Occurrence of all-cis-5,8,11,14,17,20,23-hexacosaheptaenoic acid (26:7n-3) in roughscale sole Clidoderma asperrimum flesh lipids

Fukuda, Yuuki; Ando, Yasuhiro

doi:10.1007/s12562-011-0387-y

Fish Sci

2011

DOI: 10.1007/s12562-011-0387-y

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Occurrence of all-cis-5,8,11,14,17,20,23-hexacosaheptaenoic acid (26:7n-3) in roughscale sole Clidoderma asperrimum flesh lipids

Yuuki Fukuda

Yasuhiro Ando

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Cited by 5 publications

(1 citation statement)

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“…Marine algae are rich in the highly unsaturated fatty acids, DHA and EPA. In addition, fatty acids with both greater degrees of unsaturation and longer chain lengths have also been identified in marine algae. − These very-long-chain PUFAs from marine algae can be traced through the food chain and have been identified in marine animals such as fish, ,− invertebrates, − and seals…”

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Rapid Identification of Long-Chain Polyunsaturated Fatty Acids in a Marine Extract by HPLC-MS Using Data-Dependent Acquisition

Thomas

Dunn

Altvater³

et al. 2012

Anal. Chem.

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The collision-induced dissociation (CID) of a range of deprotonated fatty acid standards was studied using linear ion trap mass spectrometry. Neutral losses of 78, 98, and 136 Da were consistently observed for fatty acids with five or more double bonds. Comparison of the MS/MS spectra of docosahexaenoic acid (DHA) and universally (13)C-labeled DHA allowed the molecular formulas for these neutral losses to be determined as C(6)H(6), C(5)H(6)O(2), and C(8)H(8)O(2). Knowledge of fatty acid fragmentation processes was then applied to identify fatty acids from a sea anemone, Aiptasia pulchella, and dinoflagellate symbiont, Symbiodinium sp. extract. Using HPLC-MS, fatty acids were separated and analyzed by tandem mass spectrometry in data-dependent acquisition mode. Neutral loss chromatograms for 78, 98, and 136 Da allowed the identification of long-chain fatty acids with five or more double bonds. On the basis of precursor ion m/z ratios, chain length and degree of unsaturation for these fatty acids were determined. The application of this technique to an Aiptasia sp.-Symbiodinium sp. lipid extract enabled the identification of the unusual, long-chain fatty acids 24:6, 26:6, 26:7, 28:7, and 28:8 during a single 40 min HPLC-MS analysis.

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confidence: 99%

Rapid Identification of Long-Chain Polyunsaturated Fatty Acids in a Marine Extract by HPLC-MS Using Data-Dependent Acquisition

Thomas

Dunn

Altvater³

et al. 2012

Anal. Chem.

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Occurrence of Hexacosapolyenoic Acids 26:7(n‐3), 26:6(n‐3), 26:6(n‐6) and 26:5(n‐3) in Deep‐Sea Brittle Stars from Near the Kuril Islands

Svetashev

Kharlamenko

2015

Lipids

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Significant amounts of polyunsaturated fatty acids (PUFA) with a chain length of 26 carbon atoms were detected in lipids of five deep water species of Ophiuroidea besides common fatty acids with chain lengths between 14 and 24. By means of hydrogenation, GC-MS of the methyl esters, and 4,4-dimethyloxazoline (DMOX) derivatives of these C26 acids were characterized as 5,8,11,14,17,20,23-hexacosaheptaenoic [26:7(n-3)]; 8,11,14,17,20,23-hexacosahexaenoic [26:6(n-3)]; 5,8,11,14,17,20- hexacosahexaenoic [26:6(n-6)]; and 11,14,17,20,23-hexacosapentaenoic [26:5(n-3)]. Concentrations of these acids varied from 0.3 to 4.5 mol% of the total FA. In all the samples investigated, the main component of C26PUFA was hexacosaheptaenoic acid 26:7(n-3). These C26PUFA are localized mainly in polar lipids. The presence of the possible biosynthesis precursors suggests that the C26PUFA are produced by the brittle stars, and are not accumulated from food sources. This finding can also explain the presence of small amounts of the 26:7(n-3) acid detected earlier in flesh lipids of the roughscale sole Clidoderma asperrimum, which feeds on deep water brittle stars. We suggest a possible scheme of the biosynthesis of C26 PUFA.

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Synthesis of Urethane Derivatives of Mono‐ and Diacylglycerols for Use as HPLC Standards in the Enantiomeric Separation

Tada¹,

Fujita²,

Ando³

2014

J Americ Oil Chem Soc

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This paper presents a convenient method for the preparation of referential standards 25 for high-performance liquid chromatography (HPLC) used in stereospecific analysis of triacyl-26 sn-glycerols via monoacylglycerol or diacylglycerol intermediates. In the analysis, these partial 27 acylglycerols are separated into their respective positional and enantiomeric isomer classes by 28 chiral HPLC as their 3,5-dinitrophenylurethane derivatives or by silicic acid HPLC as their (S)-29 or (R)-1-(1-naphthyl)ethyl urethane derivatives. In this study, these urethane derivative 30 standards were synthesized by the following novel procedure: first, partial urethane derivatives 31 of glycerol were prepared by carbamoylation of glycerol with isocyanates; secondly, the 32 products were separated into positional isomer classes by silicic acid HPLC, and; finally, a fatty 33 acid was added to the partial urethanes using N,N'-dicyclohexylcarbodiimide. The identities of 34 the resulting urethane derivatives of glycerol were verified by mass spectrometry and HPLC. 35

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Occurrence of all-cis-5,8,11,14,17,20,23-hexacosaheptaenoic acid (26:7n-3) in roughscale sole Clidoderma asperrimum flesh lipids

Cited by 5 publications

References 52 publications

Rapid Identification of Long-Chain Polyunsaturated Fatty Acids in a Marine Extract by HPLC-MS Using Data-Dependent Acquisition

Rapid Identification of Long-Chain Polyunsaturated Fatty Acids in a Marine Extract by HPLC-MS Using Data-Dependent Acquisition

Occurrence of Hexacosapolyenoic Acids 26:7(n‐3), 26:6(n‐3), 26:6(n‐6) and 26:5(n‐3) in Deep‐Sea Brittle Stars from Near the Kuril Islands

Synthesis of Urethane Derivatives of Mono‐ and Diacylglycerols for Use as HPLC Standards in the Enantiomeric Separation

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