title: Effect on both aglycone and sugar moiety towards Phase II metabolism of anthocyanins.
abstract: The effect of sugar moiety on anthocyanin metabolism was studied using anthocyanidin 3-rutinosides (cyanidin 3-O-rutinoside (Cy3R) and delphinidin 3-O-rutinoside (Dp3R)) and 3-O-glucosides (delphinidin 3-O-glucoside (Dp3G)). O-methylated Cy3R and Dp3R were detected in rat blood plasma after oral administration of Cy3R and Dp3R (100mg/kg body weight). On the basis of HPLC retention time and UV-visible spectra together with the data of our previous studies on the hydrophobic metabolites of anthocyanidin 3-O-glucosides, it was concluded that both 3'- and 4'-O-methyl Cy3R were metabolites of Cy3R. On the other hand, only 4'-O-methyl Dp3R was detected as hydrophobic metabolite of Dp3R. A group of hydrophilic metabolites was also detected in rat blood plasma after oral administration of anthocyanins (Dp3G, Cy3R and Dp3R) and their structures were determined to be extended glucuronides and their O-methyl analogues by tandem MS analysis. The amounts of extended glucuronides of Dp3G, Cy3R and Dp3R were less than those of cyanidin 3-O-glucoside (Cy3G) reported in our previous study. On the other hand, anthocyanidin-glucuronides (both cyanidin-glucuronide and delphinidin-glucuronide) were not detected after oral administration of Cy3R, Dp3R and Dp3G. These results indicated that both the type of sugar moiety and stability of aglycone largely affected phase II metabolism of anthocyanins, and also indicated that the type of sugar moiety did not affect the O-methylation metabolism but affected glucuronyl conjugation in both liver and small intestine.
authors.affiliation: Faculty of Pharmaceutical Sciences, Niigata University of Pharmacy and Applied Life Sciences, 265-1, Higashijima, Akiha-ku, Niigata 956-8603, Japan. Electronic address: ichiyan@nupals.ac.jp.
authors.forename: Takashi
authors.initials: T
authors.lastname: Ichiyanagi
authors.affiliation: Department of Engineering MS laboratory, Tokyo University of Pharmacy and Life Sciences, 1432-1, Hachio-ji 192-0392, Japan.
authors.forename: Yasuo
authors.initials: Y
authors.lastname: Shida
authors.affiliation: Faculty of Pharmaceutical Sciences, Niigata University of Pharmacy and Applied Life Sciences, 265-1, Higashijima, Akiha-ku, Niigata 956-8603, Japan.
authors.forename: M Mamunur
authors.initials: MM
authors.lastname: Rahman
authors.affiliation: Faculty of Pharmaceutical Sciences, Niigata University of Pharmacy and Applied Life Sciences, 265-1, Higashijima, Akiha-ku, Niigata 956-8603, Japan.
authors.forename: Michiko
authors.initials: M
authors.lastname: Sekiya
authors.affiliation: Faculty of Applied Life Sciences, Niigata University of Pharmacy and Applied Life Sciences, 265-1, Higashijima, Akiha-ku, Niigata 956-8603, Japan.
authors.forename: Yoshihiko
authors.initials: Y
authors.lastname: Hatano
authors.affiliation: Bioscience Laboratories, Meiji Seika Kaisha Limited, 5-3-1 Chiyoda, Sakado-shi, Saitama 350-0289, Japan.
authors.forename: Hitoshi
authors.initials: H
authors.lastname: Matsumoto
authors.affiliation: Faculty of Applied Life Sciences, Niigata University of Pharmacy and Applied Life Sciences, 265-1, Higashijima, Akiha-ku, Niigata 956-8603, Japan.
authors.forename: Masao
authors.initials: M
authors.lastname: Hirayama
authors.affiliation: Faculty of Applied Life Sciences, Niigata University of Pharmacy and Applied Life Sciences, 265-1, Higashijima, Akiha-ku, Niigata 956-8603, Japan.
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Konishi
authors.affiliation: Faculty of Pharmaceutical Sciences, Niigata University of Pharmacy and Applied Life Sciences, 265-1, Higashijima, Akiha-ku, Niigata 956-8603, Japan.
authors.forename: Yasumasa
authors.initials: Y
authors.lastname: Ikeshiro
keywords: Anthocyanidin 3-O-glucoside; Anthocyanidin 3-O-rutinoside; Cyanidin; Delphinidin; Extended glucuronide; Glucoside–glucuronide; Metabolism; Rutinoside–glucuronide