Jervine

Jervine
Names
IUPAC name
3β-Hydroxy-17β,23β-epoxyveratraman-11-one
Systematic IUPAC name
(2′R,3S,3′R,3′aS,6′S,6aS,6bS,7′aR,11aS,11bR)-3-Hydroxy-3′,6′,10,11b-tetramethyl-2,3,3′a,4,4′,5′,6,6′,6a,6b,7,7′,7′a,8,11a,11b-hexadecahydro-3′H-spiro[benzo[a]fluorene-9,2′-furo[3,2-b]pyridin]-11(1H)-one
Other names
(3β,23β)-17,23-Epoxy-3-hydroxyveratraman-11-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.745 Edit this at Wikidata
UNII
  • InChI=1S/C27H39NO3/c1-14-11-21-24(28-13-14)16(3)27(31-21)10-8-19-20-6-5-17-12-18(29)7-9-26(17,4)23(20)25(30)22(19)15(27)2/h5,14,16,18-21,23-24,28-29H,6-13H2,1-4H3/t14-,16+,18-,19-,20-,21+,23+,24-,26-,27-/m0/s1 checkY
    Key: CLEXYFLHGFJONT-DNMILWOZSA-N checkY
  • InChI=1/C27H39NO3/c1-14-11-21-24(28-13-14)16(3)27(31-21)10-8-19-20-6-5-17-12-18(29)7-9-26(17,4)23(20)25(30)22(19)15(27)2/h5,14,16,18-21,23-24,28-29H,6-13H2,1-4H3/t14-,16+,18-,19-,20-,21+,23+,24-,26-,27-/m0/s1
    Key: CLEXYFLHGFJONT-DNMILWOZBJ
  • O=C5/C3=C(/[C@@]1(O[C@@H]2C[C@@H](CN[C@H]2[C@H]1C)C)CC[C@H]3[C@@H]6C/C=C4/C[C@@H](O)CC[C@]4(C)[C@@H]56)C
Properties
C27H39NO3
Molar mass 425.60 g/mol
Solubility 10 mg/mL in EtOH
6 mg/mL in DMF
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X markN verify (what is checkYX markN ?)

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


Physiological effects

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

Mechanism of action

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. With smoothened inhibited, the GLI1 transcription cannot be activated and hedgehog target genes cannot be transcribed.[citation needed]

References

  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.