Abstract
This article reports the concentration and composition of the isomers of cis-icosenoic acid (20:1) in the fatty acids of various species of Japanese marine animals. The main purpose of this study is to reveal the distribution of a positional isomer, cis-7-20:1 (c7-20:1), in marine animals. Because this isomer overlaps with the c9-20:1 isomer in gas chromatography (GC) on the commonly used polar capillary columns, less information is available on its occurrence and distribution. In this study, the monounsaturated fatty acids isolated by argentation thin-layer chromatography were analyzed by GC using a highly polar capillary column, SLB-IL111 (100 m long), with the highest polarity among the commercially available GC columns. A clear separation between the c7-20:1 and c9-20:1 isomers enabled the analysis of all the isomers of 20:1 present in marine animals. The results confirmed that the c7 isomer was a minor component in the 20:1 in the pelagic fish, which is rich in the c9 and/or c11 isomers as reported previously. In contrast, the c7 isomer was one of the major isomers in flatfish, shellfish, crabs, and brittle stars. In these samples, the c13 isomer also occurred at higher concentrations rather than the c9 isomer. Because such a specific pattern of the 20:1 positional isomers was generally observed in both benthic fish and its dietary animals, the c7 isomer in the benthic fish probably originated from its diet. These marine animals are used as food in Japan, and therefore the c7-20:1 isomer is consumed by humans.
Similar content being viewed by others
References
Scrimgeour CM, Harwood JL (2007) Fatty acid and lipid structure. In: Gunstone FD, Harwood JL, Dijkstra AJ (eds) The lipid handbook, 3rd edn. CRC Press, Boca Raton, pp 1–36
Ackman RG (1980) Fish lipids. Part 1. In: Connel JJ (ed) Advances in fish science and technology. Fishing News Books, Surrey, pp 86–103
Saito H, Ishikawa S (2012) Characteristic of lipids and fatty acid compositions of the neon flying squid, Ommastrephes bartramii. J Oleo Sci 61:547–564
Mansour MP, Holdsworth DG, Forbes SE, Macleod CK, Volkman JK (2005) High contents of 24:6(n-3) and 20:1(n-13) fatty acids in the brittle star Amphiura elandiformis from Tasmanian coastal sediments. Bio Chem Syst Ecol 33:659–674
Ota T, Ando Y, Nakajima H, Shibahara A (1995) C20–C24 monounsaturated fatty acid isomers in the lipids of flathead flounder, Hippoglossoides dubius. Comp Biochem Physiol 111B:195–200
Dunstan GA, Volkman JK, Barrett SM (1993) The effect of lyophilization on the solvent extraction of lipid classes, fatty acids and sterols from the oyster Crassostrea gigas. Lipids 28:937–944
Virtue P, Mayzaud P, Albessard E, Nichols P (2000) Use of fatty acids as dietary indicators in northern krill, Maganyctiphanes norvegica, from northeastern Atlantic, Kattegat, and Mediterranean waters. Can J Fish Aquat Sci 57:104–114
Go JV, Řezanka T, Srebnik M, Dembitsky VM (2002) Variability of fatty acid components of marine and freshwater gastropod species from the littoral zone of the Red Sea, Mediterranean Sea, and Sea of Galilee. Biochem Syst Ecol 30:819–835
Pond DW, Allen CE, Bell MV, Van Dover CL, Fallick AE, Dixon DR, Sargent JR (2002) Origins of long-chain polyunsaturated fatty acids in the hydrothermal vent worms Ridgea piscesae and Protis hydrothermica. Mar Ecol Prog Ser 225:219–226
Saito H, Osako K (2007) Confirmation of a new food chain utilizing geothermal energy: unusual fatty acids of a deep-sea bivalve, Calytohena phaseoliformis. Limnol Oceanogr 52:1910–1918
Zhukova NV (2007) Lipid classes and fatty acid composition of the tropical nudibranch mollusks Chromodoris sp. and Phyllidia coelestis. Lipids 42:1169–1175
Kebir MVOE, Barnathan G, Gaydou EM, Siau Y, Miralles J (2007) Fatty acids in liver, muscle and gonad of three tropical rays including non-methylene-interrupted dienoic fatty acids. Lipids 42:525–535
Pond DW, Fallick AE, Stevans CJ, Morrison DJ, Dixon DR (2008) Vertebrate nutrition in a deep-sea hydrothermal vent ecosystem: fatty acid and stable isotope evidence. Deep-Sea Res I 55:1718–1726
Saito H, Marty Y (2010) High levels of icosapentaenoic acid in the lipids of oyster Crassostrea gigas ranging over both Japan and France. J Oleo Sci 59:281–292
Kharlamenko VI, Brandt A, Kiyashko SI, Würzberg L (2013) Trophic relationship of benthic invertebrate fauna from the continental slope of the Sea of Japan. Deep-Sea Res II 86–87:34–42
Saito H, Aono H (2014) Characteristics of lipid and fatty acid of marine gastropod Turbo cornutus: high levels of arachinonic and n-3 docosapentaenoic acid. Food Chem 145:135–144
Shimizu K, Ando Y (2012) Gas chromatographic separation of docosenoic acid positional isomers on an SLB-IL100 ionic liquid column. J Oleo Sci 61:421–426
Delmonte P, FardinKia AR, Hu Q, Rader JI (2009) Review of methods for preparation and gas chromatographic separation of trans and cis reference fatty acids. J AOAC Int 92:1310–1326
Ando Y, Sasaki T (2011) GC separation of cis-eicosenoic acid positional isomers on an ionic liquid SLB-IL100 stationary phase. J Am Oil Chem Soc 88:743–748
Nakamura Y, Shimizu K, Ando Y (2014) Gas chromatographic equivalent chain length (ECL) values of fatty acid methyl esters on a highly polar ionic liquid column, SLB-IL111. Bull Fish Sci Hokkaido Univ 64:9–16
Bligh EG, Dyer WJ (1959) A rapid method of total lipid extraction and purification. Can J Biochem Physiol 37:911–917
Hara A, Taketomi T (1988) Chemical study of the mechanism for conversion of dimethylacetal obtained by methanolysis of plasmalogen to alkenylmethylether. J Biochem 104:1011–1015
Wilsona R, Lyalla K, Paynea JA, Riemersmaa RA (2000) Quantitative analysis of long-chain trans-monoenes originating from hydrogenated marine oil. Lipids 35:681–687
Ratnayake WN, Ackman RG (1979) Fatty alcohols in capelin, herring and mackerel oils and muscle lipids: II. A comparison of fatty acids from wax esters with those of triglycerides. Lipids 14:804–810
Ackman RG (1982) Fatty acid composition of fish oils. In: Barlow SM, Stansby ME (eds) Nutritional evaluation of long-chain fatty acids in fish oil. Academic Press, London, pp 25–88
Fujita T (1996) Bathymtric distribution of Ophiroids (Echinodermata) off Sendai Bay, northern Japan, with notes on the diet of the roughscale sole Clidoderma asperrimum (Pisces, Pleuronectidae). Mem Natn Sci Mus Tokyo 29:209–222
Tokranov AM, Orlov AM (2003) On the distribution and biology of roughscale sole Clidoderma asperrimum (Temminik et Schlegel, 1846) in the Pacific waters off the northern Kuril Islands and southeastern Kamchatka. Bull Sea Fish Inst 159:67–80
Ota T, Chihara Y, Itabashi Y, Takagi T (1994) Occurrence of all-cis-6,9,12,15,18,21-tetracosahexaenoic acid in flatfish lipids. Fish Sci 60:171–175
Yamamoto M, Makino H, Kobayashi J, Tominaga O (2004) Food organisms and feeding habits of larval and juvenile Japanese flounder Paralichthys olivaceus at Ohama Beach in Hiuchi-nada, the central Seto Inland Sea, Japan. Fish Sci 70:1098–1105
Hayase S, Hamai I (1974) Studies on feeding habits of three flatfishes, Cleisthenes pinetorum herzensteini (Schmidt), Hippoglossoides dubius (Schmidt) and Glyptocephalus stelleri (Schmidt). Bull Fac Fish Hokkaido Univ 25:82–99
Yang MS, Livingston PA (1986) Food habits and diet overlap of two congeneric species, Atheresthes stomias and Atherresthes evermanni, in the eastern Bering Sea. Fish Bull 82:615–623
Yang Z-H, Miyahara H, Mori T, Doisaki N, Hatanaka A (2011) Beneficial effects of dietary fish-oil-derived monounsaturated fatty acids on methabolic syndrome risk factors and insulin resistance in mice. J Agric Food Chem 59:7482–7489
Acknowledgments
We wish to thank the captain and crew of the training ship “Oshoro-maru” of the Faculty of Fisheries, Hokkaido University, for collecting the samples of flatfish and brittle star in the Bering Sea.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Nakamura, Y., Fukuda, Y., Shimizu, K. et al. Occurrence and distribution of cis-7-icosenoic acid in the lipids of Japanese marine fish, shellfish, and crustaceans. Fish Sci 80, 613–620 (2014). https://doi.org/10.1007/s12562-014-0740-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12562-014-0740-z