Title
Ancistectorine D, a naphthylisoquinoline alkaloid with antiprotozoal and antileukemic activities, and further 5,8′- and 7,1′-linked metabolites from the Chinese liana Ancistrocladus tectorius
Author
Gerhard Bringmann, Raina Seupel, Doris Feineis, Guoliang Zhang, Minjuan Xu, Jun Wu, Marcel Kaiser, Reto Brun, Ean-Jeong Seo, Thomas Efferth
Year
2016
Journal
Fitoterapia
Abstract
From the twigs and stems of the Chinese liana Ancistrocladus tectorius(Ancistrocladaceae), two new 5,8′-coupled naphthylisoquinolines, ancistectorine D (5) and its 6-O-demethyl derivative 6, were isolated, along with two new 7,1′-linked alkaloids, 6-O-methylancistectorine B1 (7) and ancistectorine B2 (8). Two further compounds, ancistroealaine A (4) and 6-O-demethyl-8-O-methyl-7-epi-ancistrobrevine D (10), already known from related Asian and African Ancistrocladus species, were discovered for the first time in A. tectorius. The structure elucidation was achieved by spectroscopic analysis including HRESIMS, 1D and 2D NMR, and by chemical (oxidative degradation) and chiroptical (circular dichroism) methods. Chemotaxonomically remarkable, 5,8′-coupled naphthylisoquinolines have as yet been found quite rarely in AsianAncistrocladus species, where only two examples have so far been detected, while alkaloids with this coupling type represent the by far the largest group of constituents in African taxa. Ancistectorine D (5) shows promising activities against the protozoan parasites Trypanosoma cruzi and Leishmania donovani, and it was likewise found to display strong cytotoxic activities against human leukemia (CCRF-CEM) and multidrug-resistant tumor cells (CEM/ADR5000).
Instrument
J-715
Keywords
Circular dichroism, Absolute configuration, Pharmaceutical