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 |
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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. 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><identifier>ISSN: 0308-8146</identifier><identifier>EISSN: 1873-7072</identifier><identifier>DOI: 10.1016/j.foodchem.2018.12.076</identifier><identifier>PMID: 30642499</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>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</subject><ispartof>Food chemistry, 2019-05, Vol.280, p.286-293</ispartof><rights>2018 Elsevier Ltd</rights><rights>Copyright © 2018 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c405t-1fdca7e9ed9a93725c0dea456820dd95c991ed985959be3136d615b18da9e8e53</citedby><cites>FETCH-LOGICAL-c405t-1fdca7e9ed9a93725c0dea456820dd95c991ed985959be3136d615b18da9e8e53</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0308814618321800$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65534</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30642499$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>He, Wen-Sen</creatorcontrib><creatorcontrib>Li, Lingling</creatorcontrib><creatorcontrib>Zhao, Jia</creatorcontrib><creatorcontrib>Xu, Hanshan</creatorcontrib><creatorcontrib>Rui, Jiaxin</creatorcontrib><creatorcontrib>Cui, Dandan</creatorcontrib><creatorcontrib>Li, He</creatorcontrib><creatorcontrib>Zhang, Huijuan</creatorcontrib><creatorcontrib>Liu, Xinqi</creatorcontrib><title>Candida sp. 99-125 lipase-catalyzed synthesis of ergosterol linolenate and its characterization</title><title>Food chemistry</title><addtitle>Food Chem</addtitle><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.</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 ; Li, Lingling ; Zhao, Jia ; Xu, Hanshan ; Rui, Jiaxin ; Cui, Dandan ; Li, He ; Zhang, Huijuan ; Liu, Xinqi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c405t-1fdca7e9ed9a93725c0dea456820dd95c991ed985959be3136d615b18da9e8e53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>alpha-Linolenic Acid - chemistry</topic><topic>alpha-Linolenic Acid - metabolism</topic><topic>Biocatalysis</topic><topic>Candida - enzymology</topic><topic>Candida sp. 99-125 lipase</topic><topic>Enzymes, Immobilized - chemistry</topic><topic>Enzymes, Immobilized - metabolism</topic><topic>Ergosterol - chemistry</topic><topic>Ergosterol - metabolism</topic><topic>Ergosterol ester</topic><topic>Esterification</topic><topic>Lipase - chemistry</topic><topic>Lipase - metabolism</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Oil solubility</topic><topic>Oils, Volatile - chemistry</topic><topic>Oils, Volatile - metabolism</topic><topic>Solubility</topic><topic>Temperature</topic><topic>α-Linolenic acid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>He, Wen-Sen</creatorcontrib><creatorcontrib>Li, Lingling</creatorcontrib><creatorcontrib>Zhao, Jia</creatorcontrib><creatorcontrib>Xu, Hanshan</creatorcontrib><creatorcontrib>Rui, Jiaxin</creatorcontrib><creatorcontrib>Cui, Dandan</creatorcontrib><creatorcontrib>Li, He</creatorcontrib><creatorcontrib>Zhang, Huijuan</creatorcontrib><creatorcontrib>Liu, Xinqi</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>He, Wen-Sen</au><au>Li, Lingling</au><au>Zhao, Jia</au><au>Xu, Hanshan</au><au>Rui, Jiaxin</au><au>Cui, Dandan</au><au>Li, He</au><au>Zhang, Huijuan</au><au>Liu, Xinqi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Candida sp. 99-125 lipase-catalyzed synthesis of ergosterol linolenate and its characterization</atitle><jtitle>Food chemistry</jtitle><addtitle>Food Chem</addtitle><date>2019-05-15</date><risdate>2019</risdate><volume>280</volume><spage>286</spage><epage>293</epage><pages>286-293</pages><issn>0308-8146</issn><eissn>1873-7072</eissn><abstract>•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.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>30642499</pmid><doi>10.1016/j.foodchem.2018.12.076</doi><tpages>8</tpages></addata></record> |
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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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