The flavanone glycoside, hesperidin, in orange juice is heavily metabolized to flavanone glucuronides and mixed glucuronide/sulfates as well as a number of flavanone ring-fission products. These latter compounds occurred as the major metabolites of hesperidin in the urine of rats. Hesperidin was administered to adult male Wistar rats (200 mg/day) in the early evening and urine collected overnight. Studies of the metabolites in the urine samples were conducted by HPLC coupled with negative electrospray ionization-mass spectrometry. One main flavanone glucuronide was detected along with two other minor hesperetin-containing compounds. The main ring-fission metabolites were detected at 245, 243, 273, and 275 m/z, with fragment ions at 165, 163, 193, and 195 m/z. Each of these represented neutral losses of 80 amu, consistent with losses of sulfate groups. It is proposed that the fragment ions of 163 and 193 m/z are due to coumaric and ferulic acid groups, and that the 165 and 195 m/z fragment ions originate from substituted phenylpropionic acid conjugates. These compounds are being isolated for chemical structure determinations, for use as standards in pharmacokinetic studies, and analyses of biological actions in mammalian cells.

HPLC-MS of hesperidin metabolites in rat urine

250th National Meeting (2015)

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