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Isolation, structure elucidation, and synthesis of antiplasmodial quinolones from Crinum firmifolium.


ABSTRACT: Antiplasmodial bioassay guided fractionation of a Madagascar collection of Crinum firmifolium led to the isolation of seven compounds. Five of the seven compounds were determined to be 2-alkylquinolin-4(1H)-ones with varying side chains. Compounds 1 and 4 were determined to be known compounds with reported antiplasmodial activities, while 5 was believed to be a new branched 2-alkylquinolin-4(1H)-one, however, it was isolated in limited quantities and in admixture and therefore was synthesized to confirm its structure as a new antiplasmodial compound. Along with 5, two other new and branched compounds 6 and 7 were synthesized as well. Accompanying the five quinolones were two known compounds 2 and 3 which are inactive against Plasmodium falciparum. The isolation, structure elucidation, total synthesis, and biological evaluation of these compounds are discussed in this article.

SUBMITTER: Presley CC 

PROVIDER: S-EPMC5557408 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

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Isolation, structure elucidation, and synthesis of antiplasmodial quinolones from Crinum firmifolium.

Presley Christopher C CC   Du Yongle Y   Dalal Seema S   Merino Emilio F EF   Butler Joshua H JH   Rakotonandrasana Stéphan S   Rasamison Vincent E VE   Cassera Maria B MB   Kingston David G I DGI  

Bioorganic & medicinal chemistry 20170613 15


Antiplasmodial bioassay guided fractionation of a Madagascar collection of Crinum firmifolium led to the isolation of seven compounds. Five of the seven compounds were determined to be 2-alkylquinolin-4(1H)-ones with varying side chains. Compounds 1 and 4 were determined to be known compounds with reported antiplasmodial activities, while 5 was believed to be a new branched 2-alkylquinolin-4(1H)-one, however, it was isolated in limited quantities and in admixture and therefore was synthesized to  ...[more]

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