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

doi:10.1135/cccc19981663

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

Molecular Sciences, School of (SMS)

Research output: Contribution to journal › Article › peer-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 language	English (US)
Pages (from-to)	1663-1670
Number of pages	8
Journal	Collection of Czechoslovak Chemical Communications
Volume	63
Issue number	10
DOIs	https://doi.org/10.1135/cccc19981663
State	Published - Oct 1998

Keywords

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

ASJC Scopus subject areas

General Chemistry

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10.1135/cccc19981663

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@article{e4fb505fe44e4b288171500f4358442b,

title = "Conformational preference of two toad poison bufadienolides, cinobufagin and bufotalin",

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.",

keywords = "Ab initio calculations, Bufadienolides, Bufotalin, Cinobufagin, Conformation analysis, Molecular mechanics, NMR spectroscopy, Semiempirical calculations, Steroids",

author = "Yoshiaki Kamano and Ayano Kotake and Toshihiko Nogawa and Hirohumi Hashima and Machiko Tozawa and Hiroshi Morita and Koichi Takeya and Hideji Itokawa and Ichiro Matsuo and Yoshitatsu Ichihara and Pavel Dra{\v s}ar and George Pettit",

year = "1998",

month = oct,

doi = "10.1135/cccc19981663",

language = "English (US)",

volume = "63",

pages = "1663--1670",

journal = "Collection of Czechoslovak Chemical Communications",

issn = "0010-0765",

publisher = "Wiley-VCH Verlag",

number = "10",

}

TY - JOUR

T1 - Conformational preference of two toad poison bufadienolides, cinobufagin and bufotalin

AU - Kamano, Yoshiaki

AU - Kotake, Ayano

AU - Nogawa, Toshihiko

AU - Hashima, Hirohumi

AU - Tozawa, Machiko

AU - Morita, Hiroshi

AU - Takeya, Koichi

AU - Itokawa, Hideji

AU - Matsuo, Ichiro

AU - Ichihara, Yoshitatsu

AU - Drašar, Pavel

AU - Pettit, George

PY - 1998/10

Y1 - 1998/10

N2 - 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.

AB - 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.

KW - Ab initio calculations

KW - Bufadienolides

KW - Bufotalin

KW - Cinobufagin

KW - Conformation analysis

KW - Molecular mechanics

KW - NMR spectroscopy

KW - Semiempirical calculations

KW - Steroids

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U2 - 10.1135/cccc19981663

DO - 10.1135/cccc19981663

M3 - Article

AN - SCOPUS:0032357017

SN - 0010-0765

VL - 63

SP - 1663

EP - 1670

JO - Collection of Czechoslovak Chemical Communications

JF - Collection of Czechoslovak Chemical Communications

IS - 10

ER -

Conformational preference of two toad poison bufadienolides, cinobufagin and bufotalin

Abstract

Keywords

ASJC Scopus subject areas

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