Lipase-catalyzed synthesis of two new antioxidants: 4-- and 3--palmitoyl chlorogenic acids

C. Lorentz (1) , Amélie Dulac (2) , G. Pencreac'H (1) , F. Ergan (1) , Pascal Richomme (2) , S. Soultani-Vigneron (1)

1 MMS - Mer, molécules et santé EA 2160
2 SONAS - Substances d'Origine Naturelle et Analogues Structuraux

Chlorogenic acid (5-caffeoyl quinic acid (CQA)) extracted from (44%, w/w) with 98% purity, was acylated with palmitic acid by Novozym 435 to yield mono-acylated CQA. Acylation of CQA was achieved in 2-methyl-2-butanol at 60°C, and yielded two mono-acylated products: a major product acylated at the -4 of the quinic moiety (4--palmitoyl chlorogenic acid) and a minor product acylated at the -3 (3--palmitoyl chlorogenic acid). The bioconversions obtained in 7 days ranged from 14 to 60% and were influenced by the molar ratio of palmitic acid/CQA, which ranged from 10 to 80. The regioselectivity (4--palmitoyl/3--palmitoyl ratio) of the reaction was also affected by the molar ratio, and ranged from 90 to 70%. The scavenging activities against 1,1-diphenyl-2-picryl-hydrazyl radicals demonstrated that these palmitoyl CQA derivatives are associated with antioxidant activity (70% vs CQA).

Mots clés: Acylation; Chlorogenic acid; Novozym 435; Palmitic acid; Scavenging activity

Domaines: Chimie; Sciences du Vivant [q-bio]

C. Lorentz, Amélie Dulac, G. Pencreac'H, F. Ergan, Pascal Richomme, et al.. Lipase-catalyzed synthesis of two new antioxidants: 4-- and 3--palmitoyl chlorogenic acids. Biotechnology Letters, 2010, 32 (12), pp.1955-1960. ⟨10.1007/s10529-010-0386-6⟩. ⟨hal-00618196⟩