Antioxidant and antibacterial activity of fatty acid vanillyl ester produced by Proteus vulgaris K80 lipase-mediated transesterification

Natalia, Agnes; Kim, Soo Jin; Kim, Hyung Kwoun

doi:10.1016/j.molcatb.2017.03.012

Cited by 15 publications

(32 citation statements)

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“…The major components of O. majorana EO, e.g., terpinen-4-ol, α-terpinol and α-pinene, have been reported for their antimicrobial and antifungal properties [21]. Additionally, the main constituents of the EO of A. herba-alba, cis - and trans -thujone and vanillyl alcohol, have been reported for their antimicrobial, anti-inflammatory, and antioxidant activities [40,41]. Oxygenated monoterpenes exhibit high antimicrobial activity on whole cell and possess antifungal effects.…”

Section: Discussionmentioning

confidence: 99%

Chemical Composition and Antimicrobial Activity of Artemisia herba-alba and Origanum majorana Essential Oils from Morocco

et al. 2019

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Essential oils (EOs) are one of the most important groups of plant metabolites responsible for their biological activities. This study was carried out to study the chemical composition and the antimicrobial effects of Artemisia herba-alba and Origanum majorana essential oils against some Gram-positive and Gram-negative bacteria, and a fungal strain isolated from spoiled butter. The plants were collected in the region Azzemour of South West Morocco and the EOs, extracted by hydrodistillation, were analyzed by GC-MS. The antimicrobial activity was determined using the agar paper disc method. The main components of A. herba-alba EO were cis-thujone, trans-thujone and vanillyl alcohol; in O. majorana EO terpinen-4-ol, isopulegol and β-phellandrene predominated. Both essential oils exhibited growth inhibiting activities in a concentration-dependent manner on several microorganism species. Our results demonstrated that O. majorana and A. herba-alba EOs could be effective natural antibacterial agents in foods.

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Section: Discussionmentioning

confidence: 99%

Chemical Composition and Antimicrobial Activity of Artemisia herba-alba and Origanum majorana Essential Oils from Morocco

et al. 2019

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“…Natalia et al [ 23 ] and Park et al [ 24 ] synthesized enzymatically fatty acid vanillyl esters with menhaden and castor oils, respectively. The DPPH radical scavenging activity of the tested compounds strongly depends on the solvent used in the test.…”

Section: Resultsmentioning

confidence: 99%

Enzymatic Synthesis of Lipophilic Esters of Phenolic Compounds, Evaluation of Their Antioxidant Activity and Effect on the Oxidative Stability of Selected Oils

et al. 2021

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The aim of the study was to compare the effect of the substituent and its position in the aromatic ring on the antioxidant activity of hexanoic acid esters obtained in reactions catalyzed by immobilized lipase B from Candida antarctica. 4-Hydroxybenzyl hexanoate, 2-hydroxybenzyl hexanoate, 4-methoxybenzyl hexanoate, and vanillyl hexanoate were obtained with conversion yields of 50 to 80%. The antioxidant activity of synthesized esters, their alcohol precursors and BHT (Butylated HydroxyToluene) was compared with DPPH (2,2-diphenyl-1-picrylhydrazyl), CUPRAC (cupric ion reducing antioxidant capacity), and CBA (crocin bleaching assay) methods. Furthermore, it was investigated whether the presence of vanillyl hexanoate in a concentration of 0.01 and 0.1% affected the oxidative stability of sunflower and rapeseed oils in the Rancimat test. It was observed that the antioxidant activity of hexanoic acid esters depends on the presence and position of the hydroxyl group in the aromatic ring. The highest activities were found for vanillyl alcohol, vanillyl hexanoate, and BHT. The addition of the ester and BHT significantly extended the induction times of the tested oils, and these compounds exhibited similar activity. Vanillyl hexanoate increased the induction time from 4.49 to 5.28 h and from 2.73 to 3.12 h in the case of rapeseed and sunflower oils, respectively.

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“…2e). By comparison with other chromatograms from the previous literature, new peaks produced by enzyme reactions were annotated as HPA-DON and HPA-dFO, respectively [17]. These reaction products were collected using Prep-LC system as shown in Fig.…”

Section: Hplc Analysis Of the Reaction Products And Purification Of Hmentioning

confidence: 99%

“…Therefore, HPA-dFO showed quite stronger antioxidant activity than HPA-DON and HPA in methanol system. It is known that the DPPH radical scavenging activity of a compound depends on the type of solvent [17]. To elucidate the relationship between the radical scavenging activity of HPA, HPA-DON, and HPA-dFO and the hydrophobic properties of solvents, DPPH assays were also performed in non-polar solvents.…”

Section: Evaluation Of Dpph Radical Scavenging Activitymentioning

confidence: 99%

“…Nowadays, one method to prevent or delay auto oxidation in food containing PUFAs is to add antioxidant compound, such as phenolic acid, as an additive, to improve the stabilization of PUFAs [14]. Enzymatic transesterification of phenolic acid with triglyceride or fatty alcohol is gaining interest to increase their solubilization and antioxidant properties in hydrophobic media for extensive industrial application [15][16][17][18][19]. Conjugating phenolic compounds with triglyceride can be performed chemically or enzymatically.…”

Section: Introductionmentioning

confidence: 99%

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Evaluation of antioxidant and antimicrobial activity of phenolic lipids produced by the transesterification of 4-hydroxyphenylacetic acid and triglycerides

et al. 2019

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Several phenolic compounds derived from plant biomass are attracting attention because they display high antioxidant activity. In this study, antioxidant activity was confirmed in 4-hydroxyphenylacetic acid (HPA), and transesterification reaction using Candida antarctica lipase B was performed to enhance the solubility of HPA. The HPA-diolein (HPA-DON) was synthesized from HPA and triolein, while the HPA-fish oil diglyceride (HPA-dFO) was synthesized from HPA and Menhaden fish oil. To increase the conversion yield, the enzyme reaction conditions of the substrate molar ratio, enzyme amount, and reaction time were optimized. After the reaction, HPA-DON and HPA-dFO were purely separated, using prep-LC. The activity assays using DPPH and ABTS radicals confirmed that HPA-DON and HPA-dFO have antioxidant activity. HPA-DON has high activity in non-polar solvents, while HPA-dFO has strong activity in both polar solvents and non-polar solvents. In addition, HPA-dFO has the growth inhibition activity for Bacillus coagulans, Geobacillus stearothermophilus, and Alcaligenes faecalis that cause food spoilage. Therefore, HPA-dFO is a new synthetic substance that has both antioxidant activity and antibacterial activity. The results indicate that these HPA-derivatives can be expected to be developed as important materials in the food and cosmetics industries.

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Antioxidant and antibacterial activity of fatty acid vanillyl ester produced by Proteus vulgaris K80 lipase-mediated transesterification

Cited by 15 publications

References 30 publications

Chemical Composition and Antimicrobial Activity of Artemisia herba-alba and Origanum majorana Essential Oils from Morocco

Chemical Composition and Antimicrobial Activity of Artemisia herba-alba and Origanum majorana Essential Oils from Morocco

Enzymatic Synthesis of Lipophilic Esters of Phenolic Compounds, Evaluation of Their Antioxidant Activity and Effect on the Oxidative Stability of Selected Oils

Evaluation of antioxidant and antimicrobial activity of phenolic lipids produced by the transesterification of 4-hydroxyphenylacetic acid and triglycerides

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