Article

Bioactive Cycloperoxides Isolated from the Puerto Rican Sponge Plakortis halichondrioides.

Department of Chemistry, University of Puerto Rico, P.O. Box 23346, UPR Station, San Juan, Puerto Rico 00931-3346, and Department of Molecular Medicine, Beckman Research Institute, City of Hope, 500 East Duarte Road, Duarte, California 91010, United States.
Journal of Natural Products (impact factor: 3.13). 10/2010; DOI:10.1021/np100461t
Source: PubMed

ABSTRACT Two new five-membered-ring polyketide endoperoxides, epiplakinic acid F methyl ester (1) and epiplakinidioic acid (3), and a peroxide-lactone, plakortolide J (2), were isolated from the Puerto Rican sponge Plakortis halichondrioides, along with two previously reported cyclic peroxides, 4 and 5. The structures of the new metabolites were determined by spectroscopic and chemical analyses. The absolute stereostructures of 1, 2, and 5 were determined by degradation reactions followed by application of Kishi's method for the assignment of absolute configuration of alcohols. Biological screening of cycloperoxides 1-5 and semisynthetic analogues 7-12 for cytotoxic activity against various human tumor cell lines revealed that compounds 3, 4, and 11 are very active. Upon assaying for antimalarial and antitubercular activity, some of the compounds tested showed strong activity against the pathogenic microbes Plasmodium falciparum and Mycobacterium tuberculosis.

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Keywords

alcohols
 
antimalarial
 
antitubercular activity
 
compounds 3
 
cytotoxic activity
 
degradation reactions
 
epiplakinic acid F methyl ester
 
Kishi's method
 
new five-membered-ring polyketide endoperoxides
 
new metabolites
 
pathogenic microbes Plasmodium falciparum
 
plakortolide J
 
Puerto Rican sponge Plakortis halichondrioides
 
semisynthetic analogues 7-12
 
spectroscopic
 
strong activity
 
various human tumor cell lines