iNOS Inhibitory Activity of Sesquiterpenoids and a Monoterpenoid from the Rhizomes of Curcuma wenyujin
Eleven new sesquiterpenoids, wenyujinins A–K (1–11), and a new monoterpenoid, wenyujinin L (12), were isolated from the rhizomes of Curcuma wenyujin. Their structures and relative configurations were elucidated using 1D and 2D NMR, X-ray crystallographic analysis, and HRESIMS data. The absolute conf...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2014-10, Vol.77 (10), p.2161-2169 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Yin, Guo-Ping Li, Liang-Chun Zhang, Qing-Zhe An, Yue-Wei Zhu, Jing-Jing Wang, Zhi-Min Chou, Gui-Xin Wang, Zheng-tao |
| description | Eleven new sesquiterpenoids, wenyujinins A–K (1–11), and a new monoterpenoid, wenyujinin L (12), were isolated from the rhizomes of Curcuma wenyujin. Their structures and relative configurations were elucidated using 1D and 2D NMR, X-ray crystallographic analysis, and HRESIMS data. The absolute configurations of 1, 2, 3, 4, 6, 8, 9, and 10 were determined by comparison of the experimental and calculated ECD spectra. The absolute configuration of 5 was determined from the ECD data of the [Rh2(OCOCF3)4] complex, whereas those of 7 and 12 were determined from the ECD spectra of the compounds alone. Compounds 7 and 7a strongly inhibited the induction of NO production by LPS, with IC50 values of 7.6 and 8.5 μM, respectively. Compounds 6 and 10 moderately inhibited NO production with IC50 values of 47.7 and 48.6 μM, respectively. |
| doi_str_mv | 10.1021/np400984c |
| format | Article |
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Their structures and relative configurations were elucidated using 1D and 2D NMR, X-ray crystallographic analysis, and HRESIMS data. The absolute configurations of 1, 2, 3, 4, 6, 8, 9, and 10 were determined by comparison of the experimental and calculated ECD spectra. The absolute configuration of 5 was determined from the ECD data of the [Rh2(OCOCF3)4] complex, whereas those of 7 and 12 were determined from the ECD spectra of the compounds alone. Compounds 7 and 7a strongly inhibited the induction of NO production by LPS, with IC50 values of 7.6 and 8.5 μM, respectively. Compounds 6 and 10 moderately inhibited NO production with IC50 values of 47.7 and 48.6 μM, respectively.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np400984c</identifier><identifier>PMID: 25275213</identifier><language>eng</language><publisher>United States: American Chemical Society and American Society of Pharmacognosy</publisher><subject>Animals ; Crystallography, X-Ray ; Curcuma - chemistry ; Drugs, Chinese Herbal - chemistry ; Drugs, Chinese Herbal - isolation & purification ; Drugs, Chinese Herbal - pharmacology ; Inhibitory Concentration 50 ; Lipopolysaccharides - pharmacology ; Macrophages, Peritoneal - drug effects ; Mice ; Molecular Structure ; Monoterpenes - chemistry ; Monoterpenes - isolation & purification ; Monoterpenes - pharmacology ; Nitric Oxide - biosynthesis ; Nitric Oxide Synthase Type II - antagonists & inhibitors ; Nuclear Magnetic Resonance, Biomolecular ; Rhizome - chemistry ; Sesquiterpenes - chemistry ; Sesquiterpenes - isolation & purification ; Sesquiterpenes - pharmacology</subject><ispartof>Journal of natural products (Washington, D.C.), 2014-10, Vol.77 (10), p.2161-2169</ispartof><rights>Copyright © 2014 American Chemical Society and American Society of Pharmacognosy</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-66950a7ee47f571986be7aec4ad4c2e81becb34ba3ab9df64fa8143a0bd6e24e3</citedby><cites>FETCH-LOGICAL-a381t-66950a7ee47f571986be7aec4ad4c2e81becb34ba3ab9df64fa8143a0bd6e24e3</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/np400984c$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np400984c$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25275213$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yin, Guo-Ping</creatorcontrib><creatorcontrib>Li, Liang-Chun</creatorcontrib><creatorcontrib>Zhang, Qing-Zhe</creatorcontrib><creatorcontrib>An, Yue-Wei</creatorcontrib><creatorcontrib>Zhu, Jing-Jing</creatorcontrib><creatorcontrib>Wang, Zhi-Min</creatorcontrib><creatorcontrib>Chou, Gui-Xin</creatorcontrib><creatorcontrib>Wang, Zheng-tao</creatorcontrib><title>iNOS Inhibitory Activity of Sesquiterpenoids and a Monoterpenoid from the Rhizomes of Curcuma wenyujin</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Eleven new sesquiterpenoids, wenyujinins A–K (1–11), and a new monoterpenoid, wenyujinin L (12), were isolated from the rhizomes of Curcuma wenyujin. Their structures and relative configurations were elucidated using 1D and 2D NMR, X-ray crystallographic analysis, and HRESIMS data. The absolute configurations of 1, 2, 3, 4, 6, 8, 9, and 10 were determined by comparison of the experimental and calculated ECD spectra. The absolute configuration of 5 was determined from the ECD data of the [Rh2(OCOCF3)4] complex, whereas those of 7 and 12 were determined from the ECD spectra of the compounds alone. Compounds 7 and 7a strongly inhibited the induction of NO production by LPS, with IC50 values of 7.6 and 8.5 μM, respectively. Compounds 6 and 10 moderately inhibited NO production with IC50 values of 47.7 and 48.6 μM, respectively.</description><subject>Animals</subject><subject>Crystallography, X-Ray</subject><subject>Curcuma - chemistry</subject><subject>Drugs, Chinese Herbal - chemistry</subject><subject>Drugs, Chinese Herbal - isolation & purification</subject><subject>Drugs, Chinese Herbal - pharmacology</subject><subject>Inhibitory Concentration 50</subject><subject>Lipopolysaccharides - pharmacology</subject><subject>Macrophages, Peritoneal - drug effects</subject><subject>Mice</subject><subject>Molecular Structure</subject><subject>Monoterpenes - chemistry</subject><subject>Monoterpenes - isolation & purification</subject><subject>Monoterpenes - pharmacology</subject><subject>Nitric Oxide - biosynthesis</subject><subject>Nitric Oxide Synthase Type II - antagonists & inhibitors</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>Rhizome - chemistry</subject><subject>Sesquiterpenes - chemistry</subject><subject>Sesquiterpenes - isolation & purification</subject><subject>Sesquiterpenes - pharmacology</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkM9LwzAUgIMobk4P_gOSi6CH6kuTpu1Rhj8G04HTc0nTV5axJlvSKvOvd2NzJ08PHt_74H2EXDK4YxCze7sUAHkm9BHpsySGSEKcHJM-MMkjnknRI2chzAGAQ56ckl6cxGkSM94ntXmbTOnIzkxpWufX9EG35su0a-pqOsWw6kyLfonWmSpQZSuq6Kuz7rCktXcNbWdI32fmxzUYtpfDzuuuUfQb7bqbG3tOTmq1CHixnwPy-fT4MXyJxpPn0fBhHCmesTaSMk9ApYgirZOU5ZksMVWohaqEjjFjJeqSi1JxVeZVLUWtMia4grKSGAvkA3Kz8y69W3UY2qIxQeNioSy6LhRMMikyAAYb9HaHau9C8FgXS28a5dcFg2KbtThk3bBXe21XNlgdyL-OG-B6BygdirnrvN18-Y_oFymRgGQ</recordid><startdate>20141024</startdate><enddate>20141024</enddate><creator>Yin, Guo-Ping</creator><creator>Li, Liang-Chun</creator><creator>Zhang, Qing-Zhe</creator><creator>An, Yue-Wei</creator><creator>Zhu, Jing-Jing</creator><creator>Wang, Zhi-Min</creator><creator>Chou, Gui-Xin</creator><creator>Wang, Zheng-tao</creator><general>American Chemical Society and American Society of Pharmacognosy</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>20141024</creationdate><title>iNOS Inhibitory Activity of Sesquiterpenoids and a Monoterpenoid from the Rhizomes of Curcuma wenyujin</title><author>Yin, Guo-Ping ; Li, Liang-Chun ; Zhang, Qing-Zhe ; An, Yue-Wei ; Zhu, Jing-Jing ; Wang, Zhi-Min ; Chou, Gui-Xin ; Wang, Zheng-tao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-66950a7ee47f571986be7aec4ad4c2e81becb34ba3ab9df64fa8143a0bd6e24e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Animals</topic><topic>Crystallography, X-Ray</topic><topic>Curcuma - chemistry</topic><topic>Drugs, Chinese Herbal - chemistry</topic><topic>Drugs, Chinese Herbal - isolation & purification</topic><topic>Drugs, Chinese Herbal - pharmacology</topic><topic>Inhibitory Concentration 50</topic><topic>Lipopolysaccharides - pharmacology</topic><topic>Macrophages, Peritoneal - drug effects</topic><topic>Mice</topic><topic>Molecular Structure</topic><topic>Monoterpenes - chemistry</topic><topic>Monoterpenes - isolation & purification</topic><topic>Monoterpenes - pharmacology</topic><topic>Nitric Oxide - biosynthesis</topic><topic>Nitric Oxide Synthase Type II - antagonists & inhibitors</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>Rhizome - chemistry</topic><topic>Sesquiterpenes - chemistry</topic><topic>Sesquiterpenes - isolation & purification</topic><topic>Sesquiterpenes - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yin, Guo-Ping</creatorcontrib><creatorcontrib>Li, Liang-Chun</creatorcontrib><creatorcontrib>Zhang, Qing-Zhe</creatorcontrib><creatorcontrib>An, Yue-Wei</creatorcontrib><creatorcontrib>Zhu, Jing-Jing</creatorcontrib><creatorcontrib>Wang, Zhi-Min</creatorcontrib><creatorcontrib>Chou, Gui-Xin</creatorcontrib><creatorcontrib>Wang, Zheng-tao</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>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yin, Guo-Ping</au><au>Li, Liang-Chun</au><au>Zhang, Qing-Zhe</au><au>An, Yue-Wei</au><au>Zhu, Jing-Jing</au><au>Wang, Zhi-Min</au><au>Chou, Gui-Xin</au><au>Wang, Zheng-tao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>iNOS Inhibitory Activity of Sesquiterpenoids and a Monoterpenoid from the Rhizomes of Curcuma wenyujin</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>2014-10-24</date><risdate>2014</risdate><volume>77</volume><issue>10</issue><spage>2161</spage><epage>2169</epage><pages>2161-2169</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>Eleven new sesquiterpenoids, wenyujinins A–K (1–11), and a new monoterpenoid, wenyujinin L (12), were isolated from the rhizomes of Curcuma wenyujin. Their structures and relative configurations were elucidated using 1D and 2D NMR, X-ray crystallographic analysis, and HRESIMS data. The absolute configurations of 1, 2, 3, 4, 6, 8, 9, and 10 were determined by comparison of the experimental and calculated ECD spectra. The absolute configuration of 5 was determined from the ECD data of the [Rh2(OCOCF3)4] complex, whereas those of 7 and 12 were determined from the ECD spectra of the compounds alone. Compounds 7 and 7a strongly inhibited the induction of NO production by LPS, with IC50 values of 7.6 and 8.5 μM, respectively. Compounds 6 and 10 moderately inhibited NO production with IC50 values of 47.7 and 48.6 μM, respectively.</abstract><cop>United States</cop><pub>American Chemical Society and American Society of Pharmacognosy</pub><pmid>25275213</pmid><doi>10.1021/np400984c</doi><tpages>9</tpages></addata></record> |
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| subjects | Animals Crystallography, X-Ray Curcuma - chemistry Drugs, Chinese Herbal - chemistry Drugs, Chinese Herbal - isolation & purification Drugs, Chinese Herbal - pharmacology Inhibitory Concentration 50 Lipopolysaccharides - pharmacology Macrophages, Peritoneal - drug effects Mice Molecular Structure Monoterpenes - chemistry Monoterpenes - isolation & purification Monoterpenes - pharmacology Nitric Oxide - biosynthesis Nitric Oxide Synthase Type II - antagonists & inhibitors Nuclear Magnetic Resonance, Biomolecular Rhizome - chemistry Sesquiterpenes - chemistry Sesquiterpenes - isolation & purification Sesquiterpenes - pharmacology |
| title | iNOS Inhibitory Activity of Sesquiterpenoids and a Monoterpenoid from the Rhizomes of Curcuma wenyujin |
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