New acylated cyanidin glycosides extracted from underutilized potential sources: Enzymatic synthesis, antioxidant activity and thermostability
•Evaluation of five underutilized plants to obtain sources of cyanidin glycosides.•Reaction conditions of enzymatic esterification to anthocyanins for the food industry.•Synthesis of four new anthocyanins derived from dihydrocinnamic acids.•Development of cyanidin esters with more thermostability an...
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Veröffentlicht in: | Food chemistry 2020-03, Vol.309, p.125796-125796, Article 125796 |
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creator | Fernandez-Aulis, Fernanda Torres, Andrea Sanchez-Mendoza, Ernesto Cruz, Luis Navarro-Ocana, Arturo |
description | •Evaluation of five underutilized plants to obtain sources of cyanidin glycosides.•Reaction conditions of enzymatic esterification to anthocyanins for the food industry.•Synthesis of four new anthocyanins derived from dihydrocinnamic acids.•Development of cyanidin esters with more thermostability and antioxidant activity.
Interest in anthocyanins has increased remarkably in recent decades, although their wider application has been hampered by instability problems. Thus, this study aimed at developing a strategy to gain access to more stable anthocyanins via enzymatic esterification. For that purpose, three cyanidin derivatives were obtained from underutilized, but easily accessible sources, and their total anthocyanin content was quantified. The purity of cyanidins obtained ranged from 40% to 88% depending on their source. Subsequently, the critical enzymatic reaction conditions were established, and the best results were found using tert-butanol as a solvent, 20 g/L of lipase B from Candida Antarctica, and vinyl cinnamate as acyl donor at ratio 250:1 (acyl donor to anthocyanin). Finally, five new acylated anthocyanin derivatives were synthesized with improved antioxidant activity and thermostability, in comparison to the cyanidin-3-glucoside, which is an advantageous feature for industrial applications. |
doi_str_mv | 10.1016/j.foodchem.2019.125796 |
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Interest in anthocyanins has increased remarkably in recent decades, although their wider application has been hampered by instability problems. Thus, this study aimed at developing a strategy to gain access to more stable anthocyanins via enzymatic esterification. For that purpose, three cyanidin derivatives were obtained from underutilized, but easily accessible sources, and their total anthocyanin content was quantified. The purity of cyanidins obtained ranged from 40% to 88% depending on their source. Subsequently, the critical enzymatic reaction conditions were established, and the best results were found using tert-butanol as a solvent, 20 g/L of lipase B from Candida Antarctica, and vinyl cinnamate as acyl donor at ratio 250:1 (acyl donor to anthocyanin). Finally, five new acylated anthocyanin derivatives were synthesized with improved antioxidant activity and thermostability, in comparison to the cyanidin-3-glucoside, which is an advantageous feature for industrial applications.</description><identifier>ISSN: 0308-8146</identifier><identifier>EISSN: 1873-7072</identifier><identifier>DOI: 10.1016/j.foodchem.2019.125796</identifier><identifier>PMID: 31706678</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Acylated anthocyanin ; Acylation ; Anthocyanins - chemistry ; Anthocyanins - metabolism ; Antioxidants - chemistry ; Cinnamates - chemistry ; Dihydrocinnamic acids ; Enzymatic esterification ; Esterification ; Fungal Proteins - metabolism ; Glucosides - chemistry ; Glucosides - metabolism ; Lipase - metabolism ; Lipases ; Magnetic Resonance Spectroscopy ; Prunus domestica - chemistry ; Prunus domestica - metabolism ; Solvents - chemistry ; Temperature</subject><ispartof>Food chemistry, 2020-03, Vol.309, p.125796-125796, Article 125796</ispartof><rights>2019 Elsevier Ltd</rights><rights>Copyright © 2019 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c368t-bf16ed8b55d94a0f8b267ce24463055c56e145b917fe2ec199643da75bfb388a3</citedby><cites>FETCH-LOGICAL-c368t-bf16ed8b55d94a0f8b267ce24463055c56e145b917fe2ec199643da75bfb388a3</cites><orcidid>0000-0003-2226-0404</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.foodchem.2019.125796$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31706678$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Fernandez-Aulis, Fernanda</creatorcontrib><creatorcontrib>Torres, Andrea</creatorcontrib><creatorcontrib>Sanchez-Mendoza, Ernesto</creatorcontrib><creatorcontrib>Cruz, Luis</creatorcontrib><creatorcontrib>Navarro-Ocana, Arturo</creatorcontrib><title>New acylated cyanidin glycosides extracted from underutilized potential sources: Enzymatic synthesis, antioxidant activity and thermostability</title><title>Food chemistry</title><addtitle>Food Chem</addtitle><description>•Evaluation of five underutilized plants to obtain sources of cyanidin glycosides.•Reaction conditions of enzymatic esterification to anthocyanins for the food industry.•Synthesis of four new anthocyanins derived from dihydrocinnamic acids.•Development of cyanidin esters with more thermostability and antioxidant activity.
Interest in anthocyanins has increased remarkably in recent decades, although their wider application has been hampered by instability problems. Thus, this study aimed at developing a strategy to gain access to more stable anthocyanins via enzymatic esterification. For that purpose, three cyanidin derivatives were obtained from underutilized, but easily accessible sources, and their total anthocyanin content was quantified. The purity of cyanidins obtained ranged from 40% to 88% depending on their source. Subsequently, the critical enzymatic reaction conditions were established, and the best results were found using tert-butanol as a solvent, 20 g/L of lipase B from Candida Antarctica, and vinyl cinnamate as acyl donor at ratio 250:1 (acyl donor to anthocyanin). Finally, five new acylated anthocyanin derivatives were synthesized with improved antioxidant activity and thermostability, in comparison to the cyanidin-3-glucoside, which is an advantageous feature for industrial applications.</description><subject>Acylated anthocyanin</subject><subject>Acylation</subject><subject>Anthocyanins - chemistry</subject><subject>Anthocyanins - metabolism</subject><subject>Antioxidants - chemistry</subject><subject>Cinnamates - chemistry</subject><subject>Dihydrocinnamic acids</subject><subject>Enzymatic esterification</subject><subject>Esterification</subject><subject>Fungal Proteins - metabolism</subject><subject>Glucosides - chemistry</subject><subject>Glucosides - metabolism</subject><subject>Lipase - metabolism</subject><subject>Lipases</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Prunus domestica - chemistry</subject><subject>Prunus domestica - metabolism</subject><subject>Solvents - chemistry</subject><subject>Temperature</subject><issn>0308-8146</issn><issn>1873-7072</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc1O3TAQha0KVG5pXwF5yYLc2nH8E1atEP2REGxgbTn2pPgqiW9thxIegmeury6wZTXSmW_maOYgdELJmhIqvm7WfQjO3sO4rglt17TmshUf0IoqySpJZH2AVoQRVSnaiCP0KaUNIaSw6iM6YlQSIaRaoedr-IeNXQaTwWG7mMk7P-E_w2JD8g4Shsccjd11-xhGPE8O4pz94J-KtA0ZpuzNgFOYo4V0ji-np2U02VuclinfQ_LpDJsChUfvSi1u2T_4vBTR4QLEMaRsurIxL5_RYW-GBF9e6jG6-3F5e_Grurr5-fvi-1VlmVC56noqwKmOc9c2hvSqq4W0UDeNYIRzywXQhnctlT3UYGnbioY5I3nXd0wpw47R6X7vNoa_M6SsR58sDIOZIMxJ14wywTmhsqBij9oYUorQ6230o4mLpkTvstAb_ZqF3mWh91mUwZMXj7kbwb2NvT6_AN_2AJRLHzxEnayHyYLzEWzWLvj3PP4D9Pii-g</recordid><startdate>20200330</startdate><enddate>20200330</enddate><creator>Fernandez-Aulis, Fernanda</creator><creator>Torres, Andrea</creator><creator>Sanchez-Mendoza, Ernesto</creator><creator>Cruz, Luis</creator><creator>Navarro-Ocana, Arturo</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><orcidid>https://orcid.org/0000-0003-2226-0404</orcidid></search><sort><creationdate>20200330</creationdate><title>New acylated cyanidin glycosides extracted from underutilized potential sources: Enzymatic synthesis, antioxidant activity and thermostability</title><author>Fernandez-Aulis, Fernanda ; Torres, Andrea ; Sanchez-Mendoza, Ernesto ; Cruz, Luis ; Navarro-Ocana, Arturo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c368t-bf16ed8b55d94a0f8b267ce24463055c56e145b917fe2ec199643da75bfb388a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Acylated anthocyanin</topic><topic>Acylation</topic><topic>Anthocyanins - chemistry</topic><topic>Anthocyanins - metabolism</topic><topic>Antioxidants - chemistry</topic><topic>Cinnamates - chemistry</topic><topic>Dihydrocinnamic acids</topic><topic>Enzymatic esterification</topic><topic>Esterification</topic><topic>Fungal Proteins - metabolism</topic><topic>Glucosides - chemistry</topic><topic>Glucosides - metabolism</topic><topic>Lipase - metabolism</topic><topic>Lipases</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Prunus domestica - chemistry</topic><topic>Prunus domestica - metabolism</topic><topic>Solvents - chemistry</topic><topic>Temperature</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fernandez-Aulis, Fernanda</creatorcontrib><creatorcontrib>Torres, Andrea</creatorcontrib><creatorcontrib>Sanchez-Mendoza, Ernesto</creatorcontrib><creatorcontrib>Cruz, Luis</creatorcontrib><creatorcontrib>Navarro-Ocana, Arturo</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>Fernandez-Aulis, Fernanda</au><au>Torres, Andrea</au><au>Sanchez-Mendoza, Ernesto</au><au>Cruz, Luis</au><au>Navarro-Ocana, Arturo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New acylated cyanidin glycosides extracted from underutilized potential sources: Enzymatic synthesis, antioxidant activity and thermostability</atitle><jtitle>Food chemistry</jtitle><addtitle>Food Chem</addtitle><date>2020-03-30</date><risdate>2020</risdate><volume>309</volume><spage>125796</spage><epage>125796</epage><pages>125796-125796</pages><artnum>125796</artnum><issn>0308-8146</issn><eissn>1873-7072</eissn><abstract>•Evaluation of five underutilized plants to obtain sources of cyanidin glycosides.•Reaction conditions of enzymatic esterification to anthocyanins for the food industry.•Synthesis of four new anthocyanins derived from dihydrocinnamic acids.•Development of cyanidin esters with more thermostability and antioxidant activity.
Interest in anthocyanins has increased remarkably in recent decades, although their wider application has been hampered by instability problems. Thus, this study aimed at developing a strategy to gain access to more stable anthocyanins via enzymatic esterification. For that purpose, three cyanidin derivatives were obtained from underutilized, but easily accessible sources, and their total anthocyanin content was quantified. The purity of cyanidins obtained ranged from 40% to 88% depending on their source. Subsequently, the critical enzymatic reaction conditions were established, and the best results were found using tert-butanol as a solvent, 20 g/L of lipase B from Candida Antarctica, and vinyl cinnamate as acyl donor at ratio 250:1 (acyl donor to anthocyanin). Finally, five new acylated anthocyanin derivatives were synthesized with improved antioxidant activity and thermostability, in comparison to the cyanidin-3-glucoside, which is an advantageous feature for industrial applications.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>31706678</pmid><doi>10.1016/j.foodchem.2019.125796</doi><tpages>1</tpages><orcidid>https://orcid.org/0000-0003-2226-0404</orcidid></addata></record> |
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subjects | Acylated anthocyanin Acylation Anthocyanins - chemistry Anthocyanins - metabolism Antioxidants - chemistry Cinnamates - chemistry Dihydrocinnamic acids Enzymatic esterification Esterification Fungal Proteins - metabolism Glucosides - chemistry Glucosides - metabolism Lipase - metabolism Lipases Magnetic Resonance Spectroscopy Prunus domestica - chemistry Prunus domestica - metabolism Solvents - chemistry Temperature |
title | New acylated cyanidin glycosides extracted from underutilized potential sources: Enzymatic synthesis, antioxidant activity and thermostability |
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