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

doi:10.1021/np0200360

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

Molecular Sciences, School of (SMS)

Research output: Contribution to journal › Article › peer-review

67 Scopus citations

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 language	English (US)
Pages (from-to)	1001-1005
Number of pages	5
Journal	Journal of Natural Products
Volume	65
Issue number	7
DOIs	https://doi.org/10.1021/np0200360
State	Published - 2002

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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10.1021/np0200360

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

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.",

author = "Yoshiaki Kamano and Toshihiko Nogawa and Ayano Yamashita and Masahiko Hayashi and Masuo Inoue and Pavel Dra{\v s}ar and George Pettit",

year = "2002",

doi = "10.1021/np0200360",

language = "English (US)",

volume = "65",

pages = "1001--1005",

journal = "Journal of Natural Products",

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T1 - Isolation and structure of a 20,21-epoxybufenolide series from "Ch'an Su"

AU - Kamano, Yoshiaki

AU - Nogawa, Toshihiko

AU - Yamashita, Ayano

AU - Hayashi, Masahiko

AU - Inoue, Masuo

AU - Drašar, Pavel

AU - Pettit, George

PY - 2002

Y1 - 2002

N2 - 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.

AB - 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.

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SN - 0163-3864

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JO - Journal of Natural Products

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IS - 7

ER -

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

Abstract

ASJC Scopus subject areas

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