New peroxylactones from the Jamaican sponge Plakinastrella onkodes, with inhibitory activity against the AIDS opportunistic parasitic infection Toxoplasma gondii

Authors
Perry, TL Dickerson, A Khan, AA Kondru, RK Beratan, DN Wipf, P Kelly, M Hamann, MT
Citation
Tl. Perry et al., New peroxylactones from the Jamaican sponge Plakinastrella onkodes, with inhibitory activity against the AIDS opportunistic parasitic infection Toxoplasma gondii, TETRAHEDRON, 57(8), 2001, pp. 1483-1487
Citations number
47
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
8
Year of publication
2001
Pages
1483 - 1487
Database
ISI
SICI code
0040-4020(20010218)57:8<1483:NPFTJS>2.0.ZU;2-8
Abstract
An analysis of the chemical constituents of Plakinastrella onkodes collecte d in Jamaica yielded three cyclic peroxides, including the known plakortoli de (1) and two new analogs of 1. The absolute configuration of plakortolide G ((3R,4R,6R,8S)-3) was determined by ab initio optical rotation computati ons using a coupled Hartree-Fock (CHF) method implemented in CADPAC. Plakor tolide (1) (J. Org. Chem. 1980, 45. 3396) and plakortolide G (3) exhibited potent inhibitory activity against the protozoan Toxoplasma gondii in HFF c ells and represent the first marine natural products reported with T. gondi i inhibitory activity. (C) 2001 Elsevier Science Ltd. All rights reserved.