Constituents of Crinoidea. 2. Isolation and Structure of the Novel Type Gangliosides from the Feather Star Comanthus japonica.

Abstract

Two novel type gangliosides CJP2 and CJP3 have been obtained from the feather star Comanthus japonica. On the basis of methylation linkage analysis combined with ammonolysis and other chemical and spectroscopic evidence, the chemical structures of CJP2 and CJP3 were determined to be a a-9-O-Me-NeuGc-(2→3)-inositolphosphoceramide and a a-9-O-Me-NeuGc-(2→11)-a a-9-O-Me-NeuGc-(2→3)-inositolphosphoceramide, respectively. These gangliosides are unique in that they are inositolphosphoceramide derivatives possessing sialic acid; such gangliosides have not previously been identified. The presence of 9-O-methyl-N-glycolyl-neuraminosyl residues is also unique in naturally occurring gangliosides.

Constituents of Crinoidea. 3. Isolation and Structure of a Glycosyl Inositolphosphoceramide-Type Ganglioside with Neuritogenic Activity from the Feather Star Comanthus japonica

“…NMR spectra were recorded on a Varian Unity-500 spectrometer ( Separation of CJP4 For the extraction and fractionation of the crude ganglioside fraction from the whole bodies of the feather star C. japonica (7.6 kg), the preceding paper should be referred to. 8 Fig. 2).…”

“…[1][2][3][4][5][6] In the study of the GSLs of the feather star Comanthus japonica (Nipponumishida in Japanese), we reported on the isolation and structural elucidation of inositolphosphoceramide, CJP1, 7) and the glycosyl inositolphosphoceramide-type gangliosides CJP2 and CJP3. 8) Continuing the preceding studies, further isolation and characterization of the more polar ganglioside from C. japonica was conducted. In this paper, we report on the isolation and structure of a glycosyl inositolphosphoceramide-type ganglioside from the whole bodies of C. japonica.…”

“…When CJP4 was hydrolyzed with 5% acetic acid, CJP1, L-myo-inositol-1-O-phosphoceramide, was obtained. In the previous papers, 7,8) CJP1 was described as D-myo-by misreading the value of the specific rotation of the reference compound. It is corrected to L-myo-in this paper.…”

“…S-3 was identified as 2,4,5,6-tetramethylated myo-inositol by comparison of its 1 H-NMR spectrum with that of the myo-inositol derivative prepared from CJP2. 8) Consequently, the trisialoyl residue must be linked at the C3-OH group of the inositol part, as shown in Fig. 1.…”

Constituents of Crinoidea. 5. Isolation and Structure of a New Glycosyl Inositolphosphoceramide-Type Ganglioside from the Feather Star Comanthina schlegeli

“…[1][2][3] In the study of the GSLs of the crinoidea, we reported on the isolation and structural elucidation of cerebrosides, 4) inositolphosphoceramide, 5) and the glycosyl inositolphosphoceramide-type gangliosides 6,7) from the feather star Comanthus japonica. Continuing the preceding studies, isolation and characterization of GSLs from the feather star Comanthina schlegeli (Hanaumishida in Japanese) was conducted.…”