Isolation and structure of a 20,21-epoxybufenolide series from "Ch'an Su"
Isolation and structure of a 20,21-epoxybufenolide series from "Ch'an Su"
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DOI：
10.1021/np0200360
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发表时间：
2002-07-01
影响因子：
5.1
通讯作者：
Pettit, GR
中科院分区：
文献类型：
--
作者：
Kamano, Y;Nogawa, T;Pettit, GR
由蟾蜍二烯内酯的17 β-2-吡喃酮环的环氧化产生的类固醇蟾蜍内酯是罕见的。从中药蟾皮提取物中分离得到5个20，21-环氧蟾蜍内酯，即20 S，21-环氧脂蟾毒配基（1），20 R，21-环氧脂蟾毒配基（2），3-O-甲酰基-20S，21-环氧脂蟾毒配基（3），3-O-甲酰基-20R，21-环氧脂蟾毒配基（4）和3-氧代-20S，21-环氧脂蟾毒配基（5）。通过波谱和化学方法鉴定了其结构。通过对不同NOE谱的分析，确定了C-20位的构型。研究了新的20，21-环氧丁内酯对癌细胞（KB和MH-60）生长的抑制作用，发现20，21-环氧化合物1、2和5对白血病MH-60细胞系有显著的抑制作用。
Steroid bufenolides resulting from epoxidation of the 17beta-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.