2006
DOI: 10.1248/cpb.54.1293
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Constituents of Holothuroidea, 18. Isolation and Structure of Biologically Active Disialo- and Trisialo-Gangliosides from the Sea Cucumber Cucumaria echinata

Abstract: In the course of 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][12][13][14] In the study of the GSLs of the sea cucumber Cucumaria echinata (gumi in Japanese), we reported the isolation and structure of glucocerebrosides 2,4) and monosialogangliosides.1) In a continuation of the preceding studies… Show more

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Cited by 20 publications
(16 citation statements)
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“…[1][2][3][4][5][6][7] Continuing the previous studies, three cerebroside molecular species (BAC-1, BAC-2 and BAC-3) was obtained from the less polar lipid fraction of CHCl 3 /MeOH extract of sea cucumber Bohadschia argus (Janomenamako in Japanese). The structures of BAC-1, BAC-2 and BAC-3 could be determined by hitherto reported chemical and spectroscopic methods 2,4,5) as the molecular species of typical types of glucocerebrosides, 2,4,5) namely, a sphingosine-type b-glucocerebroside possessing non-hydroxy fatty acid (BAC-1), a sphingosine-type b-glucocerebroside possessing 2-hydroxy fatty acid (BAC-2), and phytosphingosine-type b-glucocerebroside possessing 2-hydroxy fatty acid (BAC-3), respectively (data not shown), as revealed in Fig.…”
mentioning
confidence: 85%
“…[1][2][3][4][5][6][7] Continuing the previous studies, three cerebroside molecular species (BAC-1, BAC-2 and BAC-3) was obtained from the less polar lipid fraction of CHCl 3 /MeOH extract of sea cucumber Bohadschia argus (Janomenamako in Japanese). The structures of BAC-1, BAC-2 and BAC-3 could be determined by hitherto reported chemical and spectroscopic methods 2,4,5) as the molecular species of typical types of glucocerebrosides, 2,4,5) namely, a sphingosine-type b-glucocerebroside possessing non-hydroxy fatty acid (BAC-1), a sphingosine-type b-glucocerebroside possessing 2-hydroxy fatty acid (BAC-2), and phytosphingosine-type b-glucocerebroside possessing 2-hydroxy fatty acid (BAC-3), respectively (data not shown), as revealed in Fig.…”
mentioning
confidence: 85%
“…Additionally, on account of their significant pharmacological activity toward the rat pheochromocytoma cell line (Kisa et al, 2006;Yamada et al, 2000;Yamada et al, 2001), 6 ganglioside compounds were also deemed as "screened compounds" with perfect DL but low OB.…”
Section: Active Compound Screeningmentioning
confidence: 99%
“…We attempted to determine the absolute configuration (D or L) of the sialic acid residues in the gangliosides 3,4) from the sea cucumber Cucumaria echinata.…”
mentioning
confidence: 99%
“…Protection of the diol in the side chain of 3 with acetone afforded an isopropyridene derivative (4). Oxidation of 4 with NaIO 4 gave a dial derivative (5).…”
mentioning
confidence: 99%
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