Planta Med 2012; 78 - PJ124
DOI: 10.1055/s-0032-1321284

Absolute configuration and conformation of brevipolides, cytotoxic compounds from hyptis brevipes

GA Suárez-Ortiz 1, CM Cerda-García-Rojas 2, R Pereda-Miranda 1
  • 1Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, Mexico City, 04510 Mexico
  • 2Departamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, A.P. 14–470, DF 07000 Mexico

The absolute configuration and conformational behavior of the highly flexible natural products brevipolides H and I were ascertained by circular dichroism and X-ray diffraction, in conjunction with a molecular modeling protocol which includes geometry optimization by DFT B3LYP/DGDZVP calculations and comparison between DFT and experimental 1H-1H NMR coupling constants. These results confirmed the biogenetic assumption that the stereogenic center in the final portion of the chain at C-6' of all natural 6-heptenyl-5,6-dihydro-2H-pyran-2-ones from the mint family (Lamiaceae) is always S. Financial Support: CONACyT (104887).

Fig.1: X-ray of brevipolide