Lipase-catalyzed synthesis of two new antioxidants: 4-O- and 3-O-palmitoyl chlorogenic acids.
Chlorogenic acid (5-caffeoyl quinic acid (CQA)) extracted from Hydrangea macrophylla (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 C-4 of the quinic moiety (4-O-palmitoyl chlorogenic acid) and a minor product acylated at the C-3 (3-O-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-O-palmitoyl/3-O-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).
Lorentz
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C
Laboratoire Mer, Molécules, Santé EA 2160 Université du Maine, Institut Universitaire de Technologie de Laval, 52 rue des Drs Calmette et Guérin, BP 2045, 53020, Laval Cedex 9, France.
Dulac
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A
Pencreac'h
G
G
Ergan
F
F
Richomme
P
P
Soultani-Vigneron
S
S
D000975:Antioxidants / Q000737:chemistry* / Q000378:metabolism*; D001711:Biotransformation; D002726:Chlorogenic Acid / Q000031:analogs & derivatives* / Q000378:metabolism*; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D006358:Hot Temperature; D031966:Hydrangea / Q000737:chemistry*; D008049:Lipase / Q000378:metabolism*; D019308:Palmitic Acid / Q000378:metabolism*; D000439:Pentanols / Q000378:metabolism
D000975:Antioxidants; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D000439:Pentanols; D019308:Palmitic Acid; D002726:Chlorogenic Acid; C032765:tert-amyl alcohol; C093667:Novozyme 435; D008049:Lipase