Impact of Lignosulfonates on the Thermodynamic and Kinetic Parameters of Malvidin-3‑O‑glucoside in Aqueous Solutions
The interaction of malvidin-3-O-glucoside (1) and a lignosulfonate was studied by UV–visible spectroscopy, and the results obtained showed the formation of a complex between the negatively charged lignosulfonate and the flavylium cation form (AH+) of this anthocyanin at pH 1. The thermodynamic and k...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2018-06, Vol.66 (25), p.6382-6387 |
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| creator | Araújo, Paula Basílio, Nuno Fernandes, Ana Mateus, Nuno de Freitas, Victor Pina, Fernando Oliveira, Joana |
| description | The interaction of malvidin-3-O-glucoside (1) and a lignosulfonate was studied by UV–visible spectroscopy, and the results obtained showed the formation of a complex between the negatively charged lignosulfonate and the flavylium cation form (AH+) of this anthocyanin at pH 1. The thermodynamic and kinetic parameters of 1 in the presence of a lignosulfonate were determined by UV–visible spectroscopy and stopped-flow techniques. The main differences were observed in the flavylium cation (AH+)/quinoidal base (A) equilibrium, the AH + form being more stabilized than A (pK a1 = 4.4 ± 0.1) compared with 1 in the absence of the lignosulfonate (pK a1 = 3.9 ± 0.1). Furthermore, comparing the hydration (k h = 0.028 s–1) and dehydration (k –h = 40 M–1 s–1) processes of 1 in the presence of the lignosulfonate with the processes of 1 (k h = 0.12 s–1 and k –h = 35 M–1 s–1) show that the hydration process is slower while the dehydration process is practically unaffected in the presence of the lignosulfonate. |
| doi_str_mv | 10.1021/acs.jafc.8b02273 |
| format | Article |
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The thermodynamic and kinetic parameters of 1 in the presence of a lignosulfonate were determined by UV–visible spectroscopy and stopped-flow techniques. The main differences were observed in the flavylium cation (AH+)/quinoidal base (A) equilibrium, the AH + form being more stabilized than A (pK a1 = 4.4 ± 0.1) compared with 1 in the absence of the lignosulfonate (pK a1 = 3.9 ± 0.1). Furthermore, comparing the hydration (k h = 0.028 s–1) and dehydration (k –h = 40 M–1 s–1) processes of 1 in the presence of the lignosulfonate with the processes of 1 (k h = 0.12 s–1 and k –h = 35 M–1 s–1) show that the hydration process is slower while the dehydration process is practically unaffected in the presence of the lignosulfonate.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/acs.jafc.8b02273</identifier><identifier>PMID: 29870233</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Anthocyanins - chemistry ; Glucosides - chemistry ; Hydrogen-Ion Concentration ; Kinetics ; Lignin - analogs & derivatives ; Lignin - chemistry ; Models, Chemical ; Molecular Structure ; Thermodynamics</subject><ispartof>Journal of agricultural and food chemistry, 2018-06, Vol.66 (25), p.6382-6387</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a336t-9cfaa90b6d53aabd8454181c60fd5013f666cd197f934dd22ea408e57be764c03</citedby><cites>FETCH-LOGICAL-a336t-9cfaa90b6d53aabd8454181c60fd5013f666cd197f934dd22ea408e57be764c03</cites><orcidid>0000-0001-8529-6848 ; 0000-0002-0121-3695 ; 0000-0003-0586-2278 ; 0000-0002-9996-1463</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.jafc.8b02273$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.jafc.8b02273$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2764,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29870233$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Araújo, Paula</creatorcontrib><creatorcontrib>Basílio, Nuno</creatorcontrib><creatorcontrib>Fernandes, Ana</creatorcontrib><creatorcontrib>Mateus, Nuno</creatorcontrib><creatorcontrib>de Freitas, Victor</creatorcontrib><creatorcontrib>Pina, Fernando</creatorcontrib><creatorcontrib>Oliveira, Joana</creatorcontrib><title>Impact of Lignosulfonates on the Thermodynamic and Kinetic Parameters of Malvidin-3‑O‑glucoside in Aqueous Solutions</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>The interaction of malvidin-3-O-glucoside (1) and a lignosulfonate was studied by UV–visible spectroscopy, and the results obtained showed the formation of a complex between the negatively charged lignosulfonate and the flavylium cation form (AH+) of this anthocyanin at pH 1. The thermodynamic and kinetic parameters of 1 in the presence of a lignosulfonate were determined by UV–visible spectroscopy and stopped-flow techniques. The main differences were observed in the flavylium cation (AH+)/quinoidal base (A) equilibrium, the AH + form being more stabilized than A (pK a1 = 4.4 ± 0.1) compared with 1 in the absence of the lignosulfonate (pK a1 = 3.9 ± 0.1). Furthermore, comparing the hydration (k h = 0.028 s–1) and dehydration (k –h = 40 M–1 s–1) processes of 1 in the presence of the lignosulfonate with the processes of 1 (k h = 0.12 s–1 and k –h = 35 M–1 s–1) show that the hydration process is slower while the dehydration process is practically unaffected in the presence of the lignosulfonate.</description><subject>Anthocyanins - chemistry</subject><subject>Glucosides - chemistry</subject><subject>Hydrogen-Ion Concentration</subject><subject>Kinetics</subject><subject>Lignin - analogs & derivatives</subject><subject>Lignin - chemistry</subject><subject>Models, Chemical</subject><subject>Molecular Structure</subject><subject>Thermodynamics</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kM1u1DAURi1ERYfCnhXykgWZXtuxkyyrCmjFVEWirKMb_7SuEnuwE0R3vAKv2CfBwwzdsbjyXZzv0_Uh5A2DNQPOTlHn9T06vW4H4LwRz8iKSQ6VZKx9TlZQmKqVih2TlznfA0ArG3hBjnnXNsCFWJGfl9MW9Uyjoxt_G2JeRhcDzjbTGOh8Z-nNnU1TNA8BJ68pBkM_-2Dnsn_BhJOdbcq7-BWOP7zxoRKPv35fl7kdFx2zN5b6QM--LzYumX6N4zL7GPIrcuRwzPb14T0h3z5-uDm_qDbXny7PzzYVCqHmqtMOsYNBGSkQB9PWsmYt0wqckcCEU0ppw7rGdaI2hnOLNbRWNoNtVK1BnJB3-95tiuWGPPeTz9qOI4bdQT0HyUApBnVBYY_qFHNO1vXb5CdMDz2Dfue7L777ne_-4LtE3h7al2Gy5inwT3AB3u-Bv9G4pFA--_--PyKUj18</recordid><startdate>20180627</startdate><enddate>20180627</enddate><creator>Araújo, Paula</creator><creator>Basílio, Nuno</creator><creator>Fernandes, Ana</creator><creator>Mateus, Nuno</creator><creator>de Freitas, Victor</creator><creator>Pina, Fernando</creator><creator>Oliveira, Joana</creator><general>American Chemical Society</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/0000-0001-8529-6848</orcidid><orcidid>https://orcid.org/0000-0002-0121-3695</orcidid><orcidid>https://orcid.org/0000-0003-0586-2278</orcidid><orcidid>https://orcid.org/0000-0002-9996-1463</orcidid></search><sort><creationdate>20180627</creationdate><title>Impact of Lignosulfonates on the Thermodynamic and Kinetic Parameters of Malvidin-3‑O‑glucoside in Aqueous Solutions</title><author>Araújo, Paula ; Basílio, Nuno ; Fernandes, Ana ; Mateus, Nuno ; de Freitas, Victor ; Pina, Fernando ; Oliveira, Joana</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a336t-9cfaa90b6d53aabd8454181c60fd5013f666cd197f934dd22ea408e57be764c03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Anthocyanins - chemistry</topic><topic>Glucosides - chemistry</topic><topic>Hydrogen-Ion Concentration</topic><topic>Kinetics</topic><topic>Lignin - analogs & derivatives</topic><topic>Lignin - chemistry</topic><topic>Models, Chemical</topic><topic>Molecular Structure</topic><topic>Thermodynamics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Araújo, Paula</creatorcontrib><creatorcontrib>Basílio, Nuno</creatorcontrib><creatorcontrib>Fernandes, Ana</creatorcontrib><creatorcontrib>Mateus, Nuno</creatorcontrib><creatorcontrib>de Freitas, Victor</creatorcontrib><creatorcontrib>Pina, Fernando</creatorcontrib><creatorcontrib>Oliveira, Joana</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>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Araújo, Paula</au><au>Basílio, Nuno</au><au>Fernandes, Ana</au><au>Mateus, Nuno</au><au>de Freitas, Victor</au><au>Pina, Fernando</au><au>Oliveira, Joana</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Impact of Lignosulfonates on the Thermodynamic and Kinetic Parameters of Malvidin-3‑O‑glucoside in Aqueous Solutions</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2018-06-27</date><risdate>2018</risdate><volume>66</volume><issue>25</issue><spage>6382</spage><epage>6387</epage><pages>6382-6387</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><abstract>The interaction of malvidin-3-O-glucoside (1) and a lignosulfonate was studied by UV–visible spectroscopy, and the results obtained showed the formation of a complex between the negatively charged lignosulfonate and the flavylium cation form (AH+) of this anthocyanin at pH 1. The thermodynamic and kinetic parameters of 1 in the presence of a lignosulfonate were determined by UV–visible spectroscopy and stopped-flow techniques. The main differences were observed in the flavylium cation (AH+)/quinoidal base (A) equilibrium, the AH + form being more stabilized than A (pK a1 = 4.4 ± 0.1) compared with 1 in the absence of the lignosulfonate (pK a1 = 3.9 ± 0.1). Furthermore, comparing the hydration (k h = 0.028 s–1) and dehydration (k –h = 40 M–1 s–1) processes of 1 in the presence of the lignosulfonate with the processes of 1 (k h = 0.12 s–1 and k –h = 35 M–1 s–1) show that the hydration process is slower while the dehydration process is practically unaffected in the presence of the lignosulfonate.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>29870233</pmid><doi>10.1021/acs.jafc.8b02273</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-8529-6848</orcidid><orcidid>https://orcid.org/0000-0002-0121-3695</orcidid><orcidid>https://orcid.org/0000-0003-0586-2278</orcidid><orcidid>https://orcid.org/0000-0002-9996-1463</orcidid></addata></record> |
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| subjects | Anthocyanins - chemistry Glucosides - chemistry Hydrogen-Ion Concentration Kinetics Lignin - analogs & derivatives Lignin - chemistry Models, Chemical Molecular Structure Thermodynamics |
| title | Impact of Lignosulfonates on the Thermodynamic and Kinetic Parameters of Malvidin-3‑O‑glucoside in Aqueous Solutions |
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