Transformation of curcumin and analogs 1–5 in STC-1 cells. Cells were incubated with compounds (20 μM) for 2 h, extracted, and analyzed by LC-ESI-MS. (A) Selected reaction monitoring chromatograms of curcumin (C), bicyclopentadione (BCP), curcumin-glucuronide (C-G) and their respective hexadeuterated (d6) standards. The ion transitions monitored are listed in Materials and Methods. (B) Extracted ion chromatograms for 1, dioxygenated 1 (1 + 32), as well as curcumin and BCP derived from transformation of 1 in STC-1 cells. (C) Extracted ion chromatograms for 2, 3, and their respective dioxygenated transformation products (M + 32). (D) Extracted ion chromatograms for 4, 5, and their respective monooxygenated transformation products (M + 16).