Planta Med 2012; 78 - CL14
DOI: 10.1055/s-0032-1320249

Cytotoxic and antibacterial beilschmiedic acids from a gabonese species of Beilschmiedia

RB Williams 1, SM Martin 1, JF Hu 1, VL Norman 1, MG Goering 1, S Loss 2, M O'Neil-Johnson 1, GR Eldridge 1, CM Starks 1
  • 1Lead Discovery and Rapid Structure Elucidation Group, Sequoia Sciences, Inc., 1912 Innerbelt Business Center Drive, St. Louis, MO 63114, USA
  • 2Bruker BioSpin AG, Industriestrasse 26, CH-8117 Fällanden, Switzerland

High-throughput natural products chemistry methods have facilitated the isolation of eight new and two known beilschmiedic acid derivatives from the leaves of a Gabonese species of Beilschmiedia. This class of compounds appears to be unique to two genera of the Lauraceae, and exhibits remarkable structural complexity for a fatty acid. Eight of the compounds were isolated in microgram quantities necessitating the use of a 1.7mm MicroCryoProbe to obtain NMR data, including a complete HMBC, for structure elucidation and dereplication. All of the compounds were screened for cytotoxic activity against NCI-H460 human lung cancer cells and antibacterial activity against a clinical isolate of methicillin-resistant Staphylococcus aureus. Results from enzymatic assays provided evidence that the observed activity was not the result of membrane disruption as one might expect from lipophilic compounds such as these.