Green Synthesized Magnetic Nanoparticles as Effective Nanosupport for the Immobilization of Lipase: Application for the Synthesis of Lipophenols

Abstract

In this work, hybrid zinc oxide–iron oxide (ZnOFe) magnetic nanoparticles were synthesized employing Olea europaea leaf aqueous extract as a reducing/chelating and capping medium. The resulting magnetic nanoparticles were characterized by basic spectroscopic and microscopic techniques, namely, X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), fourier-transform infrared (FTIR) and atomic force microscopy (AFM), exhibiting a spherical shape, average size of 15–17 nm, and a functionalized surface. Lipase from Thermomyces lanuginosus (TLL) was efficiently immobilized on the surface of ZnOFe nanoparticles through physical absorption. The activity of immobilized lipase was found to directly depend on the enzyme to support the mass ratio, and also demonstrated improved pH and temperature activity range compared to free lipase. Furthermore, the novel magnetic nanobiocatalyst (ZnOFe-TLL) was applied to the preparation of hydroxytyrosyl fatty acid esters, including derivatives with omega-3 fatty acids, in non-aqueous media. Conversion yields up to 90% were observed in non-polar solvents, including hydrophobic ionic liquids. Different factors affecting the biocatalyst performance were studied. ZnOFe-TLL was reutilized for eight subsequent cycles, exhibiting 90% remaining esterification activity (720 h of total operation at 50 °C). The green synthesized magnetic nanoparticles, reported here for the first time, are excellent candidates as nanosupports for the immobilization of enzymes with industrial interest, giving rise to nanobiocatalysts with elevated features.

Fatty Acid Hydroxytyrosyl Esters of Olive Oils Are Bioaccessible According to Simulated In Vitro Gastrointestinal Digestion: Unraveling the Role of Digestive Enzymes on Their Stability

“…39 These reactions have been reported as being closely dependent on the acyl chain length and the degree of unsaturation of FAs that affect the conversion yield of the esterification process due to differences in their spatial configuration. 44,45 In the current work, the generation of HT esters with an equivalent carbon alkyl chain (C18) but with different degrees of unsaturation, C18:1, C18:2, and C18:3 corresponding to HT esterified with OA, LA, and ALA, respectively, was monitored, for the first time, after the intestinal digestion of EVOO with individual and combined intestinal enzymes (pancreatin and pancreatic lipase). The conversion yield of HT-FAs was more pronounced when the reaction was catalyzed only by pancreatin than when pancreatic lipase was HT-ALA: hydroxytyrosol esterified with α-linolenic acid; HT-LA: hydroxytyrosol esterified with linoleic acid; and HT-OA: hydroxytyrosol esterified with oleic acid.…”

“…The study reported that the conversion yields (%) for OA (C18:1), LA (C18:2), and myristic acid (C14:0) were 55.0, 50.4, and 64.3%, respectively, establishing that the number of double bonds had a direct correlation with the molecular structure of the FA, which, as a result, would affect the advance of the acylation reactions. 45 On the contrary, additional studies working with the pure standard of long-chain unsaturated FAs indicated that there was no relationship between chain length and conversion, as the highest conversion was obtained with eicosapentaenoic acid (EPA) (68.0%) relative to OA (46.0%). The variation in these findings may be caused by the selectivity of lipase for the FAs, with the degree of unsaturation being a more relevant factor rather than FA chain length.…”

“…Up to now, the biosynthesis of HT-FAs has been done using commercial enzymes on pure standard compounds . These reactions have been reported as being closely dependent on the acyl chain length and the degree of unsaturation of FAs that affect the conversion yield of the esterification process due to differences in their spatial configuration. , …”

“…This is in agreement with recent research, which utilized nanoparticles with immobilized lipase from Thermomyces lanuginosus and employed olive leaf aqueous extract for the synthesis of bioactive hydroxytyrosyl FA esters. The study reported that the conversion yields (%) for OA (C18:1), LA (C18:2), and myristic acid (C14:0) were 55.0, 50.4, and 64.3%, respectively, establishing that the number of double bonds had a direct correlation with the molecular structure of the FA, which, as a result, would affect the advance of the acylation reactions . On the contrary, additional studies working with the pure standard of long-chain unsaturated FAs indicated that there was no relationship between chain length and conversion, as the highest conversion was obtained with eicosapentaenoic acid (EPA) (68.0%) relative to OA (46.0%).…”

Polyphenols and Fish Oils for Improving Metabolic Health: A Revision of the Recent Evidence for Their Combined Nutraceutical Effects

“…As a consequence, the interest in the so-called omega-3 lipophenol derivatives or phenolipids has grown during the last decade. It has been described a heterogeneous group of different chemical structures obtained from the chemical bonding between polyphenols and omega-3 PUFAs and some from natural sources [ 94 , 95 , 96 ]. There are also esterified phenols with fatty acids different from omega-3 PUFAs, such as caprylic acid [ 97 ], palmitoyl acid [ 98 ], or oleic acid [ 99 ], mainly investigated because of their protective effect in lipid-based food matrices from oxidation, and more recently as functional food ingredients [ 100 ].…”