TY - JOUR
T1 - Amphimelibiosides A-F, six new ceramide dihexosides isolated from a Japanese marine sponge Amphimedon sp.
AU - Emura, Chisato
AU - Higuchi, Ryuichi
AU - Miyamoto, Tomofumi
AU - Van Soest, Rob W.M.
PY - 2005/4/15
Y1 - 2005/4/15
N2 - (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.
AB - (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.
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U2 - 10.1021/jo048635u
DO - 10.1021/jo048635u
M3 - Article
C2 - 15822961
AN - SCOPUS:17444362631
VL - 70
SP - 3031
EP - 3038
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 8
ER -
