title: Leishmanicidal activity of a daucane sesquiterpene isolated from Eryngium foetidum.
abstract: BACKGROUND
  Eryngium foetidum L. (Apiaceae) is a traditional herb that has been used for numerous medicinal applications, including as a treatment for parasitic infections, especially in the Neotropics from where it originates.
  
  
  OBJECTIVE
  This study evaluates the in vitro leishmanicidal and cytotoxicity activities of isolated compounds based on a bioassay-guided fractionation approach.
  
  
  METHODS
  Defatted aerial parts of E. foetidum were subjected to extraction with methanol followed by partitioning with n-hexane, ethyl acetate and 50% methanol. Then, the first two fractions were subsequently fractionated by column chromatography and HPLC. Compound identity was confirmed by mass spectrometry and NMR spectroscopy. Leishmania tarentolae (promastigotes) and L. donovani (amastigotes) were used as testing parasites. L6 rat myoblasts were used for cytotoxicity. All extracts and fractions were tested at 20 μg/mL.
  
  
  RESULTS
  The initial methanol extract showed 20% growth inhibition of L. tarentolae. Then, the n-hexane and ethyl acetate fractions were also active showing approximately 40% growth inhibition. From these two fractions, the following compounds were isolated: lasidiol p-methoxybenzoate (1), a daucane sesquiterpene; and 4-hydroxy-1,1,5-trimethyl-2-formyl-cyclohexadien-(2,5)-[α-acetoxymethyl-cis-crotonate] (2), a terpene aldehyde ester derivative. Compound 1 inhibited the growth of both L. tarentolae and L. donovani with IC₅₀ values of 14.33 and 7.84 μM, respectively; and showed no cytotoxicity (IC₅₀ > 50 μM). Compound 2 was inactive in the L. tarentolae assay (IC₅₀ > 50 μM).
  
  
  CONCLUSIONS
  This study presented the bioassay-guided fractionation with the leishmanicidal and cytotoxicity activities of two compounds isolated for the first time from an Eryngium species.
authors.affiliation: Department of Plant Biology and Pathology, Rutgers, The State University of New Jersey , New Brunswick, NJ , USA .
authors.forename: Patricio
authors.initials: P
authors.lastname: Rojas-Silva
authors.forename: Rocky
authors.initials: R
authors.lastname: Graziose
authors.forename: Brian
authors.initials: B
authors.lastname: Vesely
authors.forename: Alexander
authors.initials: A
authors.lastname: Poulev
authors.forename: Flaubert
authors.initials: F
authors.lastname: Mbeunkui
authors.forename: Mary H
authors.initials: MH
authors.lastname: Grace
authors.forename: Dennis E
authors.initials: DE
authors.lastname: Kyle
authors.forename: Mary Ann
authors.initials: MA
authors.lastname: Lila
authors.forename: Ilya
authors.initials: I
authors.lastname: Raskin
mesh_terms: D000818:Animals; D000981:Antiprotozoal Agents / Q000008:administration & dosage / Q000302:isolation & purification / Q000494:pharmacology*; D002460:Cell Line; D002845:Chromatography / Q000379:methods; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D031049:Eryngium / Q000737:chemistry*; D020128:Inhibitory Concentration 50; D007891:Leishmania / Q000187:drug effects*; D007893:Leishmania donovani / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D013058:Mass Spectrometry / Q000379:methods; D032446:Myoblasts / Q000187:drug effects / Q000378:metabolism; D032448:Myoblasts, Skeletal / Q000187:drug effects / Q000378:metabolism; D035261:Plant Components, Aerial; D051381:Rats; D012717:Sesquiterpenes / Q000008:administration & dosage / Q000302:isolation & purification / Q000494:pharmacology*; D018675:Toxicity Tests
chemical_list: D000981:Antiprotozoal Agents; D012717:Sesquiterpenes