Selective Synthesis of 3-O-Palmitoyl-Silybin, a New-to-Nature Flavonolignan with Increased Protective Action against Oxidative Damages in Lipophilic Media

Archive ouverte : Article de revue

Drouet, Samantha | Doussot, Joel | Garros, Laurine | Mathiron, David | Bassard, Solène | Favre-Reguillon, Alain | Molinié, Roland | Lainé, Eric | Hano, Christophe

Edité par HAL CCSD ; MDPI

International audience. A selective acylation protocol using cerium chloride (CeCl3) as catalyst was applied to functionalize silybinin (1), a natural antioxidant flavonolignan from milk thistle fruit, in order to increase its solubility in lipophilic media while retaining its strong antioxidant activity. The selective esterification of 1 at the position 3-OH with a palmitate acyl chain leading to the formation of the 3-O-palmitoyl-silybin (2) was confirmed by both mass spectroscopy (MS) and nuclear magnetic resonance (NMR) analyses. The antioxidant activity of 1 was at least retained and even increased with the CUPRAC assay designed to estimate the antioxidant activity of both hydrophilic and lipophilic compounds. Finally, the 3-O-palmitoylation of 1, resulting in the formation of 2, also increased its anti-lipoperoxidant activity (i.e., inhibition of conjugated diene production) in two different lipophilic media (bulk oil and o/w emulsion) subjected to accelerated storage test.

Consulter en ligne

Suggestions

Du même auteur

The lignan (+)-secoisolariciresinol extracted from flax hulls is an effective protectant of linseed oil and its emulsion against oxidative damage | Hano, Christophe

The lignan (+)-secoisolariciresinol extracted from flax hulls is an effecti...

Archive ouverte: Article de revue

Hano, Christophe | 2017

Secoisolariciresinol (SECO) is a natural antioxidant lignan accumulated in large amounts in the seedcoat of flax and retained in the flaxseed cake residue during linseed oil pressing. Here SECO was extracted and purified from flax...

NMR and LC-MS-Based Metabolomics to Study Osmotic Stress in Lignan-Deficient Flax | Hamade, Kamar

NMR and LC-MS-Based Metabolomics to Study Osmotic Stress in Lignan-Deficien...

Archive ouverte: Article de revue

Hamade, Kamar | 2021-02

International audience. Lignans, phenolic plant secondary metabolites, are derived from the phenylpropanoid biosynthetic pathway. Although, being investigated for their health benefits in terms of antioxidant, antit...

Insight into the Influence of Cultivar Type, Cultivation Year, and Site on the Lignans and Related Phenolic Profiles, and the Health-Promoting Antioxidant Potential of Flax (Linum usitatissimum L.) Seeds | Garros, Laurine

Insight into the Influence of Cultivar Type, Cultivation Year, and Site on ...

Archive ouverte: Article de revue

Garros, Laurine | 2018-10

International audience. Flaxseeds are a functional food representing, by far, the richest natural grain source of lignans, and accumulate substantial amounts of other health beneficial phenolic compounds (i.e., flav...

Du même sujet

Antioxidant activities of a polyglucuronic acid sodium salt obtained from TEMPO-mediated oxidation of xanthan. | Delattre, Cédric

Antioxidant activities of a polyglucuronic acid sodium salt obtained from T...

Archive ouverte: Article de revue

Delattre, Cédric | 2015

International audience. A xanthouronic acid sodium salt called xanthouronan was produced from xanthan by regioselective oxidation with NaOCl/NaBr using 2,2,6,6-tetramethylpiperidine-1-oxy radical (TEMPO) as catalyst...

Impact of Spray-Drying on Biological Properties of Chitosan Matrices Supplemented with Antioxidant Fungal Extracts for Wine Applications | Choque, Élodie

Impact of Spray-Drying on Biological Properties of Chitosan Matrices Supple...

Archive ouverte: Article de revue

Choque, Élodie | 2019-11

International audience. Black aspergilli produce many bioactive compounds: enzymes, organic acids, and secondary metabolites. One such fungus, Aspergillus tubingensis G131, isolated from French Mediterranean vineyar...

Interactions between Kluyveromyces marxianus from cheese origin and the intestinal symbiont Bacteroides thetaiotaomicron: Impressive antioxidative effects | Ceugniez, Alexandre

Interactions between Kluyveromyces marxianus from cheese origin and the int...

Archive ouverte: Article de revue

Ceugniez, Alexandre | 2017

The effects of yeast ICluyveromyces marxianus S-2-05, of cheese origin, were assessed on the intestine anaerobe symbiont Bacteroides thetaiotaomicron ATCC 29741 to unveil any changes in its antioxidant properties. To this end, the...

Effect of roasting conditions on the antioxidant compounds of quinoa seeds | Ariel Carciochi, Ramiro

Effect of roasting conditions on the antioxidant compounds of quinoa seeds

Archive ouverte: Article de revue

Ariel Carciochi, Ramiro | 2016

International audience. The effect of different roasting conditions on the antioxidant properties and the phenolic content of quinoa seeds was studied. Advanced and final products of the Maillard reaction were also ...

Effect of germination and fermentation process on the antioxidant compounds of quinoa seeds | Carciochi, Ramiro Ariel

Effect of germination and fermentation process on the antioxidant compounds...

Archive ouverte: Article de revue

Carciochi, Ramiro Ariel | 2016

Quinoa (Chenopodium quinoa) seed has gained a great interest in the last years, mainly due to its nutritional properties and its content of antioxidant substances with health-promoting properties in humans. In this work, the effec...

Physiological and Biochemical Traits of Two Major Arabidopsis Accessions, Col-0 and Ws, Under Salinity | Leschevin, Maïté

Physiological and Biochemical Traits of Two Major Arabidopsis Accessions, C...

Archive ouverte: Article de revue

Leschevin, Maïté | 2021-06-21

International audience. Salinity affects plant growth and development as shown with the glycophyte model plant, Arabidopsis thaliana (Arabidopsis) . Two Arabidopsis accessions, Wassilewskija (Ws) and Columbia (Col-0...

Chargement des enrichissements...