The table below gives the
stereospecific distribution of fatty acids in triacylglycerols of depot fats in
man and some animals.
|
sn |
14:0 |
16:0 |
16:1 |
18:0 |
18:1 |
18:2 |
20:1 |
22:1 |
20:5 |
22:5 |
22:6 |
|
|
|
1 |
4 |
39 |
5 |
10 |
33 |
3 |
|||||
|
|
1 |
2 |
32 |
5 |
9 |
32 |
15 |
|||||
|
|
1 |
2 |
16 |
3 |
21 |
44 |
12 |
|||||
|
|
1 |
2 |
25 |
12 |
6 |
33 |
14 |
|||||
|
|
1 |
6 |
12 |
13 |
1 |
16 |
3 |
25 |
14 |
3 |
1 |
1 |
|
|
1 |
6 |
15 |
14 |
6 |
28 |
2 |
12 |
6 |
2 |
1 |
1 |
|
Menhaden |
1 2 3 |
12 10.5 5 |
24 20 7 |
18 10.5 9 |
1 2 4 |
13 7.5 13;5 |
1 0.5 3 |
1 0.5 2 |
3 17.5 16 |
1 3 2 |
4 17 6 |
|
|
Seal Blubber |
1 2 3 |
2 8 0 |
3 12 3 |
8 35 12 |
1 2 1 |
38 23 18 |
0 1 2 |
13 4 17 |
3 0 3 |
8 2 11 |
4 1 8 |
10 2 18 |
|
|
1 |
4 |
11 |
15 |
1 |
29 |
1 |
18 |
8 |
3 |
2 |
3 |
Seal blubber and menhaden : data from Wanasundara U et al., J Food Lipids 1997, 4, 51
It can be seen that, as in vegetal
oils, the external positions are generally occupied by saturated fatty acids,
except in pig where palmitic acid is more abundant at the 2 position. Monoenes
are differently distributed, oleic acid being more abundant at positions 2 and 3
in man, at positions 1 and 3 in pig and 2 in chicken. The distribution of 18:2
is also species specific. It must be noticed that fat depots in marine animals
are rich in polyunsaturated fatty acids and long-chain monoenes. Results
indicate that the stereospecific location of the polyunsaturated fatty acids is
in the position 2 (also 3 for 20:5n-3 in cod) in fish but in position 3 for
mammals (same in seal, whale and polar bear) or in positions 1 and 3 (seal
blubber). This raises the question of the
availability of these fatty acids from food expecting a benefic effect on
diverse human functions.
Oils from fish and marine mammals are characterized by a large range of fatty
acids from 12 to 26 carbon atoms and 0 to 6 double bonds. The bulk of the fatty
chains is contributed by saturated (15-25%), monoenes (35-60%) and polyenes
(25-40%). Among polyunsaturated, 20:5n-3 and 22:6n-3 are the most prevalent. The
study of the structure of the triacylglycerol molecules of marine oils is
complex because of their multiplicity and the low and differential hydrolysis by
lipases of positions occupied by 20:5 or 22:6n-3, the use of the Grignard
reagent being required.
From the above data obtained by chemical degradation as well as those obtained
with nuclear magnetic resonance spectroscopy (Aursand M et al., JAOCS 1995,
72, 293), it may be inferred that fish and mammal oils have distinct
positional distributions of
w3
fatty acids. As an example, in Salmon, cod or herring, 22:5 and DHA are
concentrated in the
b-position
(sn-2), while, in mammals, they are mainly found in the
a-position
(sn-1,3). This may be important in considering the bioavailability of these
important fatty acids after ingestion of marine foods from various origins.