Mbandakamines A and B, Unsymmetrically Coupled Dimeric Naphthylisoquinoline Alkaloids, from a Congolese Ancistrocladus Species

被引:51
作者
Bringmann, Gerhard [1 ]
Lombe, Blaise Kimbadi [1 ,2 ]
Steinert, Claudia [1 ]
Ioset, Karine Ndjoko [1 ]
Brun, Reto [3 ,4 ]
Turini, Florian [5 ]
Heubl, Guenther [5 ]
Mudogo, Virima [2 ]
机构
[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
[2] Univ Kinshasa, Fac Sci, Kinshasa 11, DEM REP CONGO
[3] Swiss Trop & Publ Hlth Inst, CH-4002 Basel, Switzerland
[4] Univ Basel, CH-4003 Basel, Switzerland
[5] Univ Munich, Dept Biol 1, Sect Systemat Bot, D-80638 Munich, Germany
关键词
ACETOGENIC ISOQUINOLINE ALKALOIDS; MICHELLAMINES; KORUPENSAMINE; AXES;
D O I
10.1021/ol4005883
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Mbandakamines A (1) and B (2), isolated from the leaves of an as yet unidentified Congolese Ancistrocladus species, are the first dimeric naphthylisoquinoline alkaloids with an unsymmetrically coupled central biaryl axis. Their novel 6',1 ''-coupling type implies a hitherto unprecedented pen pen coupling in one of the naphthalene parts, leading to the as yet highest steric hindrance at the central axis and a total of seven elements of chirality. Mbandakamine A exhibits good antimalarial activity.
引用
收藏
页码:2590 / 2593
页数:4
相关论文
共 22 条
  • [1] ANTI-HIV MICHELLAMINES FROM ANCISTROCLADUS-KORUPENSIS
    BOYD, MR
    HALLOCK, YF
    MANFREDI, KP
    BLUNT, JW
    MCMAHON, JB
    BUCKHEIT, RW
    BRINGMANN, G
    SCHAFFER, M
    CRAGG, GM
    THOMAS, DW
    JATO, JG
    CARDELLINA, JH
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (12) : 1740 - 1745
  • [2] Jozimine B, a constitutionally unsymmetric, antiplasmodial 'dimer' of the naphthylisoquinoline alkaloid ancistrocladine
    Bringmann, G
    Saeb, W
    Kraus, J
    Brun, R
    François, G
    [J]. TETRAHEDRON, 2000, 56 (22) : 3523 - 3531
  • [3] A photometric screening method for dimeric naphthylisoquinoline alkaloids and complete on-line structural elucidation of a dimer in crude plant extracts, by the LC-MS/LC-NMR/LC-CD triad
    Bringmann, G
    Wohlfarth, M
    Rischer, H
    Heubes, M
    Saeb, W
    Diem, S
    Herderich, M
    Schlauer, J
    [J]. ANALYTICAL CHEMISTRY, 2001, 73 (11) : 2571 - 2577
  • [4] Bringmann G, 2000, ANGEW CHEM INT EDIT, V39, P1464, DOI 10.1002/(SICI)1521-3773(20000417)39:8<1464::AID-ANIE1464>3.0.CO
  • [5] 2-#
  • [6] Acetogenic isoquinoline alkaloids part 136 -: 8-O-methyldioncophyllinol B and revised structures of other 7,6′-coupled naphthylisoquinoline alkaloids from Triphyophyllum peltatum (Dioncophyllaceae)
    Bringmann, G
    Günther, C
    Saeb, W
    Mies, J
    Brun, R
    Assi, LA
    [J]. PHYTOCHEMISTRY, 2000, 54 (03) : 337 - 346
  • [7] A convergent total synthesis of the michellamines
    Bringmann, G
    Götz, R
    Keller, PA
    Walter, R
    Boyd, MR
    Lang, FR
    Garcia, A
    Walsh, JJ
    Tellitu, I
    Bhaskar, KV
    Kelly, TR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) : 1090 - 1097
  • [8] ACETOGENIC ISOQUINOLINE ALKALOIDS .69. BIOMIMETIC OXIDATIVE DIMERIZATION OF KORUPENSAMINE A - COMPLETION OF THE FIRST TOTAL SYNTHESIS OF MICHELLAMINE-A, MICHELLAMINE-B, AND MICHELLAMINE-C
    BRINGMANN, G
    HARMSEN, S
    HOLENZ, J
    GEUDER, T
    GOTZ, R
    KELLER, PA
    WALTER, R
    HALLOCK, YF
    CARDELLINA, JH
    BOYD, MR
    [J]. TETRAHEDRON, 1994, 50 (32) : 9643 - 9648
  • [9] Bringmann G, 1998, CHIMIA, V52, P18
  • [10] An improved degradation procedure for determination of the absolute configuration in chiral isoquinoline and beta-carboline derivatives
    Bringmann, G
    God, R
    Schaffer, M
    [J]. PHYTOCHEMISTRY, 1996, 43 (06) : 1393 - 1403