Journal
TETRAHEDRON
Volume 68, Issue 24, Pages 4635-4640Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.04.025
Keywords
Plakortis simplex; Simplexolide; Mosher's method; Antifungal; Cytotoxicity; Antimalarial; Absolute configuration
Categories
Funding
- National Natural Science Foundation of China [81072573]
- STCSM [09dZ1975800]
- NIH, NIAID, Division of AIDS [AI 27094]
- USDA Agricultural Research Service [58-6408-2-0009]
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Six new polyketides, simplexolides A-E (1-5) and a furan ester, plakorfuran A (6), together with four known furanylidenic methyl esters (7-10) were isolated from the marine sponge Plakortis simplex. Compounds 1-5 feature a tetrahydrofuran ring opened seco-plakortone skeleton. These new structures, including relative configurations, were determined on the basis of extensive analysis of spectroscopic data. The absolute configurations of 1-6 were established by the modified Mosher's method, and the CD exciton chirality method. However, configurations of the remote stereocenters at C-8 in compounds 1-5 were not determined. Antifungal, cytotoxicity, antileismanial, and antimalarial activities of these polyketides were evaluated. (C) 2012 Elsevier Ltd. All rights reserved.
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