Effect of hydroxyl on antioxidant properties of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one to scavenge free radicals
It is well known that 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP) is usually formed in the Maillard reaction and it contributes to the antioxidant properties of Maillard reaction intermediates. A series of hydroxyl group protected DDMP derivatives were synthesized to further understand...
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| Veröffentlicht in: | RSC advances 2021-10, Vol.11 (55), p.34456-34461 |
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| container_issue | 55 |
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| container_title | RSC advances |
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| creator | Chen, Zhifei Liu, Qiang Zhao, Zhiwei Bai, Bing Sun, Zhitao Cai, Lili Fu, Yufeng Ma, Yuping Wang, Qingfu Gaolei Xi |
| description | It is well known that 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP) is usually formed in the Maillard reaction and it contributes to the antioxidant properties of Maillard reaction intermediates. A series of hydroxyl group protected DDMP derivatives were synthesized to further understand the source of antioxidant activity. Antioxidant abilities of the DDMP derivatives were evaluated by scavenging the 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS·+), 2,2′-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, respectively. It was found that the introduction of protecting groups to the free hydroxyl groups of DDMP decreases their reducing abilities. In particular, the hydroxyl group at the olefin position exhibited a remarkable impact on the antioxidant activity of DDMP, indicating that the unstable enol structure in the DDMP moiety is the key factor for its antioxidant activity. |
| doi_str_mv | 10.1039/d1ra06317k |
| format | Article |
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A series of hydroxyl group protected DDMP derivatives were synthesized to further understand the source of antioxidant activity. Antioxidant abilities of the DDMP derivatives were evaluated by scavenging the 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS·+), 2,2′-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, respectively. It was found that the introduction of protecting groups to the free hydroxyl groups of DDMP decreases their reducing abilities. In particular, the hydroxyl group at the olefin position exhibited a remarkable impact on the antioxidant activity of DDMP, indicating that the unstable enol structure in the DDMP moiety is the key factor for its antioxidant activity.</description><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/d1ra06317k</identifier><identifier>PMID: 35494787</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Antioxidants ; Chemistry ; Free radicals ; Hydroxyl groups ; Maillard reaction ; Reaction intermediates ; Scavenging</subject><ispartof>RSC advances, 2021-10, Vol.11 (55), p.34456-34461</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><rights>This journal is © The Royal Society of Chemistry 2021 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9042674/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9042674/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,864,885,27924,27925,53791,53793</link.rule.ids></links><search><creatorcontrib>Chen, Zhifei</creatorcontrib><creatorcontrib>Liu, Qiang</creatorcontrib><creatorcontrib>Zhao, Zhiwei</creatorcontrib><creatorcontrib>Bai, Bing</creatorcontrib><creatorcontrib>Sun, Zhitao</creatorcontrib><creatorcontrib>Cai, Lili</creatorcontrib><creatorcontrib>Fu, Yufeng</creatorcontrib><creatorcontrib>Ma, Yuping</creatorcontrib><creatorcontrib>Wang, Qingfu</creatorcontrib><creatorcontrib>Gaolei Xi</creatorcontrib><title>Effect of hydroxyl on antioxidant properties of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one to scavenge free radicals</title><title>RSC advances</title><description>It is well known that 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP) is usually formed in the Maillard reaction and it contributes to the antioxidant properties of Maillard reaction intermediates. A series of hydroxyl group protected DDMP derivatives were synthesized to further understand the source of antioxidant activity. Antioxidant abilities of the DDMP derivatives were evaluated by scavenging the 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS·+), 2,2′-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, respectively. It was found that the introduction of protecting groups to the free hydroxyl groups of DDMP decreases their reducing abilities. In particular, the hydroxyl group at the olefin position exhibited a remarkable impact on the antioxidant activity of DDMP, indicating that the unstable enol structure in the DDMP moiety is the key factor for its antioxidant activity.</description><subject>Antioxidants</subject><subject>Chemistry</subject><subject>Free radicals</subject><subject>Hydroxyl groups</subject><subject>Maillard reaction</subject><subject>Reaction intermediates</subject><subject>Scavenging</subject><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpdj8tKxTAQhoMgKurGJwi4cWE098tGEPEGghtdl7SZeqI9SU175BRf3npb6Gz-gfn4hh-hA0ZPGBXuNLDiqRbMvGygHU6lJpxqt432h-GZzqMV45ptoW2hpJPGmh30ftm20Iw4t3gxhZLXU4dzwj6NMa9jmBP3JfdQxgjDJ8WPBQnxiyXiWP3u64losoRxMXVE3pB-Kj4RSXICPGY8NP4N0hPgtgDg4kNsfDfsoc12Dtj_yV30eHX5cHFD7u6vby_O70jPhRmJCY5KcJS7mlmgFpTwzLPaSuXBKCskDyIw4aRqhGsN94Zb4YJgdVO33IhddPbt7Vf1EkIDaSy-q_oSl75MVfax-ntJcVE95bdq_su1kbPg6EdQ8usKhrFaxqGBrvMJ8mqouFZWK8mVmtHDf-hzXpU016u4clZYOjvFByRKg9o</recordid><startdate>20211025</startdate><enddate>20211025</enddate><creator>Chen, Zhifei</creator><creator>Liu, Qiang</creator><creator>Zhao, Zhiwei</creator><creator>Bai, Bing</creator><creator>Sun, Zhitao</creator><creator>Cai, Lili</creator><creator>Fu, Yufeng</creator><creator>Ma, Yuping</creator><creator>Wang, Qingfu</creator><creator>Gaolei Xi</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20211025</creationdate><title>Effect of hydroxyl on antioxidant properties of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one to scavenge free radicals</title><author>Chen, Zhifei ; Liu, Qiang ; Zhao, Zhiwei ; Bai, Bing ; Sun, Zhitao ; Cai, Lili ; Fu, Yufeng ; Ma, Yuping ; Wang, Qingfu ; Gaolei Xi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p237t-7d904e9029b18e08e53a1a1b845ae758342d3d13945c39f72a72839d31bcbf273</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Antioxidants</topic><topic>Chemistry</topic><topic>Free radicals</topic><topic>Hydroxyl groups</topic><topic>Maillard reaction</topic><topic>Reaction intermediates</topic><topic>Scavenging</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Zhifei</creatorcontrib><creatorcontrib>Liu, Qiang</creatorcontrib><creatorcontrib>Zhao, Zhiwei</creatorcontrib><creatorcontrib>Bai, Bing</creatorcontrib><creatorcontrib>Sun, Zhitao</creatorcontrib><creatorcontrib>Cai, Lili</creatorcontrib><creatorcontrib>Fu, Yufeng</creatorcontrib><creatorcontrib>Ma, Yuping</creatorcontrib><creatorcontrib>Wang, Qingfu</creatorcontrib><creatorcontrib>Gaolei Xi</creatorcontrib><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, Zhifei</au><au>Liu, Qiang</au><au>Zhao, Zhiwei</au><au>Bai, Bing</au><au>Sun, Zhitao</au><au>Cai, Lili</au><au>Fu, Yufeng</au><au>Ma, Yuping</au><au>Wang, Qingfu</au><au>Gaolei Xi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Effect of hydroxyl on antioxidant properties of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one to scavenge free radicals</atitle><jtitle>RSC advances</jtitle><date>2021-10-25</date><risdate>2021</risdate><volume>11</volume><issue>55</issue><spage>34456</spage><epage>34461</epage><pages>34456-34461</pages><eissn>2046-2069</eissn><abstract>It is well known that 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP) is usually formed in the Maillard reaction and it contributes to the antioxidant properties of Maillard reaction intermediates. A series of hydroxyl group protected DDMP derivatives were synthesized to further understand the source of antioxidant activity. Antioxidant abilities of the DDMP derivatives were evaluated by scavenging the 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS·+), 2,2′-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, respectively. It was found that the introduction of protecting groups to the free hydroxyl groups of DDMP decreases their reducing abilities. In particular, the hydroxyl group at the olefin position exhibited a remarkable impact on the antioxidant activity of DDMP, indicating that the unstable enol structure in the DDMP moiety is the key factor for its antioxidant activity.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><pmid>35494787</pmid><doi>10.1039/d1ra06317k</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| source | PubMed Central; Directory of Open Access Journals; EZB Electronic Journals Library; PubMed Central Open Access |
| subjects | Antioxidants Chemistry Free radicals Hydroxyl groups Maillard reaction Reaction intermediates Scavenging |
| title | Effect of hydroxyl on antioxidant properties of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one to scavenge free radicals |
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