Fungal hydroxylation of (-)-α-santonin

BUSTO D.; PACCIARONI A.; SOSA, V.E; BUSTO D.

Reports in Organic Chemistry

Dovepress

Año: 2012 vol. 2 p. 1 - 1

2230-5246

Functionalization of organic compounds using enzymes present in microorganisms is a very useful tool for organic chemists, since it is a method carried out under milder conditions than chemical ones and allows the introduction of functional groups in a nonreactive carbon in a regioselective and stereoselective way. In order to look for new compounds derived from natural products with antioxidant and cytotoxic activity, the sesquiterpene lactone (-)-α-santonin was transformed using a pure strain of Cunninghamella spp. A two-stage standard protocol with growing cells was followed, which led to 8β-hydroxy-α-santonin. The structure of the product was unequivocally elucidated by spectroscopic methods. Both the starting material and metabolite were tested in vitro for antioxidant activity using the 1,1-diphenyl-2-picrylhydrazyl method, and cytotoxic activity was tested using the Artemia salina (brine shrimp) method. In both assays, the new compound was less active than subst