HPLC-VIS chromatograms of extracts of authentic mirtocyan (A) and of plasma (B), urine (C), or colorectal tumor tissue (D) from patients who received 1.4.

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HPLC-VIS chromatograms of extracts of authentic mirtocyan (A) and of plasma (B), urine (C), or colorectal tumor tissue (D) from patients who received 1.4 (i), 2.8 (ii), or 5.6 grams (iii) of mirtocyan daily for 7 d; and identification by HPLC-MS/MS of major... HPLC-VIS chromatograms of extracts of authentic mirtocyan (A) and of plasma (B), urine (C), or colorectal tumor tissue (D) from patients who received 1.4 (i), 2.8 (ii), or 5.6 grams (iii) of mirtocyan daily for 7 d; and identification by HPLC-MS/MS of major anthocyanin species in extracts of tumor tissue (E) and urine (F) from patients on 5.6 grams of mirtocyan. Inset, structures of anthocyanins contained in mirtocyan; glycosidic sugars are attached via C3 in the anthocyanidin. Traces represent representative samples (B and C) of 10 (low dose, i), 8 (medium dose, ii), or 7 patients (high dose, iii), or pooled tumor tissue samples (D) of 4 (i) or 5 patients (ii and iii). iv, samples of predose “control” biofluids (A and B) and for tumor tissue. D, pooled presurgery biopsy samples. Numbers below/above peaks in A and B identify mirtocyan anthocyanin species (by HPLC-MS/MS and comparison with chromatographic data in the Indena datasheet) as follows: 1, delphinidin-3-galactoside; 2, delphinidin-3-glucoside; 3, cyanidin-3-galactoside; 4, delphinidin-3-arabinoside; 5, cyanidin-3-glucoside; 6, petunidin-3-galactoside; 7, cyanidin-3-arabinoside; 8, petunidin-3-glucoside; 9, peonidin-3-galactoside; 10, petunidin-3-arabinoside; 11, peonidon-3-glucoside; 12, malvidin-3-galactoside; 13, peonidon-3-arabinoside; 14, malvidin-3-glucoside; 15, malvidin-3-arabinoside. Peonidin-3-glucoside (compound 11) is the major anthocyanin in plasma (B). Arrows, major anthocyanin species in urine (C) and tumor (D), which were identified by HPLC-MS/MS with SRM (E and F). Extracts of pooled tissue from 5 patients in E, and of one urine sample representative of 7 patients in F were analyzed for 28 mass transitions spanning conceivable anthocyanins and metabolites generated by methylation, glucuronidation, and sulfation of mirtocyan anthocyanins. Top traces in E and F show peaks at specific mass transitions, and bottom traces total ion chromatogram (E) or composite chromatogram of all 28 channel transitions (F). Transition m/z 463>331 characterizes the major peak in tumor tissue (E) as methylpetunidin arabinoside or isomeric dimethyldelphinidin arabinoside (Rt, 9.0 min), with a less abundant peak for malvidin-3-arabinoside (Rt, 13.8). Transition m/z 477>301 identifies the most abundant species in urine (F) as peonidin glucuronide/methylcyanidin glucuronide (Rt, 12-13 min; two species). Note that chromatographic conditions (column length, detector) in E and F differed from those used to yield the results shown in A to D; therefore, there are slight discrepancies in retention time. Sarah Thomasset et al. Cancer Prev Res 2009;2:625-633 ©2009 by American Association for Cancer Research