Biosynthetic origins of the isoprene units of gaudichaudianic acid in Piper gaudichaudianum (Piperaceae).
The biosynthesis of (2S)-2-methyl-2-(4'-methyl-3'-pentenyl)-8-(3''-methyl-2-butenyl)-2H-1-benzopyran-6-carboxylic acid (gaudichaudianic acid), the major metabolite in leaves and roots of Piper gaudichaudianum Kunth (Piperaceae), has been investigated employing [1-(13)C]-D-glucose as precursor. The labelling pattern in the isolated gaudichaudianic acid was determined by quantitative (13)C NMR spectroscopy analysis and was consistent with involvement of both mevalonic acid and 2-C-methyl-D-erythritol-4-phosphate pathways in the formation of the dimethylallyl- and geranyl-derived moieties. The results confirmed that both plastidic and cytoplasmic pathways are able to provide isopentenyl diphosphate units for prenylation of p-hydroxybenzoic acid.
Lopes
Adriana A
AA
Instituto de Química, Universidade Estadual Paulista, C.P. 355, CEP 14801-970 Araraquara, SP, Brazil.
Baldoqui
Debora C
DC
López
Silvia N
SN
Kato
Massuo J
MJ
Bolzani
Vanderlan da S
Vda S
Furlan
Maysa
M
D001565:Benzoates / Q000302:isolation & purification / Q000378:metabolism*; D004896:Erythritol / Q000031:analogs & derivatives / Q000378:metabolism; D005947:Glucose / Q000378:metabolism; D045782:Hemiterpenes / Q000378:metabolism; D008798:Mevalonic Acid / Q000378:metabolism; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009943:Organophosphorus Compounds / Q000378:metabolism; D031701:Piper / Q000378:metabolism*; D018515:Plant Leaves / Q000378:metabolism; D018517:Plant Roots / Q000378:metabolism; D013403:Sugar Phosphates / Q000378:metabolism; D013729:Terpenes / Q000302:isolation & purification / Q000378:metabolism*
C114232:2-C-methylerythritol 4-phosphate; D001565:Benzoates; D045782:Hemiterpenes; D009943:Organophosphorus Compounds; D013403:Sugar Phosphates; D013729:Terpenes; C494629:gaudichaudianic acid; C004809:isopentenyl pyrophosphate; D005947:Glucose; D004896:Erythritol; D008798:Mevalonic Acid