Absolute structure of N-p-coumaroyloctopamine in elicitor-treated potato tuber tissue.
Treatment of potato tuber tissue with beta-1,3-oligoglucosaccharide causes an accumulation of N-p-coumaroyloctopamine (1). In order to determine the absolute structure of 1 in potato, optically active 1 was synthesized from (R)-octopamine which had been obtained from the racemic mixture by the fractional crystallization. By comparing the chromatographic behavior of synthetic and naturally-occurring samples with a chiral HPLC analysis, the absolute configuration of 1 in potato was determined to be S. This indicates that the absolute configuration of the octopamine moiety of 1 is opposite to that of octopamine formed in animal tissues.
Matsuda
F
F
Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Japan. matsuda@colorado.kais.kyoto-u.ac.jp
Miyagawa
H
H
Ueno
T
T
D003373:Coumaric Acids / Q000737:chemistry*; D015394:Molecular Structure; D009655:Octopamine / Q000031:analogs & derivatives* / Q000737:chemistry*; D009844:Oligosaccharides; D011198:Solanum tuberosum / Q000737:chemistry*
D003373:Coumaric Acids; C410948:N-4-coumaroyloctopamine; D009844:Oligosaccharides; D009655:Octopamine