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.
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 Asian Ancistrocladus 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).
authors.affiliation: Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany. Electronic address: bringman@chemie.uni-wuerzburg.de.
authors.forename: Gerhard
authors.initials: G
authors.lastname: Bringmann
authors.affiliation: Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany.
authors.forename: Raina
authors.initials: R
authors.lastname: Seupel
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: Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany.
authors.forename: Guoliang
authors.initials: G
authors.lastname: Zhang
authors.affiliation: Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany; Key Laboratory of Systems Biomedicine, Shanghai Center for Systems Biomedicine, Shanghai Jia Tong University, 800 Dongchuan Road, Shanghai 200240, PR China.
authors.forename: Minjuan
authors.initials: M
authors.lastname: Xu
authors.affiliation: Marine Drugs Research Center, College of Pharmacy, Jinan University, 601 Huangpu Avenue West, Guangzhou 510632, PR China.
authors.forename: Jun
authors.initials: J
authors.lastname: Wu
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: Marcel
authors.initials: M
authors.lastname: Kaiser
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 Pharmacy and Biochemistry, Department of Pharmaceutical Biology, University of Mainz, Staudinger Weg 5, D-55128 Mainz, Germany.
authors.forename: Ean-Jeong
authors.initials: EJ
authors.lastname: Seo
authors.affiliation: Institute of Pharmacy and Biochemistry, Department of Pharmaceutical Biology, University of Mainz, Staudinger Weg 5, D-55128 Mainz, Germany.
authors.forename: Thomas
authors.initials: T
authors.lastname: Efferth
mesh_terms: D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000302:isolation & purification; D000981:Antiprotozoal Agents / Q000737:chemistry* / Q000302:isolation & purification; D045744:Cell Line, Tumor; D018432:Drug Resistance, Multiple; D019008:Drug Resistance, Neoplasm; D006801:Humans; D007546:Isoquinolines / Q000737:chemistry* / Q000302:isolation & purification; D007893:Leishmania donovani / Q000187:drug effects; D019684:Magnoliopsida / Q000737:chemistry*; D015394:Molecular Structure; D009284:Naphthols / Q000737:chemistry* / Q000302:isolation & purification; D018547:Plant Stems / Q000737:chemistry; D014349:Trypanosoma cruzi / Q000187:drug effects
chemical_list: D000470:Alkaloids; D000972:Antineoplastic Agents, Phytogenic; D000981:Antiprotozoal Agents; D007546:Isoquinolines; D009284:Naphthols; C000613743:ancistectorine D
keywords: Ancistectorine D; Ancistrocladaceae; Ancistrocladus tectorius; Antileukemic agents; Antiprotozoal agents; Naphthylisoquinoline alkaloids