Ford, P. W.; Gustafson, K. R.; McKee, T. C.; Shigematsu, N.; Maurizi, L. K.; Pannell, L. K.; Williams, D. E.; Dilip de Silva, E.; Lassota, P.; Allen, T. M.; Van Soest, R.; Andersen, R. J.; Boyd, M. R. (1999). Papuamides A−D, HIV-Inhibitory and Cytotoxic Depsipeptides from the Sponges Theonella mirabilis and Theonella swinhoei Collected in Papua New Guinea. Journal of the American Chemical Society. 121(25): 5899-5909.

438246

10.1021/ja990582o [view]

Ford, P. W.; Gustafson, K. R.; McKee, T. C.; Shigematsu, N.; Maurizi, L. K.; Pannell, L. K.; Williams, D. E.; Dilip de Silva, E.; Lassota, P.; Allen, T. M.; Van Soest, R.; Andersen, R. J.; Boyd, M. R.

1999

121(25): 5899-5909

Publication

https://pubs.acs.org/doi/10.1021/ja990582o

Available for editors   [request]

The 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.

Pacific, South West

Biochemistry
Chemistry

Porifera

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