New and known diketopiperazines from the Caribbean sponge, Calyx cf. podatypa

J Nat Prod. 1995 Feb;58(2):201-8. doi: 10.1021/np50116a007.

Abstract

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.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Amino Acid Sequence
  • Animals
  • Bahamas
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Optical Rotation
  • Piperazines / chemistry*
  • Piperazines / isolation & purification
  • Porifera / chemistry*

Substances

  • Piperazines