Microbial functionalization of (-)-ambroxide by filamentous fungi

作者：Allendes Jorge Ariel; Bustos Daniela Alicia; Pacciaroni Adriana Del Valle; Sosa Virginia Estela; Bustos Daniel Alfredo

来源：Biocatalysis and Biotransformation, 2011, 29(2-3): 83-86.

DOI：10.3109/10242422.2011.578211

• Biotransformation
• Cunninghamella sp.
• Alternaria alternata
• 1 beta-hydroxyambroxide
• 3 beta-hydroxyambroxide
• radical scavenger activity

Biocatalysis is a very useful tool for organic chemists to functionalize organic compounds under working conditions milder than chemical ones. This methodology has special significance since it can be an easy way to introduce a functional group in a non-reactive carbon, regio- 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 filamentous fungi Alternaria alternata and Cunninghamella sp., following a protocol with growing cell cultures, which produced the new compound 1 beta-hydroxyambroxide and the previously known compound 3 beta-hydroxyambroxide. After purification 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 beta stereochemistry had no effect on biological activity as an antioxidant compared with the starting material and a reference substance.

• 出版日期2011-3