Friomaramide, a Highly Modified Linear Hexapeptide from an Antarctic Sponge, Inhibits Plasmodium falciparum Liver-Stage Development

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 (1), a new, highly modified hexapeptide, from the Antarctic sponge Inflatella coelosphaeroides. The structu...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2019-08, Vol.82 (8), p.2354-2358
Main Authors: Knestrick, Matthew A, Wilson, Nerida G, Roth, Alison, Adams, John H, Baker, Bill J
Format: Article
Language:English
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Summary: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 (1), a new, highly modified hexapeptide, from the Antarctic sponge Inflatella coelosphaeroides. 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 Plasmodium falciparum liver-stage parasite development at 6.1 μM.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.9b00362