Bioactivity and Spectroscopic Characterization of a Novel Cyclopamine Isomer Isolated From V. californicum

Document Type

Student Presentation

Presentation Date



College of Arts and Sciences


Department of Chemistry & Biochemistry

Faculty Sponsor

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 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 this novel alkaloid using circular dichroism spectropolarimetry, mass spectrometry, and nuclear magnetic resonance spectroscopy.

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