Jervine

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Jervine
Jervine.png
Names
IUPAC name
(2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)-2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11a,11b- Hexadecahydro-3-hydroxy-3',6',10,11b-tetramethyl-spiro[9H-benzo[a]fluorene- 9,2'(3'H)-furo[3,2-b] pyridin]-11(1H)-one
Other names
(3β,23β)-17,23-Epoxy-3-hydroxyveratraman-11-one
Identifiers
469-59-0 N
ChEMBL ChEMBL186779 YesY
ChemSpider 9694 YesY
Jmol-3D images Image
PubChem 10098
Properties
C27H39NO3
Molar mass 425.60 g/mol
Solubility 10 mg/mL in EtOH
6 mg/mL in DMF
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Jervine is a steroidal alkaloid with molecular formula C27H39NO3 which is derived from the Veratrum plant genus. Similar to cyclopamine, which also occurs in the Veratrum genus, it is a teratogen implicated in birth defects when consumed by animals during a certain period of their gestation.

Physiological effects[edit]

Jervine is a potent teratogen causing birth defects in vertebrates. In severe cases it can cause cyclopia and holoprosencephaly.

Mechanism of action[edit]

Jervine's biological activity is mediated via its interaction with the 7 pass trans membrane protein smoothened. Jervine binds with and inhibits smoothened, which is an integral part of the hedgehog signaling pathways.[1] With smoothened inhibited, the GLI1 transcription cannot be activated and hedgehog target genes cannot be transcribed.

References[edit]

  1. ^ Chen, J; Taipale, J; Cooper, M. (2002). "Inhibition of Hedgehog Signaling by direct binding of Cyclopamine to Smoothened". Genes Dev. 16 (21): 2743–2748. doi:10.1101/gad.1025302. PMC 187469. PMID 12414725.