New Antiglycative Compounds from Cumin (Cuminum cyminum) Spice

Cumin (Cuminum cyminum L.), a widely consumed food spice, has been reported to have antiglycative effects in vitro and in vivo, but there is a paucity of data on its bioactive compounds. Herein, we report the isolation and structure elucidation (by NMR, HRESIMS, and CD) of 21 (1-21) compounds from a methanol extract of cumin seeds. The isolates included five new compounds: two sesquiterpenoids, two pairs of monoterpeneoid epimers, and a chalcone, named cuminoids A-E, respectively. The isolates were evaluated for antiglycative effects using the bovine serum albumin-fructose intrinsic fluorescence assay. At equivalent concentrations, several of the isolates, including cuminoids C-E, were more potent inhibitors than the positive control, aminoguanidine, a synthetic antiglycative agent (>50 vs 35%, respectively).