[en] he extract of a sample of the sponge Theonella aff. swinhoei collected in Madagascar exhibited promising in vitro antiplasmodial activity. The antiplasmodial activity was ascribed in part to the known metabolite swinholide A. Further investigation of the extract afforded three unusual cyclic peptides, cyclotheonellazoles A–C (1–3), which contain six nonproteinogenic amino acids out of the eight acid units that compose these natural products. Among these acids the most novel were 4-propenoyl-2-tyrosylthiazole and 3-amino-4-methyl-2-oxohexanoic acid. The structure of the compounds was elucidated by interpretation of the 1D and 2D NMR data, HRESIMS, and advanced Merfay’s techniques. The new compounds were found to be nanomolar inhibitors of chymotrypsin and sub-nanomolar inhibitors of elastase, but did not present antiplasmodial activity.
Disciplines :
Pharmacy, pharmacology & toxicology
Author, co-author :
Issac, Michal
Aknin, Maurice
Gauvin-Bialecki, Anne
De Voogd, Nicole
Ledoux, Allison ; Université de Liège > Département de pharmacie > Pharmacognosie
Frederich, Michel ; Université de Liège > Département de pharmacie > Pharmacognosie
Kashman, Yoel
Carmeli, Shmuel
Language :
English
Title :
Cyclotheonellazoles A–C, Potent Protease Inhibitors from the Marine Sponge Theonella aff. swinhoei
Publication date :
16 February 2017
Journal title :
Journal of Natural Products
ISSN :
0163-3864
eISSN :
1520-6025
Publisher :
American Chemical Society, Washington, United States - District of Columbia
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