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

详细信息    查看全文

• 作者：Gerhard Bringmann ; Andreas Irmer ; Tobias Büttner ; Anu Schaumlöffel ; Guoliang Zhang ; Raina Seupel ; Doris Feineis ; Karin Fester
• 刊名：Journal of Natural Products
• 出版年：2016
• 出版时间：August 26, 2016
• 年：2016
• 卷：79
• 期：8
• 页码：2094-2103
• 全文大小：618K
• 年卷期：0
• ISSN：1520-6025

文摘

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).