Isolation and Characterization of the N-Methyl Derivatives of 2-Aminoethylphosphonic Acid from the Sea Anemone, Anthopleura xanthogrammica<sup>*</sup>

Kittredge, James S.; Isbell, A. F.; Hughes, R. R.

doi:10.1021/bi00853a045

Cited by 63 publications

(14 citation statements)

References 17 publications

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“…Table 6 shows that the water-soluble products from compounds 8 and 9 have an R, lower than that of 2-aminoethylphosphonic acid in two paper chromatographic systems. This would appear to rule out the possibility that the substance is a N-methyl derivative of aminoethylphosphonate since all three naturally occurring methylated compounds have R, values higher than aminoethylphosphonate in solvent 1 ( Table 6; 11).…”

Section: Resultsmentioning

confidence: 99%

“…Naturally occurring phosphonolipids are all derivatives of 2-aminoethylphosphonate (NH2CH,CH2PO,H2). As mentioned above, this compound and its N-methyl derivatives appear to be ruled out, based on partition chromatography (11). The compound with a carboxyl at carbon 2 is known (12) and would be expected to be adsorbed more strongly at an alkaline pH to an anion exchange column than would aminoethyl phosphonate.…”

Section: Resultsmentioning

confidence: 99%

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Occurrence of Phosphonosphingolipids in Bdellovibrio bacteriovorus Strain UKi2

1973

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The major phospholipids of two strains of Bdellovibrio bacteriovorus were characterized. Both strain UKil, which is obligately saprophytic, and strain UKi2, which is facultatively parasitic, contained phosphatidylethanolamine and phosphatidylglycerol as their major glycerophosphatides. A branched, 15-carbon fatty acid is the major component of these alkali-labile lipids. Absent from UKil but present in UKi2 were three alkali-stable lipids (compounds 8, 9, and 11) which appear to be phosphosphingolipids. After acid hydrolysis, both compound 8 and 9 yield the identical phosphorus-containing substance that is water soluble, dipolar ionic, and ninhydrin positive. This substance appears to contain a C-P bond since P1 could not be released from this substance by treatment with alkaline phosphatase or by very harsh mineral acid treatment. Based on chromatographic comparisons, this phosphonate appears to be a novel lipid constituent. Upon degradation, compound 8 yields 1 mol of dihydroxy long-chain base and compound 9 yields 1 mol of a trihydroxy long-chain base. These bases appear to have a 17-carbon, possibly branched, structure based on gas-liquid chromatography retention times. Degradation of both sphingolipids yields a mixture of hydroxy fatty acids, the major component being a branched, 15-carbon hydroxy acid. 1971).MATERIALS AND METHODS Growth of bacteria. B. bacteriovorus strains UKil and UKi2 (4) were grown on 1% (wt/vol) peptone-0.3% (wt/vol) yeast extract on a rotary shaker at 30 C for 15 h. In some experiments the medium was supplemented with "2P-orthophosphate (carrier-free, New England Nuclear Corp., or ICN Corp.).Extraction of lipid. The phospholipids were extracted according to a modification of the method of Lester and Steiner (17). '2P-lieled cells were harvested from 25 ml of medium by centrifugation and suspended in 1.0 ml of water. A 5-ml amount of (CH2CH2)20-CH,CH2OH (3:1, vol/vol) was added, on July 16, 2020 by guest

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Occurrence of Phosphonosphingolipids in Bdellovibrio bacteriovorus Strain UKi2

1973

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“…Subsequently Kittredge, Roberts & Simonsen (1962) obtained evidence that the same compound was present in the sea anemone, Anthopleura elegantissima, from which a new phospholipid, ceramide aminoethylphosphonate (ceramide ciliatine), was isolated and characterized by Rouser, Kritchevsky, Heller & Lieber (1963). The same phospholipid has been isolated by Hori, Itasaka & Inoue (1966) from the shellfish Corbicula sandai, and it is now believed that compounds, including lipids, containing the C-P bond are by no means uncommon in marine organisms (Quin, 1965;de Koning, 1966;Kittredge, Isbell & Hughes, 1967). Ciliatine has also been found in total hydrolysates of Tetrahymena pyriformis (Kandatsu & Horiguchi, 1962), and Liang & Rosenberg (1966) have obtained evidence that diacylglyceryl 2-aminoethylphosphonate (diglyceride ciliatine) is present in these protozoa.…”

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The aminoethylphosphonate-containing lipids of rumen protozoa

Dawson

Kemp

1967

Biochemical Journal

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1. A method is presented for identifying and estimating the aminoethylphosphonate (ciliatine)-containing phospholipids in a complex mixture. 2. Evidence was obtained that the phospholipids of a pure culture of Entodinium caudatum and a mixed rumen protozoa sample contain diglyceride ciliatine, and a plasmalogen ciliatine was detected in the latter. 3. A ninhydrin-positive sphingolipid was isolated from rumen protozoa. Although chromatographically homogeneous on silica gel it contains two components, which were provisionally identified as ceramide ciliatine and ceramide phosphorylethanolamine. 4. A detailed phospholipid analysis of E. caudatum and rumen protozoa is presented. They contain no phosphatidylserine or cardiolipin, but an unidentified phosphoglyceride containing a zwitterionic amino acid is present.

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“…AEP (97%), (9-phosphoethanolamine (PEA) and 2-amino-3-phosphonopropionic acid (APP) were obtained from Sigma (St. Louis, MO, U.S.A.). TV-methyl AEP was prepared by the method described by Kittredge,7) and the data for elemental analysis was as follows: Found: G, and three mackerels (Scomber japonicus) were freshly supplied from the fish market. The livers of five chickens, three pigs and two oxen freshly supplied from a local slaughterhouses were also used.…”

Section: Methodsmentioning

confidence: 99%

Determination of 2-aminoethylphosphonic acid and its N-methyl derivative in animal tissues by gas chromatography with flame photometric detection.

Kataoka

Sakiyama

Makita

1989

Agricultural and Biological Chemistry

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A sensitive and selective method was developed for the determination of 2-aminoethylphosphonic acid (AEP) and TV-methyl AEPin animal tissues by gas chromatography (GC). These compounds were converted into their N-isobutoxycarbonyl methyl ester derivatives and measured by GC with flame photometric detection (FPD-GC), using 0.5 % FFAP on Uniport HP as the GC column packing/The calibration curves for AEPand N-methyl AEPin the range of 0.02~2/ig were linear, and the detection limit was about 20 pg as an injection amount. AEPandTV-methyl AEPin animal tissues were found in the free form and bound form with lipid and other biological macromolecules, and they could be measured without any influence from coexistent substances by FPD-GC.The recoveries of AEPand /V-methyl AEPadded to the tissue samples were 92 -105 %, and their reproducibility was found to be satisfactory. Thedistribution of these compounds in various animals wasalso studied by using this new method.

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Isolation and Characterization of the N-Methyl Derivatives of 2-Aminoethylphosphonic Acid from the Sea Anemone, Anthopleura xanthogrammica^*

Cited by 63 publications

References 17 publications

Occurrence of Phosphonosphingolipids in Bdellovibrio bacteriovorus Strain UKi2

Occurrence of Phosphonosphingolipids in Bdellovibrio bacteriovorus Strain UKi2

The aminoethylphosphonate-containing lipids of rumen protozoa

Determination of 2-aminoethylphosphonic acid and its N-methyl derivative in animal tissues by gas chromatography with flame photometric detection.

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Isolation and Characterization of the N-Methyl Derivatives of 2-Aminoethylphosphonic Acid from the Sea Anemone, Anthopleura xanthogrammica*

Cited by 63 publications

References 17 publications

Occurrence of Phosphonosphingolipids in Bdellovibrio bacteriovorus Strain UKi2

Occurrence of Phosphonosphingolipids in Bdellovibrio bacteriovorus Strain UKi2

The aminoethylphosphonate-containing lipids of rumen protozoa

Determination of 2-aminoethylphosphonic acid and its N-methyl derivative in animal tissues by gas chromatography with flame photometric detection.

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Isolation and Characterization of the N-Methyl Derivatives of 2-Aminoethylphosphonic Acid from the Sea Anemone, Anthopleura xanthogrammica^*