Candida sp. 99-125 lipase-catalyzed synthesis of ergosterol linolenate and its characterization

•Ergosterol linolenate was successfully synthesized using Candida sp. 99-125 lipase.•The products were characterized by FT-IR, MS and NMR.•Ergosterol conversion exceeded 92% in 12 h.•The physiochemical properties of ergosterol were greatly improved.•This route showed great potential for large-scale...

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Veröffentlicht in:Food chemistry 2019-05, Vol.280, p.286-293
Hauptverfasser: He, Wen-Sen, Li, Lingling, Zhao, Jia, Xu, Hanshan, Rui, Jiaxin, Cui, Dandan, Li, He, Zhang, Huijuan, Liu, Xinqi
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container_end_page 293
container_issue
container_start_page 286
container_title Food chemistry
container_volume 280
creator He, Wen-Sen
Li, Lingling
Zhao, Jia
Xu, Hanshan
Rui, Jiaxin
Cui, Dandan
Li, He
Zhang, Huijuan
Liu, Xinqi
description •Ergosterol linolenate was successfully synthesized using Candida sp. 99-125 lipase.•The products were characterized by FT-IR, MS and NMR.•Ergosterol conversion exceeded 92% in 12 h.•The physiochemical properties of ergosterol were greatly improved.•This route showed great potential for large-scale production of ergosterol ester. As a major sterol in edible mushroom, ergosterol has gained much attention owing to its potential bioactivities. However, ergosterol has a high melting point, poor oil solubility and stability, which restrict its scope of application. In this study, an ergosterol ester of α-linolenic acid was successfully and efficiently prepared using Candida sp. 99-125 lipase as a biocatalyst. The desired product was confirmed to be ergosterol linolenate using MS, FT-IR, and NMR analyses. Using Candida sp. 99-125 lipase, the product conversion exceeded 92% in 12 h under the following optimized parameters: 75 mmol/L ergosterol, 40 g/L lipase, 1:1.25 ergosterol-to-α-linolenic acid molar ratio, and 45 °C. The results confirmed that Candida sp. 99-125 lipase has good reusability and stability and is also relatively low cost, suggesting its great potential for large-scale production of ergosterol ester. Most importantly, the physiochemical properties (oil solubility and melting point) of ergosterol significantly improved after esterification with α-linolenic acid, thus facilitating its application in oil-based systems.
doi_str_mv 10.1016/j.foodchem.2018.12.076
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As a major sterol in edible mushroom, ergosterol has gained much attention owing to its potential bioactivities. However, ergosterol has a high melting point, poor oil solubility and stability, which restrict its scope of application. In this study, an ergosterol ester of α-linolenic acid was successfully and efficiently prepared using Candida sp. 99-125 lipase as a biocatalyst. The desired product was confirmed to be ergosterol linolenate using MS, FT-IR, and NMR analyses. Using Candida sp. 99-125 lipase, the product conversion exceeded 92% in 12 h under the following optimized parameters: 75 mmol/L ergosterol, 40 g/L lipase, 1:1.25 ergosterol-to-α-linolenic acid molar ratio, and 45 °C. The results confirmed that Candida sp. 99-125 lipase has good reusability and stability and is also relatively low cost, suggesting its great potential for large-scale production of ergosterol ester. 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As a major sterol in edible mushroom, ergosterol has gained much attention owing to its potential bioactivities. However, ergosterol has a high melting point, poor oil solubility and stability, which restrict its scope of application. In this study, an ergosterol ester of α-linolenic acid was successfully and efficiently prepared using Candida sp. 99-125 lipase as a biocatalyst. The desired product was confirmed to be ergosterol linolenate using MS, FT-IR, and NMR analyses. Using Candida sp. 99-125 lipase, the product conversion exceeded 92% in 12 h under the following optimized parameters: 75 mmol/L ergosterol, 40 g/L lipase, 1:1.25 ergosterol-to-α-linolenic acid molar ratio, and 45 °C. The results confirmed that Candida sp. 99-125 lipase has good reusability and stability and is also relatively low cost, suggesting its great potential for large-scale production of ergosterol ester. Most importantly, the physiochemical properties (oil solubility and melting point) of ergosterol significantly improved after esterification with α-linolenic acid, thus facilitating its application in oil-based systems.</description><subject>alpha-Linolenic Acid - chemistry</subject><subject>alpha-Linolenic Acid - metabolism</subject><subject>Biocatalysis</subject><subject>Candida - enzymology</subject><subject>Candida sp. 99-125 lipase</subject><subject>Enzymes, Immobilized - chemistry</subject><subject>Enzymes, Immobilized - metabolism</subject><subject>Ergosterol - chemistry</subject><subject>Ergosterol - metabolism</subject><subject>Ergosterol ester</subject><subject>Esterification</subject><subject>Lipase - chemistry</subject><subject>Lipase - metabolism</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Oil solubility</subject><subject>Oils, Volatile - chemistry</subject><subject>Oils, Volatile - metabolism</subject><subject>Solubility</subject><subject>Temperature</subject><subject>α-Linolenic acid</subject><issn>0308-8146</issn><issn>1873-7072</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkLFu2zAQhomiQe24fQWDYxepPEqkxK2F0SQFDGRJZoImTzUNWXRJuoD99KHhuGunG_7v7sd9hCyB1cBAftvVQwjObnFfcwZ9DbxmnfxA5tB3TdWxjn8kc9awvuqhlTNyn9KOMXZhP5FZw2TLW6XmRK_M5LwzNB1qqlQFXNDRH0zCyppsxtMZHU2nKW8x-UTDQDH-DiljDGMBpzDiZDLScoX6nKjdmmhsif3ZZB-mz-RuMGPCL-9zQV4ffr6snqr18-Ov1Y91ZVsmcgWDs6ZDhU4Z1XRcWObQtEL2nDmnhFUKStYLJdQGG2ikkyA20DujsEfRLMjX691DDH-OmLLe-2RxHM2E4Zg0h041ArhUBZVX1MaQUsRBH6Lfm3jSwPRFrt7pm1x9EaaB6yK3LC7fO46bPbp_azebBfh-BbB8-tdj1Ml6nCw6H9Fm7YL_X8cbwKmPBA</recordid><startdate>20190515</startdate><enddate>20190515</enddate><creator>He, Wen-Sen</creator><creator>Li, Lingling</creator><creator>Zhao, Jia</creator><creator>Xu, Hanshan</creator><creator>Rui, Jiaxin</creator><creator>Cui, Dandan</creator><creator>Li, He</creator><creator>Zhang, Huijuan</creator><creator>Liu, Xinqi</creator><general>Elsevier Ltd</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20190515</creationdate><title>Candida sp. 99-125 lipase-catalyzed synthesis of ergosterol linolenate and its characterization</title><author>He, Wen-Sen ; 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subjects alpha-Linolenic Acid - chemistry
alpha-Linolenic Acid - metabolism
Biocatalysis
Candida - enzymology
Candida sp. 99-125 lipase
Enzymes, Immobilized - chemistry
Enzymes, Immobilized - metabolism
Ergosterol - chemistry
Ergosterol - metabolism
Ergosterol ester
Esterification
Lipase - chemistry
Lipase - metabolism
Magnetic Resonance Spectroscopy
Oil solubility
Oils, Volatile - chemistry
Oils, Volatile - metabolism
Solubility
Temperature
α-Linolenic acid
title Candida sp. 99-125 lipase-catalyzed synthesis of ergosterol linolenate and its characterization
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