Melampolides from the Leaves of Smallanthus sonchifolius and Their Inhibitory Activity of LPS-Induced Nitric Oxide Production
Two new melampolide-type sesquiterpene lactones, 8β-epoxyangeloyloxy-9α-ethoxy-14-oxo-acanthospermolide (1) and 8β-angeloyloxy-9α-ethoxy-14-oxo-acanthospermolide (2), were isolated from the leaves of yacon [Smallanthus sonchifolia (POEPP. et ENDL.) H. Robinson] along with eleven known melampolides,...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2008/02/01, Vol.56(2), pp.199-202 |
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| creator | Hong, Seong Su Lee, Seon A Han, Xiang Hua Lee, Min Hee Hwang, Ji Sang Park, Jeong Sook Oh, Ki-Wan Han, Kun Lee, Myung Koo Lee, Heesoon Kim, Wook Lee, Dongho Hwang, Bang Yeon |
| description | Two new melampolide-type sesquiterpene lactones, 8β-epoxyangeloyloxy-9α-ethoxy-14-oxo-acanthospermolide (1) and 8β-angeloyloxy-9α-ethoxy-14-oxo-acanthospermolide (2), were isolated from the leaves of yacon [Smallanthus sonchifolia (POEPP. et ENDL.) H. Robinson] along with eleven known melampolides, allo-schkuhriolide (3), enhydrin (4), polymatin A (5), fluctuanin (6), 8β-angeloyloxy-9α-acetoxy-14-oxo-acanthospermolide (7), 8β-angeloyloxy-14-oxo-acanthospermolide (8), 8β-methacryloyloxymelampolid-14-oic acid methyl ester (9), uvedalin (10), polymatin B (11), 8β-tigloyloxymelampolid-14-oic acid methyl ester (12), and sonchifolin (13). Their structures were established on the basis of spectroscopic evidence including 1D- and 2D-NMR experiments. All isolates were evaluated for inhibition of LPS-induced nitric oxide production in murine macrophage RAW 264.7 cells. |
| doi_str_mv | 10.1248/cpb.56.199 |
| format | Article |
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H. Robinson] along with eleven known melampolides, allo-schkuhriolide (3), enhydrin (4), polymatin A (5), fluctuanin (6), 8β-angeloyloxy-9α-acetoxy-14-oxo-acanthospermolide (7), 8β-angeloyloxy-14-oxo-acanthospermolide (8), 8β-methacryloyloxymelampolid-14-oic acid methyl ester (9), uvedalin (10), polymatin B (11), 8β-tigloyloxymelampolid-14-oic acid methyl ester (12), and sonchifolin (13). Their structures were established on the basis of spectroscopic evidence including 1D- and 2D-NMR experiments. All isolates were evaluated for inhibition of LPS-induced nitric oxide production in murine macrophage RAW 264.7 cells.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.56.199</identifier><identifier>PMID: 18239309</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Animals ; Asteraceae ; Asteraceae - chemistry ; Cell Line ; Cell Survival - drug effects ; Chromatography, High Pressure Liquid ; Crystallography, X-Ray ; Lactones - chemistry ; Lactones - pharmacology ; Lipopolysaccharides - antagonists & inhibitors ; Lipopolysaccharides - pharmacology ; Macrophages - drug effects ; Macrophages - metabolism ; melampolide ; Mice ; Models, Molecular ; Nitric Oxide - biosynthesis ; nitric oxide production inhibitor ; Plant Extracts - analysis ; Plant Leaves - chemistry ; sesquiterpene lactone ; Sesquiterpenes - chemistry ; Sesquiterpenes - pharmacology ; Smallanthus ; Smallanthus sonchifolius ; Spectrometry, Mass, Fast Atom Bombardment ; Spectrophotometry, Infrared ; Spectrophotometry, Ultraviolet ; yacon</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2008/02/01, Vol.56(2), pp.199-202</ispartof><rights>2008 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2008</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c502t-d7022dcc389f93112cbeb5b3f721aa2bdcae9eacff7ecd722cbdbd7c15ad9a253</citedby><cites>FETCH-LOGICAL-c502t-d7022dcc389f93112cbeb5b3f721aa2bdcae9eacff7ecd722cbdbd7c15ad9a253</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18239309$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hong, Seong Su</creatorcontrib><creatorcontrib>Lee, Seon A</creatorcontrib><creatorcontrib>Han, Xiang Hua</creatorcontrib><creatorcontrib>Lee, Min Hee</creatorcontrib><creatorcontrib>Hwang, Ji Sang</creatorcontrib><creatorcontrib>Park, Jeong Sook</creatorcontrib><creatorcontrib>Oh, Ki-Wan</creatorcontrib><creatorcontrib>Han, Kun</creatorcontrib><creatorcontrib>Lee, Myung Koo</creatorcontrib><creatorcontrib>Lee, Heesoon</creatorcontrib><creatorcontrib>Kim, Wook</creatorcontrib><creatorcontrib>Lee, Dongho</creatorcontrib><creatorcontrib>Hwang, Bang Yeon</creatorcontrib><title>Melampolides from the Leaves of Smallanthus sonchifolius and Their Inhibitory Activity of LPS-Induced Nitric Oxide Production</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Two new melampolide-type sesquiterpene lactones, 8β-epoxyangeloyloxy-9α-ethoxy-14-oxo-acanthospermolide (1) and 8β-angeloyloxy-9α-ethoxy-14-oxo-acanthospermolide (2), were isolated from the leaves of yacon [Smallanthus sonchifolia (POEPP. et ENDL.) H. Robinson] along with eleven known melampolides, allo-schkuhriolide (3), enhydrin (4), polymatin A (5), fluctuanin (6), 8β-angeloyloxy-9α-acetoxy-14-oxo-acanthospermolide (7), 8β-angeloyloxy-14-oxo-acanthospermolide (8), 8β-methacryloyloxymelampolid-14-oic acid methyl ester (9), uvedalin (10), polymatin B (11), 8β-tigloyloxymelampolid-14-oic acid methyl ester (12), and sonchifolin (13). Their structures were established on the basis of spectroscopic evidence including 1D- and 2D-NMR experiments. All isolates were evaluated for inhibition of LPS-induced nitric oxide production in murine macrophage RAW 264.7 cells.</description><subject>Animals</subject><subject>Asteraceae</subject><subject>Asteraceae - chemistry</subject><subject>Cell Line</subject><subject>Cell Survival - drug effects</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Crystallography, X-Ray</subject><subject>Lactones - chemistry</subject><subject>Lactones - pharmacology</subject><subject>Lipopolysaccharides - antagonists & inhibitors</subject><subject>Lipopolysaccharides - pharmacology</subject><subject>Macrophages - drug effects</subject><subject>Macrophages - metabolism</subject><subject>melampolide</subject><subject>Mice</subject><subject>Models, Molecular</subject><subject>Nitric Oxide - biosynthesis</subject><subject>nitric oxide production inhibitor</subject><subject>Plant Extracts - analysis</subject><subject>Plant Leaves - chemistry</subject><subject>sesquiterpene lactone</subject><subject>Sesquiterpenes - chemistry</subject><subject>Sesquiterpenes - pharmacology</subject><subject>Smallanthus</subject><subject>Smallanthus sonchifolius</subject><subject>Spectrometry, Mass, Fast Atom Bombardment</subject><subject>Spectrophotometry, Infrared</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>yacon</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU2LFDEQhoMo7uzqxR8gAcHDQo_56HQmJ1kWPwZGd2HXc0gn1XaG7s6YpBfn4H83w4wuePGSUKknT1G8CL2iZElZvXpnd-1SNEuq1BO0oLyWlWCMP0ULQoiqGG_4GTpPaUsIE0Ty5-iMrhhXnKgF-vUFBjPuwuAdJNzFMOLcA96AeSh16PDdaIbBTLmfE05hsr3vClwKMzl834OPeD31vvU5xD2-stk_-Lw__Nzc3lXryc0WHP7qc_QW3_wsY_BtDOU1-zC9QM86MyR4ebov0LePH-6vP1ebm0_r66tNZQVhuXKSMOas5SvVKU4psy20ouWdZNQY1jprQIGxXSfBOslK37VOWiqMU4YJfoHeHr27GH7MkLIefbJwWAzCnHTx15KJ1X9BRppGNVIV8M0_4DbMcSpLaFo3pKa8GAt1eaRsDClF6PQu-tHEvaZEH7LTJTstGl2yK_Drk3JuR3CP6CmsArw_AtuUzXf4C5iYvR3gj4sdj6J87PQmapj4b5q8rhU</recordid><startdate>20080201</startdate><enddate>20080201</enddate><creator>Hong, Seong Su</creator><creator>Lee, Seon A</creator><creator>Han, Xiang Hua</creator><creator>Lee, Min Hee</creator><creator>Hwang, Ji Sang</creator><creator>Park, Jeong Sook</creator><creator>Oh, Ki-Wan</creator><creator>Han, Kun</creator><creator>Lee, Myung Koo</creator><creator>Lee, Heesoon</creator><creator>Kim, Wook</creator><creator>Lee, Dongho</creator><creator>Hwang, Bang Yeon</creator><general>The Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</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>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20080201</creationdate><title>Melampolides from the Leaves of Smallanthus sonchifolius and Their Inhibitory Activity of LPS-Induced Nitric Oxide Production</title><author>Hong, Seong Su ; Lee, Seon A ; Han, Xiang Hua ; Lee, Min Hee ; Hwang, Ji Sang ; Park, Jeong Sook ; Oh, Ki-Wan ; Han, Kun ; Lee, Myung Koo ; Lee, Heesoon ; Kim, Wook ; Lee, Dongho ; Hwang, Bang Yeon</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c502t-d7022dcc389f93112cbeb5b3f721aa2bdcae9eacff7ecd722cbdbd7c15ad9a253</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Animals</topic><topic>Asteraceae</topic><topic>Asteraceae - chemistry</topic><topic>Cell Line</topic><topic>Cell Survival - drug effects</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Crystallography, X-Ray</topic><topic>Lactones - chemistry</topic><topic>Lactones - pharmacology</topic><topic>Lipopolysaccharides - antagonists & inhibitors</topic><topic>Lipopolysaccharides - pharmacology</topic><topic>Macrophages - drug effects</topic><topic>Macrophages - metabolism</topic><topic>melampolide</topic><topic>Mice</topic><topic>Models, Molecular</topic><topic>Nitric Oxide - biosynthesis</topic><topic>nitric oxide production inhibitor</topic><topic>Plant Extracts - analysis</topic><topic>Plant Leaves - chemistry</topic><topic>sesquiterpene lactone</topic><topic>Sesquiterpenes - chemistry</topic><topic>Sesquiterpenes - pharmacology</topic><topic>Smallanthus</topic><topic>Smallanthus sonchifolius</topic><topic>Spectrometry, Mass, Fast Atom Bombardment</topic><topic>Spectrophotometry, Infrared</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>yacon</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hong, Seong Su</creatorcontrib><creatorcontrib>Lee, Seon A</creatorcontrib><creatorcontrib>Han, Xiang Hua</creatorcontrib><creatorcontrib>Lee, Min Hee</creatorcontrib><creatorcontrib>Hwang, Ji Sang</creatorcontrib><creatorcontrib>Park, Jeong Sook</creatorcontrib><creatorcontrib>Oh, Ki-Wan</creatorcontrib><creatorcontrib>Han, Kun</creatorcontrib><creatorcontrib>Lee, Myung Koo</creatorcontrib><creatorcontrib>Lee, Heesoon</creatorcontrib><creatorcontrib>Kim, Wook</creatorcontrib><creatorcontrib>Lee, Dongho</creatorcontrib><creatorcontrib>Hwang, Bang Yeon</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hong, Seong Su</au><au>Lee, Seon A</au><au>Han, Xiang Hua</au><au>Lee, Min Hee</au><au>Hwang, Ji Sang</au><au>Park, Jeong Sook</au><au>Oh, Ki-Wan</au><au>Han, Kun</au><au>Lee, Myung Koo</au><au>Lee, Heesoon</au><au>Kim, Wook</au><au>Lee, Dongho</au><au>Hwang, Bang Yeon</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Melampolides from the Leaves of Smallanthus sonchifolius and Their Inhibitory Activity of LPS-Induced Nitric Oxide Production</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2008-02-01</date><risdate>2008</risdate><volume>56</volume><issue>2</issue><spage>199</spage><epage>202</epage><pages>199-202</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>Two new melampolide-type sesquiterpene lactones, 8β-epoxyangeloyloxy-9α-ethoxy-14-oxo-acanthospermolide (1) and 8β-angeloyloxy-9α-ethoxy-14-oxo-acanthospermolide (2), were isolated from the leaves of yacon [Smallanthus sonchifolia (POEPP. et ENDL.) H. Robinson] along with eleven known melampolides, allo-schkuhriolide (3), enhydrin (4), polymatin A (5), fluctuanin (6), 8β-angeloyloxy-9α-acetoxy-14-oxo-acanthospermolide (7), 8β-angeloyloxy-14-oxo-acanthospermolide (8), 8β-methacryloyloxymelampolid-14-oic acid methyl ester (9), uvedalin (10), polymatin B (11), 8β-tigloyloxymelampolid-14-oic acid methyl ester (12), and sonchifolin (13). Their structures were established on the basis of spectroscopic evidence including 1D- and 2D-NMR experiments. All isolates were evaluated for inhibition of LPS-induced nitric oxide production in murine macrophage RAW 264.7 cells.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>18239309</pmid><doi>10.1248/cpb.56.199</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Chemical and Pharmaceutical Bulletin, 2008/02/01, Vol.56(2), pp.199-202 |
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| source | MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese; Free Full-Text Journals in Chemistry |
| subjects | Animals Asteraceae Asteraceae - chemistry Cell Line Cell Survival - drug effects Chromatography, High Pressure Liquid Crystallography, X-Ray Lactones - chemistry Lactones - pharmacology Lipopolysaccharides - antagonists & inhibitors Lipopolysaccharides - pharmacology Macrophages - drug effects Macrophages - metabolism melampolide Mice Models, Molecular Nitric Oxide - biosynthesis nitric oxide production inhibitor Plant Extracts - analysis Plant Leaves - chemistry sesquiterpene lactone Sesquiterpenes - chemistry Sesquiterpenes - pharmacology Smallanthus Smallanthus sonchifolius Spectrometry, Mass, Fast Atom Bombardment Spectrophotometry, Infrared Spectrophotometry, Ultraviolet yacon |
| title | Melampolides from the Leaves of Smallanthus sonchifolius and Their Inhibitory Activity of LPS-Induced Nitric Oxide Production |
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