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

Molecules

Mansour Znati³  Hichem Ben Jannet¹  Sylvie Cazaux³  Jean Pierre Souchard³  Féthia Harzallah Skhiri²  Jalloul Bouajila³ 

[1] 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;Laboratory of Genetic, Biodiversity and Valorization of Bioresources, Higher Institute of Biotechnology of Monastir, University of Monastir, 5019 Monastir, Tunisia; E-Mail:;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; E-Mails:

关键词: Ferula lutea;    secondary metabolites;    phenolic;    antioxidant;    anti-inflammatory;    cytotoxic;   

DOI  :  10.3390/molecules191016959

来源: mdpi

【 摘 要 】

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 3–10 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.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.