Isolation and Structure of Biologically Active Gangliosides from the Sea CucumberHolothuria pervicax

Yamada, Koji; Harada, Yasuo; Nagaregawa, Yoshiteru; Miyamoto, Tomofumi; Isobe, Ryuichi; Higuchi, Ryota

doi:10.1002/(sici)1099-0690(199811)1998:11<2519::aid-ejoc2519>3.0.co;2-v

Cited by 32 publications

(18 citation statements)

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“…[2][3][4][5][6][7][8][9][10][11] In the study of the GSLs of the sea cucumber Holothuria pervicax, we reported the isolation and structure of ten glucocerebrosides revealing a very close resemblance in structure.9) However, all these compounds still exist as a mixture of regio-isomers for terminal methyl groups in the side chain of the long-chain base (LCB) moiety, namely a mixture of iso and ante-iso isomers as shown in Fig. 1.…”

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Constituents of Holothuroidea, 15. Isolation of Ante-iso Type Regio-isomer on Long Chain Base Moiety of Glucocerebroside from the Sea Cucumber Holothuria leucospilota

Yamada

Wada

Onaka

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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In our continuing research on biologically active glycosphingolipids (GSLs) from echinoderms, a series of studies on the isolation and structural elucidation of the GSLs from sea cucumber species have been performed in our laboratory. [2][3][4][5][6][7][8][9][10][11] In the study of the GSLs of the sea cucumber Holothuria pervicax, we reported the isolation and structure of ten glucocerebrosides revealing a very close resemblance in structure.9) However, all these compounds still exist as a mixture of regio-isomers for terminal methyl groups in the side chain of the long-chain base (LCB) moiety, namely a mixture of iso and ante-iso isomers as shown in Fig. 1. Continuing the previous studies, the separation of the mixture of the regio-isomers was conducted. In this paper, we report on the isolation of an ante-iso type regio-isomer of glucocerebroside from its parent glucocerebroside molecular species HLC-2, an abundant compound obtained from the whole bodies of the sea cucumber Holothuria leucospilota (Nisekuronamako in Japanese). 12)The less polar lipid fraction, which was obtained from the chloroform/methanol extract of the whole bodies of H. leucospilota, was subjected to repeated silica gel column chromatography to give three cerebroside molecular species, HLC-1, HLC-2, and HLC-3, each showing a single spot on silica gel thin-layer chromatography (TLC).In the IR and positive-ion FAB mass spectra of HLC-1, HLC-2, and HLC-3, strong hydroxy and amide absorptions and a series of molecular ion peaks are observed. Their 13 C-NMR spectra (Fig. 1, Table 1) exhibit the characteristic signals of a sphingosine-type b-glucocerebroside possessing an unsubstituted fatty acid (HLC-1), a sphingosine-type b-glucocerebroside possessing a 2-hydroxy fatty acid (HLC-2), and a phytosphingosine-type b-glucocerebroside possessing a 2-hydroxy fatty acid (HLC-3), respectively. Therefore, they are suggested to be the molecular species of three typical types of glucocerebrosides. Their structures shown in Fig. 1 were characterized by comparison of their 13 C-NMR spectral data with those of known glucocerebrosides 2-4) hitherto obtained, and by means of the results of their chemical degradations, namely methanolysis followed by the GC-MS analysis of the methanolysis products, fatty acid methyl ester (FAM), and LCB, as shown in Fig. 2 and Experimental. The geometry (Z) of the double bond in the unsaturated fatty acyl moiety of HLC-1-HLC-3 was determined from the d value (27.4, 27.5) of the allylic carbon atoms obtained from their 1 H-detected heteronuclear multiple-bond connectivity (HMBC) spectra (Fig. 3) ; 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan: and b Department of Medical Electronics Engineering, Faculty of Engineering, Towa University; 1-1-1 Chikusigaoka, Minamiku, Fukuoka 815-0036, Japan. Received February 14, 2005; accepted March 22, 2005 An ante-iso type regio-isomer on the long chain base moiety of a glucocerebroside, HLC-2-A, has been isolated from its parent glucocerebroside molecular species HLC-2 composed of ...

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Constituents of Holothuroidea, 15. Isolation of Ante-iso Type Regio-isomer on Long Chain Base Moiety of Glucocerebroside from the Sea Cucumber Holothuria leucospilota

Yamada

Wada

Onaka

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…[2][3][4][5][6][7][8] In the study of the GSLs of the sea cucumber Holothuria pervicax (Torafunamako in Japanese), we reported the isolation and structure of four new ganglioside molecular species. 5,7) Continuing the preceding studies, the isolation and characterization of cerebrosides from H. pervicax was conducted. In this paper, we report the isolation and characterization of glucocerebrosides from the whole bodies of H. pervicax.…”

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“…5,7) Continuing the preceding studies, the isolation and characterization of cerebrosides from H. pervicax was conducted. In this paper, we report the isolation and characterization of glucocerebrosides from the whole bodies of H. pervicax.…”

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Constituents of Holothuroidea. 12. Isolation and Structure of Glucocerebrosides from the Sea Cucumber Holothuria pervicax.

Yamada

Sasaki

Harada

et al. 2002

CHEMICAL & PHARMACEUTICAL BULLETIN

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In our continuing research on biologically active glycosphingolipids (GSLs) from echinoderms, a series of studies on the isolation and structural elucidation of the GSLs from sea cucumber species have been performed in our laboratory. [2][3][4][5][6][7][8] In the study of the GSLs of the sea cucumber Holothuria pervicax (Torafunamako in Japanese), we reported the isolation and structure of four new ganglioside molecular species. 5,7) Continuing the preceding studies, the isolation and characterization of cerebrosides from H. pervicax was conducted. In this paper, we report the isolation and characterization of glucocerebrosides from the whole bodies of H. pervicax.The less polar lipid fraction, which was obtained from the chloroform/methanol extract of the whole bodies of H. pervicax, was subjected to repeated silica gel column chromatography to give three cerebroside molecular species, HPC-1, HPC-2, and HPC-3, each showing a single spot on silica gel thin-layer chromatography (TLC).HPC-1, HPC-2, and HPC-3 exhibit strong hydroxy and amide absorptions in their IR spectra, and a series of molecular ion peaks in their positive FAB mass spectra, respectively. In their 13 C-NMR spectra (Fig. 1, Table 1), they reveal characteristic signals of a sphingosine-type b-glucocerebroside possessing an unsubstituted fatty acid (HPC-1), a sphingosine-type b-glucocerebroside possessing a 2-hydroxy fatty acid (HPC-2), and a phytosphingosine-type b-glucocerebroside possessing a 2-hydroxy fatty acid (HPC-3), respectively. Therefore, they are suggested to be the molecular species of three typical types of glucocerebrosides. Their structures shown in Fig. 1 were characterized by comparison of their 13 C-NMR spectral data with those of known glucocerebrosides 2-4) hitherto obtained, and by means of the results of their chemical degradations, namely methanolysis followed by the GC-MS analysis of the methanolysis products, fatty acid methyl ester (FAM) and long-chain base (LCB), as shown in Fig. 2 and the Experimental section. The absolute configuration of their glucose moiety (D-form) was determined by the Hara method 9) (Experimental section). Based on the considerable interest in and importance of determining the molecular species composition of GSLs, the isolation and structural elucidation of glucocerebroside components in the most polar molecular species, HPC-3, was conducted at this time. HPC-3 could be separated by reversed-phase HPLC into eighteen peaks (Fig. 3a), and could be recovered to give six fractions, 5, 8, 9, 11, 14 and 16. They behaved as pure compounds in HPLC. However, fractions 11, 14 and 16 were still regarded as heterogeneous compounds, respectively, since they afforded plural FAMs upon methanolysis. Each fraction, 11, 14 and 16, was successively separated into plural peaks by using recycling reversed-phase (C30) HPLC, and seven fractions could be isolated as shown in Fig. 3b and c. Thus, ten components, designated as HPC-3-A-HPC-3-J, were obtained from the parent glucocerebroside mixture, HPC-3. In the negative ...

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“…[2][3][4][5][6][7] Continuing the previous studies, our search for the biologically active ganglioside from the sea cucumber Stichopus chloronotus (shikakunamako in Japanese) has led to the isolation of three ganglioside molecular species designated SCG-1, SCG-2, and SCG-3. In this paper, we report on the isolation and characterization of these three gangliosides from the body walls of S. chloronotus.…”

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“…5,13) In addition, the absolute configuration of the Glc unit was verified to be the D-form using the Hara et al method. 14) Consequently, if NeuGc, which is commonly found in natural sources, is assumed to be of the D-series, then SCG-1 is the (N-glycolyl-a -D-neuraminosyl)-(2→6)-b -D-glucopyranoside of a ceramide composed of heterogeneous (2S,3R,4E)-sphingosine and (2R)-2-hydroxy fatty acid units.…”

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Constituents of Holothuroidea, 13. Structure of Neuritogenic Active Ganglioside Molecular Species from the Sea Cucumber Stichopus chloronotus.

et al. 2003

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Three ganglioside molecular species, SCG-1, SCG-2, and SCG-3, were obtained from the lipid fraction of the chloroform-methanol extract of the sea cucumber Stichopus chloronotus. On the basis of chemical and spectroscopic evidence, the structures of these gangliosides have been determined to be 1 -2), and 1-O-[a a -L-fucopyranosyl-(1→11)-(N-glycolyl-a a -D-neuraminosyl)-(2→6)-b b-D-glucopyranosyl]-ceramide (SCG-3). The ceramide moieties were composed of heterogeneous long-chain base and fatty acid units. SCG-3 is the first type of ganglioside containing a fucopyranose in the sialosyl trisaccharide moiety. Moreover, these three gangliosides exhibited neuritogenic activity toward the rat pheochromocytoma PC12 cells in the presence of nerve growth factor.

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Isolation and Structure of Biologically Active Gangliosides from the Sea CucumberHolothuria pervicax

Cited by 32 publications

References 9 publications

Constituents of Holothuroidea, 15. Isolation of Ante-iso Type Regio-isomer on Long Chain Base Moiety of Glucocerebroside from the Sea Cucumber Holothuria leucospilota

Constituents of Holothuroidea, 15. Isolation of Ante-iso Type Regio-isomer on Long Chain Base Moiety of Glucocerebroside from the Sea Cucumber Holothuria leucospilota

Constituents of Holothuroidea. 12. Isolation and Structure of Glucocerebrosides from the Sea Cucumber Holothuria pervicax.

Constituents of Holothuroidea, 13. Structure of Neuritogenic Active Ganglioside Molecular Species from the Sea Cucumber Stichopus chloronotus.

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