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

Mishra, Pravat Manjari; Sree, A.

doi:10.1007/s10600-008-9043-x

Cited by 7 publications

(13 citation statements)

References 22 publications

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“…They are found in most living organisms from humans to autotrophic and heterotrophic lower organisms, including microalgae, sponges, bacteria, and fungi ( 1,9,(11)(12)(13)(14)(15). VLC-FA are found mainly in seed oils, plant waxes, cutin, suberin, skin, hair, and wax glands ( 1 ), whereas VLC-PUFA are found primarily in retina, brain ( 1, 16 ), testis, and spermatozoa ( 17-19 ).…”

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Retinal very long-chain PUFAs: new insights from studies on ELOVL4 protein

Agbaga

Mandal

Anderson

2010

Journal of Lipid Research

147

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This article is available online at http://www.jlr.org tively rare compared with the abundance of FA containing 16-22 carbons, they are widely distributed in higher plants and animals ( 1-10 ). They are found in most living organisms from humans to autotrophic and heterotrophic lower organisms, including microalgae, sponges, bacteria, and fungi ( 1,9,(11)(12)(13)(14)(15). VLC-FA are found mainly in seed oils, plant waxes, cutin, suberin, skin, hair, and wax glands ( 1 ), whereas VLC-PUFA are found primarily in retina, brain ( 1, 16 ), testis, and spermatozoa ( 17-19 ).The unusually long hydrocarbon chains with 3 -9 double bonds, which are prone to oxidative damage, combined with the small quantities found in mammalian tissues, have made them diffi cult to isolate and analyze in detail over the years ( 9 ). Very little is therefore known about the metabolism and function of VLC-PUFA and VLC-FA in mammals, except for their increase in disorders of peroxisomal function ( 3,16,20,21 ), as components of the secretions of meibomian glands (22)(23)(24)(25)(26)(27), and their reduction in animal models of autosomal dominant Stargardt-like macular dystrophy (STGD3) ( 28-32 ), a juvenile form of macular degeneration. In contrast, the roles of long-chain PUFA (LC-PUFA) with carbon chains that range from C18 to C24 are fairly well understood, especially in the retina and other neural tissues. A detailed account on the role and function of LC-PUFA in the retina was reviewed earlier (33)(34)(35)(36).Recent interest in the molecular and physiological roles of VLC-PUFA in the retina came from the fi nding that the gene associated with STGD3 shared sequence homologies with genes involved in FA elongation ( 37,38 ) Abbreviations: AOX, acyl-CoA oxidase; DHA or 22:6n3, docosahexaenoic acid; ELOVL, elongation of very long-chain FA; ELOVL4, elongation of very long-chain FA-4; ERG, electroretinogram; LC-PUFA, long-chain PUFA; PC, phosphatidylcholine; ROS, retinal outer segments; RPE, retinal pigment epithelium; STGD1, recessive Stargardt degeneration; STGD3, autosomal dominant Stargardt-like macular dystrophy; VLC-FA, very long-chain saturated or monounsaturated FA; VLC-PUFA, very long-chain PUFA.

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confidence: 99%

Retinal very long-chain PUFAs: new insights from studies on ELOVL4 protein

Agbaga

Mandal

Anderson

2010

Journal of Lipid Research

147

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“…For example, Litchfield isolated 26:2∆5,9 (1) and 26:3∆5,9,19 (2) from marine sponges Microciona prolifera and Xestospongia halichondroides [4,5], and Warkup also reported several 5,9-dienoic acids 3-6 from a sponge Aplysina fistularis in 1981 [6]. Since then, it is widely recognized that trace amounts of various NMIFA with a 5,9-dienoic acid structure are frequently found in marine sponges and mollusks [9][10][11][12][13][14][15][16][17][18][19][20][21] (Scheme 1). Since then, it is widely recognized that trace amounts of various NMIFA with a 5,9-dienoic acid structure are frequently found in marine sponges and mollusks [9][10][11][12][13][14][15][16][17][18][19][20][21] (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

“…Carballeira found several unique fatty acids with a 5,9-dienoic structure (7)(8)(9)(10)(11)(12)(13)(14) from the sea anemones Stoichactis helianthus, Condylactis gigantea, and from a zoanthid Palythoa caribaeorum in 1994-1995 [7,8]. Since then, it is widely recognized that trace amounts of various NMIFA with a 5,9-dienoic acid structure are frequently found in marine sponges and mollusks [9][10][11][12][13][14][15][16][17][18][19][20][21] (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

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Total Synthesis and Structural Elucidation of Two Unusual Non‐Methylene‐Interrupted Fatty Acids in Ovaries of the Limpet Cellana toreuma

Shimada

Sugawara

Korenaga

et al. 2017

Lipids

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In our previous study, unusual odd-numbered dienoic acids with a terminal olefin were found as minor components in ovaries of the Japanese limpet Cellana toreuma, and the synthetic interests have been focused onto their structural confirmation and the inspection into their potential biological activity. Here, we describe an efficient and stereoselective total synthesis of two new unusual dienoic acids, 19:2∆7,18 and 21:2∆7,20, through a common pathway involving the strategic combination of alkyne-zipper reaction and Lindlar hydrogenation for the construction of their unique carbon chains. In our synthetic study, 2-propyn-1-ol was at first subjected to alkylation and alkyne-zipper reaction to form the two fragments, and the subsequent carbon chain elongation was achieved by the usual coupling reaction to obtain the C-19 and C-21 products bearing an internal acetylenic group. Then, the internal acetylenic group of these products was subjected to Lindlar hydrogenation to form a Z-alkenyl moiety, and the subsequent deprotection of the products was carried out under an acidic condition without isomerization of the internal Z-alkenyl group. Total synthesis of target fatty acids, 19:2∆7,18 and 21:2∆7,20, was finally accomplished by two-step oxidation of the resulting alcohols into carboxylic acids in a highly chemoselective manner, and the structures of these unusual natural fatty acids were finally elucidated by identifying the GC-MS spectra of the methyl esters of authentic and synthetic fatty acids.

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“…Among the aquatic animals, sponges are characterized by the greatest diversity of fatty acids (FA), sterols, etc. Fatty acids and sterols as lipid components of sponges have been elaborately studied by a number of investigators [1][2][3][4][5][6]. Some lipids of sponges are characterized as biologically active [7][8][9].…”

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Fatty Acid Profile, Sterol Composition of Lipids, and Antibacterial Study of the Marine Sponge Psammaplysilla purpurea Collected from the Bay of Bengal (Odisha Coast)

et al. 2014

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Marine sponges are the most primitive multicellular sedentary animals that produce bioactive metabolites. Among the aquatic animals, sponges are characterized by the greatest diversity of fatty acids (FA), sterols, etc. Fatty acids and sterols as lipid components of sponges have been elaborately studied by a number of investigators [1][2][3][4][5][6]. Some lipids of sponges are characterized as biologically active [7][8][9].The sponge Psammaplysilla purpurea (order Verongida, family Aplysinellidae) is a well-known source of several bromotyrosine alkaloids of unique structural features and exhibiting promising biological activities such as cytotoxicity, antimicrobial properties, etc. [10][11][12][13]. The methanol and dichloromethane extracts of this species have shown broad-spectrum larvicidal and insecticidal activity [14]. However there has been no report on the FA profile of the lipid composition of P. purpurea. This is the first report on the analysis of the FA and sterol composition of the sponge P. purpurea collected from the Bay of Bengal region of the Odisha coast. The search for FAs and sterols of the lipophilic extract of P. purpurea can give valuable information on its chemotaxonomy. Thus, these minor components appear as biomarkers for such organisms.Forty-nine fatty acids were identified in the mixture of total lipids of P. purpurea by GC-MS analysis (Table 1). Peak identification was carried out by comparison of the mass spectra with those available in the NIST and WILEY libraries and also confirmed by comparison of their chromatographic retention times as well as mass fragmentations with those of authentic standards C-4-C-24 (Supelco standard FAME mixtures). Among the identified fatty acids, saturated linear FAs account for more than 50% of the total FA content, which is an important observation. All of the acids from 12:0 to 27:0 were found except 13:0. Generally, among saturated fatty acids, 16:0 and C18:0 dominated in most of the sponges. But in the present investigation, the acids 19:0 and 16:0 were dominant. Long-chain saturated fatty acids like 22:0 to 27:0 are present, among which 26:0 is present in good amount (6.04%).In sponges, branched saturated iso/anteiso acids with a total number of carbon atoms from C-14 to C-29 were found, among which C-15-C-20 acids were the most widespread [15]. In the present investigation, 24 saturated monobranched FAs were identified (29.92%), br-16:0 and br-14:0 being the major ones. It is considered that saturated iso and anteiso C-15-C-20 acids have a bacterial origin [16]. The ratio of iso and anteiso FAs is much higher in sponges, a significant part of whose biomass is compounded by bacterial symbionts. Thus, in the sponge P. purpurea the content of iso and anteiso may be due to symbiotic bacteria. Only one polybranched FA was identified, i.e., 3,7,11,15-tetramethylhexadecanoic acid (br-16:0, 4.38%), which is very often found in marine sponges [17]. The identification of 3,7,11,15-tetramethyl-16:0 was finally confirmed by comparing its key mass fragments (...

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

Cited by 7 publications

References 22 publications

Retinal very long-chain PUFAs: new insights from studies on ELOVL4 protein

Retinal very long-chain PUFAs: new insights from studies on ELOVL4 protein

Total Synthesis and Structural Elucidation of Two Unusual Non‐Methylene‐Interrupted Fatty Acids in Ovaries of the Limpet Cellana toreuma

Fatty Acid Profile, Sterol Composition of Lipids, and Antibacterial Study of the Marine Sponge Psammaplysilla purpurea Collected from the Bay of Bengal (Odisha Coast)

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