New and known diketopiperazines from the Caribbean sponge, Calyx cf. podatypa.
The cyanobacteria-containing Caribbean sponge, Calyx cf. podatypa, was collected from three sites in the Bahamas. In each of the three collections, a polar solvent partition fraction contained six known compounds including five diketopiperazines [1-4,6] and phenylacetic acid, along with a new diketopiperazine, cyclo-(4-methyl-R-proline-S-norvaline) [5]. Interestingly, all six diketopiperazines are proline-derived cyclic dipeptides. This is the first example for this class of peptide derivative to be isolated from a Calyx sponge. Parallel studies of one of the sponge collections in which the ectosome (cyanobacteria-rich) was separated from the endosome (no cyanobacteria) revealed no significant differences in their content of diketopiperazines.
Adamczeski
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M
Department of Chemistry and Biochemistry, University of California, Santa Cruz 95064, USA.
Reed
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AR
Crews
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D000595:Amino Acid Sequence; D000818:Animals; D001444:Bahamas; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009904:Optical Rotation; D010879:Piperazines / Q000737:chemistry* / Q000302:isolation & purification; D011161:Porifera / Q000737:chemistry*
D010879:Piperazines