title: Ancistrotanzanine C and related 5,1'- and 7,3'-coupled naphthylisoquinoline alkaloids from Ancistrocladus tanzaniensis.
abstract: Three new naphthylisoquinoline alkaloids, the 7,3'-coupled ancistrotanzanine C (6), the 5,1'-coupled O-methylancistrocladinine (7), and the likewise 5,1'-coupled O,N-dimethylancistrocladine (8, previously known only as a partial-synthetic compound), have been isolated from the highland liana Ancistrocladus tanzaniensis, along with the two known 7,3'-coupled naphthylisoquinoline alkaloids ancistrocladidine (4) and ancistrotectorine (5). All of the compounds are S-configured at C-3 and bear an oxygen at C-6, and thus belong to the so-called Ancistrocladaceae type, similar to 1-3 previously isolated from this newly discovered plant species. The structural elucidation was achieved by chemical, spectroscopic, and chiroptical methods. The biological activities of the alkaloids against the pathogens causing malaria tropica, leishmaniasis, Chagas' disease, and African sleeping sickness were evaluated.
authors.affiliation: Institut für Organische Chemie der Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany. bringmann@chemie.uni-wuerzburg.de
authors.forename: Gerhard
authors.initials: G
authors.lastname: Bringmann
authors.forename: Michael
authors.initials: M
authors.lastname: Dreyer
authors.forename: Johan H
authors.initials: JH
authors.lastname: Faber
authors.forename: Petur Weihe
authors.initials: PW
authors.lastname: Dalsgaard
authors.forename: Dan
authors.initials: D
authors.lastname: Staerk
authors.forename: Jerzy W
authors.initials: JW
authors.lastname: Jaroszewski
authors.forename: Henry
authors.initials: H
authors.lastname: Ndangalasi
authors.forename: Frank
authors.initials: F
authors.lastname: Mbago
authors.forename: Reto
authors.initials: R
authors.lastname: Brun
authors.forename: Søren Brøgger
authors.initials: SB
authors.lastname: Christensen
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007546:Isoquinolines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007893:Leishmania donovani / Q000187:drug effects; D019684:Magnoliopsida / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D010963:Plasmodium falciparum / Q000187:drug effects; D013636:Tanzania; D014344:Trypanocidal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D016833:Trypanosoma brucei rhodesiense / Q000187:drug effects; D014349:Trypanosoma cruzi / Q000187:drug effects
chemical_list: D000470:Alkaloids; D000962:Antimalarials; D007546:Isoquinolines; D014344:Trypanocidal Agents; C486998:ancistrotanzanine C