The biosynthesis of 8-phenylphenalenones from Eichhornia crassipes involves a putative aryl migration step.
The first compounds of the novel 8-phenylphenalenone type were isolated from roots and leaves of Eichhornia crassipes (Pontederiaceae). The structures were elucidated by spectrometric methods including 1D and 2D NMR analysis. The incorporation of two molecules of [1-13C]phenylalanine provides experimental evidence for the biosynthesis of the 8-phenylphenalenones. A biosynthetic pathway via diarylheptanoid and 9-phenylphenalenone intermediates, including a 1,2-aryl migration, is proposed.
Hölscher
Dirk
D
Max-Planck-Institute for Chemical Ecology, Beutenberg Campus, Hans-Knöll-Str. 8, D-07745 Jena, Germany.
Schneider
Bernd
B
D031806:Eichhornia / Q000737:chemistry / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D043803:Phenalenes / Q000737:chemistry; D018515:Plant Leaves / Q000737:chemistry; D018517:Plant Roots / Q000737:chemistry
C498103:2-hydroxy-8-(3,4-dihydroxyphenyl)-phenalen-1-one; C498102:2-hydroxy-8-(4-hydroxyphenyl)-phenalen-1-one; D043803:Phenalenes