PYRENE METABOLISM IN CRINIPELLIS-STIPITARIA - IDENTIFICATION OF TRANS-4,5-DIHYDRO-4,5-DIHYDROXYPYRENE AND 1-PYRENYLSULFATE IN STRAIN JK364

The isolation and identification of two novel metabolites in the funga l metabolism of pyrene are described. The plant-inhabiting basidiomyce te Crinipellis stipitaria JK364 metabolized pyrene, a polycyclic aroma tic hydrocarbon containing four rings, when grown in submerged culture s in a medium containing malt extract, glucose, and yeast extract. In experiments with [C-14]pyrene, after 7 days of incubation 40% of the l abeled substrate was converted into organic solvent-extractable metabo lites. Metabolites isolated from cultures grown with pyrene were ident ified as 1-pyrenylsulfate and trans-4,5-dihydro-4,5-dihydroxypyrene. 1 -Hydroxypyrene, the precursor of 1-pyrenylsulfate, was also detected. 1-Pyrenylsulfate was isolated from mycelial extracts, whereas trans-4, 5-dihydro-4,5-dihydroxypyrene was recovered from the culture filtrate. Identification of the compounds,vas based on their UV spectra, mass s pectra, and nuclear magnetic resonance spectra. This is the first repo rt on the detoxification of a polycyclic aromatic hydrocarbon by a pla nt-inhabiting basidiomycete. The occurrence of 1-pyrenylsulfate and tr ans-4,5-dihydro-4,5-dihydroxypyrene among fungal metabolites of pyrene is also new.