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Studies on the Glycosphingolipids of the Starfish, Asterina Pectinifera III

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Studies on the Glycosphingolipids of the Starfish, Asterina Pectinifera III J. Biochem. 86, 765-772 (1979) Studies on the Glycosphingolipids of the Starfish , Asterina pectinifera1 ‡V. Isolation and Structural Studies of Two Novel Gangliosides Containing Internal Sialic Acid Residues Mutsumi SUGITA Department of Chemistry, Faculty of Liberal Arts and Education, Shiga University, Otsu, Shiga 520 Received for publication, March 30, 1979 Two gangliosides, provisionally named Gangliosides ‡T and 2 in previous studies, were isolated from starfish, Asterina pectinifera by silicic acid, DEAE-Sephadex, and Iatrobeads column chromatography procedures, and preparative thin-layer chromatography, and their structures were established. On the basis of the results of partial acid hydrolysis, methylation and oxidation with chromium trioxide, Gangliosides 1 and 2 were proposed to be ArapƒÀ(16)- GalpƒÀ(1 4)8-O-McNeuGc(2 3)GalpƒÀ(1 4)GlcpƒÀ(11)-ceramide and ArapƒÀ(16)- GalpƒÀ(14)NeuGc(23)GalpƒÀ(1 4)GlcpƒÀ(11)-ceramide, respectively. The ceramide moieties of both gangliosides had similar phytosphingosine and 2-hydroxy fatty acid compositions, and both gangliosides were structurally related to the previously described Ganglioside 3. In studies on the composition of glycosphingolipids as Araf,p(16)GalpƒÀ(14)[GalpƒÀ(18)]Neu- of the starfish, a new class of ganglioside which Gc(23)Galp,ƒÀ(14)GlcpƒÀ(11)-ceramide (2). contains internal sialic acid residues in its sugar This paper reports studies on the chemical chain has been found in Asterina pectinifera (1). structures of the two gangliosides with the highest The ganglioside fraction of the starfish was sepa (Ganglioside 1) and the intermediate (Ganglioside rated into at least three components by thin-layer 2) rates of migration on thin-layer chromatog chromatography. The slowest migrating com raphy. ponent, tentatively termed Ganglioside 3, was the most abundant, and its structure was characterized MATERIALS AND METHODS 1 This study was supported in part by a grant from the General-The type of starfish used as a Ministry of Education, Science and Culture of Japan. source of gangliosides, A. pectinifera, was essen For part 11 of this series, see Ref. (2). tially the same as in the previous study (2). Methods Abbreviations: Ara, arabinose; Gal, galactose; Glc, of thin-layer chromatography, paper chromatog glucose; NeuAc, N-acetylneuraminic acid; NeuGc, N- raphy, gas-liquid chromatography, and gas chro glycolylneuraminic acid; 8-O-MeNeuGc, 8-0-methyl- N-glycolylneuraminic acid; CMH, ceramide mono matograph-mass spectrometry were also essen hexoside; CDH, ceramide dihexoside. tially as described previously (2). Hexose content Vol. 86, No. 3, 1979 765 766 M. SUGITA was determined by the anthrone method (3) and (yield, 250 mg), was isolated at this column frac pentose by the method of Dische and Borenfreund tionation step and its structure has been established (4). Sialic acid was estimated by Svennerholm's (2). For the isolation of Gangliosides 1 and 2, resorcinol method (5). preparative thin-layer chromatography was em Isolation and Purification of Gangliosides 1 ployed; Gangliosides 1 and 2 were obtained in pure and 2-The isolation procedure consisted of form in yields of 35 mg and 80 mg, respectively extraction with a mixture of chloroform and (Fig. 1). methanol, Folch partition, and separation of gan The infrared spectra of Gangliosides 1 and 2 gliosides from the upper phase, using three types showed strong acid amide bond absorptions at of column chromatography successively, as de 1540 and 1645 cm 1, and a free hydroxy group scribed earlier (2). Final purification to obtain at 3300 cm 1, but no absorption at 1730 cm-1 single components was achieved by preparative due to ester carbonyl. thin-layer chromatography as follows. The Sugar Compositions of Gangliosides ‡T and 2- gangliosides obtained by column chromatography Gas-liquid chromatography of the N-acetyl-O- were applied (approximately 5 to 10 mg per plate) trimethylsilyl ether derivatives of the methyl to Silica gel H thin-layer plates (2.5 mM thick, glycosides which were obtained from the individual 20•~20 cm, Nakarai Chemical Co., Kyoto). The components of Gangliosides 1 and 2 revealed the plates were developed in 1-propanol-2.5 M ammonia presence of arabinose, glucose, galactose, and (7 : 3, v/v). The gangliosides contained in the sialic acid (or 8-O-methylsialic acid) in a molar silica gel scrapings were each extracted with chloroform-methanol-water (40 :60 : 10, by vol.). Partial Acid Hydrolysis of Gangliosides- Partial acid hydrolysis of ganglioside was per formed in 0.1 M HC1 for 90 min at 80•Ž. The hydrolysates were partitioned by the addition of chloroform and methanol to give a final solvent mixture of chloroform-methanol-water (10 : 5 :3, by vol.) which separated into a lower organic phase and an upper aqueous methanolic phase. The glycolipid fragments in the organic phase were identified by comparison of their migration on Merck plates (Silica gel 60, E. Merck, Darms tadt) with the migration of ceramide hexoside isolated previously (6), as well as by gas-liquid chromatography. The aqueous methanolic phase Fig. 1. Thin-layer chromatogram on silica gel of the was evaporated to dryness and the residual mate gangliosides isolated from the lipid extract of the starfish, rial was subjected to Dowex 1•~8 (acetate form, A. pectinifera. Solvent systems: (A) 1-propanol-2.5 M 200 to 400 mesh) column chromatography by the ammonia (7 :3, v/v) and (B) chloroform-methanol- method of Hoshino et al. (7). water (60 : 25 : 4, by vol.). Detection with: (A) re sorcinol and (B) orcinol-sulfuric acid spray reagents. 1, Ganglioside fraction obtained by partition, dialysis, RESULTS AND DISCUSSION and Mallinckrodt silicic acid and DEAE-Sephadex Extraction with a mixture of chloroform and column chromatographies from total lipid extract of methanol followed by Folch partition yielded A. pectinifera. 2 and 3, Gangliosides ‡T and 2 (the sub stances described in this paper) isolated by Iatrobeads 5.6 g of a crude ganglioside fraction, starting from column chromatography and preparative thin-layer 7 kg of the starfish, A. pectinifera. The crude chromatography. 4, Ganglioside 3 (2). 5 and 6, ganglioside fraction was subjected to three types Neutral glycosphingolipids derived from Gangliosides of column fractionation. Three gangliosides, 1 and 2 by partial acid hydrolysis. 7, Authentic provisionally named Gangliosides 1, 2, and 3, were ceramide glucoside (upper) and ceramide lactoside detected. The most abundant, Ganglioside 3 (lower) isolated from A. pectinifera (6). J. Biochem. GANGLIOSIDES OF STARFISH 767 ratio of approximately 1 : 1 : 2 : 1 (Fig. 2). Table side was butanolyzed and analyzed as described I shows the results of chemical analysis of Gan previously (2); each was found to consist ex gliosides ‡T and 2. For the determination of acetyl clusively of N-glycolylneuraminic acid. or glycolyl residues of sialic acids, each ganglio- Presence of 8-O-Methyl Sialic Acid in Gan glioside 1-To confirm the structure of sialic acids in Gangliosides ‡T and 2, Peaks 4 and 5 of Fig. 2 were analyzed by gas chromatography-mass spectrometry. The mass spectrum of Peak 5, shown in Fig. 3B, was identical with that of the trimethylsilyl ether (N-acetyl) derivative of the methyl ester methyl glycoside of N-acetylneuraminic acid (8). In the spectrum of Peak 4 (Fig. 3A), peaks at m/e 552 (M-15) (cf. m/e 610 for the N- acetylneuraminic acid derivative), at m/e 508 (M-59) (cf. m/e 566), at m/e 315 (M-CH2OTMS- TMSOH-NH5Ac) (cf. m/e 373), and at m/e 284 (M-CH2OTMS-2TMSOH) (cf. m/e 342) were observed. The mass difference of 58 m.u. indicates that the sialic acid (Peak 4) in Ganglioside 1 con tains an 0-methyl group instead of an O-tri- methylsilyl group. Next, to determine the position of the 0- methyl substituent in the sialic acid residues, Ganglioside 1 was subjected to methanolysis in 1.0 tit methanolic HCl for 17 h at 75•Ž. The resulting methyl glycosides were peracetylated in Fig. 2. Gas chromatograms of trimethylsilyl ether pyridine-acetic anhydride (3 : 2, v/v) for 12 h at (N-acetyl) derivatives of the individual sugar components room temperature, then the peracetylated deriva of Gangliosides 1 (A) and 2 (B). 1, Arabinose; 2, tives were analyzed by gas chromatography-mass galactose; 3, glucose; 4, 8-O-methyl-N-acetylneuraminic acid (the occurrence of this form of sialic acid in starfish spectrometry. Figure 4 shows the mass spectrum gangliosides is described in the text); 5, N-acetyl- of the peracetylated derivative of the methyl ester neuraminic acid. These analyses were performed on methyl glycoside of sialic acid obtained from a column of 3% OV-1. The column temperature was Ganelioside 1. This mass spectrum shows an programmed from 140•Ž to 230•Ž at 2•Ž/min. TABLE I. Chemical analysis of Gangliosides 1 and 2 isolated from the starfish, A. pectinifera. a The theoretical percent composition was calculated for a molecule containing 2-hydroxy-C22:0 acid and Cl7- phytosphingosine. b Resorcinol assay value as N-glycolylneuraminic acid. c Anthrone assay value as a mixture of glucose and galactose, 1 : 2. d As arabinose. Vol. 86, No. 3, 1979 768 M. SUGITA Fig. 3. Gas chromatograph-mass spectrometric patterns of the N-acetyl-trimethylsilylated methyl ester methyl glycosides of the sialic acids from Gangliosides 1 (A) and 2 (B). (A) and (B) correspond to Peaks 4 and 5 in Fig. 2, respectively. Analysis was performed on an LKB 9000 instrument. The intense and important peak at m/e 117 corre sponds to the fragment CH2OAcCHOCH3, which is evidently formed by cleavage between C-7 and C-8, and suggests that the 0-methyl group must be attached to C-8 (9). Studies of the distribution in nature of sialic acids have thus far disclosed the presence of 8-O-methyl sialic acids (N-glycolyl- or N-acetyl- neuraminic acids) only in starfish (9, 10).
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