Biochemistry of Shellfish Lipids: X. Isolation of a Sphingolipid Containing 2-Monomethylamino-ethylphosphonic Acid from Shellfish

Hori, Taro; Sugita, Mutsumi; Itasaka, Osamu

doi:10.1093/oxfordjournals.jbchem.a129033

Cited by 30 publications

(17 citation statements)

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“…from m/z 276 ion), 174 (C 1 and C 2 with their derivatives), 132 (C 1 with its TMS group and C 2 with an NH 2 group), and 73 (TMS). The fragmentation pattern and the mass spectrum are typical of the derivatized phytosphingosine (11).…”

Section: Resultsmentioning

confidence: 92%

“…The purified sphingophosphonolipid was hydrolyzed with CH 3 OH/H 2 O/HCl (11:2.6:1, by vol) at 80°C overnight (11)(12)(13), and the fatty acid methyl esters (FAME) were extracted into n-hexane for analysis by gas-liquid chromatography (GLC) and MS. The remaining material was dried under N 2 and dissolved in approximately 2 mL H 2 O.…”

Section: Methodsmentioning

confidence: 99%

“…Sphingolipids have been reported in all groups of eukaryotic organisms thus far analyzed, and they occur in the membranes as phosphosphingolipids, glycosphingolipids, and inositolsphingolipids (8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20). Sphingolipids, their precursors and metabolic products (e.g., sphingosine, sphingosine-1-phosphate, and ceramide) play important roles in transmembrane signaling and appear to be important in mammalian cell proliferation, differentiation, aging, and apoptosis (21)(22)(23)(24).…”

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confidence: 99%

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A novel sphingophosphonolipid head group 1‐hydroxy‐2‐aminoethyl phosphonate in Bdellovibrio stolpii

Watanabe

Nakajima²,

Hoshino

et al. 2001

Lipids

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Members of the bacterial genus Bdellovibrio include strains that are free-living, whereas others are known to invade and parasitize larger Gram-negative bacteria. The bacterium can synthesize several sphingophospholipid compounds including those with phosphoryl bonds as well as phosphonyl bonds. In the present study, the dominant sphingophosphonolipid component was isolated by column chromatography, and the long-chain bases, fatty acids, and polar head groups were identified by thin-layer and gas-liquid chromatographic procedures. The definitive structural identity of the sphingolipid was established by nuclear magnetic resonance and mass spectrometry of hydrolysis products and the intact compound. The compound was identified as N-2'-hydroxypentadecanoyl-2-amino-3,4-dihydroxyheptadecan-1-phosphono-(1-hydroxy-2-aminoethane).

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Section: Resultsmentioning

confidence: 92%

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

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A novel sphingophosphonolipid head group 1‐hydroxy‐2‐aminoethyl phosphonate in Bdellovibrio stolpii

Watanabe

Nakajima²,

Hoshino

et al. 2001

Lipids

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“…The presence of a phosphonolipid was first found by Rouser et al (1963) in the sea anem one Anthopleura elegantissima as a sphingolipid ceramide aminoethylphosphonate. The same lipid, apart from its existence in cnidaria (Joseph, 1979;Nakhel, 1988), along with ceramide iV-methyl-aminoethylphosphonate, is widely distributed in molluscs (Hori et al, 1969;M atsubara, 1975;Joseph, 1982;Hori and sugita, 1984;Stavrakakis et al, 1989;M at subara et al, 1990;Dembitsky et al, 1992). Also, a new type of sphingophosphonolipids, aminoalkylphosphonyl cerebrosides, has been found in marine molluscs (Araki et al, 1991;Yamaguchi et al, 1992;M atsubara and Hayashi, 1993).…”

Section: Introductionmentioning

confidence: 99%

Phosphonolipids in the Mussel Mytilus galloprovincialis

Kariotoglou

Mastronicolis

1998

Zeitschrift Für Naturforschung C

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Phospholipids, Phosphonolipids, M ytilus galloprovincialis, Mussels, Food Analysis One of the possible roles of phosphonolipids is that they have a contribution to the protec tion of cellular integrity and survival of aquatic organisms (mollusca, cnidaria) as these lipids are included at high percentages. The total lipids of the edible mussel Mytilus galloprovin cialis (Mollusca, Bivalvia, M ytilidae) were found to constitute 1.27% of fresh tissue. Polar lipid com ponents constitute 61.5% of the total lipids. After separation by Solid Phase Extrac tion, the polar lipid fraction was separated by two dimensional thin-layer chromatography and the total phosphorus of each component, was determined. The main polar lipids found were: Phosphatidylcholine, 41.6 ± 0.8% (of which 11.3 ± 0.5% was glyceryl ether analog); ceramide am inoethylphosphonate 11.2 ± 0.2% plus 2.8 ± 0.1% another minor species; phosphatidylethanolamine, 26.6 ± 0.5% (of which 12.2 ± 0.3% was glyceryl ether analog). The individual ceramide aminoethylphosphonate species were isolated by preparative thin layer chromatography and the structure of the major one was confirmed by a combination of analytical and chromatographic methods. Saturated fatty acyl groups with 16 carbon atoms were the main com ponents (48.4% ) of the major ceramide aminoethylphosphonate species. Diglyceride aminoethyl phosphonates were not found in lipids of M. galloprovincialis.

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“…The precipitate was collected by centrifugation at 3000 rpm for 10 min, redissolved in 10 ml of chloroform-methanol (2: 1, vjv) and then washed three times with a 0.2 volume of 0.017% MgCI 2 , according to the method described by Folch et al 15 ) The lower phase was evaporated to dryness under reduced pressure. The isolation and purification of the sphingolipid from the total lipid was achieved by three methods; by mild alkaline hydrolysis according to Dawson l6 ) and Hori et al,17), by QAE-Sephadex column chromatography and by preparative thin layer chromatography.…”

Section: Fractionation Of Phosphorus Fractions In Agemakimentioning

confidence: 99%

Occurrence of Ceramide Aminoethylphosphonate in Edible Shellfish, AGEMAKI,Sinonovacula constricta

Tamari

Kandatsu

1986

Agricultural and Biological Chemistry

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Biochemistry of Shellfish Lipids: X. Isolation of a Sphingolipid Containing 2-Monomethylamino-ethylphosphonic Acid from Shellfish

Cited by 30 publications

References 0 publications

A novel sphingophosphonolipid head group 1‐hydroxy‐2‐aminoethyl phosphonate in Bdellovibrio stolpii

A novel sphingophosphonolipid head group 1‐hydroxy‐2‐aminoethyl phosphonate in Bdellovibrio stolpii

Phosphonolipids in the Mussel Mytilus galloprovincialis

Occurrence of Ceramide Aminoethylphosphonate in Edible Shellfish, AGEMAKI,Sinonovacula constricta

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