title: Phenylbenzoisoquinolindione alkaloids accumulate in stamens of Xiphidium caeruleum Aubl. flowers.
abstract: Xiphidium caeruleum (Haemodoraceae) flower organs such as carpels, pedicels, petals, and stamens were separately investigated for their phytochemical profile. The stamens appeared to be a rich source of previously undescribed phenylbenzoisoquinolindiones, a group of phenylphenalenone-derived alkaloids, also named aza-phenylphenalenones. Nine previously undescribed compounds with an identical aza-phenylphenalenone core structure but different amino acid-derived side chains at position 2 were isolated and their structures elucidated by nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS). In addition, some previously reported phenylbenzoisoquinolindiones, phenylbenzoisochromenones and flavonoids were found in stamens and other parts of the flowers. The specific occurrence of heterocyclic phenylphenalenone-type compounds in X. caeruleum suggests these are involved in physiological or ecological processes.
authors.affiliation: Max-Planck Institut für Chemische Ökologie, Beutenberg Campus, Hans-Knöll-Strasse 8, 07745, Jena, Germany; Jiangsu Key Laboratory for Research and Utilization of Plant Resources, Institute of Botany, Jiangsu Province and Chinese Academy of Sciences, Qianhu Houcun 1, 210014, Nanjing, China.
authors.forename: Yu
authors.initials: Y
authors.lastname: Chen
authors.affiliation: Max-Planck Institut für Chemische Ökologie, Beutenberg Campus, Hans-Knöll-Strasse 8, 07745, Jena, Germany.
authors.forename: Christian
authors.initials: C
authors.lastname: Paetz
authors.affiliation: Max-Planck Institut für Chemische Ökologie, Beutenberg Campus, Hans-Knöll-Strasse 8, 07745, Jena, Germany.
authors.forename: Riya C
authors.initials: RC
authors.lastname: Menezes
authors.affiliation: Max-Planck Institut für Chemische Ökologie, Beutenberg Campus, Hans-Knöll-Strasse 8, 07745, Jena, Germany. Electronic address: schneider@ice.mpg.de.
authors.forename: Bernd
authors.initials: B
authors.lastname: Schneider
mesh_terms: D000470:Alkaloids / Q000032:analysis / Q000737:chemistry; D035264:Flowers / Q000737:chemistry*; D007546:Isoquinolines / Q000737:chemistry / Q000302:isolation & purification*; D019684:Magnoliopsida / Q000033:anatomy & histology / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D013329:Structure-Activity Relationship
chemical_list: D000470:Alkaloids; D007546:Isoquinolines
keywords: Haemodoraceae; Phenylbenzoisochromenones; Phenylbenzoisoquinolinones; Phenylphenalenones; Xiphidium caeruleum