Abstract:
:[14C]Naphthalene was given orally to rats with cannulated bile ducts and to germ-free rats. Bile and urine from the cannulated rats and urine from the germ-free rats contained no radioactive 1,2-dihydro-1-hydroxy-2-methylthionaphthalene and only trace amounts of radioactive naphthols or naphthol conjugates. Urine of control rats contained 4.6% of the 14C dose as naphthols and/or naphthol glucuronides. Appreciable quantities of 1- and 2-naphthol (7-20% of dose) and 1,2-dihydro-1-hydroxy-2-methylthionaphthalene (1-35% of dose) were in urine from rats dosed orally or intracecally with 1,2-dihydro-1-hydroxy-2-S-cysteinylnaphthalene and 1,2-dihydro-1-hydroxy-2-S-(N-acetyl)cysteinylnaphthalene. Apparently, in vivo, naphthols and methylthio-containing metabolites of naphthalene are formed during enterohepatic circulation of 1,2-dihydro-1-hydroxy-2-S-cysteinylnaphthalene and 1,2-dihydro-1-hydroxy-2-S-(N-acetyl)cysteinylnaphthalene in a process dependent upon intestinal microflora. A possible pathway for the formation of naphthols is aromatization of the precursor compounds by elimination of the appropriate substituent group from these metabolites. This discovery of the essential role of the intestinal microflora in the formation of naphthols from naphthalene indicates the existence of a novel pathway for hydroxylation of aromatic systems and challenges the current concept of the in vivo relevance of the in vitro production of naphthols from naphthalene 1,2-oxide.
journal_name
Proc Natl Acad Sci U S Aauthors
Bakke J,Struble C,Gustafsson JA,Gustafsson Bdoi
10.1073/pnas.82.3.668subject
Has Abstractpub_date
1985-02-01 00:00:00pages
668-71issue
3eissn
0027-8424issn
1091-6490journal_volume
82pub_type
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