Characterization of Shrimp Oil from Pandalus borealis by High Performance Liquid Chromatography and High Resolution Mass Spectrometry
Abstract
:1. Introduction
2. Results
2.1. Lipid Classification of Shrimp Oil by HPLC-CAD
2.2. Fatty Acid Methylated Esters (FAMEs) Analysis by GC
FAME | P. borealis Shrimp Oil | P. borealis Whole Shrimp [22] | Krill Oil [23] | ||
---|---|---|---|---|---|
Intensity | RSD% (n = 4) | Original Oil | TAG Rich Fraction | ||
12:0 | 0.2% | 30.8 | 0.1% ± 0.0% | 0.2% ± 0.0% | |
13:0 | Trace | ||||
14:0 | 3.6% | 19.1 | 2.3% | 1.1% ± 0.0% | 17.5% ± 0.2% |
15:0 | 0.3% | 15.9 | 0.4% ± 0.0% | 0.4% ± 0.0% | |
16:0 | 12.5% | 2.1 | 14.9% | 24.0% ± 0.1% | 18.9% ± 0.2% |
17:0 | 0.2% | 32.9 | 0.2% ± 0.0% | 0.2% ± 0.0% | |
18:0 | 2.9% | 17.5 | 2.9% | 1.0% ± 0.0% | 0.8% ± 0.0% |
20:0 | Trace | 0.1% ± 0.0% | 0.1% ± 0.0% | ||
22:0 | Trace | ||||
14:1n5 | 0.2% | 17.3 | |||
16:1n5 | 0.4% | 22.5 | |||
16:1n7 | 12.5% | 13.2 | 14.5% | 5.5% ± 0.0% | 9.2% ± 0.2% |
17:1n7 | Trace | ||||
18:1n5 | 0.7% | 15.0 | |||
18:1n7 | 4.3% | 10.8 | 7.7% | 6.6% ± 0.1% | 6.3% ± 0.1% |
18:1n9 | 12.9% | 7.3 | 12.3% | 10.0% ± 0.0% | 10.9% ± 0.1% |
20:1n7 | 1.7% | 49.3 | 0.2% ± 0.0% | 0.2% ± 0.0% | |
20:1n9 | 6.3% | 36.7 | 2.7% | 0.6% ± 0.0% | 0.5% ± 0.0% |
20:1n11 | 0.8% | - | |||
22:1n7 | 2.4% | 56.2 | |||
22:1n9 | 7.7% | 39.0 | 1.3% | 0.6% ± 0.0% | 0.3% ± 0.0% |
24:1n9 | Trace | 0.1% ± 0.0% | |||
16:2n4 | 0.5% | 53.3 | 0.5% ± 0.0% | 1.1% ± 0.0% | |
16:2n6 | 0.3% | 81.5 | |||
16:3n3 | 0.2% | 16.7 | 0.1% ± 0.0% | 2.5% ± 0.0% | |
16:3n4 | 0.4% | 37.1 | |||
16:4n1 | 0.3% | 4.9 | |||
16:4n3 | Trace | 0.8% ± 0.0% | |||
18:2n4 | 0.4% | 28.3 | |||
18:2n6 | 0.8% | 8.4 | 0.6% | 1.7% ± 0.0% | 1.7% ± 0.0% |
18:3n3 | 0.6% | 44.0 | Trace | 1.3% ± 0.0% | 1.4% ± 0.0% |
18:3n4 | 0.7% | - | |||
18:3n6 | Trace | 0.2% ± 0.0% | 0.3% ± 0.0% | ||
18:4n1 | Trace | ||||
18:4n3 | 1.1% | 8.2 | 0.5% | 3.8% ± 0.1% | 6.8% ± 0.1% |
20:2n6 | 0.3% | 38.8 | |||
20:2n9 | Trace | ||||
20:3n3 | 0.2% | 73.5 | |||
20:3n6 | Trace | 0.0% ± 0.0% | |||
20:4n3 | 2.4% | - | Trace | 0.4% ± 0.0% | 0.3% ± 0.0% |
20:4n6 | 0.4% | 34.2 | 0.4% ± 0.0% | 0.3% ± 0.0% | |
20:5n3 | 10.4% | 11.3 | 12.5% | 18.5% ± 0.2% | 9.7% ± 0.0% |
21:5n3 | 0.3% | 23.0 | 0.6% ± 0.0% | 0.3% ± 0.0% | |
22:2 | Trace | ||||
22:4n6 | Trace | ||||
22:5n3 | 0.5% | 7.2 | 1.0% | 0.4% ± 0.0% | 0.2% ± 0.0% |
22:5n6 | Trace | 0.0% ± 0.0% | |||
22:6n3 | 9.5% | 7.1 | 7.7% | 9.0% ± 0.0% | 3.8% ± 0.0% |
Total | 98.8% | 0.00 | |||
Saturated (SFAs) | 19.7% | 3.4 | 21.4% | 38.1% ± 0.0% | 43.4% ± 0.0% |
Monounsaturated (MUFAs) | 49.9% | 8.8 | 46.0% | 24.0% ± 0.2% | 27.9% ± 0.1% |
Polyunsaturated (PUFAs) | 29.2% | 16.1 | 25.3% | 37.9% ± 0.2% | 28.8% ± 0.1% |
Omega-3 | 25.2% | 18.9 | 21.7% | 35.0% ± 0.2% | 25.2% ± 0.1% |
Omega-6 | 1.7% | 17.7 | 0.6% | 2.3% ± 0.0% | 2.3% ± 0.0% |
2.3. Characterization of TAGs in Shrimp Oil
2.3.1. Identification of TAGs Species by LC-HRMS
No. | Molecular Formula | RT (min) | Calculated m/z [M + NH4]+ | Observed [M + NH4]+ | C:DB | Intensity (%) | TAG Identity | |
---|---|---|---|---|---|---|---|---|
Major Composition | Other Composition | |||||||
1 | C49H90O6 | 27.79 | 792.7076 | 792.7081 | TAG(46:2) | 1.4 | TAG(14:0/16:1/16:1) | TAG(12:0/16:1/18:1) |
2 | C49H92O6 | 28.70 | 794.7232 | 794.7256 | TAG(46:1) | 3.2 | TAG(14:0/16:0/16:1) | TAG(14:0/14:0/18:1), TAG(12:0/16:0/18:1) |
3 | C51H92O6 | 28.31 | 818.7232 | 818.7220 | TAG(48:3) | 2.5 | TAG(16:1/16:1/16:1) | TAG(14:1/16:1/18:1) |
4 | C51H94O6 | 29.13 | 820.7389 | 820.7413 | TAG(48:2) | 6.4 | TAG(16:0/16:1/16:1) | TAG(14:0/16:1/18:1) |
5 | C51H96O6 | 29.90 | 822.7545 | 822.7618 | TAG(48:1) | 1.3 | TAG(16:0/16:0/16:1) | TAG(14:0/16:0/18:1) |
6 | C53H90O6 | 27.40 | 840.7053 | 840.7105 | TAG(50:6) | 1.4 | TAG(14:0/16:1/20:5) | |
7 | C53H96O6 | 29.54 | 846.7545 | 846.7565 | TAG(50:3) | 2.9 | TAG(16:1/16:1/18:1) | TAG(14:1/18:1/18:1), TAG(14:1/16:1/20:1) |
8 | C53H98O6 | 30.29 | 848.7702 | 848.7761 | TAG(50:2) | 1.6 | TAG(16:0/16:1/18:1) | TAG(14:0/16:1/20:1), TAG(14:0/18:1/18:1), TAG(16:1/16:1/18:0) |
9 | C53H100O6 | 31.11 | 850.7858 | 850.7929 | TAG(50:1) | 2.3 | TAG(16:0/16:0/18:1) | TAG(14:0/16:0/20:1) |
10 | C55H92O6 | 27.89 | 866.7232 | 866.7246 | TAG(52:7) | 2.4 | TAG(16:1/16:1/20:5) | |
11 | C55H94O6 | 28.70 | 868.7389 | 868.7418 | TAG(52:6) | 2.7 | TAG(16:0/16:1/20:5) | TAG(14:0/18:1/20:5) |
12 | C55H96O6 | 29.62 | 870.7545 | 870.7586 | TAG(52:5) | 3.0 | TAG(16:0/16:0/20:5) | TAG(14:0/18:0/20:5) |
13 | C55H100O6 | 30.75 | 874.7858 | 874.7930 | TAG(52:3) | 3.4 | TAG(16:1/18:1/18:1), TAG(16:1/16:1/20:1) | TAG(14:1/18:1/20:1), TAG(14:1/16:1/22:1) |
14 | C55H102O6 | 31.44 | 876.8015 | 876.8102 | TAG(52:2) | 1.4 | TAG(16:0/16:1/20:1), TAG(16:0/18:1/18:1) | TAG(14:0/18:1/20:1), TAG(14:0/16:1/22:1), TAG(16:1/18:0/18:1) |
15 | C55H104O6 | 32.24 | 878.8171 | 878.8104 | TAG(52:1) | 1.3 | TAG(16:0/18:0/18:1) | TAG(14:0/16:0/22:1), TAG(14:0/18:0/20:1), TAG(16:0/16:0/20:1) |
16 | C57H90O6 | 26.97 | 888.7076 | 888.7070 | TAG(54:10) | 0.6 | TAG(14:0/20:5/20:5) | |
17 | C57H96O6 | 29.22 | 894.7545 | 894.7576 | TAG(54:7) | 2.8 | TAG(16:1/18:1/20:5) | TAG(16:0/16:1/22:6), TAG(14:0/18:1/22:6) |
18 | C57H98O6 | 30.00 | 896.7702 | 896.7792 | TAG(54:6) | 4.5 | TAG(16:0/18:1/20:5) | TAG(14:0/20:1/20:5) |
19 | C57H104O6 | 31.88 | 902.8171 | 902.8209 | TAG(54:3) | 2.6 | TAG(16:1/18:1/20:1), TAG(18:1/18:1/18:1) | TAG(16:1/16:1/22:1), TAG(14:1/20:1/20:1), TAG(14:1/18:1/22:1) |
20 | C57H106O6 | 32.57 | 904.8328 | 904.8364 | TAG(54:2) | 2.3 | TAG(16:0/18:1/20:1) | TAG(14:0/20:1/20:1), TAG(16:0/16:1/22:1), TAG(14:0/18:1/22:1), TAG(16:1/18:0/20:1), TAG(18:0/18:1/18:1) |
21 | C59H92O6 | 27.41 | 914.7232 | 914.7269 | TAG(56:11) | 1.6 | TAG(16:1/20:5/20:5) | TAG(16:1/18:4/22:6) |
22 | C59H98O6 | 29.75 | 920.7702 | 920.7770 | TAG(56:8) | 2.2 | TAG(16:1/18:1/22:6) | |
23 | C59H100O6 | 30.37 | 922.7858 | 922.7889 | TAG(56:7) | 2.3 | TAG(18:1/18:1/20:5) | TAG(16:0/18:1/22:6), TAG(16:1/20:1/20:5) |
24 | C59H102O6 | 31.22 | 924.8015 | 924.8085 | TAG(56:6) | 3.5 | TAG(16:0/20:1/20:5) | TAG(18:0/18:1/20:5), TAG(18:1/18:4/20:1) |
25 | C59H108O6 | 32.93 | 930.8484 | 930.8499 | TAG(56:3) | 2.5 | TAG(16:1/18:1/22:1), TAG(16:1/20:1/20:1), TAG(18:1/18:1/20:1) | TAG(14:1/20:1/22:1), TAG(14:1/18:1/24:1) |
26 | C59H110O6 | 33.59 | 932.8641 | 932.8682 | TAG(56:2) | 2.6 | TAG(16:0/18:1/22:1), TAG(16:0/20:1/20:1) | TAG(14:0/20:1/22:1), TAG(16:1/18:0/22:1), TAG(18:0/18:1/20:1) |
27 | C61H94O6 | 28.06 | 940.7389 | 940.7376 | TAG(58:12) | 1.0 | TAG(16:1/20:5/22:6) | |
28 | C61H96O6 | 28.96 | 942.7545 | 942.7576 | TAG(58:11) | 1.7 | TAG(16:0/20:5/22:6) | |
29 | C61H102O6 | 30.99 | 948.8015 | 948.8088 | TAG(58:8) | 3.3 | TAG(18:1/18:1/22:6) | TAG(16:1/20:1/22:6) |
30 | C61H104O6 | 31.53 | 950.8171 | 950.8204 | TAG(58:7) | 1.9 | TAG(16:1/20:5/22:1) | TAG(18:1/20:1/20:5) |
31 | C61H106O6 | 32.30 | 952.8328 | 952.8352 | TAG(58:6) | 2.4 | TAG(16:0/20:5/22:1) | TAG(18:0/20:1/20:5) |
32 | C61H114O6 | 34.57 | 960.8954 | 960.8954 | TAG(58:2) | 2.6 | TAG(16:0/20:1/22:1) | TAG(14:0/20:1/24:1), TAG(14:0/22:1/22:1), TAG(16:0/18:1/24:1), TAG(18:0/18:1/22:1), TAG(18:0/20:1/20:1) |
33 | C63H98O6 | 29.30 | 968.7702 | 968.7745 | TAG(60:12) | 0.9 | TAG(18:1/20:5/22:6) | |
34 | C63H106O6 | 32.11 | 976.8328 | 976.8328 | TAG(60:8) | 2.9 | TAG(16:1/22:1/22:6),TAG(18:1/20:1/22:6) | |
35 | C63H108O6 | 32.66 | 978.8484 | 978.8484 | TAG(60:7) | 2.8 | TAG(18:1/20:5/22:1) | TAG(20:1/20:1/20:5) |
36 | C63H110O6 | 33.40 | 980.8641 | 980.8679 | TAG(60:6) | 0.7 | TAG(18:0/20:5/22:1) | |
37 | C63H116O6 | 34.85 | 986.9110 | 986.9110 | TAG(60:3) | 1.9 | TAG(16:1/22:1/22:1), TAG(18:1/20:1/22:1) | TAG(16:1/20:1/24:1), TAG(18:1/18:1/24:1), |
38 | C63H118O6 | 35.47 | 988.9267 | 988.9183 | TAG(60:2) | 1.4 | TAG(16:0/22:1/22:1) | TAG(16:0/20:1/24:1), TAG(14:0/22:1/24:1), TAG(18:0/20:1/22:1) |
39 | C65H110O6 | 33.13 | 1004.8641 | 1004.8661 | TAG(62:8) | 2.4 | TAG(18:1/22:1/22:6), TAG(20:1/20:1/22:6) | |
40 | C65H112O6 | 33.63 | 1006.8797 | 1006.8805 | TAG(62:7) | 1.0 | TAG(20:1/20:5/22:1) | TAG(18:1/20:5/24:1) |
41 | C65H120O6 | 35.74 | 1014.9423 | 1014.9392 | TAG(62:3) | 2.3 | TAG(18:1/22:1/22:1), TAG(20:1/20:1/22:1) | TAG(16:1/22:1/24:1), TAG(18:1/20:1/24:1) |
42 | C67H114O6 | 34.06 | 1032.8954 | 1032.8907 | TAG(64:8) | 1.3 | TAG(20:1/22:1/22:6) | |
43 | C67H124O6 | 36.62 | 1042.9736 | 1042.9720 | TAG(64:3) | 2.3 | TAG(20:1/20:1/24:1) | TAG(18:1/22:1/24:1), TAG(20:1/22:1/22:1) |
44 | C69H118O6 | 35.01 | 1060.9267 | 1060.9216 | TAG(66:8) | 1.3 | TAG(22:1/22:1/22:6) | |
45 | C69H128O6 | 37.41 | 1071.0049 | 1071.0076 | TAG(66:3) | 1.5 | TAG(22:1/22:1/22:1) | TAG(20:1/22:1/24:1) |
Source | Molar (%) | sn-1,3 | sn-2 | Total |
---|---|---|---|---|
P. borealis Shrimp oil | SFAs + MUFAs | 56.8 | 19.2 | 75.9 |
20:5n3 (EPA) | 4.1 | 4.5 | 9.0 | |
22:6n3 (DHA) | 1.2 | 7.1 | 8.3 | |
Omega-3 | 17.8 | |||
Omega-6 | 2.8 | |||
Cod liver oil [27] | EPA | 2.1 | 6.4 | 8.5 |
DHA | 0.4 | 9.2 | 9.6 | |
Tuna oil [28] | EPA | 6.7 | ||
DHA | 11.5 | |||
Algae oil [28] | DHA | 35.2 | ||
Anchovy/sardine fish oil [25] | EPA | 80.9 | 19.1 | |
DHA | 38.3 | 61.7 |
2.3.2. Regioisomeric Distributions of Fatty Acids on TAGs Determined by 13C-NMR
2.4. Characterization of Astaxanthin and Its Esters in Shrimp Oil
2.4.1. Identification of Astaxanthin and Its Esters by LC-HRMS
3. Discussion
3.1. Lipid Classes and FA Profiles of Shrimp Oil
Compounds | Molecular Formula | RT (min) | Intensity (%) | Observed m/z on MS/MS | Identification by Other Reports | ||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
[M + H]+ | [M-FA1 + H]+ | [M-FA2 + H]+ | Ax Backbone Related MS/MS | P. borealis [31] | L. vannamei [32] | Krill [33] | Microalgae [31] | ||||||
Free Ax | |||||||||||||
1 | Astaxanthin | C40H52O4 | 2.10 | 0.5 | 597.3663 | 579.3843 | 561.4108 | ||||||
2 | Astaxanthin isomer1 | C40H52O4 | 3.56 | 0.5 | 597.3266 | 579.3949 | 561.3801 | ||||||
3 | Astaxanthin isomer2 | C40H52O4 | 3.85 | 0.4 | 597.3575 | 579.3616 | 561.3696 | ||||||
Ax-FA Monoesters | |||||||||||||
4 | Ax-C12:0 | C52H74O5 | 15.87 | 7.3 | 779.5643 | 579.3883 | 561.3945 | ✓ | ✓ | ||||
5 | Ax-C20:5 | C60H80O5 | 17.78 | 5.1 | 881.6111 | 579.3793 | 561.3813 | ✓ | |||||
6 | Ax-C14:0 | C54H78O5 | 17.80 | 1.3 | 807.6991 | 579.4027 | 561.4552 | ✓ | ✓ | ||||
7 | Ax-C22:6 | C62H82O5 | 18.56 | 2.3 | 907.7129 | 579.4470 | 561.4552 | ✓ | |||||
8 | Ax-C16:1 | C56H80O5 | 18.41 | 2.3 | 833.6066 | 579.3861 | 561.3824 | ✓ | |||||
9 | Ax-C16:0 | C56H82O5 | 19.63 | 2.4 | 835.7094 | 579.4558 | 561.4291 | ✓ | ✓ | ✓ | ✓ | ||
10 | Ax-C18:1 | C58H84O5 | 20.18 | 3.9 | 861.6601 | 579.3837 | 561.3689 | ✓ | ✓ | ✓ | ✓ | ||
11 | Ax-C18:0 | C58H86O5 | 21.39 | 0.9 | 863.6774 | 579.4111 | 561.3632 | ✓ | ✓ | ✓ | |||
12 | Ax-C20:1 | C60H88O5 | 21.82 | 2.0 | 889.7763 | 579.4647 | 561.4116 | ✓ | |||||
Ax-FA Diesters | |||||||||||||
13 | Ax-C12:0/20:5 | C72H102O6 | 26.47 | 4.9 | 1063.8861 | 863.6884 | 761.6426 | 579.447 | 561.4377 | ✓ | |||
14 | Ax-C12:0/22:6 | C74H104O6 | 26.99 | 2.6 | 1089.8059 | 889.5828 | 761.5556 | 579.384 | 561.3867 | ✓ | |||
15 | Ax-C20:5/20:5 | C80H108O6 | 27.51 | 1.3 | 1165.8419 | 863.5995 | 863.5995 | 579.3549 | 561.3832 | ✓ | |||
16 | Ax-C12:0/16:0 | C68H104O6 | 27.78 | 5.8 | 1017.8812 | 817.6915 | 761.6426 | 579.4558 | 561.4291 | ✓ | ✓ | ||
17 | Ax-C14:0/14:0 | 789.6770 | 789.6770 | ✓ | |||||||||
18 | Ax-C20:5/22:6 | C82H110O6 | 28.02 | 1.1 | 1191.8425 | 889.6176 | 863.5938 | 579.3936 | 561.3767 | ✓ | |||
19 | Ax-C16:1/20:5 | C76H108O6 | 28.04 | 2.2 | 1117.8411 | 863.5801 | 815.6221 | 579.3740 | 561.3672 | ||||
20 | Ax-C12:0/18:1 | C70H106O6 | 28.12 | 12.6 | 1043.8131 | 843.6299 | 761.5554 | 579.3832 | 561.3793 | ✓ | ✓ | ||
21 | Ax-C14:0/16:1 | 815.6266 | 789.5727 | ✓ | |||||||||
22 | Ax-C16:0/20:5 | C76H110O6 | 28.76 | 2.3 | 1119.8601 | 863.6044 | 817.5956 | 579.3857 | 561.3710 | ✓ | |||
23 | Ax-C18:1/20:5 | C78H112O6 | 29.13 | 5.5 | 1145.8514 | 863.5996 | 843.6376 | 579.3837 | 561.3719 | ✓ | ✓ | ||
24 | Ax-C16:0/22:6 | 889.5994 | 817.6177 | ✓ | |||||||||
25 | Ax-C12:0/20:1 | C72H110O6 | 29.23 | 7.3 | 1071.8407 | 871.6646 | 761.5882 | 579.3846 | 561.3730 | ✓ | ✓ | ||
26 | Ax-C14:0/18:1 | 843.6436 | 789.5870 | ✓ | |||||||||
27 | Ax-C16:1/18:1 | C74H112O6 | 29.56 | 4.4 | 1097.9844 | 843.7114 | 815.6818 | 579.4558 | 561.4291 | ✓ | |||
28 | Ax-C18:1/22:6 | C80H114O6 | 29.78 | 2.0 | 1171.8672 | 889.6319 | 843.6218 | 579.3994 | 561.3832 | ✓ | ✓ | ||
29 | Ax-C20:1/20:5 | C80H116O6 | 30.17 | 1.3 | 1173.8394 | 863.6236 | 871.6613 | 579.3936 | 561.3782 | ||||
30 | Ax-C16:0/18:1 | C74H114O6 | 30.26 | 6.3 | 1099.8682 | 843.6331 | 817.6174 | 579.3845 | 561.3745 | ✓ | ✓ | ||
31 | Ax-C14:0/20:1 | 871.6799 | 789.6058 | ||||||||||
32 | Ax-C18:1/18:1 | C76H116O6 | 30.57 | 5.4 | 1125.9897 | 843.7221 | 843.7221 | 579.4470 | 561.4377 | ✓ | ✓ | ✓ | |
33 | Ax-C16:1/20:1 | 871.7469 | 815.7239 | ||||||||||
34 | Ax-C16:0/20:1 | C76H118O6 | 31.25 | 2.0 | 1127.9919 | 871.7578 | 817.7126 | 579.4558 | 561.4203 | ||||
35 | Ax-C18:0/18:1 | 843.7327 | 845.7125 | ✓ | |||||||||
36 | Ax-C18:1/20:1 | C78H120O6 | 31.55 | 2.8 | 1153.9973 | 871.7469 | 843.7006 | 579.4558 | 561.4465 | ✓ | |||
37 | Ax-C20:1/20:1 | C80H124O6 | 32.49 | 1.3 | 1181.9945 | 871.7469 | 871.7469 | 579.4558 | 561.4291 | ||||
38 | Ax- C18:1/22:1 | 843.7114 | 899.8098 |
Sources | Phospholipids | Triacylglycerols | Other Polar Lipids |
---|---|---|---|
P. borealis shrimp oil | >90% | ||
P. borealis shrimp larvae [12,13] | ~80% | 5%–15% | |
Krill oil [11] | 20%–33% | 1%–3% | 64%–77% |
Krill oil [35] | 93.1% | 1.7% | 5.4% |
Krill oil [35] | 51.3% | 33.4% | 15.2% |
3.2. Characterization and Structural Elucidation of TAGs in Shrimp Oil
3.3. Characterization and Identification of Astaxanthin Species of Shrimp Oil
4. Materials and Methods
4.1. Materials
4.2. High Performance Liquid Chromatography (HPLC)
4.3. FAME Preparation
4.4. Gas Chromatography (GC)
4.5. LC-MS Instrumentation
4.6. 13C-NMR Spectroscopy
5. Conclusions
Supplementary Files
Supplementary File 1Acknowledgments
Author Contributions
Conflicts of Interest
References
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Jiao, G.; Hui, J.P.M.; Burton, I.W.; Thibault, M.-H.; Pelletier, C.; Boudreau, J.; Tchoukanova, N.; Subramanian, B.; Djaoued, Y.; Ewart, S.; et al. Characterization of Shrimp Oil from Pandalus borealis by High Performance Liquid Chromatography and High Resolution Mass Spectrometry. Mar. Drugs 2015, 13, 3849-3876. https://doi.org/10.3390/md13063849
Jiao G, Hui JPM, Burton IW, Thibault M-H, Pelletier C, Boudreau J, Tchoukanova N, Subramanian B, Djaoued Y, Ewart S, et al. Characterization of Shrimp Oil from Pandalus borealis by High Performance Liquid Chromatography and High Resolution Mass Spectrometry. Marine Drugs. 2015; 13(6):3849-3876. https://doi.org/10.3390/md13063849
Chicago/Turabian StyleJiao, Guangling, Joseph P. M. Hui, Ian W. Burton, Marie-Hélène Thibault, Claude Pelletier, Josée Boudreau, Nadia Tchoukanova, Balaji Subramanian, Yahia Djaoued, Stephen Ewart, and et al. 2015. "Characterization of Shrimp Oil from Pandalus borealis by High Performance Liquid Chromatography and High Resolution Mass Spectrometry" Marine Drugs 13, no. 6: 3849-3876. https://doi.org/10.3390/md13063849