Biochemistry of Shellfish Lipid

The aminoethylphosphonate-containing lipids of rumen protozoa

“…Its infrared spectrum showed typical amide peaks at 1545 and 1645cm.-1. It was identical with that of the published spectrum of ceramide ciliatine isolated from shellfish (Hori et al 1966) except that it had an additional or more prominent small peak at 1032 cm.-l. Since ceramide phosphorylethanolamine can be expected to give a similar infrared spectrum, further evidence was required.…”

“…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.…”

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

“…19 ) Inorganic phosphorus and N-methyl derivatives of 2-aminoethylphosphonic acid were not detected in the hydrolysate. As shown in the table, the analytical values estimated for the ceramide aminoethylphophonate agreed closely with the calculated values, except for sphingosine as well as longchain base-No Moverover, there is not a gross difference except for sphingosine between the present results and those by the method which had been previously reported by Hori et al 31 ) The results of gas chromatographic analysis of the fatty acid composition are shown in Table III. The fatty acid composition was very simple.…”

Isolation of ceramide phosphorylethanolamine from the blowfly Calliphora erythrocephala

“…and showed a ninhydrin-positive base that ran to the same position as a marker of sphingosine (RF 0.43), obtained by an equivalent hydrolysis of authentic sphingomyelin. The infrared spectrum of the new lipid was almost identical with one published for the analogous ceramide aminoethylphosphonate (Hori et al 1966), showing characteristic amide peaks at 545 and 1645 cm.-1. However, there is a much more prominent peak at 1030 cm.-1, which is to be expected since it is characteristic of P-O-C bonds (Bellamy, 1958), of which ceramide phosphorylethanolamine contains 2/mol.…”

“…(Received 26 October 1967) The phospholipid ceramide aminoethylphosphonate has been characterized as a constituent of marine organisms (Hori, Itasaka & Inoue, 1966;Simon & Rouser, 1967). Recently we have isolated from rumen protozoa an amino sphingolipid fraction that was shown to be a mixture of ceramide aminoethylphosphonate and an analogue of sphingomyelin, ceramide phosphorylethanolamine (Dawson & Kemp, 1967).…”