title: Hedgehog antagonists cyclopamine and dihydroveratramine can be mistaken for each other in Veratrum album.
abstract: A toxic plant, Veratrum album (ssp. viriscens), was found to have an inhibitory effect on Hedgehog (Hh), a developmental signaling pathway that has been shown to be active during development, in adult stem cells and in numerous human tumors. Based on earlier studies it was believed that the known Hh inhibitor cyclopamine was present in V. album (ssp. viriscens). Here we show that instead of cyclopamine, dihydroveratramine (DHV) was found in V. album (ssp. viriscens). These compounds are easily mistaken for each other, as both substances share the same molecular weight, and the same main MS/MS fragments. DHV was found to be a less potent Hh inhibitor compared to cyclopamine. This is the first reported occurrence of DVH in nature.
authors.affiliation: Department of Chemistry, University of Oslo, P.O. Box 1033, Blindern, NO-0315 Oslo, Norway.
authors.forename: Steven Ray
authors.initials: SR
authors.lastname: Wilson
authors.forename: Martin Frank
authors.initials: MF
authors.lastname: Strand
authors.forename: Andreas
authors.initials: A
authors.lastname: Krapp
authors.forename: Frode
authors.initials: F
authors.lastname: Rise
authors.forename: Gunnar
authors.initials: G
authors.lastname: Herstad
authors.forename: Karl Egil
authors.initials: KE
authors.lastname: Malterud
authors.forename: Stefan
authors.initials: S
authors.lastname: Krauss
mesh_terms: D002851:Chromatography, High Pressure Liquid; D053823:Hedgehog Proteins / Q000037:antagonists & inhibitors*; D009682:Magnetic Resonance Spectroscopy; D013056:Spectrophotometry, Ultraviolet; D053719:Tandem Mass Spectrometry; D014703:Veratrum / Q000737:chemistry*; D014704:Veratrum Alkaloids / Q000032:analysis* / Q000494:pharmacology
chemical_list: D053823:Hedgehog Proteins; D014704:Veratrum Alkaloids; C000541:cyclopamine