Advertisement

Journal of the American Oil Chemists' Society

, Volume 89, Issue 10, pp 1873–1884 | Cite as

Regiospecific Analysis of Shark Liver Triacylglycerols

  • Chamila Jayasinghe
  • Naohiro Gotoh
  • Shun Wada
Original Paper

Abstract

The liver oils of six shallow-water shark species, silky (Carcharhinus falciformis), thresher (Alopias superciliosus), oceanic whitetip (Carcharhinus longimanus), blue (Prionace glauca), hammerhead (Sphyrna lewini) and salmon (Lamna ditropis) were analyzed with particular attention to the regioisomeric composition of triacylglycerols (TAG). The TAG compositions were analyzed by using an HPLC-evaporative light scattering detector and each molecular species identified by HPLC-atmospheric pressure chemical ionization/mass spectrometry. Major lipid components of all sharks’ oils were TAG (~80 %) made up of omega-3 polyunsaturated fatty acids at 26–40 % and 20–25 % docosahexaenoic acid (DHA). Forty different molecular species were detected in the TAG fractions. TAG consisting of one palmitic acid, one DHA and one oleic acid (12.5–19.9 %) and TAG consisting of two palmitic acids and one DHA (8.4–15.4 %) were the predominant form while 30–50 % TAG molecular species were bound to one or more DHA. Distribution of fatty acids in the primary (sn-1 and sn-3) and secondary (sn-2) position of the glycerol backbones was examined by regiospecific analysis by using pancreatic lipase and it was found that DHA was preferentially positioned at sn-2. These findings greatly extend the utilization of shark liver oils in food productions and may have a significant impact on the future development of the fish oil industry.

Keywords

Docosahexaenoic acid Fatty acids HPLC–APCI/MS Shark liver oil Regiospecific analysis Triacylglycerol sn-2 position specificity 

Abbreviations

APCI/MS

Atmospheric pressure chemical ionization/mass spectrometry

D

DHA

DAG

Diacylglycerol(s)

E

EPA

ELSD

Electron light scattering detector

FA

Fatty acid(s)

GC

Gas chromatography

HPLC

High performance liquid chromatography

MAG

Monoacylglycerol(s)

MUFA

Mono unsaturated fatty acid(s)

NMR

Nuclear magnetic resonance

O

Oleic acid

P

Palmitic acid

PUFA

Polyunsaturated fatty acid(s)

S

Stearic acid

SFA

Saturated fatty acid(s)

Sn

Stereospecific number

TAG

Triacylglycerol(s)

Notes

Acknowledgments

This study was partially financed by a scholarship offered to Chamila Jayasinghe by the Ministry of Education, Culture, Sports, Science and Technology (MONBUSHO) of Japan. We thank the late Mr. Sakichi Takahashi, Kyodo Fisheries Co. Ltd., Kesannuma, Japan for providing shark liver samples.

References

  1. 1.
    Craik JCA (1978) The lipids of six species of sharks. J Marine Biol Assoc 58:913–921CrossRefGoogle Scholar
  2. 2.
    Jayasinghe C, Gotoh N, Wada S (2003) Variation in lipid classes and fatty acid composition of salmon shark (Lamna ditropis) liver with season and gender. Com Biochem Physiol B 134:287–295CrossRefGoogle Scholar
  3. 3.
    Lack M, Sant G (2009) Trends in global shark catch and recent developments in management. TRAFFIC International, CambridgeGoogle Scholar
  4. 4.
    Mottram HR (2005) Regiospecific analysis of triacylglycerols using high performance liquid chromatography/atmospheric pressure chemical ionization mass spectrometry. In: Byrdwell WC (ed) Modern methods for lipid analysis by liquid chromatography/mass spectrometry and related techniques. AOCS press, Champaign, pp 276–297Google Scholar
  5. 5.
    Ikeda I (2000) Digestion and absorption of structured lipids. In: Christophe AR, Vriese SD (eds) Fat digestion and absorption. AOCS press, Champaign, pp 235–243Google Scholar
  6. 6.
    Wijesundara C, Ceccato C, Watkins P, Fagan P, Fraser B, Theienthong N, Perlmutter P (2008) Docosahexaenoic acid is more stable to oxidation when located at the sn-3 position of triacylglycerol compared to sn-1(3). J Am Oil Chem Soc 85:543–548CrossRefGoogle Scholar
  7. 7.
    Bligh EG, Dyer WJ (1959) A rapid method of total lipid extraction and purification. Can J Biochem Physiol 37:911–917CrossRefGoogle Scholar
  8. 8.
    Luddy FE, Barford RA, Herb SF, Magidman P, Reimenschneider RW (1963) Pancreatic lipase hydrolysis of triglycerides by a semi micro technique. J Am Oil Chem Soc 41:693–696CrossRefGoogle Scholar
  9. 9.
    Suarez ER, Mugford PF, Rolle AJ, Burton IW, Walter JA, Kralovec JA (2010) 13C-NMR regioisomeric analysis of EPA and DHA in fish oil derived triacylglycerol concentrates. J Am Oil Chem Soc 87:1425–1433CrossRefGoogle Scholar
  10. 10.
    Wada S, Koizumi C, Nonaka J (1977) Analysis of triglycerides of soybean oil by high-performance liquid chromatography in combination with gas liquid chromatography. J Jpn Oil Chem Soc (Yukagaku) 26:95–99CrossRefGoogle Scholar
  11. 11.
    Christie WW (1993) Evaporative light-scattering detectors in lipid analysis. Lipid Tech 5:68–70Google Scholar
  12. 12.
    Akoh CC (2002) Structure lipids. In: Akoh CC, Min DB (eds) Food lipids: chemistry nutrition and biotechnology. Marcel Dekker Inc., New York, pp 877–908Google Scholar
  13. 13.
    Nwosu CV, Boyd LC (1997) Positional distribution of fatty acids on triacylglycerols of menhaden (Brevoortia tyrannis) and salmon (Salmo salar) oils. J Food Lipids 4:65–74CrossRefGoogle Scholar
  14. 14.
    Iverson SJ, Sampugana J, Oftedai OT (1992) Positional specificity of gastric hydrolysis of long chain n-3 polyunsaturated fatty acids of seal milk triglycerides. Lipids 27:870–878CrossRefGoogle Scholar
  15. 15.
    Andrikopoulos NK (2002) Chromatographic and stereospecific methods in the analysis of triacylglycerol species and regiospecific isomers of oils and fats. Crit Rev Food Sci Nutr 42:473–505CrossRefGoogle Scholar
  16. 16.
    Wada S (2001) Lipid analysis of PUFA in the new millennium and future trends. J Oleo Sci 50:329–338CrossRefGoogle Scholar
  17. 17.
    Standal IB, Axelson DE, Aursand M (2009) Differentiation of fish oils according to species by 13C-NMR regiospecific analysis of triacylglycerols. J Am Oil Chem Soc 86:401–407CrossRefGoogle Scholar
  18. 18.
    Aursand M, Jorgensen L, Grasdalen H (1995) Positional distribution of ω-3 fatty acids in marine lipid triacylglycerols by high-resolution 13C Nuclear magnetic resonance spectroscopy. J Am Oil Chem Soc 72:293–297CrossRefGoogle Scholar
  19. 19.
    Wanasundara U, Shahidi F (1997) Positional distribution of fatty acids in triacylglycerols of seal blubber oil. J Food Lipids 4:51–64CrossRefGoogle Scholar
  20. 20.
    Gotoh N, Matsumoto Y, Nagai T, Mizobe H, Otake I, Ichioka K, Kuroda I, Watanabe H, Noguchi N, Wada S (2011) Actual ratios of triacylglycerol positional isomers consisting of saturated and highly unsaturated fatty acids in fishes and marine mammals. Food Chem 127:467–472CrossRefGoogle Scholar

Copyright information

© AOCS 2012

Authors and Affiliations

  1. 1.Department of Food Science and TechnologyTokyo University of Marine Science and TechnologyTokyoJapan
  2. 2.Department of Food Science and Technology, Faculty of Livestock, Fisheries and NutritionWayamba University of Sri LankaMakanduraSri Lanka

Personalised recommendations