Cyclopamine and related steroidal alkaloid teratogens: Their occurrence, structural relationship, and biologic effects

@article{Keeler2006CyclopamineAR,
  title={Cyclopamine and related steroidal alkaloid teratogens: Their occurrence, structural relationship, and biologic effects},
  author={Richard F. Keeler},
  journal={Lipids},
  year={2006},
  volume={13},
  pages={708-715}
}
  • R. Keeler
  • Published 2006
  • Biology, Medicine
  • Lipids
A spontaneous congenital deformity is produced in lambs whose dams consumeVeratrum californicum on the 14th day of gestation. The deformity is generally expressed as cyclopia, cebocephaly, anophthalmia, or microphthalmia. This teratogenic effect is produced by certain steroidal alkaloid teratogens from the plant—most notably the compound cyclopamine. Cyclopamine is a C-nor-D-homo steroid with fused furanopiperidine rings E and F at right angles to the plane of the steroid because of spiro… Expand
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References

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Teratogenic compounds of Veratrum californicum (Durand). V. Comparison of cyclopian effects of steroidal alkaloids from the plant and structurally related compounds from other sources.
Cyclopamine, and its glycoside alkaloid X, along with jervine and veratrosine, induced cyclopian malformations in offspring born to ewes ingesting these compounds on the fourteenth day of gestation.Expand
Teratogenic compounds of Veratrum californicum (Durand). VII. The structure of the glycosidic alkaloid cycloposine.
TLDR
The structure was elucidated of a polar, glycosidic alkaloid, cycloposine, from Veratrum californicum, known to produce fetal cyclopia and related central nervous system malformations in sheep and identified as 3-glucosylcyclopamine. Expand
Effects of alkaloids of Veratrum californicum on chick embryos.
TLDR
It appears that these compounds produce head malformations in chick and sheep embryos when they are exposed relatively at about the same developmental stage. Expand
Teratogenic Effects of Cyclopamine and Jervine in Rats, Mice and Hamsters 1
  • R. Keeler
  • Medicine
  • Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine
  • 1975
Summary Golden hamster fetuses were extremely sensitive to the teratogenic action of jervine and cyclopamine, the steroidal alkaloid teratogens from Veratrum cali-fornicum. Cebocephaly, harelip/cleftExpand
Teratogenic compounds of Veratrum californicum (Durand) X. Cyclopia in rabbits produced by cyclopamine.
TLDR
Both in vitro and in vivo experiments suggested the conversion of nonbuffered cyclopamine to veratramine under stomach-acid conditions. Expand
Teratogenic compounds in Veratrum californicum (Durand) IX. Structure-activity relation.
TLDR
The structures and configurations of three naturally occurring steroidal alkaloid teratogens from Veratrum californicum that induce cyclopia in sheep have been elucidated and methods are proposed to enable elucidation of the precise structural requirements for this teratogenic effect. Expand
Teratogenic compounds of veratrum californicum (durand) - VI
TLDR
The teratogenic steroidal alkaloid, cyclopamine, from Veratrum californicum responsible for cyclopian and related central nervous system malformations in sheep was investigated and identified as 11-deoxojervine. Expand
Chemical Compounds of Veratrum calif ornicum Related to Congenital Ovine Cyclopian Malformations
  • R. Keeler, W. Binns
  • Chemistry, Medicine
  • Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine
  • 1964
Summary The teratogenic material from Veratrum californicum has been extracted from dried plant material by an ethanol extraction of the plant residue remaining after an initial benzene extraction inExpand
Teratogenic Compounds of Veratrum californicum (Durand) XI. Gestational Chronology and Compound Specificity in Rabbits
  • R. Keeler
  • Biology, Medicine
  • Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine
  • 1971
Summary Fetal rabbits become malformed in ways grossly similar to lambs upon maternal ingestion of cyclopamine and jervine, naturally-occurring teratogens of Veratrum californicum. Other veratrumExpand
Teratogenic Compounds of Veratrum californicum (Durand). XIV. Limb Deformities Produced by Cyclopamine
  • R. Keeler
  • Medicine
  • Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine
  • 1973
TLDR
Four major alkaloids isolated from Veratrum californicum—veratramine, veratrosine, cyclopamine, and muldamine— were fed to pregnant ewes during the fifth week of gestation, producing the same congenital deformities of limbs previously produced by whole plants. Expand
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