Cyclopamine bioactivity by extraction method from Veratrum californicum

Isolation, purification, and full NMR assignments of cyclopamine from Veratrum californicum

BACKGROUND The Hedgehog signaling pathway is essential for embryogenesis and for tissue homeostasis in the adult. However, it may induce malignancies in a number of tissues when constitutively activated, and it may also have a role in other forms of normal and maladaptive growth. Cyclopamine, a naturally occurring steroidal alkaloid, specifically inhibits the Hedgehog pathway by binding directl...

A Cyclopian Fetus Resulting from Oral Ingestion of Veratrum californicum

The teratogenic Veratrum alkaloid cyclopamine inhibits sonic hedgehog signal transduction.

The steroidal alkaloid cyclopamine produces cyclopia and holoprosencephaly when administered to gastrulation-stage amniote embryos. Cyclopamine-induced malformations in chick embryos are associated with interruption of Sonic hedgehog (Shh)-mediated dorsoventral patterning of the neural tube and somites. Cell types normally induced in the ventral neural tube by Shh are either absent or appear ab...

Synthesis of cyclopamine using a biomimetic and diastereoselective approach.

 Isolated from corn lily Veratrum californicum.  Ingestion of the corn lily (Veratrum californicum) by pregnant sheep caused the birth of lambs with cyclopia. The Veratrum alkaloid cyclopamine was identified as the causative agent. It is very expensive commercially (~$10/mg), No total synthesis is available in literature after 50 year of its isolation. Inhibition of Hh signaling provides a ro...

From teratogens to potential therapeutics: natural inhibitors of the Hedgehog signaling network come of age.

Steroidal alkaloids from Veratrum californicum (Durand) are known to exert teratogenic effects (e.g., cyclopia, holoprosencephaly) by blocking the Hedgehog (Hh) signaling pathway, which plays a considerable role in embryonic development and organogenesis. Most surprisingly, recent studies demonstrate that this complex signaling network is active even in the healthy adult organism, where it seem...