Acetylcholinesterase-Inhibitory Activity of Linarin from Buddleja davidii, Structure-Activity Relationships of Related Flavonoids, and Chemical Investigation of Buddleja nitida
Abstract In order to find some medicinal value for invasive neophytes, inhibition of acetylcholinesterase of Reynoutria sachalinensis F. Schmidt ex Maxim. (Polygonaceae), Polygonum cuspidatum Siebold. & Zucc. (Polygonaceae), Heracleum mantegazzianum Sommier & Levier (Apiaceae), Buddleja davi...
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| Veröffentlicht in: | Pharmaceutical biology 2008-01, Vol.46 (9), p.596-601 |
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| creator | Fan, Peihong Hay, Anne-Emmanuelle Marston, Andrew Hostettmann, Kurt |
| description | Abstract
In order to find some medicinal value for invasive neophytes, inhibition of acetylcholinesterase of Reynoutria sachalinensis F. Schmidt ex Maxim. (Polygonaceae), Polygonum cuspidatum Siebold. & Zucc. (Polygonaceae), Heracleum mantegazzianum Sommier & Levier (Apiaceae), Buddleja davidii Franch. (Buddlejaceae), and Ambrosia artemisiifolia L. (Asteraceae) was prescreened by a bioautographic TLC assay. Activity was found in the methanol extract of the leaves of the common ornamental bush B. davidii. Its fractionation by centrifugal partition chromatography led to the isolation of linarin as the most active compound. While extracts of Buddleja nitida Benth. (Buddlejaceae) from Panama were inactive, some constituents were identified on the basis of a comparison with B. davidii by HPLC-MS/MS. Structure-activity relationships of linarin and related flavonoids were investigated. For this purpose, fortunellin and tilianin were prepared by methylation reactions. It appears that the structural elements important for acetylcholinesterase inhibition are not only the 4′ -OMe group, but also the 7-substituted sugar and the pattern of substitution on the B-ring. |
| doi_str_mv | 10.1080/13880200802179592 |
| format | Article |
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In order to find some medicinal value for invasive neophytes, inhibition of acetylcholinesterase of Reynoutria sachalinensis F. Schmidt ex Maxim. (Polygonaceae), Polygonum cuspidatum Siebold. & Zucc. (Polygonaceae), Heracleum mantegazzianum Sommier & Levier (Apiaceae), Buddleja davidii Franch. (Buddlejaceae), and Ambrosia artemisiifolia L. (Asteraceae) was prescreened by a bioautographic TLC assay. Activity was found in the methanol extract of the leaves of the common ornamental bush B. davidii. Its fractionation by centrifugal partition chromatography led to the isolation of linarin as the most active compound. While extracts of Buddleja nitida Benth. (Buddlejaceae) from Panama were inactive, some constituents were identified on the basis of a comparison with B. davidii by HPLC-MS/MS. Structure-activity relationships of linarin and related flavonoids were investigated. For this purpose, fortunellin and tilianin were prepared by methylation reactions. It appears that the structural elements important for acetylcholinesterase inhibition are not only the 4′ -OMe group, but also the 7-substituted sugar and the pattern of substitution on the B-ring.</description><identifier>ISSN: 1388-0209</identifier><identifier>EISSN: 1744-5116</identifier><identifier>DOI: 10.1080/13880200802179592</identifier><language>eng</language><publisher>Informa UK Ltd</publisher><subject>acetylcholinesterase ; Acetylcholinesterase inhibition ; Ambrosia artemisiifolia ; Apiaceae ; Asteraceae ; Biodiversity and Ecology ; Buddleja ; Buddleja davidii ; Buddleja nitida ; Buddlejaceae ; chemical analysis ; chemical constituents of plants ; cholinesterase inhibitors ; Environmental Sciences ; Fallopia japonica ; flavonoids ; fortunellin ; Heracleum ; Heracleum mantegazzianum ; high performance liquid chromatography ; invasive plants ; invasive species ; leaves ; linarin ; mass spectrometry ; ornamental plants ; plant extracts ; Polygonaceae ; Polygonum ; Polygonum cuspidatum ; structure-activity relationships ; thin layer chromatography ; tilianin</subject><ispartof>Pharmaceutical biology, 2008-01, Vol.46 (9), p.596-601</ispartof><rights>2008 Informa UK Ltd 2008</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c439t-dde1a5866ce35c77a02ddb9636f63c773909d98156678631bcb3382c1b7a39773</citedby><cites>FETCH-LOGICAL-c439t-dde1a5866ce35c77a02ddb9636f63c773909d98156678631bcb3382c1b7a39773</cites><orcidid>0000-0001-5538-0934</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.tandfonline.com/doi/pdf/10.1080/13880200802179592$$EPDF$$P50$$Ginformahealthcare$$H</linktopdf><linktohtml>$$Uhttps://www.tandfonline.com/doi/full/10.1080/13880200802179592$$EHTML$$P50$$Ginformahealthcare$$H</linktohtml><link.rule.ids>230,314,776,780,881,27901,27902,59620,60409,61194,61375</link.rule.ids><backlink>$$Uhttps://hal.science/hal-03815345$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Fan, Peihong</creatorcontrib><creatorcontrib>Hay, Anne-Emmanuelle</creatorcontrib><creatorcontrib>Marston, Andrew</creatorcontrib><creatorcontrib>Hostettmann, Kurt</creatorcontrib><title>Acetylcholinesterase-Inhibitory Activity of Linarin from Buddleja davidii, Structure-Activity Relationships of Related Flavonoids, and Chemical Investigation of Buddleja nitida</title><title>Pharmaceutical biology</title><description>Abstract
In order to find some medicinal value for invasive neophytes, inhibition of acetylcholinesterase of Reynoutria sachalinensis F. Schmidt ex Maxim. (Polygonaceae), Polygonum cuspidatum Siebold. & Zucc. (Polygonaceae), Heracleum mantegazzianum Sommier & Levier (Apiaceae), Buddleja davidii Franch. (Buddlejaceae), and Ambrosia artemisiifolia L. (Asteraceae) was prescreened by a bioautographic TLC assay. Activity was found in the methanol extract of the leaves of the common ornamental bush B. davidii. Its fractionation by centrifugal partition chromatography led to the isolation of linarin as the most active compound. While extracts of Buddleja nitida Benth. (Buddlejaceae) from Panama were inactive, some constituents were identified on the basis of a comparison with B. davidii by HPLC-MS/MS. Structure-activity relationships of linarin and related flavonoids were investigated. For this purpose, fortunellin and tilianin were prepared by methylation reactions. It appears that the structural elements important for acetylcholinesterase inhibition are not only the 4′ -OMe group, but also the 7-substituted sugar and the pattern of substitution on the B-ring.</description><subject>acetylcholinesterase</subject><subject>Acetylcholinesterase inhibition</subject><subject>Ambrosia artemisiifolia</subject><subject>Apiaceae</subject><subject>Asteraceae</subject><subject>Biodiversity and Ecology</subject><subject>Buddleja</subject><subject>Buddleja davidii</subject><subject>Buddleja nitida</subject><subject>Buddlejaceae</subject><subject>chemical analysis</subject><subject>chemical constituents of plants</subject><subject>cholinesterase inhibitors</subject><subject>Environmental Sciences</subject><subject>Fallopia japonica</subject><subject>flavonoids</subject><subject>fortunellin</subject><subject>Heracleum</subject><subject>Heracleum mantegazzianum</subject><subject>high performance liquid chromatography</subject><subject>invasive plants</subject><subject>invasive species</subject><subject>leaves</subject><subject>linarin</subject><subject>mass spectrometry</subject><subject>ornamental plants</subject><subject>plant extracts</subject><subject>Polygonaceae</subject><subject>Polygonum</subject><subject>Polygonum cuspidatum</subject><subject>structure-activity relationships</subject><subject>thin layer chromatography</subject><subject>tilianin</subject><issn>1388-0209</issn><issn>1744-5116</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><recordid>eNp9kc-KFDEQxhtRcF19AE_mJAjbmnT6X9DLOLjuwIDguudQk6S3a8gkY5Ie6bfyEc3syIAIe0ql6vt9VVQVxWtG3zPa0w-M9z2taA4r1olGVE-KC9bVddkw1j7Nca6XWSCeFy9i3FJKG86bi-L3Qpk0WzV6i87EZAJEU67ciBtMPsxkoRIeMM3ED2SNDgI6MgS_I58nra3ZAtFwQI14RW5TmFSaginP0HdjIaF3ccR9PFo8JIwm1xYO3nnU8YqA02Q5mh0qsGTlDnkMvH_AjsS5j8OEGl4Wzwaw0bz6-14Wd9dffixvyvW3r6vlYl2qmotUam0YNH3bKsMb1XVAK603ouXt0PL854IKLXrWtG3Xt5xt1IbzvlJs0wEXuX5ZvDv5jmDlPuAOwiw9oLxZrOUxR3mmed0cWNa-PWn3wf-c8vhyh1EZa8EZP0XJRM36tjsK2Umogo8xmOHszKg83lH-d8fMfDox6AYfdvDLB6tlgtn6MARwCqPkj-Ef_8FHAzaNCoKRWz8Fl3f4aPM3J3oAL-E-5F53txVlnLK-5rQX_A_BbsFb</recordid><startdate>20080101</startdate><enddate>20080101</enddate><creator>Fan, Peihong</creator><creator>Hay, Anne-Emmanuelle</creator><creator>Marston, Andrew</creator><creator>Hostettmann, Kurt</creator><general>Informa UK Ltd</general><general>Taylor & Francis</general><scope>FBQ</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0001-5538-0934</orcidid></search><sort><creationdate>20080101</creationdate><title>Acetylcholinesterase-Inhibitory Activity of Linarin from Buddleja davidii, Structure-Activity Relationships of Related Flavonoids, and Chemical Investigation of Buddleja nitida</title><author>Fan, Peihong ; Hay, Anne-Emmanuelle ; Marston, Andrew ; Hostettmann, Kurt</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c439t-dde1a5866ce35c77a02ddb9636f63c773909d98156678631bcb3382c1b7a39773</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>acetylcholinesterase</topic><topic>Acetylcholinesterase inhibition</topic><topic>Ambrosia artemisiifolia</topic><topic>Apiaceae</topic><topic>Asteraceae</topic><topic>Biodiversity and Ecology</topic><topic>Buddleja</topic><topic>Buddleja davidii</topic><topic>Buddleja nitida</topic><topic>Buddlejaceae</topic><topic>chemical analysis</topic><topic>chemical constituents of plants</topic><topic>cholinesterase inhibitors</topic><topic>Environmental Sciences</topic><topic>Fallopia japonica</topic><topic>flavonoids</topic><topic>fortunellin</topic><topic>Heracleum</topic><topic>Heracleum mantegazzianum</topic><topic>high performance liquid chromatography</topic><topic>invasive plants</topic><topic>invasive species</topic><topic>leaves</topic><topic>linarin</topic><topic>mass spectrometry</topic><topic>ornamental plants</topic><topic>plant extracts</topic><topic>Polygonaceae</topic><topic>Polygonum</topic><topic>Polygonum cuspidatum</topic><topic>structure-activity relationships</topic><topic>thin layer chromatography</topic><topic>tilianin</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fan, Peihong</creatorcontrib><creatorcontrib>Hay, Anne-Emmanuelle</creatorcontrib><creatorcontrib>Marston, Andrew</creatorcontrib><creatorcontrib>Hostettmann, Kurt</creatorcontrib><collection>AGRIS</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Pharmaceutical biology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fan, Peihong</au><au>Hay, Anne-Emmanuelle</au><au>Marston, Andrew</au><au>Hostettmann, Kurt</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Acetylcholinesterase-Inhibitory Activity of Linarin from Buddleja davidii, Structure-Activity Relationships of Related Flavonoids, and Chemical Investigation of Buddleja nitida</atitle><jtitle>Pharmaceutical biology</jtitle><date>2008-01-01</date><risdate>2008</risdate><volume>46</volume><issue>9</issue><spage>596</spage><epage>601</epage><pages>596-601</pages><issn>1388-0209</issn><eissn>1744-5116</eissn><abstract>Abstract
In order to find some medicinal value for invasive neophytes, inhibition of acetylcholinesterase of Reynoutria sachalinensis F. Schmidt ex Maxim. (Polygonaceae), Polygonum cuspidatum Siebold. & Zucc. (Polygonaceae), Heracleum mantegazzianum Sommier & Levier (Apiaceae), Buddleja davidii Franch. (Buddlejaceae), and Ambrosia artemisiifolia L. (Asteraceae) was prescreened by a bioautographic TLC assay. Activity was found in the methanol extract of the leaves of the common ornamental bush B. davidii. Its fractionation by centrifugal partition chromatography led to the isolation of linarin as the most active compound. While extracts of Buddleja nitida Benth. (Buddlejaceae) from Panama were inactive, some constituents were identified on the basis of a comparison with B. davidii by HPLC-MS/MS. Structure-activity relationships of linarin and related flavonoids were investigated. For this purpose, fortunellin and tilianin were prepared by methylation reactions. It appears that the structural elements important for acetylcholinesterase inhibition are not only the 4′ -OMe group, but also the 7-substituted sugar and the pattern of substitution on the B-ring.</abstract><pub>Informa UK Ltd</pub><doi>10.1080/13880200802179592</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-5538-0934</orcidid></addata></record> |
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| ispartof | Pharmaceutical biology, 2008-01, Vol.46 (9), p.596-601 |
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| subjects | acetylcholinesterase Acetylcholinesterase inhibition Ambrosia artemisiifolia Apiaceae Asteraceae Biodiversity and Ecology Buddleja Buddleja davidii Buddleja nitida Buddlejaceae chemical analysis chemical constituents of plants cholinesterase inhibitors Environmental Sciences Fallopia japonica flavonoids fortunellin Heracleum Heracleum mantegazzianum high performance liquid chromatography invasive plants invasive species leaves linarin mass spectrometry ornamental plants plant extracts Polygonaceae Polygonum Polygonum cuspidatum structure-activity relationships thin layer chromatography tilianin |
| title | Acetylcholinesterase-Inhibitory Activity of Linarin from Buddleja davidii, Structure-Activity Relationships of Related Flavonoids, and Chemical Investigation of Buddleja nitida |
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