Enzymatic alkylsuccinylation of tyrosol: Synthesis, characterization and property evaluation as a dual-functional antioxidant

Marzocchi, Silvia; Anankanbil, Sampson; Caboni, Maria Fiorenza; Guo, Zheng

doi:10.1016/j.foodchem.2017.10.142

Cited by 16 publications

(10 citation statements)

References 33 publications

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“…On the other hand, tyrosol, a biophenol with notable anti-oxidant potential [ 95 ], was utilized for the formation of alkyl-succinylatedtyrosol synthetic amphiphilic lipids (catalyzed by lipase succinylation of tyrosol with different alkyl chain lengths of alkyl succinic anhydrides) [ 96 ]. According to the characterization profile of tyrosol-based-derived synthetic lipids, all four derivatives exhibited surface active and anti-oxidant abilities to a variable extent.…”

Section: Anti-oxidant Propertiesmentioning

confidence: 99%

Surface Active Agents and Their Health-Promoting Properties: Molecules of Multifunctional Significance

et al. 2020

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Surface active agents (SAAs) are molecules with the capacity to adsorb to solid surfaces and/or fluid interfaces, a property that allows them to act as multifunctional ingredients (e.g., wetting and dispersion agents, emulsifiers, foaming and anti-foaming agents, lubricants, etc.) in a widerange of the consumer products of various industrial sectors (e.g., pharmaceuticals, cosmetics, personal care, detergents, food, etc.). Given their widespread utilization, there is a continuously growing interest to explore their role in consumer products (relevant to promoting human health) and how such information can be utilized in order to synthesize better chemical derivatives. In this review article, weaimed to provide updated information on synthetic and biological (biosurfactants) SAAs and their health-promoting properties (e.g., anti-microbial, anti-oxidant, anti-viral, anti-inflammatory, anti-cancer and anti-aging) in an attempt to better define some of the underlying mechanism(s) by which they exert such properties.

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Section: Anti-oxidant Propertiesmentioning

confidence: 99%

Surface Active Agents and Their Health-Promoting Properties: Molecules of Multifunctional Significance

et al. 2020

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“…On the basis of our previous work in our lab, anhydrides can be used as excellent electrophiles, which can react with a series of nucleophiles, such as MAGs, polysaccharides, sugar alcohols, and phenolic acid. ,,,, Accordingly, we were inspired to synthesize the aspartic-acid-based amphiphiles using N-protected aspartic anhydride as the acyl donor and MAGs/hexadecanol as nucleophiles in the absence of a catalyst (Figure ). With the solubility of reactants and less toxicity taken into account, the reactions were carried out in ACN at 50–80 °C depending upon the different carbon chains of MAG (50 °C for compounds 1 – 3 , 70 °C for compound 4 , and 80 °C for compounds 5a , 5b , and 6 ).…”

Section: Resultsmentioning

confidence: 99%

“…From Table 2, the results of CMC and γ cmc values showed that CMC values decreased from 0.75 to 0.02 mM with the increase of hydrophobic carbon chains of all synthetic compounds, which was similar to what has been reported in previous works. 26,39,40 Conversely, the γ cmc values increased from 20.0 to 49.4 mN/m as the alkyl chains of compounds increased, which might be explained by the corresponding decrease in area per molecule at CMC (113.6−35.8 Å 2 ). In addition, the γ values of the compounds at the same concentration of 0.1 mM (γ 0.1 ) were also determined.…”

Section: ■ Materials and Methodsmentioning

confidence: 97%

“…O/W emulsions were formulated to evaluate the oil/water interfacial properties of the synthesized compounds with commercial DATEM as a control as described in the previous reports from our lab. , In brief, the aqueous phase containing 2.0% (w/w) synthetic compounds was first prepared with a pH adjustment to 1.0, 5.0, 7.0, and 9.0, separately, using 0.1 M NaOH or HCl solution. Subsequently, 2 mL of fish oil was mixed with 8 mL of aqueous phase prepared above, followed by magnetic stirring for 15 min.…”

Section: Methodsmentioning

confidence: 99%

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Aspartic-Acid-Based Ampholytic Amphiphiles: Synthesis, Characterization, and pH-Dependent Properties at Air/Water and Oil/Water Interfaces

Cheng

Anankanbil

Pérez

et al. 2019

J. Agric. Food Chem.

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A facile and two-step strategy was employed to synthesize a series of novel aspartic-acid-based ampholytic amphiphiles from sustainable and commercially viable substances as starting materials. The molecular structures of the synthetic compounds were well-identified by mass spectrometry and 1 H/ 13 C nuclear magnetic resonance analysis, and the physicochemical, pH-dependent foaming, and emulsifying properties were evaluated by the use of multiple techniques, such as Fourier transform infrared spectroscopy, differential scanning calorimetry, Langmuir−Blodgett study, and fluorescence microscopy imaging. As a result of the co-existence of amino and carboxyl groups in the synthetic compounds, the compounds presented varying charges (cationic, ampholytic, and anionic) depending upon the pH of the medium compared to the dissociation constants (pK a ). Compounds with cationic (pH 1.0) and anionic (pH 9.0) forms had significantly higher γ 0.1 and critical micelle concentration values than those with ampholytic forms (pH 7.0). sn-1-Lauroyl-sn-3-aspartic acid (compound 3) at neutral and alkaline conditions displayed comparable foaming properties, including foaming, calcium-tolerant, and temperature-resistant abilities, with commercial sulfonate sodium dodecyl sulfate (SDS), and thus might be a promising alternative to SDS, applied in personal care products and detergent formula. sn-1-Palmtoyl-sn-3-aspartic acid (compound 5a) with an ampholytic structure was proven as the most excellent stabilizer for the preparation of oil-in-water emulsions compared to palmityl aspartic acid (compound 5b), commercial food ingredient diacetyltartaric acid esters of mono-and diglycerides, and glyceride monopalmitate at aqueous phase pH 7.0. Thus, it has promising use as a pH-dependent emulsifying agent in various fields.

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“…Emulsions are thermodynamically unstable systems made of small droplets of one liquid dispersed in another immiscible liquid whose stabilization is achieved by incorporating emulsifiers that adsorb at the interface of the two immiscible fluids. Many of the industrial surfactants are of synthetic origin, but more natural biobased alternatives are increasingly sought after [ 31 , 32 , 33 ] including in the form of biomass-based particles [ 34 , 35 ]. When used as emulsifiers, extracts are mostly obtained by water extraction in order to recover amphiphilic macromolecules such as proteins and polysaccharides [ 36 , 37 , 38 , 39 , 40 ], though polysaccharides such as saponins can be extracted by ethanol:water mixtures as well [ 41 ].…”

Section: Introductionmentioning

confidence: 99%

Impact of Hydro-Alcoholic Solvents on the Oil and Phenolics Extraction from Walnut (Juglans regia L.) Press-Cake and the Self-Emulsification of Extracts

Garcia-Mendoza

Savoire

Harscoat–Schiavo

2022

Foods

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The objective was to evaluate the performance of four hydro-alcoholic solvents to simultaneously extract oil and more polar molecules as phenolics, among others, to produce complex extracts that eventually could self-emulsify after solvent removal. Walnut press-cake was selected as the sourcing material. Extractions were performed as a semi-continuous operation up to a solvent-to-solid ratio of 28, with a fractional collection of the effluent. Among the solvents, labelled by their alcohol content EtOH 58, EtOH 86, iPro 60 and iPro 90 for ethanol (EtOH) and isopropanol (iPro), iPro 90 allowed to reach an oil extraction efficiency of 97% while the recovery for the other solvents was in the range of 30–40%. For both alcohols, the increase of the solvent hydration negatively influenced the oil extraction but positively increased the recovery of phenolics that reached 17.6 mg GAE/gcake when EtOH 58 was used. Several fractions contained enough surface-active material and oil to self-assemble as emulsions. IPro 90 and EtOH 86 showed better performances in the sense that most extracts were able to emulsify, though extraction kinetics pointed out differences. The most hydrated solvents behaved equally, with extraction yields in the same range and a similar but limited emulsifying capacity of only few fractions.

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Enzymatic alkylsuccinylation of tyrosol: Synthesis, characterization and property evaluation as a dual-functional antioxidant

Cited by 16 publications

References 33 publications

Surface Active Agents and Their Health-Promoting Properties: Molecules of Multifunctional Significance

Surface Active Agents and Their Health-Promoting Properties: Molecules of Multifunctional Significance

Aspartic-Acid-Based Ampholytic Amphiphiles: Synthesis, Characterization, and pH-Dependent Properties at Air/Water and Oil/Water Interfaces

Impact of Hydro-Alcoholic Solvents on the Oil and Phenolics Extraction from Walnut (Juglans regia L.) Press-Cake and the Self-Emulsification of Extracts

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