Abstract
The US Southwest plant Dalea parryi (Fabaceae) was investigated as part of an ongoing study of the potential of plant compounds for anthelmintic activity to the human pathogenic hookworm Ancylostoma ceylanicum. This has resulted in the isolation of three previously undescribed isoflavonoid metabolites, denoted parryans A-C, a chalcone, six pterocarpans, and three known compounds from the roots of D. parryi. Parryans A and B express a rarely-seen O-prenyl substituent. Structures of the previously undescribed compounds were established using 1D and 2D NMR spectroscopy and mass spectrometry. The relative and absolute configurations of the undescribed stereoisomers were assigned using chemical shift and coupling constant data and comparisons of specific rotations to published data. The most active of the isolated compounds only expressed a 17% reduction in survival of A. ceylanicum adult hookworm in an ex vivo assay at 50 μg/mL after 5 days exposure. Toxicity, ranging from 47 to 93% reduction in survival of mammalian splenocytes was expressed by four of the compounds.