Microbial functionalization of (-)-Ambroxide by filamentous fungi

J. A. ALLENDES, D. A. BUSTOS, A. DEL V. PACCIARONI, V. E. SOSA, D. A. BUSTOS.

BIOCATALYSIS AND BIOTRANSFORMATION

TAYLOR & FRANCIS LTD

Lugar: Londres; Año: 2011 vol. 29 p. 83 - 86

1024-2422

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.