Bioscience, Biotechnology, and Biochemistry
Online ISSN : 1347-6947
Print ISSN : 0916-8451
Food & Nutrition Science Regular Papers
Stereochemical Correlation between 10-Hydroperoxyoctadecadienoic Acid and 1-Octen-3-ol in Lentinula edodes and Tricholoma matsutake Mushrooms
Yoshihiko AKAKABEKenji MATSUITadahiko KAJIWARA
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2005 年 69 巻 8 号 p. 1539-1544

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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.
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© 2005 by Japan Society for Bioscience, Biotechnology, and Agrochemistry
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