title: Structural elucidation and biological fate of two glucuronyl metabolites of pelargonidin 3-O-β-D-glucopyranoside in rats.
abstract: A high proportion of pelargonidin 3-O-β-D-glucopyranoside (Pg3G) is metabolized to glucuronides and excreted in mammal urine after ingestion of strawberry fruit, suggesting that these metabolites play important functional roles in vivo. The aim of the present study was to elucidate the structures and determine the biological fate of the two dominant metabolites of Pg3G in rats to enable an accurate discussion of the biological properties of anthocyanins. Authentic Pg3G was orally administered to rats. One pelargonidin monoglucuronide and three Pg3G-monoglucuronides (glucuronides of the glucoside) were identified together with intact Pg3G in both blood plasma and urine samples. The structures of the two dominant metabolites were elucidated as pelargonidin 3-O-β-D-glucuronide (Pg3GlcA) and pelargonidin 3-O-β-D-glucuronyl-(1→2)-β-D-glucoside by means of (1)H and (13)C nuclear magnetic resonance spectroscopy and heteronuclear multiple-bond connective spectroscopy. The bioavailability of Pg3G in its intact form was 0.31% of the orally administered dose, and 0.65% was absorbed in the Pg3GlcA form.
authors.affiliation: Faculty of Pharmaceutical Sciences, Niigata University of Pharmacy and Applied Life Sciences, Akiha-ku, Niigata, Japan. ichiyanagi@niit.ac.jp
authors.forename: Takashi
authors.initials: T
authors.lastname: Ichiyanagi
authors.forename: Yoshiki
authors.initials: Y
authors.lastname: Kashiwada
authors.forename: Yasuo
authors.initials: Y
authors.lastname: Shida
authors.forename: Michiko
authors.initials: M
authors.lastname: Sekiya
authors.forename: Yoshihiko
authors.initials: Y
authors.lastname: Hatano
authors.forename: Yoshihisa
authors.initials: Y
authors.lastname: Takaishi
authors.forename: Yasumasa
authors.initials: Y
authors.lastname: Ikeshiro
mesh_terms: D000042:Absorption; D000284:Administration, Oral; D000818:Animals; D000872:Anthocyanins / Q000097:blood / Q000737:chemistry* / Q000652:urine; D001682:Biological Availability; D004305:Dose-Response Relationship, Drug; D031985:Fragaria / Q000737:chemistry; D005638:Fruit / Q000737:chemistry; D020719:Glucuronides / Q000097:blood / Q000652:urine; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051381:Rats; D017208:Rats, Wistar
chemical_list: D000872:Anthocyanins; D020719:Glucuronides; C066957:pelargonidin; C078485:pelargonidin-3-glucoside