Amphimelibiosides A-F, six new ceramide dihexosides isolated from a Japanese marine sponge Amphimedon sp.

Chisato Emura, Ryuichi Higuchi, Tomofumi Miyamoto, Rob W.M. Van Soest

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12 Citations (Scopus)

Abstract

(Chemical Equation Presented) Six new ceramide dihexosides, amphimelibiosides A-F (1-6), were isolated from a Japanese marine sponge Amphimedon sp. The structure of amphimelibioside C (3), which is a major component of amphimelibiosides, was determined by 2D NMR techniques, chemical degradation, and a semi-synthetic method to be 1-O-[β-D-glucopyranosyl- (1→6)-α-D-galactopyranosyl]-(2S,3S,4R,6E)-2-[(2′R) -2-hydroxydocosanoyl]-2-amino-6-octadecene-1,3,4-triol. The structures of the other constituents were elucidated by a combination of mass spectra, 1H NMR, and GC-MS analysis.

Original languageEnglish
Pages (from-to)3031-3038
Number of pages8
JournalJournal of Organic Chemistry
Volume70
Issue number8
DOIs
Publication statusPublished - Apr 15 2005

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Nuclear magnetic resonance
Degradation
ceramide dihexoside
1-octadecene

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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Amphimelibiosides A-F, six new ceramide dihexosides isolated from a Japanese marine sponge Amphimedon sp. / Emura, Chisato; Higuchi, Ryuichi; Miyamoto, Tomofumi; Van Soest, Rob W.M.

In: Journal of Organic Chemistry, Vol. 70, No. 8, 15.04.2005, p. 3031-3038.

Research output: Contribution to journalArticle

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