Highly Efficient Synthesis of Phytosterol Linolenate Catalyzed by &lt;i&gt;Candida Rugosa&lt;/i&gt; Lipase through Transesterification

He, Wen‐Sen; Cui, Dandan; Zhang, Yilu; Liu, Yu; Ji, Yin; Chen, Gang; Jia, Chengsheng; Feng, Bo

doi:10.3136/fstr.23.525

Cited by 18 publications

(35 citation statements)

References 29 publications

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“…The esterification conversions were also high for most of the studies reviewed (Table 2), some of them reaching more than 95%, which is near to the conversions of chemical reactions. Low reaction times were found in those studies (Table 1), especially with C. rugosa lipase, with which many were lower than 2 h [65,78,84,86,88]. These results showed that the use of enzymes for the synthesis of phytosterol esters is very promising.…”

Section: General Aspectsmentioning

confidence: 92%

“…Phytosterols are insoluble in water, and their solubility in fats and oils is close to 1 g/100 g. To overcome this limitation, esterification of a fatty acid to the single hydroxyl of plant sterols has been studied as an approach to increase lipid solubility and facilitate food formulations [17]. For instance, He et al [65] reported that, by the esterification with linoleic acid, the solubility of phytosterols in oils was improved by 18 times. The esterification of phytosterols not only increases their solubility in oily solutions, but also decreases their melting point and improves flavor and bioavailability [66].…”

Section: Phytosterolsmentioning

confidence: 99%

“…Lipase B from Candida antarctica (CALB), the most used commercial lipase, is also identified in Table 2 in a work performed by Yu et al [76] in 2019, with high conversion values (93.2%). Additionally, He et al [65] compared this enzyme with C. rugosa lipase for the transesterification of phytosterols with ethyl linolenate and obtained a conversion four times lower than for CALB. The esterification conversions were also high for most of the studies reviewed (Table 2), some of them reaching more than 95%, which is near to the conversions of chemical reactions.…”

Section: General Aspectsmentioning

confidence: 99%

“…Probably the use of a reverse micelle system that combines an aqueous dispersed phase and a nonaqueous continuous phase with the assistance of amphiphilic molecules, was not ideal for a temperature increase since thermostability of free enzymes is usually lower than immobilized systems [73]. He et al [65] studied the effect of temperature on the synthesis of phytosterol linolenate catalyzed by lyophilized C. rugosa lipase and observed that increasing temperature improved the substrate solubility, but the catalytic activity and stability of the enzyme were strongly affected. At 50 • C, phytosterol linoleate conversion was more than three times the conversion with immobilized enzymes Novozyme 435 and Lipozyme RM IM, but the optimal temperature for the ester conversion by lyophilized Candida rugosa lipase was 40 • C [65].…”

Section: Effect Of Temperaturementioning

confidence: 99%

“…He et al [65] studied the effect of temperature on the synthesis of phytosterol linolenate catalyzed by lyophilized C. rugosa lipase and observed that increasing temperature improved the substrate solubility, but the catalytic activity and stability of the enzyme were strongly affected. At 50 • C, phytosterol linoleate conversion was more than three times the conversion with immobilized enzymes Novozyme 435 and Lipozyme RM IM, but the optimal temperature for the ester conversion by lyophilized Candida rugosa lipase was 40 • C [65].…”

Section: Effect Of Temperaturementioning

confidence: 99%

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Lipases as Effective Green Biocatalysts for Phytosterol Esters’ Production: A Review

et al. 2022

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Lipases are versatile enzymes widely used in the pharmaceutical, cosmetic, and food industries. They are green biocatalysts with a high potential for industrial use compared to traditional chemical methods. In recent years, lipases have been used to synthesize a wide variety of molecules of industrial interest, and extraordinary results have been reported. In this sense, this review describes the important role of lipases in the synthesis of phytosterol esters, which have attracted the scientific community’s attention due to their beneficial effects on health. A systematic search for articles and patents published in the last 20 years with the terms “phytosterol AND esters AND lipase” was carried out using the Scopus, Web of Science, Scielo, and Google Scholar databases, and the results showed that Candida rugosa lipases are the most relevant biocatalysts for the production of phytosterol esters, being used in more than 50% of the studies. The optimal temperature and time for the enzymatic synthesis of phytosterol esters mainly ranged from 30 to 101 °C and from 1 to 72 h. The esterification yield was greater than 90% for most analyzed studies. Therefore, this manuscript presents the new technological approaches and the gaps that need to be filled by future studies so that the enzymatic synthesis of phytosterol esters is widely developed.

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Section: General Aspectsmentioning

confidence: 92%

Section: Phytosterolsmentioning

confidence: 99%

Section: General Aspectsmentioning

confidence: 99%

Section: Effect Of Temperaturementioning

confidence: 99%

Section: Effect Of Temperaturementioning

confidence: 99%

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Lipases as Effective Green Biocatalysts for Phytosterol Esters’ Production: A Review

et al. 2022

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Enhanced antioxidant capacity of lipoic acid in different food systems through lipase‐mediated esterification with phytosterols

Sun

et al. 2022

J Sci Food Agric

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BACKGROUND α‐Lipoic acid has excellent antioxidant activity, but its poor lipid solubility greatly limits its practical application. This study was undertaken (i) to develop a novel and efficient enzymatic synthesis of lipophilic lipoic acid esters using Candida sp. 99‐125 lipase as a catalyst; and (ii) to systematically evaluate their antioxidant potential against bulk oil, oil‐in‐water emulsion (O/W) and cooked ground meat. RESULTS Lipophilic lipoic acid esters were successfully and efficiently synthesized using phytosterols as acyl receptor in the presence of Candida sp. 99‐125 lipase. The product was identified as phytosterol lipoate by mass spectrometry, Fourier transform infrared spectroscopy and nuclear magnetic resonance. The maximum conversion of phytosterol lipoate surpassed 90% within 12 h and its final yield exceeded 81%. Interestingly, the oil solubility of lipoic acid was increased at least 25‐fold and other physicochemical properties were significantly improved. Most importantly, phytosterol lipoate exhibited higher antioxidant activity than lipoic acid in bulk oil, O/W emulsions and cooked ground meat. CONCLUSION The antioxidant capacity of lipoic acid can be significantly enhanced by esterification with phytosterols. Therefore, phytosterol lipoate could be further developed as a new antioxidant for use in oil‐ and fat‐based foods. © 2022 Society of Chemical Industry.

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Improved antioxidant activity of rutin via lipase‐mediated esterification with oleic acid

et al. 2023

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BACKGROUND: Oxidation is a major problem for oils and fats, which can be mitigated by antioxidants. Rutin has excellent antioxidant activity, but its poor lipid solubility greatly limits its practical application. In this study, an efficient enzymatic synthesis route of lipophilic rutin ester was established using oleic acid as an acyl donor, and the antioxidant potential of rutin oleate was evaluated for the first time by proton ( 1 H) nuclear magnetic resonance (NMR) spectroscopy. RESULTS:The synthesized product was finally identified as rutin oleate by Fourier transform infrared, high-performance liquid chromatography-mass spectrometry, and 1 H, carbon-13, and DEPT-135 NMR analyses, and the acylation site was the 4 000 -OH of the rhamnose group in the rutin molecule. The maximum conversion was over 93% after 48 h of reaction using Novozym 435 as catalyst under the best conditions among these tests. The conversion of rutin ester decreased with the increase of carbon chain length and the number of carbon-carbon double bonds of the fatty acid molecule. Most importantly, rutin oleate exhibited antioxidant capacity comparable to butylated hydroxytoluene and its counterparts (rutin and oleic acid) at low temperatures (60°C), but had a significant advantage at high temperatures (120°C).CONCLUSION: The antioxidant activity of rutin was significantly enhanced by lipase-mediated esterification with oleic acid. Therefore, rutin oleate could be further developed as a novel antioxidant for use in oil-and fat-based foods.

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Highly Efficient Synthesis of Phytosterol Linolenate Catalyzed by <i>Candida Rugosa</i> Lipase through Transesterification

Cited by 18 publications

References 29 publications

Lipases as Effective Green Biocatalysts for Phytosterol Esters’ Production: A Review

Lipases as Effective Green Biocatalysts for Phytosterol Esters’ Production: A Review

Enhanced antioxidant capacity of lipoic acid in different food systems through lipase‐mediated esterification with phytosterols

Improved antioxidant activity of rutin via lipase‐mediated esterification with oleic acid

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