Characterization of Steroidal Alkaloids Isolated From V. californicum
Dr. Owen McDougal
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 constitutional 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.
Watkins, Jeffrey C.; McDougal, Owen; Turner, Matthew; Collins, Joseph; Dirks, Madison; Seale, Jared; and Seppa, Hanna, "Characterization of Steroidal Alkaloids Isolated From V. californicum" (2020). 2020 Undergraduate Research Showcase. 197.