Spheciosterol sulfates, PKCzeta inhibitors from a philippine sponge Spheciospongia sp
- PMID: 18558742
- PMCID: PMC2593898
- DOI: 10.1021/np8001628
Spheciosterol sulfates, PKCzeta inhibitors from a philippine sponge Spheciospongia sp
Abstract
Three new sterol sulfates, spheciosterol sulfates A-C (1-3), and the known sterol sulfate topsentiasterol sulfate E (4) have been isolated from the sponge Spheciospongia sp., collected in the Philippines. Structures were assigned on the basis of extensive 1D and 2D NMR studies as well as analysis by HRESIMS. Compounds 1-4 inhibited PKCzeta with IC50 values of 1.59, 0.53, 0.11, and 1.21 microM, respectively. In a cell-based assay, 1-4 also inhibited NF-kappaB activation with EC50 values of 12-64 microM.
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References
-
- Sarma N. S.; Krishna M. S. R.; Rao S. R. Mar. Drugs 2005, 3, 84–111.
-
- D’Auria M. V.; Minale L.; Riccio R. Chem. Rev. 1993, 93, 1839–1895.
-
- McKee T. C.; Cardellina J. H., II; Riccio R.; D’Auria M. V.; Iorizzi M.; Minale L.; Moran R. A.; Gulakowski R. J.; McMahon J. B.; Buckheit R.W., Jr.; Snader K. M.; Boyd M. R. J. Med. Chem. 1994, 37, 793–797. - PubMed
-
- Lerch M. L.; Faulkner D. J. Tetrahedron 2001, 57, 4091–4094.
-
- Sun H. H.; Cross S. S.; Gunasekera M.; Koehn F. E. Tetrahedron 1991, 47, 1185–1190.
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