Phenolic acids enzymatic lipophilization

被引:192
作者
Figueroa-Espinoza, MC
Villeneuve, P
机构
[1] CIRAD, IATE, UMR, Lipotechny Lab, F-34398 Montpellier, France
[2] ENSIA, SIARC, F-34093 Montpellier, France
关键词
phenolic acid; lipase; lipophilization; esterification; antioxidant; emulsion; multifunctional; additive;
D O I
10.1021/jf0484273
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
Lipophilization is the esterification of a lipophilic moiety (fatty acid or fatty alcohol) on different substrates (phenolic acid, sugar, protein,...), resulting in new molecules with modified hydrophilic/ lipophilic balance. This reaction can be obtained chemically or enzymatically using different enzymes. Phenolic acids possess interesting biological properties (antioxidant, chelator, free radical scavenger, UV filter, antimicrobial,...), but because of their relatively low solubility in aprotic media, their application in oil-based products is limited. Therefore, the esterification of their carboxylic acid function with a fatty alcohol enhances their hydrophobicity and results in a multifunctional amphiphilic molecule. Enzymatic lipophilization of phenolic acids is nowadays studied for potential industrial applications. Different systems have been proposed to perform the reaction yield [free or immobilized enzymes (lipase, feruloyl esterase, tannase, etc.), free or added organic solvent, addition of surfactant, microemulsion system, etc.]. Some of the functional properties of these esters have been demonstrated. This review presents a panorama of the advances in this field.
引用
收藏
页码:2779 / 2787
页数:9
相关论文
共 68 条
[1]   Triterpene alcohol and sterol ferulates from rice bran and their anti-inflammatory effects [J].
Akihisa, T ;
Yasukawa, K ;
Yamaura, M ;
Ukiya, M ;
Kimura, Y ;
Shimizu, N ;
Arai, K .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2000, 48 (06) :2313-2319
[2]   Conformational analysis: a tool for the elucidation of the antioxidant properties of ferulic acid derivatives in membrane models [J].
Anselmi, C ;
Centini, M ;
Andreassi, M ;
Buonocore, A ;
La Rosa, C ;
Facino, RM ;
Sega, A ;
Tsuno, F .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2004, 35 (05) :1241-1249
[3]   EVALUATION OF THE ANTIOXIDANT AND PROOXIDANT ACTIONS OF GALLIC ACID AND ITS DERIVATIVES [J].
ARUOMA, OI ;
MURCIA, A ;
BUTLER, J ;
HALLIWELL, B .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1993, 41 (11) :1880-1885
[4]   Constituents of the pods of Piliostigma thonningii [J].
Baratta, MT ;
Ruberto, G ;
Tringali, C .
FITOTERAPIA, 1999, 70 (02) :205-208
[5]   ALKYL FERULATES IN WOUND-HEALING POTATO-TUBERS [J].
BERNARDS, MA ;
LEWIS, NG .
PHYTOCHEMISTRY, 1992, 31 (10) :3409-3412
[6]  
BRAND-WILLIAMS W, 1995, FOOD SCI TECHNOL-LEB, V28, P25
[7]   Enzymatic esterifications of functionalized phenols for the synthesis of lipophilic antioxidants [J].
Buisman, GJH ;
van Helteren, CTW ;
Kramer, GFH ;
Veldsink, JW ;
Derksen, JTP ;
Cuperus, FP .
BIOTECHNOLOGY LETTERS, 1998, 20 (02) :131-136
[8]   Differential distribution of ferulic acid to the major plasma constituents in relation to its potential as an antioxidant [J].
Castelluccio, C ;
Bolwell, GP ;
Gerrish, C ;
RiceEvans, C .
BIOCHEMICAL JOURNAL, 1996, 316 :691-694
[9]   Effect of ethyl esterification of phenolic acids on low-density lipoprotein oxidation [J].
Chalas, J ;
Claise, C ;
Edeas, M ;
Messaoudi, C ;
Vergnes, L ;
Abella, A ;
Lindenbaum, A .
BIOMEDICINE & PHARMACOTHERAPY, 2001, 55 (01) :54-60
[10]  
CHEETHAM PSJ, 2000, Patent No. 6066311