Euryjanicins E-G, poly-phenylalanine and poly-proline cyclic heptapeptides from the Caribbean spongeProsuberites laughlini.
A new investigation of the active sponge extracts ofProsuberites laughlinicollected off the West coast of Puerto Rico has yielded three new cyclic heptapeptides, namely euryjanicins E (1)-G (3), containing multiple phenylalanine and proline residues. In CDCl3solution, each euryjanicin F (2) and G (3) exists as an inseparable complex mixture of conformational isomers. The molecular structures of1-3were elucidated by a combination of chemical degradation, extensive ESI-MS/MSnanalyses, and 2D NMR methods. The elucidation of the absolute configuration was achieved by HPLC following analysis of the acid hydrolysates after derivatization with Marfey's reagent. When assayed against the National Cancer Institute 60 tumor cell line panel, the new cyclic peptides did not display significantin vitrocytotoxicity.
Department of Chemistry, University of Puerto Rico, PO Box 23346, UPR Station, San Juan, PR 00931-3346, United States.
Edward
E
Avilés
Department of Chemistry, University of Puerto Rico, PO Box 23346, UPR Station, San Juan, PR 00931-3346, United States.
Abimael D
AD
Rodríguez
Caribbean sponge; Cyclic peptides; Cytotoxicity; Peptides; Prosuberites laughlini