A bioactive biflavonoid from Campnosperma panamense

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Fitoterapia 75 (2004) 764 – 767 www.elsevier.com/locate/fitote

Short report

A bioactive biflavonoid from Campnosperma panamense B. Wenigera,*, C. Vonthron-Se´ne´cheaua, G.J. Arangob, M. Kaiserc, R. Brunc, R. Antona a

Laboratoire de Pharmacognosie, UMR N87081, Faculte´ de Pharmacie, Universite´ Louis Pasteur, BP 60024, 67401 Strasbourg, France b Facultad de Quı´mica Farmace´utica, Universidad de Antioquia, Apartado 1226, Medellı´n, Colombia c Swiss Tropical Institute, Socinstrasse 57, CH-4002 Basel, Switzerland Received 18 June 2004; accepted 6 September 2004 Available online 27 October 2004

Abstract Lanaroflavone (1), a biflavonoid isolated from the methanol extract of the aerial part of Campnosperma panamense by bioguided fractionation, has been assessed for in vitro antiprotozoal activity. Lanaroflavone showed both antimalarial and leishmanicidal activities, but was inactive against Chagas disease vector, Trypanosoma cruzi. D 2004 Elsevier B.V. All rights reserved. Keywords: Campnosperma panamense; Lanaroflavone; Antiplasmodial activity; Leishmanicidal activity

1. Plant Campnosperma panamense Standl. (Anacardiaceae) leaves collected in May 2000 from Department del Valle, Colombia and identified by Dr. Robert T. Gonzalez, University del Valle. A voucher specimen (BW067) has been deposited in the Herbarium of the Universidad del Valle, Cali (CUVC).

* Corresponding author. Tel.: +33 390 244238; fax: +33 390 244311. E-mail address: [email protected] (B. Weniger). 0367-326X/$ - see front matter D 2004 Elsevier B.V. All rights reserved. doi:10.1016/j.fitote.2004.09.015

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2. Uses in traditional medicine No medicinal use has been reported for this species, but several Anacardiaceae are used traditionally as antiplasmodial in South America [1]. The tree is used as a commercial source of timber on the Pacific coast of Colombia [2]. The antimalarial activity of leaf extract has been previously shown [3].

3. Previously isolated classes of constituents No phytochemical study has yet been reported for C. panamense. Lanaroflavone has been previously reported from Lanaria lanata and Ouratea semiserrata [4,5].

4. Tested materials Lanaroflavone 1 (4j,5,5U,7,7U-pentahydroxy-4V,8U-biflavonyl ether) (6.9 mg from 140 g of dry plant material).

5. Studied activity Antiplasmodial activity was evaluated following the microculture radioisotope technique [6] modified by Ridley [7], while leishmanicidal activity was evaluated

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Table 1 Biological activities of lanaroflavone Compounds

Antiplasmodial activitya IC50 (Ag/ml)

Leishmanicidal activityb IC50 (Ag/ml)

Antitrypanosomial activityc IC50 (Ag/ml)

Lanaroflavone Chloroquine Artemisinin Miltefosin Benznidazole

0.2 0.069 0.003 – –

3.9 – – 0.19 –

N90 – – – 0.44

Data shown are values from two replicate experiments. a P. falciparum K1 resistant strain. b L. donovani amastigotes. c T. cruzi Tulahuen strain trypomastigotes.

using the axenic amastigote assay [8,9]. Antitrypanosomial activity was evaluated by colorimetric reaction (h-galactosidase/CPRG-Nonidet) using trypomastigotes of Trypanosoma cruzi Tulahuen strain C2C4 containing the h-galactosidase (Lac Z) gene [10].

6. Results Reported in Table 1.

7. Conclusion Lanaroflavone exhibited good antiplasmodial activity in vitro against Plasmodium falciparum K1 chloroquine-resistant strain and moderate leishmanicidal activity against L. donovani amastigotes, but did not show antitrypanosomial activity.

Aknowledgments The authors want to thank Vanessa Douville for technical assistance and the ECOS/ ICFES/COLCIENCIAS/ICETEX program for financial support.

References [1] [2] [3] [4] [5] [6]

Deharo E, Bourdy G, Quenevo C, Mun˜oz V, Ruiz G, Sauvain M. J Ethnopharmacol 2001;77:91. Poyry J. Cespedesia 1982;11:7. Weniger B, Robledo S, Arango GJ, Deharo E, Aragon R, Munoz V, et al. J Ethnopharmacol 2001;78:193. Dora G, Edwards JM. J Nat Prod 1991;54:796. Velandia JR, De Carvalho MG, Braz-Filho R, Werle AA. Phytochem Anal 2002;13:283. Desjardins RE, Canfield CJ, Haynes JD, Chulay JD. Antimicrob Agents Chemother 1979;16:710.

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[7] Ridley RG, Hofheinz W, Matile H, Jaquet C, Dorn A, Masciadri R, et al. Antimicrob Agents Chemother 1996;40:1846. [8] Brendle JJ, Outlaw A, Kumar A, Boykin DW, Patrick DA, Tidwell RR, et al. Antimicrob Agents Chemother 2002;46:797. [9] Werbovetz KA, Brendle JJ, Sackett DL. Mol Biochem 1999;98:53. [10] Jones SM, Urch JE, Brun R, Harwood JL, Berry C, Gilbert IH. Bioorg Med Chem 2004;12:683.

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