Acetogenic isoquinoline alkaloids.: Part 151.: Habropetaline A, an antimalarial naphthylisoquinoline alkaloid from Triphyophyllum peltatum

被引:26
作者
Bringmann, G
Messer, K
Schwöbel, B
Brun, R
Assi, LA
机构
[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
[2] Ctr Natl Florist, Abidjan 08, Cote Ivoire
[3] Schweizer Tropeninst, CH-4002 Basel, Switzerland
关键词
Triphyophyllum peltatum; Dioncophyllaceae; habropetaline A; structural elucidation; stereochemistry; antimalarial activity;
D O I
10.1016/S0031-9422(02)00547-2
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 [生物化学与分子生物学]; 081704 [应用化学];
摘要
The isolation, structural elucidation, and antiprotozoal activities of habropetaline A, a novel naphthylisoquinoline alkaloid from Triphyophyllum peltatum, are-described. This alkaloid had previously only been identified on line, by the LC-MS/MS-NMR-CD triad, in the crude extract of the rare and difficult-to-provide related plant species Habropetalum dawei, whose small quantities available had not permitted to isolate the compound. As predicted by quantitative structure activity relationship (QSAR) investigations, habropetaline A exhibits strong antimalarial activity against Plasmodium falciparum, while it is inactive against other protozoal pathogens (Trypanosoma brucei rhodesience, T. cruzi, and Leishmania donovani). (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:345 / 349
页数:5
相关论文
共 28 条
[1]
HPLC-CD on-line coupling in combination with HPLC-NMR and HPLC-MS/MS for the determination of the full absolute stereostructure of new metabolites in plant extracts [J].
Bringmann, G ;
Messer, K ;
Wohlfarth, M ;
Kraus, J ;
Dumbuya, K ;
Rückert, M .
ANALYTICAL CHEMISTRY, 1999, 71 (14) :2678-2686
[2]
Acetogenic isoquinoline alkaloids.: Part 127 -: Cis- and trans-isoshinanolone from Dioncophyllum thollonii:: absolute configuration of two 'known', wide-spread natural products [J].
Bringmann, G ;
Münchbach, M ;
Messer, K ;
Koppler, D ;
Michel, M ;
Schupp, O ;
Wenzel, M ;
Louis, AM .
PHYTOCHEMISTRY, 1999, 51 (05) :693-699
[3]
Dioncophylline E from Dioncophyllum thollonii, the first 7,3′-coupled dioncophyllaceous naphthylisoquinoline alkaloid [J].
Bringmann, G ;
Messer, K ;
Wolf, K ;
Mühlbacher, J ;
Grüne, M ;
Brun, R ;
Louis, AM .
PHYTOCHEMISTRY, 2002, 60 (04) :389-397
[4]
Bringmann G, 1997, MAGN RESON CHEM, V35, P297, DOI 10.1002/(SICI)1097-458X(199705)35:5<297::AID-OMR88>3.0.CO
[5]
2-J
[6]
In vitro propagation of the alkaloid-producing rare African liana, Triphyophyllum peltatum (Dioncophyllaceae) [J].
Bringmann G. ;
Rischer H. .
Plant Cell Reports, 2001, 20 (07) :591-595
[7]
Bringmann G, 2000, ANGEW CHEM INT EDIT, V39, P1464, DOI 10.1002/(SICI)1521-3773(20000417)39:8<1464::AID-ANIE1464>3.0.CO
[8]
2-#
[9]
Ancistroealaines A and B, two new bioactive naphthylisoquinolines, and related naphthoic acids from Ancistrocladus ealaensis [J].
Bringmann, G ;
Hamm, A ;
Günther, C ;
Michel, M ;
Brun, R ;
Mudogo, V .
JOURNAL OF NATURAL PRODUCTS, 2000, 63 (11) :1465-1470
[10]
ACETOGENIC ISOQUINOLINE ALKALOIDS .24. DIONCOPELTINE-A AND DIONCOLACTONE-A - ALKALOIDS FROM TRIPHYOPHYLLUM-PELTATUM [J].
BRINGMANN, G ;
RUBENACKER, M ;
VOGT, P ;
BUSSE, H ;
ASSI, LA ;
PETERS, K ;
VONSCHNERING, HG .
PHYTOCHEMISTRY, 1991, 30 (05) :1691-1696