Isolation and structure of a 20,21-epoxybufenolide series from "Ch'an Su"

Yoshiaki Kamano, Toshihiko Nogawa, Ayano Yamashita, Masahiko Hayashi, Masuo Inoue, Pavel Drašar, George Pettit

Research output: Contribution to journalArticle

54 Citations (Scopus)

Abstract

Steroid bufenolides resulting from epoxidation of the 17β-2-pyrone ring of bufadienolides are rare. Five 20,21-epoxybufenolides, namely, 20S,21-epoxyresibufogenin (1), 20R,21-epoxyresibufogenin (2), 3-O-formyl-20S,21-epoxyresibufogenin (3), 3-O-formyl-20R,21-epoxyresibufogenin (4), and 3-oxo-20S,21-epoxyresibufogenin (5), were isolated from the Chinese toad skin extract drug Ch'an Su. The structures were elucidated by spectroscopic and chemical methods. The configuration at C-20 was assigned by the analysis of difference NOE spectra. The cancer cell (KB and MH-60) growth inhibition by the new 20,21-epoxybufenolides was examined, and 20,21-epoxides 1, 2, and 5 were found to significantly inhibit the leukemia MH-60 cell line.

Original languageEnglish (US)
Pages (from-to)1001-1005
Number of pages5
JournalJournal of Natural Products
Volume65
Issue number7
DOIs
StatePublished - 2002

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Bufanolides
bufadienolides
pyrones
KB Cells
Epoxy Compounds
toads
leukemia
epoxides
skin (animal)
Anura
growth retardation
steroids
Leukemia
Steroids
Cells
cell lines
Cell Line
drugs
Skin
Epoxidation

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Kamano, Y., Nogawa, T., Yamashita, A., Hayashi, M., Inoue, M., Drašar, P., & Pettit, G. (2002). Isolation and structure of a 20,21-epoxybufenolide series from "Ch'an Su". Journal of Natural Products, 65(7), 1001-1005. https://doi.org/10.1021/np0200360

Isolation and structure of a 20,21-epoxybufenolide series from "Ch'an Su". / Kamano, Yoshiaki; Nogawa, Toshihiko; Yamashita, Ayano; Hayashi, Masahiko; Inoue, Masuo; Drašar, Pavel; Pettit, George.

In: Journal of Natural Products, Vol. 65, No. 7, 2002, p. 1001-1005.

Research output: Contribution to journalArticle

Kamano, Y, Nogawa, T, Yamashita, A, Hayashi, M, Inoue, M, Drašar, P & Pettit, G 2002, 'Isolation and structure of a 20,21-epoxybufenolide series from "Ch'an Su"', Journal of Natural Products, vol. 65, no. 7, pp. 1001-1005. https://doi.org/10.1021/np0200360
Kamano Y, Nogawa T, Yamashita A, Hayashi M, Inoue M, Drašar P et al. Isolation and structure of a 20,21-epoxybufenolide series from "Ch'an Su". Journal of Natural Products. 2002;65(7):1001-1005. https://doi.org/10.1021/np0200360
Kamano, Yoshiaki ; Nogawa, Toshihiko ; Yamashita, Ayano ; Hayashi, Masahiko ; Inoue, Masuo ; Drašar, Pavel ; Pettit, George. / Isolation and structure of a 20,21-epoxybufenolide series from "Ch'an Su". In: Journal of Natural Products. 2002 ; Vol. 65, No. 7. pp. 1001-1005.
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