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Miyamoto, Tomofumi; Yamamoto, Akira; Wakabayashi, Miho; Nagaregawa, Yoshiteru; Inagaki, Michio; Higuchi, Ryota; Iha, Masahiko; Teruya, Kiichiro

doi:10.1002/1099-0690(200006)2000:12<2295::aid-ejoc2295>3.3.co;2-y

Cited by 5 publications

(4 citation statements)

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“…Two additional gangliosides, acanthagan-gliosides I 833 and J 834 were obtained from an Okinawan specimen of the sea star Acanthaster planci. 569 Linckia laevigata from Vietnam contained a ganglioside 835 with an 8-O-methyl-N-glycylneurmic acid residue. 570 The same residue was found in less well defined gangliosides from the sea star Evasterias ecinosoma.…”

Section: Echinodermsmentioning

confidence: 99%

Marine natural products

2001

Nat. Prod. Rep.

400

128

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This review covers the marine natural products literature for the year 2000 and is organized phylogenetically, with sections on marine microorganisms and phytoplankton, green algae, brown algae, red algae, sponges, coelenterates, bryozoans, molluscs, tunicates. echinoderms and miscellaneous marine organisms. There is an emphasis on new structures, stressing their biological activities, source organisms and countries of origin, and also syntheses that confirm the structures of known compounds. The review contains 869 structures and 592 references, of which 434 appeared between January and December 2000.

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Section: Echinodermsmentioning

confidence: 99%

Marine natural products

2001

Nat. Prod. Rep.

400

128

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“…One is a unique pentasaccharide moiety containing synthetically challenging 1,2‐ cis glycosides, a 1,2‐ cis ‐α‐ d ‐galactosyl ( d ‐Gal) residue and two 1,2‐ cis ‐α‐ l ‐fucofuranosyl ( l ‐Fuc f ) residues, which is rare. Indeed, most fucosylated GSLs found in mammals and invertebrates possess a terminal l ‐fucose residue in the pyranose form in the glycon moiety of the molecule, and there are only a few examples of natural GSLs bearing l ‐Fuc f residues in the structure . For instance, the same group reported the isolation and characterization of diglycosylated GSL terpioside A ( 2 ) (Figure ) from the marine sponge Terpios sp.…”

Section: Figurementioning

confidence: 99%

Total Synthesis of Terpioside B

Inaba

Endo

Iibuchi

et al. 2020

Chemistry A European J

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The first total synthesis of terpioside B (1) has been accomplished. Key steps include the stereoselective installments of a set of challenging 1,2‐cis‐glycosidic linkages. Thus, α(1,4)‐linked d‐galactoside was effectively constructed from a 1,2‐anhydrogalactose donor and an unprotected 1,6‐anhydrogalactose acceptor by using a boron‐mediated aglycon delivery (BMAD) method. In addition, α‐l‐fucofuranosides were stereoselectively and simultaneously constructed by remote group‐assisted 1,2‐cis‐α‐stereoselective glycosylations.

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“…[1][2][3][4][5][6] In the study of the GSLs of the starfish Luidia maculata (yatsudesunahitode in Japanese), we reported on the isolation, structure and biological activities of cerebrosides, 7) ceramide lactosides, 8) sulfatide, 9) and gangliosides. 10,11) Continuing the previous studies, further isolation and characterization of the more polar ganglioside from L. maculata were conducted.…”

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Isolation and Structure of a GD3-Type Ganglioside Molecular Species Possessing Neuritogenic Activity from the Starfish Luidia maculata

et al. 2004

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In the course of our continuing research on biologically active glycosphingolipids (GSLs) from echinoderms, a series of studies on the isolation and structure elucidation of GSLs from starfish have been performed in our laboratory. [1][2][3][4][5][6] In the study of the GSLs of the starfish Luidia maculata (yatsudesunahitode in Japanese), we reported on the isolation, structure and biological activities of cerebrosides, 7) ceramide lactosides, 8) sulfatide, 9) and gangliosides. 10,11) Continuing the previous studies, further isolation and characterization of the more polar ganglioside from L. maculata were conducted. In this paper, we report on the isolation and structure of a ganglioside molecular species from the whole bodies of L. maculata. The biological activity of the ganglioside is also reported.The polar lipid fraction, which was obtained from the chloroform/methanol extract of the whole bodies of L. maculata, was subjected to repeated column chromatography to give a polar compound, designated LMG-4 (1), showing a single spot on silica gel thin-layer chromatography (TLC).Compound 1 shows strong hydroxy and amide absorptions in the IR spectrum and has a positive reaction against resorcinol reagent.12) The negative FAB-MS exhibits a series of quasimolecular ion peaks [MϪH] Ϫ at m/z: 1500-1620. Therefore 1 is suggested to be a molecular species of ganglioside.The structure of the ceramide moiety was examined first. When 1 was methanolyzed with methanolic hydrochloric acid, a mixture of fatty acid methyl esters (FAM) and longchain bases (LCBs) was obtained. The FAM mixture was analyzed by GC-MS, which revealed the presence of three components. These were characterized as methyl 2-hydroxydocosanoate (major), methyl 2-hydroxytricosanoate, and methyl 2-hydroxytetracosanoate. The LCB mixture was found to be composed of such phytosphingosines as 2-amino-1,3,4-trihydroxy-heptadecane (major), 2-amino-1,3,4-trihydroxy-octadecane, and 2-amino-1,3,4-trihydroxy-nonadecane, based on GC-MS analysis of its TMS derivative (Chart 1).The structure of the sugar moiety of 1 was established as follows. The GC analysis of hexitol acetate derivatives of the neutral sugars, which were obtained by hydrolysis, reduction,

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Cited by 5 publications

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Marine natural products

Marine natural products

Total Synthesis of Terpioside B

Isolation and Structure of a GD3-Type Ganglioside Molecular Species Possessing Neuritogenic Activity from the Starfish Luidia maculata

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