ABSTRACT
The marine bacterial fatty acid 9-methyl-10-hexadecenoic acid was conveniently prepared in 6 steps and in a 22% overall yield, starting from commercially available methyl 10-hydroxydecanoate. The naturally occurring fatty acid has the E double bond configuration as confirmed by gas chromatographic co-elution experiments.
Subject(s)
Fatty Acids, Monounsaturated/chemical synthesis , Fatty Acids, Monounsaturated/chemistry , Gas Chromatography-Mass Spectrometry , Magnetic Resonance Spectroscopy , Stereoisomerism , Vibrio/chemistryABSTRACT
The fatty acid composition of a Pseudomonas sp. (Alteromonas) and its host, the dinoflagellate Ostreopsis lenticularis, vectors in ciguatera fish poisoning, has been studied. The major fatty acids in O. lenticularis were 16:0, 20:5n-3, and 22:6n-3, but 18:2n-6, 18:3n-3, and 18:n-3 were also identified. In contrast to other dinoflagellates, 1 8:5n-3 was not detected in O. lenticularis. Even-chain fatty acids such as 9-16:1, 11-18:1, and 13-20:1 predominated in the Pseudomonas sp. from O. lenticularis, but 1 6-20% of (E)-11-methyl-12-octadecenoic acid was also identified. The chirality of the latter was confirmed by total synthesis (28% overall yield) starting from oxacyclotridecan-2-one. The fatty acid compositions of two other Pseudomonas species, from the palytoxin-producing zoanthids Palythoa mamillosa and P. caribdea, were also studied and were similar to that of the Pseudomonas sp. from O. lenticularis. The possibility of using some of these fatty acids as chemotaxonomic lipids in identifying marine animals that consume toxic dinoflagellates or zoanthids is discussed.
Subject(s)
Cnidaria/microbiology , Dinoflagellida/microbiology , Fatty Acids/analysis , Pseudomonas/chemistry , Acrylamides/metabolism , Animals , Ciguatoxins/biosynthesis , Cnidaria/pathogenicity , Cnidarian Venoms/metabolism , Dinoflagellida/pathogenicity , Fatty Acids/chemistry , Pseudomonas/isolation & purification , Pseudomonas/pathogenicity , SymbiosisABSTRACT
The phospholipid fatty acid composition of Eunicea succinea was investigated, and the novel (5Z,9Z)-14-methyl-5,9-pentadecadienoic acid was identified. Structural characterization was accomplished by means of mass spectrometry of its pyrrolidide derivative, NMR, FT1R, and total synthesis. Other interesting phospholipid fatty acids in E. succinea were the tetracosapolyenoic acids 6,9,12,15,18,21-tetracosahexaenoic acid (24:6) and 6,9,12,15,18-tetracosapentaenoic acids (24:5). The title compound was particularly active against Gram-positive bacteria such as Staphylococcus aureus (MIC 0.24 mumol/mL) and Streptococcus faecalis (MIC 0.16 mumol/ mL).
Subject(s)
Anti-Bacterial Agents/isolation & purification , Cnidaria/metabolism , Fatty Acids, Unsaturated/isolation & purification , Animals , Anti-Bacterial Agents/pharmacology , Bacteria/drug effects , Fatty Acids, Unsaturated/pharmacology , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Spectroscopy, Fourier Transform InfraredABSTRACT
The fatty acid compositions of the hyperthermophilic microorganisms Thermotoga maritima and Pyrococcus furiosus were studied and compared. A total of 37 different fatty acids were identified in T. maritima, including the novel 13,14-dimethyloctacosanedioic acid. In contrast, a total of 18 different fatty acids were characterized, as minor components, in P. furiosus, and these included saturated, monounsaturated, and dicarboxylic acids. This is the first report of fatty acids from an archaeon.
Subject(s)
Archaea/chemistry , Fatty Acids/analysis , Gram-Negative Anaerobic Bacteria/chemistryABSTRACT
The fatty acid composition of a new strain of Vibrio alginolyticus, found in the alga Cladophora coelothrix, was studied. Among 38 different fatty acids, a new fatty acid, 9-methyl-10-hexadecenoic acid and the unusual 11-methyl-12-octadecenoic acid, were identified. Linear alkylbenzene fatty acids, such as 10-phenyldecanoic acid, 12-phenyldodecanoic acid and 14-phenyltetradecanoic acid, were also found in V. alginolyticus. The alga contained 43% saturated fatty acids, and 28% C16-C20 polyunsaturated fatty acids of the n-3 and n-6 families.
Subject(s)
Chlorophyta/microbiology , Fatty Acids, Monounsaturated/analysis , Fatty Acids/analysis , Vibrio/chemistry , Chlorophyta/chemistry , Fatty Acids, Unsaturated/analysis , Mass SpectrometryABSTRACT
The phospholipid fatty acid composition of Holothuria mexicana was investigated, and the novel 7-methyl-6-octadecenoic acid was identified. Structural characterization was accomplished by means of pyrrolidide derivatization and total synthesis. Other interesting phospholipid fatty acids in H. mexicana were 7-eicosenoic acid, 13-tricosenoic acid, 7-methyl-6-hexadecenoic acid, and 2-hydroxy-15-tetradecenoic acid.
Subject(s)
Echinodermata/chemistry , Oleic Acids/chemistry , Animals , Chromatography, Gas , Fatty Acids/chemistry , Isomerism , Oleic Acids/isolation & purification , Phospholipids/chemistryABSTRACT
The phospholipid fatty acid composition of the Caribbean gorgonians Pseudopterogorgia acerosa (Pallas), Pseudopterogorgia americana (Gmelin), Pseudopterogorgia bipinnata (Verrill) and Pseudopterogorgia rigida (Bielschowsky) is described for the first time. The main phospholipids identified were phosphatidylethanolamine, phosphatidylcholine and phosphatidylserine. All four gorgonians presented a similar phospholipid fatty acid composition. The main fatty acids were 16:0, 18:3(n-6), 18:4(n-3), 20:4(n-6), 22:6(n-3), 24:5(n-6) and 24:6(n-3). In all of the studied Pseudopterogorgia gorgonians, high amounts of the tetracosapolyenoic fatty acids 24:5(n-6) and 24:6(n-3) were identified. In the four gorgonians studied, n-6 polyunsaturated fatty acids predominated. These results suggest that the occurrence of tetracosapolyenoic fatty acids in the Gorgoniidae is more general than previously recognized.
