title: Age-dependent changes from allylphenol to prenylated benzoic acid production in Piper gaudichaudianum Kunth.
abstract: HPLC-DAD and principal component analysis (PCA) of the (1)H NMR spectrum of crude plant extracts showed high chemical variability among seedlings and adult organs of Piper gaudichaudianum. While gaudichaudianic acid was the major compound in the adult leaves, apiole and dillapiole were the major compounds in their seedling leaves. By the 15th month of seedling growth, the levels of apiole and dillapiole decreased and gaudichaudianic acid appeared along with two compounds, biosynthetically related to gaudichaudianic acid.
authors.affiliation: Research Support Center in Molecular Diversity of Natural Products, Institute of Chemistry, University of São Paulo, Av. Prof. Lineu Prestes, 748, 05508-000 São Paulo, SP, Brazil.
authors.forename: Anderson M
authors.initials: AM
authors.lastname: Gaia
authors.affiliation: Research Support Center in Molecular Diversity of Natural Products, Institute of Chemistry, University of São Paulo, Av. Prof. Lineu Prestes, 748, 05508-000 São Paulo, SP, Brazil.
authors.forename: Lydia F
authors.initials: LF
authors.lastname: Yamaguchi
authors.affiliation: Department of Chemistry, University of Nevada, Reno, NV 89557, USA.
authors.forename: Christopher S
authors.initials: CS
authors.lastname: Jeffrey
authors.affiliation: Research Support Center in Molecular Diversity of Natural Products, Institute of Chemistry, University of São Paulo, Av. Prof. Lineu Prestes, 748, 05508-000 São Paulo, SP, Brazil. Electronic address: majokato@iq.usp.br.
authors.forename: Massuo J
authors.initials: MJ
authors.lastname: Kato
mesh_terms: D000498:Allyl Compounds; D001565:Benzoates / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D004149:Dioxoles / Q000737:chemistry; D015394:Molecular Structure; D031701:Piper / Q000737:chemistry* / Q000254:growth & development; D010936:Plant Extracts / Q000737:chemistry; D018515:Plant Leaves / Q000737:chemistry; D025341:Principal Component Analysis; D000081248:Allylbenzene Derivatives
chemical_list: D000498:Allyl Compounds; D001565:Benzoates; D004149:Dioxoles; D010936:Plant Extracts; C494629:gaudichaudianic acid; C498255:5-allyl 6,7-dimethoxy 1,3-benzodioxole; C446539:apiole; D000081248:Allylbenzene Derivatives
keywords: Apiole; Biosynthetic intermediates; Dillapiole; Gaudichaudianic acid; Ontogeny; Piper gaudichaudianum; Piperaceae