1. SEAL BLUBBER OIL, SPECIALTY LIPIDS AND OMEGA-3 FATTY ACIDS Department of Biochemistry Memorial University of Newfoundland St. John’s, NL, A1B 3X9, Canada

3. MI and Dietary Fat Intake of Eskimos versus Danes Eskimos Danes Eskimos Danes Myocardial Infarction 3 40 Energy from fat (%) 39 42 n-6 PUFA (g/d) 5 10 n-3 PUFA (g/d) 14 3 n-3/n-6 2.8 0.3 Cholesterol (mg/d) 790 420

4. Coronary Heart Disease (CHD) There are 3 stages in the development of CHD: Injury to the coronary artery wall; Injury to the coronary artery wall; Build up of a fatty a fibrous plaque Build up of a fatty a fibrous plaque (atherosclerosis); (atherosclerosis); Formation of a blood clot (thrombosis); Formation of a blood clot (thrombosis); If a clot forms in an artery which is already narrowed by atherosclerosis, a heart attack can occur If a clot forms in an artery which is already narrowed by atherosclerosis, a heart attack can occur

5. Omega-3 fatty acids may have positive effects on: High blood pressure High blood pressure Body TAG and cholesterol Body TAG and cholesterol Abnormal blood clotting (thrombosis) Abnormal blood clotting (thrombosis) Fat deposition (atherosclerosis) Fat deposition (atherosclerosis) Cardiovascular diseases Cardiovascular diseases

6. Other Effects of Marine Oils Relieve arthritis Relieve arthritis Improve diabetic condition Improve diabetic condition Enhance body immunity Enhance body immunity Thinning of blood Thinning of blood Diarrhea and nausea in certain conditions Diarrhea and nausea in certain conditions

7. Breast Feeding and Intellectual Performance Weschler Intelligence Group I Group II scale for children No mother’s Mother’s milk Δ 1 milk Verbal scale 92 102 8.9* Performance scale 93 102 8.1* Overall IQ 93 103 8.3* * p<0.0001 Reference: Lucas et al. 1992

8. EPA (C20:5) DHA (C22:6) DPA (C22:5)

9. CH 2 O C O Sn-1 HO CH CH 2 O C O Sn-3 R 1 R 3 Sn-2 CH 2 O C O C O CH CH 2 O C O Sn-3 Sn-1 O R 1 R 3 R 2

10. Fatty Acid Composition of Seal Blubber, Menhaden and Algal Oils Fatty acid Seal Blubber a Menhaden Algal 10:0 - -1.2 12:0 - -6.0 14:0 3.4(4.3)8.3 16.8 14:1 1.0(1.2)0.4 - 16:0 5.0(7.9) 17.1 14.0 16:1n-7 15.1(22.0) 11.41.5 18:1n-9 & n-11 26.4(22.4) 12.1 14.7 18:2 n-6 1.3(1.6)1.40.5 20:1 n-9 15.0(8.8)1.4- 20:5 n-3 5.4(9.7) 13.20.1 22:1 n-11 3.6(1.7)0.1- 22:5 n-3 4.9(5.8)2.4- 22:6 n-3 7.9(9.9) 10.1 43.5 a Values in parentheses are for ringed seal blubber oil

12. 1 2 3 2 + FFAs A Pancreatic lipase B CH 3 Mg Br 1 2 OH 2 3 Tertiary alcoholMAGs + + + + 1 HO 3 c 1 2 P P 2 3 + D Dichlorophenylphosphate + H 2 O Phospholipase A 2 1 HO P P 2 3 + + FFAs Pancreatic lipase P 2 OH + FFAs F G E H TAGs STEREOSPECIFIC ANALYSES

13. Instability of Omega-3 Oils Oxidation results in: - Loss of EPA% and DHA% - Off fishy odor and/or taste Prone to oxidation primary secondary EPA/DHA peroxides aldehydes ketones, etc Indicators: Peroxide p-Anisidine Value Value Oxidation results in: - Loss of EPA% and DHA% - Off fishy odor and/or taste

14. Stability and Stabilization of Edible Oils Stability of edible oils depends on: Stability of edible oils depends on: Degree of unsaturation Degree of unsaturation Position in the triacylglycerol molecule Position in the triacylglycerol molecule Minor components Minor components Process/ storage conditions Process/ storage conditions

15. C O OH R2R2 R1R1 H C O R2R2 R1R1 H + OH C H R1R1 O + R 2 + RH C R1R1 O + ROH R2R2 C OH R2R2 R1R1 H + R Lipid hydroperoxide Alkoxy radical Hydroxyl radical Aldehyde Alcohol Ketone Alcohol RH RO R C R1R1 O R2R2

16. DOUBLE BOND INDEX (DBI) DBI = 1 x (% monoenes / 100) + 2 x (% dienes / 100) + 3 x (% trienes / 100) + ……… etc. DBI = mean number of double bonds per fatty acid

17. METHYLENE BRIDGE INDEX (MBI) MBI = mean number of bis-allylic methylene bridge positions per fatty acid MBI = 1 x (% dienes / 100) + 2 x (% trienes / 100) + … etc.

18. Fatty acid a BO b Modified BO EPOModified EPO 16:0 18:0 18:1 18:2  6 18:3  6 20:1 20:5  3 22:1 22:6  3 9.8 (0.1) 3.1 (0.3) 15.2 (0.7) 38.4 (0.9) 24.4 (0.9) 4.1 (0.3) ND c 2.5 (0.1) ND c 5.1 (0.4) 2.1 (0.1) 10.7 (0.1) 22.5 (0.3) 17.4 (0.2) 2.6 (0.1) 25.9 (0.5) 1.7 (0.3) 9.6 (0.8) 6.2 (0.1) 1.7 (0.1) 8.7 (0.6) 73.6 (0.9) 9.1 (0.4) ND c 3.4 (0.1) 1.0 (0.1) 6.1 (0.1) 45.9 (0.2) 7.6 (0.1) 0.2 (0.1) 25.7 (0.6) ND c 7.9 (0.1) Fatty acid profile of borage (BO) and evening primrose oils (EPO) before and after enzymatic modification by Pseudomonas sp. a w/w%; b Mean (SD); c Not detected  3/  6 ratio DBI MBI 0.90 2.99 2.09 0.63 2.97 2.03 - 1.72 0.87 - 1.83 0.92

20. Tocopherols (mg/kg) BO a Modified BOEPOModified EPO    Total - 116 (0.8) 1116 (1.5) 1232 - - 483 (0.9) 483 112 (0.7) 202 (0.2) 56 (0.9) 370 99 (0.1) 122 (0.2) 52 (0.8) 273 Tocopherol content of borage (BO) and evening primrose oils (EPO) before and after enzymatic modification a Mean (SD)