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Planta Med 2008; 74(11): 1408-1412
DOI: 10.1055/s-2008-1081317
Natural Products Chemistry
Letter
© Georg Thieme Verlag KG Stuttgart · New York

Antiplasmodial Activity of Lignans and Extracts from Pycnanthus angolensis

Marta Abrantes1 , Tânia Mil-Homens1 , Noélia Duarte1 , Dinora Lopes2 , Pedro Cravo2 , Maria do Céu Madureira3 , Maria-José U. Ferreira1
  • 1iMed.UL, Faculdade de Farmácia, Universidade de Lisboa, Lisboa, Portugal
  • 2CMDT, Instituto de Higiene e Medicina Tropical, Universidade Nova de Lisboa, Lisboa, Portugal
  • 3Instituto Superior de Ciências da Saúde Egas Moniz, Monte de Caparica, Portugal
Further Information

Publication History

Received: April 28, 2008 Revised: June 3, 2008

Accepted: June 6, 2008

Publication Date:
31 July 2008 (online)

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Abstract

The dichloromethane, methanol and aqueous ethanol extracts of the stem bark of Pycnanthus angolensis were evaluated for their in vitro activity against the 3D7 Plasmodium falciparum strain. The CH2Cl2 extract was the most active showing an IC50 = 1.6 μg/mL. From this extract, a new dibenzylbutane lignan, threo-4,4′-dihydroxy-3-methoxylignan (1) named pycnantolol, together with the known lignans (−)-dihydroguaiaretic acid (2), heliobuphthalmin (3), talaumidin (4), hinokinin (5), the labdane-type diterpene ozic acid (6), and the steroids stigmast-4-en-6β-ol-3-one (7), β-sitosterol (8) and stigmasterol (9) were isolated. Their structures were established on the basis of physical and spectroscopic methods, including 2 D NMR experiments (COSY, HMQC, HMBC and NOESY). The antimalarial activity of compounds 1 – 7 was evaluated against 3D7 and Dd2 P. falciparum strains. Despite the significant activity displayed by the crude CH2Cl2 extract, the isolated compounds showed weaker antiplasmodial activity. The lowest IC50 value was obtained for talaumidin (4) (IC50 = 20.7 μg/mL against the Dd2-chloroquine resistant P. falciparum strain).

Key words

Pycnanthus angolensis - Myristicaceae - Lignans - antimalarial activity - Plasmodium falciparum

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Prof. Dr. Maria-José U. Ferreira

iMed.UL

Faculdade de Farmácia

Universidade de Lisboa

Av. das Forças Armadas

1600–083 Lisboa

Portugal

Phone: +351-21-794-6475

Fax: +351-21-794-6470

Email: mjuferreira@ff.ul.pt

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