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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.

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