Zeamide, a Glycosylinositol Phosphorylceramide with the Novel Core Arap(1β→6)Ins Motif from the Marine Sponge Svenzea zeai

Glycosylinositol phosphorylceramides (GIPCs) show a great structural diversity, but all share a small number of core structures, with a glucosamine, a mannose, or a glucuronic acid as the first sugar linked to the inositol. The Caribbean sponge Svenzea zeai was shown to consistently contain zeamide...

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Autores principales: Della Sala, Gerardo, Teta, Roberta, Esposito, Germana, Pawlik, Joseph R., Mangoni, Alfonso, Costantino, Valeria
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6151786/
https://www.ncbi.nlm.nih.gov/pubmed/28862696
http://dx.doi.org/10.3390/molecules22091455
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author Della Sala, Gerardo
Teta, Roberta
Esposito, Germana
Pawlik, Joseph R.
Mangoni, Alfonso
Costantino, Valeria
author_facet Della Sala, Gerardo
Teta, Roberta
Esposito, Germana
Pawlik, Joseph R.
Mangoni, Alfonso
Costantino, Valeria
author_sort Della Sala, Gerardo
collection PubMed
description Glycosylinositol phosphorylceramides (GIPCs) show a great structural diversity, but all share a small number of core structures, with a glucosamine, a mannose, or a glucuronic acid as the first sugar linked to the inositol. The Caribbean sponge Svenzea zeai was shown to consistently contain zeamide (1), the first example of a new class of GIPCs, in which the inositol is glycosylated by a d-arabinose. The structure of zeamide was determined by spectroscopic analysis (NMR, MS, ECD) and microscale chemical degradation. The 6-O-β-d-arabinopyranosyl-myo-inositol (d-Arap(1β→6)Ins) core motif of zeamide is unprecedented not only among GIPCs, but also in any natural glycoconjugate.
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spelling pubmed-61517862018-11-13 Zeamide, a Glycosylinositol Phosphorylceramide with the Novel Core Arap(1β→6)Ins Motif from the Marine Sponge Svenzea zeai Della Sala, Gerardo Teta, Roberta Esposito, Germana Pawlik, Joseph R. Mangoni, Alfonso Costantino, Valeria Molecules Article Glycosylinositol phosphorylceramides (GIPCs) show a great structural diversity, but all share a small number of core structures, with a glucosamine, a mannose, or a glucuronic acid as the first sugar linked to the inositol. The Caribbean sponge Svenzea zeai was shown to consistently contain zeamide (1), the first example of a new class of GIPCs, in which the inositol is glycosylated by a d-arabinose. The structure of zeamide was determined by spectroscopic analysis (NMR, MS, ECD) and microscale chemical degradation. The 6-O-β-d-arabinopyranosyl-myo-inositol (d-Arap(1β→6)Ins) core motif of zeamide is unprecedented not only among GIPCs, but also in any natural glycoconjugate. MDPI 2017-09-01 /pmc/articles/PMC6151786/ /pubmed/28862696 http://dx.doi.org/10.3390/molecules22091455 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Della Sala, Gerardo
Teta, Roberta
Esposito, Germana
Pawlik, Joseph R.
Mangoni, Alfonso
Costantino, Valeria
Zeamide, a Glycosylinositol Phosphorylceramide with the Novel Core Arap(1β→6)Ins Motif from the Marine Sponge Svenzea zeai
title Zeamide, a Glycosylinositol Phosphorylceramide with the Novel Core Arap(1β→6)Ins Motif from the Marine Sponge Svenzea zeai
title_full Zeamide, a Glycosylinositol Phosphorylceramide with the Novel Core Arap(1β→6)Ins Motif from the Marine Sponge Svenzea zeai
title_fullStr Zeamide, a Glycosylinositol Phosphorylceramide with the Novel Core Arap(1β→6)Ins Motif from the Marine Sponge Svenzea zeai
title_full_unstemmed Zeamide, a Glycosylinositol Phosphorylceramide with the Novel Core Arap(1β→6)Ins Motif from the Marine Sponge Svenzea zeai
title_short Zeamide, a Glycosylinositol Phosphorylceramide with the Novel Core Arap(1β→6)Ins Motif from the Marine Sponge Svenzea zeai
title_sort zeamide, a glycosylinositol phosphorylceramide with the novel core arap(1β→6)ins motif from the marine sponge svenzea zeai
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6151786/
https://www.ncbi.nlm.nih.gov/pubmed/28862696
http://dx.doi.org/10.3390/molecules22091455
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