Identification of the new 23‐methyl‐5,9‐pentacosadienoic acid in the sponge<i>Cribrochalina vasculum</i>

Carballeria, Néstor M.; Reyes, Elba D.

doi:10.1007/bf02562431

“…The C26:2(5, 9) is a major constituent of the FAs of the Demospongiae class. There are species of the Demospongiae class having no or trace amounts of the C26:2 (5,9) [5,7], but there are the species of the Demospongiae class which contain very high amount of C26:2 (5,9) [6,11]. Both specimen of A. carteri of our investigation contained C26:2 (5,9) which constitutes more than 40% of the total FA mixtures.…”

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confidence: 87%

“…In the literature it is reported that these are the rare acids which were found in Caribbean sponges [9], and it was believed that such acids have bacterial origin [10,11]. So the presence of symbiotic bacteria cannot be excluded.…”

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confidence: 99%

“…The sponge species collected from 28 m depth is found to contain 58.94% of unsaturated fatty acids, which includes 52.87% of C26:2 (5,9), a polyunsaturated fatty acid (PUFA), while the sponge collected from 13 m depth was found to contain 46.75% of unsaturated fatty acids, which includes 42.75% of C26:2 (5,9). Important PUFAs such as C20:5 (5,8,11,14,17) and C20:4 (5,8,11,14) were present in the species collected from depth (0.43% and 2%, respectively), while these were not found in the species collected from shallow water.…”

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confidence: 99%

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Composition of the lipophilic extract from the sponge Axinella carteri collected from the Bay of Bengal of the Orissa coast

Mishra

¹

,

Sree

²

2008

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547.915The composition of the lipophilic extract from the two specimen of the sponge Axinella carteri (Dendy) collected from two different depths of the Bay of Bengal of the Orissa coast were investigated. Fatty acids, as well as volatile compounds and sterols, were identified. A high concentration of polyunsaturated fatty acids was identified from depth species compared to the species collected from shallow water. The presence of a high concentration of a polymethyl-branched fatty acid, i.e., phytanic acid, and a demospongic acid (C26:2, Δ 5,9) were identified in both specimen, but the % composition of both acids were more in the species collected from depth than the species collected from shallow water. Important polyunsaturated fatty acids like 5,8,11,8,11,14, were also found in depth species which were absent in the species collected from shallow water. Antimicrobial screening of the lipid extracts of A. carteri was also studied against different pathogens.This work aims at extending knowledge on sponge lipids, especially for the genus Axinella (Dendy). Earlier bioactive alkaloids and cyclopeptides have been isolated from the tropical marine sponge Axinella carteri (Dendy) [1,2]. Previously bioactive pyrrole-derived alkaloids and triterpenes have been isolated from other Axinella sp. [3,4]. But much less work has been done in analyzing the fatty acid composition of these bioactive marine sponges. Differences in the lipid composition of the sponge from the two collection sites could have adaptive value. There are no investigations on the fatty acid composition of the A. carteri (Dendy) collected from the Bay of Bengal of the Orissa coast. We report here the total fatty acid composition of sponge species A. carteri (Dendy) collected from two different depths (13 m depth and 28 m depth) of the Bay of Bengal of the Orissa Coast. Antimicrobial screening of the lipid extracts of A. carteri was also studied against different pathogens.GC-MS analysis of the total lipid of the sponge A. carteri (Dendy) collected from two different depths of the Bay of Bengal of Orissa showed marked differences in their fatty acid composition (Table 1). The sponge species collected from 28 m depth contained a greater number of fatty acids when compared to the species collected from 13 m depth.The sponge species collected from 28 m depth is found to contain 58.94% of unsaturated fatty acids, which includes 52.87% of C26:2(5,9), a polyunsaturated fatty acid (PUFA), while the sponge collected from 13 m depth was found to contain 46.75% of unsaturated fatty acids, which includes 42.75% of C26:2(5,9). Important PUFAs such as C20:5(5,8,11,14,17) and C20:4(5,8,11,14) were present in the species collected from depth (0.43% and 2%, respectively), while these were not found in the species collected from shallow water. It was revealed that the % composition of saturated straight chain fatty acids was greater in sp. collected from shallow water (30.31%) when compared to the species collected from depth (6.42%), which is an important finding in...

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“…The principal ones without methylene separation were 26:2(∆5,9), 26:3(∆5, 9,19), 27:2(∆5,9), 28:3(∆5, 9,19), 28:3(∆5, 9,21), and 28:3(∆5, 9,23), which are typical for sponges (Table 1). Other polyunsaturated FA included arachidonic 20:4(∆5, 8,11,14), eicosapentaenoic 20:5(∆5, 8,11,14,17), and docosahexaenoic 22:6(∆4, 7,10,13,16,19).…”

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confidence: 98%

“…Such acids are usually considered to originate from bacteria [18,19]. Saturated FA with one branching in the middle of the chain, for example, 10-Me-16:0, 10-Me-18:0, 11-Me-18:0, and 13-Me-20:0 were previously found in other sponges [20][21][22][23]. We assume that such acids are synthesized by bacteria associated with the sponges and are very characteristic just for demosponges bacterial symbionts [24,25].…”

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confidence: 99%

Fatty Acids from the Sponge Tedania dirhaphis

Rodkina

¹

2005

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Marine sponges are the most primitive multicelled organisms. The unique ability of these organisms to adapt to any ecosystem may be due to biochemical factors, in particular, the structural features of their membranes. It is known that the main components of sponge membranes, phospholipids, consist of fatty acids (FA) of the usual length (16-22 C atoms) in addition to a large amount of unusual FA of longer chain length [1,2]. These were identified using modern research methods. They include brominated FA [3][4][5], unsaturated FA with double bonds in unusual positions [6], branched FA [7], and acids with unusual substituents such as cyclopropane [8], methoxyl [9], acetoxyl [10], and others in the C chain. It was also shown that many unusual FA isolated from sponges have biological activity [11][12][13].We investigated for the first time the FA composition of the marine sponge Tedania dirhaphis from the Sea of Okhotsk. Using modern GC-MS methods we identified new saturated and monoenoic acids that had not been previously observed in other sponges: 16-Me-19:0, 10,14-Me 2 -15:1(∆6), 18:1(∆6), 18:1(∆8), 22:1(∆16). Information on the FA composition of sponges broadens our understanding of the diversity of biological molecules.According to GC, the FA mixture of total lipids from T. dirhaphis contained more than 70 components, 50 of which (98.4%) were identified ( Table 1).The saturated FA made up 8.3% of the total FA from T. dirhaphis; total saturated branched FA, 3.2%. The principal saturated acids were 16:0, 18:0, and 16-Me-19:0. The last has not been observed previously in other sponges.The pyrrolidide of 16-Me-19:0 has a molecular ion [M] + with m/z 365 but differs in chromatographic mobility and peak intensities of characteristic ions from the pyrrolidide of linear 20:0 acid. It is known that the intensity of the peak characterizing the branching position is minimal whereas those of the neighboring peaks increase, i.e., a gap of 28 amu forms, if branching is present [14]. In the spectrum of the pyrrolidide of 16-Me-19:0, the intensity of the peak with m/z 308 (0.0%) is less whereas those of the neighboring peaks with m/z 294 (1.1%) and 322 (1.5%) are greater than those of the pyrrolidide of 20:0. This indicates that the methyl group is located on the 16th C atom.Other saturated FA with branched C chains that were present included i/ai, 15:0; i, 16:0, and i/ai 17:0; i/ai 19:0; i/ai 21:0, which have been observed previously in sponges and other organisms [15][16][17]. Such acids are usually considered to originate from bacteria [18,19]. Saturated FA with one branching in the middle of the chain, for example, 10-Me-16:0, 10-Me-18:0, 11-Me-18:0, and 13-Me-20:0 were previously found in other sponges [20][21][22][23]. We assume that such acids are synthesized by bacteria associated with the sponges and are very characteristic just for demosponges bacterial symbionts [24,25].The total monoenoic FA made up 13.1% of the total FA from T. dirhaphis. The principal ones were 16:1

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Porifera (Sponges)–1

Kornprobst

¹

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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Identification of the new 23‐methyl‐5,9‐pentacosadienoic acid in the spongeCribrochalina vasculum

Cited by 28 publications

References 10 publications

Composition of the lipophilic extract from the sponge Axinella carteri collected from the Bay of Bengal of the Orissa coast

Composition of the lipophilic extract from the sponge Axinella carteri collected from the Bay of Bengal of the Orissa coast

Fatty Acids from the Sponge Tedania dirhaphis

Porifera (Sponges)–1

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