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Planta Med 2001; 67(1): 65-69
DOI: 10.1055/s-2001-10879
Original Paper
Georg Thieme Verlag Stuttgart · New York

Isolation and Frontier Molecular Orbital Investigation of Bioactive Quinone-Methide Triterpenoids from the Bark of Salacia petenensis

William N. Setzer1,*, Michael T. Holland1 , Carey A. Bozeman1 , Glenn F. Rozmus1 , Mary C. Setzer2 , Debra M. Moriarity2 , Sabine Reeb3 , Bernhard Vogler3 , Robert B. Bates4 , William A. Haber5
  • 1 Department of Chemistry, University of Alabama in Huntsville, Huntsville, Alabama, U.S.A.
  • 2 Department of Biological Sciences, University of Alabama in Huntsville, Huntsville, Alabama, U.S.A.
  • 3 Institut für Chemie, Universität Hohenheim, Stuttgart, Germany
  • 4 Department of Chemistry, University of Arizona, Tucson, Arizona, U.S.A.
  • 5 Missouri Botanical Garden, St. Louis, Missouri, U.S.A., Monteverde de Puntarenas, Costa Rica, Central America
Further Information

Publication History

Publication Date:
31 December 2001 (online)

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Abstract

The crude dichloromethane bark extract of Salacia petenensis (Hippocrateaceae) from Monteverde, Costa Rica, shows antibacterial and cytotoxic activity. Bioactivity-directed separation led to the isolation of tingenone and netzahualcoyonol as the biologically active materials. Also isolated from the extract were 3-methoxyfriedel-2-en-1-one (a new natural product) and 29-hydroxyfriedelan-3-one. The structures of these compounds were elucidated on the basis of NMR spectral analysis. Molecular orbital calculations have been carried out using the semi-empirical PM3 and Hartee-Fock 3-21G ab initio techniques on the quinone-methide nortriterpenoids tingenone and netzahualcoyonol, as well as on the nucleotide bases adenine, guanine, cytosine, and thymine. The molecular orbital calculations suggest that a possible mode of cytotoxic action of quinone-methide triterpenoids involves quasi-intercalative interaction of the compounds with DNA followed by nucleophilic addition of the DNA base to carbon-6 of the triterpenoid.

Key words

Salacia petenensis - Hippocrateaceae - cytotoxic - antibacterial - quinone methide - tingenone - netzahualcoyonol - molecular orbital - DNA

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Professor William N. Setzer

Department of Chemistry

The University of Alabama in Huntsville

Huntsville

AL 35899

U.S.A.

Email: wsetzer@matsci.uah.edu

Phone: +1-256-824-6349