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Planta Med 2003; 69(5): 420-424
DOI: 10.1055/s-2003-39706
Original Paper
Pharmacology
© Georg Thieme Verlag Stuttgart · New York

Antifungal, Antiprotozoal, Cytotoxic and Piscicidal Properties of Justicidin B and a New Arylnaphthalide Lignan from Phyllanthus piscatorum

Jürg Gertsch1 , Rebekka Thöni Tobler1 , Reto Brun2 , Otto Sticher1 , Jörg Heilmann1
  • 1Department of Chemistry and Applied BioSciences, Institute of Pharmaceutical Sciences, Swiss Federal Institute of Technology (ETH) Zurich, Zürich, Switzerland
  • 2Swiss Tropical Institute, Basel, Switzerland
Further Information

Publication History

Received: August 19, 2002

Accepted: January 5, 2003

Publication Date:
12 June 2003 (online)

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Abstract

Using activity against Candida albicans as a lead, the bioactivity-guided fractionation of the dichloromethane extract of Phyllanthus piscatorum led to the isolation of the arylnaphthalide lignan justicidin B (1), which was found to be present in high amounts, and a new C-11 hydroxylated derivative that we named piscatorin (2). We provide evidence that justicidin B (1) is the main active principle of P. piscatorum, showing the same biological effects that were found for the raw extracts. Justicidin B inhibited the growth of the pathogenic fungi Aspergillus fumigatus (MIC ≥ 1 μg/mL), Aspergillus flavus (MIC ≥ 12 μg/mL), and Candida albicans (MIC ≥ 4 μg/mL), but was not effective against Cryptococcus neoformans and Blastoschizomyces capitatus. Justicidin B also exhibited strong activity against the trypomastigote form of Trypanosoma brucei rhodesiense (IC50 = 0.2 μg/mL) and moderate activity against Trypanosoma cruzi (IC50 = 2.6 μg/mL). Testing against Plasmodium falciparum showed only weak activity. This is the first report on the in vitro fungicidal and antiprotozoal effects of justicidin B. In addition, both compounds exhibited a non-specific cytotoxicity in neoplastic and primary cell cultures. No antibacterial effects were detected. Both compounds were piscicidal against zebra fish and it is shown for the first time that piscatorin (2) and justicidin B (1) are the piscicidal principles of P. piscatorum, exhibiting a potency that is comparable to rotenone.

Key words

Phyllanthus piscatorum - Euphorbiaceae - justicidin B - lignan - antifungal - Candida albicans - fish poison

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PD Dr. Jörg Heilmann

Swiss Federal Institute of Technology (ETH) Zurich

Institute of Pharmaceutical Sciences

Winterthurerstr. 190

8057 Zürich

Switzerland

Phone: +41-1-6356049

Fax: +41-1-6356882

Email: joerg.heilmann@pharma.anbi.ethz.ch

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