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Molecules 2017, 22(9), 1455; doi:10.3390/molecules22091455

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

The NeaNat Group, Dipartimento di Farmacia, Università degli Studi di Napoli Federico II, via D. Montesano 49, Napoli 80131, Italy
Department of Biology and Marine Biology, University of North Carolina Wilmington, Center for Marine Science, 5600 Marvin K Moss Lane, Wilmington, NC 28409, USA
Author to whom correspondence should be addressed.
Received: 19 August 2017 / Revised: 30 August 2017 / Accepted: 1 September 2017 / Published: 1 September 2017
(This article belongs to the Section Metabolites)
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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. View Full-Text
Keywords: glycosylinositol phosphorylceramides (GIPCs); d-arabinose; microscale chemical degradation glycosylinositol phosphorylceramides (GIPCs); d-arabinose; microscale chemical degradation

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Della Sala, G.; Teta, R.; Esposito, G.; Pawlik, J.R.; Mangoni, A.; Costantino, V. Zeamide, a Glycosylinositol Phosphorylceramide with the Novel Core Arap(1β→6)Ins Motif from the Marine Sponge Svenzea zeai. Molecules 2017, 22, 1455.

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