β-hydroxyergothioneine, a new ergothioneine derivative from the mushroom Lyophyllum connatum, and its protective activity against carbon tetrachloride-induced injury in primary culture hepatocytes

β-hydroxyergothioneine, a new ergothioneine derivative from the mushroom Lyophyllum connatum, and its protective activity against carbon tetrachloride-induced injury in primary culture hepatocytes
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DOI:
10.1271/bbb.69.357
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发表时间:
2005-02-01
影响因子:
1.6
通讯作者:
Sugawara, Y
Sugawara, Y
中科院分区:
工程技术4区
文献类型:
--
作者:
Kimura, C;Nukina, M;Sugawara, Y

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从离褶伞中分离得到一个新的麦角硫因衍生物,命名为β-羟基麦角硫因。还分离出麦角硫因、N-羟基-N ',N'-二甲基脲和connatin(N-羟基-N ',N'-二甲基-瓜氨酸)。1,1-二苯基-2-苦肼基(DPPH)自由基清除试验表明,所有化合物均具有清除自由基的能力。通过光谱分析和X射线晶体学进行结构测定,包括β-羟基麦角硫因的绝对立体化学。β-羟基麦角硫因的自由基清除活性与麦角硫因基本相同。β-羟基麦角硫因对四氯化碳诱导的原代培养肝细胞损伤具有最大的保护活性。
A new ergothioneine derivative named beta-hydroxyergothioneine was isolated from the mushroom Lyophyllum connatum. Ergothioneine,N-hydroxy-N',N'-dimethylurea, and connatin (N-hydroxy-N',N'-dimethyl-citrulline) were also isolated. All the compounds displayed the ability to scavenge free radicals, based on a 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay. Structural determination, including the absolute stereochemistry of beta-hydroxyergothioneine, was achieved by spectroscopic analysis and X-ray crystallography. The radical scavenging activity of beta-hydroxyergothioneine was almost the same as that of ergothioneine. beta-Hydroxyergothioneine showed the greatest protective activity against carbon tetrachloride-induced injury in primary culture hepatocytes.