Terpioside from the Marine Sponge <i>Terpios</i> sp., the First Glycosphingolipid Having an <scp>L</scp>‐Fucofuranose Unit

Costantino, Valeria; Fattorusso, Ernesto; Imperatore, Concetta; Mangoni, Alfonso; Teta, Roberta

doi:10.1002/ejoc.200701220

Cited by 20 publications

(17 citation statements)

References 9 publications

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“…3-HQA in cluster (c) is found in several bisintercalator natural products of marine origin (such as thiocoraline, triostin, SW-163 and echinomycin/quinomycin) [ 28 ], as one of the two key chromophores (together with quinoxalinic acid) for binding to duplex DNA by insertion between the bases to allow proper placement of the peptidic core into the DNA minor groove [ 29 ]. Phosphatidylethanolamine (PE) in cluster (d) belongs to the family of phospholipids and glycolipids that are the main constituents of sponge cell membranes [ 30 , 31 ], and have been shown to possess immune-modulating and antitumor activity [ 32 , 33 ].…”

Section: Discussionmentioning

confidence: 99%

Evaluating the Effects of an Organic Extract from the Mediterranean Sponge Geodia cydonium on Human Breast Cancer Cell Lines

Costantini

Guerriero

Teta

et al. 2017

IJMS

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Abstract:Marine sponges are an excellent source of bioactive secondary metabolites for pharmacological applications. In the present study, we evaluated the chemistry, cytotoxicity and metabolomics of an organic extract from the Mediterranean marine sponge Geodia cydonium, collected in coastal waters of the Gulf of Naples. We identified an active fraction able to block proliferation of breast cancer cell lines MCF-7, MDA-MB231, and MDA-MB468 and to induce cellular apoptosis, whereas it was inactive on normal breast cells (MCF-10A). Metabolomic studies showed that this active fraction was able to interfere with amino acid metabolism, as well as to modulate glycolysis and glycosphingolipid metabolic pathways. In addition, the evaluation of the cytokinome profile on the polar fractions of three treated breast cancer cell lines (compared to untreated cells) demonstrated that this fraction induced a slight anti-inflammatory effect. Finally, the chemical entities present in this fraction were analyzed by liquid chromatography high resolution mass spectrometry combined with molecular networking.

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Section: Discussionmentioning

confidence: 99%

Evaluating the Effects of an Organic Extract from the Mediterranean Sponge Geodia cydonium on Human Breast Cancer Cell Lines

Costantini

Guerriero

Teta

et al. 2017

IJMS

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“…HR-MS (ESI, negative ion mode): calcd. for C 6 -565.0472; found 565.0470. Analytical data are in accordance with literature data.…”

Section: Ammonium 6-deoxy-6-fluoro-d-galactofuranosyl 1-phosphate (8)mentioning

confidence: 93%

Stereoselective Chemoenzymatic Synthesis of UDP‐1,2‐cis‐furanoses from α,β‐Furanosyl 1‐Phosphates

Peltier¹,

Guégan²,

Daniellou³

et al. 2008

Eur J Org Chem

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The biosynthesis of furanosyl‐containing glycoconjugates is poorly described, mainly due to the lack of UDP‐furanoses. Here we present our effort to synthesize rare nucleotide‐sugars with the aid of a multiple‐enzyme system, notably including galactose‐1‐phosphate uridylyltransferase. Firstly, STD‐NMR techniques were used to probe the broad substrate specificity of this particular enzyme. The chemical synthesis of the needed furanosyl 1‐phosphate starting materials was then performed with unprotected thioimidoyl donors. This led to the first stereoselective chemoenzymatic syntheses of UDP‐β‐L‐arabinofuranose, UDP‐α‐D‐fucofuranose and UDP‐α‐D‐6F‐galactofuranose from starting mixtures of sugar‐phosphates.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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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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Terpioside from the Marine Sponge Terpios sp., the First Glycosphingolipid Having an L‐Fucofuranose Unit

Cited by 20 publications

References 9 publications

Evaluating the Effects of an Organic Extract from the Mediterranean Sponge Geodia cydonium on Human Breast Cancer Cell Lines

Evaluating the Effects of an Organic Extract from the Mediterranean Sponge Geodia cydonium on Human Breast Cancer Cell Lines

Stereoselective Chemoenzymatic Synthesis of UDP‐1,2‐cis‐furanoses from α,β‐Furanosyl 1‐Phosphates

Total Synthesis of Terpioside B

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