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Phenolic analogs of the N,C-coupled naphthylisoquinoline alkaloid ancistrocladinium A, from Ancistrocladus cochinchinensis (Ancistrocladaceae), with improved antiprotozoal activities |
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| Authors: | Bringmann Gerhard Hertlein-Amslinger Barbara Kajahn Inga Dreyer Michael Brun Reto Moll Heidrun Stich August Ioset Karine Ndjoko Schmitz Werner Ngoc Luu Hoang |
| Affiliation: | a Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany b Swiss Tropical and Public Health Institute, Socinstr. 57, CH-4002 Basel, Switzerland c University of Basel, CH-4003 Basel, Switzerland d Institute for Molecular Infection Biology, University of Würzburg, Josef-Schneider-Str. 2/D15, D-97080 Würzburg, Germany e Medical Mission Institute Würzburg, Department of Tropical Medicine, Salvatorstr. 7, D-97074 Würzburg, Germany f Laboratoire de Pharmacognosie et Phytochimie, Section des Sciences Pharmaceutiques, Université de Genève, Quai Ernest Ansermet 30, CH-1211 Genève 4, Switzerland g Institute of Physiological Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany h Vietnam Institute for Industrial Chemistry, 2 Pham Ngu Lao Hanoi, Viet Nam |
| Abstract: | The first N,8′-coupled naphthylisoquinoline alkaloids with free phenolic OH groups, 4′-O-demethylancistrocladinium A and 6,4′-O-didemethylancistrocladinium A, have been isolated from the leaves and bark of the Vietnamese liana Ancistrocladus cochinchinensis, along with its known, non-phenolic parent compound, ancistrocladinium A, and four C,C-coupled representatives. The structure elucidation was achieved by chemical, spectroscopic, and chiroptical methods. The mono-phenolic alkaloid showed excellent activities in particular against the pathogen causing Chagas’ disease, Trypanosoma cruzi. |
| Keywords: | Ancistrocladus cochinchinensis Ancistrocladaceae Naphthylisoquinoline alkaloids Chiral N,C-axes 4&prime -O-Demethylancistrocladinium A 6,4&prime -O-Didemethylancistrocladinium A Anti-parasitic activity |
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