Two New Gangliosides, Acanthagangliosides I and J from the StarfishAcanthaster planci

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

doi:10.1002/1099-0690(200006)2000:12<2295::aid-ejoc2295>3.0.co;2-6

Cited by 25 publications

(3 citation statements)

References 7 publications

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“…New classes of gangliosides have been found in echinoderms, such as sea cucumbers [ 23 , 24 , 25 ], starfish [ 26 , 27 , 28 , 29 , 30 , 31 ], sea urchins [ 32 , 33 , 34 ], and feather stars [ 35 ], and many of these echinodermatous gangliosides (EGs) also exhibited neuritogenic activity, some of which exceeded that of mammalian GM1 [ 36 , 37 ]. In contrast to mammalian gangliosides, EGs contain partially modified sialic acid residues and their unique oligomers.…”

Section: Introductionmentioning

confidence: 99%

Structure-Activity Relationship Study of the Neuritogenic Potential of the Glycan of Starfish Ganglioside LLG-3 ‡

et al. 2015

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LLG-3 is a ganglioside isolated from the starfish Linchia laevigata. To clarify the structure-activity relationship of the glycan of LLG-3 toward rat pheochromocytoma PC12 cells in the presence of nerve growth factor, a series of mono- to tetrasaccharide glycan derivatives were chemically synthesized and evaluated in vitro. The methyl group at C8 of the terminal sialic acid residue was crucial for neuritogenic activity, and the terminal trisaccharide moiety was the minimum active motif. Furthermore, the trisaccharide also stimulated neuritogenesis in human neuroblastoma SH-SY5Y cells via mitogen-activated protein kinase (MAPK) signaling. Phosphorylation of extracellular signal-regulated kinase (ERK) 1/2 was rapidly induced by adding 1 or 10 nM of the trisaccharide. The ratio of phosphorylated ERK to ERK reached a maximum 5 min after stimulation, and then decreased gradually. However, the trisaccharide did not induce significant Akt phosphorylation. These effects were abolished by pretreatment with the MAPK inhibitor U0126, which inhibits enzymes MEK1 and MEK2. In addition, U0126 inhibited the phosphorylation of ERK 1/2 in response to the trisaccharide dose-dependently. Therefore, we concluded that the trisaccharide promotes neurite extension in SH-SY5Y cells via MAPK/ERK signaling, not Akt signaling.

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Section: Introductionmentioning

confidence: 99%

Structure-Activity Relationship Study of the Neuritogenic Potential of the Glycan of Starfish Ganglioside LLG-3 ‡

et al. 2015

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“… The structures of typical echinoderm cerebrosides (luidiacerebroside A ( 6 ) from the starfish Luidia maculata [ 155 ] and glucocerebroside HPC-3-A ( 7 ) from the sea cucumber Holothuria pervicax [ 156 ]) and gangliosides (ganglioside molecular species from the sea cucumber H. pervicax ( 8 ) [ 157 ] and acanthaganglioside I ( 9 ) from the starfish Acanthaster planci [ 158 ]). …”

Section: Figurementioning

confidence: 99%

Application of MS-Based Metabolomic Approaches in Analysis of Starfish and Sea Cucumber Bioactive Compounds

2022

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Today, marine natural products are considered one of the main sources of compounds for drug development. Starfish and sea cucumbers are potential sources of natural products of pharmaceutical interest. Among their metabolites, polar steroids, triterpene glycosides, and polar lipids have attracted a great deal of attention; however, studying these compounds by conventional methods is challenging. The application of modern MS-based approaches can help to obtain valuable information about such compounds. This review provides an up-to-date overview of MS-based applications for starfish and sea cucumber bioactive compounds analysis. While describing most characteristic features of MS-based approaches in the context of starfish and sea cucumber metabolites, including sample preparation and MS analysis steps, the present paper mainly focuses on the application of MS-based metabolic profiling of polar steroid compounds, triterpene glycosides, and lipids. The application of MS in metabolomics studies is also outlined.

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“…The ganglioside molecular species, AG-1, were obtained from the whole body of the starfish Acanthaster planci [70]. Enzymatic hydrolysis by endoglycoceramidase gave an oligosaccharide and ceramides, quantitatively.…”

Section: Class Asteroideamentioning

confidence: 99%

Sphingolipids of Asteroidea and Holothuroidea: Structures and Biological Activities

et al. 2021

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Sphingolipids are complex lipids widespread in nature as structural components of biomembranes. Commonly, the sphingolipids of marine organisms differ from those of terrestrial animals and plants. The gangliosides are the most complex sphingolipids characteristic of vertebrates that have been found in only the Echinodermata (echinoderms) phylum of invertebrates. Sphingolipids of the representatives of the Asteroidea and Holothuroidea classes are the most studied among all echinoderms. In this review, we have summarized the data on sphingolipids of these two classes of marine invertebrates over the past two decades. Recently established structures, properties, and peculiarities of biogenesis of ceramides, cerebrosides, and gangliosides from starfishes and holothurians are discussed. The purpose of this review is to provide the most complete information on the chemical structures, structural features, and biological activities of sphingolipids of the Asteroidea and Holothuroidea classes.

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Two New Gangliosides, Acanthagangliosides I and J from the StarfishAcanthaster planci

Cited by 25 publications

References 7 publications

Structure-Activity Relationship Study of the Neuritogenic Potential of the Glycan of Starfish Ganglioside LLG-3 ‡

Structure-Activity Relationship Study of the Neuritogenic Potential of the Glycan of Starfish Ganglioside LLG-3 ‡

Application of MS-Based Metabolomic Approaches in Analysis of Starfish and Sea Cucumber Bioactive Compounds

Sphingolipids of Asteroidea and Holothuroidea: Structures and Biological Activities

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