Novel Di‐, Tri‐, and tetraenoic fatty acids with <i>bis</i>‐methylene‐interrupted double‐bond systems from the sponge <i>Haliclona cinerea</i>

Joh, Yong-Goe; Elenkov, Ivaylo; Stefanov, Kamen; Попов, Симеон; Dobson, Gary; Christie, William W.

doi:10.1007/s11745-997-0003-6

Cited by 22 publications

(23 citation statements)

References 15 publications

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“…However, an even more characteristic feature for a bis-methylene-interrupted diene is an ion at m/z = 219 (actually 218 + 1, which unusually is odd-numbered). This has been found in a number of fatty acids with 5,9-double bonds (22)(23)(24)(25)(26), including those in sponges, and analogous ions are found with other bis-methylene interrupted dienes (27).…”

Section: Mass Spectrometry Of Picolinyl Ester and Dimethyloxazoline Dmentioning

confidence: 72%

Gas chromatography‐mass spectrometry methods for structural analysis of fatty acids

Christie

1998

Lipids

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329

246

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Procedures for structural analysis of fatty acids are reviewed. The emphasis is on methods that involve gas chromatography-mass spectrometry and, in particular, the use of picolinyl ester and dimethyloxazoline derivatives. These should be considered as complementing each other, not simply as alternatives. However, additional derivatization procedures can be of value, including hydrogenation and deuteration, and preparation of dimethyl disulfide and 4-methyl-1,2,4-triazoline-3,5-dione adducts. Sometimes complex mixtures must be separated into simpler fractions prior to analysis by gas chromatography-mass spectrometry. Silver ion and reversed-phase high-performance liquid chromatography are then of special value. In particular, a novel application of the latter technique, involving a base-deactivated stationary phase and acetonitrile as mobile phase, is described that is suited to the separation of fatty acids in the form of picolinyl ester and dimethyloxazoline derivatives, as well as methyl esters.

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Section: Mass Spectrometry Of Picolinyl Ester and Dimethyloxazoline Dmentioning

confidence: 72%

Gas chromatography‐mass spectrometry methods for structural analysis of fatty acids

Christie

1998

Lipids

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329

246

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“…No peaks could be detected between 16:0 and 17:0 acid methyl esters, in conditions where a component representing less than 0.005% should have been detected. Alternatively, the saturated acids were isolated by high-performance liquid chromatography in the silver-ion mode and analyzed as picolinyl esters by GLC-mass spectrometry in conditions described elsewhere (18). Here too, 14-MHD was not detectable.…”

Section: Resultsmentioning

confidence: 99%

The seed fatty acid composition and the distribution of Δ5‐olefinic acids in the triacylglycerols of some taxaceae (Taxus and Torreya)

Wolff

Pédrono

Marpeau³

et al. 1998

J Americ Oil Chem Soc

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The fatty acid compositions of the seeds from three Taxus (yew) species and one Torreya species belonging to the Taxaceae family [Taxus cuspidata (Japanese yew), T. chinensis (Chinese yew), T. baccata (English yew), and Torreya grandis (Chinese nutmeg yew)] have been established. These compositions were compared with those previously published for T. canadensis (Canadian yew) and Torreya nucifera. In Taxus species, as well as in Torreya species, ∆5-olefinic acids are present in the seed lipids from all species analyzed. In Taxus, 5,9-18:2 (taxoleic) acid is the prominent ∆5-olefinic acid. It represents between 9.5 and 16.2% of total fatty acids. Other ∆5-olefinic acids that occur in low amounts are 5,9,12-18:3 (<3.5%), 5,11-20:2 (<0.3%), 5,11,14-20:3 (<2.2%), and 5,11,14,17-20:4 (<0.3%) acids. In Torreya species, the major ∆5-olefinic acid is 5,11,14-20:3 (sciadonic) acid (between 6.7 and 11.2%). In contrast to Taxus species, the 5,9-18:2 and 5,9,12-18:3 acids are scarce in Torreya species: less than 0.1%. Also, the 9,12,15-18:3 acid content is significantly lower in Torreya than in Taxus. The prominence of taxoleic acid among ∆5-olefinic acids in the seed lipids is a unique characteristic of the genus Taxus that isolates it from all other Coniferophytes analyzed so far. However, this feature is not shared by other Taxaceae species, such as Torreya, and with regard to their seed fatty acid compositions, the family Taxaceae appears particularly heterogeneous. Our observations favor the hypothesis that in Gymnosperm seeds, there might exist two ∆5-desaturases, one specific for unsaturated acids with a ∆9-ethylenic bond (active in Taxus but not in Torreya), and the other specific for unsaturated acids with a ∆11-ethylenic bond (active in Torreya but not in Taxus). Our data also highlight the importance of the elongase(s) in the metabolism of fatty acids in Gymnosperm seeds. 14-Methylhexadecanoic acid, a habitual component of Pinaceae and Ginkgo biloba seed lipids, could not be detected in the Taxaceae studied here. 13 C nuclear magnetic resonance spectroscopy of the oils from both genera has confirmed that ∆5-olefinic acids are apparently excluded from the internal position of triacylglycerols, which is a characteristic common to all Gymnosperm species analyzed so far, and consequently of great antiquity in their life history.

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“…Although the ions produced by cleavage at the double bond per se are not easily distinguished, the overall spectrum is so distinctive that this hardly matters. When fatty acids containing 5,9-double bond systems are chain-elongated to form 7,11-dienes, for example, the ion representing cleavage at the centre of the bis-allylic system is increased by 28 amu to 208 [62,85].…”

Section: Ms Characterisation Of ∆ ∆5-upifa Derivativesmentioning

confidence: 99%

Structures, practical sources (gymnosperm seeds), gas-liquid chromatographic data (equivalent chain lengths), and mass spectrometric characteristics of all-cis Δ5-olefinic acids

Wolff

Christie

2002

Eur. J. Lipid Sci. Technol.

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Structures, practical sources (gymnosperm seeds), gas-liquid chromatographic data (equivalent chain lengths), and mass spectrometric characteristics of all-cis ∆ ∆5-olefinic acidsIn view of the increasing interest of lipid researchers in the biological effects of all-cis ∆5-unsaturated polymethylene-interrupted fatty acids (∆5-UPIFA) from vegetable origin, this paper is concerned with their occurrence in practical sources (gymnosperm seeds), structures, and identification by gas-liquid chromatography (GLC) and mass spectrometry (MS). The use of equivalent chain lengths (ECL) determined by calculations based on available standards, in close agreement with data determined with easily available commercial gymnosperm seeds specific for each ∆5-UPIFA, allows identification of all ∆5-UPIFA. These tentative identifications are supported by GLC-MS of the appropriate (4,4-dimethyloxazoline and picolinyl ester) derivatives. ECL are particularly useful to identify ∆5-UPIFA in tissue lipids from animals experimentally fed oils containing these acids, with no interference with polyunsaturated fatty acids of endogenous origin.

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Novel Di‐, Tri‐, and tetraenoic fatty acids with bis‐methylene‐interrupted double‐bond systems from the sponge Haliclona cinerea

Cited by 22 publications

References 15 publications

Gas chromatography‐mass spectrometry methods for structural analysis of fatty acids

Gas chromatography‐mass spectrometry methods for structural analysis of fatty acids

The seed fatty acid composition and the distribution of Δ5‐olefinic acids in the triacylglycerols of some taxaceae (Taxus and Torreya)

Structures, practical sources (gymnosperm seeds), gas-liquid chromatographic data (equivalent chain lengths), and mass spectrometric characteristics of all-cis Δ5-olefinic acids

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