ARTICLE TITLE:

REFERENCE TYPE:

AUTHOR(S):

EDITOR(S):

PUBLICATION DATE:

PUBLICATION TITLE:

VOLUME:

PAGES:

ABSTRACT:

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

Journal Article

Bringmann G; Irmer A; Büttner T; Schaumlöffel A; Zhang G

2016

Journal of Natural Products

79

2094-2103

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).

URL:

Support

The Liana Ecology Project is supported by Marquette University and funded in part by the National Science Foundation.