Ceramides and cerebrosides from the marine bryozoan Bugula neritina inhabiting South China Sea

Abstract

From the marine bryozoan Bugula neritina inhabiting South China Sea, a new ceramide named (2S,3R,4E)-2-(14′-methyl-pentadecanoylamino)-4-octadecene-l,3-diol (1) and a new cerebroside named 1-O-(β-d-glucopyranosyl)-(2S,3R,4E)-2-(heptadecanoylamino)-4-octadecene-l,3-diol (6), together with one known ceramide (2) and three known cerebrosides (3, 4, and 5), were isolated. Their structures were deduced by extensive spectral analysis and chemical evidences. Compound 1 is branched with a methyl [–CH(CH₃)₂] in the fatty acid moiety, which is a rare structural feature among ceramides. Compound 6 is a new cerebroside with 17 carbons in the fatty acid moiety, while 5 is a new natural product which was isolated from a natural origin for the first time.

Keywords:

• Bugula neritina
• cerebroside
• ceramide
• (2S,3R,4E)-2-(14′-methyl-pentadecanoylamino)-4-octadecene-l,3-diol
• 1-O-(β-d-glucopyranosyl)-(2S,3R,4E)-2-(heptadecanoylamino)-4-octadecene-l,3-diol

Acknowledgements

This work was financially supported by the National High-Tech Research and Development Project (863 Project, 2007AA09Z401). The authors are grateful to Dr M.C. Wang, Nuclear Magnetic Resonance Center, Xi'an Modern Chemistry Research Institute, for the NMR measurements.