Lipase-catalyzed synthesis of structured phenolic lipids in solvent-free system using flaxseed oil and selected phenolic acids as substrates

Sorour, Noha M.; Karboune, Salwa; Saint-Louis, Richard; Kermasha, Sélim

doi:10.1016/j.jbiotec.2011.12.002

Cited by 36 publications

(33 citation statements)

References 36 publications

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“…The enzymatic processes can be used in the production of fats and oils containing beneicial faty acids and phenolic compounds. Some reviews have given a comprehensive understanding and shown a whole outline on the enzymatic synthesis of PL [41][42][43][44][45][46].…”

Section: Enzymatic Synthesis Of Phenolic Lipids (Pls)mentioning

confidence: 99%

“…Hong et al [47] studied the esteriication of vanillyl alcohol with conjugated linoleic acid under vacuum in solvent-free system. Further studies on the enzymatic synthesis of structured phenolic lipids in SFM have also been conducted by [34,44,92]. In these studies, phenolic acids were esteriied with faty acids resulted in the formation of more lipophilic constituents that can be used as a nutraceutical product.…”

Section: Enzyme Reactions In Solvent-free Medium (Sfm)mentioning

confidence: 99%

“…Diferent studies presented the efect of chemical structure of phenolic compounds which are hydroxylated or methoxylated derivatives of cinnamic, phenyl acetic and benzoic acids on the conversion yield [34,35,42,44]. The presence of a hydroxyl group in the sn-2 position has a negative inductive efect.…”

Section: Substrate Composition and Concentration (Molar Ratio)mentioning

confidence: 99%

“…Kumari et al [118] reported that carrying the reaction at the optimum agitation speed can limit the external mass transfer limitations, in the case of immobilized enzymes, where the reactants need to difuse from the bulk oil to the external surface of the enzyme particles and from there, subsequently to the interior pores of the catalyst. In addition [44] investigated the efect of agitation speed on the conversion yield of phenolic lipids synthesized from laxseed oil and DHCA; the results have shown that the conversion yield increased signiicantly from 39 to 62.5% when the agitation speed was increased from 50 to 150 rpm, before it was decreased to 44.8% at agitation speed of 250 rpm. The low conversion yield could be atributed to insuicient agitation rate, a condition in which a hydrophilic layer of glycerol may be formed around the enzyme, limiting hence the mass transfer rate of the oil to the surface of the lipase.…”

Section: Agitation Speedmentioning

confidence: 99%

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Synthesis and Characterization of Phenolic Lipids

Roby¹

2017

Phenolic Compounds - Natural Sources, Importance and Applications

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Omega-3 polyunsaturated faty acids (ω3 PUFAs) from ish oils promote well-established health and antiaging beneits that justify their use as functional ingredients in dietary supplements, healthy foods, and nutraceutical products. Dietary supply is needed because human metabolism exhibits limited to synthesize ω3 PUFAs. However, the practical use of such lipids as food ingredients is often limited due to their high susceptibility to oxidation, which is responsible for the undesirable of-lavor and odor of rancid oils, associated with the loss of nutritional value. Produced phenolic lipids were a good solution for all these problems. These phenolic lipids are preferentially produced by enzymatic bioprocesses that exhibit high selectivity toward polyfunctional substrates and mild reaction conditions compared with chemical synthesis pathways. This chapter presents the acylation of phenolic compounds and lipids using enzyme under various operating conditions. In conclusion, the acylation of lipids with natural phenolic compounds resulted in the formation of a lipophilic ester that should be able to stabilize the oil, fats, and emulsions against oxidation. Acylation of lipids to phenolic compounds that have antioxidant properties thus protects the lipids from oxidation, and the phenolic lipid derivatives carry the combined health beneicial properties of lipids and the phenolic molecules.

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Section: Enzymatic Synthesis Of Phenolic Lipids (Pls)mentioning

confidence: 99%

Section: Enzyme Reactions In Solvent-free Medium (Sfm)mentioning

confidence: 99%

Section: Substrate Composition and Concentration (Molar Ratio)mentioning

confidence: 99%

Section: Agitation Speedmentioning

confidence: 99%

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Synthesis and Characterization of Phenolic Lipids

Roby¹

2017

Phenolic Compounds - Natural Sources, Importance and Applications

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“…CALB has been shown to be useful for the biocatalytic transesterification of triacylglycerols and ferulate esters to form feruloylated lipids (Compton et al, 2000;Sorour et al, 2012). Ferulic acid and its esters are naturally occurring compounds that serve as components of hemicelluloses and are found in the suberin and waxy surfaces of leaves and other plant components.…”

Section: Introductionmentioning

confidence: 99%

Continuous, packed-bed, enzymatic bioreactor production and stability of feruloyl soy glycerides

Compton¹,

Goodell²,

Grall³

et al. 2015

Industrial Crops and Products

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Enzymatic Synthesis and Antioxidant Activity of 1‐Caffeoylglycerol Prepared from Alkyl Caffeates and Glycerol

Meng

et al. 2018

J Americ Oil Chem Soc

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Caffeic acid (CA) as a strong antioxidant has lower solubility in nonpolar media, which limits its application in the food industry. To increase the lipophilicity of CA, 1-caffeoylglycerol (1-CG) was synthesized by lipasecatalyzed transesterification of alkyl caffeates in solvent-free system and its antioxidant capacity was investigated. Methyl caffeate was screened as the appropriate substrate from tested alkyl caffeates with a yield of 90.63%. Ethyl acetate was used for extracting 1-CG from enzymatic reactants and could be easily recycled. The produced 1-CG had 2.5-and 10-fold lower values of half maximal inhibitory concentration (IC 50 ) (10.86 and 3.99 μM) than butylated hydroxyanisole by 1,1-diphenyl-2-picrylhydrazyl radical scavenging and β-carotene-linoleic acid assays, respectively. Thus, 1-CG is an excellent antioxidant for application in the functional food industry. Using alkyl caffeates and glycerol as substrates to produce 1-CG catalyzed by immobilized lipase in a solvent-free system is a simple, selective, and safe bioprocess that can readily be achieved in the food industry, and the product 1-CG could be widely applied in food, nutraceutical, and biotechnological products.

show abstract

Lipase-catalyzed synthesis of structured phenolic lipids in solvent-free system using flaxseed oil and selected phenolic acids as substrates

Cited by 36 publications

References 36 publications

Synthesis and Characterization of Phenolic Lipids

Synthesis and Characterization of Phenolic Lipids

Continuous, packed-bed, enzymatic bioreactor production and stability of feruloyl soy glycerides

Enzymatic Synthesis and Antioxidant Activity of 1‐Caffeoylglycerol Prepared from Alkyl Caffeates and Glycerol

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