title: Biotransformation of dehydro-epi-androsterone by Aspergillus parasiticus: Metabolic evidences of BVMO activity.
abstract: The research on the synthesis of steroids and its derivatives is of high interest due to their clinical applications. A particular focus is given to molecules bearing a D-ring lactone like testolactone because of its bioactivity. The Aspergillus genus has been used to perform steroid biotransformations since it offers a toolbox of redox enzymes. In this work, the use of growing cells of Aspergillus parasiticus to study the bioconversion of dehydro-epi-androsterone (DHEA) is described, emphasizing the metabolic steps leading to D-ring lactonization products. It was observed that A. parasiticus is not only capable of transforming bicyclo[3.2.0]hept-2-en-6-one, the standard Baeyer-Villiger monooxygenase (BVMO) substrate, but also yielded testololactone and the homo-lactone 3β-hydroxy-17a-oxa-D-homoandrost-5-en-17-one from DHEA. Moreover, the biocatalyst degraded the lateral chain of cortisone by an oxidative route suggesting the action of a BVMO, thus providing enough metabolic evidences denoting the presence of BVMO activity in A. parasiticus. Furthermore, since excellent biotransformation rates were observed, A. parasiticus is a promising candidate for the production of bioactive lactone-based compounds of steroidal origin in larger scales.
authors.affiliation: Area de Química Orgánica, Facultad de Química, Bioquímica y Farmacia, Universidad Nacional de San Luis, INTEQUI-CONICET, San Luis 5700, Argentina.
authors.forename: M Laura
authors.initials: ML
authors.lastname: Mascotti
authors.affiliation: Area de Química Orgánica, Facultad de Química, Bioquímica y Farmacia, Universidad Nacional de San Luis, INTEQUI-CONICET, San Luis 5700, Argentina.
authors.forename: Martín A
authors.initials: MA
authors.lastname: Palazzolo
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, INFIQC-CONICET, Córdoba 5000, Argentina.
authors.forename: Fabricio R
authors.initials: FR
authors.lastname: Bisogno
authors.affiliation: Area de Química Orgánica, Facultad de Química, Bioquímica y Farmacia, Universidad Nacional de San Luis, INTEQUI-CONICET, San Luis 5700, Argentina. Electronic address: marcelakurina@gmail.com.
authors.forename: Marcela
authors.initials: M
authors.lastname: Kurina-Sanz
mesh_terms: D001230:Aspergillus / Q000201:enzymology / Q000378:metabolism*; D001711:Biotransformation; D003687:Dehydroepiandrosterone / Q000737:chemistry / Q000378:metabolism*; D006899:Mixed Function Oxygenases / Q000378:metabolism*
chemical_list: D003687:Dehydroepiandrosterone; D006899:Mixed Function Oxygenases
keywords: Aspergillus parasiticus; Baeyer-Villiger monooxygenase; Biotransformation; Cortisone; Dehydro-epi-androsterone; Steroids