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Papuamides A−D, HIV-Inhibitory and Cytotoxic Depsipeptides from the Sponges Theonella mirabilis and Theonella swinhoei Collected in Papua New Guinea
journal contribution
posted on 1999-06-15, 00:00 authored by Paul W. Ford, Kirk R. Gustafson, Tawnya C. McKee, Nobuharu Shigematsu, Laura K. Maurizi, Lewis K. Pannell, David E. Williams, E. Dilip de Silva, Peter Lassota, Theresa M. Allen, Rob Van Soest, Raymond J. Andersen, Michael R. BoydThe novel cyclic depsipeptides papuamides A (1), B (2), C (3), and D (4) have been isolated from
Papua New Guinea collections of the sponges Theonella mirabilis and Theonella swinhoei. Their structures
were determined by a combination of spectroscopic analysis and chemical degradation and derivatization studies.
In addition to glycine, alanine, and threonine, these peptides contain a number of unusual amino acids including
3,4-dimethylglutamine, β-methoxytyrosine, 3-methoxyalanine, and 2,3-diaminobutanoic acid or 2-amino-2-butenoic acid residues. Papuamides A−D (1−4) are also the first marine-derived peptides reported to contain
3-hydroxyleucine and homoproline residues. These peptides also contain a previously undescribed 2,3-dihydroxy-2,6,8-trimethyldeca-(4Z,6E)-dienoic acid moiety N-linked to a terminal glycine residue. Papuamides A (1)
and B (2) inhibited the infection of human T-lymphoblastoid cells by HIV-1RF in vitro with an EC50 of
approximately 4 ng/mL. Compound 1 was also cytotoxic against a panel of human cancer cell lines with a
mean IC50 of 75 ng/mL.
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Sponges Theonella m irabilisRFchemical degradationPapua New Guinea collectionsCytotoxic DepsipeptidesTheonella swinhoeihomoproline residuesterminal glycine residueacidEC 50winhoei Collectednovel cyclic depsipeptides papuamidesPapuamidesponges Theonella mirabiliscancer cell linesIC 50HIVPapua New Guineaspectroscopic analysisderivatization studies
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