Aromatic cyclic peroxides and related keto-compounds from the Plakortis sp. component of a sponge consortium
- PMID: 19618913
- PMCID: PMC2842915
- DOI: 10.1021/np900310j
Aromatic cyclic peroxides and related keto-compounds from the Plakortis sp. component of a sponge consortium
Abstract
Six unreported aromatic compounds, 1-6, were isolated, along with the known compounds dehydrocurcuphenol and manoalide, from a sample of Plakortis sp., which was the main component of a Pacific sponge consortium. The new molecules were chemically characterized by spectroscopic methods. Compounds 1-4 contain a six-membered cyclic peroxide, whereas 5 and 6 display a terminal methyl ketone. The new metabolites were tested for antifungal and antibacterial properties. Compounds 1 and 4 were weakly active against S. aureus.
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References
-
- Blunt JW, Copp BR, Munro MHG, Northcote PT, Prinsep MR. Nat Prod Rep. 2006;23:26–78. and previous reports in this series. - PubMed
- Casteel DA. Nat Prod Rep. 2001;16:55–73.
-
- Higgs MD, Faulkner DJ. J Org Chem. 1978;43:3454–3457.
-
- Stierle DB, Faulkner DJ. J Org Chem. 1979;44:964–968.
- Braekman JC, Daloze D, De Groote S, Fernandes JB, Van Soest RWM. J Nat Prod. 1998;61:1038–1042. - PubMed
- Sakemi S, Higa T. Tetrahedron. 1987;43:263–268.
- Patil AD, Freyer AJ, Carte B, Johnson RK, Lahouratate P. J Nat Prod. 1996;59:219–223. - PubMed
- Jimenez dSM, Garzon SP, Rodriguez AD. J Nat Prod. 2003;66:655–661. - PubMed
- Stierle DB, Faulkner DJ. J Org Chem. 1980;45:3396–3401.
- Chen Y, McCarthy PJ, Harmody DK, Schimoler-O'Rourke R, Chilson K, Selitrennikoff C, Pomponi SA, Wright AE. J Nat Prod. 2002;65:1509–1512. - PubMed
- Yosief T, Rudi A, Wolde-ab Y, Kashman Y. J Nat Prod. 1998;61:491–493. - PubMed
- Rudi A, Talpir R, Kashman Y. J Nat Prod. 1993;56:2178–2182. - PubMed
- Gunasekera SP, Gunawardana GP, McCarthy P, Burres N. J Nat Prod. 1990;53:669–674.
- Murayama T, Ohizumi Y, Nakamura H, Sasaki T, Kobayashi J. Experientia. 1989;45:898–899.
- Rudi A, Kashman Y. J Nat Prod. 1993;56:1827–1830. - PubMed
- Berrué F, Thomas OP, Funel-Le Bon C, Reyes F, Amade P. Tetrahedron. 2005;61:11843–11849.
- Fontana A, Ishibashi M, Kobayashi J. Tetrahedron. 1998;54:2041–2048.
- Fattorusso E, Taglialatela-Scafati O, Di Rosa M, Ianaro A. Tetrahedron. 2000;56:7959–7967. - PubMed
-
- Rudi A, Afanii R, Garcia Gravalos L, Aknin M, Gaydou E, Vacelet J, Kashman Y. J Nat Prod. 2003;66:682–685. - PubMed
- Phillipson DW, Rinehart KL., Jr J Am Chem Soc. 1983;105:7735–7736.
- Perry TL, Dickerson A, Khan AA, Kondru RK, Beratan DN, Wipf P, Kelly M, Hamann MT. Tetrahedron. 2001;57:1483–1487.
- Davidson BS. Tetrahedron Lett. 1991;32:7167–7170.
- Horton PA, Longley RE, Kelly-Borges M, McConnell OJ, Ballas LM. J Nat Prod. 1994;57:1374–1381. - PubMed
- Varoglu M, Peters BM, Crews P. J Nat Prod. 1995;58:27–36. - PubMed
- Sandler JS, Colin PL, Hooper JNA, Faulkner DJ. J Nat Prod. 2002;65:1258–1261. - PubMed
-
- Ravi BN, Armstrong RW, Faulkner DJ. J Org Chem. 1979;44:3109–3113.
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