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

研究成果: Article査読

9 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)5832-5843
ページ数12
ジャーナルBioorganic and Medicinal Chemistry
20
19
DOI
出版ステータスPublished - 2012 10月 1

ASJC Scopus subject areas

  • 生化学
  • 分子医療
  • 分子生物学
  • 薬科学
  • 創薬
  • 臨床生化学
  • 有機化学

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