Ancistrolikokine D, a 5.8′-coupled naphthylisoquinoline alkaloid and related natural products from Ancistrocladus likoko

被引:34
作者
Bringmann, G [1 ]
Saeb, W
Rückert, M
Mies, J
Michel, M
Mudogo, V
Brun, R
机构
[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
[2] Univ Kinshasa, Fac Sci, Kinshasa, DEM REP CONGO
[3] Swiss Trop Inst, CH-4002 Basel, Switzerland
关键词
Ancistroclacdus likoko; Ancistrocladaceae; structural elucidation; naphthylisoquinoline alkaloids; Ancistrolikokine D; ancistroealaine A; ancistronaphthoic acid B; isoshinanolone; antiprotozoal activity;
D O I
10.1016/S0031-9422(02)00570-8
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A new naphthylisoquinoline alkaloid, ancistrolikokine D, and the likewise 5,8'-coupled alkaloid ancistroealaine A, as well as two further, biosynthetically related, but nitrogen-free natural products, ancistronaphthoic acid B and cis-isoshinanolone, have been isolated from Ancistrocladus likoko J. LEONARD (Ancistrocladaceae). The 5,8'-coupling of the new alkaloids and of the alkaloids isolated earlier hints at a close phylogenetic relationship of A. likoko to other Central African Ancistrocladus species. The compounds show moderate activities against Leishmania donovani, Trypanosoma cruzi., and Trypanosoma brucei rhodesiense. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:631 / 636
页数:6
相关论文
共 24 条
[1]   ANTI-HIV MICHELLAMINES FROM ANCISTROCLADUS-KORUPENSIS [J].
BOYD, MR ;
HALLOCK, YF ;
MANFREDI, KP ;
BLUNT, JW ;
MCMAHON, JB ;
BUCKHEIT, RW ;
BRINGMANN, G ;
SCHAFFER, M ;
CRAGG, GM ;
THOMAS, DW ;
JATO, JG ;
CARDELLINA, JH .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (12) :1740-1745
[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]   Acetogenic isoquinoline alkaloids.: Part 151.: Habropetaline A, an antimalarial naphthylisoquinoline alkaloid from Triphyophyllum peltatum [J].
Bringmann, G ;
Messer, K ;
Schwöbel, B ;
Brun, R ;
Assi, LA .
PHYTOCHEMISTRY, 2003, 62 (03) :345-349
[4]   Stress-related polyketide metabolism of dioncophyllaceae and ancistrocladaceae [J].
Bringmann, G ;
Feineis, D .
JOURNAL OF EXPERIMENTAL BOTANY, 2001, 52 (363) :2015-2022
[5]  
Bringmann G, 2000, ANGEW CHEM INT EDIT, V39, P1464, DOI 10.1002/(SICI)1521-3773(20000417)39:8<1464::AID-ANIE1464>3.0.CO
[6]  
2-#
[7]   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
[8]   ACETOGENIC ISOQUINOLINE ALKALOIDS .34. ANCISTROBREVINE-B, THE 1ST NAPHTHYLISOQUINOLINE ALKALOID WITH A 5,8'-COUPLING SITE, AND RELATED-COMPOUNDS FROM ANCISTROCLADUS-ABBREVIATUS [J].
BRINGMANN, G ;
ZAGST, R ;
REUSCHER, H ;
ASSI, LA .
PHYTOCHEMISTRY, 1992, 31 (11) :4011-4014
[9]  
Bringmann G, 1999, MAGN RESON CHEM, V37, P98, DOI 10.1002/(SICI)1097-458X(199902)37:2<98::AID-MRC428>3.0.CO
[10]  
2-I