Novel Approach for Flavonoid Esters Production: Statistically Optimized Enzymatic Synthesis Using Natural Oils and Application in Cosmetics

Milivojević, Ana; Ćorović, Marija; Simović, Milica; Banjanac, Katarina; Blagojević, Stevan; Pjanović, Rada; Bezbradica, Dejan

doi:10.1021/acs.iecr.8b06113

Cited by 15 publications

(15 citation statements)

References 31 publications

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“…Substrate concentration is an important factor in an enzymatic reaction [ 14 , 20 , 21 , 22 , 25 ]; therefore, we conducted experiments by altering the molar ratio of the reactants. We altered the molar ratio of naringin and the acyl donor (1:1, 1:3, 1:5, 1:7, 1:9, and 1:11) and determined its effect on the conversion of naringin acetate ( Figure 5 a).…”

Section: Resultsmentioning

confidence: 99%

“…As transesterification using lipase is a reversible reaction, an excessive acyl donor concentration is required for the reaction equilibrium to shift to transesterification [ 25 , 56 ]. The mechanism of transesterification of the acyl donor and naringin through lipase is as follows.…”

Section: Resultsmentioning

confidence: 99%

“…Meanwhile, in transesterification synthesis, the reaction is conducted using either a high molar ratio of the reactants or a large amount of enzyme. A previous study reported the synthesis and statistical optimization of flavonoid acylation using esculin and linseed oil [ 25 ], the results of which showed that a conversion of 78.5% could be obtained after 96 h of reaction time. In the case of naringin acetate, a study reported a conversion of 41.03% after 96 h of reaction between naringin and vinyl acetate [ 10 ].…”

Section: Introductionmentioning

confidence: 99%

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Efficient Production of Naringin Acetate with Different Acyl Donors via Enzymatic Transesterification by Lipases

Baek

Lee

Son

et al. 2022

IJERPH

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Naringin, one of the citrus flavonoids and known as a natural antioxidant, has limited bioavailability owing to its low stability and solubility. However, naringin esters formed via acylation have recently been reported to possess improved physical and chemical properties. The development of these compounds has a great potential in the food, cosmetic and pharmaceutical industries, but low conversion and productivity are barriers to industrial applications. This study aimed to improve the conversion of naringin acetate, which is formed via the enzymatic reaction between naringin and an acyl donor. An optimal reaction condition was determined by evaluating the effect of various variables (enzyme type, enzyme concentration, acyl donor, molar ratio of reactants, reaction temperature, and solvent) on the synthesis of naringin acetate. The optimal condition was as follows: 3 g/L of Lipozyme TL IM, molar ratio of 1:5 (naringin:acyl donor), reaction temperature of 40 °C, and acetonitrile as the reaction solvent. Under this condition, the maximum conversion to naringin acetate from acetic anhydride and vinyl acetate was achieved at approximately 98.5% (8 h) and 97.5% (24 h), respectively. Compared to the previously reported values, a high conversion was achieved within a short time, confirming the commercial potential of the process.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Efficient Production of Naringin Acetate with Different Acyl Donors via Enzymatic Transesterification by Lipases

Baek

Lee

Son

et al. 2022

IJERPH

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“…Transepidermal water loss was measured using condensed type closed chamber Aquaflux Biox System Ltd., London, UK and 1 mm Teflon semipermeable membrane as was described in a previous study. [ 22 ] The results were processed according to the surface evaporation–sorption isotherm model, and the results were calculated as the time curve of the evaporation flux (g m −2 h −1 ).…”

Section: Methodsmentioning

confidence: 99%

“…26 as was described in a previous study. [ 22 ] This process involves dissolving 1 g of Zea mays protein in 10 g L −1 of a cosmetic formulation sample. Kjeldahl analysis was used to calculate the amount of protein dissolved by a sample using the Velp Scientifica, Italy, UDK 159 Automatic Kjeldahl Analyzer.…”

Section: Methodsmentioning

confidence: 99%

Evaluation of In Vitro Skin Permeation of Enzymatically Synthesized Phloridzin Acetates from Emulsions and Liposomes Dispersed in Gel

Milivojević

Ćorović

Simović

et al. 2022

Euro J Lipid Sci & Tech

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This work aims to evaluate the effect of cosmetic formulations on the skin permeation of phloridzin acetates, therefore in vitro transdermal delivery of these bioactive compounds across Strat-M membrane is investigated. The formulations tested are gel emulsion, oil in water emulsion (O/W emulsion), gel in oil emulsion, liquid crystal emulsion, and liposomes dispersed in gel. The release of esters from the O/W emulsion is diffusion-controlled (n = 0.5), while release kinetics from gel-based formulations depends on coupled diffusion and polymer relaxations effect (0.5 < n < 1). The highest values of effective diffusion coefficient are obtained after release from O/W emulsion (24.64 × 10 −10 m 2 min −1 for phloridzin acetate and 6.55 × 10 −10 m 2 min −1 for phloridzin diacetate). The lag phase lasting from 1 h (gel emulsion) to 5 h (liquid crystal emulsion) indicates that esters permeation is significantly affected by the formulation used. Formulations in which the water is continuous phase are the most appropriate carrier system for transdermal delivery of phloridzin esters. Additionally, liposomes are successfully applied as carrier systems for the controlled release of esters, although it should be noted that liposomes without cholesterol show remarkable stability (𝜻 = −43 mV) and homogeneity (polydispersity index = 0.198). Practical application: Phloridzin is a flavonoid glycoside that possesses many beneficial activities such as antioxidant, UV-protecting, and anti-inflammatory activity, so the use of this flavonoid and its derivatives in numerous cosmetic and pharmaceutical formulations seems very attractive. Results obtained in this study give a comprehensive insight into the release mechanism of phloridzin acetates from emulsions and liposomes, enable the selection of optimum cosmetic formulations depending on the application, and provide significant scientific contribution in the field of topical administration of bioactive flavonoid derivatives.

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Improvement of the oxidative stability of edible oils through enzymatic esterification with hydroxytyrosol‐rich extract

Fotiadou,

Vougiouklaki,

Houhoula

et al. 2024

Euro J Lipid Sci & Tech

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Oxidative degradation is a common issue of commercial edible oils that results in rancidity, downgrading the organoleptic characteristics of food matrices. The aim of this study was the enzymatic modification of common vegetable oils (pomace olive and sunflower oil) with polyphenolic extract to prepare functional oils enriched with bioactive phenolipids. Under that scope, an agro‐industrial effluent, olive mill wastewater, was used as source to recover phenolic compounds. The recovery of hydroxytyrosol and tyrosol reached up to 81.2% ± 0.3% and 98.3% ± 0.2%, respectively. Further, immobilized lipase was used to catalyze the one‐step acylation of these phenolic antioxidants into the oils with the aim of enhancing their stability under accelerated oxidation conditions. The optimum parameters of the bioconversion were found to be 0.1% (w/w) immobilized lipase, 24h of incubation at 50°C under orbital shaking reaching high conversion yields for both phenolic compounds (≥94%). The results also highlighted that the extract‐modified oils presented notable thermooxidative stability at 60°C for 28 days compared to the control and synthetic antioxidant‐enriched oils, as demonstrated by several analytical (conjugated dienes, thiobarbituric reactive substances), chromatographic (solid‐phase microextraction gas chromatography/mass spectroscopy), and spectroscopic (fluorescence, attenuated total reflectance) techniques, giving new insights regarding the preservation of edible oils.Practical Application: Htyr has recently gained much attention as an active ingredient of food matrices for industrial applications due to its high antioxidant/antiradical activity. A major drawback of Htyr exploitation is the high market price and its solubility. Meanwhile, several edible oils are prone to autooxidation during transport, stock management, and household storage. The proposed one‐step biocatalytic process aims to enhance the lipophilicity and bioactivity of Htyr in bulk oil systems, making the use of this potent antioxidant compound feasible. This approach shows promise in extending the shelf life of common oils and highlights the advantages of by‐product management. Moreover, these functional oils can be applied for the preparation of sauces, bakery products, food supplements, and so on, as the bioactive ingredients that are present in them can delay the oxidative cascade reactions and, thus, the spoilage of the products, whereas the whole process meets the requirements of circular economy and green chemistry.

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Novel Approach for Flavonoid Esters Production: Statistically Optimized Enzymatic Synthesis Using Natural Oils and Application in Cosmetics

Cited by 15 publications

References 31 publications

Efficient Production of Naringin Acetate with Different Acyl Donors via Enzymatic Transesterification by Lipases

Efficient Production of Naringin Acetate with Different Acyl Donors via Enzymatic Transesterification by Lipases

Evaluation of In Vitro Skin Permeation of Enzymatically Synthesized Phloridzin Acetates from Emulsions and Liposomes Dispersed in Gel

Improvement of the oxidative stability of edible oils through enzymatic esterification with hydroxytyrosol‐rich extract

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