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Molecules 2014, 19(10), 16959-16975; doi:10.3390/molecules191016959

Antioxidant, 5-Lipoxygenase Inhibitory and Cytotoxic Activities of Compounds Isolated from the Ferula lutea Flowers

1
Université de Toulouse, Faculté de Pharmacie de Toulouse, Laboratoire des IMRCP UMR CNRS 5623, Université Paul-Sabatier, 118 route de Narbonne, F-31062 Toulouse, France
2
Laboratoire de Chimie Hétérocyclique, Produits Naturels et Réactivité (CHPNR), Equipe Chimie Médicinale et Produits Naturels, Département de Chimie, Faculté des Sciences de Monastir, Université de Monastir, Avenue de l'Environnement, 5019 Monastir, Tunisia
3
Laboratory of Genetic, Biodiversity and Valorization of Bioresources, Higher Institute of Biotechnology of Monastir, University of Monastir, 5019 Monastir, Tunisia
*
Authors to whom correspondence should be addressed.
Received: 27 August 2014 / Revised: 11 October 2014 / Accepted: 15 October 2014 / Published: 22 October 2014
(This article belongs to the Section Medicinal Chemistry)
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Abstract

A phytochemical investigation of the Ferula lutea (Poir.) Maire flowers has led to the isolation of a new compound, (E)-5-ethylidenefuran-2(5H)-one-5-O-β-D-glucopyranoside (1), designated ferunide, 4-hydroxy-3-methylbut-2-enoic acid (2), reported for the first time as a natural product, together with nine known compounds, verbenone-5-O-β-D-glucopyranoside (3), 5-O-caffeoylquinic acid (4), methyl caffeate (5), methyl 3,5-O-dicaffeoylquinate (6), 3,5-O-dicaffeoylquinic acid (7), isorhamnetin-3-O-α-L-rhamnopyranosyl(1→6)-β-D-glucopyranoside, narcissin (8), (−)-marmesin (9), isoimperatorin (10) and 2,3,6-trimethylbenzaldehyde (11). Compounds 310 were identified for the first time in Ferula genus. Their structures were elucidated by spectroscopic methods, including 1D and 2D NMR experiments, mass spectroscopy and X-ray diffraction analysis (compound 2), as well as by comparison with literature data. The antioxidant, anti-inflammatory and cytotoxic activities of isolated compounds were evaluated. Results showed that compound 7 exhibited the highest antioxidant activity with IC50 values of 18 ± 0.5 µmol/L and 19.7 ± 0.7 µmol/L by DPPH radical and ABTS radical cation, respectively. The compound 6 exhibited the highest anti-inflammatory activity with an IC50 value of 5.3 ± 0.1 µmol/L against 5-lipoxygenase. In addition, compound 5 was found to be the most cytotoxic, with IC50 values of 22.5 ± 2.4 µmol/L, 17.8 ± 1.1 µmol/L and 25 ± 1.1 µmol/L against the HCT-116, IGROV-1 and OVCAR-3 cell lines, respectively. View Full-Text
Keywords: Ferula lutea; secondary metabolites; phenolic; antioxidant; anti-inflammatory; cytotoxic Ferula lutea; secondary metabolites; phenolic; antioxidant; anti-inflammatory; cytotoxic
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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. (CC BY 4.0).

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MDPI and ACS Style

Znati, M.; Ben Jannet, H.; Cazaux, S.; Souchard, J.P.; Harzallah Skhiri, F.; Bouajila, J. Antioxidant, 5-Lipoxygenase Inhibitory and Cytotoxic Activities of Compounds Isolated from the Ferula lutea Flowers. Molecules 2014, 19, 16959-16975.

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