Chemical characterisation of the constituents of Eugenia protenta McVaugh and leishmanicidal activity of dimethylxanthoxylin

Abstract The chemical study of Eugenia protenta McVaugh extracts performed by classical and high-performance liquid chromatography techniques and spectral methods has led to the identification of known triterpenoids, flavonoids and an acetophenone derivative (dimethylxanthoxylin). The effect of dimethylxanthoxylin on Leishmania (Leishmania) amazonensis was evaluated against the promastigotes forms after 96 h of treatment. Dimethylxanthoxylin reduced 57 and 59% of the promastigotes growth when treated with 50 and 100 μg/mL solutions, respectively (IC50 117.35 μg/mL or 52.3 μM). Cytotoxicity experiments using MTT assays showed that this substance did not promote cell death after 24 h of treatment. Dimethylxanthoxylin was active on the promastigotes and could be a promising agent for treating leishmaniasis.

[1]  F. A. Carvalho,et al.  Syzygium cumini (L.) Skeels essential oil and its major constituent α-pinene exhibit anti-Leishmania activity through immunomodulation in vitro. , 2015, Journal of ethnopharmacology.

[2]  S. Sundar,et al.  Elucidation of Cellular Mechanisms Involved in Experimental Paromomycin Resistance in Leishmania donovani , 2014, Antimicrobial Agents and Chemotherapy.

[3]  Robert Newton,et al.  A Review of Preventative Methods against Human Leishmaniasis Infection , 2013, PLoS neglected tropical diseases.

[4]  J. G. M. Costa,et al.  Atividade leishmanicida in vitro de Eugenia uniflora e Momordica charantia , 2013 .

[5]  E. Andrade,et al.  Eugenia uniflora L. Essential Oil as a Potential Anti-Leishmania Agent: Effects on Leishmania amazonensis and Possible Mechanisms of Action , 2013, Evidence-based complementary and alternative medicine : eCAM.

[6]  S. Croft,et al.  Leishmaniasis chemotherapy--challenges and opportunities. , 2011, Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases.

[7]  G. Guilhon,et al.  Chemical variability of the volatiles from the leaves of Eugenia protenta McVaugh (Myrtaceae) growing wild in the North of Brazil , 2011 .

[8]  I. A. Medeiros,et al.  Effects of extract, fractions and 2,3-dihydromyricetin-3-O-α-L-rhamnoside from Pradosia huberi (Ducke) Ducke on rat isolated mesenteric arteries , 2010 .

[9]  F. Frézard,et al.  Pentavalent Antimonials: New Perspectives for Old Drugs , 2009, Molecules.

[10]  J. H. Lago,et al.  CONSTITUÍNTES FENÓLICOS POLARES DE Schinus terebinthifolius RADDI (ANACARDIACEAE) , 2007 .

[11]  Y. Kuo,et al.  Separation and Determination of Chemical Constituents in the Roots of Rhus Javanica L. Var. Roxburghiana , 2005 .

[12]  J. Barbosa-Filho,et al.  A review of natural products with antileishmanial activity. , 2005, Phytomedicine : international journal of phytotherapy and phytopharmacology.

[13]  E. Schenkel,et al.  Triterpenes and triterpenoidal glycosides from the fruits of Ilex paraguariensis (Maté) , 2004 .

[14]  M. Nair,et al.  Novel Lipid‐Peroxidation‐ and Cyclooxygenase‐Inhibitory Tannins from Picrorhiza kurroa Seeds , 2004, Chemistry & biodiversity.

[15]  F. Hsu,et al.  Two tannins from Phyllanthus tenellus , 1998 .

[16]  S. Mahato,et al.  13C NMR spectra of pentacyclic triterpenoids--a compilation and some salient features , 1994 .

[17]  Nisha Singh,et al.  Natural product based leads to fight against leishmaniasis. , 2014, Bioorganic & medicinal chemistry.

[18]  A. Saluja,et al.  ISOLATION OF STIGMASTEROL AND β­SITOSTEROL FROM PETROLEUM ETHER EXTRACT OF AERIAL PARTS OF AGERATUM CONYZOIDES (ASTERACEAE) , 2011 .

[19]  U. Hawas,et al.  Pharmaco-chemical studies on the aqueous methanolic extract of Diospyros lotus leaves. , 2009 .

[20]  E. Breitmaier,et al.  [Carbon 13 NMR spectroscopy]. , 1976, Pharmazie in unserer Zeit.