Application of Hansch’s Model to Capsaicinoids and Capsinoids: A Study Using the Quantitative Structure−Activity Relationship. A Novel Method for the Synthesis of Capsinoids
We describe a synthetic approach for two families of compounds, the capsaicinoids and capsinoids, as part of a study of the quantitative relationship between structure and activity. A total of 14 capsaicinoids of increasing lateral chain lengths, from 2 to 16 carbon atoms, were synthesized. In addit...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2010-03, Vol.58 (6), p.3342-3349 |
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| container_title | Journal of agricultural and food chemistry |
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| creator | Barbero, Gerardo F Molinillo, José M. G Varela, Rosa M Palma, Miguel Macías, Francisco A Barroso, Carmelo G |
| description | We describe a synthetic approach for two families of compounds, the capsaicinoids and capsinoids, as part of a study of the quantitative relationship between structure and activity. A total of 14 capsaicinoids of increasing lateral chain lengths, from 2 to 16 carbon atoms, were synthesized. In addition, 14 capsinoids with identical lateral chains, as well as capsiate and dihydrocapsiate, have been synthesized, and a new method for the synthesis of these compounds has been developed. The yields range from 48.35 to 98.98%. It has been found that the synthetic capsaicinoids and capsinoids present a lipophilia similar to those of the natural compounds and present similar biological activity. The bioactivity of the synthetic capsaicinoids and capsinoids decreases proportionally to the degree of difference in lipophilia (higher or lower) compared to the natural compounds. Biological activity was determined using the etiolated wheat (Triticum aestivum L.) coleoptiles bioassay and by comparing results of the synthesis with those presented by their counterpart natural compounds. The bioactivities found correlated directly to the lipophilic properties of the synthesized compounds. |
| doi_str_mv | 10.1021/jf9035029 |
| format | Article |
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A Novel Method for the Synthesis of Capsinoids</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Barbero, Gerardo F ; Molinillo, José M. G ; Varela, Rosa M ; Palma, Miguel ; Macías, Francisco A ; Barroso, Carmelo G</creator><creatorcontrib>Barbero, Gerardo F ; Molinillo, José M. G ; Varela, Rosa M ; Palma, Miguel ; Macías, Francisco A ; Barroso, Carmelo G</creatorcontrib><description>We describe a synthetic approach for two families of compounds, the capsaicinoids and capsinoids, as part of a study of the quantitative relationship between structure and activity. A total of 14 capsaicinoids of increasing lateral chain lengths, from 2 to 16 carbon atoms, were synthesized. In addition, 14 capsinoids with identical lateral chains, as well as capsiate and dihydrocapsiate, have been synthesized, and a new method for the synthesis of these compounds has been developed. The yields range from 48.35 to 98.98%. It has been found that the synthetic capsaicinoids and capsinoids present a lipophilia similar to those of the natural compounds and present similar biological activity. The bioactivity of the synthetic capsaicinoids and capsinoids decreases proportionally to the degree of difference in lipophilia (higher or lower) compared to the natural compounds. Biological activity was determined using the etiolated wheat (Triticum aestivum L.) coleoptiles bioassay and by comparing results of the synthesis with those presented by their counterpart natural compounds. The bioactivities found correlated directly to the lipophilic properties of the synthesized compounds.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf9035029</identifier><identifier>PMID: 20178388</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alkaloids - chemical synthesis ; Alkaloids - chemistry ; Alkaloids - pharmacology ; Bioactive Constituents ; bioactive properties ; Biological and medical sciences ; capsaicin ; chemical structure ; Food industries ; Fundamental and applied biological sciences. Psychology ; General aspects ; Handling, storage, packaging, transport ; Hansch's model ; hydrophobicity ; Models, Molecular ; Molecular Structure ; quantitative analysis ; Quantitative Structure-Activity Relationship ; structure-activity relationships ; synthesis ; Triticum - drug effects ; Triticum - growth & development ; yields</subject><ispartof>Journal of agricultural and food chemistry, 2010-03, Vol.58 (6), p.3342-3349</ispartof><rights>Copyright © 2010 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a368t-9997fd98a0bca2605b774647c219ab7d47570e052ab0ba7905d1f58d7290b113</citedby><cites>FETCH-LOGICAL-a368t-9997fd98a0bca2605b774647c219ab7d47570e052ab0ba7905d1f58d7290b113</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jf9035029$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf9035029$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22546259$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20178388$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Barbero, Gerardo F</creatorcontrib><creatorcontrib>Molinillo, José M. G</creatorcontrib><creatorcontrib>Varela, Rosa M</creatorcontrib><creatorcontrib>Palma, Miguel</creatorcontrib><creatorcontrib>Macías, Francisco A</creatorcontrib><creatorcontrib>Barroso, Carmelo G</creatorcontrib><title>Application of Hansch’s Model to Capsaicinoids and Capsinoids: A Study Using the Quantitative Structure−Activity Relationship. A Novel Method for the Synthesis of Capsinoids</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>We describe a synthetic approach for two families of compounds, the capsaicinoids and capsinoids, as part of a study of the quantitative relationship between structure and activity. A total of 14 capsaicinoids of increasing lateral chain lengths, from 2 to 16 carbon atoms, were synthesized. In addition, 14 capsinoids with identical lateral chains, as well as capsiate and dihydrocapsiate, have been synthesized, and a new method for the synthesis of these compounds has been developed. The yields range from 48.35 to 98.98%. It has been found that the synthetic capsaicinoids and capsinoids present a lipophilia similar to those of the natural compounds and present similar biological activity. The bioactivity of the synthetic capsaicinoids and capsinoids decreases proportionally to the degree of difference in lipophilia (higher or lower) compared to the natural compounds. Biological activity was determined using the etiolated wheat (Triticum aestivum L.) coleoptiles bioassay and by comparing results of the synthesis with those presented by their counterpart natural compounds. The bioactivities found correlated directly to the lipophilic properties of the synthesized compounds.</description><subject>Alkaloids - chemical synthesis</subject><subject>Alkaloids - chemistry</subject><subject>Alkaloids - pharmacology</subject><subject>Bioactive Constituents</subject><subject>bioactive properties</subject><subject>Biological and medical sciences</subject><subject>capsaicin</subject><subject>chemical structure</subject><subject>Food industries</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>General aspects</subject><subject>Handling, storage, packaging, transport</subject><subject>Hansch's model</subject><subject>hydrophobicity</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>quantitative analysis</subject><subject>Quantitative Structure-Activity Relationship</subject><subject>structure-activity relationships</subject><subject>synthesis</subject><subject>Triticum - drug effects</subject><subject>Triticum - growth & development</subject><subject>yields</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc9u1DAQhy0EokvhwAuALwhxSGs7cexwW62AVmqpYNtzNLGdrlfZONhOpb1x5MyNx-CV-iT1_qF74WR55tM3o_kh9JqSE0oYPV22Fck5YdUTNKGckYxTKp-iCUnNTPKSHqEXISwJIZIL8hwdMUKFzKWcoL_TYeisgmhdj12Lz6APanH_80_Al06bDkeHZzAEsMr2zuqAodfbyu77EU_xPI56jW9S5RbHhcHfRuijjcl5Z1LTjyqO3tz_-j1VqWTjGn833XZiWNjhJBm-urs06tLEhdO4dX6rma_79AQbNnsdJr5Ez1rognm1f4_R9edP17Oz7OLqy_lsepFBXsqYVVUlWl1JII0CVhLeCFGUhVCMVtAIXYh0CkM4g4Y0ICrCNW251IJVpKE0P0bvd9rBux-jCbFe2aBM10Fv3BhqkeeClkzmifywI5V3IXjT1oO3K_DrmpJ6k0_9mE9i3-ytY7My-pH8F0gC3u0BCAq61kOvbDhwjBcl4xvR2x3Xgqvh1ifmZp4sOaGSFSnngwlUqJdu9H261n9WegDutrBP</recordid><startdate>20100324</startdate><enddate>20100324</enddate><creator>Barbero, Gerardo F</creator><creator>Molinillo, José M. G</creator><creator>Varela, Rosa M</creator><creator>Palma, Miguel</creator><creator>Macías, Francisco A</creator><creator>Barroso, Carmelo G</creator><general>American Chemical Society</general><scope>FBQ</scope><scope>IQODW</scope><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>20100324</creationdate><title>Application of Hansch’s Model to Capsaicinoids and Capsinoids: A Study Using the Quantitative Structure−Activity Relationship. A Novel Method for the Synthesis of Capsinoids</title><author>Barbero, Gerardo F ; Molinillo, José M. G ; Varela, Rosa M ; Palma, Miguel ; Macías, Francisco A ; Barroso, Carmelo G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a368t-9997fd98a0bca2605b774647c219ab7d47570e052ab0ba7905d1f58d7290b113</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Alkaloids - chemical synthesis</topic><topic>Alkaloids - chemistry</topic><topic>Alkaloids - pharmacology</topic><topic>Bioactive Constituents</topic><topic>bioactive properties</topic><topic>Biological and medical sciences</topic><topic>capsaicin</topic><topic>chemical structure</topic><topic>Food industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>General aspects</topic><topic>Handling, storage, packaging, transport</topic><topic>Hansch's model</topic><topic>hydrophobicity</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>quantitative analysis</topic><topic>Quantitative Structure-Activity Relationship</topic><topic>structure-activity relationships</topic><topic>synthesis</topic><topic>Triticum - drug effects</topic><topic>Triticum - growth & development</topic><topic>yields</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Barbero, Gerardo F</creatorcontrib><creatorcontrib>Molinillo, José M. G</creatorcontrib><creatorcontrib>Varela, Rosa M</creatorcontrib><creatorcontrib>Palma, Miguel</creatorcontrib><creatorcontrib>Macías, Francisco A</creatorcontrib><creatorcontrib>Barroso, Carmelo G</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><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>Barbero, Gerardo F</au><au>Molinillo, José M. G</au><au>Varela, Rosa M</au><au>Palma, Miguel</au><au>Macías, Francisco A</au><au>Barroso, Carmelo G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Application of Hansch’s Model to Capsaicinoids and Capsinoids: A Study Using the Quantitative Structure−Activity Relationship. A Novel Method for the Synthesis of Capsinoids</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2010-03-24</date><risdate>2010</risdate><volume>58</volume><issue>6</issue><spage>3342</spage><epage>3349</epage><pages>3342-3349</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>We describe a synthetic approach for two families of compounds, the capsaicinoids and capsinoids, as part of a study of the quantitative relationship between structure and activity. A total of 14 capsaicinoids of increasing lateral chain lengths, from 2 to 16 carbon atoms, were synthesized. In addition, 14 capsinoids with identical lateral chains, as well as capsiate and dihydrocapsiate, have been synthesized, and a new method for the synthesis of these compounds has been developed. The yields range from 48.35 to 98.98%. It has been found that the synthetic capsaicinoids and capsinoids present a lipophilia similar to those of the natural compounds and present similar biological activity. The bioactivity of the synthetic capsaicinoids and capsinoids decreases proportionally to the degree of difference in lipophilia (higher or lower) compared to the natural compounds. Biological activity was determined using the etiolated wheat (Triticum aestivum L.) coleoptiles bioassay and by comparing results of the synthesis with those presented by their counterpart natural compounds. The bioactivities found correlated directly to the lipophilic properties of the synthesized compounds.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>20178388</pmid><doi>10.1021/jf9035029</doi><tpages>8</tpages></addata></record> |
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| subjects | Alkaloids - chemical synthesis Alkaloids - chemistry Alkaloids - pharmacology Bioactive Constituents bioactive properties Biological and medical sciences capsaicin chemical structure Food industries Fundamental and applied biological sciences. Psychology General aspects Handling, storage, packaging, transport Hansch's model hydrophobicity Models, Molecular Molecular Structure quantitative analysis Quantitative Structure-Activity Relationship structure-activity relationships synthesis Triticum - drug effects Triticum - growth & development yields |
| title | Application of Hansch’s Model to Capsaicinoids and Capsinoids: A Study Using the Quantitative Structure−Activity Relationship. A Novel Method for the Synthesis of Capsinoids |
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