Biotransformation of dehydro-epi-androsterone by Aspergillus parasiticus: metabolic evidences of BVMO activity

MASCOTTI ML; KURINA-SANZ M; BISOGNO FR; PALAZZOLO M

STEROIDS

ELSEVIER SCIENCE INC

Lugar: Amsterdam; Año: 2016 p. 44 - 49

0039-128X

The research on the synthesis of steroids and its derivatives is of high interest due to their clinicalapplications. A particular focus is given to molecules bearing a D-ring lactone like testolactone becauseof its bioactivity. The Aspergillus genus has been used to perform steroid biotransformations since it offersa toolbox of redox enzymes. In this work, the use of growing cells of Aspergillus parasiticus to study thebioconversion of dehydro-epi-androsterone (DHEA) is described, emphasizing the metabolic steps lead-ing to D-ring lactonization products. It was observed that A. parasiticus is not only capable of transformingbicyclo[3.2.0]hept-2-en-6-one, the standard Baeyer-Villiger monooxygenase (BVMO) substrate, but alsoyielded testololactone and the homo-lactone 3b-hydroxy-17a-oxa-D-homoandrost-5-en-17-one fromDHEA. Moreover, the biocatalyst degraded the lateral chain of cortisone by an oxidative route suggestingthe action of a BVMO, thus providing enoughmetabolic evidences denoting the presence of BVMO activityin A. parasiticus. Furthermore, since excellent biotransformation rates were observed, A. parasiticus is apromising candidate for the production of bioactive lactone-based compounds of steroidal origin in largerscales.