Biogenic trypanocidal sesquiterpenes: Lead compounds to design future trypanocidal drugs - A mini review

DARU, Journal of Pharmaceutical Sciences

Volumn 21, Issue 1, 2013, Pages

  Saeidnia, Soodabeh ^a   Gohari, Ahmad Reza ^a   Haddadi, Azita ^b  

^a TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^b UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

Elatol; Lactones; Sesquiterpene; Treatment; Trypanosomiasis

Indexed keywords

ALKALOID; ANTHRAQUINONE; ANTITRYPANOSOMAL AGENT; APIGENIN; BENZNIDAZOLE; CARYOPHYLLENE DERIVATIVE; CATECHIN; DEHYDROLEUCODINE; DICENTRINE; DITERPENE; FURANONE DERIVATIVE; HELENALIN; HERBACEOUS AGENT; LACTONE DERIVATIVE; MEXICANIN; OLEANOLIC ACID; QUERCETIN; SESQUITERPENE DERIVATIVE; TERPENE; TRITERPENE DERIVATIVE; UNCLASSIFIED DRUG; URSOLIC ACID; XANTHONE DERIVATIVE;

ANTIPROTOZOAL ACTIVITY; CONCENTRATION RESPONSE; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG ISOLATION; DRUG STRUCTURE; EPIMASTIGOTE; IC 50; IN VITRO STUDY; NONHUMAN; REVIEW; STRUCTURE ACTIVITY RELATION; TRYPANOSOMA; TRYPANOSOMA BRUCEI; TRYPANOSOMA CRUZI;

EID: 84878234643     PISSN: 15608115     EISSN: 20082231     Source Type: Journal    
DOI: 10.1186/2008-2231-21-35     Document Type: Review

References (44)

1. Trypanocidal and leishmanicidal activities of sesquiterpene lactones from Ambrosia tenuifolia Sprengel (Asteraceae). Sülsen VP, Frank FM, Cazorla SI, Anesini CA, Malchiodi EL, Freixa B, Vila R, Muschietti LV, Martino VS, Antimicrob Agents Ch 2008 52 2415 2419 10.1128/AAC.01630-07 (Pubitemid 351915670)
2. The Impact of Chagas disease control in Latin America-a review. Dias JCP, Silveira AC, Schofield CJ, Mem Inst Oswaldo Cruz 2002 97 603 612 10.1590/S0074-02762002000500002 12219120 (Pubitemid 135746072)
3. A critical review on Chagas disease chemotherapy. Coura JR, De Castro SL, Mem Inst Oswaldo Cruz 2002 97 3 24 11992141 (Pubitemid 135746197)
4. Chemotherapy of Chagas' disease: status and new developments. Cerecetto H, Gonzalez M, Curr Top Med Chem 2002 2 1187 1213 10.2174/1568026023393066 12171581
5. Current status and future prospects for a vaccine against American trypanosomiasis. Garg N, Bhatia V, Expert Rev Vaccines 2005 4 867 880 10.1586/14760584.4.6.867 16372882 (Pubitemid 43040907)
6. Current chemotherapy of human African trypanosomiasis. Docampo R, Moreno SN, Parasitol Res 2003 90 Suppl 1 10 S13 12811544
7. Neglected disease-African sleeping sickness: Recent synthetic and modeling advances. Paliwal SK, Verma AN, Paliwal S, Sci Pharm 2011 79 389 428 10.3797/scipharm.1012-08 21886894
8. Equivalence trial of melarsoprol and nifurtimox monotherapy and combination therapy for the treatment of second-stage Trypanosoma brucei gambiense sleeping sickness. Bisser S, Nsiesi FX, Lejon V, Preux PM, Van Nieuwenhove S, Miaka Mia Bilenge C, J Infect Dis 2007 195 322 329 10.1086/510534 17205469 (Pubitemid 46146108)
9. Effectiveness of a 10-day melarsoprol schedule for the treatment of late-stage human African trypanosomiasis: confirmation from a multinational study (impamel II). Schmid C, Richer M, Bilenge CM, Josenando T, Chappuis F, Manthelot CR, J Infect Dis 2005 191 1922 1931 10.1086/429929 15871127 (Pubitemid 40705401)
10. African trypanosomiasis (sleeping sickness) http://www.who.int/ mediacentre/factsheets/fs259/en/ (accessed October 2006)
11. New developments in human African trypanosomiasis. Brun R, Balmer O, Curr Opin Infect Dis 2006 19 415 420 10.1097/01.qco.0000244045.93016.b1 16940863 (Pubitemid 44338099)
12. Bioactive constituents from Dracocephalum subcapitatum. Saeidnia S, Gohari AR, Ito M, Kiuchi F, Honda G, Z Naturforsch 2005 60 22 24
13. Flavonoid constituents of Dracocephalum kotschyi growing in Iran and their trypanocidal activity. Gohari AR, Saeidnia S, Matsuo K, Uchiyama N, Yagura T, Ito M, Honda G, J Nat Med 2003 57 250 252 (Pubitemid 38186135)
14. Trypanocidal diterpene with novel skeleton from Dracocephalum komarovi. Uchiyama N, Ito M, Kiuchi F, Honda G, Takeda Y, Khodzhimatov OK, Ashurmetov OA, Tetrahedron Lett 2004 45 531 533 10.1016/j.tetlet.2003.10.202 (Pubitemid 38010160)
15. Antitrypanosomal and antileishmanial activities of flavonoids and their analogues: in vitro, in vivo, structure-activity relationship, and quantitative structure-activity relationship studies. Tasdemir D, Kaiser M, Bruner R, Yardley V, Schmidt TJ, Tosun F, Ruedi P, Antimicrob Agents Chemother 2006 50 1352 1364 10.1128/AAC.50.4.1352-1364.2006 16569852
16. Mode of action of natural and synthetic drugs against Trypanosoma cruzi and their interaction with the mammalian host. Maya JD, Cassels BK, Iturriaga-Vasquez P, Ferreira J, Faundez M, Galanti N, Ferreira A, Morrello A, Comp Biochem Physiol 2007 146 601 620 10.1016/j.cbpa.2006.03.004 (Pubitemid 46341910)
17. Dewick PM, Medicinal Natural Products, a biosynthetic approach UK: John Wiley & Sons Ltd 2009
18. New sesquiterpene hydroperoxides with trypanocidal activity from Pogostemon cablin. Kiuchi F, Matsuo K, Ito M, Qui TK, Honda G, Chem Pharm Bull(Tokyo) 2004 52 1495 1496 10.1248/cpb.52.1495 (Pubitemid 41364436)
19. Antichagastic activities of natural products against Trypanosoma cruzi. Uchiyama N, J Health Sci 2009 55 31 39 10.1248/jhs.55.31
20. Natural products and Chagas' disease: a review of plant compounds studied for activity against Trypanosoma cruzi. Izumi E, Ueda-Nakamura T, Dias Filho DP, Nat Prod Rep 2011 28 809 823 10.1039/c0np00069h 21290079
21. Trypanocidal monoterpenes, Lead compounds to design future trypanocidal drugs. Saeidnia S, Gohari AR, Studies in Natural Product Chemistry, Volume Volume 37 Netherland: Elsevier, Rahman A-u, 2012 173 190
22. Sesquiterpene lactones: Structural diversity and their biological activities. Chaturvedi D, Opportunity, Challenge and Scope of Natural Products in Medicinal Chemistry, Volume 10 India: Research Signpost 2011 313 334
23. Psilostachyin C: a natural compound with trypanocidal activity. Sülsen VP, Frank FM, Cazorla SI, Barrera P, Freixa B, Vila R, Sosa MA, Malchiodi EL, Muschietti LV, Martino VS, Int J Antimicrob Agents 2011 37 536 543 10.1016/j.ijantimicag.2011.02.003 21497061
24. Antiproliferative effect and ultrastructural alterations Induced by psilostachyin on Trypanosoma cruzi. Sülsen V, Barrera P, Muschietti L, Martino V, Sosa M, Molecules 2010 15 545 553 10.3390/molecules15010545 20110908
25. The trypanocidal effect of sesquiterpene lactones helenalin and mexicanin on cultured epimastigotes. Jimenez-Ortiz V, Brengio SD, Giordano O, Tonn C, Sanchez M, Burgos MH, Sosa MA, J Parasitol 2005 91 170 174 10.1645/GE-3373 15856894 (Pubitemid 40804317)
26. The sesquiterpene lactone dehydroleucodine (DhL) affects the growth of cultured epimastigotes of Trypanosoma cruzi. Brengio SD, Belmonte SA, Guerreiro E, Giordano OS, Pietrobon EO, Sosa MA, J Parasitol 2000 86 407 412 10780563 (Pubitemid 30208404)
27. An unusual dimeric guaianolide with antiprotozoal activity and further sesquiterpene lactones from Eupatorium perfoliatum. Maas M, Hensel A, da Costa FB, Brun R, Kaiser M, Schmid TJ, Phytochemistry 2011 72 635 644 10.1016/j.phytochem.2011.01.025 21329950
28. Antiprotozoal Activity of Neurolaena lobata. Berger I, Passreiter CM, Caceres A, Kubelka W, Phytother Res 2001 15 327 330 10.1002/ptr.782 11406857 (Pubitemid 32613102)
29. Trypanocidal sesquiterpenes from Lychnophora species. De Oliveira AB, Saúde DA, Perry KSP, Duarte DS, Raslan DS, Boaventura MAD, Chiari E, Phytother Res 1996 10 292 295 10.1002/(SICI)1099-1573(199606)10:4<292::AID- PTR834>3.0.CO;2-O (Pubitemid 26195879)
30. Cytotoxic and anti-infective sesquiterpenes present in Plagiochila disticha (Plagiochilaceae) and Ambrosia peruviana (Asteraceae). Aponte JC, Yang H, Vaisberg AJ, Castillo D, Málaga E, Verástegui M, Casson LK, Stivers N, Bates PJ, Rojas R, Fernandez I, Lewis WH, Sarasara C, Sauvain M, Gilman RH, Hammond GB, Planta Med 2010 76 705 707 10.1055/s-0029-1240681 19960415
31. Trypanocidal activity of chemical constituents from Lychnophora salicifolia Mart. Jordao CO, Vichnewski W, De Souza GEP, Albuquerque S, Lopes JLC, Phytother Res 2003 18 332 334
32. Antiprotozoal activity of drimane and coloratane sesquiterpenes towards Trypanosoma brucei rhodesiense and Plasmodium falciparum In Vitro. Wube AA, Bucar F, Gibbons S, Asres K, Rattray L, Croft SL, Phytother Res 2010 24 1468 1472 10.1002/ptr.3126 20878696
33. Isolation of elatol from Laurencia microcladia and its palatability to the sea urchin Echinometra lucunter. Lhullier C, Donnangelo A, Caro M, Palermo JA, Horta PA, Falkenberg M, Schenkel EP, Biochem Syst Ecol 2009 37 254 259 10.1016/j.bse.2009.04.004
34. In vitro anti-trypanosomal activity of elatol isolated from red seaweed Laurencia dendroidea. Veiga-Santos P, Pelizzaro-Rocha KJ, Santos AO, Ueda-Nakamura T, Filho BPD, Silva SO, Sudatti DB, Bianco EM, Pereira RC, Nakamura CV, Parasitology 2010 137 1661 1670 10.1017/S003118201000034X 20546638
35. Monoterpene hydroperoxides with trypanocidal activity from Chenopodium ambrosioides. Kiuchi F, Itano Y, Uchiyama N, Honda G, Tsubouchi A, Nakajima-Shimada J, Aoki T, J Nat Prod 2002 65 509 512 10.1021/np010445g 11975490 (Pubitemid 34456934)
36. The mechanism is action of hydrogen peroxide on bacterial metabolism. Mucchielli A, Saint-Lebe L, CR Acad Sci Hebd Seances Acad Sci D 1976 283 435 438
37. Quantitative structure antiprotozoal activity relationships of sesquiterpene lactones. Schmidt TJ, Nour AMM, Khalid SA, Kaiser M, Brun R, Molecules 2009 14 2062 2076 10.3390/molecules14062062 19513006
38. Bioactive compounds of the volatile oil of Dracocephalum kotschyi. Saeidnia S, Gohari AR, Hadjiakhoondi A, Shafiee A, Z Naturforsch 2007 62 793 796 (Pubitemid 351153286)
39. Two new monoterpene glycosides and trypanocidal terpenoids from Dracocephalum kotschyi. Saeidnia S, Gohari AR, Uchiyama N, Ito M, Honda G, Kiuchi F, Chem Pharm Bull(Tokyo) 2004 52 1249 1250 10.1248/cpb.52.1249 (Pubitemid 41327524)
40. Trypanocidal activity of oil of the young leaves of Nepeta cataria L. obtained by solvent extraction. Saeidnia S, Gohari AR, Hadjiakhoondi A, J Med Plants 2008 7 suppl 4 54 57
41. Trypanocidal and antileukaemic effects of the essential oils of Hagenia abyssinica, Leonotis ocymifolia, Moringa stenopetala, and their main individual constituents. Nibret E, Wink M, Phytomedicine 2010 17 911 920 10.1016/j.phymed.2010.02.009 20359874
42. Effect of elatol, isolated from red seaweed Laurencia dendroidea, on Leishmania amazonensis. Dos Santos AO, Veiga-Santos P, Ueda-Nakamura T, Filho BP, Sudatti DB, Bianco EM, Pereira RC, Nakamura CV, Mar Drugs 2010 8 2733 2743 10.3390/md8112733 21139841
43. Trypanocidal action of (-)-elatol involves an oxidative stress triggered by mitochondria dysfunction. Desoti VC, Lazarin-Bidóia D, Sudatti DB, Pereira RC, Alonso A, Ueda-Nakamura T, Dias Filho BP, Nakamura CV, Silva Sde O, Mar Drugs 2012 10 1631 1646 10.3390/md10081631 23015766
44. Anti-oxidative trypanocidal drugs, myth or reality. Saeidnia S, Daru 2013 21 21 10.1186/2008-2231-21-21 23497417