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

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 11期

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

页码：2590 / 2593

页数：4

共 22 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] Jozimine B, a constitutionally unsymmetric, antiplasmodial 'dimer' of the naphthylisoquinoline alkaloid ancistrocladine [J].

Bringmann, G ;

Saeb, W ;

Kraus, J ;

Brun, R ;

François, G .

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 [J].

Bringmann, G ;

Wohlfarth, M ;

Rischer, H ;

Heubes, M ;

Saeb, W ;

Diem, S ;

Herderich, M ;

Schlauer, 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) [J].

Bringmann, G ;

Günther, C ;

Saeb, W ;

Mies, J ;

Brun, R ;

Assi, LA .

PHYTOCHEMISTRY, 2000, 54 (03) :337-346

[7] A convergent total synthesis of the michellamines [J].

Bringmann, G ;

Götz, R ;

Keller, PA ;

Walter, R ;

Boyd, MR ;

Lang, FR ;

Garcia, A ;

Walsh, JJ ;

Tellitu, I ;

Bhaskar, KV ;

Kelly, TR .

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 [J].

BRINGMANN, G ;

HARMSEN, S ;

HOLENZ, J ;

GEUDER, T ;

GOTZ, R ;

KELLER, PA ;

WALTER, R ;

HALLOCK, YF ;

CARDELLINA, JH ;

BOYD, MR .

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 [J].

Bringmann, G ;

God, R ;

Schaffer, M .

PHYTOCHEMISTRY, 1996, 43 (06) :1393-1403

← 1 2 3 →