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J Org Chem. 2004 Apr 30;69(9):3036-42.

Gymnangiamide, a cytotoxic pentapeptide from the marine hydroid Gymnangium regae.

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Molecular Targets Development Program, Center for Cancer Research, National Cancer Institute, Building 1052, Room 121, Frederick, Maryland 21702-1201, USA.


A cytotoxic aqueous extract from the marine hydroid Gymnangium regae provided a novel linear pentapeptide, designated gymnangiamide (1). The planar structure of 1 was elucidated by interpretation of spectral data as well as chemical degradation and derivatization studies. In addition to the amino acids isoleucine and phenylserine, this peptide contained N-desmethyldolaisoleuine, O-desmethyldolaproine, and alpha-guanidino serine, three residues that have not previously been reported in a natural product. The absolute configurations of the constituent amino/guanidino acids were determined by chemical degradation and derivatization, followed by HPLC and LC-MS comparison with authentic standards. Gymnangiamide (1) was moderately cytotoxic against a number of human tumor cell lines in vitro.

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