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Vol. 30, Issue 10, 1137-1142, October 2002
Department of Comparative Biosciences and the Center for Molecular
and Environmental Toxicology, University of Wisconsin-Madison,
Madison, Wisconsin
S-Allyl-L-cysteine (SAC), a component of
garlic and a metabolite of allyl halides, is a known substrate for
multiple flavin-containing monooxygenases (FMOs). In the current study,
we characterize the in vivo SAC metabolism by investigating the
presence of SAC,
N-acetyl-S-allyl-L-cysteine (NASAC), and their corresponding sulfoxides in the urine of rats given
SAC (200 or 400 mg/kg i.p.). In some experiments, rats were given
aminooxyacetic acid (AOAA), an inhibitor of cysteine conjugate 
-lyase, or methimazole, an alternative FMO substrate, 30 min prior
to treatment with 200 mg/kg SAC. Nearly 40 to 50% of the dose was
recovered in the 24-h collection period. In all treatment groups, the
majority of the metabolites were excreted within 8 h. The major
metabolites detected were NASAC and NASAC sulfoxide (NASACS; nearly
30-40% and 5-10% of the dose, respectively). Only small amounts of
the dose (approximately 1.5%) were recovered as SAC and SAC sulfoxide
(SACS). Methimazole pretreatment significantly reduced amounts of both
SACS and NASACS detected in the urine when compared with rats given SAC
only, whereas AOAA pretreatment had no effect. In vitro assays
using rat liver microsomes were also carried out to compare the
sulfoxidation rates of SAC and NASAC. The results showed that SAC was
much more readily oxidized than NASAC. Collectively, the results
provide evidence for the involvement of FMOs in the in vivo metabolism
of SAC and that SAC is a much better substrate for FMOs than its
corresponding mercapturic acid.
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