Abstract
AbstractThe rare phytoecdysteroid canescensterone is a potent activator of both natural and engineered ecdysteroid receptor (EcR) gene‐expression systems. This steroid also shows a remarkable selectivity towards non‐lepidopteran compared with lepidopteran EcRs in gene‐switch assays, a property that makes it a novel candidate lead compound for use in insecticide discovery and gene‐switch design. Canescensterone possesses an unusual ecdysteroid structure, including a pyrrole‐2‐carboxylate group attached to C‐24, a moiety not yet found in any other natural ecdysteroid. We have investigated the ambiguous stereochemistry at C‐24 of this steroid by 1D and 2D solution NMR experiments, which resulted in the assignment of the 24R‐configuration and determination of the side‐chain conformation. The completestereochemical assignment allowed the generation of docking models of canescensterone in both a lepidopteran EcR and a non‐lepidopteran EcR, which helps to explain its selective biological activity.
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