Purification and characterization of deep sea shark<i>Centrophorus squamosus</i> liver oil 1‐<i>O</i>‐aklylglycerol ether lipids

Bordier, Catherine; Sellier, Nicole; Foucault, Alain; Goffic, François Le

doi:10.1007/bf02522646

Cited by 56 publications

(40 citation statements)

References 31 publications

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“…Methoxy-glyceryl ethers have been reported in shark liver oil (20) and have antibiotic activity and inhibit the growth of tumors in mice (27). It has been stated that the glyceryl ethers, including those of chimyl or batyl alcohol (or their monounsaturated derivatives), have enormous economic potential because they possess this range of healing activity (40). Shark ether lipids can become a good source of ether-linked lipids, which increase membrane plasmalogen levels in patients suffering from the genetic Zellwegere cerebrohepatorenal syndrome (41).…”

Section: Discussionmentioning

confidence: 99%

Lipids and buoyancy in Southern Ocean pteropods

Phleger

Nichols

Virtue

1997

Lipids

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The lipids of Clione limacina, a Southern Ocean pteropod (order Gymnosomata), contain 28% diacylglyceryl ether (DAGE) (as percentage of total lipid) whereas the pteropod Limacina helicina (order Thecosomata) lacks DAGE. The alkyl glyceryl ether diols (1-O-alkyl glycerols, GE) of Clione DAGE are dominated by 16:0 (60%) and 15:0 (21%), in contrast with deep-sea shark liver DAGE, which is dominated by 18:1 GE. The fatty acid profiles of Clione and Limacina are similar (28-32% polyunsaturated, 26-34% monounsaturated) as are the sterols, which include 24-methylenecholesterol, transdehydrocholesterol, cholesterol, and desmosterol. This finding probably reflects the fact that Limacina is the major food source for Clione. Spongiobranchaea australis, another Southern Ocean pteropod (order Gymnosomata), has 0.9-1.7% DAGE, but has less lipid (3.3-4.8 mg/g lipid, wet weight) than Clione (50.8 mg/g lipid, wet weight). We propose a buoyancy role for DAGE in Clione since Limacina has bubbles for flotation which Clione lack; DAGE provides 23% more uplift than triacylglycerol at a concentration of 1.025 g/mL seawater.

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Section: Discussionmentioning

confidence: 99%

Lipids and buoyancy in Southern Ocean pteropods

Phleger

Nichols

Virtue

1997

Lipids

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“…In this regard, Deprez et al (1990), Bakes and Table 2 1-O-alkyl chain composition of DAGE from various animal species: (a) Kayama et al (1971), (b) Malins et al (1965), (c) Hallgren and Larsson (1962), (d) Mori et al (1972), (e) Hallgren et al (1974a), (f) Hayashi et al (1985), (g) Phleger et al (1997), (h) Hallgren et al (1974b). Nichols (1995), Kayama et al (1971), and Bordier et al (1996) have reported the following percentage of selachyl alcohol: 40, 42-54, 76 and 42-62%, respectively. Indeed, Table 2 indicates that selachyl alcohol is also the major alkylglycerol in DAGE from the liver oil of the spiny dogfish Squalus acanthias and the rat fish Chimaera monstrosa.…”

Section: Biosynthesis and 1-o-alkyl Chain Compositionmentioning

confidence: 96%

Ether lipids

Magnusson

Haraldsson

2011

Chemistry and Physics of Lipids

123

119

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The naturally occurring 1-O-alkyl-sn-glycerols and their methoxylated congeners, 1-O-(2'-methoxyalkyl)-sn-glycerols, are biologically active compounds, ubiquitously found in nature as diacyl glyceryl ether lipids and phosphoether lipids. The chief objective of this article is to provide a comprehensive and up to date review on such ether lipids. The occurrence and distribution of these compounds in nature are extensively reviewed, their chemical structure and molecular variety, their biosynthesis and chemical synthesis and, finally, their various biological effects are described and discussed. An unprecedented biosynthesis of the 2'-methoxylated alkylglycerols is proposed. The first synthesis of enantiopure (Z)-(2'R)-1-O-(2'-methoxyhexadec-4'-enyl)-sn-glycerol, the most prevalent 2'-methoxylated type alkylglycerol present in cartilaginous fish, is described. It was accomplished by a highly convergent five step process.

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“…Ether lipids are known to be ubiquitous in the cell membranes of mammals, 16 marine organisms 17 and archaea. 18 These ether lipids, however, are 1-O-alkyl lipids, whereas the 3-O-alkyl lipids in kribellosides are rare.…”

Section: Stereochemistry Of the Kribellosidesmentioning

confidence: 99%

Kribellosides, novel RNA 5′-triphosphatase inhibitors from the rare actinomycete Kribbella sp. MI481-42F6

et al. 2017

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Yeast capping enzymes differ greatly from those of mammalian, both structurally and mechanistically. Yeast-type capping enzyme repressors are therefore candidate antifungal drugs. The 5ʹ-guanine-N7 cap structure of mRNAs are an essential feature of all eukaryotic organisms examined to date and is the first co-transcriptional modification of cellular pre-messenger RNA. Inhibitors of the RNA 5ʹ-triphosphatase in yeast are likely to show fungicidal effects against pathogenic yeast such as Candida. We discovered a new RNA 5ʹ-triphosphatase inhibitor, designated as the kribellosides, by screening metabolites from actinomycetes. Kribellosides belong to the alkyl glyceryl ethers. These novel compounds inhibit the activity of Cet1p (RNA 5ʹ-triphosphatase) from Saccharomyces cerevisiae in vitro with IC 50 s of 5-8 μM and show antifungal activity with MICs ranging from 3.12 to 100 μg ml À1 against S. cerevisiae.

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Purification and characterization of deep sea sharkCentrophorus squamosus liver oil 1‐O‐aklylglycerol ether lipids

Cited by 56 publications

References 31 publications

Lipids and buoyancy in Southern Ocean pteropods

Lipids and buoyancy in Southern Ocean pteropods

Ether lipids

Kribellosides, novel RNA 5′-triphosphatase inhibitors from the rare actinomycete Kribbella sp. MI481-42F6

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