title: Cyclombandakamines A1and A2, Oxygen-Bridged Naphthylisoquinoline Dimers from a Congolese Ancistrocladus Liana.
abstract: Cyclombandakamines A1(1) and A2(2), both with an unprecedented pyrane-cyclohexenone-dihydrofuran sequence and six stereocenters and two chiral axes, are the first oxygen-bridged dimeric naphthylisoquinoline alkaloids. They were isolated from the leaves of an as yet unidentified Congolese Ancistrocladus species. Their stereostructures were established by spectroscopic, chemical, and chiroptical methods in combination with DFT and TDDFT calculations. They apparently originate from a cascade of oxidative cyclization reactions of "open-chain" naphthylisoquinoline dimers and exhibit significant antiprotozoal activities.
authors.affiliation: Institute of Organic Chemistry, University of Würzburg , Am Hubland, D-97074 Würzburg, Germany.|Faculté des Sciences, Université de Kinshasa , B.P. 202 Kinshasa XI, Democratic Republic of the Congo.
authors.forename: Blaise Kimbadi
authors.initials: BK
authors.lastname: Lombe
authors.affiliation: Institute of Organic Chemistry, University of Würzburg , Am Hubland, D-97074 Würzburg, Germany.|Federal Institute for Risk Assessment , Max-Dohrn-Straße 8-10, D-10589 Berlin, Germany.
authors.forename: Torsten
authors.initials: T
authors.lastname: Bruhn
authors.affiliation: Institute of Organic Chemistry, University of Würzburg , Am Hubland, D-97074 Würzburg, Germany.
authors.forename: Doris
authors.initials: D
authors.lastname: Feineis
authors.affiliation: Faculté des Sciences, Université de Kinshasa , B.P. 202 Kinshasa XI, Democratic Republic of the Congo.
authors.forename: Virima
authors.initials: V
authors.lastname: Mudogo
authors.affiliation: Swiss Tropical and Public Health Institute , Socinstrasse 57, CH-4002 Basel, Switzerland.|University of Basel , Petersplatz 1, CH-4003 Basel, Switzerland.
authors.forename: Reto
authors.initials: R
authors.lastname: Brun
authors.affiliation: Institute of Organic Chemistry, University of Würzburg , Am Hubland, D-97074 Würzburg, Germany.
authors.forename: Gerhard
authors.identifier: 0000-0002-3583-5935
authors.initials: G
authors.lastname: Bringmann
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000981:Antiprotozoal Agents / Q000737:chemistry* / Q000494:pharmacology; D003223:Congo; D003500:Cyclization; D019281:Dimerization; D006801:Humans; D007546:Isoquinolines / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D008958:Models, Molecular; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry* / Q000302:isolation & purification; D018515:Plant Leaves / Q000737:chemistry; D010963:Plasmodium falciparum / Q000187:drug effects; D013237:Stereoisomerism; D057949:Streptophyta / Q000737:chemistry*; D013329:Structure-Activity Relationship; D016833:Trypanosoma brucei rhodesiense / Q000187:drug effects; D014353:Trypanosomiasis, African / Q000188:drug therapy
chemical_list: D000470:Alkaloids; D000981:Antiprotozoal Agents; D007546:Isoquinolines; D009281:Naphthalenes; D010936:Plant Extracts; D010100:Oxygen