Glycolipids from Marine Invertebrates

Barnathan, Gilles; Couzinet‐Mossion, Aurélie; Wielgosz‐Collin, Gaëtane

doi:10.1002/9783527681501.ch05

Cited by 7 publications

(4 citation statements)

References 213 publications

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“…In the field of natural product chemistry, the marine environment has proven to be a rich source of structurally diverse and biologically active compounds including glycolipids. − In 2011, Wojnar and Northcote described the isolation of agminosides A–E (Figure ), a group of structurally related, complex, and unusual glycolipids, from the marine sponge Raspailia agminata. , Sponge specimens of R. agminata were collected by hand from Taheke Reef in the Cavalli Islands, New Zealand.…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of a Chimeric Glycolipid Bearing the Partially Acetylated Backbone of Sponge-Derived Agminoside E

et al. 2021

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We describe the total synthesis of a chimeric glycolipid bearing both the partially acetylated backbone of spongederived agminoside E and the (R)-3-hydroxydecanoic acid chain of bacterial rhamnolipids. The branched pentaglucolipid skeleton was achieved using a [3 + 2] disconnection approach. The β-(1 → 2) and β-(1 → 4)-glycosidic bonds were synthesized through a combination of NIS/Yb(OTf) 3 -and TMSOTf-mediated stereoselective glycosylations of thiotolyl, N-phenyltrifluoroacetimidate, and trichloroacetimidate donors. Late-stage pentaacetylation, Staudinger reduction of a (2-azidomethyl)benzoyl group, followed by continuous-flow microfluidic hydrogenolysis completed the total synthesis of the structurally simplified glycolipid, whose partial acetylation pattern on the glycan part was identical to agminoside E. Our study lays the foundation for the total synthesis of spongederived agminosides and the understanding of their biological functions in sponges.

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Section: Introductionmentioning

confidence: 99%

Total Synthesis of a Chimeric Glycolipid Bearing the Partially Acetylated Backbone of Sponge-Derived Agminoside E

et al. 2021

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“…Given the biological relevance and structural complexity of these classes of compounds, a large number of reviews [ 6 , 7 , 8 , 9 , 10 , 11 , 12 ], books, and book chapters [ 13 , 14 , 15 ] have been devoted to all aspects related to their chemistry and biology. More specifically, in the field of glycolipids of marine origin, several excellent reviews have been published, especially by Barnathan et al [ 16 ], which represents an excellent description of all the glycolipids found in marine invertebrates, as well as by Li et al [ 17 ], which focused on the chemistry and biology of glycoglycerolipids from marine organisms. In addition, numerous reviews have been reported on very specific compounds, such as KRN7000 [ 18 ] and related glycosphingolipids [ 19 ] due to their outstanding biological activities and their potential pharmacological activity.…”

Section: Introductionmentioning

confidence: 99%

Chemistry and Biology of Bioactive Glycolipids of Marine Origin

Cheng-Sánchez

Sarabia

2018

Marine Drugs

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Glycolipids represent a broad class of natural products structurally featured by a glycosidic fragment linked to a lipidic molecule. Despite the large structural variety of these glycoconjugates, they can be classified into three main groups, i.e., glycosphingolipids, glycoglycerolipids, and atypical glycolipids. In the particular case of glycolipids derived from marine sources, an impressive variety in their structural features and biological properties is observed, thus making them prime targets for chemical synthesis. In the present review, we explore the chemistry and biology of this class of compounds.

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“…Glycolipids belong to the broad class of glycoconjugates and are characterized by having one or more monosaccharide residues linked by a glycosidic bond to a hydrophobic moiety, such as an acylglycerol, a sphingoid, or a prenyl phosphate [1]. Glycolipids, including glycosphingolipids and gangliosides, are widely found in marine invertebrates, especially in echinoderms (sea stars, sea cucumbers) and sponges, and show a large variety of biological activities such as antitumor, immunomodulatory and nitric oxide release-inhibiting activities [2]. …”

Section: Introductionmentioning

confidence: 99%

Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiens

et al. 2016

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Among marine organisms, sponges are the richest sources of pharmacologically-active compounds. Stemming from a previous lead discovery program that gathered a comprehensive library of organic extracts of marine sponges from the off-shore region of Portugal, crude extracts of Erylus cf. deficiens collected in the Gorringe Bank (Atlantic Ocean) were tested in the innovative high throughput screening (HTS) assay for inhibitors of indoleamine 2,3-dioxygenase (IDO) and showed activity. Bioassay guided fractionation of the dichloromethane extract led to the isolation of four new glycolipids, named erylusamide A–D. The structures of the isolated compounds were established by 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) and chemical derivatization. The metabolites shared a pentasaccharide moiety constituted by unusual highly acetylated d-glucose moieties as well as d-xylose and d-galactose. The aglycones were unprecedented long chain dihydroxyketo amides. Erylusamides A, B and D differ in the length of the hydrocarbon chain, while erylusamide C is a structural isomer of erylusamide B.

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Glycolipids from Marine Invertebrates

Abstract: Glycolipids constitute a broad class of natural compounds belonging to the glycoconjugates.

Cited by 7 publications

References 213 publications

Total Synthesis of a Chimeric Glycolipid Bearing the Partially Acetylated Backbone of Sponge-Derived Agminoside E

Total Synthesis of a Chimeric Glycolipid Bearing the Partially Acetylated Backbone of Sponge-Derived Agminoside E

Chemistry and Biology of Bioactive Glycolipids of Marine Origin

Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiens

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