METABOLITES OF 4-N-NONYLPHENOL IN WHEAT CELL-SUSPENSION CULTURES

4-Nonylphenol, a metabolite of nonionic surfactants, was examined for its metabolism in cell cultures of wheat according to a standardized m ethod. Four major radioactively labeled fractions were detected and is olated by chromatography on Sephadex LH-20 and semipreparative HPLC. H ydrolysis of the peaks resulted in two compounds which were purified b y semipreparative HPLC. Using enzymatic hydrolysis, HPLC, GC-MS, and E SI-MS/MS, the chemical structures were elucidated. They were shown to be 4-(hydroxy)- and 4-(dihydroxy)nonylphenols which were glucosylated at the phenolic OH-group and further glucosylated, glucuronidated, and acylated with acetic acid or malonic acid. Except for C-1 and C-9, th e hydroxylations occurred at all C atoms of the alkyl side chain.