Antidermatophytic quinolizidine alkaloids from Calpurnia aurea subsp. aurea (Aiton) Benth

From the leaves and stem bark of the Kenyan medicinal plant Calpurnia aurea subsp. aurea, four previously undescribed quinolizidine alkaloids namely, 2β-methoxy-13α-O-(2'-pyrrolylcarbonyl) virgiline, 2α-methoxy-13β-O-(2'-pyrrolylcarbonyl) virgiline, 3α-O-angelate-2β-hydroxy-13α-O-(2'-pyrrolylcarbonyl) virgiline, 2,3-dehydro-virgiline were isolated together with four known ones. Structural elucidation of the compounds was based on 1D and 2D NMR spectroscopy and mass spectrometry. Their relative configurations were determined by NOESY correlations and literature. The quinolizidine alkaloids were tested against Trichophyton rubrum, Trichophyton interdigitale, Trichophyton benhamiae, Microsporum canis and Nannizzia gypsea, common causative agents of most of the tinea infections in human. All the isolated quinolizidine alkaloids exhibited antidermatophytic activity with MIC ranging from 37.5 μg/ml to 300 μg/ml.