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Gymnangiamide, a cytotoxic pentapeptide from the marine hydroid Gymnangium regae

  1. Author:
    Milanowski, D. J.
    Gustafson, K. R.
    Rashid, M. A.
    Pannell, L. K.
    McMahon, J. B.
    Boyd, M. R.

  2. Author Address

    Gustafson, KR, NCI, Mol Targets Dev Program, Canc Res Ctr, Bldg 1052,Room 121, Frederick, MD 21702 USA NCI, Mol Targets Dev Program, Canc Res Ctr, Frederick, MD 21702 USA. SAIC Frederick, Intramural Res Support Program, Frederick, MD 21702 USA. NIDDKD, Bioorgan Chem Lab, Bethesda, MD 20892 USA. Univ S Alabama, Coll Med, USA, Canc Res Inst, Mobile, AL 36688 USA.
    1. Year: 2004
  2. Journal: Journal of Organic Chemistry
    1. 69
    2. 9
    3. Pages: 3036-3042
  4. Type of Article: Article
  1. Abstract:

    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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