The structure of hildecarpin, an insect antifeedant 6a-hydroxypterocarpan isolated from the roots of Tephrosia hildebrandtii has been confirmed by a combination of degradation reactions, NMR and mass spectra. Hildecarpin has been dehydrated to the corresponding pterocarpene 3-hydroxy-2-methoxy-8,9-methylenedioxypterocarpene. Hydrogenation and hydrogenolysis of the pterocarpene has afforded the isoflavan 2′, 7-dihydroxy-6-methoxy-4′,5′-methylenedioxyisoflavan, acetylation of which has led to 2′, 7-diacet6xy-6-methoxy-4′,5′-methylenedioxyisoflavan. The NMR and mass spectra of the degradation products confirm the structure previously assigned to hildecarpin.

A new 6a-hydroxylated pterocarpan, named hildecarpin, has been isolated from the healthy roots of Tephrosia hildebrandtii. It has been assigned the structure (−)-3, 6a-dihydroxy-2-methoxy-8, 9-methylenedioxypterocarpan on the basis of its spectroscopie data, optical rotation and chemical transformations. Hildecarpin has exhibited insect antifeedant activity against the legume pod-borer Maruca testulalis, an important pest of the cowpea (Vigna unguiculata), and antifungal activity against Cladosporium cucumerinum. This finding suggests that the pterocarpan phytoalexins formed as a result of microbial infection of the cowpea plant may constitute a basis for induced resistance in the plant against M. testulalis.