Sugar-derivatives of potassium lespedezate, artificial leaf-opening substances of Lespedeza cuneata G. Don, designed for the bioorganic studies of nyctinasty

Minoru Ueda, Yoshiyuki Sawai, Shosuke Yamamura

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

Potassium lespedezate (1) is the leaf-opening substance of a nyctinastic plant, Lespedeza cuneata G. Don. We synthesized two sugar-derivatives of 1, potassium galactolespedezate (2) and mannoisolespedezate (3). Both 2 and 3 were quite effective for the leaf-opening of L. cuneata, at 8 x 10-7 M, as strong as 1. However, 1 kept the leaf open only for a few days; on the other band, 2 and 3 kept the leaf open after a week at that concentration. Thus, it is assumed that 2 and 3 could not be hydrolyzed by α-glucosidase in the plant body, and are therefore potentially useful molecular probes for the studies of the control of the nyctinastic leaf-movement by a biological clock.

Original languageEnglish
Pages (from-to)3757-3760
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number19
DOIs
Publication statusPublished - 1999 May 7
Externally publishedYes

Keywords

  • Biologically active compounds
  • Glycosidation
  • Glycoside
  • Natural products
  • Plants

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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