Axially Chiral Dimeric Naphthalene and Naphthoquinone Metabolites, from Root Cultures of the West African Liana Triphyophyllum peltatum

• Published in: Journal of natural products (Washington, D.C.) Vol. 79; no. 8; pp. 2094 - 2103
• Main Authors: Bringmann, Gerhard, Irmer, Andreas, Büttner, Tobias, Schaumlöffel, Anu, Zhang, Guoliang, Seupel, Raina, Feineis, Doris, Fester, Karin
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society and American Society of Pharmacognosy 26-08-2016
• Subjects: Africa, Western; Alkaloids - chemistry; Alkaloids - isolation & purification; Dioncophyllaceae - chemistry; Isoquinolines - chemistry; Molecular Structure; Naphthalenes - chemistry; Naphthalenes - isolation & purification; Naphthoquinones - chemistry; Naphthoquinones - isolation & purification; Plant Extracts; Plant Roots - chemistry
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/acs.jnatprod.6b00439

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).