Abstract
The fractionation through bioguided antileishmanial activity of the dichloromethane extract of Cassia fistula fruits (Leguminosae) led to the isolation of the active isoflavone biochanin A, identified by spectroscopic methods. This compound showed 50% effective concentration (EC50) value of 18.96 μg/mL against promastigotes of Leishmania (L.) chagasi. The cytotoxicity of this substance against peritoneal macrophages resulted in an EC50 value of 42.58 μg/mL. Additionally, biochanin A presented an anti-Trypanosoma-cruzi activity, resulting in an EC50 value of 18.32 μg/mL and a 2.4-fold more effectiveness than benznidazole. These results contribute with novel antiprotozoal compounds for future drug design studies.

Similar content being viewed by others
References
Agrawal GD, Rizv SA, Gupta PC, Tewari JD (1972) Structure of fistulic acid—a new colouring matter from the pods of Cassia fistula. Planta Med 21:151–155
Asseleih LMC, Hernandez OH, Sanchez JR (1990) Seasonal variations in the content of sennosides in leaves and pods of two Cassia fistula populations. Phytochemistry 29:3095–3099
Bahorun T, Neergheen SV, Aruoma IO (2005) Phytochemical constituents of Cassia fistula. African J Biotech 4:1530–1540
Balaña-Fouce R, Reguera RM, Cubría C, Ordóñez D (1998) The pharmacology of leishmaniasis. Gen Pharma 30:435–443
Benavides A, Bassarello C, Montoro P, Vilegas W, Piacente S, Pizza C (2007) Flavonoids and isoflavonoids from Gynerium sagittatum. Phytochemistry 68:1277–1284
Chan-Bacab JM, Peña-Rodriguez ML (2001) Plant natural products with leishmanial activity. Nat Prod Rep 18:674–688
Conceição K, Konno K, Richardson M, Antoniazzi MM, Jared C, Daffre S, Camargo AC, Pimenta DC (2006) Isolation and biochemical characterization of peptides presenting antimicrobial activity from the skin of Phyllomedusa hypochondrialis. Peptides 27:3092–3099
Croft SL, Seifert K, Yardle V (2006) Current scenario of drug development for leishmaniasis. Indian J Med Res 123:399–410
Iyengar MA, Pendse GS, Narayana N (1966) Bioassay of Cassia fistula. L. (Aragvadha). Planta Med 14:288–301
Kashiwada Y, Iizuka H, Yoshioka K, Chen RF, Nonaka GI, Nishioka I (1990) Occurrence of enantiomeric proanthocyanidins in the leguminosae plants, Cassia fistula and C. javanica. Chem Pharm Bull 38:888–893
Lane JE, Ribeiro-Rodrigues R, Suarez CC, Bogitsh BJ, Jones MM, Singh PK, Carter CE (1996) In vitro trypanocidal activity of tetraethylthiuram disulfide and sodium diethylamine-N-carbodithioate on Trypanosoma cruzi. Am Soc Trop Med Hyg 55:263–266
Lopes NP, Kato MJ, Yoshida M (1999) Antifungal constituents from roots of Virola surinamensis. Phytochemistry 51:29–33
Luximon-Ramma A, Bahorun T, Soobrattee MA, Aruoma OI (2002) Antioxidant activities of phenolic, proanthocyanidin, and flavonoid components in extracts of Cassia fistula. J Agric Food Chem 50:5042–5047
Moreira DR, Lima-Leite AC, Pinheiro-Ferreira PM, da Costa PM, Costa-Lotufo LV, de Moraes MO, Brondani DJ, Pessoa CO (2007) Synthesis and antitumour evaluation of peptidyl-like derivatives containing the 1,3-benzodioxole system. Eur J Med Chem 42:351–357
Morimoto S, Nonaka G, Chen RF, Nishoka I (1988) Tannins and related compounds. LXI. Isolation and structures of novel Bi- and triflavanoids from the Leaves of Cassia fistula. Chem Pharm Bull 36:39–47
Santos SA, Carvalho MG, Braz-Filho R (1995) Unambiguous 1H and 13C assignments of isoflavones from Virola caducifolia. J Braz Chem Soc 6:349–352
Singh S, Sivakumar R (2004) Challenges and new discoveries in the treatment of leishmaniasis. J Infect Chemother 10:307–315
Tada H, Shiho O, Kuroshima K (1986) An improved colorimetric assay for interleukin 2. J Immunol Methods 9:157–65
Tadesmir D, Kaiser M, Brun R, Yardley V, Schmidt TJ, Tosun F, Rüedi P (2006) Antitrypanosomal and antileishmanial activities of flavonoids and their analogues: in vitro, in vivo, structure-activity relationship, and quantitative structure–activity relationship studies. Antimicrob Agents Chem 50:1352–1364
Tempone AG, Borborema SE, de Andrade HF Jr, de Amorim GNC, Yogi A, Carvalho CS, Bachiega D, Lupo FN, Bonotto SV, Fischer DC (2004) Antiprotozoal activity of Brazilian plant extracts from isoquinoline alkaloid-producing families. Phytomedicine 12:382–390
Tempone AG, Sartorelli P, Fernandes F, Mady C (2007) Natural toxins to antitrypanosomal drugs: an overview of new drug prototypes for American trypanosomiasis. Cardiovasc Hematol Agents Med Chem 5:222–235
Trouiller P, Torreele E, Olliaro P, White N, Foster S, Wirth D, Pecoul B (2001) Drugs for neglected diseases: a failure of the market and a public health failure? Trop Med Int Health 6:945–951
Torssell KBG (1997) Natural product chemistry. Apotekarsocieteten—Swedish Pharmaceutical Society, Stockholm, pp 72–75
Viegas JC, Rezende A, Silva DHS, Castro-Gambôa I, Bolzani VS, Barreiro EJ, Miranda ALP, Alexandre-Moreira MS, Young MCM (2006) Aspectos químicos, biológicos e etnofarmacológicos do gênero Cassia. Quim Nova 29:1279–1286
Yadava RN, Verma VJ (2003) A new biologically active flavone glycoside from the seeds of Cassia fistula (Linn.). J Asian Nat Prod Res 5:57–61
Acknowledgments
This work was supported by grants from Fundação de Amparo à Pesquisa do Estado de São Paulo (01/05023-1) and Instituto Adolfo Lutz (project number CCD-BM 16/2004). The experiments comply with the current laws of Brazil where they were performed.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Sartorelli, P., Carvalho, C.S., Reimão, J.Q. et al. Antiparasitic activity of biochanin A, an isolated isoflavone from fruits of Cassia fistula (Leguminosae). Parasitol Res 104, 311–314 (2009). https://doi.org/10.1007/s00436-008-1193-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00436-008-1193-z

