Carter Litchfield

Unusual C24, C25, C26 and C27 polyunsaturated fatty acids of the marine sponge Microciona prolifera.

(1) Complete characterization of the fatty acids of the marine sponge Microciona prolifera, including double bond positional isomers, has identified 95 different acids in amounts of 0.1% or more. Trace amounts of 23 other acids were found. (2) 48% of the fatty acids present have C24--C28 chain lengths. These are all saturates, monoenes, dienes and trienes; the tetraene, pentaene and hexaene acids possess the usual C18--C22 carbon chains. The numerous C24--C28 acids present apparently originate within the sponge itself, indicating a highly active chain elongation system. (3) A new family of C24, C25, C26 and C27 polyunsaturated acids with isolated double bonds has been discovered. All contain delta 5,9 unsaturation. Specific acids identified were 5,9-24:2; 5,9-25:2; 5,9-26:2; 5,9,17-26:3; 5,9,19-26:3; 5,9,19-27:3 and 5,9,20-27:3. Biosynthetic pathways for such acids are proposed, based on intermediates found in our fatty acid analyses.

Unusually high levels of C24−C30 fatty acids in sponges of the class demospongiae

Twenty genera of sponges from the class Demospongiae have been examined for fatty acid composition. All contain unusually high levels (34–79%) of C24−C30 fatty acids not generally found in other organisms. These characteristic “demospongic acids” are mostly polyunsaturated.

Occurrence ofcis-5,cis-9-Hexacosadienoic andcis-5,cis-9,cis-19-Hexacosatrienoic acids in the marine spongeMicrociona prolifera

Fatty acid analysis of the total lipids from the marine spongeMicrociona prolifera by gas liquid chromatography on an EGSS-X column revealed two major peaks with equivalent chain length values of 27.08 and 27.74. Each of these components was isolated as a separate band by thin layer chromatography on AgNO3-silicic acid. Characterization of the two unknowns by IR spectroscopy, NMR, hydrogenation, and gas liquid chromatography revealed that the unknown acids weren-26∶2 andn-26∶3 containing only nonmethylene interruptedcis-double bonds. Reductive ozonolysis identified the 26∶2 ascis-5,cis-9-hexacosadienoic acid and the 26∶3 ascis-5,cis-9,cis-19-hexacosatrienoic acid. Analysis of the fatty acid composition ofMicrociona total lipids showed 14% 26∶2 and 31% 36∶3. The neutral lipids, phosphatidylethanomaline, and phosphatidylserine all contained >41% C26 acids; but only 4% C26 was present in the phosphatidylcholine.

5,9,23-triacontatrienoic acid, principal fatty acid of the marine spongeChondrilla nucula

The marine spongeChondrilla nucula contains 34% 30∶3Δ5,9,23 in its total fatty acids. This nonmethylene-interrupted polyunsaturated acid, unknown in other living organisms, occurs mainly as an ester in phosphatidylethanolamine.

Incorporation of 1-14C-Acetate into C26 fatty acids of the marine spongeMicrociona prolifera

AbstractThe incorporation of 1-14C-acetate into the many fatty acids of the marine spongeMicrociona prolifera was investigated. Probable precursors of 26∶2Δ5,9 and 26∶3Δ5,9,19 showed high levels of radioactivity, supporting the following pathways for the biosynthesis of C26 acids:

Composition of wax esters, triglycerides and diacyl glyceryl ethers in the jaw and blubber fats of the Amazon River dolphin (Inia geoffrensis).

\begin{array}{*{20}c} {16:0 \to \to \to 26:0 \to 26:1\Delta 9 \to 26:2\Delta 5,9} \\ {16:1\Delta 9 \to \to \to 26:1\Delta 19 \to } \\ {26:2\Delta 9,19 \to 26:3\Delta 5,9,19} \\ \end{array}

Occurrence of 5,9,19-octacosatrienoic, 5,9-hexacosadienoic and 17-hexacosenoic acids in the marine spongeXestospongia halichondroides

Degradation of the unsaturated C26 acids at their double bonds showed that the14C was concentrated near the carboxyl end of the chain. Hence, chain elongation was the major mechanism for acetate incorporation into these acids.

Heterogeneity of lipid composition within the cephalic melon tissue of the pilot whale (Globicephala melaena)

Abstract 1. 1. Jaw and blubber fats from twenty different genera of Odontoceti were analyzed for lipid class composition and for iodine value. Results were compared with our previous analyses on melon fats from the same animals. 2. 2. Melon and jaw fats in each animal are very similar in lipid class composition and iodine value but differ significantly from the corresponding blubber fats. The head fats are composed of lower molecular weight and more saturated lipids than are found in the blubber. 3. 3. High levels of isovalerate lipids are found only in the families Delphinidae, Phocoenidae and Monodontidae. The Ziphiidae, Physeteridae and Platanistidae fats are almost entirely longer chain length lipids. 4. 4. Delphinidae head fats consist of triglycerides plus significant amounts (⩾ 3%) of wax ester. Phocoenidae and Monodontidae head fats are almost exclusively triglycerides with little or no (⩽ 3%) wax ester present. 5. 5. Ziphiidae blubber fats are almost entirely (⩾ 94%) wax ester, a unique characteristic distinguishing them from all other whales. 6. 6. Relative velocity of sound waves in odontocete head fats would be lowest in the families Delphinidae, Phocoenidae and Monodontidae, intermediate in the Ziphiidae and highest in the Physeteridae and Platanistidae. This may indicate several types of echolocation mechanisms within the Odontoceti.