Pig caecum was used under anaerobic conditions to metabolize flavonoids from several classes, i.e., chrysin 1, naringenin 2, quercetin 3, and hesperetin 4. Whereas chrysin 1 was not converted by the pig intestinal flora under the experimental conditions used, naringenin 2 was transformed to 3-(4-hydroxyphenyl)-propionic acid and 3-phenylpropionic acid. Quercetin 3 was metabolized to phloroglucinol, 3,4-dihydroxyphenylacetic acid, and 3,4-dihydroxytoluene. Hesperetin 4 was degraded via eriodictyol to 3-(3-hydroxyphenyl)-propionic acid and phloroglucinol. Structural elucidation of the formed metabolites was performed by high-performance liquid chromatography--diode array detection (HPLC-DAD) as well as HPLC-electrospray ionization--mass spectrometry (ESI-MS (MS)) and high resolution gas chromatography-mass spectrometry (HRGC-MS) analyses. The time course of microbial conversion of 2-4 was determined by HPLC-DAD analysis, revealing slow degradation of 2 and rapid transformation of 3 and 4. The results lead to the conclusion that the pig caecum model is a suitable ex vivo model for studying the intestinal degradation of flavonoids.