Identification of a New 6-Bromo-5,9-eicosadienoic Acid from the Anemone Condylactis gigantea and the Zoanthid Palythoa caribaeorum

Carballeira, Néstor M.; Reyes, Morayma

doi:10.1021/np50125a007

Cited by 31 publications

(15 citation statements)

References 18 publications

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“…Trace, <0.01%; -, not detected. (9,15,16). Therefore, the long-chain NMI FA 5,9-22:2, 5,9-24:2, 5,9,15-24:3, and 5,9,17-24:3 detected in this study might be biosynthesized by the limpet itself or by some of its symbiotic organisms.…”

Section: Resultsmentioning

confidence: 58%

“…The NMI diene FA 5,9-18:2, 5,9-22:2, and 5,9-24:22 are found in the phospholipids of the Caribbean sponges Plakortis halichondroides and Calyx podatypa (14,15) and in the phospholipids of the anemone Condylactis gigantea and the zoanthid Palythoa caribaeorum (16). In contrast, 5,9-18:2 is also found in terrestrial seed lipids as well as in some marine sponge lipids a Values are expressed as mean ± SD (n = 3).…”

Section: Resultsmentioning

confidence: 99%

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Unusual minor nonmethylene‐interrupted di‐, tri‐, and tetraenoic fatty acids in limpet gonads

Kawashima

2005

Lipids

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Unusual minor nonmethylene-interrupted (NMI) FA have been identified in the lipids of gonads from the limpets Cellana grata and Collisella dorsuosa by using GC-MS of the combination of their 4,4-dimethyloxazoline derivatives and picolinyl esters. Among 23 NMI unsaturated FA from C18 to C22 and C24 identified in this study, 5,11-nonadecadienoic (5,11-19:2), 7,1 6-heneicosadienoic (7,16-21:2), 9,15-tetracosadienoic (9,15-24:2), 5,9,15-docosatrienoic (5,9,15-22:3), and 5,9,15-tetracosatrienoic (5,9,15-24:3) acids may not have been reported previously from living organisms. The presence of 5,11,14,17-eicosatetraenonoic (5,11,14,17-20:4) and 7,13,16,19-docosatetraenenoic (7,13,16,19-22:4) acids as FA components in marine mollusks may be reported here for the first time. In this study, the male and female gonads of both species showed distinct differences in both their composition and proportions of NMI FA. Most NMI FA identified were mainly present in the female gonads of both species, especially in TAG that contained 21 NMI FA.

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Section: Resultsmentioning

confidence: 58%

Section: Resultsmentioning

confidence: 99%

Unusual minor nonmethylene‐interrupted di‐, tri‐, and tetraenoic fatty acids in limpet gonads

Kawashima

2005

Lipids

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“…A particularly interesting point is the presence of 6-Br-5,9-FAs that are very common in demosponges but quite rare in other organisms. To the best of our knowledge only some Cnidaria Hexacorallia were shown to contain these brominated FAs [21–23], which prove the existence of bromoperoxidases in this group of Cnidaria since it has been proved that these brominated demospongic acids are synthesized by the sponge itself in the final stage of biosynthesis [24]. …”

Section: Occurrence Of “Demospongic” Acids Among Other Organismsmentioning

confidence: 99%

Demospongic Acids Revisited

Kornprobst

Barnathan

2010

Marine Drugs

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The well-known fatty acids with a Δ5,9 unsaturation system were designated for a long period as demospongic acids, taking into account that they originally occurred in marine Demospongia sponges. However, such acids have also been observed in various marine sources with a large range of chain-lengths (C16–C32) and from some terrestrial plants with short acyl chains (C18–C19). Finally, the Δ5,9 fatty acids appear to be a particular type of non-methylene-interrupted fatty acids (NMA FAs). This article reviews the occurrence of these particular fatty acids in marine and terrestrial organisms and shows the biosynthetic connections between Δ5,9 fatty acids and other NMI FAs.

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“…In order to distinguish between these possibilities and to determine the origin of the residual scFAs in DK5614, deuterated butyric acid (1 mM [ 2 H 7 ]-butyric acid) was fed to the wild type and the mutant, and its incorporation into the FAs as a starter unit was determined by gas chromatography-mass spectrometry analysis of the FA picolinyl esters (www.lipidlibrary.co.uk) resulting from alkaline hydrolysis of whole cells and the subsequent reaction of the free FAs with 3-hydroxymethylpyridine in the presence of N,NЈ-dicyclohexylcarbodiimide and 4-dimethylamino pyridine, similarly to a published procedure (3). Whereas 14% of the major scFA 16:15c was labeled in the wild type, the incorporation in DK5614 was 100%.…”

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confidence: 99%

Straight-Chain Fatty Acids Are Dispensable in the Myxobacterium Myxococcus xanthus for Vegetative Growth and Fruiting Body Formation

et al. 2006

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Inactivation of the MXAN_0853 gene blocked the production in Myxococcus xanthus of straight-chain fatty acids which otherwise represent 30% of total fatty acids. Despite this drastic change in the fatty acid profile, no change in phenotype could be observed, which contrasts with previous interpretations of the role of straight-chain fatty acids in the organism's development.Myxobacteria have very complex fatty acid (FA) profiles, with up to 40 different compounds belonging to all known classes of FAs (2, 27). The most dominant fatty acid usually belongs to the iso-branched fatty acids (iso-FAs), which contribute up to 80% of total FAs in some species. All other fatty acids are straight-chain fatty acids (scFAs), whereas anteisoFAs are found only as trace compounds in myxobacteria. Interestingly, mono-and diunsaturated species as well as 2-OH and 3-OH derivatives of these FAs are common in myxobacteria, and iso-2-OH FAs especially have been proposed as chemotaxonomic markers to identify myxobacteria and other gliding bacteria (7). The resulting abundance of different fatty acids is unexpected because several bacteria from different environments, like Escherichia coli, bacilli, and actinomycetes, live with much simpler fatty acid profiles. One might argue that this mixture allows myxobacteria to maintain their membrane fluidity over a broad temperature range, but except for some thermophilic species (8), almost all myxobacteria described are mesophiles, most of which grow only in a narrow temperature range. Additionally, myxobacteria possess members of different FA families thought to fulfill the same functions (e.g., isoand unsaturated FAs) (13). Even FAs with more than one functional group can be observed in substantial amounts.It was postulated previously that some of these FAs play a role in the complex life cycle of myxobacteria which culminates in the formation of fruiting bodies containing heat-and desiccation-resistant myxospores (11,22). The model organism for studying the development of and sporulation in myxobacteria is Myxococcus xanthus, for which different extracellular signals and regulators have already been described. These are required for M. xanthus to proceed through the developmental program (12). However, the underlying biochemistry is barely understood. It was shown previously by Toal et al. that disruption of the branched-chain keto acid dehydrogenase (Bkd) complex results in a developmental phenotype with almost no aggregates or spores formed under starvation conditions (25). The Bkd complex is involved in the degradation of the branched-chain amino acids leucine, valine, and isoleucine to isovaleryl-coenzyme A (isovaleryl-CoA), isobutyryl-CoA, and 2-methylbutyryl-CoA, respectively. These thioesters are the starting units for iso-and anteiso-fatty acids and for several secondary metabolites from different bacteria (e.g., avermectin from Streptomyces avermitilis [6] and myxothiazol [24], myxalamides [23], and aurafuron [16] from Stigmatella aurantiaca).In all myxobacteria analyzed so far, ...

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Identification of a New 6-Bromo-5,9-eicosadienoic Acid from the Anemone Condylactis gigantea and the Zoanthid Palythoa caribaeorum

Cited by 31 publications

References 18 publications

Unusual minor nonmethylene‐interrupted di‐, tri‐, and tetraenoic fatty acids in limpet gonads

Unusual minor nonmethylene‐interrupted di‐, tri‐, and tetraenoic fatty acids in limpet gonads

Demospongic Acids Revisited

Straight-Chain Fatty Acids Are Dispensable in the Myxobacterium Myxococcus xanthus for Vegetative Growth and Fruiting Body Formation

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