Synthesis of lutein esters using a novel biocatalyst of <i>Candida antarctica</i> lipase B covalently immobilized on functionalized graphitic carbon nitride nanosheets

Shangguan, Huijuan; Zhang, Shan; Li, Xin; Zhou, Qi; Shi, Jie; Deng, Qianchun; Huang, Fenghong

doi:10.1039/d0ra00563k

Cited by 12 publications

(14 citation statements)

References 34 publications

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“…After 24 h, the yields dropped below 10%, which clearly indicated the sensitivity of the compounds toward prolonged exposures to increased temperatures. At 40 °C and at ambient temperature, the reaction rates were lower, but yields remained stable and quantitative even after 24 h. In other studies, reactions were most often carried out at ambient temperatures (20–25 °C) or at 40 °C. ,,,,,, In some instances, higher temperatures were also used (50–90 °C), but surprisingly, no diester product degradation was reported. − ,, We show that ambient temperature is the most energy-efficient option which ensures good yields with concomitant product stability.…”

Section: Resultsmentioning

confidence: 71%

“…It is not uncommon to use a large excess of an esterifying agent (up to 25 equiv) to drive the conversion of xanthophylls to their corresponding esters to (near) completion. ,,− However, by doing so, large amounts of waste are created. In our study, a total conversion of lutein (0.3 mM in EtOAc) into its diacetate was observed after 6 h when lutein/acetic anhydride/DMAP were reacted in a molar ratio of 1:15:30 (7.5 equiv of anhydride for each of the two lutein OH groups); large excess of DMAP was necessary to avoid isomerization and degradation.…”

Section: Resultsmentioning

confidence: 99%

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Utilization of Plant-Based Wastes for a Sustainable Preparation of Xanthophyll Esters via Acid Anhydrides Using β-Pinene as a Bio-Derived Solvent

Metličar

Kranjc

Albreht

2021

ACS Sustainable Chem. Eng.

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A new valorization strategy for selected plant-based waste materials has been put forward. We have shown that avocado peels (fruit waste) and green leaves of Japanese knotweed (plant waste) are good sources of free xanthophylls such as antheraxanthin (9 mg/100 g dry weight) and lutein (106 mg/100 g dry weight), respectively, which can be converted into xanthophyll esters, a process inspired by nature to regulate the physicochemical properties of these bioactive species such as solubility and chemical stability. To this end, we developed the first environmentally friendly and economically viable synthetic platform and critically evaluated it by preparing 55 different xanthophyll esters (combining 5 model xanthophylls with 11 structurally and electronically distinct acid anhydrides). These esters were synthesized using β-pinene as a bio-derived solvent at ambient temperature and pressure with excellent selectivity (median 97%) and finally isolated in high yields (median 81%) and with high purities (median 97%). The integration of this technology with xanthophyll-containing wastes contributes to the zero-waste principle, and new valorization pathways for invasive alien plant species (such as Japanese knotweed) are particularly welcome as they help to control their rapid spread which causes great economic damage and loss of biodiversity around the globe.

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Section: Resultsmentioning

confidence: 71%

Section: Resultsmentioning

confidence: 99%

Utilization of Plant-Based Wastes for a Sustainable Preparation of Xanthophyll Esters via Acid Anhydrides Using β-Pinene as a Bio-Derived Solvent

Metličar

Kranjc

Albreht

2021

ACS Sustainable Chem. Eng.

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“…The droplets numbered 3 and 13 contain no encapsulated n-dodecane droplet use in biocatalytic transformations. CalB shows conformational stability and thus enzymatic activity even in non-polar solvents as for example cyclohexane [54]), toluene ( [55], isooctane [56], methyl-tert-butyl ether (MTBE) [57], and dimethyl formamide (DMF) [58]. In contrast to other lipases, CalB does not show a phenomenon known as interfacial activation due to the absence of a lid, which covers the active site entrance in other lipases [59].…”

Section: Lipase-catalyzed Ester Hydrolysis Inside Double-emulsion Dro...mentioning

confidence: 99%

Analysis of double-emulsion droplets with ESI mass spectrometry for monitoring lipase-catalyzed ester hydrolysis at nanoliter scale

et al. 2022

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Microfluidic double-emulsion droplets allow the realization and study of biphasic chemical processes such as chemical reactions or extractions on the nanoliter scale. Double emulsions of the rare type (o1/w/o2) are used here to realize a lipase-catalyzed reaction in the non-polar phase. The surrounding aqueous phase induces the transfer of the hydrophilic product from the core oil phase, allowing on-the-fly MS analysis in single double droplets. A microfluidic two-step emulsification process is developed to generate the (o1/w/o2) double-emulsion droplets. In this first example of microfluidic double-emulsion MS coupling, we show in proof-of-concept experiments that the chemical composition of the water layer can be read online using ESI–MS. Double-emulsion droplets were further employed as two-phase micro-reactors for the hydrolysis of the lipophilic ester p-nitrophenyl palmitate catalyzed by the Candida antarctica lipase B (CalB). Finally, the formation of the hydrophilic reaction product p-nitrophenol within the double-emulsion droplet micro-reactors is verified by subjecting the double-emulsion droplets to online ESI–MS analysis. Graphical abstract

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“…Table 4 shows the stabilizing capacity of different matrices of lutein and zeaxanthin esters. In this respect, Shangguan et al [134] described the synthesis of lutein esters utilizing a new covalently immobilized lipase B from Candida antarctica onto functionalized graphitic carbon nitride nanosheets. Gombač et al [135] used viable and accessible procedures to create stable firm encapsulates of lutein and its esters.…”

Section: Esterification Of Lutein and Zeaxanthin To Enhance The Stability And Bioavailability In Harsh Environmental Conditionsmentioning

confidence: 99%

Biochemical and Immunological implications of Lutein and Zeaxanthin

Zafar

Aqeel

Shah

et al. 2021

IJMS

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Throughout history, nature has been acknowledged for being a primordial source of various bioactive molecules in which human macular carotenoids are gaining significant attention. Among 750 natural carotenoids, lutein, zeaxanthin and their oxidative metabolites are selectively accumulated in the macular region of living beings. Due to their vast applications in food, feed, pharmaceutical and nutraceuticals industries, the global market of lutein and zeaxanthin is continuously expanding but chemical synthesis, extraction and purification of these compounds from their natural repertoire e.g., plants, is somewhat costly and technically challenging. In this regard microbial as well as microalgal carotenoids are considered as an attractive alternative to aforementioned challenges. Through the techniques of genetic engineering and gene-editing tools like CRISPR/Cas9, the overproduction of lutein and zeaxanthin in microorganisms can be achieved but the commercial scale applications of such procedures needs to be done. Moreover, these carotenoids are highly unstable and susceptible to thermal and oxidative degradation. Therefore, esterification of these xanthophylls and microencapsulation with appropriate wall materials can increase their shelf-life and enhance their application in food industry. With their potent antioxidant activities, these carotenoids are emerging as molecules of vital importance in chronic degenerative, malignancies and antiviral diseases. Therefore, more research needs to be done to further expand the applications of lutein and zeaxanthin.

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Synthesis of lutein esters using a novel biocatalyst of Candida antarctica lipase B covalently immobilized on functionalized graphitic carbon nitride nanosheets

Abstract: The functionalized graphitic carbon nitride nanosheets (g-C3N4-Ns) as the immobilized carrier for the accommodation of Candida antarctica lipase B (CALB), which obtains the highest esterification rate (92%) in lutein esters synthesis.

Cited by 12 publications

References 34 publications

Utilization of Plant-Based Wastes for a Sustainable Preparation of Xanthophyll Esters via Acid Anhydrides Using β-Pinene as a Bio-Derived Solvent

Utilization of Plant-Based Wastes for a Sustainable Preparation of Xanthophyll Esters via Acid Anhydrides Using β-Pinene as a Bio-Derived Solvent

Analysis of double-emulsion droplets with ESI mass spectrometry for monitoring lipase-catalyzed ester hydrolysis at nanoliter scale

Biochemical and Immunological implications of Lutein and Zeaxanthin

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