Stereochemical correlation between 10-hydroperoxyoctadecadienoic acid and 1-octen-3-ol in Lentinula edodes and Tricholoma matsutake mushrooms

被引:22
作者
Akakabe, Y [1 ]
Matsui, K [1 ]
Kajiwara, T [1 ]
机构
[1] Yamaguchi Univ, Fac Agr, Dept Biol Chem, Yamaguchi 7538515, Japan
关键词
mushroom; 1-octen-3-ol; linoteic acid; 10-hydroperoxyoctadecadienoic acid; glutathione peroxidase;
D O I
10.1271/bbb.69.1539
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Linoleic acid (LA) incubated with a homogenate of Lentinula edodes or Tricholoma matsutake mushroom significantly increased the amount of (R)-1-octen-3-ol. The alcohol was identified as (S)-10-HODE with 90-87% and > 99% enantiomeric excess (ee), respectively. During the incubation of LA with these homogenates in the presence of glutathione-glutathione peroxidase (GSH-GPx), which can reduce hydroperoxy fatty acids to the corresponding hydroxy acids, the formation of (R)-1-octen-3-ol was significantly inhibited, whereas the amount of 10-hydroxy-(8E,12Z)-8,12-octadecadienoic acid (10-HODE) was significantly increased. The acid was identified as (S)-10-HODE with 92-88% ee and > 99% ee, respectively. The decrease in the amount of alcohol was approximately the same as the increase in amount of HODE in both mushrooms. These results indicate a stereochemical correlation between (R)-1-octen-3-ol and (S)-10-hydroperoxy-(8E,12Z)-8,12-octadecadienoic acid [(S)-10-HPODE] in both mushrooms.
引用
收藏
页码:1539 / 1544
页数:6
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