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To assess the biodiversity of symbiotic dinoflagellates (SD) in hydrocorals, we compared the molecular species compositions of four SD lipid classes such as diacylglyceryl-3-O-carboxyhydroxymethylcholine (DGCC), digalactosyldiacylglycerol (DGDG), monogalactosyldiacylglycerol (MGDG), and sulfoquinovosyldiacylglycerol (SQDG) in Millepora dichotoma and M. platyphylla collected in shallow waters of Vietnam. A statistical analysis showed significant differences in the SD lipid composition between the hydrocoral species. These differences were influenced rather by the lipid molecules of outer membrane (DGCC and DGDG) than by the lipids of chloroplast and thylakoid membranes in SD (MGDG and SQDG). As for the fatty acid (FA) composition of lipid molecules that allow discrimination of hydrocoral SDs, the medium-chain FA 18:4 was characteristic of M. dichotoma, while the long- and very-long-chain FAs (20:5, 22:6, and 28:8) were characteristic of M. platyphylla. Thus, two different Millepora species hosted different SD groups, which had similar thylakoid lipidomes, different lipid profiles of outer membrane, and different activities in biosynthesis of n-3 polyunsaturated FAs. The lipidomic approach has shown that the M. dichotoma population is heterogenic, and about 10% of its colonies can be infected with SDs that are common for M. platyphylla.

The chemical structures and contents of 68 molecular species of ethanolamine glycerophospholipids (PE), choline glycerophospholipids (PC), serine glycerophospholipids (PS), and inositol glycerophospholipids (PI) were determined in the asymbiotic soft coral Gercemia rubiformis (Ehrenberg, 1834) from the Sea of Okhotsk by the method of tandem high-resolution mass spectrometry. The major molecular species were 16:1e/20:4 PE, 16:0e/20:4 PC, 20:1/24:5 PS, and 16:0/24:5 PI. This study showed a significant similarity of the polar lipidomes of G. rubiformis and tropical species of alcyonarians with symbiotic microalgae and revealed the basic characteristic of the polar lipidome of these alcyonarians. It was found that the 24:5n-6 and 24:6n-3 acids (chemotaxonomic markers of soft corals) concentrate in the acyl groups of the molecular species of PS and PI, which can be used as molecular lipid markers in the study of the symbiotic and trophic relationships of soft corals.

A method that uses marker fatty acids (FAs) is widely applied in investigations of trophic and symbiotic relationships. In a search for new lipid markers, we determined the total lipid FA composition, as well as the composition of molecular species of mono- and digalactosyl diacylglycerols (MGDGs and DGDGs), which are specific galactolipids of thylakoid membranes, in zooxanthellae (endosymbiotic dinoflagellates) of the tropical soft coral Capnella sp. Some FAs of zooxanthellae were suggested for use as marker polyunsaturated FAs (PUFAs). Thirteen molecular species of MGDGs and ten molecular species of DGDGs were detected using the method of high-resolution tandem mass spectrometry. All marker PUFAs of zooxanthellae were found in acyl groups of galactolipids. The major molecular species of DGDGs (18:4/18:4, 18:4/20:5, and 16:2/22:6) and the unique molecular species of MGDGs (16:4/18:5) were described. The identification of several polyunsaturated molecular species of galactolipids that contain marker FAs allowed us to propose that this lipid group be used as molecular lipid markers of zooxanthellae for the study of symbiont–host interactions in soft corals.

Lipid class and fatty acid (FA) compositions of the zoanthid Palythoa caesia from the South China Sea (Vietnam) were determined and compared with those of zooxanthellate reef-building and soft corals from the same region to clarify chemotaxonomic relations between zoanthids and corals. Total lipids of P. caesia and corals were formed by the same lipid classes. The lipids of P. caesia contained specific for cnidarians monoalkyldiacylglycerols and phosphonolipids. The proportion between reserve and structural lipid classes of P. caesia was similar to that of alcyonarians (soft corals), but significantly differed from reef-building corals. This similarity may be caused by the similar energy budget of cnidarian colonies without hard exoskeleton. The distribution of polyunsaturated FAs (PUFAs), such as 22:4n-6 and 22:5n-3, indicated pathways of biosynthesis of PUFAs in Palythoa to be closer to those in reef-building corals than in soft corals. The differences in the profiles of common FAs between P. caesia and reef-building corals were showed. Zoanthid lipids contained rare Δ5,9 non-methylene-interrupted (NMI) PUFAs (with two and three double bounds), which probably originated from microorganisms associated with P. caesia. Trienoic acids Δ5,9,15–24:3 and Δ5,9,17–24:3 were found in Palythoa for the first time. NMI PUFAs, as well as total FA profile, can be used for chemotaxonomy of Palythoa.

High diversity of fatty acid (FA) composition of endosymbiotic dinoflagellates of the Symbiodinium group (zooxanthellae) isolated from different cnidarian groups has been found. To explain this diversity, FA composition of the total lipids of pure symbiont fractions (SF) and host cell tissue fractions (HF) isolated from one hydrocoral, two soft coral, and seven hard coral species inhabiting the shallow waters of the South China Sea (Vietnam) were compared. Symbiodinium phylogenetic clade designation for each SF was also determined, however, the relationship between the clade designation and FA composition of Symbiodinium was not found. The profiles of marker polyunsaturated FAs (PUFAs) of symbionts (18:4n-3, 18:5n-3, 20:5n-3) did not depend on taxonomic designation of the host and reflected only a specimen-specific diversity of the SF lipids. Several FAs such as 20:0, C24 PUFAs, 22:5n-6, and 18:2n-7 concentrated in HF lipids but were also found in SF lipids. For ten cnidarian species studied, the principal components analysis of total FAs (27 variables) of the symbiotic fractions was performed. The clear division of the symbiotic dinoflagellates according to the host systematic identity was found on a subclass level. This division was mainly caused by the FAs specific for the host lipids of each cnidarian subclasses such as hard corals, soft corals, and hydrocorals. Thus, the coral hosts affect the FA profile of their symbionts and cause the diversity of FA composition of Symbiodinium. The transfer of FAs from the coral host to their symbiotic dinoflagellates and modulation of PUFA biosynthesis in symbionts by the host are considered as possible reasons of the diversity studied.

This paper reviews the literature data on the composition, structure, and distribution of the main lipid classes and their fatty acids in reef-building and soft corals and in hydrocorals of the genus Millepora. The review presents information about more than 150 coral species from tropical and cold waters of the World Ocean, as well as data on the influence of environmental factors on the lipid compositions of corals. The possible pathways of polyunsaturated fatty acid biosynthesis in corals are discussed.

Fatty acids (FAs) composition of eight zooxanthellate soft corals,Sinularia leptoclados, S. flexibilis, S.aff.deformis, S. lochmodes, S. cf.muralis, S. densa, S. notandaandS. cruciatacollected in Van Phong Bay (Vietnam) were studied to identify possible origin of unsaturated FAs. The main FAs were 14:0, 16:0, 7-Me-16:1n-10, 16:1n-7, 16:2n-7, 18:0, 18:1n-9, 18:4n-3, 20:4n-6, 20:5n-3, 22:6n-3, 24:5n-6 and 24:6n-3. On the average, saturated, monounsaturated, and polyunsaturated FAs (PUFAs) contributed 35.6, 6.2 and 54.0% of total coral FAs, respectively. PUFAs of n-6 series predominated in all animals (n-6/n-3 > 1.6). The content of 20:4n-6 varied from 10.2 to 23.8%. The main n-3 PUFA was 18:4n-3 (on the average, 5.4%); the contribution of 20:5n-3 and 22:6n-3, typical PUFAs of marine organisms, was not more than 2.4 and 3.9%, respectively. InSinularia, PUFAs were produced by endosymbiotic dinoflagellates (zooxanthellae) and the coral host tissue, or obtained with food. Zooxanthellae can be considered as the source of C16PUFAs and 18:4n-3. The coral host synthesized 18:2n-7, 24:5n-6 and 24:6n-3 acids. The low content of 18:1n-7, saturated odd-chain FAs and saturated methyl-branched FAs indicated a negligible contribution of bacteria to total lipids ofSinularia. A comparison of the levels of diatom and dinoflagellate FA markers in coral and plankton lipids showed eukaryotic microalgae to play a secondary role in feeding ofSinularia. The high level of 20:4n-6 may be considered as an indicator of heterotrophic feeding ofSinularia.

The fatty acid (FA) composition and the content of the prostaglandin PGE2 were determined in the red algae Gracilaria vermiculophylla and G. austramaritima from Peter the Great Bay (Sea of Japan), as well as in G. tenuistupitata, G. nhangii, and G. bailiniae from lagoons in southern Vietnam (in the South China Sea). Polyunsaturated FA (PUFA) comprised 49–56% of the total FAs in algae from the Sea of Japan, while in algae from the South China Sea their share was 20% at most. The content of arachidonic acid (20:4n-6) in the total FAs of G. vermiculophylla was as high as 45.4%, while the level of 20:4n-6 in Gracilaria from coastal waters of Vietnam did not exceed 12.5%. G. austramaritima stood out for its high content of eicosapentaenoic acid 20:5n-3 (33.5%). The ratios of 20:4n-6/20:5n-3 in G. vermiculophylla, G. austramaritima, G. tenuistupitata, G. changii, and G. bailiniae were 10.6, 0.3, 3.9, 4.0, and 1.5, respectively. The content of PGE2 was the highest (286 μg/g dry weight) in G. vermiculophylla from the Sea of Japan and did not exceed 20 μg/g dry weights in other Gracilaria species. This study showed that it is possible to introduce G. vermiculophylla from the Sea of Japan into the mariculture of northern Vietnam. In the experiment, during 3 weeks of cultivation, the biomass of introduced Gracilaria increased 1.2–1.3 times in a sea lagoon in Vietnam and 1.5–2 times in an aquarium; the algal growth rates were 1.57 ± 0.21% per day. In cultivated Gracilaria, the level of 20:4n-6 decreased to 5.9% (20:4n-6/20:5n-3 = 2.3) and the level of PGE2 decreased to 12 μg/g in dry weight. The PUFA compositions of G. vermiculophylla from various natural populations differed insignificantly; however, the stress caused by introduction led to a sharp reduction in the content of 20:4n-6, which was probably connected with a decreased biosynthesis rate of PUFAs of the n-6 series. At the same time, approximately equal amounts of PGE2 methyl ester were extracted from natural and cultivated G. vermiculophylla after treatment by a method proposed for obtaining prostaglandins. Thus, the cultivation conditions evidently did not influence the prostaglandin biosynthesis enzyme complex in G. vermiculophylla; this species, when grown in mariculture, can be used as a source of prostaglandins.

Coral bleaching induces changes in lipid and fatty acid composition that result in low lipid content, reducing the likelihood of coral survival. Species-specific differences in the metabolism of lipid reserves may contribute to the differential resistance of corals under acute heat exposures. Here, we examined the dynamics of lipids and fatty acid abundance in corals subjected to short-term heat stress. The stony corals Acropora intermedia, Montipora digitata, and the soft coral Sinularia capitalis all showed a 60–75% decline in both storage and structural lipids. However, S. capitalis and M. digitata exhibited no significant change in the percentages of structural lipids (i.e., polar lipids and sterols) until they had lost 90–95% of their endosymbionts, whereas A. intermedia showed a rapid decline in structural lipids after a 50% loss of symbionts. After a 90–95% loss of symbionts under heat stress, all three corals showed a relative depletion of polyunsaturated fatty acids that had symbiont biomarkers, suggesting that polyunsaturated fatty acids were translocated from the symbiont to the coral host tissue.

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 system- atic 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 system- atic 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 triacyl- glycerols (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. Tetracos- apolyenoic 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 fam- ily 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 zoo- xanthellate 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.

The relationship between taxonomic position and the lipid composition of octocorals from coastal waters of Vietnam was investigated. The principal component analysis of the total fatty acid (FA) composition of 64 coral specimens showed that total FAs are markers at the family level. A good distinction was obtained between antipatarians, gorgonians, and alcyonarians. Azooxanthellate corals of the genus Dendronephthya formed a separate group. The alcyonarian genera Sinularia, Lobophytum, and Sarcophyton were distinguished only by the composition of polyunsaturated FAs. The taxon-specific composition of FAs in octocorals is likely to be determined by differences in the nutrition of food sources, symbiont composition, and the enzymatic activity of FA biosynthesis.

Sixteen scleractinian species of six coral families (Acroporidae, Pocilloporidae, Poritidae, Faviidae, Pectiniidae, and Fungiidae) from Vietnam were analyzed for fatty acid (FA) composition. Except for the Poritidae species, total lipids of the corals had the same set of FAs, about 50% of them being unsaturated acids. Some coral families had high levels of characteristic FAs: 20:3(n-6), 20:4(n-3), and 22:6(n-3) in Pocilloporidae; 18:1(n-9) and 22:6(n-3) in Poritidae; and 18:3(n-6) and 22:5(n-3) in Faviidae. For the first time in hexacorals, unsaturated C(24) FAs (24:1(n-9), 24:2(n-6), 24:2(5,9), 24:3(5,9,17), and 24:4(n-3)) were discovered in the Poritidae species. The highest level of 18:1(n-7), odd-chain and branched FAs (7.5% in total) was detected in Sandalolitha robusta. The data obtained on the contents of ten principal C(18)-C(22) polyunsaturated FAs (PUFAs) for the 16 specimens were combined with data on the 19 reef-building coral specimens investigated previously and subjected to multidimensional scale analysis (MSA). The representative coral families (Acroporidae, Pocilloporidae, Poritidae, Faviidae, Dendrophylliidae, and Milleporidae) were separated by MSA according to the composition of their principal PUFAs. Therefore, PUFAs may serve as chemotaxonomic markers for reef-building corals at the family level. Family-specific compositions of coral zooxanthellae characterized by different PUFA profiles, which affect the PUFA content of whole coral colonies, were supposed to be the probable cause of the discovered chemotaxonomic distinctions between reef-building corals.

The intra-and interspecific variability of fatty acid (FA) composition of soft corals was examined in the tropical alcyonarian Sarcophyton sp., tropical gorgonian Euplexaura erecta, and boreal alcyonarian Gersemia rubiformis. Characteristic significant differences in the FA composition were found between these species belonging to different taxonomic groups and habitats. We assume that the FA groups 14: 0 + 16: 0 + 18: 3n-6, 16: 2 + 20: 4n-6 + 24: 5n-6, and 18: 1n-7 + 20: 1n-7 + 20: 5n-3 + 24: 6n-3 are characteristic of Sarcophyton sp., E. erecta, and G. rubiformis respectively. There were no significant differences (p > 0.05) between the three soft coral species in the content of oleic, linoleic, and docosahexaenoic acids. The relative content of more than 45% of individual FA did not significantly differ (p > 0.05) between the pairs of species, i.e., intraspecific variations exceeded interspecific ones. The reasons for intraspecific variability of soft coral FA composition are discussed. Control of this variability is needed when using individual FA as chemotaxonomic and food markers.

Total lipid, phospholipid, and FA composition and distribution of FA between polar lipids (PL) and neutral lipids (NL) were investigated in the boreal soft coral Gersemia rubiformis from the Bering Sea. The total lipids were mostly hydrocarbons and waxes (33.7%) and PL (33.1%). The content of monoalkyldiacylglycerols (9.7%) exceeded the content of TAG (6.7%). PC and PE constituted 31.4% and 25.6% of total phospholipids, respectively. Principal FA were 16:0, 16:1n-7, 18:0, 18:1n-9, 18:1n-7, 20:1n-7, 20:4n-6, 20:4n-3, 20:5n-3, 22:5n-3, 22:6n-3, 24:5n-6, and 24:6n-3. Most n-6 PUFA (52% of total FA) were associated with the PL fraction; this was especially true for arachidonic and tetracosapentaenoic acids. The NL were enriched with mono-, di-, trienoic, and n-3 PUFA. The variation in EPA levels in both NL and PL suggests an origin of this acid from lipids of diatoms consumed by the corals.

Carbon and sulfur stable isotope ratios, as well as fatty acid composition of tissues, of dominant consumer species were determined and compared to those of potential food sources in an isolated community of Zostera marina in a shallow, semi-enclosed inlet of the Sea of Japan. Of the 6 dominant species of invertebrates, 4 species were enriched in 13 C, compared to all sampled carbon sources alternative to Z. marina. Among them, the grazing gastropods Littorina squalida and Homa- lopoma sangarense exhibited the most enriched δ 13 C values. On the dual δ 13 C versus δ 34 S plot, these mollusks occupy an intermediate position between Z. marina and epiphytes, suggesting nearly equal proportions of organic carbon from both nutritional sources. In lipids of H. sangarense there was a high content of the 18:1(n-7) acid characteristic of aerobic bacteria; however, another grazer (L. squalida) showed the lowest content of bacterial fatty acids among all consumers. Other highly 13 C-enriched consumers were the surface-deposit-feeding mollusks, the gastropod Batillaria cumingii and the bivalve Macoma incongrua; however, their δ 34 S values were markedly lower than those of any of the primary producers sampled, including Z. marina. Although the high δ 13 C values of grazers and surface-deposit feeders are suggestive of a great contribution of Z. marina organic car- bon, no substantial concentrations of seagrass marker fatty acids were detected. Significant interspe- cific variations of both the sulfur isotope ratios and the fatty acid composition of these consumers sug- gest that there are a variety of pathways by which seagrass organic matter reaches invertebrates at lower trophic levels of the community food web. Dominant filter feeders, the bivalves Ruditapes philippinarum and Pillucina pisidium, had carbon drastically different in isotopic composition from Z. marina organic matter. Body tissues of P. pisidium and especially its gills, which bear symbiotic bacteria, were dramatically depleted both in 13 C and 34 S compared to all sources of photosyntheti- cally fixed carbon in the bay. Very low δ 13 C and δ 34 S values of P. pisidium body together with a high content of 18:1(n-7) acid suggest a leading role of sulfur-oxidizing symbiotic bacteria in the nutrition of this species. R. philippinarum was only slightly 13 C-enriched, compared to POM, and was the only consumer which had the high concentration of fatty acids characteristic of plankton, particularly 22:6(n-3). At the same time, it was much more 34 S-depleted than would be expected, assuming neg- ligible contribution of Z. marina detritus to its food. This mollusk showed a high content of branched fatty acids, especially the iso17:0 and anteiso17:0 acids characteristic of bacteria from sediment; this suggests that R. philippinarum assimilated notable amounts of bacteria from resuspended sediment. Furthermore, the contribution of 34 S-depleted bacteria, which inhabit reduced sediment, to R. philip- pinarum nutrition was high enough to result in the observed depletion of 34 S in mollusks. Further progress in food web studies of seagrass ecosystems using a complex of multiple stable isotope and fatty acid analyses would appear possible on the basis of analysis of separate components of the sea- grass epiphytic community and micro- and meiobenthic organisms, inhabiting surface sediments.

Seven zooxanthellae-free species of octocorals (the genera Acanthogorgia, Acabaria, Chironephthya, Echinogorgia, Menella, Ellisella, and Bebryce) and two zooxanthellate octocorals (the genera Paralemnalia and Rumphella) were examined to elucidate their fatty acid (FA) composition. Arachidonic (about 40% of the total FA) and palmitic acids were predominant in all the species studied. Seven furan FA (F-acids) (up to 9.7%) were identified in the azooxanthellate octocorals. The main F-acids were 14,17-epoxy-15-methyldocosa-14,16-dienoic and 14,17-epoxy-15,16-dimethyldocosa-14,16-dienoic acids. In all specimens of Bebryce studeri, C25–28 demospongic FA (about 20%) were identified. These FA reflect the presence of a symbiotic sponge in B. studeri and can be used as the specific markers for other corals. A significant difference (P

Ten zooxanthellae-free Dendronephthya species , twelve zooxanthellate soft coral species of the genera Sarcophyton, Lobophytum, Cladiella, Lytophyton, Cespitularia, and Clavularia, and the hermatypic coral Caulastrea tumida were examined for the first time to elucidate the fatty acid (FA) composition of total lipids. In Dendronephthya species, the main FAs were 20:4n-6, 24:5n-6, 16:0, 18:0, 7-Me-16:1n-10, and 24:6n-3 which amounted on the average to 26.0, 12.7, 12.1, 6.0, 4.8, and 4.0% of the total FA contents, respectively. For zooxanthellate soft corals, the main FAs were 16:0 (25.7%), 20:4n-6 (18.2%), 24:5n-6 (6.2%), and 18:4n-3 (5.6%), as well as 16:2n-7, which amounted up to 11.8% in Sarcophyton aff. crassum. Corals with zooxanthellae had low contents of 24:6n-3. The significant difference (p

The fatty acid and fully hydrogenated triacylglycerol composition in the seeds of Pinus massoniana, P. merkusii, P. caribea, P. kesyia, P. dalatensis, P. krempfii, P. koraiensis and P. siberya were determined. The non-methylene-interrupted polyenoic fatty acids amounted to 12.0–26.4% of total acids. The distribution of triacylglycerols of the seeds according to their molecular weights was similar to that of common seed oil. The possible chemosystematic application of the fatty acid composition of seeds of Pinaceae is discussed.

Larvae of the chironomid Stictochironomus pictulus were collected from Lake Biwa, central Japan. Both the fatty acid composition of the total lipid fraction and the carbon stable isotope ratios of whole larvae were determined. Larvae showed delta(13)C values of -57.4 per thousand to -62.4 per thousand, similar to the values of methane recorded from the lake sediments. A high level of monounsaturated fatty acids (MUFAs; approximately 50% of total fatty acids) and an extremely low level of n-3 series polyunsaturated fatty acids (PUFAs) in the total lipids of S. pictulus indicated a predominantly bacterial nutrition for this species. Moreover, chironomid tissues contained large amounts of the Type I methanotroph group-specific fatty acid, 16:1(n-8) (approximately 8% of total fatty acids). This is the first time such a fatty acid biomarker has been described from freshwater invertebrates. The data suggest that S. pictulus larvae directly feed upon methanotrophic bacteria.

The influence of solar irradiance and seasons on prostaglandin (PG) and arachidonic acid (AA) content in the marine red alga Gracilaria verrucosa (Huds.) Papenf. (unattached form) was investigated. PGA(2), PGE(2), PGF(2), and 15-keto-PGE(2) were isolated from the alga, quantitatively analyzed as 4-methyl-7-methoxycoumarin esters by high-performance liquid chromatography, and their chemical structures were confirmed by 1H NMR. In June-September, the PG content in the alga was relatively stable (420 microg/g of dry wt. of PGE(2)+PGF(2); 40 microg/g of PGA(2)) and it increased 1.5 times in October. The highest level of PGs was detected in November (2500 microg/g of PGE(2)+PGF(2); 74 microg/g of PGA(2)) when water temperature was fairly low (5-10 degrees C). Algae grown for five months at 50% of incident photosynthetic active radiation (PAR(0)) contained two times less PGE(2) and PGF(2) than algae grown under natural conditions, but the amount of these PG in algae grown at 5% of PAR(0) was close to the normal level. On the contrary, when algae were grown at 5% of PAR(0) the content of PGA(2) increased up to 4 times compared to algae cultivated at 100% PAR(0). In June-November, the amount of AA in total algal lipids slightly varied from 48.9 to 56.7% and did not virtually depend on the light intensity. The probable reasons of the PG content variation in response to environmental factors are discussed.