title: Axially Chiral Dimeric Naphthalene and Naphthoquinone Metabolites, from Root Cultures of the West African Liana Triphyophyllum peltatum.
abstract: Root cultures of the West African liana Triphyophyllum peltatum were initiated from stem explants of in vitro cultivated shoots. From these organ cultures, three new binaphthalenes, one binaphthoquinone, and two (bi)naphthalene glucosides were isolated, with substitution patterns related to those of the naphthylisoquinoline alkaloids, which are the "normal" main metabolites of T. peltatum. The structures of the diglucoside dioncoquinoside A (1) and of the axially chiral biaryls triphyoquinols A1 (3), A2 (4), and B (5), triphyoquinoside A (6), and triphyoquinone A (7) were elucidated by spectroscopic analysis (HRESIMS, 1D and 2D NMR) and by application of electronic circular dichroism (ECD) spectroscopy in combination with the exciton chirality method and quantum-chemical ECD calculations. The root cultures likewise produced the known alkaloids dioncophylline A (8), 5'-O-demethyldioncophylline A (9), dioncopeltine A (10), habropetaline A (11), and 5'-O-methyldioncophylline D (12a/b), the naphthalene glucoside plumbaside A (2), and the naphthoquinones plumbagin (13), droserone (14), and 8-hydroxydroserone (15).
authors.affiliation: Institute of Organic Chemistry, University of Würzburg , Am Hubland, D-97074 Würzburg, Germany.
authors.forename: Gerhard
authors.initials: G
authors.lastname: Bringmann
authors.affiliation: Institute of Organic Chemistry, University of Würzburg , Am Hubland, D-97074 Würzburg, Germany.
authors.forename: Andreas
authors.initials: A
authors.lastname: Irmer
authors.affiliation: Institute of Organic Chemistry, University of Würzburg , Am Hubland, D-97074 Würzburg, Germany.
authors.forename: Tobias
authors.initials: T
authors.lastname: Büttner
authors.affiliation: Institute of Organic Chemistry, University of Würzburg , Am Hubland, D-97074 Würzburg, Germany.
authors.forename: Anu
authors.initials: A
authors.lastname: Schaumlöffel
authors.affiliation: Institute of Organic Chemistry, University of Würzburg , Am Hubland, D-97074 Würzburg, Germany.
authors.forename: Guoliang
authors.initials: G
authors.lastname: Zhang
authors.affiliation: Institute of Organic Chemistry, University of Würzburg , Am Hubland, D-97074 Würzburg, Germany.
authors.forename: Raina
authors.initials: R
authors.lastname: Seupel
authors.affiliation: Institute of Organic Chemistry, University of Würzburg , Am Hubland, D-97074 Würzburg, Germany.
authors.forename: Doris
authors.initials: D
authors.lastname: Feineis
authors.affiliation: Institute of Pharmacy, Research Group Pharmaceutical Biology, University of Leipzig , Johannisallee 21-23, D-04103 Leipzig, Germany.
authors.forename: Karin
authors.initials: K
authors.lastname: Fester
mesh_terms: D000354:Africa, Western; D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D045603:Dioncophyllaceae / Q000737:chemistry*; D007546:Isoquinolines / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry / Q000302:isolation & purification*; D009285:Naphthoquinones / Q000737:chemistry / Q000302:isolation & purification*; D010936:Plant Extracts; D018517:Plant Roots / Q000737:chemistry
chemical_list: D000470:Alkaloids; D007546:Isoquinolines; D009281:Naphthalenes; D009285:Naphthoquinones; D010936:Plant Extracts; C439391:hydroxydroserone; C104320:dioncophylline A; C014758:plumbagin