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Antimalarial Polyketide Cycloperoxides from the Marine Sponge Plakortis simplex
Author(s) -
Campagnuolo Claudio,
Fattorusso Ernesto,
Romano Adriana,
TaglialatelaScafati Orazio,
Basilico Nicoletta,
Parapini Silvia,
Taramelli Donatella
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500404
Subject(s) - chemistry , plasmodium falciparum , polyketide , stereochemistry , potency , antimalarial agent , sponge , combinatorial chemistry , chloroquine , in vitro , enzyme , biochemistry , malaria , biosynthesis , botany , immunology , biology
Three new ( 5 – 7 ) and two known ( 4 and 8 ) polyketide derivatives have been isolated from the Caribbean sponge Plakortis simplex . Their stereostructures have been determined by spectroscopic methods and chemical transformations that include Zn‐mediated reduction and Dess–Martin oxidation, and by application of Mosher’s method. The cycloperoxide derivatives plakortide Q ( 7 ) and compound 8 were evaluated for their in vitro antimalarial activity against chloroquine‐sensitive and chloroquine‐resistant strains of Plasmodium falciparum . The lower potency of these molecules relative to plakortin indicates that the change of configuration at C‐3 exerts negative effects on the antimalarial activity. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)