UMYMFOR   05516
UNIDAD DE MICROANALISIS Y METODOS FISICOS EN QUIMICA ORGANICA
Unidad Ejecutora - UE
artículos
Título:
New metabolites of drospirenone obtained in Mucorales fungi culture
Autor/es:
PAULA G. QUINTANA; STELLA MARIS ROMERO; GRACIELA VAAMONDE; ALICIA BALDESSARI
Revista:
JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC
Editorial:
ELSEVIER SCIENCE BV
Referencias:
Lugar: Amsterdam; Año: 2013 vol. 97 p. 110 - 117
ISSN:
1381-1177
Resumen:
Microbial transformation of 6,7,15,16-dimethylene-3-oxo-17-pregn-4-ene-2,17-carbolactone, the well-known contraceptive drospirenone (1), using fungal cells was carried out. Six fungal strains of different species of Order Mucorales were evaluated in this study, namely Absidia corymbifera BAFC 1072, A. corymbifera BAFC 1080, A. coerulea, Mucor plumbeusBAFC 2314, Rhizopus oryzae and Syncephalastrum racemosum. Four products were obtained by hydroxylation at C-11 and C-2 and epimerization at C-17 of drospirenone by A.corymbifera BAFC 1072, A. coerulea and Syncephalastrum racemosum. The structures were elucidated as 6β,7β,15β,16β-dimethylene-11α-hydroxy-3-oxo-l7α-pregn-4-en-21,17-carbolactone (2), 6β,7β,15β,16β-dimethylene-11α-hydroxy-3-oxo-l7β-pregn-4-en-21,17carbolactone (3),6β,7β,15β,16β-dimethylene-11β-hydroxy-3-oxo-l7α-pregn-4-en-21,17-carbolactone (4) and 6β,7β,15β,16β-dimethylene-2β-hydroxy-3-oxo-l7α-pregn-4-en-21,17-carbolactone (5),on the basis of extensive spectral data including 2D NMR spectroscopy and MS. Products 3, 4and 5were found to be newcompounds. Several biotransformation parameters such as the employment of growing or resting cells, inoculumsize, agitation speed, drospirenone concentration, temperature, pH and presence of co-solvent resulted crucial in the optimization of the process.