Antimicrobial properties of S-benzofuran-2-yl ethanol produced by biotransformation

Stephen F Austin State University, Baker Pattillo Student Center, Student Center Theatre and Twilight Ballroom

All living organisms contain enzymes to carry out biological reactions, which produce substances with a specific three dimensional shape. Enantiomers are two molecules that are mirror images of each other just as hands are mirror images of each other. It is well known in the pharmaceutical world that one of the enantiomers (one of the mirrorimage molecules) has a positive biological effect while the other can be harmful or have no effect. Currently, any potential pharmaceutical that could exist as enantiomers must have each enantiomer tested for biological activity prior to FDA approval. In our laboratory, we have focused on one particular reaction in which enzymes in vegetables catalyze a reaction of benzofuranyl methyl ketone (BMK) to benzofuranylethanol (BMA). BMA can have two different three dimensional arrangements, so mirror image molecules are possible. The two enantiomers are designated S-BMA and R-BMA. Several vegetables have been utilized to determine which can catalyze this reaction, as well as to determine whether the various vegetables produce both enantiomers or only a single enantiomer. Several vegetables (carrot, parsnip, and celery) produce only one of the enantiomers, the S-isomer. However, potatoes and radishes produce a mixture of the R- and S-isomer, with the potato producing nearly equal amounts of both. Previous work in the laboratory has shown that the S-BMA produced from carrots has antimicrobial properties, inhibiting the growth of bacteria as well as yeast. Initial studies indicate the mixture of S- and R-BMA from potatoes has less potent antimicrobial activity than the pure S-BMA produced by carrots. Studies are underway to more fully assess the antimicrobial property of the mixture of the R- and S-isomer and compare to the antimicrobial property of the pure S-isomer produced by carrots.