title: Functional importance of the sugar moiety of jasmonic acid glucoside for bioactivity and target affinity.
abstract: 12-O-β-D-Glucopyranosyljasmonic acid (JAG, 1) induces nyctinastic leaf-folding of Samanea saman. The SAR studies of 1 revealed the unique role of its glycone moiety. Biological activity and the target affinity of 1 were affected by the stereochemistry of the glycone moiety. JAG belongs to a unique class of ligands in which the structure of the glycone moiety is involved in the molecular recognition by the target protein.
authors.affiliation: Laboratory of Organic Chemistry, Department of Chemistry, Tohoku University, 6-3 Aramaki-Aza Aoba, Aoba-ku, Sendai 980-8578, Japan. ueda@m.tohoku.ac.jp.
authors.forename: Minoru
authors.initials: M
authors.lastname: Ueda
authors.forename: Gangqiang
authors.initials: G
authors.lastname: Yang
authors.forename: Yuuki
authors.initials: Y
authors.lastname: Nukadzuka
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Ishimaru
authors.forename: Satoru
authors.initials: S
authors.lastname: Tamura
authors.forename: Yoshiyuki
authors.initials: Y
authors.lastname: Manabe
mesh_terms: D031289:Albizzia / Q000737:chemistry; D002236:Carbohydrate Conformation; D003517:Cyclopentanes / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry* / Q000378:metabolism*; D008958:Models, Molecular; D054883:Oxylipins / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013816:Thermodynamics
chemical_list: D003517:Cyclopentanes; D005960:Glucosides; D054883:Oxylipins; C011006:jasmonic acid