Enzymatic synthesis of fatty esters in 5-caffeoyl quinic acid

Guyot, Bernard; Gueule, Dominique; Pina, Michel; Graille, Jean; Farines, Vincent; Farines, M.

doi:10.1002/(sici)1438-9312(200002)102:2<93::aid-ejlt93>3.0.co;2-b

Cited by 30 publications

(13 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Hydroxyl groups associated with phenolic compounds are the most common and often the most effective free radical scavengers in foods [10], as they may readily donate an electron or the hydrogen to intercept and convert free radicals to a more stable compound. There are several reports on the chemical as well as enzymatic lipophilization of phenolics to produce functionalized phenols, where different phenolics were used as substrates [11][12][13][14][15][16]. These reported compounds were found to exhibit good antiradical activity and therefore can act as promising antioxidants in lipophilic medium.…”

Section: Introductionmentioning

confidence: 99%

Chemo‐enzymatic synthesis and evaluation of novel structured phenolic lipids as potential lipophilic antioxidants

Kunduru

Shanker

Ravinder

et al. 2010

Euro J Lipid Sci & Tech

View full text Add to dashboard Cite

Chemo-enzymatic synthesis of structured triacylglycerol bearing ferulic acid as a phenolic acid at sn-1/3 position is described in the present work. Four compounds of varying chain lengths, namely 3-(4-hydroxy-3-methoxy-phenyl)-acrylic acid-2,3-bis-hexanoyloxy-propyl ester, 3-(4-hydroxy-3-methoxy-phenyl)-acrylic acid-2,3-bis-octanoyloxy-propyl ester, 3-(4-hydroxy-3-methoxy-phenyl)-acrylic acid-2,3-bis-dodecanoyloxy-propyl ester, and 3-(4-hydroxy-3-methoxy-phenyl)-acrylic acid-2,3-bis-9-octadecenoyloxy-propyl ester were synthesized, and their structures were confirmed by IR, NMR, and MS. Antioxidant activity of the structured phenolic lipids were evaluated using three different in vitro antioxidant assays such as 2, 2-diphenyl-1-picrylhydrazyl free radical (DPPH ) scavenging, antioxidant potency in lipid matrix using rancimat, and by the rate of inhibition of autoxidation of linoleic acid in micelles. Ferulic acid and dodecylgallate were used as reference antioxidant compounds. DPPH assay did not show any improvement in the antioxidant activity of ferulic acid with lipophilic modification. However, the antioxidant potency of the structured phenolic lipids measured by rancimat method as well as by the rate of inhibition of autoxidation of linoleic acid in micelle showed improvement in antioxidant activity compared to ferulic acid. This is probably due to better solubility of the synthesized phenolic lipids in a hydrophobic medium and appropriate anchorage in Tween 20 micelle. The observed activities of the structured phenolic lipids are comparable to dodecyl gallate in rancimat assay, but superior to dodecyl gallate in Tween 20 micellar system.

show abstract

Section: Introductionmentioning

confidence: 99%

Chemo‐enzymatic synthesis and evaluation of novel structured phenolic lipids as potential lipophilic antioxidants

Kunduru

Shanker

Ravinder

et al. 2010

Euro J Lipid Sci & Tech

View full text Add to dashboard Cite

show abstract

“…In this specific case, glycerol rosmarinate ester is poorly soluble in the different lipophilic acyl donors. Addition of organic solvent able to solubilize the two substrates with different polarities is frequently used to improve the lipase-catalyzed reactions [42,43]. However, the choice of solvent is of prime importance as it can also affect the enzyme activity.…”

Section: Third Step: Synthesis Of Compoundmentioning

confidence: 99%

Regioselective synthesis of diacylglycerol rosmarinates and evaluation of their antioxidant activity in fibroblasts

Durand¹,

Bayrasy²,

Laguerre³

et al. 2015

Euro J Lipid Sci & Tech

View full text Add to dashboard Cite

A series of new model of lipophilized phenolic compound derived from the rosmarinic acid was synthesized: 1,2-diacylglycerol rosmarinate (RDAG) with different alkyl chain lengths from ve to eighteen carbons. These RDAG were obtained through a chemo-enzymatic synthesis: A chemical esterication based on the Mitsunobu reaction, followed by a lipase-catalyzed transesterication to link the different lipophilic moieties. The antioxidant abilities of these molecules were assessed on reactive oxygen species (ROS) overexpressing broblasts. The RDAG 12 displayed the best antioxidant activity of the series. Lengthening of the lipid chain beyond twelve carbon atoms leads to a decrease in the antioxidant activity, thus conrming the occurrence of a cut-off effect. Antioxidant RDAG 12 activity was then compared with that of vitamins C and E, rosmarinic acid and decyl rosmarinate (R 10 ). The order of activity was R 10 > RDAG 12 > RDAG 5 > rosmarinic acid  vitamin C  vitamin E. At 5 mM, R 10 exhibited an even better antioxidant activity than the combination of vitamins C and E at 5 mM each. These results conrm, rstly, that catechol structure is very effective in terms of antioxidant activity and secondly, that linking an appropriate hydrophobic domain is a powerful strategy to synthesize effective antioxidants. Practical applications: Phenolic compounds (especially phenolic acids and avonoids) are potent antioxidants that may play an important role as well in biological system (to prevent some risk factors associated with cancers, cardiovascular, and neurodegenerative diseases) as in formulated-lipid dispersions. However, their activity is often limited by low solubility and stability in such systems. Lipophilization of phenolic compounds may increase their solubility in lipophilic matrices, conferring better antioxidant protection for food or non-food application. In biological system, lipophilization may contribute to easier penetration of antioxidants through lipid bilayer of cell membranes, which can signicantly increase their bioavailability. Thus, lipophilic phenolic derivatives provide a perspective of substances with maintained or improved biological properties for food, cosmetic, and pharmaceutical applications, playing an important role in the development of new drugs or food additives. (Résumé d'auteur

show abstract

“…Synthesis of CQA alkyl esters results from the esterification of the CQA carboxylic acid group with the primary OH group of a fatty alcohol. This reaction was first investigated by direct lipasecatalysed esterification using fatty alcohols as aliphatic chain donors [3]. Saturated alcohols with 8 to 18 carbon chain length were tested as aliphatic chain donors, the biocatalyst was Novozym 435m (immobilised Candida antarctica lipase B from Novozymes, Denmark) and the reaction was performed in 2-methyl-2-butanol.…”

Section: Enzymatic and Chemo-enzymatic Synthesismentioning

confidence: 99%

Production and properties of chlorogenic acid lipophilic esters

Pencreach¹,

Lorentz

Ergan

et al. 2012

Lipid Technology

View full text Add to dashboard Cite

Chlorogenic acid is a dietary polyphenol with important bioactivities. However, its high hydrophilicity prevents its applications as an antioxidant for lipid protection in a complex matrix such as food. Grafting an aliphatic chain onto chlorogenic acid, so‐called lipophilisation, via lipase‐catalysed esterification represents an efficient means of increasing its lipophilicity. A series of alkyl esters with various chain lengths were produced and used to explore the structure‐antioxidant activity relationship of amphiphilic antioxidants. Data obtained from complex systems (oil‐in‐water emulsion and cell culture) concluded that short or medium chain lengths enhance the antioxidant activity while longer chains tend to decrease the antioxidant ability of chlorogenic acid. This phenomenon remains to be fully explained. Acyl esters, in which the carboxylic acid group remains free were also produced and were shown to be interesting antioxidant candidates as well as useful tools for the understanding of antioxidant activities.

show abstract

Enzymatic synthesis of fatty esters in 5-caffeoyl quinic acid

Cited by 30 publications

References 9 publications

Chemo‐enzymatic synthesis and evaluation of novel structured phenolic lipids as potential lipophilic antioxidants

Chemo‐enzymatic synthesis and evaluation of novel structured phenolic lipids as potential lipophilic antioxidants

Regioselective synthesis of diacylglycerol rosmarinates and evaluation of their antioxidant activity in fibroblasts

Production and properties of chlorogenic acid lipophilic esters

Contact Info

Product

Resources

About