Preparative-scale fermentation of gallic acid (3,4,5-trihydroxybenzoic acid) ( 1) with Beauveria sulfurescens ATCC 7159 gave two new glucosidated compounds, 4-(3,4-dihydroxy-6-hydroxymethyl-5-methoxy-tetrahydro-pyran-2-yloxy)-3-hydroxy-5-methoxy-benzoic acid ( 4), 3-hydroxy-4,5-dimethoxy-benzoic acid 3,4-dihydroxy-6-hydroxymethyl-5-methoxy-tetrahydro-pyran-2-yl ester ( 7), along with four known compounds, 3- O-methylgallic acid ( 2), 4- O-methylgallic acid ( 3), 3,4- O-dimethylgallic acid ( 5), and 3,5- O-dimethylgallic acid ( 6). The new metabolite genistein 7- O-β-D-4″- O-methyl-glucopyranoside ( 8) was also obtained as a byproduct due to the use of soybean meal in the fermentation medium. The structural elucidation of the metabolites was based primarily on 1D-, 2D-NMR, and HRFABMS analyses. Among these compounds, 2, 3, and 5 are metabolites of gallic acid in mammals. This result demonstrated that microbial culture parallels mammalian metabolism; therefore, B. sulfurescens might be a useful tool for generating mammalian metabolites of related analogs of gallic acid ( 1) for complete structural identification and for further use in investigating pharmacological and toxicological properties in this series of compounds. In addition, a GRE (glucocorticoid response element)-mediated luciferase reporter gene assay was used to initially screen for the biological activity of the 6 compounds, 2– 6 and 8, along with 1 and its chemical O-methylated derivatives 9– 13. Among the 12 compounds tested, 11– 13 were found to be significant, but less active than the reference compounds of methylprednisolone and dexamethasone. [ABSTRACT FROM AUTHOR]