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Article: Long-chain (C19-C29) 1-chloro-n-alkanes in leaf waxes of halophytes of the Chenopodiaceae.

Grossi, Vincent / Raphel, Danielle

2003 Volume 63, Issue 6, Page(s) 693–698

Abstract: The hydrocarbon fraction of leaf waxes of three halophytes of the Chenopodiaceae common to Mediterranean salt marshes (Suaeda vera, Sarcocornia fruticosa and Halimione portulacoides) revealed the presence of a minor series of odd and even chains 1-chloro- ...

Abstract	The hydrocarbon fraction of leaf waxes of three halophytes of the Chenopodiaceae common to Mediterranean salt marshes (Suaeda vera, Sarcocornia fruticosa and Halimione portulacoides) revealed the presence of a minor series of odd and even chains 1-chloro-n-alkanes ranging from C(19) to C(29). The identification of these new chlorinated plant constituents was based on a combination of mass spectrometry data with selective chlorine detection (CPG-AED) and was confirmed by comparison with authentic standards. The qualitative and quantitative distributions of these 1-chloro-n-alkanes varied inter-specifically. Homologues with an odd carbon-chain were predominant in all species but maximised at C(25) and C(27) in S. vera and S. fruticosa, and at C(27) and C(29) in H. portulacoides. Remarkably, 1-chloro-nonacosane was an abundant homologue only in this latter species. Leaves of S. vera contained 4 to 7 times more of total chloroalkanes than leaves of the other two species. These compounds accounted for 10, 4 and 1% of the hydrocarbon fraction of leaf waxes of S. vera, S. fruticosa and H. portulacoides, respectively. Attempts to link the occurrence of these chloroalkanes with other classes of leaf waxes (n-alkenes, n-aldehydes and n-alcohols) did not allowed a clear precursor-product relationship to be established. The biological functions as well as the mode of synthesis of alkylchlorides in (halophyte) plants remain unknown but undoubtedly deserve further attention.
MeSH term(s)	Alkanes/analysis ; Alkanes/chemistry ; Alkanes/metabolism ; Chenopodiaceae/chemistry ; Plant Leaves/chemistry ; Waxes/chemistry
Chemical Substances	Alkanes ; Waxes
Language	English
Publishing date	2003-05-01
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	208884-8
ISSN	1873-3700 ; 0031-9422
ISSN (online)	1873-3700
ISSN	0031-9422
DOI	10.1016/s0031-9422(03)00283-8
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Article: Anaerobic 1-Alkene Metabolism by the Alkane- and Alkene-Degrading Sulfate Reducer Desulfatibacillum aliphaticivorans Strain CV2803T

Grossi, Vincent / Cravo-Laureau, Cristiana / Méou, Alain / Raphel, Danielle / Garzino, Frédéric / Hirschler-Réa, Agnès

Applied and environmental microbiology AEM. 2007 Dec. 15, v. 73, no. 24

2007

Abstract: The alkane- and alkene-degrading, marine sulfate-reducing bacterium Desulfatibacillum aliphaticivorans strain CV2803T, known to oxidize n-alkanes anaerobically by fumarate addition at C-2, was investigated for its 1-alkene metabolism. The total cellular ... ...

Abstract	The alkane- and alkene-degrading, marine sulfate-reducing bacterium Desulfatibacillum aliphaticivorans strain CV2803T, known to oxidize n-alkanes anaerobically by fumarate addition at C-2, was investigated for its 1-alkene metabolism. The total cellular fatty acids of this strain were predominantly C-(even number) (C-even) when it was grown on C-even 1-alkenes and predominantly C-(odd number) (C-odd) when it was grown on C-odd 1-alkenes. Detailed analyses of those fatty acids by gas chromatography-mass spectrometry after 6- to 10-week incubations allowed the identification of saturated 2- and 4-ethyl-, 2- and 4-methyl-, and monounsaturated 4-methyl-branched fatty acids with chain lengths that correlated with those of the 1-alkene. The growth of D. aliphaticivorans on (per)deuterated 1-alkenes provided direct evidence of the anaerobic transformation of these alkenes into the corresponding 1-alcohols and into linear as well as 10- and 4-methyl-branched fatty acids. Experiments performed with [¹³C]bicarbonate indicated that the initial activation of 1-alkene by the addition of inorganic carbon does not occur. These results demonstrate that D. aliphaticivorans metabolizes 1-alkene by the oxidation of the double bond at C-1 and by the subterminal addition of organic carbon at both ends of the molecule [C-2 and C-(ω-1)]. The detection of ethyl-branched fatty acids from unlabeled 1-alkenes further suggests that carbon addition also occurs at C-3. Alkylsuccinates were not observed as potential initial intermediates in alkene metabolism. Based on our observations, the first pathways for anaerobic 1-alkene metabolism in an anaerobic bacterium are proposed. Those pathways indicate that diverse initial reactions of 1-alkene activation can occur simultaneously in the same strain of sulfate-reducing bacterium.
Keywords	alkenes ; anaerobiosis ; bicarbonates ; carbon ; fatty acid composition ; gas chromatography ; mass spectrometry ; monounsaturated fatty acids ; oxidation ; sulfate-reducing bacteria ; sulfates
Language	English
Dates of publication	2007-1215
Size	p. 7882-7890.
Publishing place	American Society for Microbiology
Document type	Article
ZDB-ID	223011-2
ISSN	1098-5336 ; 0099-2240
ISSN (online)	1098-5336
ISSN	0099-2240
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Article ; Online: Anaerobic 1-alkene metabolism by the alkane- and alkene-degrading sulfate reducer Desulfatibacillum aliphaticivorans strain CV2803T.

Grossi, Vincent / Cravo-Laureau, Cristiana / Méou, Alain / Raphel, Danielle / Garzino, Frédéric / Hirschler-Réa, Agnès

Applied and environmental microbiology

2007 Volume 73, Issue 24, Page(s) 7882–7890

Abstract: The alkane- and alkene-degrading, marine sulfate-reducing bacterium Desulfatibacillum aliphaticivorans strain CV2803(T), known to oxidize n-alkanes anaerobically by fumarate addition at C-2, was investigated for its 1-alkene metabolism. The total ... ...

Abstract	The alkane- and alkene-degrading, marine sulfate-reducing bacterium Desulfatibacillum aliphaticivorans strain CV2803(T), known to oxidize n-alkanes anaerobically by fumarate addition at C-2, was investigated for its 1-alkene metabolism. The total cellular fatty acids of this strain were predominantly C-(even number) (C-even) when it was grown on C-even 1-alkenes and predominantly C-(odd number) (C-odd) when it was grown on C-odd 1-alkenes. Detailed analyses of those fatty acids by gas chromatography-mass spectrometry after 6- to 10-week incubations allowed the identification of saturated 2- and 4-ethyl-, 2- and 4-methyl-, and monounsaturated 4-methyl-branched fatty acids with chain lengths that correlated with those of the 1-alkene. The growth of D. aliphaticivorans on (per)deuterated 1-alkenes provided direct evidence of the anaerobic transformation of these alkenes into the corresponding 1-alcohols and into linear as well as 10- and 4-methyl-branched fatty acids. Experiments performed with [(13)C]bicarbonate indicated that the initial activation of 1-alkene by the addition of inorganic carbon does not occur. These results demonstrate that D. aliphaticivorans metabolizes 1-alkene by the oxidation of the double bond at C-1 and by the subterminal addition of organic carbon at both ends of the molecule [C-2 and C-(omega-1)]. The detection of ethyl-branched fatty acids from unlabeled 1-alkenes further suggests that carbon addition also occurs at C-3. Alkylsuccinates were not observed as potential initial intermediates in alkene metabolism. Based on our observations, the first pathways for anaerobic 1-alkene metabolism in an anaerobic bacterium are proposed. Those pathways indicate that diverse initial reactions of 1-alkene activation can occur simultaneously in the same strain of sulfate-reducing bacterium.
MeSH term(s)	Alcohols/metabolism ; Alkanes/metabolism ; Anaerobiosis ; Bicarbonates/metabolism ; Carbon Radioisotopes/metabolism ; Deltaproteobacteria/growth & development ; Deltaproteobacteria/metabolism ; Fatty Acids/analysis ; Fatty Acids/chemistry ; Gas Chromatography-Mass Spectrometry ; Oxidation-Reduction ; Sulfates/metabolism
Chemical Substances	Alcohols ; Alkanes ; Bicarbonates ; Carbon Radioisotopes ; Fatty Acids ; Sulfates
Language	English
Publishing date	2007-10-26
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	223011-2
ISSN	1098-5336 ; 0099-2240
ISSN (online)	1098-5336
ISSN	0099-2240
DOI	10.1128/AEM.01097-07
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Article: Anaerobic n-Alkane Metabolism by a Sulfate-Reducing Bacterium, Desulfatibacillum aliphaticivorans Strain CV2803[superscript T]

Cravo-Laureau, Cristiana / Grossi, Vincent / Raphel, Danielle / Matheron, Robert / Hirschler-Réa, Agnès

Applied and environmental microbiology. 2005 July, v. 71, no. 7

2005

Abstract: The alkane-degrading, sulfate-reducing bacterium Desulfatibacillum aliphaticivorans strain CV2803[superscript T], recently isolated from marine sediments, was investigated for n-alkane metabolism. The total cellular fatty acids of this strain had ... ...

Abstract	The alkane-degrading, sulfate-reducing bacterium Desulfatibacillum aliphaticivorans strain CV2803[superscript T], recently isolated from marine sediments, was investigated for n-alkane metabolism. The total cellular fatty acids of this strain had predominantly odd numbers of carbon atoms (C odd) when the strain was grown on a C-odd alkane (pentadecane) and even numbers of carbon atoms (C even) when it was grown on a C-even alkane (hexadecane). Detailed analyses of those fatty acids by gas chromatography/mass spectrometry allowed us to identify saturated 2-, 4-, 6-, and 8-methyl- and monounsaturated 6-methyl-branched fatty acids, with chain lengths that specifically correlated with those of the alkane. Growth of D. aliphaticivorans on perdeuterated hexadecane demonstrated that those methyl-branched fatty acids were directly derived from the substrate. In addition, cultures on pentadecane and hexadecane produced (1-methyltetradecyl)succinate and (1-methylpentadecyl)succinate, respectively. These results indicate that D. aliphaticivorans strain CV2803[superscript T] oxidizes n-alkanes into fatty acids anaerobically, via the addition of fumarate at C-2. Based on our observations and on literature data, a pathway for anaerobic n-alkane metabolism by D. aliphaticivorans is proposed. This involves the transformation of the initial alkylsuccinate into a 4-methyl-branched fatty acid which, in addition to catabolic reactions, can alternatively undergo chain elongation and desaturation to form storage fatty acids.
Keywords	anaerobiosis ; branched chain fatty acids ; fatty acid composition ; fumaric acid ; gas chromatography ; hexadecane ; marine sediments ; mass spectrometry ; monounsaturated fatty acids ; sulfate-reducing bacteria
Language	English
Dates of publication	2005-07
Size	p. 3458-3467.
Publishing place	American Society for Microbiology
Document type	Article
Note	Includes references
ZDB-ID	223011-2
ISSN	1098-5336 ; 0099-2240
ISSN (online)	1098-5336
ISSN	0099-2240
DOI	10.1128/AEM.71.7.3458-3467.2005
Database	NAL-Catalogue (AGRICOLA)

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Article: Anaerobic n-alkane metabolism by a sulfate-reducing bacterium, Desulfatibacillum aliphaticivorans strain CV2803T.

Cravo-Laureau, Cristiana / Grossi, Vincent / Raphel, Danielle / Matheron, Robert / Hirschler-Réa, Agnès

Applied and environmental microbiology

2005 Volume 71, Issue 7, Page(s) 3458–3467

Abstract: The alkane-degrading, sulfate-reducing bacterium Desulfatibacillum aliphaticivorans strain CV2803T, recently isolated from marine sediments, was investigated for n-alkane metabolism. The total cellular fatty acids of this strain had predominantly odd ... ...

Abstract	The alkane-degrading, sulfate-reducing bacterium Desulfatibacillum aliphaticivorans strain CV2803T, recently isolated from marine sediments, was investigated for n-alkane metabolism. The total cellular fatty acids of this strain had predominantly odd numbers of carbon atoms (C odd) when the strain was grown on a C-odd alkane (pentadecane) and even numbers of carbon atoms (C even) when it was grown on a C-even alkane (hexadecane). Detailed analyses of those fatty acids by gas chromatography/mass spectrometry allowed us to identify saturated 2-, 4-, 6-, and 8-methyl- and monounsaturated 6-methyl-branched fatty acids, with chain lengths that specifically correlated with those of the alkane. Growth of D. aliphaticivorans on perdeuterated hexadecane demonstrated that those methyl-branched fatty acids were directly derived from the substrate. In addition, cultures on pentadecane and hexadecane produced (1-methyltetradecyl)succinate and (1-methylpentadecyl)succinate, respectively. These results indicate that D. aliphaticivorans strain CV2803T oxidizes n-alkanes into fatty acids anaerobically, via the addition of fumarate at C-2. Based on our observations and on literature data, a pathway for anaerobic n-alkane metabolism by D. aliphaticivorans is proposed. This involves the transformation of the initial alkylsuccinate into a 4-methyl-branched fatty acid which, in addition to catabolic reactions, can alternatively undergo chain elongation and desaturation to form storage fatty acids.
MeSH term(s)	Alkanes/metabolism ; Anaerobiosis ; Biodegradation, Environmental ; Culture Media ; Deltaproteobacteria/growth & development ; Deltaproteobacteria/isolation & purification ; Deltaproteobacteria/metabolism ; Fatty Acids/metabolism ; Geologic Sediments/microbiology ; Seawater/microbiology ; Sulfur-Reducing Bacteria/growth & development ; Sulfur-Reducing Bacteria/isolation & purification ; Sulfur-Reducing Bacteria/metabolism
Chemical Substances	Alkanes ; Culture Media ; Fatty Acids ; n-hexadecane (F8Z00SHP6Q)
Language	English
Publishing date	2005-07
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	223011-2
ISSN	1098-5336 ; 0099-2240
ISSN (online)	1098-5336
ISSN	0099-2240
DOI	10.1128/AEM.71.7.3458-3467.2005
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Book ; Online: Phytol and phytyldiol concentrations at DYFAMED time series station and sediment trap, supplementary data to: Cuny, Philippe; Marty, Jean-Claude; Chiav?rini, Jacques; Vescovali, Isabelle; Raphel, Danielle; Rontani, Jean-Fran?ois (2002): One-year seasonal survey of the chlorophyll photodegradation process in the northwestern Mediterranean Sea. Deep Sea Research Part II: Topical Studies in Oceanography, 49(11), 1987-2005

Cuny, Philippe / Chiav?rini, Jacques / Marty, Jean-Claude / Raphel, Danielle / Rontani, Jean-Fran?ois / Vescovali, Isabelle

2002

Abstract: Particulate samples from the water column were collected monthly from depths of 5-150 m, between May 1996 and March 1997, in the northwestern Mediterranean Sea (Ligurian Sea) as part of the DYFAMED project within the French JGOFS program. These samples ... ...

Abstract	Particulate samples from the water column were collected monthly from depths of 5-150 m, between May 1996 and March 1997, in the northwestern Mediterranean Sea (Ligurian Sea) as part of the DYFAMED project within the French JGOFS program. These samples were analyzed by gas chromatography-electron impact mass spectrometry for their phytol and 3-methylidene-3,7,11-trimethylhexadecan-1,2-diol (phytyldiol) content. The corresponding Chlorophyll Phytyl side chain Photodegradation Index, molar ratio of phytyldiol to phytol, was calculated and the mean amount of chlorophyll photodegraded within the euphotic zone estimated. Seasonal differences in the chlorophyll photodegradation process appear in the one-year study. The chlorophyll appeared more photodegraded in the surface water (generally more than 40% photodegraded at 5-10 m) than at the deep chlorophyll maximum (DCM) (40-50 m) observed in the summer stratified waters (about 20% photodegraded). This difference was attributed to the healthy state of the phytoplankton community (coincidence with the highest primary production levels) and to the lower intensity of irradiance at the DCM level. On the other hand, the bulk of the detrital chlorophyll (chlorophyll associated with phytodetritus, phaeopigments) undergoes photodegradation before it sinks out of the photic zone. However, in January (winter mixed water) the pigments exported towards the sea floor were less photodegraded. This is thought to result from a shorter period of residence of the pigments in the photic zone due to vertical convection and grazing activity of macrozooplankton (salps), which are producers of rapid sinking fecal pellets.
Language	English
Dates of publication	2002-9999
Size	Online-Ressource
Publisher	PANGAEA - Data Publisher for Earth & Environmental Science
Publishing place	Bremen/Bremerhaven
Document type	Book ; Online
Note	This dataset is supplement to doi:10.1016/S0967-0645(02)00023-1
DOI	10.1594/PANGAEA.738645
Database	Library catalogue of the German National Library of Science and Technology (TIB), Hannover

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Article: C(25) highly branched isoprenoid alkenes from the marine benthic diatom Pleurosigma strigosum.

Grossi, Vincent / Beker, Béatriz / Geenevasen, Jan A J / Schouten, Stefan / Raphel, Danielle / Fontaine, Marie-France / Sinninghe Damsté, Jaap S

Phytochemistry

2004 Volume 65, Issue 22, Page(s) 3049–3055

Abstract: The hydrocarbon composition of the marine diatom Pleurosigma strigosum isolated from coastal Mediterranean sediments is described. A suite of five C(25) highly branched isoprenoid (HBI) alkenes with 2-5 double bonds were detected together with n-C(21:4) ... ...

Abstract	The hydrocarbon composition of the marine diatom Pleurosigma strigosum isolated from coastal Mediterranean sediments is described. A suite of five C(25) highly branched isoprenoid (HBI) alkenes with 2-5 double bonds were detected together with n-C(21:4) and n-C(21:5) alkenes and squalene. The analysis by (1)H and (13)C NMR spectroscopy of two isolated HBI alkenes allowed the structural identification of a novel C(25) HBI triene (2,6,10,14-tetramethyl-7-(3-methylpent-4-enyl)-pentadeca-5E,13-diene) and the first identification in diatom cells of 2,6,10,14-tetramethyl-7-(3-methylpent-4-enyl)-pentadec-5E-ene, an HBI previously detected in marine sediments and particulate matter. The other minor C(25) HBIs detected were a tetraene and a pentaene that have been previously identified in other diatoms from the genera Haslea and Rhizosolenia, and one other C(25) tetraene that could not be structurally identified. The structures of the HBI alkenes of P. strigosum were compared with those of C(25) homologues previously identified in three other Pleurosigma sp. (Pleurosigma intermedium, Pleurosigma planktonicum and Pleurosigma sp.). Unlike most structures previously reported, none of the HBI alkenes produced by P. strigosum showed an unsaturation at C7-C20, or E/Z isomerism of the trisubstituted double bond at C9-C10 (whenever present).
MeSH term(s)	Diatoms/chemistry ; Environment ; Gas Chromatography-Mass Spectrometry ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Terpenes/analysis
Chemical Substances	Terpenes
Language	English
Publishing date	2004-11
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	208884-8
ISSN	1873-3700 ; 0031-9422
ISSN (online)	1873-3700
ISSN	0031-9422
DOI	10.1016/j.phytochem.2004.09.002
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