Pothuluri J V, Freeman J P, Evans F E, Cerniglia C E
Microbiology Division, Food and Drug Administration, Jefferson, Arkansas 72079.
Appl Environ Microbiol. 1990 Oct;56(10):2974-83. doi: 10.1128/aem.56.10.2974-2983.1990.
The fungus Cunninghamella elegans ATCC 36112 metabolized approximately 80% of the 3-14C-labeled fluoranthene (FA) added within 72 h of incubation. C. elegans metabolized FA to trans-2,3-dihydroxy-2,3-dihydrofluoranthene (trans-2,3-dihydrodiol), 8- and 9-hydroxyfluoranthene trans-2,3-dihydrodiol, 3-fluoranthene-beta-glucopyranoside, and 3-(8-hydroxyfluoranthene)-beta-glucopyranoside. These metabolites were separated by thin-layer and reversed-phase high-performance liquid chromatography and identified by 1H nuclear magnetic resonance, UV, and mass spectral techniques. The major pathway involved hydroxylation to form a glucoside conjugate of 3-hydroxyfluoranthene and a glucoside conjugate of 3,8-dihydroxyfluoranthene which together accounted for 52% of the total ethyl acetate-soluble metabolites. C. elegans initially metabolized FA in the 2,3 position to form fluoranthene trans-2,3-dihydrodiol, which has previously been shown to be a biologically active compound in mammalian and bacterial genotoxicity tests. However, C. elegans formed predominantly glucoside conjugates of the phenolic derivatives of FA, which suggests that this fungus has the potential to detoxify FA.
线虫状小克银汉霉（Cunninghamella elegans）ATCC 36112在培养72小时内代谢了添加的约80%的3-¹⁴C标记荧蒽（FA）。线虫状小克银汉霉将FA代谢为反式-2,3-二羟基-2,3-二氢荧蒽（反式-2,3-二氢二醇）、8-和9-羟基荧蒽反式-2,3-二氢二醇、3-荧蒽-β-葡萄糖苷以及3-(8-羟基荧蒽)-β-葡萄糖苷。这些代谢产物通过薄层色谱和反相高效液相色谱进行分离，并通过¹H核磁共振、紫外和质谱技术进行鉴定。主要途径包括羟基化，形成3-羟基荧蒽的葡萄糖苷缀合物和3,8-二羟基荧蒽的葡萄糖苷缀合物，它们总共占乙酸乙酯可溶代谢产物总量的52%。线虫状小克银汉霉最初在2,3位代谢FA，形成荧蒽反式-2,3-二氢二醇，此前在哺乳动物和细菌遗传毒性试验中已证明其为生物活性化合物。然而，线虫状小克银汉霉主要形成FA酚类衍生物的葡萄糖苷缀合物，这表明这种真菌具有使FA解毒的潜力。
