8-O-Methyldioncophyllinol B and revised structures of other 7,6'-coupled naphthylisoquinoline alkaloids from Triphyophyllum peltatum (Dioncophyllaceae)

Phytochemistry

Volumn 54, Issue 3, 2000, Pages 337-346

  Bringmann, Gerhard ^a   Günther, Christian ^a   Saeb, Wael ^a   Mies, Jan ^a   Brun, Reto ^b   Aké Assi, Laurent ^c  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE   (Switzerland)

^c UNIVERSITÉ NANGUI ABROGOUA   (Côte d’Ivoire)

Author keywords

1 epi Dioncophylline B; 8 O Methyl 1 epi dioncophylline B; 8 O Methyldioncophylline D; 8 O Methyldioncophyllinol B; Antimalarial activity; Dioncophyllaceae; Dioncophylline D; Dioncophyllinol B; Dioncophyllinol D; Naphthylisoquinoline alkaloids; Structural elucidation; Triphyophyllum peltatum

Indexed keywords

8 O METHYLDIONCOPHYLLINOL B; 8-O-METHYLDIONCOPHYLLINOL B; ALKALOID; ALKALOID DERIVATIVE; ANTIMALARIAL AGENT; ISOQUINOLINE DERIVATIVE; MEDICINAL PLANT; NAPHTHOL DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIMALARIAL ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; CONFORMATION; DRUG ISOLATION; DRUG OXIDATION; DRUG STRUCTURE; DRUG SYNTHESIS; MASS FRAGMENTOGRAPHY; NONHUMAN; PLANT LEAF; STRUCTURE ACTIVITY RELATION;

ALKALOIDS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; ISOQUINOLINES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NAPHTHOLS; PLANT LEAVES; PLANTS, MEDICINAL;

DIONCOPHYLLACEAE; TRIPHYOPHYLLUM PELTATUM;

EID: 0343069787     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(00)00107-2     Document Type: Article

References (23)

1. Bringmann G., Rübenacker M., Jansen J.R., Scheutzow D., Aké Assi, L. On the structure of the dioncophyllaceae alkaloids dioncophylline A ("triphyophylline") and "O-methyl-triphyophylline" Tetrahedron Lett. 31:1990;639-642.
2. Bringmann G., Rübenacker M., Geuder T., Aké Assi, L. Dioncophylline B, a naphthylisoquinoline alkaloid with a new coupling type from Triphyophyllum peltatum. Phytochemistry. 30:1991;3845-3847.
3. Bringmann G., Geuder T., Rübenacker M., Zagst R. A facile degradation procedure for determination of absolute configuration in 1,3-dimethyltetra- and dihydroisoquinolines. Phytochemistry. 30:1991;2067-2070.
4. Bringmann G., Ortmann T., Rübenacker M., Aké Assi, L. Dioncophyllacine B: a new 4-methoxylated naphthylisoquinoline alkaloid from the leaves of Triphyophyllum peltatum. Planta Med. 58:(Suppl. 1):1992;701-702.
5. Bringmann G., Pokorny F. The naphthylisoquinoline alkaloids. Cordell G.A. The Alkaloids. vol. 46:1995;127-271 Academic Press, New York.
6. Bringmann G., God R., Schäffer M. An improved degradation procedure for determination of the absolute configuration in chiral isoquinoline and β-carboline derivatives. Phytochemistry. 43:1996;1393-1403.
7. Bringmann G., Koppler D., Wiesen B., François G., Sankara Narayanan, A.S., Almeida M.R, Schneider H., Zimmermann U. Ancistroheynine A, the first 7,8′-coupled naphthylisoquinoline alkaloid from Ancistrocladus heyneanus. Phytochemistry. 43:1996;1405-1410.
8. Bringmann, G., Götz, R., Harmsen, S., Holenz J., Walter, R. (1996c). Biomimetic total synthesis of michellamines A-C. Liebigs Ann. 2045-2048.
9. Bringmann G., Günther C., Busemann S., Schäffer M., Olowokudejo J.D., Alo B. Ancistroguineines A and B as well as ancistrotectorine - naphthylisoquinoline alkaloids from Ancistrocladus guineënsis. Phytochemistry. 47:1998;37-43.
10. Bringmann G., François G., Aké Assi L., Schlauer J. The alkaloids of Triphyophyllum peltatum (Dioncophyllaceae). Chimia. 52:1998;18-28.
11. Bringmann G., Wenzel M., Rübenacker M., Schäffer M., Rückert M., Aké Assi, L. Dioncophylline D and 8-O-methyldioncophylline D, 7,8′-coupled naphthylisoquinoline alkaloids from Triphyophyllum peltatum. Phytochemistry. 49:1998;1151-1155.
12. Bringmann G., Wenzel M., Rückert M., Wolf K., Busemann S., Schäffer M., Aké Assi, L. Dioncophyllinol D, the first 4-hydroxylated naphthylisoquinoline alkaloid from the leaves of Triphyophyllum peltatum. Heterocycles. 47:1998;985-990.
13. Bringmann, G., Günther, C., 1999. First total synthesis of dioncophylline B, a 7,6′-coupled naphthylisoquinoline alkaloid. Synlett, 216-218.
14. Bringmann G., Ochse M., Michel M. Gentrymine B, an N-quaternary Ancistrocladus alkaloid: stereoanalysis, synthesis, and biomimetic formation from gentrymine A. Tetrahedron. 56:2000;581-585.
15. Bringmann G., Feineis D. Novel antiparasitic biaryl alkaloids from West african Dioncophyllaceae plants. Act. Chim. Thérapeut. 26:2000;151-172.
16. Desjardins R.E., Canfield C.J., Haynes D., Chulay J. Quantitative assessment of antimalarial activity in vitro by a semiautomated microdilution assay. Antimicrob. Agents Chemother. 16:1979;710-718.
17. François G., Bringmann G., Phillipson J.D., Aké Assi, L., Dochez C., Rübenacker M., Schneider C., Wéry M., Warhurst D.C., Kirby G.C. Activity of Extracts and Naphthylisoquinoline Alkaloids from Triphyophyllum peltatum, Ancistrocladus abbreviatus and A. barteri against Plasmodium falciparum in vitro. Phytochemistry. 35:1994;1461-1464.
18. Govindachari T.R., Nagarajan K., Parthasarathy P.C., Rajagopalan T.G., Desai H.K., Kartha G., Chen S.-M.L., Nakanishi K. Absolute stereochemistry of ancistrocladine and ancistrocladinine. J. Chem. Soc. Perkin Trans. 1:1974;1413-1417.
19. Hallock Y.F., Cardellina II, J.H., Schäffer M., Stahl M., Bringmann G., François G., Boyd M.R. Yaoundamines A and B, new antimalarial naphthylisoquinoline alkaloids from Ancistrocladus korupensis. Tetrahedron. 53:1997;8121-8128.
20. Hesse M., Meier H., Zeeh M. Spektroskopische Methoden in der organischen Chemie. 4th ed. 1991;Stuttgart, New York: Thieme.
21. Pagé B., Pagé M., Noel C. A new fluorometric assay for cytotoxicity measurements in vitro. Int. J. Oncol. 3:1993;473-476.
22. Räz B., Iten M., Grether-Bühler Y., Kaminsky R., Brun R. The Alamar Blue assay to determine drug sensitivity of African trypanosomes (T. b. rhodesiense and T. b. gambiense) in vitro. Acta Trop. 68:1997;139-147.
23. Ridley R.G., Hofheinz W., Matile H., Jacquet C., Dorn A., Masciadri R., Jolidon S., Richter W.F., Guenzi A., Girometta M.A., Urwyler H., Huber W., Thaitong S., Peters W. 4-Aminoquinoline analogs of chloroquine with shortened side chains retain activity against chloroquine-resistant Plasmodium falciparum. Antimicrob. Agents Chemother. 40:1996;1846-1854.