Hybrid stereoisomers of a compact molecular probe based on a jasmonic acid glucoside: Syntheses and biological evaluations

Minoru Ueda, Gangqiang Yang, Yasuhiro Ishimaru, Tetsuya Itabashi, Satoru Tamura, Hiromasa Kiyota, Shigefumi Kuwahara, Sho Inomata, Mitsuru Shoji, Takeshi Sugai

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8 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)5832-5843
Number of pages12
JournalBioorganic and Medicinal Chemistry
Volume20
Issue number19
DOIs
Publication statusPublished - Oct 1 2012
Externally publishedYes

Keywords

  • Enatiodifferential approach
  • Ion channel activation
  • Jasmonic acid glucoside
  • Molecular probe

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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    Ueda, M., Yang, G., Ishimaru, Y., Itabashi, T., Tamura, S., Kiyota, H., Kuwahara, S., Inomata, S., Shoji, M., & Sugai, T. (2012). Hybrid stereoisomers of a compact molecular probe based on a jasmonic acid glucoside: Syntheses and biological evaluations. Bioorganic and Medicinal Chemistry, 20(19), 5832-5843. https://doi.org/10.1016/j.bmc.2012.08.003