On the structure of calonyctin A, a plant growth regulator

Carbohydr Res. 1993 Jul 19;245(2):259-70. doi: 10.1016/0008-6215(93)80076-q.

Abstract

The plant growth regulator calonyctin A, isolated from the dried leaves of Calonyction aculeatum L. House (Yue-Guang-Hua), was separated into two pure components by high performance liquid chromatography. By use of mass spectrometry based on various ionization techniques, one- and two-dimensional NMR spectroscopy, IR spectrometry, and chemical methods the molecular structures of the two homologous glycosides were determined. Each molecule contains two hydroxy fatty acid residues and four 6-deoxyhexose units. The fatty acids are 3-hydroxy-2-methylbutanoic acid and 11-hydroxytetradecanoic acid or 11-hydroxyhexadecanoic acid. The 6-deoxyhexose residues (three of quinovose and one of rhamnose) comprise a tetrasaccharide having the following structure: [formula: see text] The long-chain hydroxy acid is linked glycosidically through its O-11 to Qui D and esterified to O-2 of Qui C, forming a macrocyclic lactone. The 3-hydroxy-2-methylbutanoic acid is ester-linked to O-3 of Qui C.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Chromatography, High Pressure Liquid
  • Lactones / chemistry*
  • Lactones / isolation & purification
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Oligosaccharides / chemistry*
  • Oligosaccharides / isolation & purification
  • Plant Growth Regulators / chemistry*
  • Plants / chemistry

Substances

  • Lactones
  • Oligosaccharides
  • Plant Growth Regulators
  • calonyctin A-2d
  • calonyctin A-2b