Document Detail

Stereochemical correlation between 10-hydroperoxyoctadecadienoic acid and 1-octen-3-ol in Lentinula edodes and Tricholoma matsutake mushrooms.
MedLine Citation:
PMID:  16116283     Owner:  NLM     Status:  MEDLINE    
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.
Yoshihiko Akakabe; Kenji Matsui; Tadahiko Kajiwara
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Bioscience, biotechnology, and biochemistry     Volume:  69     ISSN:  0916-8451     ISO Abbreviation:  Biosci. Biotechnol. Biochem.     Publication Date:  2005 Aug 
Date Detail:
Created Date:  2005-08-23     Completed Date:  2005-12-01     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  9205717     Medline TA:  Biosci Biotechnol Biochem     Country:  Japan    
Other Details:
Languages:  eng     Pagination:  1539-44     Citation Subset:  IM    
Department of Biological Chemistry, Faculty of Agriculture, Yamaguchi University, Japan.
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MeSH Terms
Agaricales / chemistry*
Chromatography, Gas
Glutathione / chemistry
Glutathione Peroxidase / chemistry
Linoleic Acids / chemistry*
Octanols / chemistry*
Species Specificity
Reg. No./Substance:
0/Linoleic Acids; 0/Octanols; 3391-86-4/1-octen-3-ol; 70-18-8/Glutathione; 90540-32-2/10-hydroperoxy-8,12-octadecadienoic acid; EC Peroxidase

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