Antimalarial quassinoids: Past, present and future

Expert Opinion on Drug Discovery

Volumn 2, Issue 8, 2007, Pages 1065-1084

  Muhammad, Ilias ^a   Samoylenko, Volodymyr ^a  

^a UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

Antimalarial activity; Chemistry; Plasmodium berghei; Plasmodium falciparum; Plasmodium vinkei; Plasmodium yoelii yoelii; Quassinoids; SAR; Simaroubaceae

Indexed keywords

14 HYDROXYCHAPARRINONE; AILANTHONE; AMODIAQUINE; ANTIMALARIAL AGENT; ARTEETHER; ARTEMETHER; ARTEMISININ; ARTESUNATE; BRUCEINE A; BRUCEINE B; BRUCEINE D; BRUCEOLIDE; BRUSATOL; CEDRONIN; CHAPARRINE; CHAPARRINONE; CHLOROQUINE; CINCHONA EXTRACT; EURYCOMANONE; GLAUCARUBINONE; MEFLOQUINE; ORINOCENOLIDE; PASAKBUMIN B; PLANT EXTRACT; PRIMAQUINE; QUASSINOID DERIVATIVE; QUININE; SIMABA CEDRON EXTRACT; SIMALIKALACTONE D; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIMALARIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; BRAIN MALARIA; DRUG ISOLATION; DRUG MEGADOSE; DRUG POTENCY; DRUG TOLERABILITY; FEVER; HUMAN; IC 50; IN VITRO STUDY; KIDNEY DISEASE; MALARIA; MEDICINAL PLANT; NONHUMAN; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL; PROTEIN SYNTHESIS INHIBITION; REVIEW; SIMABA CEDRON; SIMAROUBACEAE; SINGLE DRUG DOSE; STRUCTURE ACTIVITY RELATION;

EID: 34548425093     PISSN: 17460441     EISSN: None     Source Type: Journal    
DOI: 10.1517/17460441.2.8.1065     Document Type: Review

References (66)

1. GOODSON JA, HENRY TA: Composition of cinchona febrifuge. Quart. J. Pharm. Pharmacol. (1930) 3:238-248.
2. ZIFFER H, HIGHET RJ, KLAYMAN DL: Artemisinin: an endoperoxidic antimalarial from Artemisia annua L. Prog. Chem. Org. Nat. Prod. (1997) 72:121-214.
3. HAYNES RK: From artemisinin to new artemisinin antimalarials: biosynthesis, extraction, old and new derivatives, stereochemistry and medicinal chemistry requirements. Curr. Top. Med. Chem. (2006) 6(5):509-537.
4. NOUCK E, PICADO T: Cedrin in malaria. Rev. Sudamericana Endocrinol. Inmunol. Quimioterap. (1930) 13:609-610.
5. POLONSKY J: Study of constituents of Simaba cedron seeds; structure of two crystalline compounds: cedronin and cedronylin. Bull. Soc. Chim. Fr. (1960):1845-1847.
6. OKANO M, FUKAMIYA N, LEE KH: Biologically active compounds from simaroubaceous plants. In: Studies in Natural Products Chemistry (Volume 7). Structure & Chemistry, Part A. Atta-ur-Rahman (Ed.), Elsevier Science Publisher, Amsterdam (1990):369-404.
7. GOLDSMITH R, HEYNEMANN D (Eds): Tropical Medicine and Parasitology. Appleton & Lange, Norwalk, CT (1989):942.
8. MTURI N, MUSUMBA CO, WAMOLA BM, OGUTU BR, NEWTON CRJC: Cerebral malaria: Optimizing management. CNS Drugs (2003) 17(3):153-165.
9. JOHN CC, IDRO RI: Cerebral malaria in Children. Infect. Med. (2003) 20(1):53-58.
10. MAKLER MT, RIES JM, WILLIAMS JA et al.: Parasite lactate dehydrogenase as an assay for Plasmodium falciparum drug sensitivity. Am. J. Trop. Med. Hyg. (1993) 48(6):739-741.
11. VAN DER HEYDE HC, ELLOSO MM, VANDE WJ, SCHELL K, WEIDANZ WP: Use of hydroethidine and flow cytometry to assess the effects of leukocytes on the malarial parasite Plasmodium falciparum. Clin. Diagn. Lab. Immunol. (1995) 2(4):417-425.
12. SMILKSTEIN M, SRIWILAIJAROEN N, KELLY JX, WILAIRAT P, RISCOE M: Simple and inexpensive fluorescence-based technique for high-throughput antimalarial drug screening. Antimicrob. Agents Chemother. (2004) 48(5): 1803-1806.
13. O'NEILL MJ, BRAY DH, BOARDMAN P et al.: Plants as sources of antimalarial drugs. Part 4: Activity of Brucea javanica fruits against chloroquine-resistant Plasmodium falciparum in vitro and against Plasmodium berghei in vivo. J. Nat. Prod. (1987) 50(1):41-48.
14. KIM HS, SHIBATA Y, KO N et al.: Potent in vivo antimalarial activity of 3, 15-di-O-acetylbruceolide against Plasmodium berghei infection in mice. Parasitol. Int. (2000) 48(3):271-274.
15. MORETTI C, DEHARO E, SAUVAIN M et al.: Antimalarial activity of cedronin. J. Ethnopharmacol. (1994) 43(1):57-61.
16. BERTANI S, HOUEL E, STIEN D et al.: Simalikalactone D is responsible for the antimalarial properties of an amazonian traditional remedy made with Quassia amara L. (Simaroubaceae). J. Ethnopharmacol. (2006) 108(1):155-157.
17. KUPCHAN SM, BRITTON RW, LACADIE JA, ZIEGLER MF, SIGEL CW: The isolation and structural elucidation of bruceantin and bruceantinol, new potent antileukemic quassinoids from Brucea antidysenterica. J. Org. Chem. (1975) 40(5):648-654.
18. CANIATO R, PURICELLI L: Review: natural antimalarial agents (1995 - 2001). Crit. Rev. Plant Sci. (2003) 22(1):79-105.
19. TANG W, EISENBRAND G (Eds): Chinese Drugs of Plant Origin: Chemistry, Pharmacology and Use in Traditional and Modern Medicine. Springer-Verlag, Berlin, New York (1992).
20. CABRAL JA, MCCHESNEY JD, MILHOUS WK: A new antimalarial quassinoid from Simaba guianensis. J. Nat. Prod. (1993) 56(11):1954-1961.
21. CALZADO FLORES CC, SEGURA JJ, RODRIGUEZ VM, DOMINGUEZ XA: A new amebicide agent from Castela texana. Proc. West Pharmacol. Soc. (1983) 26:431-434.
22. SIMAO SM, BARREIROS EL, DA SILVA MFD, GOTTLIEB OR: Plant chemosystematics and phylogeny. Part 33. Chemogeographical evolution of quassinoids in Simaroubaceae. Phytochemistry (1991) 30(3):853-865.
23. CLARK EP: Quassin. I. The preparation and purification of quassin and neoquassin, with information concerning their molecular formulas. J. Am. Chem. Soc. (1937) 59:927-931.
24. CLARK EP: Quassin. II. Neoquassin. J. Am. Chem. Soc. (1937) 59:2511-2514.
25. VALENTA Z, GRAY AH, PAPADOPOULOS S, PODESVA C: Structure of quassin. Tetrahedron Lett. (1960) 20:25-33.
26. KUPCHAN SM, BRITTON RW, ZIEGLER MF, SIGEL CW: Bruceantin, a new potent antileukemic simaroubolide from Brucea antidysenterica. J. Org. Chem. (1973) 38(1):178-179.
27. SPINO C: The ever-challenging quassinoids. Synlett (2006) 1:23-32.
28. DUNBAR DC, LI X-C, MUHAMMAD I: Antimalarial and antifungal alkaloids from plants. In: Biomaterials from Aquatic and Terrestrial Organisms. Fingerman M, Nagabhushanam R (Eds), Science Publishers, Inc., New Hampshire (2006):207-254.
29. VIEIRA IJC, BRAZ-FILHO R: Quassinoids: structural diversity, biological activity and synthetic studies. In: Studies in Natural Product Chemistry (Volume 33). Bioactive Natural Products (Part M). Atta-ur-Rahman (Ed.), Elsevier Science Publishers, Amsterdam (2006):433-492.
30. OKANO M, FUKAMIYA N, LEE KH: Bioactive quassinoids. In: Studies in Natural Product Chemistry (Volume 23). Bioactive Natural Products, Part D. Atta-ur-Rahman (Ed.), Elsevier Science Publishers, Amsterdam (2000):285-333.
31. GUO Z, VANGAPANDU S, SINDELAR RW, WALKER LA, SINDELAR RD: Biologically active quassinoids and their chemistry: Potential leads for drug design. Curr. Med. Chem. (2005) 12(2):173-190.
32. SHARMA P, SHARMA JD: A review of plant species assessed in for anti-amoebic activity or both anti-amoebic and antiplasmodial properties. Phytother. Res. (2001) 15(1):1-17.
33. KLINKERT MQ, HEUSSLER V: The use of anticancer drugs in antiparasitic chemotherapy. Mini Rev. Med. Chem. (2006) 6(2):131-143.
34. O'NEILL MJ, BRAY DH, BOARDMAN P et al.: Plants as sources of antimalarial drugs: in vitro antimalarial activities of some quassinoids. Antimicrob. Agents Chemother. (1986) 30(1):101-104.
35. MUHAMMAD I, BEDIR E, KHAN SI et al.: A new antimalarial quassinoid from Simaba orinocensis. J. Nat. Prod. (2004) 67(5):772-777.
36. CHORDIA MD, SMITH KS, SMITH PL: Biological evaluation of 1-OH modified ailanthinone analogs as antimalarial agents. Abstracts of Papers, 232nd ACS National Meeting, San Francisco, CA, USA (10 - 14 September 2006) (2006):MEDI-562.
37. LEE KH, TANI S, IMAKURA Y: Antimalarial agents, 4. Synthesis of a brusatol analog and biological activity of brusatol-related compounds. J. Nat. Prod. (1987) 50(5):847-851.
38. MURAKAMI N, UMEZOME T, MAHMUD T et al.: Anti-malarial activities of acylated bruceolide derivatives. Bioorg. Med. Chem. Lett. (1998) 8(5):459-462.
39. MURAKAMI N, SUGIMOTO M, KAWANISHI M et al.: New Semisynthetic quassinoids with in vivo antimalarial activity J Med Chem. (2003) 46(4):638-641
40. CHAN KL, CHOO CY, ABDULLAH NR: Semisynthetic 15-O-acyl- and 1,15-di-O-acyleurycomanones from Eurycoma longifolia as potential antimalarials. Planta Med. (2005) 71(10):967-969.
41. FUKAMIYA N, LEE KH, MUHAMMAD I et al.: Structure-activity relationships of quassinoids for eukaryotic protein synthesis. Cancer Lett. (2005) 220(1):37-48.
42. LIAO LL, KUPCHAN SM, HORWITZ SB: Mode of action of the antitumor compound bruceantin, an inhibitor of protein synthesis. Mol. Pharmacol. (1976) 12(1):167-176.
43. FRESNO M, GONZALES A, VAZQUEZ D, JIMENEZ A: Bruceantin, a novel inhibitor of peptide bond formation. Biochim. Biophys. Acta, Nuclic Acids Protein Synthesis (1978) 518(1):104-112.
44. WILLINGHAM W III, CONSIDINE RT, CHANEY SG, LEE KH, HALL IH: Reversibility of protein synthesis inhibition by quassinoid antineoplastic agents in a rabbit reticulocyte system. Biochem. Pharmacol. (1984) 33(2):330-333.
45. LIOU YF, HALL IH, OKANO M, LEE KH, CHANEY SG: Antitumor agents. XLVIII: structure-activity relationships of quassinoids as in vitro protein synthesis inhibitors of P-388 lymphocytic leukemia tumor cell metabolism. J. Pharmaceut. Sci. (1982) 71(4):430-435.
46. RODRIGUEZ-FONSECA C, AMILS R, GARRETT RA: Fine structure of the peptidyl transferase center on 23 S-like rRNAs deduced from chemical probing of antibiotic-ribosome complexes. J. Mol. Biol. (1995) 247(2):224-235.
47. KIRBY GC, O'NEILL MJ, PHILLIPSON JD, WARHURST DC: In vitro studies on the mode of action of quassinoids with activity against chloroquine-resistant Plasmodium falciparum. Biochem. Pharmacol. (1989) 38(24):4367-4374.
48. GURU PY, WARHURST DC, HARRIS A, PHILLIPSON JD: Antimalarial activity of bruceantin in vitro. Ann. Trop. Med. Parasitol. (1983) 77(4):433-435.
49. TRAGER W, POLONSKY J: Antimalarial activity of quassinoids against chloroquine-resistant Plasmodium falciparum in vitro. Am. J. Trop. Med. Hyg. (1981) 30(3):531-537.
50. KITAGAWA I, MAHMUD T, YOKOTA KI et al.: Indonesian medicinal plants. XVII. Characterization of quassinoids from the stems of Quassia indica. Chem. Pharmaceut. Bull. (1996) 44(11):2009-2014.
51. PAVANAND K, NUTAKUL W, DECHATIWONGSE T et al: In vitro antimalarial activity of Brucea javanica against multi-drug resistant Plasmodium falciparum. Planta Med. (1986) 2:108-111.
52. DOU J, MCCHESNEY JD, SINDELAR RD, GOINS DK, WALKER LA: A new quassinoid from Castela texana. J. Nat. Prod. (1996) 59(1):73-76.
53. FRANCOIS G, DIAKANAMWA C, TIMPERMAN G et al.: Antimalarial and cytotoxic potential of four quassinoids from Hannoa chlorantha and Hannoa klaineana and their structure-activity relationships. Int. J. Parasitol. (1998) 28(4):635-640.
54. WRIGHT CW, O'NEILL MJ, PHILLIPSON JD, WARHURST DC: Use of microdilution to assess in vitro antiamoebic activities of Brucea javanica fruits, Simarouba amara stem, and a number of quassinoids. Antimicrob. Agents Chemother. (1988) 32(11):1725-1729.
55. BRAY DH, BOARDMAN P, O'NEILL MJ et al.: Plants as a source of antimalarial drugs. 5. Activities of Ailanthus altissima stem constituents and of some related quassinoids. Phytother. Res. (1987) 1(1):22-24.
56. OKUNADEAL, BIKOFF RE, CASPER SJ et al.: Antiplasmodial activity of extracts and quassinoids isolated from seedlings of Ailanthus altissima (Simaroubaceae). Phytother. Res. (2003) 17(6):675-677.
57. KUO PC, DAMU AG, LEE KH, WU TS: Cytotoxic and antimalarial constituents from the roots of Eurycoma longifolia. Bioorg. Med. Chem. (2004) 12(3):537-544.
58. CHAN KL, CHOO CY, ABDULLAH NR, ISMAIL Z: Antiplasmodial studies of Eurycoma longifolia Jack using the lactate dehydrogenase assay of Plasmodium falciparum. J. Ethnopharmacol. (2004) 92(2-3):223-227.
59. CHAN KL, O'NEILL MJ, PHILLIPSON JD, WARHURST DC: Plants as sources of antimalarial drugs. Part 3. Eurycoma longifolia. Planta Med. (1986) (2): 105-107.
60. KARDONO LBS, ANGERHOFER CK, TSAURI S et al.: Studies on Indonesian medicinal plants. IV. Cytotoxic and antimalarial constituents of the roots of Eurycoma longifolia. J. Nat. Prod. (1991) 54(5): 1360-1367.
61. MONJOUR L, ROUQUIER F, ALFRED C, POLONSKY J: Therapeutic trials with the quassinoid glaucarubinone in experimental murine malaria. Comptes Rendus de l'Alcademie, des. Sciences, Serie III: Sciences de la Vie (1987) 304(6): 129-132.
62. ANG HH, CHAN KL, MAK JW: In vitro antimalarial activity of quassinoids from Eurycoma longifolia against Malaysian chloroquine-resistant Plasmodium falciparum isolates. Planta Med. (1995) 61(2):177-178.
63. PANDEY A, JOSHI BC, SHARMA RP, KHARE A: New quassinoids from Ailanthus excelsa. Med. Chem. Res. (2004) 13(8/9):781-789.
64. CHAN KL, LEE SP, SAM TW, HAN BH: A quassinoid glycoside from the roots of Eurycoma longifolia. Phytochemistry (1989) 28(10):2857-2859.
65. POLONSKY J: The constituents of the bark of Simaruba amara: isolation of a new bitter principle: simarolide. Bull. de la Soc. Chimique de Fr. (1959): 1546-1547.
66. VAN TRI M, POLONSKY J, MERIENNE C, SEVENET T: Soularubinone, a new antileukemic quassinoid from Soulamea tomentosa. J. Nat. Prod. (1981) 44(3):279-284.