Steroid hydroxylation by whetzelinia sclerotiorum, Phanerochaete chrysosporium and Mucor plumbeus

Abstract The fungi Whetzelinia sclerotiorum ATCC 18687, Phanerochaete chrysosporium ATCC 24725 and Mucor plumbeus ATCC 4740 were examined for their ability to perform steroid biotransformations under single phase, pulse feed conditions. The steroids 3β-hydroxyandrost-5-en-17-one (dehydro epi androsterone) ( 1 ), 17β-hydroxyandrost-4-en-3-one (testosterone) ( 5 ), 3β-hydroxypregn-5-en-20-one (pregnenolone) ( 3 ), pregn-4-ene-3,20-dione (progesterone) ( 9 ), 17α,21-dihydroxypregn-4-ene-3,11,20-trione (cortisone) ( 11 ), 17α,21-dihydroxypregna-1,4-diene-3,11,20-trione (prednisone) ( 14 ), and 3-hydroxyestra-1,3,5(10)-trien-17-one (estrone) ( 15 ) were fed to each fungus. The production of a number of novel metabolites is reported. Of the fungi investigated W. sclerotiorum performed the most interesting biotransformations and had a clear propensity for 2β, 6β/7β and 15β/16β hydroxylations. P. chrysosporium was more prone functionalize steroids in the allylic position. Oxygen insertion at C-14 by M. plumbeus is reported for the first time. All three micro-organisms exhibited redox activity.