One-pot enzymatic synthesis of docosahexaenoic acid-rich triacylglycerols at the sn-1(3) position using by-product from selective hydrolysis of tuna oil

New Biotechnology

Volumn 28, Issue 1, 2011, Pages 7-13

  Nagao, Toshihiro ^a   Watanabe, Yomi ^a   Maruyama, Kazuaki ^b   Momokawa, Yuusuke ^c   Kishimoto, Noriaki ^c   Shimada, Yuji ^a  

^a OSAKA MUNICIPAL TECHNICAL RESEARCH INSTITUTE   (Japan)

^b Maruha Nichiro Holdings Inc   (Japan)

^c KINKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DOCOSAHEXAENOIC ACID; ENZYMATIC SYNTHESIS; FREE FATTY ACID; ONE POT; ONE POT PROCESS; REGIOSPECIFIC ANALYSIS; RHIZOMUCOR MIEHEI LIPASE; TRIACYLGLYCEROLS; TUNA OIL;

BYPRODUCTS; ESTERS; GLYCEROL; HYDROLYSIS; ISOMERS;

FATTY ACIDS;

DOCOSAHEXAENOIC ACID; FATTY ACID; TRIACYLGLYCEROL;

ARTICLE; ENZYME SYNTHESIS; ESTERIFICATION; FISH; HYDROLYSIS; INDUSTRIAL WASTE; PRIORITY JOURNAL; RHIZOMUCOR; RHIZOMUCOR MIEHEI; WATER CONTENT;

ANIMALS; CANDIDA; CHEMISTRY, ORGANIC; DOCOSAHEXAENOIC ACIDS; ENZYMES, IMMOBILIZED; ESTERIFICATION; FISH OILS; GLYCEROL; HYDROLYSIS; LIPASE; RHIZOMUCOR; STEREOISOMERISM; TEMPERATURE; TIME FACTORS; TRIGLYCERIDES; TUNA;

RHIZOMUCOR MIEHEI; SCOMBRIDAE;

EID: 78650283199     PISSN: 18716784     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nbt.2010.07.021     Document Type: Article

References (25)

1. Kromhout D., et al. The inverse relation between fish consumption and 20-year mortality from coronary heart disease. New Engl. J. Med. 1985, 312:1205-1209.
2. Lee T.H., et al. Effect of dietary enrichment with eicosapentaenoic and docosahexaenoic acids on in vitro neutrophil and monocyte leukotriene generation and neutrophil function. New Engl. J. Med. 1985, 312:1217-1224.
3. de Bravo M.G., et al. Effect of an eicosapentaenoic and docosahexaenoic acid concentrate on a human lung carcinoma grown in nude mice. Lipids 1991, 26:866-870.
4. Uauy R., de Andraca I. Human milk and breast feeding for optimal mental development. J. Nutr. 1995, 125:2278-2280.
5. Neuringer M., et al. Dietary omega-3 fatty acid deficiency and visual loss in infant rhesus monkeys. J. Clin. Invest. 1984, 73:272-276.
6. Colombo J. Recent advances in infant cognition: Implications for long-chain polyunsaturated fatty acid supplementation studies. Lipids 2001, 36:919-926.
7. Tanaka Y., et al. Concentration of docosahexaenoic acid in glyceride by hydrolysis of fish oil with Candida cylindracea lipase. J. Am. Oil Chem. Soc. 1992, 69:1210-1214.
8. Shimada Y., et al. Enrichment of polyunsaturated fatty acids with Geotrichum candidum lipase. J. Am. Oil Chem. Soc. 1994, 71:951-954.
9. Shimada Y., et al. Application of lipases to industrial-scale purification of oil- and fat-related compounds. Handbook of Industrial Biocatalysis 2005, 8.1-8.27. CRC Press. C.T. Hou (Ed.).
10. Haraldsson G.G., et al. The synthesis of homogeneous triglycerides of eicosapentaenoic acid and docosahexaenoic acid by lipase. Tetrahedron 1995, 51:941-952.
11. Kawashima A., et al. Enzymatic synthesis of high-purity structured lipids with caprylic acid at 1,3-positions and polyunsaturated fatty acid at 2-position. J. Am. Oil Chem. Soc. 2001, 78:611-616.
12. Irimescu R., et al. Utilization of reaction medium-dependent regiospecificity of Candida antarctica lipase (Novozym 435) for synthesis of 1,3-dicapryloyl-2-docosahexaenoyl (or eicosapentaenoyl) glycerol. J. Am. Oil Chem. Soc. 2001, 78:285-289.
13. Irimescu R., et al. Study of TAG ethanolysis to 2-MAG by immobilized Candida antarctica lipase and synthesis of symmetrically structured TAG. J. Am. Oil Chem. Soc. 2002, 79:879-883.
14. Shimada Y., et al. Regiospecific analysis by ethanolysis of oil with immobilized Candida antarctica lipase. Lipids 2003, 38:1281-1286.
15. Watanabe Y., et al. Control of the regiospecificity of Candida antarctica lipase by polarity. New Biotechnol. 2009, 26:23-28.
16. Huge-Jensen B., et al. Partial purification and characterization of free and immobilized lipases from Mucor miehei. Lipids 1987, 22:559-565.
17. Shimada Y., et al. Fatty acid specificity of Rhizopus delemar lipase in acidolysis. J. Ferment. Bioeng. 1997, 83:321-327.
18. Shimada Y., et al. Purification of ethyl docosahexaenoate by selective alcoholysis of fatty acid ethyl esters with immobilized Rhizomucor miehei lipase. J. Am. Oil Chem. Soc. 1998, 75:565-1571.
19. Shen Z., Wijesundera C. Evaluation of ethanolysis with immobilized Candida antarctica lipase for regiospecific analysis of triacylglycerols containing high unsaturated fatty acids. J. Am. Oil Chem. Soc. 2006, 83:923-927.
20. Iverson S.J., et al. Positional specificity of gastric hydrolysis of long-chain n-3 polyunsaturated fatty acids of seal milk triglycerides. Lipids 1992, 27:870-878.
21. Yoshida H., et al. Lymphatic absorption of seal and fish oils and their effect on lipid metabolism and eicosanoid production in rats. Biosci. Biotech. Biochem. 1996, 60:1293-1298.
22. Han J.J., Yamane T. Enhancement of both reaction yield and rate of synthesis of structured triacylglycerol containing eicosapentaenoic acid under vacuum with water activity control. Lipids 1999, 34:989-995.
23. Iwasaki Y., et al. Optical resolution of asymmetric triacylglycerols by chiral-phase high-performance liquid chromatography. J. Chromatogr. A 2001, 905:111-118.
24. Xu X., et al. Production of specific-structured lipids by enzymatic interesterification: elucidation of acyl migration by response surface design. J. Am. Oil Chem. Soc. 1998, 75:1179-1186.
25. Nagao T., et al. Improvement of a process for purification of tocopherols and sterols from soybean oil deodorizer distillate. J. Mol. Catal. B: Enzym. 2005, 37:56-62.