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.
Katavic, PL, Yong, KW, Herring, JN, Deseo, MA, Blanchfield, JT, Ferro, V & Garson, MJ 2013, 'Structure and stereochemistry of an anti-inflammatory anhydrosugar from the Australian marine sponge Plakinastrella clathrata and the synthesis of two analogues', Tetrahedron, vol. 69, no. 37, pp. 8074-8079.
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