Structure and stereochemistry of an anti-inflammatory anhydrosugar from the Australian marine sponge Plakinastrella clathrata and the synthesis of two analogues

• Published in: Tetrahedron Vol. 69; no. 37; pp. 8074 - 8079
• Main Authors: Katavic, Peter L., Yong, Ken W.L., Herring, Joel N., Deseo, Myrna A., Blanchfield, Joanne T., Ferro, Vito, Garson, Mary J.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 16.09.2013; Elsevier
• Subjects: Anhydrosugars; Australia; Biotechnology; Chemistry; Chemistry, Organic; Lactates; Marine; NMR; Physical Sciences; Plakinastrella; Science & Technology; Screening; Sponges; Stereochemistry; Synthesis; Tetrahedrons; Australia; NMR; Sponges; Stereochemistry; Anhydrosugars; GLYCOLIPIDS; AMPD
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2013.06.079

The structure and relative/absolute configuration of the C-15:0 iso-branched fatty acyl 1,6-anhydropyranose 1 isolated from the Australian marine sponge Plakinastrella clathrata have been investigated. Synthesis of the C-16:0 side chain-modified analogues 3 and 4 has enabled the relative configuration of the C-3 lactate moiety to be secured. In a preliminary anti-inflammatory screening, glycolipid 1 exhibited moderate activity in a PGE2 inhibition assay, however, the compound showed no activity in cytotoxicity screening using 3T3 and P388 cell lines. [Display omitted] The structure, relative and absolute configuration of a glycolipid component 1 isolated from Plakinastrella clathrata have been confirmed by synthesis of analogues 3 and 4.