Syntheses and novel bioactivities of 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

20 Citations (Scopus)

Abstract

Potassium lespedezate (1) is the leaf-opening substance of a nyctinastic plant, Lespedeza cuneata G. Don. We have synthesized two sugar-derivatives of 1, potassium galactolespedezate (4) and mannolespedezate (6). Both 4 and 6 were quite effective for the leaf-opening of Cassia. mimosoides at 8 x 10-7 M, as strong as 1. However, 1 kept the leaf open only for a few days; on the other hand, 4 and 6 kept the leaf open after a week at that concentration. Additionally, remarkable difference was observed in the rate of enzymatic hydrolysis of natural and artificial leaf-opening sustance by using commercially available β-glucosidase. Therefore, 4 and 6 would not be hydrolized in the plant body, and are potentially useful molecular probes for the studies of the control of the nyctinastic leaf-movement by a biological clock.

Original languageEnglish
Pages (from-to)10925-10936
Number of pages12
JournalTetrahedron
Volume55
Issue number36
DOIs
Publication statusPublished - 1999 Sep 3
Externally publishedYes

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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