 4883, Australia

    Anthony K. Irvine

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  1. William N. Setzer
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Correspondence to William N. Setzer.

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Dedicated to Professor Dr. Paul von Ragué Schleyer on the occasion of his 75th birthday

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Setzer, W.N., Rozmus, G.F., Setzer, M.C. et al. Bioactive principles in the bark of Pilidiostigma tropicum . J Mol Model 12, 703–711 (2006). https://doi.org/10.1007/s00894-005-0047-1

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