AustralieFrV1, PascalFrancis, Corpus, bibRecord, 004B63

Regiospecific oxygenation of alkenones in the benthic haptophyte Chrysotila lamellosa anand HAP 17

Identifieur interne : 004B63 ( PascalFrancis/Corpus ); précédent : 004B62; suivant : 004B64

Regiospecific oxygenation of alkenones in the benthic haptophyte Chrysotila lamellosa anand HAP 17

Auteurs : Jean-Francois Rontani ; Béatriz Beker ; John K. Volkman

Source :

Phytochemistry [ 0031-9422 ] ; 2004.

RBID : Pascal:05-0029564

Descripteurs français

Pascal (Inist)
- Carbone, Epoxyde, Structure moléculaire, Peroxydation, Clivage, Cétone, Dicétone, Réaction enzymatique.

English descriptors

KwdEn :
- Carbon, Cleavage, Diketone, Enzymatic reaction, Epoxide, Ketone, Molecular structure, Peroxidation.

Abstract

Two groups of previously unidentified C₃₇-C₃₉ 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 0-0 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.

Notice en format standard (ISO 2709)

Pour connaître la documentation sur le format Inist Standard.

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A08	`01`	`1`	`ENG`	`@1 Regiospecific oxygenation of alkenones in the benthic haptophyte Chrysotila lamellosa anand HAP 17`
A11	`01`	`1`		`@1 RONTANI (Jean-Francois)`
A11	`02`	`1`		`@1 BEKER (Béatriz)`
A11	`03`	`1`		`@1 VOLKMAN (John K.)`
A14	`01`			`@1 Laboratoire de Microbiologie de Biogéochimie et d'Ecologie Microbienne (UMR CNRS 6117), Centre d'Océanologie de Marseille (OSU), Campus de Luminy, Case 901 @2 13288 Marseille @3 FRA @Z 1 aut.`
A14	`02`			`@1 Centre d'Océanologie de Marseille (OSU), Station Marine d'Endoume @2 13007 Marseille @3 FRA @Z 2 aut.`
A14	`03`			`@1 CSIRO Marine Research, GPO Box 1538 @2 Hobart, Tasmania 7001 @3 AUS @Z 3 aut.`
A20				`@1 3269-3278`
A21				`@1 2004`
A23	`01`			`@0 ENG`
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A44				`@0 0000 @1 © 2005 INIST-CNRS. All rights reserved.`
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A47	`01`	`1`		`@0 05-0029564`
A60				`@1 P`
A61				`@0 A`
A64	`01`	`1`		`@0 Phytochemistry`
A66	`01`			`@0 NLD`
C01	`01`		`ENG`	@0 Two groups of previously unidentified C₃₇-C₃₉ 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 0-0 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.
C02	`01`	`X`		`@0 002A10D`
C03	`01`	`X`	`FRE`	`@0 Carbone @2 NC @5 01`
C03	`01`	`X`	`ENG`	`@0 Carbon @2 NC @5 01`
C03	`01`	`X`	`SPA`	`@0 Carbono @2 NC @5 01`
C03	`02`	`X`	`FRE`	`@0 Epoxyde @5 02`
C03	`02`	`X`	`ENG`	`@0 Epoxide @5 02`
C03	`02`	`X`	`SPA`	`@0 Epóxido @5 02`
C03	`03`	`X`	`FRE`	`@0 Structure moléculaire @5 03`
C03	`03`	`X`	`ENG`	`@0 Molecular structure @5 03`
C03	`03`	`X`	`SPA`	`@0 Estructura molecular @5 03`
C03	`04`	`X`	`FRE`	`@0 Peroxydation @5 04`
C03	`04`	`X`	`ENG`	`@0 Peroxidation @5 04`
C03	`04`	`X`	`SPA`	`@0 Peroxidación @5 04`
C03	`05`	`X`	`FRE`	`@0 Clivage @5 05`
C03	`05`	`X`	`ENG`	`@0 Cleavage @5 05`
C03	`05`	`X`	`SPA`	`@0 Clivaje @5 05`
C03	`06`	`X`	`FRE`	`@0 Cétone @5 06`
C03	`06`	`X`	`ENG`	`@0 Ketone @5 06`
C03	`06`	`X`	`SPA`	`@0 Cetona @5 06`
C03	`07`	`X`	`FRE`	`@0 Dicétone @5 07`
C03	`07`	`X`	`ENG`	`@0 Diketone @5 07`
C03	`07`	`X`	`SPA`	`@0 Dicetona @5 07`
C03	`08`	`X`	`FRE`	`@0 Réaction enzymatique @5 08`
C03	`08`	`X`	`ENG`	`@0 Enzymatic reaction @5 08`
C03	`08`	`X`	`SPA`	`@0 Reacción enzimática @5 08`
N21				`@1 010`
N44	`01`			`@1 OTO`
N82				`@1 OTO`

Format Inist (serveur)

NO :	PASCAL 05-0029564 INIST
ET :	Regiospecific oxygenation of alkenones in the benthic haptophyte Chrysotila lamellosa anand HAP 17
AU :	RONTANI (Jean-Francois); BEKER (Béatriz); VOLKMAN (John K.)
AF :	Laboratoire de Microbiologie de Biogéochimie et d'Ecologie Microbienne (UMR CNRS 6117), Centre d'Océanologie de Marseille (OSU), Campus de Luminy, Case 901/13288 Marseille/France (1 aut.); Centre d'Océanologie de Marseille (OSU), Station Marine d'Endoume/13007 Marseille/France (2 aut.); CSIRO Marine Research, GPO Box 1538/Hobart, Tasmania 7001/Australie (3 aut.)
DT :	Publication en série; Niveau analytique
SO :	Phytochemistry; ISSN 0031-9422; Pays-Bas; Da. 2004; Vol. 65; No. 24; Pp. 3269-3278; Bibl. 1 p.1/4
LA :	Anglais
EA :	Two groups of previously unidentified C₃₇-C₃₉ 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 0-0 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.
CC :	002A10D
FD :	Carbone; Epoxyde; Structure moléculaire; Peroxydation; Clivage; Cétone; Dicétone; Réaction enzymatique
ED :	Carbon; Epoxide; Molecular structure; Peroxidation; Cleavage; Ketone; Diketone; Enzymatic reaction
SD :	Carbono; Epóxido; Estructura molecular; Peroxidación; Clivaje; Cetona; Dicetona; Reacción enzimática
LO :	INIST-9408.354000122837850110
ID :	05-0029564

Links to Exploration step

Pascal:05-0029564

Le document en format XML

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<front><div type="abstract" xml:lang="en">Two groups of previously unidentified C<sub>37</sub>
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 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 0-0 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.</s0>
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<server><NO>PASCAL 05-0029564 INIST</NO>
<ET>Regiospecific oxygenation of alkenones in the benthic haptophyte Chrysotila lamellosa anand HAP 17</ET>
<AU>RONTANI (Jean-Francois); BEKER (Béatriz); VOLKMAN (John K.)</AU>
<AF>Laboratoire de Microbiologie de Biogéochimie et d'Ecologie Microbienne (UMR CNRS 6117), Centre d'Océanologie de Marseille (OSU), Campus de Luminy, Case 901/13288 Marseille/France (1 aut.); Centre d'Océanologie de Marseille (OSU), Station Marine d'Endoume/13007 Marseille/France (2 aut.); CSIRO Marine Research, GPO Box 1538/Hobart, Tasmania 7001/Australie (3 aut.)</AF>
<DT>Publication en série; Niveau analytique</DT>
<SO>Phytochemistry; ISSN 0031-9422; Pays-Bas; Da. 2004; Vol. 65; No. 24; Pp. 3269-3278; Bibl. 1 p.1/4</SO>
<LA>Anglais</LA>
<EA>Two groups of previously unidentified C<sub>37</sub>
-C<sub>39</sub>
 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 0-0 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.</EA>
<CC>002A10D</CC>
<FD>Carbone; Epoxyde; Structure moléculaire; Peroxydation; Clivage; Cétone; Dicétone; Réaction enzymatique</FD>
<ED>Carbon; Epoxide; Molecular structure; Peroxidation; Cleavage; Ketone; Diketone; Enzymatic reaction</ED>
<SD>Carbono; Epóxido; Estructura molecular; Peroxidación; Clivaje; Cetona; Dicetona; Reacción enzimática</SD>
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<ID>05-0029564</ID>
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Regiospecific oxygenation of alkenones in the benthic haptophyte Chrysotila lamellosa anand HAP 17

Regiospecific oxygenation of alkenones in the benthic haptophyte Chrysotila lamellosa anand HAP 17

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