Antibacterial Hydroxycinnamic Esters from Piper caninum from Paluma, North Queensland, Australia. The Crystal and Molecular Structure of (+)-Bornyl Coumarate

William N. Setzer; Mary C. Setzer; Robert B. Bates; Pichaya Nakkiew; Betsy R. Jackes; Liqing Chen; Michael B. McFerrin; Edward J. Meehan

doi:10.1055/s-2006-960855

Planta Med 1999; 65(8): 747-749
DOI: 10.1055/s-2006-960855

Letters

Antibacterial Hydroxycinnamic Esters from Piper caninum from Paluma, North Queensland, Australia. The Crystal and Molecular Structure of (+)-Bornyl Coumarate

William N. Setzer¹ , Mary C. Setzer² , Robert B. Bates³ , Pichaya Nakkiew³ , Betsy R. Jackes⁴ , Liqing Chen⁵ , Michael B. McFerrin⁵ , Edward J. Meehan⁵

¹Department of Chemistry, The University of Alabama in Huntsville, Huntsville, Alabama, U.S.A.
²Department of Biological Sciences, The University of Alabama in Huntsville, Huntsville, Alabama, U.S.A
³Department of Chemistry, The University of Arizona, Tucson, Arizona, U.S.A.
⁴Department of Tropical Plant Science, James Cook University, Townsville, Queensland, Australia
⁵Laboratory for Structural Biology, The University of Alabama in Huntsville, Huntsville, Alabama, U.S.A.

Abstract

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Abstract

The crude chloroform bark extract of Piper caninum (Piperaceae) exhibits antibacterial activity against the Gram-positive bacteria, Bacillus cereus, Staphylococcus aureus, and Streptococcus pneumoniae. The antibacterial agents in this extract have been isolated using bioactivity-directed chromatographic techniques and identified by NMR spectroscopy as (+)-bornyl p-coumarate and bornyl caffeate. A single-crystal X-ray structure has been carried out on (+)-bornyl p-coumarate. The compound crystallizes in the orthorhombic space group P2₁2₁2₁ (#19) with a = 12.659(4), b = 13.281(4), and c = 10.177(3) Å. Fullmatrix least-squares refinement converged at R = 0.047, and R_w = 0.058.

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