Bioactive principles in the bark of Pilidiostigma tropicum.
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.
Setzer
William N
WN
Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL 35899, USA. wsetzer@chemistry.uah.edu
Rozmus
Glenn F
GF
Setzer
Mary C
MC
Schmidt
Jennifer M
JM
Vogler
Bernhard
B
Reeb
Sabine
S
Jackes
Betsy R
BR
Irvine
Anthony K
AK
D000677:Amsacrine / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001409:Bacillus cereus / Q000187:drug effects; D020029:Base Pairing; D001572:Benzofurans / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D003596:Cytosine / Q000737:chemistry; D004317:Doxorubicin / Q000737:chemistry; D006147:Guanine / Q000737:chemistry; D006801:Humans; D008958:Models, Molecular; D008968:Molecular Conformation; D027822:Myrtaceae / Q000737:chemistry*; D024301:Plant Bark / Q000737:chemistry*; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects
D000900:Anti-Bacterial Agents; D001572:Benzofurans; D010936:Plant Extracts; C515961:rhodomyrtoxin B; D000677:Amsacrine; D006147:Guanine; D004317:Doxorubicin; D003596:Cytosine