title: Synthesis of (3S,3'S)- and meso-stereoisomers of alloxanthin and determination of absolute configuration of alloxanthin isolated from aquatic animals.
abstract: In order to determine the absolute configuration of naturally occurring alloxanthin, a HPLC analytical method for three stereoisomers 1a-c was established by using a chiral column. Two authentic samples, (3S,3'S)- and meso-stereoisomers 1b and 1c, were chemically synthesized according to the method previously developed for (3R,3'R)-alloxanthin (1a). Application of this method to various alloxanthin specimens of aquatic animals demonstrated that those isolated from shellfishes, tunicates, and crucian carp are identical with (3R,3'R)-stereoisomer 1a, and unexpectedly those from lake shrimp, catfish, biwa goby, and biwa trout are mixtures of three stereoisomers of 1a-c.
authors.affiliation: Kobe Pharmaceutical University, Motoyamakita-machi, Higashinada-ku, Kobe 658-8558, Japan. y-yamano@kobepharma-u.ac.jp.
authors.forename: Yumiko
authors.initials: Y
authors.lastname: Yamano
authors.affiliation: Research Institute for Production Development, 15 Shimogamo-morimoto-cho, Sakyo-ku, Kyoto 606-0805, Japan. maoka@mbox.kyoto-inet.or.jp.
authors.forename: Takashi
authors.initials: T
authors.lastname: Maoka
authors.affiliation: Kobe Pharmaceutical University, Motoyamakita-machi, Higashinada-ku, Kobe 658-8558, Japan. a-wada@kobepharma-u.ac.jp.
authors.forename: Akimori
authors.initials: A
authors.lastname: Wada
mesh_terms: D000818:Animals; D049872:Bivalvia; D003445:Crustacea; D005399:Fishes; D008968:Molecular Conformation; D008974:Mollusca; D013237:Stereoisomerism; D014561:Urochordata; D024341:Xanthophylls / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D024341:Xanthophylls; C006462:alloxanthin