Stereochemical correlation between 10-hydroperoxyoctadecadienoic acid and 1-octen-3-ol in Lentinula edodes and Tricholoma matsutake mushrooms.
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.
Akakabe
Yoshihiko
Y
Department of Biological Chemistry, Faculty of Agriculture, Yamaguchi University, Japan. akakabe@yamaguchi-u.ac.jp
Matsui
Kenji
K
Kajiwara
Tadahiko
T
D000363:Agaricales / Q000737:chemistry*; D002849:Chromatography, Gas; D005978:Glutathione / Q000737:chemistry; D005979:Glutathione Peroxidase / Q000737:chemistry; D008041:Linoleic Acids / Q000737:chemistry*; D000442:Octanols / Q000737:chemistry*; D013045:Species Specificity; D013237:Stereoisomerism
D008041:Linoleic Acids; D000442:Octanols; C058335:10-hydroperoxy-8,12-octadecadienoic acid; D005979:Glutathione Peroxidase; D005978:Glutathione; C038844:1-octen-3-ol