The cold waters of Antarctica are known to harbor a rich biodiversity. Our continuing interest in the chemical analysis of Antarctic invertebrates has resulted in the isolation of friomaramide (), a new, highly modified hexapeptide, from the Antarctic sponge . The structure of friomaramide was determined using spectroscopic methods and its configuration established by Marfey's method. Friomaramide, which bears the unusual permethylation of the amino acid backbone and is the longest polypeptide bearing a tryptenamine C-terminus, blocks >90% of liver-stage parasite development at 6.1 μM.
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Highly -Methylated Peptides from the Antarctic Sponge Are Active against .
J Nat Prod
October 2022
Department of Chemistry, University of South Florida, 4202 E. Fowler Avenue, CHE205, Tampa, Florida 33620, United States.
Malaria, caused by the parasite , continues to threaten much of the world's population, and there is a pressing need for expanding treatment options. Natural products have been a vital source of such drugs, and here we report seven new highly -methylated linear peptides, friomaramide B () and shagamides A-F (-) from the marine sponge , collected in Antarctic waters, which demonstrate activity against three strains of blood-stage The planar structures of these metabolites were solved by interpreting NMR data, as well as HRESIMS/MS fragmentation patterns, while Marfey's analysis was used to establish the configurations of the amino acids. Reisolation of the previously reported compound friomaramide A () allowed us to revise its structure.
View Article and Find Full Text PDFFriomaramide, a Highly Modified Linear Hexapeptide from an Antarctic Sponge, Inhibits Liver-Stage Development.
J Nat Prod
August 2019
Department of Chemistry , University of South Florida, 4202 E. Fowler Avenue, CHE205 , Tampa , Florida 33620 , United States.
The cold waters of Antarctica are known to harbor a rich biodiversity. Our continuing interest in the chemical analysis of Antarctic invertebrates has resulted in the isolation of friomaramide (), a new, highly modified hexapeptide, from the Antarctic sponge . The structure of friomaramide was determined using spectroscopic methods and its configuration established by Marfey's method.
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