Anti-inflammatory norditerpenoids from the soft coral Sinularia maxima
Two new norditerpenoids, 12-hydroxy-scabrolide A (2), 13-epi-scabrolide C (6) and five know compounds (1, 3–5, 7) were isolated from the methanol extract of the soft coral Sinularia maxima. They were evaluated for inhibitory effects on lipopolysaccharide-stimulated production of pro-inflammatory cyt...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2013-01, Vol.23 (1), p.228-231 |
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| creator | Thao, Nguyen Phuong Nam, Nguyen Hoai Cuong, Nguyen Xuan Quang, Tran Hong Tung, Pham The Dat, Le Duc Chae, Doobyeong Kim, Sohyun Koh, Young-Sang Kiem, Phan Van Minh, Chau Van Kim, Young Ho |
| description | Two new norditerpenoids, 12-hydroxy-scabrolide A (2), 13-epi-scabrolide C (6) and five know compounds (1, 3–5, 7) were isolated from the methanol extract of the soft coral Sinularia maxima. They were evaluated for inhibitory effects on lipopolysaccharide-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells (BMDCs). Compound 6 potently inhibited IL-12 and IL-6 production in LPS-stimulated bone marrow derived dendritic with IC50 values ranging from 5.30±0.21 to 13.12±0.64μM. Compound 1 exhibited moderate inhibitory activity against IL-12 and IL-6 production with IC50 values ranging from 23.52±1.37 to 69.85±4.11μM.
Chemical investigation of the soft coral Sinularia maxima resulted in the isolation of seven norditerpenoids, including two new compounds, 12-hydroxy-scabrolide A (2) and 13-epi-scabrolide C (6). The structures of the isolated compounds were elucidated based on extensive spectroscopic evidence including Fourier transform ion cyclotron resonance mass spectrometry (FTICR-MS) and both one- and two-dimensional nuclear magnetic resonance (1D and 2D NMR, respectively), in comparison with reported data. Compound 6 potently inhibited IL-12 and IL-6 production in LPS-stimulated bone marrow derived dendritic (BMDCs) with IC50 values of 5.30±0.21 and 13.12±0.64μM, respectively. Compound 1 exhibited moderate inhibitory activity against IL-12 and IL-6 production with IC50 values of 23.52±1.37 and 69.85±4.11μM, respectively. |
| doi_str_mv | 10.1016/j.bmcl.2012.10.129 |
| format | Article |
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Chemical investigation of the soft coral Sinularia maxima resulted in the isolation of seven norditerpenoids, including two new compounds, 12-hydroxy-scabrolide A (2) and 13-epi-scabrolide C (6). The structures of the isolated compounds were elucidated based on extensive spectroscopic evidence including Fourier transform ion cyclotron resonance mass spectrometry (FTICR-MS) and both one- and two-dimensional nuclear magnetic resonance (1D and 2D NMR, respectively), in comparison with reported data. Compound 6 potently inhibited IL-12 and IL-6 production in LPS-stimulated bone marrow derived dendritic (BMDCs) with IC50 values of 5.30±0.21 and 13.12±0.64μM, respectively. Compound 1 exhibited moderate inhibitory activity against IL-12 and IL-6 production with IC50 values of 23.52±1.37 and 69.85±4.11μM, respectively.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2012.10.129</identifier><identifier>PMID: 23200246</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>12-Hydroxy-scabrolide A ; 13-epi-Scabrolide C ; Animals ; Anthozoa - chemistry ; Anti-inflammatory activity ; Anti-Inflammatory Agents - chemistry ; Anti-Inflammatory Agents - isolation & purification ; Anti-Inflammatory Agents - pharmacology ; Bone Marrow Cells - cytology ; Cells, Cultured ; Dendritic Cells - cytology ; Dendritic Cells - drug effects ; Diterpenes - chemistry ; Diterpenes - isolation & purification ; Diterpenes - pharmacology ; Interleukin-12 - metabolism ; Interleukin-6 - metabolism ; Lactones - chemistry ; Lactones - isolation & purification ; Lactones - pharmacology ; Lipopolysaccharides - toxicity ; Magnetic Resonance Spectroscopy ; Mice ; Mice, Inbred C57BL ; Molecular Conformation ; Norditerpenoid ; Sinularia maxima ; Soft coral ; Stereoisomerism</subject><ispartof>Bioorganic & medicinal chemistry letters, 2013-01, Vol.23 (1), p.228-231</ispartof><rights>2012 Elsevier Ltd</rights><rights>Copyright © 2012 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-23f0529ea080eba4dee4d6e7fc029981e17ac140a121726253e7e5f22eac870b3</citedby><cites>FETCH-LOGICAL-c356t-23f0529ea080eba4dee4d6e7fc029981e17ac140a121726253e7e5f22eac870b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X1201431X$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23200246$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Thao, Nguyen Phuong</creatorcontrib><creatorcontrib>Nam, Nguyen Hoai</creatorcontrib><creatorcontrib>Cuong, Nguyen Xuan</creatorcontrib><creatorcontrib>Quang, Tran Hong</creatorcontrib><creatorcontrib>Tung, Pham The</creatorcontrib><creatorcontrib>Dat, Le Duc</creatorcontrib><creatorcontrib>Chae, Doobyeong</creatorcontrib><creatorcontrib>Kim, Sohyun</creatorcontrib><creatorcontrib>Koh, Young-Sang</creatorcontrib><creatorcontrib>Kiem, Phan Van</creatorcontrib><creatorcontrib>Minh, Chau Van</creatorcontrib><creatorcontrib>Kim, Young Ho</creatorcontrib><title>Anti-inflammatory norditerpenoids from the soft coral Sinularia maxima</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Two new norditerpenoids, 12-hydroxy-scabrolide A (2), 13-epi-scabrolide C (6) and five know compounds (1, 3–5, 7) were isolated from the methanol extract of the soft coral Sinularia maxima. They were evaluated for inhibitory effects on lipopolysaccharide-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells (BMDCs). Compound 6 potently inhibited IL-12 and IL-6 production in LPS-stimulated bone marrow derived dendritic with IC50 values ranging from 5.30±0.21 to 13.12±0.64μM. Compound 1 exhibited moderate inhibitory activity against IL-12 and IL-6 production with IC50 values ranging from 23.52±1.37 to 69.85±4.11μM.
Chemical investigation of the soft coral Sinularia maxima resulted in the isolation of seven norditerpenoids, including two new compounds, 12-hydroxy-scabrolide A (2) and 13-epi-scabrolide C (6). The structures of the isolated compounds were elucidated based on extensive spectroscopic evidence including Fourier transform ion cyclotron resonance mass spectrometry (FTICR-MS) and both one- and two-dimensional nuclear magnetic resonance (1D and 2D NMR, respectively), in comparison with reported data. Compound 6 potently inhibited IL-12 and IL-6 production in LPS-stimulated bone marrow derived dendritic (BMDCs) with IC50 values of 5.30±0.21 and 13.12±0.64μM, respectively. Compound 1 exhibited moderate inhibitory activity against IL-12 and IL-6 production with IC50 values of 23.52±1.37 and 69.85±4.11μM, respectively.</description><subject>12-Hydroxy-scabrolide A</subject><subject>13-epi-Scabrolide C</subject><subject>Animals</subject><subject>Anthozoa - chemistry</subject><subject>Anti-inflammatory activity</subject><subject>Anti-Inflammatory Agents - chemistry</subject><subject>Anti-Inflammatory Agents - isolation & purification</subject><subject>Anti-Inflammatory Agents - pharmacology</subject><subject>Bone Marrow Cells - cytology</subject><subject>Cells, Cultured</subject><subject>Dendritic Cells - cytology</subject><subject>Dendritic Cells - drug effects</subject><subject>Diterpenes - chemistry</subject><subject>Diterpenes - isolation & purification</subject><subject>Diterpenes - pharmacology</subject><subject>Interleukin-12 - metabolism</subject><subject>Interleukin-6 - metabolism</subject><subject>Lactones - chemistry</subject><subject>Lactones - isolation & purification</subject><subject>Lactones - pharmacology</subject><subject>Lipopolysaccharides - toxicity</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mice</subject><subject>Mice, Inbred C57BL</subject><subject>Molecular Conformation</subject><subject>Norditerpenoid</subject><subject>Sinularia maxima</subject><subject>Soft coral</subject><subject>Stereoisomerism</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kEFLw0AQhRdRbK3-AQ-So5fE2ckmacBLKVaFggcVvC2bzQS3JNm6m4j99ya2evQ08Pje481j7JJDxIGnN5uoaHQdIXCMRg3zIzblIhVhLCA5ZlPIUwjnuXibsDPvNwBcgBCnbIIxAqBIp2y1aDsTmraqVdOozrpd0FpXmo7cllprSh9UzjZB906Bt1UXaOtUHTybtq-VMypo1Jdp1Dk7qVTt6eJwZ-x1dfeyfAjXT_ePy8U61HGSdiHGFSSYk4I5UKFESSTKlLJKA-b5nBPPlB5KKo48wxSTmDJKKkRSep5BEc_Y9T536-xHT76TjfGa6lq1ZHsvOQrIgfNYDCjuUe2s944quXVDU7eTHOS4n9zIcT857vejYT6Yrg75fdFQ-Wf5HWwAbvcADV9-GnLSa0OtptI40p0srfkv_xtLAoFO</recordid><startdate>20130101</startdate><enddate>20130101</enddate><creator>Thao, Nguyen Phuong</creator><creator>Nam, Nguyen Hoai</creator><creator>Cuong, Nguyen Xuan</creator><creator>Quang, Tran Hong</creator><creator>Tung, Pham The</creator><creator>Dat, Le Duc</creator><creator>Chae, Doobyeong</creator><creator>Kim, Sohyun</creator><creator>Koh, Young-Sang</creator><creator>Kiem, Phan Van</creator><creator>Minh, Chau Van</creator><creator>Kim, Young Ho</creator><general>Elsevier Ltd</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></search><sort><creationdate>20130101</creationdate><title>Anti-inflammatory norditerpenoids from the soft coral Sinularia maxima</title><author>Thao, Nguyen Phuong ; Nam, Nguyen Hoai ; Cuong, Nguyen Xuan ; Quang, Tran Hong ; Tung, Pham The ; Dat, Le Duc ; Chae, Doobyeong ; Kim, Sohyun ; Koh, Young-Sang ; Kiem, Phan Van ; Minh, Chau Van ; Kim, Young Ho</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-23f0529ea080eba4dee4d6e7fc029981e17ac140a121726253e7e5f22eac870b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>12-Hydroxy-scabrolide A</topic><topic>13-epi-Scabrolide C</topic><topic>Animals</topic><topic>Anthozoa - chemistry</topic><topic>Anti-inflammatory activity</topic><topic>Anti-Inflammatory Agents - chemistry</topic><topic>Anti-Inflammatory Agents - isolation & purification</topic><topic>Anti-Inflammatory Agents - pharmacology</topic><topic>Bone Marrow Cells - cytology</topic><topic>Cells, Cultured</topic><topic>Dendritic Cells - cytology</topic><topic>Dendritic Cells - drug effects</topic><topic>Diterpenes - chemistry</topic><topic>Diterpenes - isolation & purification</topic><topic>Diterpenes - pharmacology</topic><topic>Interleukin-12 - metabolism</topic><topic>Interleukin-6 - metabolism</topic><topic>Lactones - chemistry</topic><topic>Lactones - isolation & purification</topic><topic>Lactones - pharmacology</topic><topic>Lipopolysaccharides - toxicity</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mice</topic><topic>Mice, Inbred C57BL</topic><topic>Molecular Conformation</topic><topic>Norditerpenoid</topic><topic>Sinularia maxima</topic><topic>Soft coral</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Thao, Nguyen Phuong</creatorcontrib><creatorcontrib>Nam, Nguyen Hoai</creatorcontrib><creatorcontrib>Cuong, Nguyen Xuan</creatorcontrib><creatorcontrib>Quang, Tran Hong</creatorcontrib><creatorcontrib>Tung, Pham The</creatorcontrib><creatorcontrib>Dat, Le Duc</creatorcontrib><creatorcontrib>Chae, Doobyeong</creatorcontrib><creatorcontrib>Kim, Sohyun</creatorcontrib><creatorcontrib>Koh, Young-Sang</creatorcontrib><creatorcontrib>Kiem, Phan Van</creatorcontrib><creatorcontrib>Minh, Chau Van</creatorcontrib><creatorcontrib>Kim, Young Ho</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>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Thao, Nguyen Phuong</au><au>Nam, Nguyen Hoai</au><au>Cuong, Nguyen Xuan</au><au>Quang, Tran Hong</au><au>Tung, Pham The</au><au>Dat, Le Duc</au><au>Chae, Doobyeong</au><au>Kim, Sohyun</au><au>Koh, Young-Sang</au><au>Kiem, Phan Van</au><au>Minh, Chau Van</au><au>Kim, Young Ho</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Anti-inflammatory norditerpenoids from the soft coral Sinularia maxima</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2013-01-01</date><risdate>2013</risdate><volume>23</volume><issue>1</issue><spage>228</spage><epage>231</epage><pages>228-231</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Two new norditerpenoids, 12-hydroxy-scabrolide A (2), 13-epi-scabrolide C (6) and five know compounds (1, 3–5, 7) were isolated from the methanol extract of the soft coral Sinularia maxima. They were evaluated for inhibitory effects on lipopolysaccharide-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells (BMDCs). Compound 6 potently inhibited IL-12 and IL-6 production in LPS-stimulated bone marrow derived dendritic with IC50 values ranging from 5.30±0.21 to 13.12±0.64μM. Compound 1 exhibited moderate inhibitory activity against IL-12 and IL-6 production with IC50 values ranging from 23.52±1.37 to 69.85±4.11μM.
Chemical investigation of the soft coral Sinularia maxima resulted in the isolation of seven norditerpenoids, including two new compounds, 12-hydroxy-scabrolide A (2) and 13-epi-scabrolide C (6). The structures of the isolated compounds were elucidated based on extensive spectroscopic evidence including Fourier transform ion cyclotron resonance mass spectrometry (FTICR-MS) and both one- and two-dimensional nuclear magnetic resonance (1D and 2D NMR, respectively), in comparison with reported data. Compound 6 potently inhibited IL-12 and IL-6 production in LPS-stimulated bone marrow derived dendritic (BMDCs) with IC50 values of 5.30±0.21 and 13.12±0.64μM, respectively. Compound 1 exhibited moderate inhibitory activity against IL-12 and IL-6 production with IC50 values of 23.52±1.37 and 69.85±4.11μM, respectively.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>23200246</pmid><doi>10.1016/j.bmcl.2012.10.129</doi><tpages>4</tpages></addata></record> |
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| subjects | 12-Hydroxy-scabrolide A 13-epi-Scabrolide C Animals Anthozoa - chemistry Anti-inflammatory activity Anti-Inflammatory Agents - chemistry Anti-Inflammatory Agents - isolation & purification Anti-Inflammatory Agents - pharmacology Bone Marrow Cells - cytology Cells, Cultured Dendritic Cells - cytology Dendritic Cells - drug effects Diterpenes - chemistry Diterpenes - isolation & purification Diterpenes - pharmacology Interleukin-12 - metabolism Interleukin-6 - metabolism Lactones - chemistry Lactones - isolation & purification Lactones - pharmacology Lipopolysaccharides - toxicity Magnetic Resonance Spectroscopy Mice Mice, Inbred C57BL Molecular Conformation Norditerpenoid Sinularia maxima Soft coral Stereoisomerism |
| title | Anti-inflammatory norditerpenoids from the soft coral Sinularia maxima |
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