Tetracosapolyenoic Acids Research Articles

A comparison of food sources of nudibranch mollusks at different depths off the Kuril Islands using fatty acid trophic markers.

Gastropod molluscs such as nudibranchs are important members of deep-sea benthic ecosystems. However, data on the trophic ecology and feeding specialization of these animals are limited to date. The method of fatty acid trophic markers (FATM) was applied to determine the dietary preferences of nudibranchs off the Kuril Islands. Fatty acid (FA) compositions of Dendronotus sp., Tritonia tetraquetra, and Colga pacifica collected from deep waters were analyzed and compared with those of Aeolidia papillosa and Coryphella verrucosa from the offshore zone. The high level of FATM such as 22:5n-6 and C20 monounsaturated FAs indicated that Dendronotus sp. preys on sea anemones and/or anthoathecates hydroids similarly to that of shallow-water species A. papillosa and C. verrucosa. The high percentage of tetracosapolyenoic acids and the ratio 24:6n-3/24:5n-6 indicated that T. tetraquetra preys on soft corals such as Gersemia and/or Acanella at a depth of 250 m, but soft corals of the family Primnoidae may be the main item in the diet of T. tetraquetra at a depth of 500 m. The high content of Δ 7,13-22:2 and 22:6n-3 shows that C. pacifica can feed on bryozoans. In C. pacifica, 22:5n-6 may be synthesized intrinsically by the mollusks, whereas odd-chain and branched saturated FAs originate from associated bacteria.

Tracing of lipid markers of soft corals in a polar lipidome of the nudibranch mollusk Tritonia tetraquetra from the Sea of Okhotsk

To trace predator‒prey interactions in the marine environment, fatty acids (FAs) were widely applied as qualitative markers. Recently, two tetracosapolyenoic acids (TPA), which are specific markers of soft corals, have been found in the nudibranch mollusk Tritonia tetraquetra collected in the deep waters of the Sea of Okhotsk. This mollusk does not synthesize TPA but preys mostly on the soft coral Gersemia fruticosa. Both invertebrates are common species in Arctic and boreal regions and may be a simple model for the investigation of FA marker transfer from one trophic level to another. A lipidomic approach was applied to study the transfer of the FA markers in this predator–prey system. The structure and content of the molecular species of polar lipids (polar lipidome) of both animal species were analyzed by high-performance liquid chromatography with high-resolution tandem mass spectrometry. The distribution of several principal FA markers in lipid molecular species was determined. C20 monoenoic FAs of the coral were not integrated in the most of nudibranch lipids. Arachidonic and eicosapentaenoic acids mainly esterified ethanolamine and choline glycerophospholipids (PE and PC) in both invertebrates. In the coral polar lipidome, TPA concentrated in serine glycerophospholipids (PS). The nudibranch decomposed coral lipids and reallocated TPA to PS, PE, and PC. We suppose that this reallocation is responsible for the accumulation of TPA in the nudibranch. The nudibranch differed from the coral in biosynthetic relationships of phospholipid classes. The lipidomic approach explains the rearrangement of dietary FAs in the predator lipids. This rearrangement can be important for the trophic uptake and transfer of lipids in polar marine ecosystems.

High level of tetracosapolyenoic fatty acids in the cold-water mollusk Tochuina tetraquetra is a result of the nudibranch feeding on soft corals

Fatty acid (FA) markers are used to trace predator–prey relationships in the marine environment. Soft corals contain tetracosapolyenoic acids (TPA), namely 24:5n-6 and 24:6n-3, which are considered as octocoral FA markers. The nudibranch mollusks are known to feed on soft corals. To check whether TPA are transferred from soft corals to nudibranch mollusks during their nutrition, we determined and compared FA compositions of total lipids of Tochuina tetraquetra and soft corals (Acanella sp., Anthomastus rylovi, Gersemia fruticosa, and Paragorgia arborea) collected together near the Kuril Islands (the depths of 80–550 m). FA compositions of T. tetraquetra, Acanella sp. and A. rylovi were described for the first time. In Acanella sp., G. fruticosa, A. rylovi, and P. arborea, the average contents of TPA were 6.5, 13.4, 5.9, and 12.0 % of total FAs, whereas the 24:5n-6/24:6n-3 ratio was 1.0, 1.4, 5.4, and 2.6, respectively. The high level of TPA (21.7 %) found in T. tetraquetra indicates that 24:5n-6 and 24:6n-3 are transferred from soft corals to the mollusks during their feeding and accumulated in mollusk tissues. The most possible feed source of the mollusk is suggested to be G. fruticosa and/or Acanella sp., because the 24:5n-6/24:6n-3 ratios in T. tetraquetra and these soft corals were similar. Thus, the TPA could be used as FA markers to estimate a proportion of soft corals in feeding of cold-water nudibranch mollusks.

Distribution of Very-Long-Chain Fatty Acids between Molecular Species of Different Phospholipid Classes of Two Soft Corals

Fatty acids (FAs) of soft corals contain two very-long-chain tetracosapolyenoic acids (TPA, 24:5n-6 and 24:6n-3), which are chemotaxonomic markers of all species of the subclass Octocorallia. The distribution of TPA in molecular species of different phospholipid (PL) classes was investigated for the first time in the soft corals Sinularia macropodia and Capnella sp. From shallow waters of Vietnam. Phosphatidylethanolamine (PE), phosphatidylcholine (PC), phosphatidylserine (PS), and phosphatidylinositol (PI) were the major PL classes of S. macropodia and Capnella sp. More than thirty two molecular species of these four PL classes were determined by high resolution tandem mass spectrometry. 18:1e/20:4 PE, 18:0e/20:4 PC, 18:0e/24:5 PS, and 18:0/24:5 PI were the major molecular species of PL in both coral species. PE, PC, and PS mainly consisted of alkyl acyl and alkenyl acyl forms, but diacyl forms predominated in PI. TPA were the principal FAs in PS and PI, whereas 20:4n-6 was more abundant in PE and PC. Selective incorporation of TPA in the molecules of PS and PI are supposed to be a specific feature of the biosynthesis of PL in alcyonarians. To study the trophic and symbiotic relationships of soft corals, some molecular species of PS and PI with TPA may be applied as lipid molecular markers of coral polyps.

Distribution of lipids and fatty acids in corals by their taxonomic position and presence of zooxanthellae

MEPS Marine Ecology Progress Series Contact the journal Facebook Twitter RSS Mailing List Subscribe to our mailing list via Mailchimp HomeLatest VolumeAbout the JournalEditorsTheme Sections MEPS 409:65-75 (2010) - DOI: https://doi.org/10.3354/meps08622 Distribution of lipids and fatty acids in corals by their taxonomic position and presence of zooxanthellae Andrey B. Imbs*, Nikolay A. Latyshev, Tatyana N. Dautova, Yurii Y. Latypov A.V. Zhirmunsky Institute of Marine Biology, Far-Eastern Branch of the Russian Academy of Sciences, 17 Palchevskogo Str., 690041 Vladivostok, Russian Federation *Email: andrey_imbs@hotmail.com ABSTRACT: The lipid class and fatty acid (FA) composition for 93 species of reef-building and soft corals from the South China Sea (Vietnam) were analyzed and statistically compared to study systematic patterns of the distribution of lipids in corals and the influence of zooxanthellae on the lipids of symbiont-host association. The lipid and FA compositions of hexacorals and octocorals significantly correlated with their taxonomic position, but the lipid features of species within each of these systematic groups mainly depended on the presence of zooxanthellae. The hexacorals had lower content of polar lipids (PL), sterols (ST), and monoalkyldiacylglycerols (MADAG), but higher content of triacylglycerols (TG) and wax esters (WE) than the octocorals. On average, zooxanthellate species contained less structural lipids (PL+ST), but more MADAG when compared to azooxanthellate species. Tetracosapolyenoic acids 24:5n-6 and 24:6n-3 were chemotaxonomic markers for octocorals, whereas 22:5n-6 was a marker for Milleporidae. A strong correlation was apparent between zooxanthellate coral family and/or genus and the content of the unsaturated FA; 12 FAs were significant for the separation of azooxanthellate and zooxanthellate specimens. The latter had lower concentrations of 7-Me-16:1n-10, 18:1n-7, and six C20–24 polyunsaturated FA, but higher concentrations of 16:0, 16:2n-7, 18:3n-6, and 18:4n-3. The presence of >2% of 18:3n-6 and 18:4n-3 of total FA is characteristic of zooxanthellate corals. An inverse correlation was established between the content of 18:3n-6 and 16:2n-7 in zooxanthellate soft corals. The present study highlights the importance of zooxanthellae in coral lipid metabolism, especially when compared with symbiont-host exchanges in reef-building and soft corals. KEY WORDS: Lipid classes · Fatty acids · Hexacorallia · Octocorallia · Zooxanthellae · Biomarkers · Chemotaxonomy · Coral reef ecology Full text in pdf format Supplementary material PreviousNextCite this article as: Imbs AB, Latyshev NA, Dautova TN, Latypov YY (2010) Distribution of lipids and fatty acids in corals by their taxonomic position and presence of zooxanthellae. Mar Ecol Prog Ser 409:65-75. https://doi.org/10.3354/meps08622Export citation RSS - Facebook - Tweet - linkedIn Cited by Published in MEPS Vol. 409. Online publication date: June 23, 2010 Print ISSN: 0171-8630; Online ISSN: 1616-1599 Copyright © 2010 Inter-Research.

Distribution of lipids and fatty acids in the zooxanthellae and host of the soft coral Sinularia sp.

The lipid classes and the fatty acid (FA) compositions of the zooxanthellae, the host tissue, and intact coral were determined for the first time in a soft coral, Sinularia sp. The contents of monoalkyldiacylglycerol (MADAG), triacylglycerol, and polar lipids differed significantly between the zooxanthellae and the host fractions. The zooxanthellae were rich in polar lipids, whereas neutral lipids were concentrated in the host. MADAG comprised 35% of the host lipids and was practically absent in zooxanthellae. Hence, MADAG is only synthesized in animal tissues and serves as a biomarker for the host in the host–zooxanthellae association of these soft corals. Similar to the zooxanthellae of reef-building corals, the main FA in the zooxanthellae of Sinularia sp. were 18:4n-3, 20:5n-3, and 22:6n-3. In addition, 16:3n-4 and 16:4n-1 (8.9% in total) were found in these zooxanthellae. The ratios of 16:3n-4, 16:4n-1, 18:4n-3, 20:5n-3, and 22:6n-3 in the zooxanthellae to those in the host tissue were 4.2, 11.2, 10.1, 11.0, and 9.1, respectively. The proportions of some FA and lipid classes in the intact coral and its fractions showed that zooxanthellate lipids comprised 36 ± 15% of the total lipids in Sinularia sp. Two tetracosapolyenoic acids (24:5n-6 and 24:6n-3) are proposed as a biomarkers of the animal tissue and indicators of the purity of the zooxanthellae fractions from soft corals.

Fatty Acids of Heliopora coerulea and Chemotaxonomic Significance of Tetracosapolyenoic Acids in Coelenterates

GLC investigation of FA composition of solar coral Heliopora coerulea (Helioporidae, Octacorallia) has revealed the presence of tetracosahexaenoic acid 24:6(n -3) in amounts about 2% of total fatty acids. Earlier, tetracosapolyenoic acids were detected in representatives of all other orders of the subclass Octacorallia: in Alcyonaria, Gorgonaria, and Pennatularia. Therefore, tetracosapolyenoic acids are characteristic for species relating to subclass Octacorallia. The other main fatty acids (over 1% of total fatty acid sum) of H. coerulea were, in descending order, 16:0, 18:3(n-6), 18:0, 20:5(n-3), 14:0, 22:6(n-3), 18:4(n-3), 16:1(n-7), 18:1 (n-9), 18:2(n-6), and phytanic.

Phospholipid Fatty Acid Composition of Gorgonians of the Genus Eunicea: Further Identification of Tetracosapolyenoic Acids

The phospholipid fatty acid composition of the Caribbean gorgonian corals Eunicea fusca (Duchassaing and Michelotti), Eunicea laciniata (Duchassaing and Michelotti), Eunicea mammosa (Lamouroux), Eunicea succinea (Pallas), and Eunicea sp. is described for the first time. The main phospholipids identified were phosphatidylethanolamine, phosphatidylcholine, and phosphatidylserine. All five gorgonians presented a similar phospholipid fatty acid composition. The main fatty acids were 16:0, 18:3 (n − 6), 18:4 (n − 3), 20:4 (n − 6), 22:6 (n − 3), 24:5 (n − 6), and 24:6 (n − 3). In all of the studied Eunicea gorgonians, the tetracosapolyenoic fatty acids 24:5 (n − 6) and 24:6 (n − 3), as well as the (Z) and (E) isomers of 7-methyl-6-hexadecenoic acid, were identified. On the other hand, E. fusca and E. laciniata contained, in trace amounts, the unusual 19:4 (n − 3) acid, while E. succinea contained the recently reported 14-methyl-5,9-pentadecadienoic acid. In all of the five studied gorgonians n − 6 polyunsaturated fatty acids predominated. These findings expand the occurrence of tetracosapolyenoic fatty acids to the Eunicea.

Identification of the novel antimicrobial fatty acid (5Z,9Z)-14-methyl-5,9-pentadecadienoic acid in Eunicea succinea.

The phospholipid fatty acid composition of Eunicea succinea was investigated, and the novel (5Z,9Z)-14-methyl-5,9-pentadecadienoic acid was identified. Structural characterization was accomplished by means of mass spectrometry of its pyrrolidide derivative, NMR, FT1R, and total synthesis. Other interesting phospholipid fatty acids in E. succinea were the tetracosapolyenoic acids 6,9,12,15,18,21-tetracosahexaenoic acid (24:6) and 6,9,12,15,18-tetracosapentaenoic acids (24:5). The title compound was particularly active against Gram-positive bacteria such as Staphylococcus aureus (MIC 0.24 mumol/mL) and Streptococcus faecalis (MIC 0.16 mumol/ mL).

Phospholipid fatty acid composition of gorgonians of the genus Pseudopterogorgia: Identification of tetracosapolyenoic acids

The phospholipid fatty acid composition of the Caribbean gorgonians Pseudopterogorgia acerosa (Pallas), Pseudopterogorgia americana (Gmelin), Pseudopterogorgia bipinnata (Verrill) and Pseudopterogorgia rigida (Bielschowsky) is described for the first time. The main phospholipids identified were phosphatidylethanolamine, phosphatidylcholine and phosphatidylserine. All four gorgonians presented a similar phospholipid fatty acid composition. The main fatty acids were 16:0, 18:3(n-6), 18:4(n-3), 20:4(n-6), 22:6(n-3), 24:5(n-6) and 24:6(n-3). In all of the studied Pseudopterogorgia gorgonians, high amounts of the tetracosapolyenoic fatty acids 24:5(n-6) and 24:6(n-3) were identified. In the four gorgonians studied, n-6 polyunsaturated fatty acids predominated. These results suggest that the occurrence of tetracosapolyenoic fatty acids in the Gorgoniidae is more general than previously recognized.

New branched-chain fatty acids from the Senegalese gorgonian Leptogorgia piccola (white and yellow morphs).

Fatty acids from total lipids of the gorgonian Leptogorgia piccola (white and yellow morphs), collected from the same area at two different periods with regard to the average water temperature, were studied. More than fifty fatty acids were identified as methyl esters and N-acyl pyrrolidides by gas chromatography and gas chromatography/mass spectrometry. Three new, branched-chain unsaturated fatty acids were identified in addition to the unusual 7-methyl-6-hexadecenoic acid, namely 10-methyl-6-hexadecenoic, 7,9-dimethyl-6-hexadecenoic, and 10-methyl-6,9-heptadecadienoic acids. Also 6,9-heptadecadienoic acid was identified. The fatty acid patterns of specimens harvested in colder waters were quite different from those harvested in warmer waters in that the former contained high amounts of methylene-interrupted polyunsaturated acids, including tetracosapolyenoic acids, especially 6,9,12,15,18-24:5 (up to 15.8% of the total acid mixture) and 6,9,12,15,18,21-24:6 (up to 5.3%). Arachidonic acid was, nevertheless, a major component in all the fatty acid mixtures studied (13.6-20.5%). Based on gas chromatography/Fourier transform infrared experiments, the double bonds were assigned the (Z) configuration. Several fatty aldehydes and their dimethyl acetals were also detected, of which the most abundant was octadecanal.

Identification, isolation and characterization of tetracosapolyenoic acids in lipids of marine coelenterates

Several tetracosapolyenoic acids (TPA) were detected in lipids of different marine coelenterates. Two of these acids were isolated and their structures were confirmed by chemical and spectral methods as all- cis-6,9,12,15,18-tetracosapentaenoic and all- cis-6,9,12,15,18,21-tetracosahexaenoic acid. Their distribution among lipids of a number of species of different classes of coelenterates from the northern and tropical seas, among neutral and polar lipids of these organisms was investigated. Significant quantities of TPA were found in all of the Octacorallia species studied. In some cases the sum of TPA reaches the level of 20% of total lipid fatty acids. The fatty acid composition of different coelenterates is also discussed.

タラバガニ卵脂質の生化学的研究-I

The acetone-soluble lipid was obtained in the yield of 70.0g. from 1050g. of unfertilized eggs (66.7g./1kg. of fresh tissue). This lipid has the following properties: acid no. 31.8; sap. no. 179.3; iodine no. 190.5; reflactive index (n20) 1.4868 and unsaponi ?? able matter 6.09%. The mixed fatty acids consisted of 2% myristic, 10% palmitic, 3% stearic, 1% arachidic, 5% zoomaric, 17% oleic, 11% eicosenoic, 4% docosenoic, 1% hexadecatrienoic, 11% octade-capolyenoic, 16% eicosopolyenoic, 13% decosapolyenoic, and 6% tetracosapolyenoic acids. The unsaponifiable matter consisted mainly of sterols. The content of provitamin D in the crude crystal of mixed sterols was 2.2%.

タラバガニ卵脂質の生化学的研究-II

The acetone-soluble lipid was obtained in the yield of 27.0g. from 1096g. of fertilized eggs (24.6g./1kg. of fresh tissue). This lipid had the following properties: acid no. 62.6; sapon. no. 177.2; iodine no. 181.4; refractive index (n20) 1.4860 and unsaponifiable matter 8.82%. The mixed fatty acids consisted of 1% myristic, 10% palmitic, 3% stearic, 1% arachidic, 7% zoomaric, 17% oleic, 13% eicosenoic, 3% docosenoic, 1% hexadecatrienoic, 13 octadecapolyenoic, 15% eicosapolyenoic, 13% docosapolyenoic, and 3% tetracosapolyenoic acids. The unsaponifiable matter consited mainly of sterols, in which no detectable amount of provitamin D was found. A discussion is presented on the changes of the lipids occurred after the fertilization of the eggs.