New Verticillane Diterpenoids from Cespitularia taeniata
Chemical investigation of Cespitularia taeniata has led to the isolation of three new verticillanes, cespitulins E–G (1–3, resp.). The structures of these compounds were elucidated by spectroscopic analysis, especially HR‐MS and 2D‐NMR techniques. Compound 1 possesses a rare norverticillane skeleton...
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| Veröffentlicht in: | Chemistry & biodiversity 2012-03, Vol.9 (3), p.654-661 |
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| container_title | Chemistry & biodiversity |
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| creator | Chang, Jiun-Yang Fazary, Ahmed Eid Lin, Yu-Chi Hwang, Tsong-Long Shen, Ya-Ching |
| description | Chemical investigation of Cespitularia taeniata has led to the isolation of three new verticillanes, cespitulins E–G (1–3, resp.). The structures of these compounds were elucidated by spectroscopic analysis, especially HR‐MS and 2D‐NMR techniques. Compound 1 possesses a rare norverticillane skeleton with two adjacent OH groups at C(5) and C(6), while the seco‐compound 2 with an aldehyde group at C(9) results from an unusual bond cleavage between C(9) and C(10). Pharmacological studies revealed that compound 3 exhibited significant activities on superoxide‐anion generation and elastase release by human neutrophils in response to FMLP/CB. A plausible biogenetic pathway for compound 2 is also discussed. |
| doi_str_mv | 10.1002/cbdv.201100122 |
| format | Article |
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The structures of these compounds were elucidated by spectroscopic analysis, especially HR‐MS and 2D‐NMR techniques. Compound 1 possesses a rare norverticillane skeleton with two adjacent OH groups at C(5) and C(6), while the seco‐compound 2 with an aldehyde group at C(9) results from an unusual bond cleavage between C(9) and C(10). Pharmacological studies revealed that compound 3 exhibited significant activities on superoxide‐anion generation and elastase release by human neutrophils in response to FMLP/CB. A plausible biogenetic pathway for compound 2 is also discussed.</description><identifier>ISSN: 1612-1872</identifier><identifier>EISSN: 1612-1880</identifier><identifier>DOI: 10.1002/cbdv.201100122</identifier><identifier>PMID: 22422532</identifier><language>eng</language><publisher>Zürich: WILEY-VCH Verlag</publisher><subject>Animals ; Anthozoa - chemistry ; Anti-inflammatory activity ; Cespitularia taeniata ; Cespitulins E - G ; Diterpenes - chemistry ; Diterpenes - isolation & purification ; Diterpenes - pharmacology ; Diterpenoids ; Humans ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Molecular Conformation ; Neutrophils - drug effects ; Neutrophils - metabolism ; Pancreatic Elastase - metabolism ; Soft corals ; Superoxides - metabolism ; Verticillane diterpenoids</subject><ispartof>Chemistry & biodiversity, 2012-03, Vol.9 (3), p.654-661</ispartof><rights>Copyright © 2012 Verlag Helvetica Chimica Acta AG, Zürich</rights><rights>Copyright © 2012 Verlag Helvetica Chimica Acta AG, Zürich.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3822-654ccc4290e2cf9ee61a732e4ecc2647fd1c757d93ab4e23e865aa3a19e6e77e3</citedby><cites>FETCH-LOGICAL-c3822-654ccc4290e2cf9ee61a732e4ecc2647fd1c757d93ab4e23e865aa3a19e6e77e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcbdv.201100122$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcbdv.201100122$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45555,45556</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22422532$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chang, Jiun-Yang</creatorcontrib><creatorcontrib>Fazary, Ahmed Eid</creatorcontrib><creatorcontrib>Lin, Yu-Chi</creatorcontrib><creatorcontrib>Hwang, Tsong-Long</creatorcontrib><creatorcontrib>Shen, Ya-Ching</creatorcontrib><title>New Verticillane Diterpenoids from Cespitularia taeniata</title><title>Chemistry & biodiversity</title><addtitle>Chemistry & Biodiversity</addtitle><description>Chemical investigation of Cespitularia taeniata has led to the isolation of three new verticillanes, cespitulins E–G (1–3, resp.). The structures of these compounds were elucidated by spectroscopic analysis, especially HR‐MS and 2D‐NMR techniques. Compound 1 possesses a rare norverticillane skeleton with two adjacent OH groups at C(5) and C(6), while the seco‐compound 2 with an aldehyde group at C(9) results from an unusual bond cleavage between C(9) and C(10). Pharmacological studies revealed that compound 3 exhibited significant activities on superoxide‐anion generation and elastase release by human neutrophils in response to FMLP/CB. A plausible biogenetic pathway for compound 2 is also discussed.</description><subject>Animals</subject><subject>Anthozoa - chemistry</subject><subject>Anti-inflammatory activity</subject><subject>Cespitularia taeniata</subject><subject>Cespitulins E - G</subject><subject>Diterpenes - chemistry</subject><subject>Diterpenes - isolation & purification</subject><subject>Diterpenes - pharmacology</subject><subject>Diterpenoids</subject><subject>Humans</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>Molecular Conformation</subject><subject>Neutrophils - drug effects</subject><subject>Neutrophils - metabolism</subject><subject>Pancreatic Elastase - metabolism</subject><subject>Soft corals</subject><subject>Superoxides - metabolism</subject><subject>Verticillane diterpenoids</subject><issn>1612-1872</issn><issn>1612-1880</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkMFPwjAUhxujEUSvHs1unobr69Z2RwUFE4aJUTg2pXtLqoNhO0T-e4cg8ebp9TXf78vLj5BLGnVpFMGNmeWfXYhos1CAI9KmnEJIpYyOD28BLXLm_VvDN__ylLQAYoCEQZvIMa6DCbraGluWeoFB39bolriobO6DwlXzoId-aetVqZ3VQa1xYXWtz8lJoUuPF_vZIa8P9y-9YTh6Gjz2bkehYRIg5ElsjIkhjRBMkSJyqgUDjNEY4LEocmpEIvKU6VmMwFDyRGumaYochUDWIdc779JVHyv0tZpbb_Dn1mrlVQoyjTiXsiG7O9K4ynuHhVo6O9duo2iktmWpbVnqUFYTuNqrV7M55gf8t50GSHfA2pa4-Uenenf9yV95uMtaX-PXIavdu-KCiURNxwNFn7OsP80yNWTfodGFKQ</recordid><startdate>201203</startdate><enddate>201203</enddate><creator>Chang, Jiun-Yang</creator><creator>Fazary, Ahmed Eid</creator><creator>Lin, Yu-Chi</creator><creator>Hwang, Tsong-Long</creator><creator>Shen, Ya-Ching</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</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>201203</creationdate><title>New Verticillane Diterpenoids from Cespitularia taeniata</title><author>Chang, Jiun-Yang ; Fazary, Ahmed Eid ; Lin, Yu-Chi ; Hwang, Tsong-Long ; Shen, Ya-Ching</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3822-654ccc4290e2cf9ee61a732e4ecc2647fd1c757d93ab4e23e865aa3a19e6e77e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Animals</topic><topic>Anthozoa - chemistry</topic><topic>Anti-inflammatory activity</topic><topic>Cespitularia taeniata</topic><topic>Cespitulins E - G</topic><topic>Diterpenes - chemistry</topic><topic>Diterpenes - isolation & purification</topic><topic>Diterpenes - pharmacology</topic><topic>Diterpenoids</topic><topic>Humans</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>Molecular Conformation</topic><topic>Neutrophils - drug effects</topic><topic>Neutrophils - metabolism</topic><topic>Pancreatic Elastase - metabolism</topic><topic>Soft corals</topic><topic>Superoxides - metabolism</topic><topic>Verticillane diterpenoids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chang, Jiun-Yang</creatorcontrib><creatorcontrib>Fazary, Ahmed Eid</creatorcontrib><creatorcontrib>Lin, Yu-Chi</creatorcontrib><creatorcontrib>Hwang, Tsong-Long</creatorcontrib><creatorcontrib>Shen, Ya-Ching</creatorcontrib><collection>Istex</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>Chemistry & biodiversity</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chang, Jiun-Yang</au><au>Fazary, Ahmed Eid</au><au>Lin, Yu-Chi</au><au>Hwang, Tsong-Long</au><au>Shen, Ya-Ching</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New Verticillane Diterpenoids from Cespitularia taeniata</atitle><jtitle>Chemistry & biodiversity</jtitle><addtitle>Chemistry & Biodiversity</addtitle><date>2012-03</date><risdate>2012</risdate><volume>9</volume><issue>3</issue><spage>654</spage><epage>661</epage><pages>654-661</pages><issn>1612-1872</issn><eissn>1612-1880</eissn><abstract>Chemical investigation of Cespitularia taeniata has led to the isolation of three new verticillanes, cespitulins E–G (1–3, resp.). The structures of these compounds were elucidated by spectroscopic analysis, especially HR‐MS and 2D‐NMR techniques. Compound 1 possesses a rare norverticillane skeleton with two adjacent OH groups at C(5) and C(6), while the seco‐compound 2 with an aldehyde group at C(9) results from an unusual bond cleavage between C(9) and C(10). Pharmacological studies revealed that compound 3 exhibited significant activities on superoxide‐anion generation and elastase release by human neutrophils in response to FMLP/CB. A plausible biogenetic pathway for compound 2 is also discussed.</abstract><cop>Zürich</cop><pub>WILEY-VCH Verlag</pub><pmid>22422532</pmid><doi>10.1002/cbdv.201100122</doi><tpages>8</tpages></addata></record> |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Animals Anthozoa - chemistry Anti-inflammatory activity Cespitularia taeniata Cespitulins E - G Diterpenes - chemistry Diterpenes - isolation & purification Diterpenes - pharmacology Diterpenoids Humans Magnetic Resonance Spectroscopy Mass Spectrometry Molecular Conformation Neutrophils - drug effects Neutrophils - metabolism Pancreatic Elastase - metabolism Soft corals Superoxides - metabolism Verticillane diterpenoids |
| title | New Verticillane Diterpenoids from Cespitularia taeniata |
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