The antioxidant activity of some esters of ferulic acid with the linear fatty alcohols C7, C8 (branched and linear), C9, C11, C12, C13, C15, C16, and C18 has been studied in homogeneous and heterogeneous phases. Whereas in homogeneous phase all of the alkyl ferulates possessed similar radical-scavenging abilities, in rat liver microsomes they showed striking differences, the more effective being C12 (7) (IC50 = 11.03 µM), linear C8 (3) (IC50 = 12.40 µM), C13 (8) (IC50 = 18.60 µM), and C9 (5) (IC50 = 19.74 µM), followed by C7 (2), C15 (9), C11 (6), branched C8 (4), C16 (10), and C18 (11) (ferulic acid was the less active, IC50 = 243.84 µM). All of the molecules showed similar partition coefficients in an octanol-buffer system. Three-dimensional studies (NMR in solution, modeling in vacuo) indicate that this behavior might be due to a different anchorage of the molecules with the ester side chain to the microsomal phospholipid bilayer and to a consequent different orientation/positioning of the scavenging phenoxy group outside the membrane surface against the flux of oxy radicals.

Antioxidant Activity of Ferulic Acid Alkyl Esters in a Heterophasic System: A Mechanistic Insight / Cecilia Anselmi, Marisanna Centini, Paola Granata, Alessandro Sega, Anna Buonocore, Andrea Bernini, Roberto Maffei Facino. - In: JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY. - ISSN 0021-8561. - 52:21(2004), pp. 6425-6432. [10.1021/jf049671x]

Antioxidant Activity of Ferulic Acid Alkyl Esters in a Heterophasic System: A Mechanistic Insight

P. Granata;R. MAFFEI FACINO
2004

Abstract

The antioxidant activity of some esters of ferulic acid with the linear fatty alcohols C7, C8 (branched and linear), C9, C11, C12, C13, C15, C16, and C18 has been studied in homogeneous and heterogeneous phases. Whereas in homogeneous phase all of the alkyl ferulates possessed similar radical-scavenging abilities, in rat liver microsomes they showed striking differences, the more effective being C12 (7) (IC50 = 11.03 µM), linear C8 (3) (IC50 = 12.40 µM), C13 (8) (IC50 = 18.60 µM), and C9 (5) (IC50 = 19.74 µM), followed by C7 (2), C15 (9), C11 (6), branched C8 (4), C16 (10), and C18 (11) (ferulic acid was the less active, IC50 = 243.84 µM). All of the molecules showed similar partition coefficients in an octanol-buffer system. Three-dimensional studies (NMR in solution, modeling in vacuo) indicate that this behavior might be due to a different anchorage of the molecules with the ester side chain to the microsomal phospholipid bilayer and to a consequent different orientation/positioning of the scavenging phenoxy group outside the membrane surface against the flux of oxy radicals.
Alkyl ferulates; antioxidant/radical scavenging activity; acellular and cellular models; conformational analysis; intervention in biological membranes
Settore CHIM/08 - Chimica Farmaceutica
2004
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/14346
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