Regiospecific oxygenation of alkenones in the benthic haptophyte Chrysotila lamellosa Anand HAP 17
Two groups of previously unidentified C 37–C 39 epoxyalkenones and alkenediones were detected in late stationary cultures of Chrysotila lamellosa HAP 17. The formation of these compounds was attributed to regiospecific enzymatic processes. Two groups of previously unidentified C 37–C 39 epoxyalkenon...
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description | Two groups of previously unidentified C
37–C
39 epoxyalkenones and alkenediones were detected in late stationary cultures of
Chrysotila lamellosa HAP 17. The formation of these compounds was attributed to regiospecific enzymatic processes.
Two groups of previously unidentified C
37–C
39 epoxyalkenones and alkenediones were detected in late stationary phase cultures of the haptophyte microalga
Chrysotila lamellosa. The formation of these compounds is attributed to the involvement of enzymatic processes acting specifically on the C-21 or C-22 allylic carbon and the
ω15 double bond of methyl and ethyl alkenones respectively. Thus, the epoxyalkenones appear to be derivatives of alkenones where the
ω15 double bond is oxidized to the epoxide. These epoxyalkenones disappear as the cells age to be replaced by a series of alkenediones. The structures of these compounds indicate that they are derivatives of methyl and ethyl alkenones with an additional carbonyl group on the C-21 or C-22 carbon respectively and without the
ω15 double bond. We propose that these compounds are formed by an initial regiospecific lipoxygenase-catalyzed peroxidation of methyl and ethyl alkenones on their C-21 or C-22 allylic carbon, respectively. Lipohydroperoxidase-catalyzed homolytic cleavage of the O–O bond could then result in the formation of conjugated ketones which may then undergo a saturation reaction to form the diketones identified. This work demonstrates that alkenones can be degraded by enzymatic reactions in senescent cells, and by implication this could also occur in the natural environment. |
doi_str_mv | 10.1016/j.phytochem.2004.09.016 |
format | Article |
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37–C
39 epoxyalkenones and alkenediones were detected in late stationary cultures of
Chrysotila lamellosa HAP 17. The formation of these compounds was attributed to regiospecific enzymatic processes.
Two groups of previously unidentified C
37–C
39 epoxyalkenones and alkenediones were detected in late stationary phase cultures of the haptophyte microalga
Chrysotila lamellosa. The formation of these compounds is attributed to the involvement of enzymatic processes acting specifically on the C-21 or C-22 allylic carbon and the
ω15 double bond of methyl and ethyl alkenones respectively. Thus, the epoxyalkenones appear to be derivatives of alkenones where the
ω15 double bond is oxidized to the epoxide. These epoxyalkenones disappear as the cells age to be replaced by a series of alkenediones. The structures of these compounds indicate that they are derivatives of methyl and ethyl alkenones with an additional carbonyl group on the C-21 or C-22 carbon respectively and without the
ω15 double bond. We propose that these compounds are formed by an initial regiospecific lipoxygenase-catalyzed peroxidation of methyl and ethyl alkenones on their C-21 or C-22 allylic carbon, respectively. Lipohydroperoxidase-catalyzed homolytic cleavage of the O–O bond could then result in the formation of conjugated ketones which may then undergo a saturation reaction to form the diketones identified. This work demonstrates that alkenones can be degraded by enzymatic reactions in senescent cells, and by implication this could also occur in the natural environment.</description><identifier>ISSN: 0031-9422</identifier><identifier>EISSN: 1873-3700</identifier><identifier>DOI: 10.1016/j.phytochem.2004.09.016</identifier><identifier>PMID: 15561193</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Alkenediones ; alkenes ; Alkenones ; Biological and medical sciences ; Chemical constitution ; Chrysotila lamellosa ; Enzymatic processes ; epoxides ; Epoxyalkenones ; Eukaryota - chemistry ; Eukaryota - enzymology ; Fundamental and applied biological sciences. Psychology ; Gas Chromatography-Mass Spectrometry ; Haptophyta ; Ketones - chemistry ; Ketones - metabolism ; microalgae ; Molecular Structure ; oxidation ; Oxidation-Reduction ; Plant physiology and development ; Regiospecific oxygenation ; Senescent cells ; Time Factors</subject><ispartof>Phytochemistry (Oxford), 2004-12, Vol.65 (24), p.3269-3278</ispartof><rights>2004 Elsevier Ltd</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.phytochem.2004.09.016$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16318623$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15561193$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Rontani, Jean-François</creatorcontrib><creatorcontrib>Beker, Béatriz</creatorcontrib><creatorcontrib>Volkman, John K.</creatorcontrib><title>Regiospecific oxygenation of alkenones in the benthic haptophyte Chrysotila lamellosa Anand HAP 17</title><title>Phytochemistry (Oxford)</title><addtitle>Phytochemistry</addtitle><description>Two groups of previously unidentified C
37–C
39 epoxyalkenones and alkenediones were detected in late stationary cultures of
Chrysotila lamellosa HAP 17. The formation of these compounds was attributed to regiospecific enzymatic processes.
Two groups of previously unidentified C
37–C
39 epoxyalkenones and alkenediones were detected in late stationary phase cultures of the haptophyte microalga
Chrysotila lamellosa. The formation of these compounds is attributed to the involvement of enzymatic processes acting specifically on the C-21 or C-22 allylic carbon and the
ω15 double bond of methyl and ethyl alkenones respectively. Thus, the epoxyalkenones appear to be derivatives of alkenones where the
ω15 double bond is oxidized to the epoxide. These epoxyalkenones disappear as the cells age to be replaced by a series of alkenediones. The structures of these compounds indicate that they are derivatives of methyl and ethyl alkenones with an additional carbonyl group on the C-21 or C-22 carbon respectively and without the
ω15 double bond. We propose that these compounds are formed by an initial regiospecific lipoxygenase-catalyzed peroxidation of methyl and ethyl alkenones on their C-21 or C-22 allylic carbon, respectively. Lipohydroperoxidase-catalyzed homolytic cleavage of the O–O bond could then result in the formation of conjugated ketones which may then undergo a saturation reaction to form the diketones identified. This work demonstrates that alkenones can be degraded by enzymatic reactions in senescent cells, and by implication this could also occur in the natural environment.</description><subject>Alkenediones</subject><subject>alkenes</subject><subject>Alkenones</subject><subject>Biological and medical sciences</subject><subject>Chemical constitution</subject><subject>Chrysotila lamellosa</subject><subject>Enzymatic processes</subject><subject>epoxides</subject><subject>Epoxyalkenones</subject><subject>Eukaryota - chemistry</subject><subject>Eukaryota - enzymology</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Gas Chromatography-Mass Spectrometry</subject><subject>Haptophyta</subject><subject>Ketones - chemistry</subject><subject>Ketones - metabolism</subject><subject>microalgae</subject><subject>Molecular Structure</subject><subject>oxidation</subject><subject>Oxidation-Reduction</subject><subject>Plant physiology and development</subject><subject>Regiospecific oxygenation</subject><subject>Senescent cells</subject><subject>Time Factors</subject><issn>0031-9422</issn><issn>1873-3700</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0cGO0zAQBmALgdjuwiuwvsAtYSZOnOZYVcsu0kogYM-W44wbl8QOcYro2-OqBY6cRhp_skb_z9gtQo6A8v0-n_rjEkxPY14AlDk0edo_Yytc1yITNcBztgIQmDVlUVyx6xj3AFBVUr5kV5gmYiNWrP1COxfiRMZZZ3j4ddyR14sLngfL9fCdfPAUufN86Ym35Jc-uV5PSzidQHzbz8cYFjdoPuiRhiFEzTde-44_bD5zrF-xF1YPkV5f5g17-nD3bfuQPX66_7jdPGZUyGrJTFdhbdpGtG3ZNaiLsoSObGcstsLKyhpD1qY3Kcu21dZoCWVbQQmoTWVJ3LB353-nOfw4UFzU6KJJB2lP4RCVrDElsIb_QqyLpq6xTPDNBR7akTo1zW7U81H9iS-Btxego9GDnbU3Lv5zUuBaFid3e3ZWB6V3czJPXwtAAdDINTaYxOYsKCX009GsonHkDXVuJrOoLjiFoE7lq736W746la-gUWkvfgMZXKOB</recordid><startdate>200412</startdate><enddate>200412</enddate><creator>Rontani, Jean-François</creator><creator>Beker, Béatriz</creator><creator>Volkman, John K.</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>F1W</scope><scope>H95</scope><scope>L.G</scope><scope>M7N</scope><scope>7X8</scope></search><sort><creationdate>200412</creationdate><title>Regiospecific oxygenation of alkenones in the benthic haptophyte Chrysotila lamellosa Anand HAP 17</title><author>Rontani, Jean-François ; Beker, Béatriz ; Volkman, John K.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-e265t-cd517cb93bb4d91a2440defdcf1b3f65fcceffb4d664bbafca604b50401ac5fe3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Alkenediones</topic><topic>alkenes</topic><topic>Alkenones</topic><topic>Biological and medical sciences</topic><topic>Chemical constitution</topic><topic>Chrysotila lamellosa</topic><topic>Enzymatic processes</topic><topic>epoxides</topic><topic>Epoxyalkenones</topic><topic>Eukaryota - chemistry</topic><topic>Eukaryota - enzymology</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Gas Chromatography-Mass Spectrometry</topic><topic>Haptophyta</topic><topic>Ketones - chemistry</topic><topic>Ketones - metabolism</topic><topic>microalgae</topic><topic>Molecular Structure</topic><topic>oxidation</topic><topic>Oxidation-Reduction</topic><topic>Plant physiology and development</topic><topic>Regiospecific oxygenation</topic><topic>Senescent cells</topic><topic>Time Factors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rontani, Jean-François</creatorcontrib><creatorcontrib>Beker, Béatriz</creatorcontrib><creatorcontrib>Volkman, John K.</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</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>Phytochemistry (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rontani, Jean-François</au><au>Beker, Béatriz</au><au>Volkman, John K.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regiospecific oxygenation of alkenones in the benthic haptophyte Chrysotila lamellosa Anand HAP 17</atitle><jtitle>Phytochemistry (Oxford)</jtitle><addtitle>Phytochemistry</addtitle><date>2004-12</date><risdate>2004</risdate><volume>65</volume><issue>24</issue><spage>3269</spage><epage>3278</epage><pages>3269-3278</pages><issn>0031-9422</issn><eissn>1873-3700</eissn><abstract>Two groups of previously unidentified C
37–C
39 epoxyalkenones and alkenediones were detected in late stationary cultures of
Chrysotila lamellosa HAP 17. The formation of these compounds was attributed to regiospecific enzymatic processes.
Two groups of previously unidentified C
37–C
39 epoxyalkenones and alkenediones were detected in late stationary phase cultures of the haptophyte microalga
Chrysotila lamellosa. The formation of these compounds is attributed to the involvement of enzymatic processes acting specifically on the C-21 or C-22 allylic carbon and the
ω15 double bond of methyl and ethyl alkenones respectively. Thus, the epoxyalkenones appear to be derivatives of alkenones where the
ω15 double bond is oxidized to the epoxide. These epoxyalkenones disappear as the cells age to be replaced by a series of alkenediones. The structures of these compounds indicate that they are derivatives of methyl and ethyl alkenones with an additional carbonyl group on the C-21 or C-22 carbon respectively and without the
ω15 double bond. We propose that these compounds are formed by an initial regiospecific lipoxygenase-catalyzed peroxidation of methyl and ethyl alkenones on their C-21 or C-22 allylic carbon, respectively. Lipohydroperoxidase-catalyzed homolytic cleavage of the O–O bond could then result in the formation of conjugated ketones which may then undergo a saturation reaction to form the diketones identified. This work demonstrates that alkenones can be degraded by enzymatic reactions in senescent cells, and by implication this could also occur in the natural environment.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>15561193</pmid><doi>10.1016/j.phytochem.2004.09.016</doi><tpages>10</tpages></addata></record> |
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subjects | Alkenediones alkenes Alkenones Biological and medical sciences Chemical constitution Chrysotila lamellosa Enzymatic processes epoxides Epoxyalkenones Eukaryota - chemistry Eukaryota - enzymology Fundamental and applied biological sciences. Psychology Gas Chromatography-Mass Spectrometry Haptophyta Ketones - chemistry Ketones - metabolism microalgae Molecular Structure oxidation Oxidation-Reduction Plant physiology and development Regiospecific oxygenation Senescent cells Time Factors |
title | Regiospecific oxygenation of alkenones in the benthic haptophyte Chrysotila lamellosa Anand HAP 17 |
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