Biotransformation of olivetol by Syncephalastrum racemosum

A study of the biotransformation of olivetol by Syncephalastrum racemosum ATCC 18192 has led to the isolation of three metabolites, which were identified as 4'-hydroxy-olivetol, 3-(3,5-dihydroxyphenyl)-1-propanol, and 3-(3,5-dihydroxyphenyl)-1-propanoic acid. The structures of the isolated metabolites were deduced by comparison of their spectral properties (pmr, cmr, ms) with those of olivetol. The absolute configuration of 4'-hydroxy-olivetol was determined to be R by the Horeau partial resolution method. Biotransformation of olivetol therefore appears to occur by a subterminal oxidation process.