Identification and Egg Hatching Activity of Monohydroxy Fatty Acid Eicosanoids in the Barnacle Balanus balanoides
Monohydroxy fatty acids (MHFAs) were isolated from homogenates of the barnacle Balanus balanoides and identified by gas chromatography—mass spectrometry (gc- ms) as 14- and 17-hydroxy docosahexaenoic acids, 8-, 11-, 12-, 15- and 18-hydroxy eicosapentaenoic acids, 13- and 16-hydroxyoctadecatrienoic a...
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| Veröffentlicht in: | Proceedings of the Royal Society. B, Biological sciences Biological sciences, 1992-01, Vol.247 (1318), p.41-46 |
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| creator | Hill, E. M. Holland, D. L. |
| description | Monohydroxy fatty acids (MHFAs) were isolated from homogenates of the barnacle Balanus balanoides and identified by gas chromatography—mass spectrometry (gc- ms) as 14- and 17-hydroxy docosahexaenoic acids, 8-, 11-, 12-, 15- and 18-hydroxy eicosapentaenoic acids, 13- and 16-hydroxyoctadecatrienoic acids and 9-, 13- and 15-hydroxyoctadecadienoic acids. Each monohydroxy fatty acid was tested for egg hatching activity in a bioassay using Elminius modestus egg masses, but 8-hydroxy-5, 9, 11, 14, 17- eicosapentaenoic acid (8-HEPE) was the only M H FA with barnacle egg hatching activity. Studies on the egg hatching activity of MHFAs prepared from the oxidation of polyunsaturated fatty acids showed that activity was confined to the 8-hydroxy isomer of eicosapentaenoic acid and arachidonic acid, and that unsaturation at C5 and C14, but not C17, was essential for activity. In addition, the 8 conformation is necessary for activity, as 8(R)-HEPE caused egg hatching at 10-7 m whereas the enantiomer 8(S')-HEPE was inactive. |
| doi_str_mv | 10.1098/rspb.1992.0007 |
| format | Article |
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M. ; Holland, D. L.</creator><creatorcontrib>Hill, E. M. ; Holland, D. L.</creatorcontrib><description>Monohydroxy fatty acids (MHFAs) were isolated from homogenates of the barnacle Balanus balanoides and identified by gas chromatography—mass spectrometry (gc- ms) as 14- and 17-hydroxy docosahexaenoic acids, 8-, 11-, 12-, 15- and 18-hydroxy eicosapentaenoic acids, 13- and 16-hydroxyoctadecatrienoic acids and 9-, 13- and 15-hydroxyoctadecadienoic acids. Each monohydroxy fatty acid was tested for egg hatching activity in a bioassay using Elminius modestus egg masses, but 8-hydroxy-5, 9, 11, 14, 17- eicosapentaenoic acid (8-HEPE) was the only M H FA with barnacle egg hatching activity. Studies on the egg hatching activity of MHFAs prepared from the oxidation of polyunsaturated fatty acids showed that activity was confined to the 8-hydroxy isomer of eicosapentaenoic acid and arachidonic acid, and that unsaturation at C5 and C14, but not C17, was essential for activity. In addition, the 8 conformation is necessary for activity, as 8(R)-HEPE caused egg hatching at 10-7 m whereas the enantiomer 8(S')-HEPE was inactive.</description><identifier>ISSN: 0962-8452</identifier><identifier>EISSN: 1471-2954</identifier><identifier>DOI: 10.1098/rspb.1992.0007</identifier><identifier>PMID: 1348120</identifier><language>eng</language><publisher>London: The Royal Society</publisher><subject>Animals ; Bioassay ; Biological Assay ; Carboxyl compounds ; Chromatography, High Pressure Liquid ; Egg masses ; Eggs ; Eicosanoids ; Eicosanoids - isolation & purification ; Eicosanoids - pharmacology ; Embryo, Nonmammalian - drug effects ; Embryo, Nonmammalian - physiology ; Esters ; Fatty acids ; Gas Chromatography-Mass Spectrometry ; Hatching ; Hydroxy Acids - isolation & purification ; Hydroxy Acids - pharmacology ; Isomerism ; Oxidation ; Structure-Activity Relationship ; Thoracica - physiology ; Unsaturated fatty acids</subject><ispartof>Proceedings of the Royal Society. 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M.</creatorcontrib><creatorcontrib>Holland, D. L.</creatorcontrib><title>Identification and Egg Hatching Activity of Monohydroxy Fatty Acid Eicosanoids in the Barnacle Balanus balanoides</title><title>Proceedings of the Royal Society. B, Biological sciences</title><addtitle>Proc. R. Soc. Lond. B</addtitle><addtitle>Proc. R. Soc. Lond. B</addtitle><description>Monohydroxy fatty acids (MHFAs) were isolated from homogenates of the barnacle Balanus balanoides and identified by gas chromatography—mass spectrometry (gc- ms) as 14- and 17-hydroxy docosahexaenoic acids, 8-, 11-, 12-, 15- and 18-hydroxy eicosapentaenoic acids, 13- and 16-hydroxyoctadecatrienoic acids and 9-, 13- and 15-hydroxyoctadecadienoic acids. Each monohydroxy fatty acid was tested for egg hatching activity in a bioassay using Elminius modestus egg masses, but 8-hydroxy-5, 9, 11, 14, 17- eicosapentaenoic acid (8-HEPE) was the only M H FA with barnacle egg hatching activity. Studies on the egg hatching activity of MHFAs prepared from the oxidation of polyunsaturated fatty acids showed that activity was confined to the 8-hydroxy isomer of eicosapentaenoic acid and arachidonic acid, and that unsaturation at C5 and C14, but not C17, was essential for activity. In addition, the 8 conformation is necessary for activity, as 8(R)-HEPE caused egg hatching at 10-7 m whereas the enantiomer 8(S')-HEPE was inactive.</description><subject>Animals</subject><subject>Bioassay</subject><subject>Biological Assay</subject><subject>Carboxyl compounds</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Egg masses</subject><subject>Eggs</subject><subject>Eicosanoids</subject><subject>Eicosanoids - isolation & purification</subject><subject>Eicosanoids - pharmacology</subject><subject>Embryo, Nonmammalian - drug effects</subject><subject>Embryo, Nonmammalian - physiology</subject><subject>Esters</subject><subject>Fatty acids</subject><subject>Gas Chromatography-Mass Spectrometry</subject><subject>Hatching</subject><subject>Hydroxy Acids - isolation & purification</subject><subject>Hydroxy Acids - pharmacology</subject><subject>Isomerism</subject><subject>Oxidation</subject><subject>Structure-Activity Relationship</subject><subject>Thoracica - physiology</subject><subject>Unsaturated fatty acids</subject><issn>0962-8452</issn><issn>1471-2954</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1992</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9ks1v0zAYxiMEGmVw5YCE5NNu6fyV2LkgddNGJ60D8XW1HMdpXdI4s52x8NfPaabBhNjJfv383q9HTpK3CM4RLPix8105R0WB5xBC9iyZIcpQiouMPk9msMhxymmGXyavvN9Gosh4dpAcIEI5wnCWXF9Uug2mNkoGY1sg2wqcrddgKYPamHYNFiqYGxMGYGuwsq3dDJWztwM4lyE-LpSJvFHWy9aaygPTgrDR4ES6VqpmvDSy7T0oxzMS2r9OXtSy8frN_XmYfD8_-3a6TC8_fbw4XVymKiuykBa0JBqVGsoakZKwqtI5ZzWHNVGYFVihqirrjPMYZUrynJdaUZxLTCGDOSSHydFUt3P2utc-iJ3xSjdxDm17LxjmeU4pi-B8ApWz3jtdi86ZnXSDQFCMHovRYzF6LEaPY8L7-8p9udPVH3wyNepk0p0d4oZWGR0GsbV99KTx_6_qn8r68vXzSYThDabMIIK4gJwgmEFMsfhtun25ERAREMb7Xos99rjNv13fTV23Plj3sAotGENRTCfR-KBvH0TpfoqcEZaJH5wKSJZ0dcVX4irycOI3Zr35ZZwWj3aJQed8uR9wPxodW3x4MmWcVtk2xE_6d56o-6YRXVWTO1_37xs</recordid><startdate>19920122</startdate><enddate>19920122</enddate><creator>Hill, E. M.</creator><creator>Holland, D. L.</creator><general>The Royal Society</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>19920122</creationdate><title>Identification and Egg Hatching Activity of Monohydroxy Fatty Acid Eicosanoids in the Barnacle Balanus balanoides</title><author>Hill, E. M. ; Holland, D. L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c595t-94b3e1be0af13b37dde687f80f3c2792c1ddbf588c275ca868bec426a24070603</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1992</creationdate><topic>Animals</topic><topic>Bioassay</topic><topic>Biological Assay</topic><topic>Carboxyl compounds</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Egg masses</topic><topic>Eggs</topic><topic>Eicosanoids</topic><topic>Eicosanoids - isolation & purification</topic><topic>Eicosanoids - pharmacology</topic><topic>Embryo, Nonmammalian - drug effects</topic><topic>Embryo, Nonmammalian - physiology</topic><topic>Esters</topic><topic>Fatty acids</topic><topic>Gas Chromatography-Mass Spectrometry</topic><topic>Hatching</topic><topic>Hydroxy Acids - isolation & purification</topic><topic>Hydroxy Acids - pharmacology</topic><topic>Isomerism</topic><topic>Oxidation</topic><topic>Structure-Activity Relationship</topic><topic>Thoracica - physiology</topic><topic>Unsaturated fatty acids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hill, E. M.</creatorcontrib><creatorcontrib>Holland, D. L.</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>Proceedings of the Royal Society. B, Biological sciences</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hill, E. M.</au><au>Holland, D. L.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Identification and Egg Hatching Activity of Monohydroxy Fatty Acid Eicosanoids in the Barnacle Balanus balanoides</atitle><jtitle>Proceedings of the Royal Society. B, Biological sciences</jtitle><stitle>Proc. R. Soc. Lond. B</stitle><addtitle>Proc. R. Soc. Lond. B</addtitle><date>1992-01-22</date><risdate>1992</risdate><volume>247</volume><issue>1318</issue><spage>41</spage><epage>46</epage><pages>41-46</pages><issn>0962-8452</issn><eissn>1471-2954</eissn><abstract>Monohydroxy fatty acids (MHFAs) were isolated from homogenates of the barnacle Balanus balanoides and identified by gas chromatography—mass spectrometry (gc- ms) as 14- and 17-hydroxy docosahexaenoic acids, 8-, 11-, 12-, 15- and 18-hydroxy eicosapentaenoic acids, 13- and 16-hydroxyoctadecatrienoic acids and 9-, 13- and 15-hydroxyoctadecadienoic acids. Each monohydroxy fatty acid was tested for egg hatching activity in a bioassay using Elminius modestus egg masses, but 8-hydroxy-5, 9, 11, 14, 17- eicosapentaenoic acid (8-HEPE) was the only M H FA with barnacle egg hatching activity. Studies on the egg hatching activity of MHFAs prepared from the oxidation of polyunsaturated fatty acids showed that activity was confined to the 8-hydroxy isomer of eicosapentaenoic acid and arachidonic acid, and that unsaturation at C5 and C14, but not C17, was essential for activity. In addition, the 8 conformation is necessary for activity, as 8(R)-HEPE caused egg hatching at 10-7 m whereas the enantiomer 8(S')-HEPE was inactive.</abstract><cop>London</cop><pub>The Royal Society</pub><pmid>1348120</pmid><doi>10.1098/rspb.1992.0007</doi><tpages>6</tpages></addata></record> |
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| identifier | ISSN: 0962-8452 |
| ispartof | Proceedings of the Royal Society. B, Biological sciences, 1992-01, Vol.247 (1318), p.41-46 |
| issn | 0962-8452 1471-2954 |
| language | eng |
| recordid | cdi_royalsociety_journals_10_1098_rspb_1992_0007 |
| source | Jstor Complete Legacy; MEDLINE |
| subjects | Animals Bioassay Biological Assay Carboxyl compounds Chromatography, High Pressure Liquid Egg masses Eggs Eicosanoids Eicosanoids - isolation & purification Eicosanoids - pharmacology Embryo, Nonmammalian - drug effects Embryo, Nonmammalian - physiology Esters Fatty acids Gas Chromatography-Mass Spectrometry Hatching Hydroxy Acids - isolation & purification Hydroxy Acids - pharmacology Isomerism Oxidation Structure-Activity Relationship Thoracica - physiology Unsaturated fatty acids |
| title | Identification and Egg Hatching Activity of Monohydroxy Fatty Acid Eicosanoids in the Barnacle Balanus balanoides |
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