Characterization of a helminthosporic acid analog that is a selective agonist of gibberellin receptor

Sho Miyazaki, Kenji Tomita, Hisakazu Yamane, Masatomo Kobayashi, Tadao Asami, Masatoshi Nakajima

Research output: Contribution to journalArticle

Abstract

Helminthosporol, a natural growth regulator isolated from a fungus, stimulates hypocotyl growth and seed germination, similar to gibberellin (GA). We recently reported that helminthosporic acid (H-acid), a synthetic analog of helminthosporol, acts as an agonist of GA receptor. In this study, we showed that a H-acid analog, in which the hydroxymethyl group at the C-8 position of H-acid was converted to a keto group, acts as a selective GA receptor agonist. 1) This analog shows higher hypocotyl elongation activity in Arabidopsis than H-acid does, and induces the degradation of DELLA protein and 2) leads to the formation of the GID1-DELLA complex and 3) regulates the expression of GA-related genes. In addition, 4) its hypocotyl elongation activity was not observed in a atgid1a single mutant, and 5) this analog could promote only the interaction between specific GA receptors and DELLA proteins in vitro. Taken together, our results strongly suggest that the selectivity of the reported H-acid analog depends on the specificity of its GA receptor binding activity.

Original languageEnglish
Pages (from-to)2465-2470
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume28
Issue number14
DOIs
Publication statusPublished - 2018 Aug 1

Fingerprint

Gibberellins
Hypocotyl
Elongation
Growth
Germination
Fungi
Arabidopsis
Proteolysis
Seed
Seeds
Proteins
Genes
helminthosporic acid
Degradation

Keywords

  • GA-like
  • GID1
  • Natural product
  • Plant hormone
  • Selectivity
  • Terpenoid

ASJC Scopus subject areas

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

Cite this

Characterization of a helminthosporic acid analog that is a selective agonist of gibberellin receptor. / Miyazaki, Sho; Tomita, Kenji; Yamane, Hisakazu; Kobayashi, Masatomo; Asami, Tadao; Nakajima, Masatoshi.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 28, No. 14, 01.08.2018, p. 2465-2470.

Research output: Contribution to journalArticle

Miyazaki, Sho ; Tomita, Kenji ; Yamane, Hisakazu ; Kobayashi, Masatomo ; Asami, Tadao ; Nakajima, Masatoshi. / Characterization of a helminthosporic acid analog that is a selective agonist of gibberellin receptor. In: Bioorganic and Medicinal Chemistry Letters. 2018 ; Vol. 28, No. 14. pp. 2465-2470.
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