Docosapentaenoic acid (22:5n-3): A review of its biological effects

Progress in Lipid Research

Volumn 50, Issue 1, 2011, Pages 28-34

  Kaur, Gunveen ^a   Cameron Smith, David ^a   Garg, Manohar ^b   Sinclair, Andrew J ^a  

^a DEAKIN UNIVERSITY   (Australia)

^b UNIVERSITY OF NEWCASTLE   (Australia)

Author keywords

Docosahexaenoic acid (DHA); Docosapentaenoic acid (DPA); Eicosapentaenoic acid (EPA); n 3 Polyunsaturated fatty acids (VLCPUFA)

Indexed keywords

DOCOSAHEXAENOIC ACID; DOCOSAPENTAENOIC ACID; FATTY ACID SYNTHASE; ICOSANOID; ICOSAPENTAENOIC ACID; LIPOXYGENASE; MALATE DEHYDROGENASE (DECARBOXYLATING);

CELL MIGRATION; ENDOTHELIUM CELL; ENZYME ACTIVITY; FATTY ACID METABOLISM; FATTY ACID SYNTHESIS; GENE EXPRESSION; HUMAN; IN VITRO STUDY; IN VIVO STUDY; LEARNING; LONG TERM POTENTIATION; NONHUMAN; PRIORITY JOURNAL; REVIEW; SUPPLEMENTATION; THROMBOCYTE AGGREGATION INHIBITION; WOUND HEALING;

ANIMALS; CELL MOVEMENT; EICOSANOIDS; ENDOTHELIAL CELLS; FATTY ACIDS, UNSATURATED; GENE EXPRESSION REGULATION, ENZYMOLOGIC; HUMANS; ISOMERISM;

MUS; ORYCTOLAGUS CUNICULUS;

EID: 78650700860     PISSN: 01637827     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.plipres.2010.07.004     Document Type: Review

References (59)

1. M.A. Crawford, N.M. Casperd, and A.J. Sinclair The long chain metabolites of linoleic avid linolenic acids in liver and brain in herbivores and carnivores Comp Biochem Physiol B 54 3 1976 395 401
2. M.A. Crawford, and A.J. Sinclair Nutritional influences in the evolution of mammalian brain. Lipids, malnutrition and the developing brain Ciba Found Symp 22 1971 267 292
3. M. Arita, M. Yoshida, S. Hong, E. Tjonahen, J.N. Glickman, and N.A. Petasis Resolvin E1, an endogenous lipid mediator derived from omega-3 eicosapentaenoic acid, protects against 2,4,6-trinitrobenzene sulfonic acid-induced colitis Proc Natl Acad Sci USA 102 21 2005 7671 7676
4. H. Aktas, and J.A. Halperin Translational regulation of gene expression by omega-3 fatty acids J Nutr 134 9 2004 2487S 2491S
5. M. Tsuji, S.I. Murota, and I. Morita Docosapentaenoic acid (22:5, n-3) suppressed tube-forming activity in endothelial cells induced by vascular endothelial growth factor Prostag Leukotr Essent Fatty Acids 68 5 2003 337 342
6. K. Kitajka, L.G. Puskas, A. Zvara, L. Hackler Jr., G. Barcelo-Coblijn, and Y.K. Yeo The role of n-3 polyunsaturated fatty acids in brain: modulation of rat brain gene expression by dietary n-3 fatty acids Proc Natl Acad Sci USA 99 5 2002 2619 2624
7. M. Fujikawa, K. Yamazaki, T. Hamazaki, K. Wakaki, F. Koizumi, and S. Yano Effect of eicosapentaenoic acid ethyl ester on albuminuria in streptozotocin-induced diabetic rats J Nutr Sci Vitaminol (Tokyo) 40 1 1994 49 61
8. H. Shimizu, K. Ohtani, Y. Tanaka, N. Sato, M. Mori, and Y. Shimomura Long-term effect of eicosapentaenoic acid ethyl (EPA-E) on albuminuria of non-insulin dependent diabetic patients Diabetes Res Clin Pract 28 1 1995 35 40
9. H. Mohrhauer, and R.T. Holman Tracer experiments to assess metabolic conversions of polyunsaturated fatty acids J Am Oil Chem Soc 42 1965 639 643
10. J.D. Horton, N.A. Shah, J.A. Warrington, N.N. Anderson, S.W. Park, and M.S. Brown Combined analysis of oligonucleotide microarray data from transgenic and knockout mice identifies direct SREBP target genes Proc Natl Acad Sci USA 100 21 2003 12027 12032
11. Y. Wang, D. Botolin, B. Christian, J. Busik, J. Xu, and D.B. Jump Tissue-specific, nutritional, and developmental regulation of rat fatty acid elongases J Lipid Res 46 4 2005 706 715
12. A. Voss, M. Reinhart, S. Sankarappa, and H. Sprecher The metabolism of 7,10,13,16,19-docosapentaenoic acid to 4,7,10,13,16,19-docosahexaenoic acid in rat liver is independent of a 4-desaturase J Biol Chem 266 30 1991 19995 20000
13. X. Qiu, H. Hong, and S.L. MacKenzie Identification of a Delta 4 fatty acid desaturase from Thraustochytrium sp. involved in the biosynthesis of docosahexanoic acid by heterologous expression in Saccharomyces cerevisiae and Brassica juncea J Biol Chem 276 34 2001 31561 31566
14. T. Tonon, D. Harvey, T.R. Larson, and I.A. Graham Identification of a very long chain polyunsaturated fatty acid Delta 4-desaturase from the microalga Pavlova lutheri FEBS Lett 553 3 2003 440 444
15. H. Mohrhauer, and R.T. Holman Effect of linolenic acid upon the metabolism of linoleic acid J Nutr 81 1963 67 74
16. H. Mohrhauer, and R.T. Holman The effect of dietary essential fatty acids upon composition of polyunsaturated fatty acids in depot fat and erythrocytes of the rat J Lipid Res 4 1963 346 350
17. H. Mohrhauer, and R.T. Holman The effect of dose level of essential fatty acids upon fatty acid composition of the rat liver J Lipid Res 4 1963 151 159
18. G.C. Burdge, and P.C. Calder Conversion of alpha-linolenic acid to longer-chain polyunsaturated fatty acids in human adults Reprod Nutr Dev 45 5 2005 581 597
19. G.C. Burdge, A.E. Jones, and S.A. Wootton Eicosapentaenoic and docosapentaenoic acids are the principal products of alpha-linolenic acid metabolism in young men Br J Nutr 88 4 2002 355 363
20. G.C. Burdge, and S.A. Wootton Conversion of alpha-linolenic acid to eicosapentaenoic, docosapentaenoic and docosahexaenoic acids in young women Br J Nutr 88 4 2002 411 420
21. J.T. Brenna, N. Salem Jr., A.J. Sinclair, and S.C. Cunnane Alpha-linolenic acid supplementation and conversion to n-3 long-chain polyunsaturated fatty acids in humans Prostag Leukotr Essent Fatty Acids 80 2-3 2009 85 91
22. Z. Fu, and A.J. Sinclair Novel pathway of metabolism of alpha-linolenic acid in the guinea pig Pediatr Res 47 3 2000 414 417
23. R. Portolesi, B.C. Powell, and R.A. Gibson Competition between 24:5n-3 and ALA for {Delta}6 desaturase may limit the accumulation of DHA in HepG2 cell membranes J Lipid Res 48 7 2007 1592 1598
24. F. Achard, C. Benistant, and M. Lagarde Interconversions and distinct metabolic fate of eicosapentaenoic, docosapentaenoic and docosahexaenoic acids in bovine aortic endothelial cells Biochim Biophys Acta 1255 3 1995 260 266
25. T. Kanayasu-Toyoda, I. Morita, and S. Murota Docosapentaenoic acid (22:5, n-3), an elongation metabolite of eicosapentaenoic acid (20:5, n-3), is a potent stimulator of endothelial cell migration on pretreatment in vitro Prostag Leukotr Essent Fatty Acids 54 5 1996 319 325
26. W. Stoffel, W. Eker, H. Assad, and H. Sprecher Enzymatic studies on the mechanism of the retroconversion of C22-polyenoic fatty acids to their C20-homologues Hoppe Seylers Z Physiol Chem 351 12 1970 1545 1554
27. E. Christensen, B. Woldseth, T.A. Hagve, B.T. Poll-The, R.J. Wanders, and H. Sprecher Peroxisomal beta-oxidation of polyunsaturated long chain fatty acids in human fibroblasts. The polyunsaturated and the saturated long chain fatty acids are retroconverted by the same acyl-CoA oxidase Scand J Clin Lab Invest Suppl 215 1993 61 74
28. J.K. Reddy, and T. Hashimoto Peroxisomal beta-oxidation and peroxisome proliferator-activated receptor alpha: an adaptive metabolic system Annu Rev Nutr 21 2001 193 230
29. Kaur G, Begg DP, Barr D, Garg M, Cameron-Smith D, Sinclair AJ. Short-term docosapentaenoic acid (22:5 n-3) supplementation increases tissue docosapentaenoic acid, DHA and EPA concentrations in rats. Br J Nutr 103(1): 32-37.
30. N. Gotoh, K. Nagao, S. Onoda, B. Shirouchi, K. Furuya, and T. Nagai Effects of three different highly purified n-3 series highly unsaturated fatty acids on lipid metabolism in C57BL/KsJ-db/db mice J Agric Food Chem 57 22 2009 11047 11054
31. R.A. Alvarez, G.D. Aguirre, G.M. Acland, and R.E. Anderson Docosapentaenoic acid is converted to docosahexaenoic acid in the retinas of normal and prcd-affected miniature poodle dogs Invest Ophthalmol Vis Sci 35 2 1994 402 408
32. P.S. Tam, R. Sawada, Y. Cui, A. Matsumoto, and Y. Fujiwara The metabolism and distribution of docosapentaenoic acid (n-6) in the liver and testis of growing rats Biosci Biotechnol Biochem 72 10 2008 2548 2554
33. P.S. Tam, R. Umeda-Sawada, T. Yaguchi, K. Akimoto, Y. Kiso, and O. Igarashi The metabolism and distribution of docosapentaenoic acid (n-6) in rats and rat hepatocytes Lipids 35 1 2000 71 75
34. F.D. Gundstone, J.L. Harwood, and F.B. Padley The lipid handbook 1994 Chapman and Hall London
35. T.A. Sanders, K. Gleason, B. Griffin, and G.J. Miller Influence of an algal triacylglycerol containing docosahexaenoic acid (22: 6n-3) and docosapentaenoic acid (22: 5n-6) on cardiovascular risk factors in healthy men and women Br J Nutr 95 3 2006 525 531
36. Y. Deng, Z.A. Almsherqi, G. Shui, M.R. Wenk, and S.D. Kohlwein Docosapentaenoic acid (DPA) is a critical determinant of cubic membrane formation in amoeba Chaos mitochondria Faseb J 23 9 2009 2866 2871
37. P. Guesnet, G. Pascal, and G. Durand Effects of dietary alpha-linolenic acid deficiency during pregnancy and lactation on lipid fatty acid composition of liver and serum in the rat Reprod Nutr Dev 28 2A 1988 275 292
38. P. Homayoun, G. Durand, G. Pascal, and J.M. Bourre Alteration in fatty acid composition of adult rat brain capillaries and choroid plexus induced by a diet deficient in n-3 fatty acids: slow recovery after substitution with a nondeficient diet J Neurochem 51 1 1988 45 48
39. S.Y. Lim, J. Hoshiba, and N. Salem Jr An extraordinary degree of structural specificity is required in neural phospholipids for optimal brain function: n-6 docosapentaenoic acid substitution for docosahexaenoic acid leads to a loss in spatial task performance J Neurochem 95 3 2005 848 857
40. S.L. Niu, D.C. Mitchell, S.Y. Lim, Z.M. Wen, H.Y. Kim, and N. Salem Jr. Reduced G protein-coupled signaling efficiency in retinal rod outer segments in response to n-3 fatty acid deficiency J Biol Chem 279 30 2004 31098 31104
41. H.Y. Kim, M. Akbar, and A. Lau Effects of docosapentaenoic acid on neuronal apoptosis Lipids 38 4 2003 453 457
42. E. Oda, K. Hatada, K. Katoh, M. Kodama, Y. Nakamura, and Y. Aizawa A case-control pilot study on n-3 polyunsaturated fatty acid as a negative risk factor for myocardial infarction Int Heart J 46 4 2005 583 591
43. T. Rissanen, S. Voutilainen, K. Nyyssonen, T.A. Lakka, and J.T. Salonen Fish oil-derived fatty acids, docosahexaenoic acid and docosapentaenoic acid, and the risk of acute coronary events: the Kuopio ischaemic heart disease risk factor study Circulation 102 22 2000 2677 2679
44. Kelly L, Grehan B, Chiesa A, O'Mara S, Downer E, Sahyoun G, et al. The polyunsaturated fatty acids, EPA and DPA exert a protective effect in the hippocampus of the aged rat. Neurobiol Aging 2010. doi:10.1016/j.neurobiolaging. 2010.04.001.
45. D. Tassoni, G. Kaur, R. Weisinger, and A. Sinclair The role of eicosanoids in the brain Asia Pac J Clin Nutr 17 S1 2008 220 228
46. P.C. Calder, and R.F. Grimble Polyunsaturated fatty acids, inflammation and immunity Eur J Clin Nutr 56 Suppl. 3 2002 S14 S19
47. M.M. Careaga, and H. Sprecher Synthesis of two hydroxy fatty acids from 7,10,13,16,19-docosapentaenoic acid by human platelets J Biol Chem 259 23 1984 14413 14417 (Pubitemid 15222258)
48. S. Akiba, T. Murata, K. Kitatani, and T. Sato Involvement of lipoxygenase pathway in docosapentaenoic acid-induced inhibition of platelet aggregation Biol Pharm Bull 23 11 2000 1293 1297
49. M. Phang, M.L. Garg, and A.J. Sinclair Inhibition of platelet aggregation by omega-3 polyunsaturated fatty acids is gender specific-redefining platelet response to fish oils Prostag Leukotr Essent Fatty Acids 81 1 2009 35 40
50. C. Benistant, F. Achard, S. Ben Slama, and M. Lagarde Docosapentaenoic acid (22:5, n-3): metabolism and effect on prostacyclin production in endothelial cells Prostag Leukotr Essent Fatty Acids 55 4 1996 287 292
51. C.N. Serhan, and N. Chiang Endogenous pro-resolving and anti-inflammatory lipid mediators: a new pharmacologic genus Br J Pharmacol 153 1:S 2007 200 215
52. C.K. Chow, Fatty acids in foods and their health implications 3rd ed. 2008 CRC Press Boca Raton
53. M. Gottlicher, E. Widmark, Q. Li, and J.A. Gustafsson Fatty acids activate a chimera of the clofibric acid-activated receptor and the glucocorticoid receptor Proc Natl Acad Sci USA 89 10 1992 4653 4657
54. C.K. Chow C.K. Chow, Fatty acids in foods and their health implications 3rd, illustrated, revised ed. 2007 Boca Raton CRC Press
55. J.D. Horton, J.L. Goldstein, and M.S. Brown SREBPs: transcriptional mediators of lipid homeostasis Cold Spring Harb Symp Quant Biol 67 2002 491 498
56. A. Pawar, and D.B. Jump Unsaturated fatty acid regulation of peroxisome proliferator-activated receptor alpha activity in rat primary hepatocytes J Biol Chem 278 38 2003 35931 35939
57. E. Kishida, M. Tajiri, and Y. Masuzawa Docosahexaenoic acid enrichment can reduce L929 cell necrosis induced by tumor necrosis factor Biochim Biophys Acta 1761 4 2006 454 462
58. D.E. Williard, S.D. Harmon, T.L. Kaduce, M. Preuss, S.A. Moore, and M.E. Robbins Docosahexaenoic acid synthesis from n-3 polyunsaturated fatty acids in differentiated rat brain astrocytes J Lipid Res 42 9 2001 1368 1376 (Pubitemid 34007666)
59. B. Langelier, J.M. Alessandri, M.H. Perruchot, P. Guesnet, and M. Lavialle Changes of the transcriptional and fatty acid profiles in response to n-3 fatty acids in SH-SY5Y neuroblastoma cells Lipids 40 7 2005 719 728