Chemical characterisation of three haemolytic compounds from the microalgal species Fibrocapsa japonica (Raphidophyceae)
The molecular structures of the three main haemolytic compounds (Fj1, Fj2 and Fj3) isolated from the ichthyotoxic microalgal species Fibrocapsa japonica have been investigated by NMR, LC–ESI–MS, ESI–MS–MS, IR, GC–MS and GC–HRMS methods. They are polyunsaturated fatty acids which we identified as: 6,...
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| Veröffentlicht in: | Toxicon (Oxford) 2004-03, Vol.43 (4), p.355-363 |
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| creator | Fu, Meng Koulman, Albert van Rijssel, Marion Lützen, Arne de Boer, M.Karin Tyl, Monika R. Liebezeit, Gerd |
| description | The molecular structures of the three main haemolytic compounds (Fj1, Fj2 and Fj3) isolated from the ichthyotoxic microalgal species
Fibrocapsa japonica have been investigated by NMR, LC–ESI–MS, ESI–MS–MS, IR, GC–MS and GC–HRMS methods. They are polyunsaturated fatty acids which we identified as: 6,9,12,15-octadecatetraenoic acid (OTA, C18:4ω3), 5,8,11,14,17-eicosapentaenoic acid (EPA, C20:5ω3) and 5,8,11,14-eicosatetraenoic acid (arachidonic acid AA, C20:4ω6). The identity of the latter two was confirmed on the basis of commercial standards (C20:5ω3 and C20:4ω6). Both displayed the same spectroscopic and chromatographic characteristics as Fj2 and Fj3 and had a similar strong haemolytic effect. We propose that when
F. japonica cells accumulate in fish gills during blooms these compounds could be the cause of icthyotoxicity. |
| doi_str_mv | 10.1016/j.toxicon.2003.09.012 |
| format | Article |
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Fibrocapsa japonica have been investigated by NMR, LC–ESI–MS, ESI–MS–MS, IR, GC–MS and GC–HRMS methods. They are polyunsaturated fatty acids which we identified as: 6,9,12,15-octadecatetraenoic acid (OTA, C18:4ω3), 5,8,11,14,17-eicosapentaenoic acid (EPA, C20:5ω3) and 5,8,11,14-eicosatetraenoic acid (arachidonic acid AA, C20:4ω6). The identity of the latter two was confirmed on the basis of commercial standards (C20:5ω3 and C20:4ω6). Both displayed the same spectroscopic and chromatographic characteristics as Fj2 and Fj3 and had a similar strong haemolytic effect. We propose that when
F. japonica cells accumulate in fish gills during blooms these compounds could be the cause of icthyotoxicity.</description><identifier>ISSN: 0041-0101</identifier><identifier>EISSN: 1879-3150</identifier><identifier>DOI: 10.1016/j.toxicon.2003.09.012</identifier><identifier>PMID: 15051398</identifier><identifier>CODEN: TOXIA6</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>5,8,11,14,17-Eicosapentaenoic acid (EPA, C20:5ω3) ; 5,8,11,14-Eicosatetraenoic acid (arachidonic acid AA, C20:4ω6) ; 6,9,12,15-Octadecatetraenoic acid (OTA, C18:4ω3) ; Animal poisons toxicology. Antivenoms ; Biological and medical sciences ; Chromatography, High Pressure Liquid ; Erythrocyte lysis assay ; Eukaryota - chemistry ; Fatty Acids, Unsaturated - chemistry ; Fibrocapsa japonica ; Gas Chromatography-Mass Spectrometry ; Gas chromatography–high resolution mass spectrometry ; Haemolytic compounds ; Hemolysis ; High performance liquid chromatography ; Infrared spectroscopy ; Liquid chromatography–electrospray ionisation–mass spectrometry ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Medical sciences ; Nuclear magnetic resonance ; Raphidophyceae ; Spectroscopy, Near-Infrared ; Toxicology</subject><ispartof>Toxicon (Oxford), 2004-03, Vol.43 (4), p.355-363</ispartof><rights>2003</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c517t-50f5c9d72623f82d99d13f05a562e54ada49956fd8685031d06b29fe2efd684b3</citedby><cites>FETCH-LOGICAL-c517t-50f5c9d72623f82d99d13f05a562e54ada49956fd8685031d06b29fe2efd684b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0041010103002824$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15668105$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15051398$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Fu, Meng</creatorcontrib><creatorcontrib>Koulman, Albert</creatorcontrib><creatorcontrib>van Rijssel, Marion</creatorcontrib><creatorcontrib>Lützen, Arne</creatorcontrib><creatorcontrib>de Boer, M.Karin</creatorcontrib><creatorcontrib>Tyl, Monika R.</creatorcontrib><creatorcontrib>Liebezeit, Gerd</creatorcontrib><title>Chemical characterisation of three haemolytic compounds from the microalgal species Fibrocapsa japonica (Raphidophyceae)</title><title>Toxicon (Oxford)</title><addtitle>Toxicon</addtitle><description>The molecular structures of the three main haemolytic compounds (Fj1, Fj2 and Fj3) isolated from the ichthyotoxic microalgal species
Fibrocapsa japonica have been investigated by NMR, LC–ESI–MS, ESI–MS–MS, IR, GC–MS and GC–HRMS methods. They are polyunsaturated fatty acids which we identified as: 6,9,12,15-octadecatetraenoic acid (OTA, C18:4ω3), 5,8,11,14,17-eicosapentaenoic acid (EPA, C20:5ω3) and 5,8,11,14-eicosatetraenoic acid (arachidonic acid AA, C20:4ω6). The identity of the latter two was confirmed on the basis of commercial standards (C20:5ω3 and C20:4ω6). Both displayed the same spectroscopic and chromatographic characteristics as Fj2 and Fj3 and had a similar strong haemolytic effect. We propose that when
F. japonica cells accumulate in fish gills during blooms these compounds could be the cause of icthyotoxicity.</description><subject>5,8,11,14,17-Eicosapentaenoic acid (EPA, C20:5ω3)</subject><subject>5,8,11,14-Eicosatetraenoic acid (arachidonic acid AA, C20:4ω6)</subject><subject>6,9,12,15-Octadecatetraenoic acid (OTA, C18:4ω3)</subject><subject>Animal poisons toxicology. Antivenoms</subject><subject>Biological and medical sciences</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Erythrocyte lysis assay</subject><subject>Eukaryota - chemistry</subject><subject>Fatty Acids, Unsaturated - chemistry</subject><subject>Fibrocapsa japonica</subject><subject>Gas Chromatography-Mass Spectrometry</subject><subject>Gas chromatography–high resolution mass spectrometry</subject><subject>Haemolytic compounds</subject><subject>Hemolysis</subject><subject>High performance liquid chromatography</subject><subject>Infrared spectroscopy</subject><subject>Liquid chromatography–electrospray ionisation–mass spectrometry</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>Medical sciences</subject><subject>Nuclear magnetic resonance</subject><subject>Raphidophyceae</subject><subject>Spectroscopy, Near-Infrared</subject><subject>Toxicology</subject><issn>0041-0101</issn><issn>1879-3150</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkcFu1DAURS1ERYfCJ4C8AcEiwXbGTrxCaEQBqVKlqqytN_Yz8SiJg51Bnb_H1USCXVdevHOv7XcIecNZzRlXnw71Eh-CjVMtGGtqpmvGxTOy4V2rq4ZL9pxsGNvyihX8krzM-cAK2Gn1glyWseSN7jbkYdfjGCwM1PaQwC6YQoYlxIlGT5c-IdIecIzDaQmW2jjO8Ti5TH2KY5kjLekUYfhVKvKMNmCm12GfooU5Az3AHKfSTz_cwdwHF-f-ZBHw4yty4WHI-Ho9r8jP66_3u-_Vze23H7svN5WVvF0qyby02rVCicZ3wmnteOOZBKkEyi042GotlXed6iRruGNqL7RHgd6pbrtvrsj7c--c4u8j5sWMIVscBpgwHrNpedsp0bInQd5qrgVvCyjPYPl3zgm9mVMYIZ0MZ-bRjTmY1Y15dGOYNsVNyb1dLzjuR3T_UquMArxbAcjFiE8w2ZD_45TqOJOF-3zmsOztT8Bkcln7ZNGFhHYxLoYnnvIXETqxmQ</recordid><startdate>20040315</startdate><enddate>20040315</enddate><creator>Fu, Meng</creator><creator>Koulman, Albert</creator><creator>van Rijssel, Marion</creator><creator>Lützen, Arne</creator><creator>de Boer, M.Karin</creator><creator>Tyl, Monika R.</creator><creator>Liebezeit, Gerd</creator><general>Elsevier Ltd</general><general>Elsevier Science</general><scope>IQODW</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>7U7</scope><scope>C1K</scope><scope>F1W</scope><scope>H95</scope><scope>L.G</scope><scope>M7N</scope><scope>7X8</scope></search><sort><creationdate>20040315</creationdate><title>Chemical characterisation of three haemolytic compounds from the microalgal species Fibrocapsa japonica (Raphidophyceae)</title><author>Fu, Meng ; Koulman, Albert ; van Rijssel, Marion ; Lützen, Arne ; de Boer, M.Karin ; Tyl, Monika R. ; Liebezeit, Gerd</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c517t-50f5c9d72623f82d99d13f05a562e54ada49956fd8685031d06b29fe2efd684b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>5,8,11,14,17-Eicosapentaenoic acid (EPA, C20:5ω3)</topic><topic>5,8,11,14-Eicosatetraenoic acid (arachidonic acid AA, C20:4ω6)</topic><topic>6,9,12,15-Octadecatetraenoic acid (OTA, C18:4ω3)</topic><topic>Animal poisons toxicology. Antivenoms</topic><topic>Biological and medical sciences</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Erythrocyte lysis assay</topic><topic>Eukaryota - chemistry</topic><topic>Fatty Acids, Unsaturated - chemistry</topic><topic>Fibrocapsa japonica</topic><topic>Gas Chromatography-Mass Spectrometry</topic><topic>Gas chromatography–high resolution mass spectrometry</topic><topic>Haemolytic compounds</topic><topic>Hemolysis</topic><topic>High performance liquid chromatography</topic><topic>Infrared spectroscopy</topic><topic>Liquid chromatography–electrospray ionisation–mass spectrometry</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>Medical sciences</topic><topic>Nuclear magnetic resonance</topic><topic>Raphidophyceae</topic><topic>Spectroscopy, Near-Infrared</topic><topic>Toxicology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fu, Meng</creatorcontrib><creatorcontrib>Koulman, Albert</creatorcontrib><creatorcontrib>van Rijssel, Marion</creatorcontrib><creatorcontrib>Lützen, Arne</creatorcontrib><creatorcontrib>de Boer, M.Karin</creatorcontrib><creatorcontrib>Tyl, Monika R.</creatorcontrib><creatorcontrib>Liebezeit, Gerd</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Toxicology Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 1: Biological Sciences & Living Resources</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>MEDLINE - Academic</collection><jtitle>Toxicon (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fu, Meng</au><au>Koulman, Albert</au><au>van Rijssel, Marion</au><au>Lützen, Arne</au><au>de Boer, M.Karin</au><au>Tyl, Monika R.</au><au>Liebezeit, Gerd</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemical characterisation of three haemolytic compounds from the microalgal species Fibrocapsa japonica (Raphidophyceae)</atitle><jtitle>Toxicon (Oxford)</jtitle><addtitle>Toxicon</addtitle><date>2004-03-15</date><risdate>2004</risdate><volume>43</volume><issue>4</issue><spage>355</spage><epage>363</epage><pages>355-363</pages><issn>0041-0101</issn><eissn>1879-3150</eissn><coden>TOXIA6</coden><abstract>The molecular structures of the three main haemolytic compounds (Fj1, Fj2 and Fj3) isolated from the ichthyotoxic microalgal species
Fibrocapsa japonica have been investigated by NMR, LC–ESI–MS, ESI–MS–MS, IR, GC–MS and GC–HRMS methods. They are polyunsaturated fatty acids which we identified as: 6,9,12,15-octadecatetraenoic acid (OTA, C18:4ω3), 5,8,11,14,17-eicosapentaenoic acid (EPA, C20:5ω3) and 5,8,11,14-eicosatetraenoic acid (arachidonic acid AA, C20:4ω6). The identity of the latter two was confirmed on the basis of commercial standards (C20:5ω3 and C20:4ω6). Both displayed the same spectroscopic and chromatographic characteristics as Fj2 and Fj3 and had a similar strong haemolytic effect. We propose that when
F. japonica cells accumulate in fish gills during blooms these compounds could be the cause of icthyotoxicity.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>15051398</pmid><doi>10.1016/j.toxicon.2003.09.012</doi><tpages>9</tpages></addata></record> |
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| subjects | 5,8,11,14,17-Eicosapentaenoic acid (EPA, C20:5ω3) 5,8,11,14-Eicosatetraenoic acid (arachidonic acid AA, C20:4ω6) 6,9,12,15-Octadecatetraenoic acid (OTA, C18:4ω3) Animal poisons toxicology. Antivenoms Biological and medical sciences Chromatography, High Pressure Liquid Erythrocyte lysis assay Eukaryota - chemistry Fatty Acids, Unsaturated - chemistry Fibrocapsa japonica Gas Chromatography-Mass Spectrometry Gas chromatography–high resolution mass spectrometry Haemolytic compounds Hemolysis High performance liquid chromatography Infrared spectroscopy Liquid chromatography–electrospray ionisation–mass spectrometry Magnetic Resonance Spectroscopy Mass Spectrometry Medical sciences Nuclear magnetic resonance Raphidophyceae Spectroscopy, Near-Infrared Toxicology |
| title | Chemical characterisation of three haemolytic compounds from the microalgal species Fibrocapsa japonica (Raphidophyceae) |
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