IMBIV   05474
INSTITUTO MULTIDISCIPLINARIO DE BIOLOGIA VEGETAL
Unidad Ejecutora - UE
artículos
Título:
Microbial functionalization of (-)-Ambroxide by filamentous fungi
Autor/es:
J. A. ALLENDES, D. A. BUSTOS, A. DEL V. PACCIARONI, V. E. SOSA, D. A. BUSTOS.
Revista:
BIOCATALYSIS AND BIOTRANSFORMATION
Editorial:
TAYLOR & FRANCIS LTD
Referencias:
Lugar: Londres; Año: 2011 vol. 29 p. 83 - 86
ISSN:
1024-2422
Resumen:
Biocatalysis is a very useful tool for organic chemists to functionalize organic compounds under working conditions
milder than chemical ones. This methodology has special signifi cance since it can be an easy way to introduce a functional
group in a non-reactive carbon, region- and stereoselectively. In order to look for new compounds with antioxidant
activity we report the transformation of the natural substrate ( )-ambroxide using the enzyme potential of pure strains of
the fi lamentous fungi Alternaria alternata and Cunninghamella sp., following a protocol with growing cell cultures, which
produced the new compound 1 â -hydroxyambroxide and the previously known compound 3 â -hydroxyambroxide.
After purifi cation their structures were elucidated by spectroscopic methods. These two metabolites are the products of
oxidation of ring A of the starting material, without evidence of other compounds with different functionalization. Both
compounds were tested for their activity as free radical scavengers in vitro , using the assay of DPPH (1,1-diphenyl-
2-picrylhydrazyl) radical trapping. The results demonstrated that hydroxylation of carbons C-1 and C-3 of ( )-ambroxide
with â stereochemistry had no effect on biological activity as an antioxidant compared with the starting material and a
reference substance.Alternaria alternata and Cunninghamella sp., following a protocol with growing cell cultures, which
produced the new compound 1 â -hydroxyambroxide and the previously known compound 3 â -hydroxyambroxide.
After purifi cation their structures were elucidated by spectroscopic methods. These two metabolites are the products of
oxidation of ring A of the starting material, without evidence of other compounds with different functionalization. Both
compounds were tested for their activity as free radical scavengers in vitro , using the assay of DPPH (1,1-diphenyl-
2-picrylhydrazyl) radical trapping. The results demonstrated that hydroxylation of carbons C-1 and C-3 of ( )-ambroxide
with â stereochemistry had no effect on biological activity as an antioxidant compared with the starting material and a
reference substance.â -hydroxyambroxide and the previously known compound 3 â -hydroxyambroxide.
After purifi cation their structures were elucidated by spectroscopic methods. These two metabolites are the products of
oxidation of ring A of the starting material, without evidence of other compounds with different functionalization. Both
compounds were tested for their activity as free radical scavengers in vitro , using the assay of DPPH (1,1-diphenyl-
2-picrylhydrazyl) radical trapping. The results demonstrated that hydroxylation of carbons C-1 and C-3 of ( )-ambroxide
with â stereochemistry had no effect on biological activity as an antioxidant compared with the starting material and a
reference substance.in vitro , using the assay of DPPH (1,1-diphenyl-
2-picrylhydrazyl) radical trapping. The results demonstrated that hydroxylation of carbons C-1 and C-3 of ( )-ambroxide
with â stereochemistry had no effect on biological activity as an antioxidant compared with the starting material and a
reference substance.â stereochemistry had no effect on biological activity as an antioxidant compared with the starting material and a
reference substance.