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Full characterization of PDX, a neuroprotectin/protectin D1 isomer, which inhibits blood platelet aggregation
Our study aimed to establish the complete structure of the main dihydroxy conjugated triene issued from the lipoxygenation (soybean enzyme) of docosahexaenoic acid, named PDX, an isomer of protectin/neuroprotectin D1 (PD1/NPD1) described by Bazan and Serhan. NMR approaches and other chemical charact...
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| Published in: | FEBS letters 2009-11, Vol.583 (21), p.3478-3484 |
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| Main Authors: | , , , , , , |
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| container_issue | 21 |
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| creator | Chen, P. Fenet, B. Michaud, S. Tomczyk, N. Véricel, E. Lagarde, M. Guichardant, M. |
| description | Our study aimed to establish the complete structure of the main dihydroxy conjugated triene issued from the lipoxygenation (soybean enzyme) of docosahexaenoic acid, named PDX, an isomer of protectin/neuroprotectin D1 (PD1/NPD1) described by Bazan and Serhan. NMR approaches and other chemical characterization (e.g. GC–MS, HPLC and LC–MS/MS) indicated that PDX is 10(S),17(S)-dihydroxy-docosahexa-4
Z,7
Z,11
E,13
Z,15
E,19
Z-enoic acid. The use of
18O
2 and mass spectrometry showed that PDX is a double lipoxygenation product. Its structure differs from PD1, with
E,Z,E geometry (PDX) instead of
E,E,Z (PD1) and S configuration at carbon 10 instead of R. PDX inhibits human blood platelet aggregation at sub-micromolar concentrations. |
| doi_str_mv | 10.1016/j.febslet.2009.10.004 |
| format | article |
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Z,7
Z,11
E,13
Z,15
E,19
Z-enoic acid. The use of
18O
2 and mass spectrometry showed that PDX is a double lipoxygenation product. Its structure differs from PD1, with
E,Z,E geometry (PDX) instead of
E,E,Z (PD1) and S configuration at carbon 10 instead of R. PDX inhibits human blood platelet aggregation at sub-micromolar concentrations.</description><identifier>ISSN: 0014-5793</identifier><identifier>EISSN: 1873-3468</identifier><identifier>DOI: 10.1016/j.febslet.2009.10.004</identifier><identifier>PMID: 19818771</identifier><language>eng</language><publisher>England: Elsevier B.V</publisher><subject>10,17-Dihydroxy-docosahexaenoic acid ; 15-Lipoxygenase ; Arachidonate 15-Lipoxygenase ; Arachidonate 15-Lipoxygenase - metabolism ; BSTFA ; Carbon ; Carbon - chemistry ; DHA ; Docosahexaenoic acid ; Docosahexaenoic Acids ; Docosahexaenoic Acids - chemistry ; Docosahexaenoic Acids - metabolism ; Docosahexaenoic Acids - pharmacology ; Dose-Response Relationship, Drug ; Double lipoxygenation ; Food and Nutrition ; Gas Chromatography-Mass Spectrometry ; Glycine max - enzymology ; heptafluorobutyryl imidazole ; HFBI ; Humans ; Hydroxides ; Hydroxides - chemistry ; Ion mobility separation ; Life Sciences ; Magnetic Resonance Spectroscopy ; N,O-Bis(trimethylsilyl)-trifluroroacetamide ; Platelet Aggregation ; Platelet Aggregation - drug effects ; sLOX ; soybean lipoxygenase ; Soybeans ; Stereoisomerism</subject><ispartof>FEBS letters, 2009-11, Vol.583 (21), p.3478-3484</ispartof><rights>2009 Federation of European Biochemical Societies</rights><rights>FEBS Letters 583 (2009) 1873-3468 © 2015 Federation of European Biochemical Societies</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6101-44f3003c2cca02800707fd3dbb6c7d8fc11a893efbd308fde8c6d140c8090cab3</citedby><cites>FETCH-LOGICAL-c6101-44f3003c2cca02800707fd3dbb6c7d8fc11a893efbd308fde8c6d140c8090cab3</cites><orcidid>0000-0002-8068-1891</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0014579309007741$$EHTML$$P50$$Gelsevier$$Hfree_for_read</linktohtml><link.rule.ids>230,314,780,784,885,3549,27924,27925,45780</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19818771$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://inserm.hal.science/inserm-00429322$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Chen, P.</creatorcontrib><creatorcontrib>Fenet, B.</creatorcontrib><creatorcontrib>Michaud, S.</creatorcontrib><creatorcontrib>Tomczyk, N.</creatorcontrib><creatorcontrib>Véricel, E.</creatorcontrib><creatorcontrib>Lagarde, M.</creatorcontrib><creatorcontrib>Guichardant, M.</creatorcontrib><title>Full characterization of PDX, a neuroprotectin/protectin D1 isomer, which inhibits blood platelet aggregation</title><title>FEBS letters</title><addtitle>FEBS Lett</addtitle><description>Our study aimed to establish the complete structure of the main dihydroxy conjugated triene issued from the lipoxygenation (soybean enzyme) of docosahexaenoic acid, named PDX, an isomer of protectin/neuroprotectin D1 (PD1/NPD1) described by Bazan and Serhan. NMR approaches and other chemical characterization (e.g. GC–MS, HPLC and LC–MS/MS) indicated that PDX is 10(S),17(S)-dihydroxy-docosahexa-4
Z,7
Z,11
E,13
Z,15
E,19
Z-enoic acid. The use of
18O
2 and mass spectrometry showed that PDX is a double lipoxygenation product. Its structure differs from PD1, with
E,Z,E geometry (PDX) instead of
E,E,Z (PD1) and S configuration at carbon 10 instead of R. PDX inhibits human blood platelet aggregation at sub-micromolar concentrations.</description><subject>10,17-Dihydroxy-docosahexaenoic acid</subject><subject>15-Lipoxygenase</subject><subject>Arachidonate 15-Lipoxygenase</subject><subject>Arachidonate 15-Lipoxygenase - metabolism</subject><subject>BSTFA</subject><subject>Carbon</subject><subject>Carbon - chemistry</subject><subject>DHA</subject><subject>Docosahexaenoic acid</subject><subject>Docosahexaenoic Acids</subject><subject>Docosahexaenoic Acids - chemistry</subject><subject>Docosahexaenoic Acids - metabolism</subject><subject>Docosahexaenoic Acids - pharmacology</subject><subject>Dose-Response Relationship, Drug</subject><subject>Double lipoxygenation</subject><subject>Food and Nutrition</subject><subject>Gas Chromatography-Mass Spectrometry</subject><subject>Glycine max - enzymology</subject><subject>heptafluorobutyryl imidazole</subject><subject>HFBI</subject><subject>Humans</subject><subject>Hydroxides</subject><subject>Hydroxides - chemistry</subject><subject>Ion mobility separation</subject><subject>Life Sciences</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>N,O-Bis(trimethylsilyl)-trifluroroacetamide</subject><subject>Platelet Aggregation</subject><subject>Platelet Aggregation - drug effects</subject><subject>sLOX</subject><subject>soybean lipoxygenase</subject><subject>Soybeans</subject><subject>Stereoisomerism</subject><issn>0014-5793</issn><issn>1873-3468</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNqNkU2P0zAQhi0EYsvCTwD5xKnpjuNs4pzQfpUiVQIJkLhZjj1pXTlxsZNdLb8eh1TLEU4ej5555-Ml5C2DFQNWXhxWLTbR4bDKAeqUWwEUz8iCiYpnvCjFc7IAYEV2WdX8jLyK8QDpL1j9kpyxWiSuYgvSrUfnqN6roPSAwf5Sg_U99S39cvtjSRXtcQz-GPyAerD9xVNEbxm10XcYlvRhb_We2n5vGztE2jjvDT06NWCaj6rdLuDuj-5r8qJVLuKb03tOvq_vvt1ssu3nj59urraZLtNyWVG0HIDrXGsFuQCooGoNN01T6sqIVjOmRM2xbQwH0RoUujSsAC2gBq0afk6Ws-5eOXkMtlPhUXpl5eZqK20fMXQynSuveZ7fs4S_n_G03c8R4yA7GzU6p3r0Y5Q5Y0VVlHkCL2dQBx9jwPZJnIGcbJEHebJFTrZM6dQn1b07NRibDs3fqpMPCdjMwIN1-Ph_qnJ9d51_nTyeLE6bQ1UVk9SHWQrTge8tBhm1xV6jsSE5J423_5j2N1BRt3c</recordid><startdate>20091103</startdate><enddate>20091103</enddate><creator>Chen, P.</creator><creator>Fenet, B.</creator><creator>Michaud, S.</creator><creator>Tomczyk, N.</creator><creator>Véricel, E.</creator><creator>Lagarde, M.</creator><creator>Guichardant, M.</creator><general>Elsevier B.V</general><general>Wiley</general><scope>6I.</scope><scope>AAFTH</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>7TK</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0002-8068-1891</orcidid></search><sort><creationdate>20091103</creationdate><title>Full characterization of PDX, a neuroprotectin/protectin D1 isomer, which inhibits blood platelet aggregation</title><author>Chen, P. ; Fenet, B. ; Michaud, S. ; Tomczyk, N. ; Véricel, E. ; Lagarde, M. ; Guichardant, M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c6101-44f3003c2cca02800707fd3dbb6c7d8fc11a893efbd308fde8c6d140c8090cab3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>10,17-Dihydroxy-docosahexaenoic acid</topic><topic>15-Lipoxygenase</topic><topic>Arachidonate 15-Lipoxygenase</topic><topic>Arachidonate 15-Lipoxygenase - metabolism</topic><topic>BSTFA</topic><topic>Carbon</topic><topic>Carbon - chemistry</topic><topic>DHA</topic><topic>Docosahexaenoic acid</topic><topic>Docosahexaenoic Acids</topic><topic>Docosahexaenoic Acids - chemistry</topic><topic>Docosahexaenoic Acids - metabolism</topic><topic>Docosahexaenoic Acids - pharmacology</topic><topic>Dose-Response Relationship, Drug</topic><topic>Double lipoxygenation</topic><topic>Food and Nutrition</topic><topic>Gas Chromatography-Mass Spectrometry</topic><topic>Glycine max - enzymology</topic><topic>heptafluorobutyryl imidazole</topic><topic>HFBI</topic><topic>Humans</topic><topic>Hydroxides</topic><topic>Hydroxides - chemistry</topic><topic>Ion mobility separation</topic><topic>Life Sciences</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>N,O-Bis(trimethylsilyl)-trifluroroacetamide</topic><topic>Platelet Aggregation</topic><topic>Platelet Aggregation - drug effects</topic><topic>sLOX</topic><topic>soybean lipoxygenase</topic><topic>Soybeans</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, P.</creatorcontrib><creatorcontrib>Fenet, B.</creatorcontrib><creatorcontrib>Michaud, S.</creatorcontrib><creatorcontrib>Tomczyk, N.</creatorcontrib><creatorcontrib>Véricel, E.</creatorcontrib><creatorcontrib>Lagarde, M.</creatorcontrib><creatorcontrib>Guichardant, M.</creatorcontrib><collection>ScienceDirect Open Access Titles</collection><collection>Elsevier:ScienceDirect:Open Access</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>FEBS letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, P.</au><au>Fenet, B.</au><au>Michaud, S.</au><au>Tomczyk, N.</au><au>Véricel, E.</au><au>Lagarde, M.</au><au>Guichardant, M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Full characterization of PDX, a neuroprotectin/protectin D1 isomer, which inhibits blood platelet aggregation</atitle><jtitle>FEBS letters</jtitle><addtitle>FEBS Lett</addtitle><date>2009-11-03</date><risdate>2009</risdate><volume>583</volume><issue>21</issue><spage>3478</spage><epage>3484</epage><pages>3478-3484</pages><issn>0014-5793</issn><eissn>1873-3468</eissn><abstract>Our study aimed to establish the complete structure of the main dihydroxy conjugated triene issued from the lipoxygenation (soybean enzyme) of docosahexaenoic acid, named PDX, an isomer of protectin/neuroprotectin D1 (PD1/NPD1) described by Bazan and Serhan. NMR approaches and other chemical characterization (e.g. GC–MS, HPLC and LC–MS/MS) indicated that PDX is 10(S),17(S)-dihydroxy-docosahexa-4
Z,7
Z,11
E,13
Z,15
E,19
Z-enoic acid. The use of
18O
2 and mass spectrometry showed that PDX is a double lipoxygenation product. Its structure differs from PD1, with
E,Z,E geometry (PDX) instead of
E,E,Z (PD1) and S configuration at carbon 10 instead of R. PDX inhibits human blood platelet aggregation at sub-micromolar concentrations.</abstract><cop>England</cop><pub>Elsevier B.V</pub><pmid>19818771</pmid><doi>10.1016/j.febslet.2009.10.004</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0002-8068-1891</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0014-5793 |
| ispartof | FEBS letters, 2009-11, Vol.583 (21), p.3478-3484 |
| issn | 0014-5793 1873-3468 |
| language | eng |
| recordid | cdi_hal_primary_oai_HAL_inserm_00429322v1 |
| source | Wiley; ScienceDirect Journals |
| subjects | 10,17-Dihydroxy-docosahexaenoic acid 15-Lipoxygenase Arachidonate 15-Lipoxygenase Arachidonate 15-Lipoxygenase - metabolism BSTFA Carbon Carbon - chemistry DHA Docosahexaenoic acid Docosahexaenoic Acids Docosahexaenoic Acids - chemistry Docosahexaenoic Acids - metabolism Docosahexaenoic Acids - pharmacology Dose-Response Relationship, Drug Double lipoxygenation Food and Nutrition Gas Chromatography-Mass Spectrometry Glycine max - enzymology heptafluorobutyryl imidazole HFBI Humans Hydroxides Hydroxides - chemistry Ion mobility separation Life Sciences Magnetic Resonance Spectroscopy N,O-Bis(trimethylsilyl)-trifluroroacetamide Platelet Aggregation Platelet Aggregation - drug effects sLOX soybean lipoxygenase Soybeans Stereoisomerism |
| title | Full characterization of PDX, a neuroprotectin/protectin D1 isomer, which inhibits blood platelet aggregation |
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