Idaho sheepherders in the 1950s encountered high rates of cyclopia in newborn lambs. The cause of these birth defects was attributed to cyclopamine, a steroidal alkaloid in Veratrum californicum. Cyclopamine inhibits the Hedgehog (Hh) cell signaling pathway, which is vital for embryonic development, and has been implicated in the progression of some cancers. Extraction of dried and ground V. californium root and rhizome using ethanol yielded at least six unidentified and uncharacterized steroidal alkaloids. We have isolated one of these alkaloids, a suspected isomer of cyclopamine. Mass spectrometery analysis yielded identical mass-to-charge ratios for cyclopamine and the isolated alkaloid. The Hh inhibitory potency of cyclopamine and the novel alkaloid were similar as determined in Shh-Light II cells using a luminescence assay. We present the isolation, bioactivity evaluation and spectroscopic characterization of novel alkaloids using a variety of techniques including circular dichroism spectropolarimetry, mass spectrometry, and nuclear magnetic resonance spectroscopy.

Characterization of steroidal alkaloids isolated from V. californicum

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.