Marine lipids
Glycolipid fatty acids
Glycosphingolipids (GSLs) are ubiquitous membrane constituents in
animals, which play fundamental roles in major phenomena such as
cell-cell recognition and antigenic specificity. GSLs from marine sponges
possess interesting immunostimulatory and antitumor activities (Natori
et al., 1994; Li et al., 1995; Costantino et al., 1996). The three moieties
of a GSL (sugar head moiety, long-chain aminoalcohol attached by
O-ester linkage to the primary alcohol, and fatty acid attached to the
amino group) yielded three fractions on acid methanolysis, including
a fatty acid methyl ester mixture.
Glycolipids, contrary to phospholipids, generally contained mainly
short-chain acids, especially saturated ones, and isoprenoid acids
occurred at low levels or not at all. These GSLs were devoid of 2-hydroxy
farty acids, in contrast with the other sponges investigated.
The table below summarizes the fatty acid composition of individual
GSLs isolated by chromatographic methods. A few, mainly saturated,
compounds were generally detected. Of interest was the first observed
occurrence of a Δ5,9 fatty acid in a glycolipid and of Δ5 and Δ6 unsaturated acids.
Fatty acid composition of some individual sponge glycosphingolipids.
Polymastia mamillaris (Britanny) (%)
Glycolipid A: 14:0(12.1), 18:1 (11.5), 18:0 (24.8) and 20:0 (tr.)
Glycolipid B: 14:0(10.0), 16:0 (20.6), 9-18:1 (1.5),11-18:1 (3.1),
18:0 (4.3), 20:0 (6.0), 21:0 (24.6) and 24:0 (2.2)
Dysedea sp. (Arabian gulf, Qatar) (%)
Glycolipid A: 12:0, 14:0, 6-15:1, 9-15:1, 15:0, 6-16:1, 16:0, 6-17:1,17:0,
18:2, 11-18:1, 5,9-24:2 and 17-24:1
Glycolipid B: 12:0, 14:0 <10.0), i-15:0, 15:0,5-16:1, 16:0 (44.0), i-17:0,
17:0, 5-18:1, 18:0(11.2), 19:0, 20:0, 21:0 and traces of
22:0, 23:0, 24:0, 25:0 and 26:0
New branched-chain unsaturated fatty acids and polyunsaturated fatty
acid content in gorgonians
The most interesting result was the occurrence in Leptogorgiapiccola of three
new fatty acids presented and identified as pyrrolidides (Mirallès et al.,
40
Glycolipid fatty acids
Glycosphingolipids (GSLs) are ubiquitous membrane constituents in
animals, which play fundamental roles in major phenomena such as
cell-cell recognition and antigenic specificity. GSLs from marine sponges
possess interesting immunostimulatory and antitumor activities (Natori
et al., 1994; Li et al., 1995; Costantino et al., 1996). The three moieties
of a GSL (sugar head moiety, long-chain aminoalcohol attached by
O-ester linkage to the primary alcohol, and fatty acid attached to the
amino group) yielded three fractions on acid methanolysis, including
a fatty acid methyl ester mixture.
Glycolipids, contrary to phospholipids, generally contained mainly
short-chain acids, especially saturated ones, and isoprenoid acids
occurred at low levels or not at all. These GSLs were devoid of 2-hydroxy
farty acids, in contrast with the other sponges investigated.
The table below summarizes the fatty acid composition of individual
GSLs isolated by chromatographic methods. A few, mainly saturated,
compounds were generally detected. Of interest was the first observed
occurrence of a Δ5,9 fatty acid in a glycolipid and of Δ5 and Δ6 unsaturated acids.
Fatty acid composition of some individual sponge glycosphingolipids.
Polymastia mamillaris (Britanny) (%)
Glycolipid A: 14:0(12.1), 18:1 (11.5), 18:0 (24.8) and 20:0 (tr.)
Glycolipid B: 14:0(10.0), 16:0 (20.6), 9-18:1 (1.5),11-18:1 (3.1),
18:0 (4.3), 20:0 (6.0), 21:0 (24.6) and 24:0 (2.2)
Dysedea sp. (Arabian gulf, Qatar) (%)
Glycolipid A: 12:0, 14:0, 6-15:1, 9-15:1, 15:0, 6-16:1, 16:0, 6-17:1,17:0,
18:2, 11-18:1, 5,9-24:2 and 17-24:1
Glycolipid B: 12:0, 14:0 <10.0), i-15:0, 15:0,5-16:1, 16:0 (44.0), i-17:0,
17:0, 5-18:1, 18:0(11.2), 19:0, 20:0, 21:0 and traces of
22:0, 23:0, 24:0, 25:0 and 26:0
New branched-chain unsaturated fatty acids and polyunsaturated fatty
acid content in gorgonians
The most interesting result was the occurrence in Leptogorgiapiccola of three
new fatty acids presented and identified as pyrrolidides (Mirallès et al.,
40