Free radical oxidation (autoxidation) of alkenones and other lipids in cells of Emiliania huxleyi
Identifieur interne : 003D20 ( PascalFrancis/Corpus ); précédent : 003D19; suivant : 003D21Free radical oxidation (autoxidation) of alkenones and other lipids in cells of Emiliania huxleyi
Auteurs : Jean-Francois Rontani ; Ian Jameson ; Stéphane Christodoulou ; John K. VolkmanSource :
- Phytochemistry [ 0031-9422 ] ; 2007.
Descripteurs français
- Pascal (Inist)
English descriptors
- KwdEn :
Abstract
Cells of the coccolithophorid Emiliania huxleyi strain CS-57 grown under an atmosphere of air + 0.5% CO2 showed oxidative damage after 10 days growth with concomitant and major changes to the lipid composition. The fatty acid profile was strongly altered and lacked appreciable amounts of the polyunsaturated fatty acids (PUFA: C18:5, C18:3 and C22:6) typical of healthy cells. Oxidation products of these PUFA could not be detected, but monounsaturated fatty acids proved to be good indicators of oxidative processes. The presence (after NaBH4-reduction) of a high proportion of 1 -hydroxyoctadec-cis-9-enoic and 8-hydroxyoctadec-cis-9-enoic acids showed that the degradation of oleic acid involved mainly free radical oxidation processes (70-75% autoxidation and 20-25% photooxidation). We also detected large amounts of degradation products of the oxidation product 9,10-epoxyoctadecanoic acid including diols, methoxyhydrins and chlorohydrins. These oxidative effects were found in all the lipid classes examined. Products included significant amounts of chlorophyll side-chain autooxidation products Z- and E-3,7, 11,15-tetramethylhexadec-3-ene-1,2-diols and Z-and E-3,7, 11,15-tetramethylhexadec-2-ene-1,4-diols, while phytyldiol was present in relatively low proportions. Δ5-3β,7-epimeric unsaturated steroidal diols arising from the autooxidation of the Δ5 double bond of epi-brassicasterol and minor amounts of Δ4-3β,6-diols were also detected. Long-chain unsaturated ketone (alkenone) content per cell was much higher in the presence of 0.5% CO2 likely due to carbon storage under these conditions. The proportions of di- and tri-unsaturated alkenones was relatively stable throughout the growth cycle in the absence of additional CO2, but not when grown with 0.5% CO2. The detection of characteristic alkenone autoxidation products in cells grown under these latter conditions allowed us to attribute the significant increase in index observed to the involvement of free radical oxidation processes.
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Pour connaître la documentation sur le format Inist Standard.
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Format Inist (serveur)
NO : | PASCAL 07-0171394 INIST |
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ET : | Free radical oxidation (autoxidation) of alkenones and other lipids in cells of Emiliania huxleyi |
AU : | RONTANI (Jean-Francois); JAMESON (Ian); CHRISTODOULOU (Stéphane); VOLKMAN (John K.) |
AF : | Laboratoire de Microbiologie Géochimie et Ecologie Marines (UMR 6117), Centre d'Océanologie de Marseille (OSU), Campus de Luminy, case 901/13288 Marseille/France (1 aut., 3 aut.); CSIRO Marine and Atmospheric Research, GPO Box 1538/Hobart, Tasmania 7001/Australie (2 aut., 4 aut.) |
DT : | Publication en série; Niveau analytique |
SO : | Phytochemistry; ISSN 0031-9422; Pays-Bas; Da. 2007; Vol. 68; No. 6; Pp. 913-924; Bibl. 1 p.1/4 |
LA : | Anglais |
EA : | Cells of the coccolithophorid Emiliania huxleyi strain CS-57 grown under an atmosphere of air + 0.5% CO2 showed oxidative damage after 10 days growth with concomitant and major changes to the lipid composition. The fatty acid profile was strongly altered and lacked appreciable amounts of the polyunsaturated fatty acids (PUFA: C18:5, C18:3 and C22:6) typical of healthy cells. Oxidation products of these PUFA could not be detected, but monounsaturated fatty acids proved to be good indicators of oxidative processes. The presence (after NaBH4-reduction) of a high proportion of 1 -hydroxyoctadec-cis-9-enoic and 8-hydroxyoctadec-cis-9-enoic acids showed that the degradation of oleic acid involved mainly free radical oxidation processes (70-75% autoxidation and 20-25% photooxidation). We also detected large amounts of degradation products of the oxidation product 9,10-epoxyoctadecanoic acid including diols, methoxyhydrins and chlorohydrins. These oxidative effects were found in all the lipid classes examined. Products included significant amounts of chlorophyll side-chain autooxidation products Z- and E-3,7, 11,15-tetramethylhexadec-3-ene-1,2-diols and Z-and E-3,7, 11,15-tetramethylhexadec-2-ene-1,4-diols, while phytyldiol was present in relatively low proportions. Δ5-3β,7-epimeric unsaturated steroidal diols arising from the autooxidation of the Δ5 double bond of epi-brassicasterol and minor amounts of Δ4-3β,6-diols were also detected. Long-chain unsaturated ketone (alkenone) content per cell was much higher in the presence of 0.5% CO2 likely due to carbon storage under these conditions. The proportions of di- and tri-unsaturated alkenones was relatively stable throughout the growth cycle in the absence of additional CO2, but not when grown with 0.5% CO2. The detection of characteristic alkenone autoxidation products in cells grown under these latter conditions allowed us to attribute the significant increase in index observed to the involvement of free radical oxidation processes. |
CC : | 002A10D; 002A10E01 |
FD : | Radical libre; Oxydation; Autooxydation; Lipide; Souche; Croissance; Acide gras; Acide gras polyinsaturé; Réduction; Carbone dioxyde; Oléique acide; Photooxydation; Produit dégradation; Diol; Chlorophylle; Stéroïde; Chaîne longue; EC 6.3.3.1 |
ED : | Free radical; Oxidation; Autoxidation; Lipids; Strain; Growth; Fatty acids; Polyunsaturated fatty acid; Reduction; Carbon dioxide; Oleic acid; Photooxidation; Degradation product; Diol; Chlorophyll; Steroid; Long chain; EC 6.3.3.1 |
SD : | Radical libre; Oxidación; Autooxidación; Lípido; Cepa; Crecimiento; Acido graso; Acido graso poliinsaturado; Reducción; Carbono dióxido; Oleico ácido; Fotooxidación; Producto degradación; Diol; Clorofila; Esteroide; Cadena larga |
LO : | INIST-9408.354000143562740200 |
ID : | 07-0171394 |
Links to Exploration step
Pascal:07-0171394Le document en format XML
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<term>Degradation product</term>
<term>Diol</term>
<term>EC 6.3.3.1</term>
<term>Fatty acids</term>
<term>Free radical</term>
<term>Growth</term>
<term>Lipids</term>
<term>Long chain</term>
<term>Oleic acid</term>
<term>Oxidation</term>
<term>Photooxidation</term>
<term>Polyunsaturated fatty acid</term>
<term>Reduction</term>
<term>Steroid</term>
<term>Strain</term>
</keywords>
<keywords scheme="Pascal" xml:lang="fr"><term>Radical libre</term>
<term>Oxydation</term>
<term>Autooxydation</term>
<term>Lipide</term>
<term>Souche</term>
<term>Croissance</term>
<term>Acide gras</term>
<term>Acide gras polyinsaturé</term>
<term>Réduction</term>
<term>Carbone dioxyde</term>
<term>Oléique acide</term>
<term>Photooxydation</term>
<term>Produit dégradation</term>
<term>Diol</term>
<term>Chlorophylle</term>
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<term>Chaîne longue</term>
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<front><div type="abstract" xml:lang="en">Cells of the coccolithophorid Emiliania huxleyi strain CS-57 grown under an atmosphere of air + 0.5% CO<sub>2</sub>
showed oxidative damage after 10 days growth with concomitant and major changes to the lipid composition. The fatty acid profile was strongly altered and lacked appreciable amounts of the polyunsaturated fatty acids (PUFA: C18:5, C18:3 and C<sub>22:6</sub>
) typical of healthy cells. Oxidation products of these PUFA could not be detected, but monounsaturated fatty acids proved to be good indicators of oxidative processes. The presence (after NaBH<sub>4</sub>
-reduction) of a high proportion of 1 -hydroxyoctadec-cis-9-enoic and 8-hydroxyoctadec-cis-9-enoic acids showed that the degradation of oleic acid involved mainly free radical oxidation processes (70-75% autoxidation and 20-25% photooxidation). We also detected large amounts of degradation products of the oxidation product 9,10-epoxyoctadecanoic acid including diols, methoxyhydrins and chlorohydrins. These oxidative effects were found in all the lipid classes examined. Products included significant amounts of chlorophyll side-chain autooxidation products Z- and E-3,7, 11,15-tetramethylhexadec-3-ene-1,2-diols and Z-and E-3,7, 11,15-tetramethylhexadec-2-ene-1,4-diols, while phytyldiol was present in relatively low proportions. Δ<sup>5</sup>
-3β,7-epimeric unsaturated steroidal diols arising from the autooxidation of the Δ<sup>5</sup>
double bond of epi-brassicasterol and minor amounts of Δ<sup>4</sup>
-3β,6-diols were also detected. Long-chain unsaturated ketone (alkenone) content per cell was much higher in the presence of 0.5% CO<sub>2</sub>
likely due to carbon storage under these conditions. The proportions of di- and tri-unsaturated alkenones was relatively stable throughout the growth cycle in the absence of additional CO<sub>2</sub>
, but not when grown with 0.5% CO<sub>2</sub>
. The detection of characteristic alkenone autoxidation products in cells grown under these latter conditions allowed us to attribute the significant increase in index observed to the involvement of free radical oxidation processes.</div>
</front>
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showed oxidative damage after 10 days growth with concomitant and major changes to the lipid composition. The fatty acid profile was strongly altered and lacked appreciable amounts of the polyunsaturated fatty acids (PUFA: C18:5, C18:3 and C<sub>22:6</sub>
) typical of healthy cells. Oxidation products of these PUFA could not be detected, but monounsaturated fatty acids proved to be good indicators of oxidative processes. The presence (after NaBH<sub>4</sub>
-reduction) of a high proportion of 1 -hydroxyoctadec-cis-9-enoic and 8-hydroxyoctadec-cis-9-enoic acids showed that the degradation of oleic acid involved mainly free radical oxidation processes (70-75% autoxidation and 20-25% photooxidation). We also detected large amounts of degradation products of the oxidation product 9,10-epoxyoctadecanoic acid including diols, methoxyhydrins and chlorohydrins. These oxidative effects were found in all the lipid classes examined. Products included significant amounts of chlorophyll side-chain autooxidation products Z- and E-3,7, 11,15-tetramethylhexadec-3-ene-1,2-diols and Z-and E-3,7, 11,15-tetramethylhexadec-2-ene-1,4-diols, while phytyldiol was present in relatively low proportions. Δ<sup>5</sup>
-3β,7-epimeric unsaturated steroidal diols arising from the autooxidation of the Δ<sup>5</sup>
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<s2>FX</s2>
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<s5>02</s5>
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<fC03 i1="03" i2="X" l="FRE"><s0>Autooxydation</s0>
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<s5>05</s5>
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<fC03 i1="06" i2="X" l="FRE"><s0>Croissance</s0>
<s5>06</s5>
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<s5>07</s5>
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<s5>07</s5>
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<s5>08</s5>
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<fC03 i1="08" i2="X" l="ENG"><s0>Polyunsaturated fatty acid</s0>
<s5>08</s5>
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<fC03 i1="08" i2="X" l="SPA"><s0>Acido graso poliinsaturado</s0>
<s5>08</s5>
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<fC03 i1="09" i2="X" l="FRE"><s0>Réduction</s0>
<s5>09</s5>
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<fC03 i1="09" i2="X" l="ENG"><s0>Reduction</s0>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="X" l="SPA"><s0>Reducción</s0>
<s5>09</s5>
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<fC03 i1="10" i2="X" l="FRE"><s0>Carbone dioxyde</s0>
<s2>NK</s2>
<s2>FX</s2>
<s5>15</s5>
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<fC03 i1="10" i2="X" l="ENG"><s0>Carbon dioxide</s0>
<s2>NK</s2>
<s2>FX</s2>
<s5>15</s5>
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<fC03 i1="10" i2="X" l="SPA"><s0>Carbono dióxido</s0>
<s2>NK</s2>
<s2>FX</s2>
<s5>15</s5>
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<fC03 i1="11" i2="X" l="FRE"><s0>Oléique acide</s0>
<s2>NK</s2>
<s5>16</s5>
</fC03>
<fC03 i1="11" i2="X" l="ENG"><s0>Oleic acid</s0>
<s2>NK</s2>
<s5>16</s5>
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<fC03 i1="11" i2="X" l="SPA"><s0>Oleico ácido</s0>
<s2>NK</s2>
<s5>16</s5>
</fC03>
<fC03 i1="12" i2="X" l="FRE"><s0>Photooxydation</s0>
<s5>33</s5>
</fC03>
<fC03 i1="12" i2="X" l="ENG"><s0>Photooxidation</s0>
<s5>33</s5>
</fC03>
<fC03 i1="12" i2="X" l="SPA"><s0>Fotooxidación</s0>
<s5>33</s5>
</fC03>
<fC03 i1="13" i2="X" l="FRE"><s0>Produit dégradation</s0>
<s5>34</s5>
</fC03>
<fC03 i1="13" i2="X" l="ENG"><s0>Degradation product</s0>
<s5>34</s5>
</fC03>
<fC03 i1="13" i2="X" l="SPA"><s0>Producto degradación</s0>
<s5>34</s5>
</fC03>
<fC03 i1="14" i2="X" l="FRE"><s0>Diol</s0>
<s5>35</s5>
</fC03>
<fC03 i1="14" i2="X" l="ENG"><s0>Diol</s0>
<s5>35</s5>
</fC03>
<fC03 i1="14" i2="X" l="SPA"><s0>Diol</s0>
<s5>35</s5>
</fC03>
<fC03 i1="15" i2="X" l="FRE"><s0>Chlorophylle</s0>
<s5>36</s5>
</fC03>
<fC03 i1="15" i2="X" l="ENG"><s0>Chlorophyll</s0>
<s5>36</s5>
</fC03>
<fC03 i1="15" i2="X" l="SPA"><s0>Clorofila</s0>
<s5>36</s5>
</fC03>
<fC03 i1="16" i2="X" l="FRE"><s0>Stéroïde</s0>
<s5>37</s5>
</fC03>
<fC03 i1="16" i2="X" l="ENG"><s0>Steroid</s0>
<s5>37</s5>
</fC03>
<fC03 i1="16" i2="X" l="SPA"><s0>Esteroide</s0>
<s5>37</s5>
</fC03>
<fC03 i1="17" i2="X" l="FRE"><s0>Chaîne longue</s0>
<s5>38</s5>
</fC03>
<fC03 i1="17" i2="X" l="ENG"><s0>Long chain</s0>
<s5>38</s5>
</fC03>
<fC03 i1="17" i2="X" l="SPA"><s0>Cadena larga</s0>
<s5>38</s5>
</fC03>
<fC03 i1="18" i2="X" l="FRE"><s0>EC 6.3.3.1</s0>
<s4>CD</s4>
<s5>96</s5>
</fC03>
<fC03 i1="18" i2="X" l="ENG"><s0>EC 6.3.3.1</s0>
<s4>CD</s4>
<s5>96</s5>
</fC03>
<fN21><s1>121</s1>
</fN21>
<fN44 i1="01"><s1>OTO</s1>
</fN44>
<fN82><s1>OTO</s1>
</fN82>
</pA>
</standard>
<server><NO>PASCAL 07-0171394 INIST</NO>
<ET>Free radical oxidation (autoxidation) of alkenones and other lipids in cells of Emiliania huxleyi</ET>
<AU>RONTANI (Jean-Francois); JAMESON (Ian); CHRISTODOULOU (Stéphane); VOLKMAN (John K.)</AU>
<AF>Laboratoire de Microbiologie Géochimie et Ecologie Marines (UMR 6117), Centre d'Océanologie de Marseille (OSU), Campus de Luminy, case 901/13288 Marseille/France (1 aut., 3 aut.); CSIRO Marine and Atmospheric Research, GPO Box 1538/Hobart, Tasmania 7001/Australie (2 aut., 4 aut.)</AF>
<DT>Publication en série; Niveau analytique</DT>
<SO>Phytochemistry; ISSN 0031-9422; Pays-Bas; Da. 2007; Vol. 68; No. 6; Pp. 913-924; Bibl. 1 p.1/4</SO>
<LA>Anglais</LA>
<EA>Cells of the coccolithophorid Emiliania huxleyi strain CS-57 grown under an atmosphere of air + 0.5% CO<sub>2</sub>
showed oxidative damage after 10 days growth with concomitant and major changes to the lipid composition. The fatty acid profile was strongly altered and lacked appreciable amounts of the polyunsaturated fatty acids (PUFA: C18:5, C18:3 and C<sub>22:6</sub>
) typical of healthy cells. Oxidation products of these PUFA could not be detected, but monounsaturated fatty acids proved to be good indicators of oxidative processes. The presence (after NaBH<sub>4</sub>
-reduction) of a high proportion of 1 -hydroxyoctadec-cis-9-enoic and 8-hydroxyoctadec-cis-9-enoic acids showed that the degradation of oleic acid involved mainly free radical oxidation processes (70-75% autoxidation and 20-25% photooxidation). We also detected large amounts of degradation products of the oxidation product 9,10-epoxyoctadecanoic acid including diols, methoxyhydrins and chlorohydrins. These oxidative effects were found in all the lipid classes examined. Products included significant amounts of chlorophyll side-chain autooxidation products Z- and E-3,7, 11,15-tetramethylhexadec-3-ene-1,2-diols and Z-and E-3,7, 11,15-tetramethylhexadec-2-ene-1,4-diols, while phytyldiol was present in relatively low proportions. Δ<sup>5</sup>
-3β,7-epimeric unsaturated steroidal diols arising from the autooxidation of the Δ<sup>5</sup>
double bond of epi-brassicasterol and minor amounts of Δ<sup>4</sup>
-3β,6-diols were also detected. Long-chain unsaturated ketone (alkenone) content per cell was much higher in the presence of 0.5% CO<sub>2</sub>
likely due to carbon storage under these conditions. The proportions of di- and tri-unsaturated alkenones was relatively stable throughout the growth cycle in the absence of additional CO<sub>2</sub>
, but not when grown with 0.5% CO<sub>2</sub>
. The detection of characteristic alkenone autoxidation products in cells grown under these latter conditions allowed us to attribute the significant increase in index observed to the involvement of free radical oxidation processes.</EA>
<CC>002A10D; 002A10E01</CC>
<FD>Radical libre; Oxydation; Autooxydation; Lipide; Souche; Croissance; Acide gras; Acide gras polyinsaturé; Réduction; Carbone dioxyde; Oléique acide; Photooxydation; Produit dégradation; Diol; Chlorophylle; Stéroïde; Chaîne longue; EC 6.3.3.1</FD>
<ED>Free radical; Oxidation; Autoxidation; Lipids; Strain; Growth; Fatty acids; Polyunsaturated fatty acid; Reduction; Carbon dioxide; Oleic acid; Photooxidation; Degradation product; Diol; Chlorophyll; Steroid; Long chain; EC 6.3.3.1</ED>
<SD>Radical libre; Oxidación; Autooxidación; Lípido; Cepa; Crecimiento; Acido graso; Acido graso poliinsaturado; Reducción; Carbono dióxido; Oleico ácido; Fotooxidación; Producto degradación; Diol; Clorofila; Esteroide; Cadena larga</SD>
<LO>INIST-9408.354000143562740200</LO>
<ID>07-0171394</ID>
</server>
</inist>
</record>
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