Vismione H and structurally related anthranoid compounds of natural and synthetic origin as promising drugs against the human malaria parasite Plasmodium falciparum: Structure-activity relationships

Parasitology Research

Volumn 85, Issue 7, 1999, Pages 582-588

  François, Guido ^a,e   Steenackers, Tania ^a   Assi, Laurent Aké ^b   Steglich, Wolfgang ^c   Lamottke, Kai ^c   Holenz, Jörg ^d   Bringmann, Gerhard ^d  

^a INSTITUTE OF TROPICAL MEDICINE   (Belgium)

^b UNIVERSITÉ NANGUI ABROGOUA   (Côte d’Ivoire)

^c UNIVERSITY OF MUNICH   (Germany)

^d UNIVERSITY OF WÜRZBURG   (Germany)

^e UNIVERSITY OF ANTWERP   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

2,2'' BIRUFOOLIVACIN B; 3,4 DIHYDRO 3,3 DIMETHYL 6,8,9 TRIHYDROXYANTHRACEN 1(2H) ONE; 3,4 DIHYDRO 6,8 DIMETHOXY 3,3 DIMETHYL 9 HYDROXYANTHRACEN 1(2H) ONE; 3,4 DIHYDRO 6,8 DIMETHOXY 9 HYDROXY 3,3,7 TRIMETHYLANTHRACEN 1(2H) ONE; 3,4 DIHYDRO 8,9 DIHYDROXY 3,3 DIMETHYL 6 METHOXYANTHRACEN 1(2H) ONE; 4 HYDROXYFLAVOMANNIN 6,6' DI O METHYL ETHER A; ANHYDROPHLEGMACIN; ANHYDROPHLEGMACIN 9,10 QUINONE A2; ANTIMALARIAL AGENT; ATROCHRYSONE; DIMETHYLANTHRACEN 1(2H) ONE; FLAVOMANNIN 6,6' DI O METHYL ETHER A1; FLAVOMANNIN 6,6' DI O METHYL ETHER B1; PHLEGMACIN 8' O METHYL ETHER; PHLEGMACIN B1; RUFOOLIVACIN A; RUFOOLIVACIN B; TOROSACHRYSONE; TOROSCAHRYSONE 8 O METHYL ETHER; UNCLASSIFIED DRUG; VISMIONE H;

ANTIMALARIAL ACTIVITY; ARTICLE; CORTINARIUS; DRUG ACTIVITY; DRUG POTENCY; GROWTH INHIBITION; NONHUMAN; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

AGARICALES; ANIMALS; ANTHRACENES; ANTIMALARIALS; ERYTHROCYTES; HUMANS; PLANT EXTRACTS; PLASMODIUM FALCIPARUM; STRUCTURE-ACTIVITY RELATIONSHIP;

CORTINARIUS; FUNGI; PLASMODIUM FALCIPARUM; PROTOZOA; VISMIA; VISMIA GUINEENSIS;

EID: 0032967052     PISSN: 00443255     EISSN: None     Source Type: Journal    
DOI: 10.1007/s004360050598     Document Type: Article

References (38)

1. Abou-Shoer M, Suwanborirux K, Habib A-AM, Chang C-J, Cassady JM (1993) Xanthones and vismiones from Psorospermum febrifugum. Phytochemistry 34: 1413-1420
2. Adjanohoun E, Aké Assi L (1979) In. Ministère de la Recherche Scientifique, République de Côte d'Ivoire (ed) Contribution au recensement des plantes médicinales de Côte d'Ivoire. University of Abidjan, Abidjan, p 150
3. Billen G, Karl U, Scholl T, Stroech KD, Steglich W (1988) In: Atta-ur-Rahman, Le Quense PW (eds) Natural products chemistry III. Springer, Berlin Heidelberg New York, pp 305-315
4. Botta B, Delle Monache F, Delle Monache G, Marini-Bettolo GB, Oguakwa JU (1983) 3-Geranyloxy-6-methyl-1,8-dihydroxy-anthraquinone and vismiones C, D and E from Psorospermum febrifugum. Phytochemistry 22: 539-542
5. Botta B. Delle Monache F, Delle Monache G, Marini-Bettolo GB, Msonthi JD (1985) Prenylated bianthrones and vismione F from Psorospermum febrifugum. Phytochemistry 24: 827-830
6. Botta B, Delle Monache F, Delle Monache G, Kabangu K (1986a) Acetylvismione D from Psorospermum febrifugum. Phytochemistry 25: 766
7. Botta B, Delle Monache G, Delle Monache F, Marini-Bettolo GB, Menichini F (1986b) Vismione H and prenylated xanthones from Vismia guineënsis. Phytochemistry 25: 1217-1219
8. Cassinelli G, Geroni C, Botta B, Delle Monache G, Delle Monache F (1986) Cytotoxic and antitumor activity of vismiones isolated from Vismieae. J Nat Prod 49: 929-931
9. Chapuis J-C, Marston A, Sordat B, Hostettmann K (1986) Investigation of medicinal plants for their antiproliferative activities against a human tumour cell line. Planta Med: 553
10. Clark C, Key SW (1996) WHO releases revised facts on malaria. Malaria Weekly April 8, 15: 7-9
11. Delle Monache F, Botta B, Delle Monache G, Marini-Bettolo GB (1985) Prenylated anthranoids from Psorospermum species. Phytochemistry 24: 1855-1856
12. Desjardins RE, Canfield CJ, Haynes JD, Chulay JD (1979) Quantitative assessment of antimalarial activity in vitro by a semi-automated microdilution technique. Antimicrob Agents Chemother 16: 710-718
13. Diem K (1962) Probit transformation. Scientific tables, 6th ed. Documenta Geigy, Basel, pp 54-55
14. Dodd JH, Garigipati RS, Weinreb SM (1982) Development of a strategy for convergent total synthesis of the aureolic acid antitumor antibiotics. J Org Chem 47, 4045-4049
15. François G, Bringmann G, Phillipson JD, Aké Assi L, Dochez C, Rübenacker M, Schneider C, Wéry M, Warhurst DC, Kirby GC (1994a) Activity of extracts and naphthylisoquinoline alkaloids from Triphyophyllum peltatum, Ancistrocladus abbreviatus and A. barteri against Plasmodium falciparum in vitro. Phytochemistry 35: 1461-1464
16. François G, Hendrix L, Wéry M (1994b) A highly efficient in vitro cloning procedure for asexual erythrocytic forms of the human malaria parasite Plasmodium falciparum. Ann Soc Belge Med Trop 74: 177-192
17. François G, Timperman G, Holenz J, Aké Assi L, Geuder T, Macs L, Dubois J, Hanocq M, Bringmann G (1996) Naphthylisoquinoline alkaloids exhibit strong growth inhibiting activities against Plasmodium falciparum and P. berghei in vitro - Structure-activity relationship of dioncophylline C. Ann Trop Med Parasitol 90: 115-123
18. François G, Diakanamwa C, Timperman G, Bringmann G, Steenackers T, Atassi G, Van Looveren M, Holenz J, Tassin J-P, Aké Assi L, Vanhaelen-Fastré R, Vanhaelen M (1997) Antimalarial and cytotoxic potential of four quassinoids from Hannoa chlorantha and H. klaineana, and their structure-activity relationships. Int J Parasitol 28: 635-640
19. Fröde R (1994) Untersuchungen über Farbstoffe der Basidiomyceten Cortinarius rufoolivaceus und Russula flavida (Agaricales). Dissertation, LMU München
20. Gérault A (1982) Intoxication collective de type orellanien provoquée par Cortinarius splendens R. Hy. Bull Trim Soc Mycol Fr 97: 67-72
21. Gill M, Steglich W (1987) In: Herz W, Grisebach H, Kirby GW, Tamm C (eds) Progress in the Chemistry of Natural Products, vol. 51, Springer, Vienna New York, p 168
22. Gill M, Giménez A, Jhingran AG, Palfryman AR (1990) The first determination of central chirality in a coupled 3-hydroxy-3-methyl-3.4-dihydroanthracen-1(2H)-one. Aust J Chem 43: 1475-1478
23. Hamburger M, Marston A, Hostettmann K (1991) Search for new drugs of plant origin. Adv Drug Res 20: 167-215
24. Marston A, Chapuis JC, Sordat B, Msonthi JD, Hostettmann K (1986) Anthracenic derivatives from Psorospermum febrifugum and their in vitro cytotoxicities to a human colon carcinoma cell line. Planta Med 52: 207-210
25. Messanga BB, Tih RG, Kimbu SF, Sondengam BL, Martin MT, Bodo B (1992) Calodenone, a new isobiflavonoid from Ochna calodendron. J Nat Prod 55: 245-248
26. Nagem TJ, Alves VL (1995) Constituents of Vismia magnoliaefolia. Fitoterapia 66, 278
27. Nicoletti M, Marini-Bettolo GB, Delle Monache F, Delle Monache G (1982) Keto-enolic tautomerism and spectral data of prenylated anthranoids from Vismia genus. Tetrahedron 38: 3679-3686
28. Pasqua G, Monacelli B, Cuteri A, Spuntarelli F, Rascio N, Botta B, Delle Monache G, Scurria R, Delle Monache G (1995) Accumulation of vismione A in regenerated plants of Vismia guianensis DC. Protoplasma 189: 9-16
29. Rücker G (1995) Malariawirksame Verbindungen aus Pflanzen, insbesondere Peroxide. Pharm Unserer Zeit 24: 189-195
30. Sibanda S, Nyanyira C, Nicoletti M, Galeffi C (1993) Vismiones L and M from Ochna pulchra. Phytochemistry 34: 1650-1652
31. Simmonds MSJ, Blaney WM, Delle Monache F, Marquina MacQuhae M, Marini-Bettolo GB (1985) Insect antifeedant properties of anthranoids from the genus Vismia. J Chem Ecol 11: 1593-1599
32. Steglich W, Oertel B (1984) Untersuchung zur Konstitution und Verbreitung der Farbstoffe von Cortinarius, Untergattung Phlegmacium (Agaricales). Sydowia Ann Mycol 37: 284-295
33. Steglich W, Töpfer-Petersen E (1972) Phlegmacin und Anhydrophlegmacin, neuartige Farbstoffe aus dem Anisklumpfuss Cortinarius odorifer (Agaricales). Z Naturforsch 27B: 1286-1287
34. Steglich W, Töpfer-Petersen E (1973) Neue Pigmente vom Flavomannin-Typ aus Cortinarius vitellinus (Agaricales). Z Naturforsch 28C: 255-259
35. Steglich W, Töpfer-Petersen E, Reininger W, Gluchoff K, Arpin N (1972) Isolation of flavomannin-6,6′-dimethyl ether and one of its racemates from higher fungi. Phytochemistry 11: 3299-3304
36. Steglich W, Töpfer-Petersen E, Pils I (1973) Neue Phlegmacin-Derivate aus Cortinarius percomis (Agaricales). Z Naturforsch 28C: 354-355
37. Trager W, Jensen JB (1976) Human malaria parasites in continuous culture. Science 193: 673-675
38. Wright CW, Phillipson JD (1990) Natural products and the development of selective antiprotozoal drugs. Phytother Res 4: 127-139