The first naturally occurring α‐methoxylated branched‐chain fatty acids from the phospholipids of <i>Amphimedon complanata</i>

Carballeira, Néstor M.; Alicea, Johanna

doi:10.1007/s11745-001-0672-1

Cited by 26 publications

(31 citation statements)

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“…The present work is only the second report of branched α-methoxylated phospholipid FA from any natural source, the first being our previous report from the sponge Amphimedon complanata (3). The structural similarity of these branched methoxylated FA with the known iso and anteiso 2-hydroxylated C 16 -C 17 FA implies that these compounds could have originated, although not necessarily, from the branched 2-hydroxylated FA.…”

Section: Resultsmentioning

confidence: 54%

“…We recently reported the presence of two of these FA, 2-methoxytetradecanoic acid and 2-methoxy-14-methylpentadecanoic acid, in two Caribbean sponges (3,18). Characterization of the remaining saturated 2-methoxylated acid (as the methyl ester) was possible using GC-MS and GC ECL values as compared to synthetic standards.…”

Section: Resultsmentioning

confidence: 99%

“…Characterization of the remaining saturated 2-methoxylated acid (as the methyl ester) was possible using GC-MS and GC ECL values as compared to synthetic standards. For example, the mass spectrum of the novel methyl ester 2 displayed a molecular ion peak at m/z 314 and a strong [M + −59] peak at m/z 255 (100%), together with a small peak at m/z 104 (McLafferty rearrangement) typical of an α-methoxylated saturated methyl ester (3,18).…”

Section: Resultsmentioning

confidence: 99%

“…Among these 2-methoxylated FA, a series of C 15 -C 16 iso and anteiso FA were recently discovered in the phospholipids of the marine sponge Amphimedon complanata, most likely arising from microorganisms coexisting with the sponge (3). These unprecedented FA were characterized by GC retention times and characteristic mass spectral fragmentations (3). However, there is a high probability that other sponges contain additional iso and anteiso 2-methoxylated FA in their phospholipids.…”

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confidence: 99%

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Total synthesis of 2‐methoxy‐14‐methylpentadecanoic acid and the novel 2‐methoxy‐14‐methylhexadecanoic acid identified in the sponge agelas dispar

Carballeira

Cruz

Ayala

2002

Lipids

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The phospholipid FA composition of the Caribbean sponge Agelas dispar was revisited and 40 different FA were identified. Among these a novel 2-methoxylated FA, namely, the anteiso methyl-branched 2-methoxy-14-methylhexadecanoic acid, was identified together with the recently discovered iso methyl-branched 2-methoxy-14-methylpentadecanoic acid and the normal-chain 2-methoxytetradecanoic acid. The structures of the iso and anteiso methyl-branched 2-methoxylated FA were confirmed by total syntheses, which were accomplished in seven steps and in 45-48% overall yields. Other phospholipid FA identified in A. dispar include the unusual methyl-branched 10,13-dimethyltetradecanoic acid, 3,7,11,15-tetramethylhexadecanoic (phytanic) acid, and the 11-methyloctadecanoic acid. In addition, the delta5,9 FA (5Z,9Z)-15-methyl-5,9-hexadecadienoic acid and (5Z,9Z)-5,9-octadecadienoic acid were characterized. These findings establish alternative FA biosynthetic possibilities for these marine organisms.

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Section: Resultsmentioning

confidence: 54%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

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Total synthesis of 2‐methoxy‐14‐methylpentadecanoic acid and the novel 2‐methoxy‐14‐methylhexadecanoic acid identified in the sponge agelas dispar

Carballeira

Cruz

Ayala

2002

Lipids

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“…Both of these FAs are common in nature and have been reported in sponges previously (Barnathan et al, 1996;Carballeira & Alicea, 2000;Carballeira & Lopez, 1989;Christie et al, 1992;Nechev et al, 2004). Palmitic acid is a precursor with chain elongation, desaturation and addition of side chain modifications possible (Michal & Schomburg, 2013).…”

Section: Fatty Acid and Sterol Compositionmentioning

confidence: 99%

Modelling sponge-symbiont metabolism

Watson¹

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Marine sponges are increasingly being recognised for their nutrient cycling ecosystem services, linking pelagic nutrients with the benthic ecosystem. Furthermore, sponges are the most prolific producers of bioactive secondary metabolites in the marine environment. Despite their ecological and commercial value, little is know about the metabolic processes that are responsible. The inability to produce sufficient sponge biomass, and thus specific bioactive compounds, has been repeatedly identified as a major bottleneck towards commercialising sponge holobiont derived drugs. Likewise, nutrient cycling by sponges has been a relatively recent advancement in marine ecology and the scale of this process is unknown. This thesis takes a systems approach to understanding sponge-symbiont metabolic processes by utilising the genomic resources available for the demosponge Amphimedon queenslandica and its bacterial symbiont AqS1. Specifically, I undertake genome-scale modelling and metabolic flux analyses to investigate the metabolic networks present in this sponge as well as its associated vertically-transmitted microbial symbiont. The goal of this thesis is to generate the data required for, and subsequently develop, a dual-species genome-scale metabolic model for A. queenslandica and AqS1. This will provide a framework to further our understanding of how sponges produce their biomass while living in an oligotrophic, tropical reef environment.To develop a genome-scale metabolic model, the biochemical composition of the organism must first be determined. Knowledge of the relative quantities of macromolecules and their respective building blocks (e.g. protein and amino acids) is vital, as each requires different substrates, enzymes and cofactors for their synthesis. I adapted and developed methods to characterise the composition and abundance of DNA, RNA, protein, lipids and carbohydrates in a marine sponge. These methods are described in detail that allows them to be easily transferred to other, non-model, large marine organisms. This is followed by a detailed analysis of A. queenslandica's macromolecular, amino acid, fatty acid and sterol composition. The biochemical data from this chapter was used to generate a biomass equation that represent the average composition of adult A. queenslandica in the metabolic model. 3To understand how the metabolic network may work towards producing more biomass, it must be considered in the context of the environmental conditions that naturally constrain growth. The dominant environmental constraint on growth on an oligotrophic reef system is nutrient availability.The abundance of key elements, such as carbon and nitrogen, were quantified throughout the course of a year. To investigate effects on the sponge of any changes in nutrient availability, I concurrently sampled sponges and analysed their biochemical composition to the macromolecular level. Chapter 4 presents these data and discusses a number of trends and correlations in the biochemical composition of the sponges with chan...

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Porifera (Sponges)–1

Kornprobst

2014

Encyclopedia of Marine Natural Products

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The article contains sections titled: Overview of the Universe of Sponges Metabolites of Calcarea (Calcareous Sponges) General Characteristics of Calcarea Fatty Acids Sterols Non‐Nitrogenous Derivatives of Species of the Genus Leucetta Imidazole Alkaloids and Zinc Complexes Isolated from the Genera Leucetta , Leucosolenia , and Clathrina αω‐ Bis Long‐Chain Aminoalcohols Nitrogen‐Containing Macrolides and Cyclic Peptides Other Nitrogen‐Containing Compounds of Calcarea Metabolites of Hexactinellida Classification and Membrane Constituents of Demospongiae Classification Some Physical Observations on Demosponges Shape and Size Consistency Color and Odor Diversity of Membrane Constituents: Some Examples Phospholipids and “Demospongic Acids” Fatty Acids with 5,9 Dienic Structure Other Mono‐ and Polyunsaturated Fatty Acids Branched Fatty Acids Isoprenic Acids Cyclopropanic Acids Brominated Acids 2‐ O Substituted Acids Sulfur Derivatives of Demospongic Acids Intracellular Localization and Biological Activity of Demospongic Acids Brief Reminder About Conventional Sterols Unconventional Sterols Produced by Changes in the Tetracyclic System Unconventional Sterols Produced by Polymethylation of the Side Chain Sterols with Degraded Side Chains Sterols and Stanols with Cyclopropanic and Cyclopropenic Side Chains Secosterols Polyhydroxylated Steroids and Derivatives, Peroxysterols Sulfated Sterols Chlorinated Sterols and Sterones Nitrogen‐Containing Sterols Glycolipids Secondary Metabolites of Homoscleromorpha Fatty Acids, Polyketides and Oxylipins of Plakinastrella and Plakortis Cyclic Peroxides and Peroxylactones from Plakinastrella and Plakortis Glycosides Polyhydroxylated Sterols of Oscarella lobularis Alkaloids and Other Original Nitrogen Derivatives of Plakortis and Corticium Secondary Metabolites of Astrophorida Acetylenic Fatty Acids of Stelletta Cyclitol Derivatives Glycolipids: Caminosides and Pachymosides Triterpenes of Malabaricane and Isomalabaricane: Sesterterpenes Triterpenic Glycosides and Steroidal Glycosides Substituted Tetramic Acids and Derived Glycosides Erylusamines, Erylusine, and Erylusidine Cyclic Depsipeptides, Peptolides, and Macrolactones Nitrogen‐Containing Terpenes Bengazoles and Bengamides Atypical Nitrogenous Derivatives Phosphorus‐Containing Derivatives Aromatic and Heteroaromatic Sulfated Derivatives Isotactic Polymethoxydienes of Myriastra clavosa

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The first naturally occurring α‐methoxylated branched‐chain fatty acids from the phospholipids of Amphimedon complanata

Cited by 26 publications

References 21 publications

Total synthesis of 2‐methoxy‐14‐methylpentadecanoic acid and the novel 2‐methoxy‐14‐methylhexadecanoic acid identified in the sponge agelas dispar

Total synthesis of 2‐methoxy‐14‐methylpentadecanoic acid and the novel 2‐methoxy‐14‐methylhexadecanoic acid identified in the sponge agelas dispar

Modelling sponge-symbiont metabolism

Porifera (Sponges)–1

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