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Terpenoids isolated from Tunisian Nigella sativa L. essential oil with antioxidant activity and the ability to inhibit nitric oxide production

Bourgou Soumaya, Pichette André, Lavoie Serge, Marzouk Brahim et Legault Jean. (2012). Terpenoids isolated from Tunisian Nigella sativa L. essential oil with antioxidant activity and the ability to inhibit nitric oxide production. Flavour and Fragrance Journal, 27, (1), p. 69-74.

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URL officielle: http://dx.doi.org/doi:10.1002/ffj.2085

Résumé

Fractionation of the essential oil from the seeds of Nigella sativa (Ranunculaceae) led to the isolation of four terpenoids: trans‐ (1), cis‐sabinene hydrate methyl ether (2), 1,2‐epoxy‐menth‐4‐ene (3) and 1,2‐epoxy‐menth‐4(8)‐ene (4). Structure elucidation was performed using NMR (1D and 2D NMR) experiments and mass spectral data. Compounds 3 and 4 are reported for the first time as natural products. Bioactivities of the compounds were assessed. The four compounds exhibit antioxidant activity in vitro, as assessed by the oxygen radical absorbance capacity test. Moreover, compounds 1, 2 and 4 displayed strong ability to inhibit oxidative stress in human skin WS‐1 fibroblasts cells, with IC50 values of 0.32, 0.005 and 0.43 µ m, respectively. In addition, the four tested compounds significantly inhibited nitric oxide release by lipopolysaccharide‐activated RAW 264.7 macrophages. The results show that the most effective compound was cis‐sabinene hydrate methyl ether (2). In addition, the cis‐configurated compound (2) exerted stronger activities in comparison with the trans‐configurated compound (1), suggesting geometric stereoselectivity for the biological activities.

Type de document:Article publié dans une revue avec comité d'évaluation
ISSN:08825734
Volume:27
Numéro:1
Pages:p. 69-74
Version évaluée par les pairs:Oui
Date:Janvier 2012
Identifiant unique:10.1002/ffj.2085
Sujets:Sciences naturelles et génie > Sciences naturelles > Biologie et autres sciences connexes
Sciences naturelles et génie > Sciences naturelles > Chimie
Département, module, service et unité de recherche:Départements et modules > Département des sciences fondamentales
Mots-clés:Nigella sativa, monoterpenes, cis-sabinene hydrate methyl ether, antioxidant activity, NO inhibiting production activity
Déposé le:01 sept. 2021 17:48
Dernière modification:01 sept. 2021 17:48
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