Two glucosylated abscisic acid derivates from avocado seeds (Persea americana Mill. Lauraceae cv. Hass).
Phytochemical investigation of avocado seed material (Persea americana Mill., Lauraceae) resulted in the isolation of two glucosylated abscisic acid derivates. One of these was not known as a natural product and can be regarded as a potential 'missing link' in abscisic acid metabolism in plants. After fractionation by high-speed countercurrent chromatography, and multiple steps of column chromatography, structures were elucidated by 1D-, 2D-NMR, electrospray-MS to be the novel beta-d-glucoside of (1'S,6'R)-8'-hydroxyabscisic acid, and (1'R,3'R,5'R,8'S)-epi-dihydrophaseic acid beta-d-glucoside. Absolute configuration was determined by circulardichroism, optical rotation, and by NOE experiments.
del Refugio Ramos
María
M
Institute of Food Chemistry, Technical University of Braunschweig, Schleinitz-Strasse 20, D-38106 Braunschweig, Germany.
Jerz
Gerold
G
Villanueva
Socorro
S
López-Dellamary
Fernando
F
Waibel
Reiner
R
Winterhalter
Peter
P
D000040:Abscisic Acid / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000378:metabolism; D002942:Circular Dichroism; D003377:Countercurrent Distribution; D005960:Glucosides / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D027421:Persea / Q000737:chemistry*; D012639:Seeds / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization
D005960:Glucosides; D000040:Abscisic Acid