Synthesis and bioactivity of potassium β-D-glucopyranosyl 12-hydroxy jasmonate and related compounds

Yoko Nakamura, Ryoji Miyatake, Sho Inomata, Minoru Ueda

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

Albizzia saman, a leguminous plant, is known to open its leaves in the daytime and sleep at night with the leaves folded. β-D-Glucopyranosyl 12-hydroxyjasmonate (1) was isolated as an endogenous chemical factor controlling this leafmovement. We developed a concise synthesis of optically pure (-)-1 in 9 steps from (+)-2 with a total yield of 58%. Similarly, such analogs of 1 as epi-LCF (13), enantiomer (14), and galactoside (19) were synthesized for a structure activity relationship (SAR) study. The results of this SAR study strongly suggest that the mechanism for the leaf-closing activity of 1 would be different from that of methyl jasmonate, and also suggest the involvement of a different kind of target protein which recognizes the trans-isomer of a jasmonate derivative.

Original languageEnglish
Pages (from-to)2867-2876
Number of pages10
JournalBioscience, Biotechnology and Biochemistry
Volume72
Issue number11
DOIs
Publication statusPublished - 2008

Keywords

  • Albizzia saman
  • Leaf-closing factor
  • Nyctinasty
  • Potassium β-D-glucopyranosyl 12-hydroxy jasmonate
  • Tuberonic acid glucoside

ASJC Scopus subject areas

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis and bioactivity of potassium β-D-glucopyranosyl 12-hydroxy jasmonate and related compounds'. Together they form a unique fingerprint.

Cite this