Autoxidative and Photooxidative Reactivity of Highly Branched Isoprenoid (HBI) Alkenes
Autoxidation of several mono-, di-, tri- and tetra-unsaturated highly branched isoprenoid (HBI) alkenes was induced in organic solvents using a radical initiator and enhancer, and their degradation rates were compared to those of classical phytoplanktonic lipids (mono-unsaturated fatty acids, sterol...
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ftccsdartic:oai:HAL:hal-01308379v1 2023-05-15T13:42:37+02:00 Autoxidative and Photooxidative Reactivity of Highly Branched Isoprenoid (HBI) Alkenes RONTANI, Jean-francois Belt, S. t. VAULTIER, Frederic Brown, T. a. Masse, G. Institut méditerranéen d'océanologie (MIO) Institut de Recherche pour le Développement (IRD)-Aix Marseille Université (AMU)-Institut national des sciences de l'Univers (INSU - CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université de Toulon (UTLN) 2014-05 https://hal.archives-ouvertes.fr/hal-01308379 https://doi.org/10.1007/s11745-014-3891-x en eng HAL CCSD Springer Verlag info:eu-repo/semantics/altIdentifier/doi/10.1007/s11745-014-3891-x hal-01308379 https://hal.archives-ouvertes.fr/hal-01308379 doi:10.1007/s11745-014-3891-x ISSN: 0024-4201 EISSN: 1558-9307 Lipids https://hal.archives-ouvertes.fr/hal-01308379 Lipids, Springer Verlag, 2014, 49 (5), pp.481-494. ⟨10.1007/s11745-014-3891-x⟩ HBI alkenes Autoxidation Photooxidation Kinetic Senescent diatom cells Specific tracers [CHIM.ORGA]Chemical Sciences/Organic chemistry [SDU.OCEAN]Sciences of the Universe [physics]/Ocean Atmosphere info:eu-repo/semantics/article Journal articles 2014 ftccsdartic https://doi.org/10.1007/s11745-014-3891-x 2021-10-24T10:28:40Z Autoxidation of several mono-, di-, tri- and tetra-unsaturated highly branched isoprenoid (HBI) alkenes was induced in organic solvents using a radical initiator and enhancer, and their degradation rates were compared to those of classical phytoplanktonic lipids (mono-unsaturated fatty acids, sterols and chlorophyll phytyl side-chain). Autoxidation of two HBI trienes was also investigated in senescent and highly photodegraded diatom cells, collected in the Antarctic, using Fe2+ ions as radical inducers. Autoxidation rates of HBI alkenes were found to increase with the number of tri-substituted double bonds, as expected. Further, HBI trienes possessing one bis-allylic position (where hydrogen abstraction is highly favoured) were found to be particularly reactive towards autoxidation and degraded at similar rates compared to polyunsaturated fatty acids in diatom cells. By comparison of the autoxidation products of the most reactive tri-unsaturated HBI with the corresponding photooxidation products, some specific tracers of these two types of abiotic degradation processes were identified. The lack of reactivity of the mono-unsaturated HBI IP25 and a structurally similar di-unsaturated HBI towards autoxidative degradation supports the good preservation of these biomarkers in marine sediments. Article in Journal/Newspaper Antarc* Antarctic Archive ouverte HAL (Hyper Article en Ligne, CCSD - Centre pour la Communication Scientifique Directe) Antarctic The Antarctic Lipids 49 5 481 494 |
institution |
Open Polar |
collection |
Archive ouverte HAL (Hyper Article en Ligne, CCSD - Centre pour la Communication Scientifique Directe) |
op_collection_id |
ftccsdartic |
language |
English |
topic |
HBI alkenes Autoxidation Photooxidation Kinetic Senescent diatom cells Specific tracers [CHIM.ORGA]Chemical Sciences/Organic chemistry [SDU.OCEAN]Sciences of the Universe [physics]/Ocean Atmosphere |
spellingShingle |
HBI alkenes Autoxidation Photooxidation Kinetic Senescent diatom cells Specific tracers [CHIM.ORGA]Chemical Sciences/Organic chemistry [SDU.OCEAN]Sciences of the Universe [physics]/Ocean Atmosphere RONTANI, Jean-francois Belt, S. t. VAULTIER, Frederic Brown, T. a. Masse, G. Autoxidative and Photooxidative Reactivity of Highly Branched Isoprenoid (HBI) Alkenes |
topic_facet |
HBI alkenes Autoxidation Photooxidation Kinetic Senescent diatom cells Specific tracers [CHIM.ORGA]Chemical Sciences/Organic chemistry [SDU.OCEAN]Sciences of the Universe [physics]/Ocean Atmosphere |
description |
Autoxidation of several mono-, di-, tri- and tetra-unsaturated highly branched isoprenoid (HBI) alkenes was induced in organic solvents using a radical initiator and enhancer, and their degradation rates were compared to those of classical phytoplanktonic lipids (mono-unsaturated fatty acids, sterols and chlorophyll phytyl side-chain). Autoxidation of two HBI trienes was also investigated in senescent and highly photodegraded diatom cells, collected in the Antarctic, using Fe2+ ions as radical inducers. Autoxidation rates of HBI alkenes were found to increase with the number of tri-substituted double bonds, as expected. Further, HBI trienes possessing one bis-allylic position (where hydrogen abstraction is highly favoured) were found to be particularly reactive towards autoxidation and degraded at similar rates compared to polyunsaturated fatty acids in diatom cells. By comparison of the autoxidation products of the most reactive tri-unsaturated HBI with the corresponding photooxidation products, some specific tracers of these two types of abiotic degradation processes were identified. The lack of reactivity of the mono-unsaturated HBI IP25 and a structurally similar di-unsaturated HBI towards autoxidative degradation supports the good preservation of these biomarkers in marine sediments. |
author2 |
Institut méditerranéen d'océanologie (MIO) Institut de Recherche pour le Développement (IRD)-Aix Marseille Université (AMU)-Institut national des sciences de l'Univers (INSU - CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université de Toulon (UTLN) |
format |
Article in Journal/Newspaper |
author |
RONTANI, Jean-francois Belt, S. t. VAULTIER, Frederic Brown, T. a. Masse, G. |
author_facet |
RONTANI, Jean-francois Belt, S. t. VAULTIER, Frederic Brown, T. a. Masse, G. |
author_sort |
RONTANI, Jean-francois |
title |
Autoxidative and Photooxidative Reactivity of Highly Branched Isoprenoid (HBI) Alkenes |
title_short |
Autoxidative and Photooxidative Reactivity of Highly Branched Isoprenoid (HBI) Alkenes |
title_full |
Autoxidative and Photooxidative Reactivity of Highly Branched Isoprenoid (HBI) Alkenes |
title_fullStr |
Autoxidative and Photooxidative Reactivity of Highly Branched Isoprenoid (HBI) Alkenes |
title_full_unstemmed |
Autoxidative and Photooxidative Reactivity of Highly Branched Isoprenoid (HBI) Alkenes |
title_sort |
autoxidative and photooxidative reactivity of highly branched isoprenoid (hbi) alkenes |
publisher |
HAL CCSD |
publishDate |
2014 |
url |
https://hal.archives-ouvertes.fr/hal-01308379 https://doi.org/10.1007/s11745-014-3891-x |
geographic |
Antarctic The Antarctic |
geographic_facet |
Antarctic The Antarctic |
genre |
Antarc* Antarctic |
genre_facet |
Antarc* Antarctic |
op_source |
ISSN: 0024-4201 EISSN: 1558-9307 Lipids https://hal.archives-ouvertes.fr/hal-01308379 Lipids, Springer Verlag, 2014, 49 (5), pp.481-494. ⟨10.1007/s11745-014-3891-x⟩ |
op_relation |
info:eu-repo/semantics/altIdentifier/doi/10.1007/s11745-014-3891-x hal-01308379 https://hal.archives-ouvertes.fr/hal-01308379 doi:10.1007/s11745-014-3891-x |
op_doi |
https://doi.org/10.1007/s11745-014-3891-x |
container_title |
Lipids |
container_volume |
49 |
container_issue |
5 |
container_start_page |
481 |
op_container_end_page |
494 |
_version_ |
1766170195100958720 |