A novel, two consecutive enzyme synthesis of feruloylated monoacyl- and diacyl-glycerols in a solvent-free system

Sun, Shangde; Liang, Shan; Liu, Yuanfa; Jin, Qingzhe; Wang, Xingguo; Zhao-min, Wang

doi:10.1007/s10529-007-9486-3

Cited by 26 publications

(24 citation statements)

References 12 publications

(13 reference statements)

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“…However, in the transesterification product, the content of lipophilic feruloylated lipids FMAG and FDAG was low 36.6 2.2 FMAG, 9.1 2.0 FDAG . A novel two consecutive enzymatic step route for FMAG and FDAG production was also found in previous report 8 . But a 10-fold excess glycerol to EF as reactant and solvent was required to obtain high FMAG and FDAG yields, which led to many by-products monoacylglycerols MAG and diacylglycerols DAG formed and made FMAG and FDAG purification very difficult.…”

Section: Introductionsupporting

confidence: 62%

“…The reactants and products were analyzed by HPLC and HPLC-ESI-MS according to the previous reports 8,15 .…”

Section: Hplc Analysismentioning

confidence: 99%

“…Feruloylated monoacylglycerols FMAG and feruloylated diacylglycerols FDAG are lipophilic feruloylated lipids of ferulic acid, which have been used as lipophilic antioxidants and UV absorbers in food and other fields 10,11 . As ferulic acid is a heat-sensitive phenolic acid and susceptible to oxidation, which makes enzymatic synthesis of FMAG and FDAG become an attractive alternative 5,8 .…”

Section: Introductionmentioning

confidence: 99%

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Enhanced Enzymatic Preparation of Lipophilic Feruloylated Lipids Using Distearin as Feruloyl Acceptors: Optimization by Response Surface Methodology

Sun¹,

Zhou²

2014

J. Oleo Sci.

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Section: Introductionsupporting

confidence: 62%

“…The reactants and products were analyzed by HPLC and HPLC-ESI-MS according to the previous reports 8,15 .…”

Section: Hplc Analysismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Enhanced Enzymatic Preparation of Lipophilic Feruloylated Lipids Using Distearin as Feruloyl Acceptors: Optimization by Response Surface Methodology

Sun¹,

Zhou²

2014

J. Oleo Sci.

Self Cite

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“…Since the choice of organic solvents based on minimization of acyl migration may conlict with maximization of transesteriication, acyl migration is usually minimized by reducing reaction times [85]. With increasing concern for the environment, synthesis of PL in solvent-free systems [86][87][88] and ionic liquids systems [89] has been extensively studied. The enzymatic synthesis of vanillyl-PUFA esters from ish oil and vanillyl alcohol in acetone solvent medium was studied by [10].…”

Section: Enzyme Reactions In Organic Solvent Media (Osm)mentioning

confidence: 99%

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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“…Esterification is one way of modifying the physical properties of FA. Many feruloylated compounds are synthesized by lipases or FAEs to increase their hydrophobicity (Vafiadi et al 2008;Thörn et al 2011;Sun et al 2007bSun et al , 2009). On the other hand, little has been done to synthesize feruloylated compounds with high solubility in water.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of highly water-soluble feruloyl diglycerols by esterification of an Aspergillus niger feruloyl esterase

Kikugawa

Tsuchiyama

Kai

et al. 2012

Appl Microbiol Biotechnol

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Ferulic acid (FA) is a component of plant cell walls that has applications in food, cosmetic, and health products, but its applications are limited by its high insolubility. We synthesized water-soluble FA derivatives by esterification of FA with diglycerol (DG) using feruloyl esterase purified from a commercial enzyme preparation produced by Aspergillus niger. The major reaction product, FA-DG1, was determined to be γ-feruloyl-α,α'-DG by NMR and electrospray ionization mass spectrometry analyses. FA-DG1 is a sticky liquid whose water solubility (>980 mg/ml) is dramatically higher than that of FA (0.69 mg/ml). Suitable conditions for esterification of FA with DG were 100 mg of FA in the presence of 1 g of DG and 0.1 ml of 1 M phosphate buffer (pH 6.0) at 50 °C under reduced pressure. Under these conditions, 168 mg of feruloyl DGs (FA-DG1, 2, and 3) was obtained, corresponding to a 95 % conversion rate of FA. We also developed a batch method which resulted in synthesis of 729 mg of feruloyl DGs and 168 mg of diferuloyl DGs from 600 mg of FA and 1 g of DG (corresponding to conversion of 69 % of the FA to feruloyl DGs and 21 % of the FA to diferuloyl DGs). As an anti-oxidant, feruloyl DGs were essentially equal to FA and butyl hydroxytoluene in scavenging 1,1-diphenyl-2-picrylhydrazyl radicals. In contrast, the scavenging abilities of diferuloyl DGs were twice those of feruloyl DGs.

show abstract

A novel, two consecutive enzyme synthesis of feruloylated monoacyl- and diacyl-glycerols in a solvent-free system

Cited by 26 publications

References 12 publications

Enhanced Enzymatic Preparation of Lipophilic Feruloylated Lipids Using Distearin as Feruloyl Acceptors: Optimization by Response Surface Methodology

Enhanced Enzymatic Preparation of Lipophilic Feruloylated Lipids Using Distearin as Feruloyl Acceptors: Optimization by Response Surface Methodology

Synthesis and Characterization of Phenolic Lipids

Synthesis of highly water-soluble feruloyl diglycerols by esterification of an Aspergillus niger feruloyl esterase

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