title: On the structure of calonyctin A, a plant growth regulator.
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.
authors.affiliation: Institute of Chemistry, Academia Sinica, Beijing, China.
authors.forename: Y
authors.initials: Y
authors.lastname: Fang
authors.forename: W
authors.initials: W
authors.lastname: Chai
authors.forename: S
authors.initials: S
authors.lastname: Chen
authors.forename: Y
authors.initials: Y
authors.lastname: He
authors.forename: L
authors.initials: L
authors.lastname: Zhao
authors.forename: J
authors.initials: J
authors.lastname: Peng
authors.forename: H
authors.initials: H
authors.lastname: Huang
authors.forename: B
authors.initials: B
authors.lastname: Xin
mesh_terms: D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002851:Chromatography, High Pressure Liquid; D007783:Lactones / Q000737:chemistry* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000737:chemistry* / Q000302:isolation & purification; D010937:Plant Growth Regulators / Q000737:chemistry*; D010944:Plants / Q000737:chemistry
chemical_list: D007783:Lactones; D009844:Oligosaccharides; D010937:Plant Growth Regulators; C083072:calonyctin A-2d; C083071:calonyctin A-2b