On the structure of calonyctin A, a plant growth regulator.
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.
Fang
Y
Y
Institute of Chemistry, Academia Sinica, Beijing, China.
Chai
W
W
Chen
S
S
He
Y
Y
Zhao
L
L
Peng
J
J
Huang
H
H
Xin
B
B
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
D007783:Lactones; D009844:Oligosaccharides; D010937:Plant Growth Regulators; C083072:calonyctin A-2d; C083071:calonyctin A-2b