Identification of a novel alkenone in Black Sea sediments

Xu, Li; Reddy, Christopher M.; Farrington, John W.; Frysinger, Glenn S.; Gaines, Richard B.; Johnson, C. G.; Nelson, Robert K.; Eglinton, T. I.

doi:10.1016/s0146-6380(01)00019-5

Cited by 91 publications

(85 citation statements)

References 41 publications

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“…Among all these compounds, only three have been synthesized [16] and only one has been isolated in sufficient amounts to perform NMR studies [17] or GC-IR. Three of the C 37 alkenones identified in the present study show the same structure as those obtained by total synthesis [16].…”

Section: Previously Known Long Chain Alkenonesmentioning

confidence: 99%

“…Recent studies on sediments of the Black Sea (5000 -8000 y BP) involving the combined use of GC coupled to infrared spectroscopy (GC-IR), nuclear magnetic resonance (NMR), direct insertion electron impact mass spectrometry (Probe-EIMS), and dimethyldisulphide (DMDS) derivatization allowed double bond location of (16E,21E)-hexatriacontadien-3-one [17]. This compound was the major constituent of an homologous series of long chain diunsaturated ketones (C 35 -C 39 ), analogous to another series with chain lengths from C 37 to C 42 found in ancient sediments off the North Atlantic west coast (95 and 105 Ma, Cretaceous) [18].…”

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confidence: 99%

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Phenyl- and cyclopentylimino derivatization for double bond location in unsaturated C₃₇-C₄₀ alkenones by GC-MS

López

Grimalt

2004

J. Am. Soc. Mass Spectrom.

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A method for the identification of double bond locations in polyunsaturated long chain alkenones adapted to nanogram amounts as currently analyzed by gas chromatography coupled to mass spectrometry (GC-MS) has been developed. The method is based on interpretation of the electron impact mass spectra of the imino derivatives of the carbonyl groups using either cyclopentyl or phenyl substitutents. Other complementary derivatization methods such as elaidization and hydrogenation have also been used for structural characterization of these compounds. This application has led to the identification of a novel homologous series of di-, tri-, and tetraunsaturated ketones with carbon number chain lengths between 37 and 40 in coastal hypersaline sediments. The novel series identified shows a distribution in which the double bond position between different homologs is established by reference to the distance from the carbonyl group whereas the previously known alkenones were constituted by unsaturated homologs with double bonds located at defined distances of the terminal methyl. This difference points out to a dissimilar, but still unknown, biogenic precursor of these novel alkenones. (J Am Soc Mass Spectrom 2004, 15, 1161-1172

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Section: Previously Known Long Chain Alkenonesmentioning

confidence: 99%

mentioning

confidence: 99%

Phenyl- and cyclopentylimino derivatization for double bond location in unsaturated C₃₇-C₄₀ alkenones by GC-MS

López

Grimalt

2004

J. Am. Soc. Mass Spectrom.

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“…Thus, all compounds are subjected to two different separation mechanisms. GC6GC has been used to separate and quantify aromatic and oxygenated compounds in geological [67], environmental [66,68], and forensic samples [69]. When a GC6GC is coupled to a mass spectrometer (GC6GC -MS) an additional dimension of information about the sample is provided.…”

Section: Other Methodsmentioning

confidence: 99%

Gas chromatography coupled to mass spectrometry for analyses of organic compounds and biomarkers as tracers for geological, environmental, and forensic research

Medeiros

Simoneit

2007

J of Separation Science

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ReviewGas chromatography coupled to mass spectrometry for analyses of organic compounds and biomarkers as tracers for geological, environmental, and forensic research Gas chromatography, especially when coupled with mass spectrometry, is the analytical method of choice for elucidation of biomarker compounds present in organic mixtures extracted from geological, environmental, and biological samples. This review describes the biomarker concept, i. e., the precursor natural products to the geological/environmental derivatives, and their application as multi-tracers in the geosphere and ambient environment. The mass spectrometric methods currently utilized for such analyses are reviewed with a general key to the literature, and typical examples of applications using GC -MS are also described.

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“…An unusual C 36 diunsaturated alkenone was identified by Xu et al (2001) in Holocene sediments from the Black Sea. This compound, which was shown from nuclear magnetic resonance (NMR) spectroscopy to be an ethyl ketone with double bonds at ω15,20 (from now on C 36:2 EK), was the most abundant alkenone in Unit II of the Black Sea sediments (7.3-3.6 kyr BP).…”

Section: Introductionmentioning

confidence: 98%

“…Fujine et al (2006) suggested a relationship with low salinity conditions, although a true freshwater origin is unlikely according to Xu et al (2001) since the C 36:2 EK in the Black Sea occurred only after the introduction of marine water. Association with low salinity conditions is also inconsistent with its present-day occurrence in the Ligurian Sea (Rontani et al, 2001).…”

Section: Introductionmentioning

confidence: 99%

Unusual C35 to C38 alkenones in mid-Holocene sediments from a restricted estuary (Charlotte Harbor, Florida)

Soelen

Lammers

Eglinton

et al. 2014

Organic Geochemistry

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Unusual C 35 to C 38 alkenones were identified in mid-Holocene (8-3.5 kyr BP) sediments from a restricted estuary in southwest Florida (Charlotte Harbor). The distribution was dominated by a C 36 diunsaturated (ω15,20) ethyl ketone, identical to the one present in Black Sea Unit 2 sediments. Other unusual alkenones were tentatively assigned as a C 35:2 (ω 15,20) methyl ketone, a C 37:2 (ω 17,22) methyl ketone and a C 38:2 (ω 17,22) ethyl ketone. In late Holocene sediments < 3.5 kyr BP, the common C 37 to C 39 alkenones were found. Compound-specific 14 C, 13 C, and D isotope measurements were used to constrain the possible origin of the alkenones. Conventional radiocarbon ages of alkenones and higher plant-derived long chain n-alcohols indicated no significant difference in age between mid-Holocene alkenones and higher plant n-alcohols. Both alcohols and alkenones were offset vs. calibrated ages of shell fragments in the same sediment core, which suggests they were pre-aged by 500-800 yr, implying resuspension and redistribution of the fine-grained sedimentary particles with which they are associated. The hydrogen isotopic (δD) composition (-190‰ to -200‰) of the C 37 and C 38 alkenones in the late Holocene sediments is in line with values for coastal haptophytes in brackish water. However, the unusual C 36 and C 38 alkenones from the mid Holocene sediments were enriched in D (by ca. 100‰) vs. the late Holocene alkenones. Also, δ 13 C values of mid-Holocene alkenones were consistently offset compared with late Holocene alkenones (-21‰ to -22‰ and -22‰ to -23‰, respectively). We suggest that the alkenones in Charlotte Harbor were produced by unknown alkenone-producing haptophyte.

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Identification of a novel alkenone in Black Sea sediments

Cited by 91 publications

References 41 publications

Phenyl- and cyclopentylimino derivatization for double bond location in unsaturated C₃₇-C₄₀ alkenones by GC-MS

Phenyl- and cyclopentylimino derivatization for double bond location in unsaturated C₃₇-C₄₀ alkenones by GC-MS

Gas chromatography coupled to mass spectrometry for analyses of organic compounds and biomarkers as tracers for geological, environmental, and forensic research

Unusual C35 to C38 alkenones in mid-Holocene sediments from a restricted estuary (Charlotte Harbor, Florida)

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Identification of a novel alkenone in Black Sea sediments

Cited by 91 publications

References 41 publications

Phenyl- and cyclopentylimino derivatization for double bond location in unsaturated C37-C40 alkenones by GC-MS

Phenyl- and cyclopentylimino derivatization for double bond location in unsaturated C37-C40 alkenones by GC-MS

Gas chromatography coupled to mass spectrometry for analyses of organic compounds and biomarkers as tracers for geological, environmental, and forensic research

Unusual C35 to C38 alkenones in mid-Holocene sediments from a restricted estuary (Charlotte Harbor, Florida)

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Phenyl- and cyclopentylimino derivatization for double bond location in unsaturated C₃₇-C₄₀ alkenones by GC-MS

Phenyl- and cyclopentylimino derivatization for double bond location in unsaturated C₃₇-C₄₀ alkenones by GC-MS