title: Hybrid stereoisomers of a compact molecular probe based on a jasmonic acid glucoside: syntheses and biological evaluations.
abstract: 12-O-β-D-glucopyranosyl jasmonic acid (JAG) shows unique biological activities, including leaf-closing of Samanea saman. It is expected that the mode of action for such regulation is distinct from that of other jasmonates. We developed high-performance compact molecular probes (CMPs) based on JAG that can be used for the FLAG-tagging of JAG target. We synthesized four hybrid-type JAG-CMP stereoisomers (7, ent-7, 8, and ent-8), which are composed of (-)-12-OH-JA (2)/D-galactopyranoside, (-)-2/L-galactopyranoside, (+)-ent-2/d-galactopyranoside, and (+)-ent-2/L-galactopyranoside moieties, respectively, and we examined their biological features, such as the stereospecific induction of shrinkage, rate of the cellular response, and dependence on potassium channel activity. These features of the JAG-CMPs were completely consistent with those of the original JAG. These results indicate the biological equivalence of JAG and the JAG-CMPs. During the course of such biological evaluations, it was revealed that the biological activity of the CMPs is greatly dependent on the d/l-stereochemistry of a glycon moiety. To the best of our knowledge, this is the first study suggesting that the d/l-stereochemistry of the glycon moiety significantly affects the biological activity of the associated glycoside.
authors.affiliation: Department of Chemistry, Tohoku University, 6-3 Aramaki-aza Aoba, Aoba-ku, Sendai 980-8578, Japan. ueda@m.tohou.ac.jp
authors.forename: Minoru
authors.initials: M
authors.lastname: Ueda
authors.forename: Gangqiang
authors.initials: G
authors.lastname: Yang
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Ishimaru
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Itabashi
authors.forename: Satoru
authors.initials: S
authors.lastname: Tamura
authors.forename: Hiromasa
authors.initials: H
authors.lastname: Kiyota
authors.forename: Shigefumi
authors.initials: S
authors.lastname: Kuwahara
authors.forename: Sho
authors.initials: S
authors.lastname: Inomata
authors.forename: Mitsuru
authors.initials: M
authors.lastname: Shoji
authors.forename: Takeshi
authors.initials: T
authors.lastname: Sugai
mesh_terms: D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*; D007887:Fabaceae / Q000166:cytology / Q000378:metabolism*; D005960:Glucosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*; D015335:Molecular Probes / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D054883:Oxylipins / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*; D010937:Plant Growth Regulators / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism*; D010940:Plant Proteins / Q000378:metabolism; D015221:Potassium Channels / Q000378:metabolism; D011523:Protoplasts / Q000166:cytology; D013237:Stereoisomerism
chemical_list: D003517:Cyclopentanes; D005960:Glucosides; D015335:Molecular Probes; D054883:Oxylipins; D010937:Plant Growth Regulators; D010940:Plant Proteins; D015221:Potassium Channels; C011006:jasmonic acid