Abstract
The sesquiterpenes selina-1,3,7(11)-trien-8-one and oxidoselina-1,3,7(11)-trien-8-one were isolated from the essential oil of Eugenia uniflora L. leaves. The structures were elucidated using spectrometric methods (UV, GC–MS, NMR, and specific optical rotation). The relationship between antioxidant activity, as determined by DPPH assay, and the cytotoxic effect was evaluated using tumor cells, namely lung adenocarcinoma epithelial cells (A549) and human hepatoma carcinoma cells (HepG2), as well as a model of normal human lung fibroblast cells (IMR90). Both compounds did not show prominent free-radical scavenging activity according to DPPH assay, and did not inhibit lipid peroxidation in Wistar rat brain homogenate. The isolated compounds showed pro-oxidative effects and cytotoxicity in relation to the IMR90 cell line.
Highlights
Eugenia uniflora L. (Myrtaceae), popularly known in Brazil as pitangueira, is a small tree species widely distributed in South and Central America [1,2]
The GC–MS analytical chromatogram of the essential oil obtained in the present work is even very similar to that obtained from leaves of the tree cultivated in Nigeria, which were used in a chemical study by Weyerstahl (1988) [8]
The essential oil sample (7.0 g) was fractionated on a hexane packed silica gel 60 (240–400 mesh, Merck) column chromatography eluted with hexane/ethyl acetate mixtures in a gradient of increasing polarity
Summary
Eugenia uniflora L. (Myrtaceae), popularly known in Brazil as pitangueira, is a small tree species widely distributed in South and Central America [1,2]. In the first isolation reports of volatile compounds from E. uniflora leaves, some volatile sesquiterpenes were obtained, such as furanodiene, isofuranoelemene, curzerene, germacrene B, γ-elemene, selina-4(14),7(11)-diene, β-elemene, caryophyllene, germacrene D, bicyclogermacrene, β-selinene, atractylone, germacrone, selina-1,3,7(11)-trien-8-one (1), and oxidoselina-1,3,7(11)-trien-8-one (2) [7,8]. Most of these mentioned sesquiterpenes are known as volatile components of various plant species from other botanical families, especially from the Zingiberaceae (Curcuma), Burseraceae (Commiphora), and Apiaceae (Smyrnium) [9,10,11,12,13]. Otrwtaoncseesoqfuvitoelraptielenecsomfrpomounthdes laesabvieosacotfivEe. nuantiuflroarla,prsoeldinuact-s1,f3r,o7m-trmiene--8-one (1) and dtwicoinsaelsqanuditefropooreaxdnpidephsolyasf.rneolStismtnraautl-hco1te,nu3gl,r7eaw(al1v1ieet)lhs-utocrthiifedeEna.-nt8iueo-neondinflweotor(aa2s,t)r,spaewcelkirenfroatehr-i1mes,io3rel,da7dt-ietufrdfsieeirunnesg-ni8ntm-gobonicodeoleno(r1vgn)eicansantplidoeacnoctatxriloivdcsiotociolseuepsm-,ynanchdrosmpeactiofigclina-1,3,7(11)-totrhipeetnitc-w8a-loornsoeetsaq(t2iuo)i,ntwetreepcreehnniesisqoaulanetdse.daWnuesaisanslgseoscsopmnreevnseetnnottifo, thnheaerlerce,oltlahuteimornnesschuhilptrsobomeftawatnoetgeironaxpaindhtayino. txiadnaanlyt speoswfoerr and cytotoxic effects in different normal and cancerous human cells
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