Phenolic analogs of the N,C-coupled naphthylisoquinoline alkaloid ancistrocladinium A, from Ancistrocladus cochinchinensis (Ancistrocladaceae), with improved antiprotozoal activities.
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.
Institute of Organic Chemistry, University of Würzburg, Würzburg, Germany. bringman@chemie.uni-wuerzburg.de
Gerhard
G
Bringmann
Barbara
B
Hertlein-Amslinger
Inga
I
Kajahn
Michael
M
Dreyer
Reto
R
Brun
Heidrun
H
Moll
August
A
Stich
Karine Ndjoko
KN
Ioset
Werner
W
Schmitz
Luu Hoang
LH
Ngoc
D000470:Alkaloids / Q000737:chemistry; D000981:Antiprotozoal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007546:Isoquinolines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D024301:Plant Bark / Q000737:chemistry; D018515:Plant Leaves / Q000737:chemistry; D014349:Trypanosoma cruzi / Q000187:drug effects*; D014744:Vietnam
C555900:4'-O-demethylancistrocladinium A; C555901:6,4'-O-didemethylancistrocladinium A; D000470:Alkaloids; D000981:Antiprotozoal Agents; D007546:Isoquinolines; C522869:ancistrocladinium A