Conformational preference of two toad poison bufadienolides, cinobufagin and bufotalin

Yoshiaki Kamano, Ayano Kotake, Toshihiko Nogawa, Hirohumi Hashima, Machiko Tozawa, Hiroshi Morita, Koichi Takeya, Hideji Itokawa, Ichiro Matsuo, Yoshitatsu Ichihara, Pavel Drašar, George Pettit

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

The solution state conformations of pyran-2-one ring (E ring) of two toad poison bufadienolides, cinobufagin and bufotalin, were analyzed by using NOE experiments at low temperatures and molecular dynamics simulation study. The rotation of E ring of the two bufadienolides, was found to be affected by the 14β,15β-epoxy and 16β-acetoxy groups and to be restricted at low temperatures. In the experimental, cinobufagin and bufotalin were isolated from Ch'an Su by the new chromatographic methods using the hydrophobic gel sephadex LH-20 and HP-cellulofine as carriers.

Original languageEnglish (US)
Pages (from-to)1663-1670
Number of pages8
JournalCollection of Czechoslovak Chemical Communications
Volume63
Issue number10
DOIs
StatePublished - Oct 1998

Keywords

  • Ab initio calculations
  • Bufadienolides
  • Bufotalin
  • Cinobufagin
  • Conformation analysis
  • Molecular mechanics
  • NMR spectroscopy
  • Semiempirical calculations
  • Steroids

ASJC Scopus subject areas

  • Chemistry(all)

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