Synthesis and bioactivity of the gibberellin, 18-hydroxy-GA1 (GA132)

Org Biomol Chem. 2008 Apr 21;6(8):1416-24. doi: 10.1039/b800728d. Epub 2008 Feb 26.

Abstract

As part of a study to confirm putative structural assignments to new gibberellins and to furnish sufficient quantities for biological investigations, a twenty step synthesis of 18-hydroxy GA1 from gibberellic acid (GA3) is described, allowing the confirmation of structure for a new gibberellin, GA132, that occurs in developing grains of barley (Hordeum vulgare). The early part of the sequence involved cleavage of the C(3)-C(4) bond in the A-ring of a 3-oxo intermediate. The ring was then reformed as part of a "domino" process involving the conjugate addition of alkoxide to an alpha-methylene lactone moiety followed by an intramolecular aldol reaction. The bioactivities of the new GA, and its 18-hydroxy-GA4 relative, have been confirmed in dwarf barley growth and alpha-amylase induction assays.

MeSH terms

  • Dose-Response Relationship, Drug
  • Enzyme Activation / drug effects
  • Gibberellins / chemical synthesis*
  • Gibberellins / chemistry
  • Gibberellins / pharmacology*
  • Hordeum / drug effects*
  • Hordeum / growth & development
  • Molecular Conformation
  • Stereoisomerism
  • alpha-Amylases / drug effects*

Substances

  • 18-hydroxygibberellic acid 1
  • Gibberellins
  • gibberellic acid
  • alpha-Amylases