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Molecules 2011, 16(5), 3469-3478; doi:10.3390/molecules16053469
Article

Thiophene Derivatives with Antileishmanial Activity Isolated from Aerial Parts of Porophyllum ruderale (Jacq.) Cass.

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Received: 21 February 2011 / Revised: 22 March 2011 / Accepted: 20 April 2011 / Published: 26 April 2011
(This article belongs to the Section Metabolites)
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Abstract

Porophyllum ruderale (Jacq.) Cass. is a plant native to Brazil and in the northwest region of the state of Paraná, Brazil, aerial parts of P. ruderale have been used popularly in the treatment of lesions caused by Leishmania sp.. In this study the antileishmanial and cytotoxic activities of the crude extract, fractions, and isolated compounds from aerial parts of P. ruderale was evaluated. The dichloromethane extract was submitted to chromatography to yield compounds active against Leishmania amazonensis. Their structures were established by comparison of their spectroscopic data with literature values. The activities of crude extract against promastigote and axenic amastigote forms of L. amazonensis (IC50) were 60.3 and 77.7 μg/mL, respectively. Its cytotoxic activity against macrophage cells (CC50) was 500 μg/mL. The thiophene derivatives isolated were: 5-methyl-2,2':5',2"-terthiophene (compound A) and 5'-methyl–[5–(4–acetoxy-1–butynyl)]–2,2'-bithiophene (compound B). The activity of compound A against promastigote and axenic amastigote forms were 7.7 and 19.0 μg/mL and of compound B were 21.3 and 28.7 μg/mL, respectively. The activity of the isolated compounds against promastigote and axenic amastigote forms was better than that of the crude extract and more selective against protozoa than for macrophage cells.
Keywords: Porophyllum ruderale; antileishmanial activity; thiophene derivatives; Leishmania amazonensis Porophyllum ruderale; antileishmanial activity; thiophene derivatives; Leishmania amazonensis
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Takahashi, H.T.; Novello, C.R.; Ueda-Nakamura, T.; Filho, B.P.D.; Palazzo de Mello, J.C.; Nakamura, C.V. Thiophene Derivatives with Antileishmanial Activity Isolated from Aerial Parts of Porophyllum ruderale (Jacq.) Cass.. Molecules 2011, 16, 3469-3478.

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