Journal
TETRAHEDRON
Volume 68, Issue 44, Pages 9095-9104Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.08.045
Keywords
Antarctica; Clerodane; Halimane; Labdane; Marine
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Funding
- Office of Polar Programs of the National Science Foundation [OPP-0442769, ANT-0838773, OPP-0442857, ANT-0838776]
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Detailed investigation of the Antarctic nudibranch Austrodoris kerguelenensis has resulted in the isolation of a diverse suite of new diterpenoid glyceride esters (1-16) related to the palmadorins (17-19), including one (palmadorin L (9)) that is the first halogenated diterpene from this well-studied nudibranch. Previous collections of A. kerguelenensis from McMurdo Sound, the Weddell Sea and the Western Antarctic Peninsula have afforded related diterpene glycerides, a natural product class implicated as a chemical defense in nudibranchs. In this paper we describe the isolation, structure elucidation, and stereochemical analysis of sixteen new palmadorins using a combination of one- and two-dimensional NMR techniques. Palmadorin A (17), B (18), D (1), M (10), N (11), and O (12) inhibit human erythroleukemia (HEL) cells with low micromolar IC50's, and palmadorin M inhibits Jak2, STAT5, and Erk1/2 activation in HEL cells and causes apoptosis, at 5 mu M. (C) 2012 Elsevier Ltd. All rights reserved.
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