title: Monomethyl ethers of 4,5-dihydroxypipecolic acid from Petaladenium urceoliferum: Enigmatic chemistry of an enigmatic legume.
abstract: Leaves of Petaladenium (Leguminosae), an Amazonian monospecific genus recently revealed as a member of the Amburaneae clade among the earliest-diverging papilionoid legumes, were found to accumulate three monomethyl ethers of 4,5-dihydroxypipecolic acids. These were characterised by spectroscopic means as the (2S,4S,5R) and (2S,4R,5S) epimers of 5-hydroxy-4-methoxypipecolic acid and (2S,4R,5R)-4-hydroxy-5-methoxypipecolic acid. These compounds were not detected in any other genera in the Amburaneae clade or the wider Angylocalyceae-Dipterygeae-Amburaneae (ADA) clade of papilionoid legumes. Hydroxypipecolic acids, however, were detected in leaves of Myrocarpus and Myroxylon (sister genera in the Amburaneae clade), Angylocalyx and Xanthocercis (sister genera in the Angylocalyceae clade) and Monopteryx (Dipterygeae clade), and were also present in Petaladenium. Iminosugars, known to be accumulated by all four genera in the Angylocalyceae clade (Alexa, Angylocalyx, Castanospermum and Xanthocercis), were found to be characteristic of this group within the ADA clade.
authors.affiliation: Royal Botanic Gardens, Kew, Richmond, Surrey TW9 3AB, UK. Electronic address: g.kite@kew.org.
authors.forename: Geoffrey C
authors.initials: GC
authors.lastname: Kite
authors.affiliation: Departamento de Botânica, Instituto de Biologia, Universidade Federal da Bahia, Rua Barão de Geremoabo, s/n, Campus Universitário de Ondina, 40170-115 Salvador, Bahia, Brazil; Programa de Pós-Graduação em Botânica (PPGBot), Universidade Estadual de Feira de Santana, Av. Transnordestina, s/n, Novo Horizonte, 44036-900 Feira de Santana, Bahia, Brazil.
authors.forename: Domingos
authors.initials: D
authors.lastname: Cardoso
authors.affiliation: Royal Botanic Gardens, Kew, Richmond, Surrey TW9 3AB, UK.
authors.forename: Gwilym P
authors.initials: GP
authors.lastname: Lewis
authors.affiliation: Department of Biodiversity, Instituto Nacional de Pesquisas da Amazônia (INPA), Av. André Araújo, 2936, Petrópolis, 69060-001 Manaus, Amazonas, Brazil.
authors.forename: Charles E
authors.initials: CE
authors.lastname: Zartman
authors.affiliation: Programa de Pós-Graduação em Botânica (PPGBot), Universidade Estadual de Feira de Santana, Av. Transnordestina, s/n, Novo Horizonte, 44036-900 Feira de Santana, Bahia, Brazil.
authors.forename: Luciano Paganucci
authors.initials: LP
authors.lastname: de Queiroz
authors.affiliation: Royal Botanic Gardens, Kew, Richmond, Surrey TW9 3AB, UK.
authors.forename: Nigel C
authors.initials: NC
authors.lastname: Veitch
mesh_terms: D007887:Fabaceae / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D015394:Molecular Structure; D010875:Pipecolic Acids / Q000737:chemistry / Q000302:isolation & purification*; D018515:Plant Leaves / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C000599697:4,5-di-hydroxy-pipecolic acid; D010875:Pipecolic Acids
keywords: Iminosugars; Leguminosae; Non-protein amino acids; Petaladenium urceoliferum; Pipecolic acid derivatives; Systematic phytochemistry