Enzymatic Synthesis of Lipophilic Rutin and Vanillyl Esters from Fish Byproducts

Mbatia, Betty; Kaki, Shiva Shanker; Mattìasson, Bo; Mulaa, Francis; Adlercreutz, Patrick

doi:10.1021/jf200867r

Cited by 41 publications

(49 citation statements)

References 33 publications

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“…The enzymatic synthesis of phenolic lipids has been reported previously in Refs. [10,45,[47][48][49]. A lot of enzymes can be used in the synthesis of PL and selectivity is the most important characteristics of enzymes used in phenolic lipid synthesis.…”

Section: Enzymatic Synthesis Of Phenolic Lipids (Pls)mentioning

confidence: 99%

“…Lipase-catalyzed hydrolysis can be used for the preparation of faty acids from oils, especially for the selective hydrolysis and concentrations of PUFAs from edible oils [10]. Furthermore, lipase catalyzed hydrolysis reactions only in the presence of amount of water.…”

Section: Hydrolysismentioning

confidence: 99%

“…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]. Lipase-catalyzed esteriication of vanillyl alcohol with diferent faty acids was carried out by [51] to the synthesis of capsiate analogs.…”

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

confidence: 99%

“…Thin-layer chromatography has been used for initial qualitative analyses of substrates by employing a wide range of organic solvent mixtures. Products from the esteriication reactions are characterized and analyzed by TLC using silica gel G-25 plates [10,47]. The elution solvents used depend on the nature of synthesized compounds.…”

Section: Analysis and Characterization Of Phenolic Lipidsmentioning

confidence: 99%

“…The elution solvents used depend on the nature of synthesized compounds. In the study of [10], the elution solvent used was chloroform/methanol mixture (80:20, v/v) and pure chloroform; the plates were visualized under UV light (254 nm), meanwhile, in the work of Hong et al [47], the elution solvent was n-hexane/diethyl ether/formic acid (160:40:5.5, v/v/v), and the plate was visualized with 0.2% (w/v) 2,7 dichloroluorescein in methanol solution under UV light.…”

Section: Analysis and Characterization Of Phenolic Lipidsmentioning

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: Hydrolysismentioning

confidence: 99%

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

confidence: 99%

Section: Analysis and Characterization Of Phenolic Lipidsmentioning

confidence: 99%

Section: Analysis and Characterization Of Phenolic Lipidsmentioning

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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Chemo‐enzymatic synthesis of sapienic acid esters of functional phenolics and evaluation of their antioxidant and cytotoxicity activities

Kaki

Gopal

Rao

et al. 2013

Euro J Lipid Sci & Tech

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Novel fatty acid ester derivatives comprising sapienic acid [(Z)‐6‐hexadecenoic acid] and functional phenolics were synthesized following a chemo‐enzymatic approach. Sapienic acid was synthesized by Wittig coupling of triphenylphosphonium bromide salt of 6‐bromohexanoic acid and decanal with a cis specific reagent. Sapienic acid was chemo selectively esterified with six phenolic compounds to produce sapienate esters of six phenolics using a lipase in organic solvent medium. Structural characterization of the prepared fatty acid ester derivatives was done by spectral data (IR, mass spectra, and NMR). The sapienic acid ester derivatives were screened for in vitro antioxidant and cytotoxicity evaluation. These derivatives exhibited good radical scavenging activity as determined by the diphenylpicryl hydrazyl (DPPH) radical scavenging assay. Sapienic ester of hydroxytyrosol was found to exhibit highest DPPH radical scavenging activity and was greater than commercial antioxidants. Cytotoxicity evaluation against four cancer cell lines showed that three esters out of six were found to exhibit moderate cytotoxicity with coniferyl derivative being more active than the others against all the tested cell lines.

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Synthesis of novel (Z)‐methyl‐12‐aminooctadec‐9‐enoate‐based phenolipids as potential antioxidants and chemotherapeutic agents

Yarra

Kaki

Mallampalli

et al. 2015

Euro J Lipid Sci & Tech

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A series of novel phenolipids were synthesized by coupling (Z)‐methyl‐12‐aminooctadec‐9‐enoate with substituted aromatic phenolic acids. The substrate (Z)‐methyl‐12‐aminooctadec‐9‐enoate was synthesized from methyl ricinoleate employing a four‐step procedure. The synthesized phenolipids were thoroughly characterized by FT‐IR, 1H NMR, 13C NMR, ESI‐MS, and HRMS spectral analysis. The in vitro antioxidant activities of synthesized compounds were evaluated by 2, 2‐diphenyl‐1‐picrylhydrazyl radical (DPPH•), superoxide free radical scavenging activity, and lipid peroxidation inhibitory activities. The novel phenolic compounds were compared in terms of antioxidant activity with the commercial antioxidants, namely butylated hydroxy toluene (BHT) and α‐tocopherol as reference compounds. The antioxidant screening data of all the synthesized compounds revealed that DPPH free radical scavenging activity, superoxide, and lipid peroxidation inhibitory activity of caffeic and gallic acid substituted phenolipids exhibited excellent activity as compared to commercial antioxidants, BHT, and α‐tocopherol. The synthesized phenolipids were also evaluated for anticancer activities against four different cancer cell lines namely DU145, HePG2, SKOV3, MDA‐MB‐231. Among these compounds, 7a, 7b, 7d, 7e which were derived from cinnamic acid‐based phenolic acids and 8b which is derived from vanillic acid exhibited good anticancer activity against the tested cell lines. Practical applications: Lipophilization of phenolic acids improves their antioxidant and anticancer properties. The (Z)‐methyl‐12‐aminooctadec‐9‐enoate‐based phenolipids can be exploited in a number of lipophilic antioxidant and anticancer formulations. A panel of (Z)‐methyl‐12‐aminooctadec‐9‐enoate‐based phenolipids are synthesized for the first time from methyl ricinoleate, an unusual fatty acid isolated from castor oil. These compounds were evaluated for antioxidant properties, and gallic and caffeic acid‐based phenolipids exhibited extraordinary properties compared to BHT and α‐tocopherol commercially available antioxidants used in food and pharmaceutical formulations. These compounds were evaluated for anticancer activity for the first time, where these have exhibited good to moderate activity. Hence, (Z)‐methyl‐12‐aminooctadec‐9‐enoate‐based phenolipids can be exploited in a number of lipophilic antioxidant and anticancer formulations.

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Enzymatic Synthesis of Lipophilic Rutin and Vanillyl Esters from Fish Byproducts

Cited by 41 publications

References 33 publications

Synthesis and Characterization of Phenolic Lipids

Synthesis and Characterization of Phenolic Lipids

Chemo‐enzymatic synthesis of sapienic acid esters of functional phenolics and evaluation of their antioxidant and cytotoxicity activities

Synthesis of novel (Z)‐methyl‐12‐aminooctadec‐9‐enoate‐based phenolipids as potential antioxidants and chemotherapeutic agents

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