Title

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

Document Type

Article

Publication details

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.

Published version available from:

http://dx.doi.org/10.1016/j.tet.2013.06.079

Peer Reviewed

Peer-Reviewed

Abstract

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.