A New Cacospongionolide Inhibitor of Human Secretory Phospholipase A2 from the Tyrrhenian Sponge Fasciospongia cavernosa and Absolute Configuration of Cacospongionolides
A new inhibitor of human secretory phospholipase A2 (PLA2), cacospongionolide E (4a), has been isolated from the Tyrrhenian sponge Fasciospongia cavernosa. The structure was proposed on the basis of spectroscopic data and by chemical transformations. The absolute configuration of cacospongionolides...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 1998-07, Vol.61 (7), p.931-935 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | De Rosa, Salvatore Crispino, Antonio De Giulio, Alfonso Iodice, Carmine Benrezzouk, Rachid Terencio, M. Carmen Ferrándiz, M. Luisa Alcaraz, M. José Payá, Miguel |
| description | A new inhibitor of human secretory phospholipase A2 (PLA2), cacospongionolide E (4a), has been isolated from the Tyrrhenian sponge Fasciospongia cavernosa. The structure was proposed on the basis of spectroscopic data and by chemical transformations. The absolute configuration of cacospongionolides 2a − 4a was established using the modified Mosher's method. Cacospongionolide E was the most potent inhibitor toward human synovial PLA2, showing higher potency than the reference compound manoalide and exerting no signs of toxicity on human neutrophils. It showed high activity in the Artemia salina bioassay and moderate toxicity in the fish (Gambusia affinis) lethality assay. |
| doi_str_mv | 10.1021/np980122t |
| format | Article |
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It showed high activity in the Artemia salina bioassay and moderate toxicity in the fish (Gambusia affinis) lethality assay.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np980122t</identifier><identifier>PMID: 9677277</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Biological and medical sciences ; Cyprinodontiformes ; Drug Screening Assays, Antitumor ; Enzyme Inhibitors - isolation & purification ; Enzyme Inhibitors - pharmacology ; Enzyme Inhibitors - toxicity ; Furans - isolation & purification ; Furans - pharmacology ; Furans - toxicity ; General pharmacology ; Humans ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Medical sciences ; Molecular Conformation ; Pancreas - enzymology ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Phospholipases A - antagonists & inhibitors ; Phospholipases A2 ; Porifera - chemistry ; Pyrans - isolation & purification ; Pyrans - pharmacology ; Pyrans - toxicity ; Spectrophotometry, Infrared ; Spectrophotometry, Ultraviolet ; Synovial Fluid - enzymology ; Venoms - enzymology</subject><ispartof>Journal of natural products (Washington, D.C.), 1998-07, Vol.61 (7), p.931-935</ispartof><rights>Copyright © 1998 American Chemical Society and American Society of Pharmacognosy</rights><rights>1998 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np980122t$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np980122t$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=2360620$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9677277$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>De Rosa, Salvatore</creatorcontrib><creatorcontrib>Crispino, Antonio</creatorcontrib><creatorcontrib>De Giulio, Alfonso</creatorcontrib><creatorcontrib>Iodice, Carmine</creatorcontrib><creatorcontrib>Benrezzouk, Rachid</creatorcontrib><creatorcontrib>Terencio, M. Carmen</creatorcontrib><creatorcontrib>Ferrándiz, M. Luisa</creatorcontrib><creatorcontrib>Alcaraz, M. José</creatorcontrib><creatorcontrib>Payá, Miguel</creatorcontrib><title>A New Cacospongionolide Inhibitor of Human Secretory Phospholipase A2 from the Tyrrhenian Sponge Fasciospongia cavernosa and Absolute Configuration of Cacospongionolides</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>A new inhibitor of human secretory phospholipase A2 (PLA2), cacospongionolide E (4a), has been isolated from the Tyrrhenian sponge Fasciospongia cavernosa. The structure was proposed on the basis of spectroscopic data and by chemical transformations. The absolute configuration of cacospongionolides 2a − 4a was established using the modified Mosher's method. Cacospongionolide E was the most potent inhibitor toward human synovial PLA2, showing higher potency than the reference compound manoalide and exerting no signs of toxicity on human neutrophils. It showed high activity in the Artemia salina bioassay and moderate toxicity in the fish (Gambusia affinis) lethality assay.</description><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Cyprinodontiformes</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Enzyme Inhibitors - isolation & purification</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Enzyme Inhibitors - toxicity</subject><subject>Furans - isolation & purification</subject><subject>Furans - pharmacology</subject><subject>Furans - toxicity</subject><subject>General pharmacology</subject><subject>Humans</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>Medical sciences</subject><subject>Molecular Conformation</subject><subject>Pancreas - enzymology</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Phospholipases A - antagonists & inhibitors</subject><subject>Phospholipases A2</subject><subject>Porifera - chemistry</subject><subject>Pyrans - isolation & purification</subject><subject>Pyrans - pharmacology</subject><subject>Pyrans - toxicity</subject><subject>Spectrophotometry, Infrared</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Synovial Fluid - enzymology</subject><subject>Venoms - enzymology</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1998</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNplkU1vEzEQhq0KVELbAz8AyQc4LvgjXu8eo6gllapSKaFXa3Z33HVJ7JW9C-Qn8S9xlCgXTqOZ99E7X4R84OwLZ4J_9UNdMS7EeEFmXAlWlEyoN2TGeCkLWZXzd-R9Sq-MMclqdUku61JrofWM_F3QR_xNl9CGNAT_4oIPW9chvfe9a9wYIg2WrqYdeLrGNmKu7OlTn-k-gwMkpAtBbQw7OvZIN_sYe_TugB_8kN5Bat3JHGgLvzD6kICC7-iiSWE7jUiXwVv3MkUY8wCHjv8NlK7JWwvbhDeneEV-3N1ulqvi4fu3--XioQDBq7FoqkpYaKARObd8DnYOula86hrEWjIQc4GWIXJrFRe8zJBUtcQabAudllfk49F3mJoddmaIbgdxb04ny_qnk54Xg62N4FuXzpiQJSsFy1hxxFwa8c9ZhvjTlFpqZTZPa6M2j1qt1s-GZ_7zkYc2mdcwRZ-XNJyZw4PN-cHyH98umZ4</recordid><startdate>199807</startdate><enddate>199807</enddate><creator>De Rosa, Salvatore</creator><creator>Crispino, Antonio</creator><creator>De Giulio, Alfonso</creator><creator>Iodice, Carmine</creator><creator>Benrezzouk, Rachid</creator><creator>Terencio, M. Carmen</creator><creator>Ferrándiz, M. Luisa</creator><creator>Alcaraz, M. José</creator><creator>Payá, Miguel</creator><general>American Chemical Society</general><general>American ChemicalSociety</general><general>American Society of Pharmacognosy</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope></search><sort><creationdate>199807</creationdate><title>A New Cacospongionolide Inhibitor of Human Secretory Phospholipase A2 from the Tyrrhenian Sponge Fasciospongia cavernosa and Absolute Configuration of Cacospongionolides</title><author>De Rosa, Salvatore ; Crispino, Antonio ; De Giulio, Alfonso ; Iodice, Carmine ; Benrezzouk, Rachid ; Terencio, M. Carmen ; Ferrándiz, M. Luisa ; Alcaraz, M. José ; Payá, Miguel</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a218t-b882fabab2a21f14af4a79518dbee930a242ef0ee1ff512161f13593e9afcad73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1998</creationdate><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Cyprinodontiformes</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Enzyme Inhibitors - isolation & purification</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Enzyme Inhibitors - toxicity</topic><topic>Furans - isolation & purification</topic><topic>Furans - pharmacology</topic><topic>Furans - toxicity</topic><topic>General pharmacology</topic><topic>Humans</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>Medical sciences</topic><topic>Molecular Conformation</topic><topic>Pancreas - enzymology</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Phospholipases A - antagonists & inhibitors</topic><topic>Phospholipases A2</topic><topic>Porifera - chemistry</topic><topic>Pyrans - isolation & purification</topic><topic>Pyrans - pharmacology</topic><topic>Pyrans - toxicity</topic><topic>Spectrophotometry, Infrared</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>Synovial Fluid - enzymology</topic><topic>Venoms - enzymology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>De Rosa, Salvatore</creatorcontrib><creatorcontrib>Crispino, Antonio</creatorcontrib><creatorcontrib>De Giulio, Alfonso</creatorcontrib><creatorcontrib>Iodice, Carmine</creatorcontrib><creatorcontrib>Benrezzouk, Rachid</creatorcontrib><creatorcontrib>Terencio, M. Carmen</creatorcontrib><creatorcontrib>Ferrándiz, M. Luisa</creatorcontrib><creatorcontrib>Alcaraz, M. José</creatorcontrib><creatorcontrib>Payá, Miguel</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>De Rosa, Salvatore</au><au>Crispino, Antonio</au><au>De Giulio, Alfonso</au><au>Iodice, Carmine</au><au>Benrezzouk, Rachid</au><au>Terencio, M. Carmen</au><au>Ferrándiz, M. Luisa</au><au>Alcaraz, M. José</au><au>Payá, Miguel</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A New Cacospongionolide Inhibitor of Human Secretory Phospholipase A2 from the Tyrrhenian Sponge Fasciospongia cavernosa and Absolute Configuration of Cacospongionolides</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>1998-07</date><risdate>1998</risdate><volume>61</volume><issue>7</issue><spage>931</spage><epage>935</epage><pages>931-935</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>A new inhibitor of human secretory phospholipase A2 (PLA2), cacospongionolide E (4a), has been isolated from the Tyrrhenian sponge Fasciospongia cavernosa. The structure was proposed on the basis of spectroscopic data and by chemical transformations. The absolute configuration of cacospongionolides 2a − 4a was established using the modified Mosher's method. Cacospongionolide E was the most potent inhibitor toward human synovial PLA2, showing higher potency than the reference compound manoalide and exerting no signs of toxicity on human neutrophils. It showed high activity in the Artemia salina bioassay and moderate toxicity in the fish (Gambusia affinis) lethality assay.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>9677277</pmid><doi>10.1021/np980122t</doi><tpages>5</tpages></addata></record> |
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| ispartof | Journal of natural products (Washington, D.C.), 1998-07, Vol.61 (7), p.931-935 |
| issn | 0163-3864 1520-6025 |
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| recordid | cdi_pubmed_primary_9677277 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Animals Biological and medical sciences Cyprinodontiformes Drug Screening Assays, Antitumor Enzyme Inhibitors - isolation & purification Enzyme Inhibitors - pharmacology Enzyme Inhibitors - toxicity Furans - isolation & purification Furans - pharmacology Furans - toxicity General pharmacology Humans Magnetic Resonance Spectroscopy Mass Spectrometry Medical sciences Molecular Conformation Pancreas - enzymology Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Phospholipases A - antagonists & inhibitors Phospholipases A2 Porifera - chemistry Pyrans - isolation & purification Pyrans - pharmacology Pyrans - toxicity Spectrophotometry, Infrared Spectrophotometry, Ultraviolet Synovial Fluid - enzymology Venoms - enzymology |
| title | A New Cacospongionolide Inhibitor of Human Secretory Phospholipase A2 from the Tyrrhenian Sponge Fasciospongia cavernosa and Absolute Configuration of Cacospongionolides |
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