3-Bromohomofascaplysin A, a fascaplysin analogue from a Fijian Didemnum sp. ascidian

A new fascaplysin analogue, 3-bromohomofascaplysin A (1), along with two known analogues, homofascaplysin A (2) and fascaplysin (3), were isolated from a Fijian Didemnum sp. ascidian. The absolute configurations of 3-bromohomofascaplysin A (1) and homofascaplysin A (2) were determined via experiment...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2011-11, Vol.19 (22), p.6604-6607
Main Authors: Lu, Zhenyu, Ding, Yuanqing, Li, Xing-Cong, Djigbenou, Daignon R., Grimberg, Brian T., Ferreira, Daneel, Ireland, Chris M., Van Wagoner, Ryan M.
Format: Article
Language:English
Subjects:
Absolute configuration
Animals
Antimalarial
antimalarials
Antimalarials - chemistry
Antimalarials - isolation & purification
Antimalarials - pharmacology
Ascidian
blood
chemistry
Didemnum
drug therapy
Experimental and theoretically calculated ECD
Fascaplysin analogues
Hydrocarbons, Brominated - chemistry
Hydrocarbons, Brominated - isolation & purification
Indoles - chemistry
Indoles - isolation & purification
Indoles - pharmacology
inhibitory concentration 50
malaria
Marine
Molecular Conformation
Nuclear Magnetic Resonance, Biomolecular
parasites
pathogens
Plasmodium falciparum
Plasmodium falciparum - drug effects
Urochordata - chemistry
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Summary:A new fascaplysin analogue, 3-bromohomofascaplysin A (1), along with two known analogues, homofascaplysin A (2) and fascaplysin (3), were isolated from a Fijian Didemnum sp. ascidian. The absolute configurations of 3-bromohomofascaplysin A (1) and homofascaplysin A (2) were determined via experimental and theoretically calculated ECD spectra. The differential activities of 1–3 against different blood-borne life stages of the malaria pathogen Plasmodium falciparum were assessed. Homofascaplysin A (2) displayed an IC50 of 0.55±0.11nM against ring stage parasites and 105±38nM against all live parasites. Given the stronger resistance of ring stage parasites against most current antimalarials relative to the other blood stages, homofascaplysin A (2) represents a promising agent for treatment of drug resistant malaria.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2011.05.046