Bio- and chemo- transformations of glabranin and 7-O-methylglabranin and cytotoxic evaluations of the transformed products

The biotransformation of glabranin (1) with Aspergillus niger and Cunninghamella blakesleeana favoured the formation of benzofuran derivatives (3 and 4), while in contrast, its acid-catalysed chemical transformation favoured the formation of benzopyran derivatives (6 and 7). Compound 6 was further biooxidised at C-4'. Biotransformation of 7-O-methylglabranin (2) proceeded via oxidation of the prenyl group and C-4' by the same fungi, and the obtention of 11 mimics the biosynthesis of this last compound. Some compounds displayed moderate antiproliferative activity against selected human cancer cell lines, with glabranin being the most active, suggesting that the prenyl group and the phenol at C-7 are important structural determinants for cytotoxicity.