Conversion of DCA and DCA-L by the membrane fraction containing PhcC. DCA and DCA-L (100 μM), respectively, were incubated with the membrane fraction containing PhcC (10 μg of protein/ml) in the presence of 300 μM FAD and 300 μM PMS. Portions of the reaction mixtures containing DCA and DCA-L were collected at the start (A and D) and after 10 min of incubation (B and E). The reaction products were analyzed by LC-MS, and negative-ion ESI-MS spectra of compounds III and IV are shown in panels C and F. An HPLC chromatogram of authentic DCA-AC and its negative-ion ESI-MS spectrum are shown in panels G and H, respectively. (I) Chemical structures of DCA-AC and compound IV [2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-5-(3-oxoprop-1-enyl)-2,3-dihydrobenzofuran-3-carboxylic acid; DCA-LC].