Ianthesine E, a new bromotyrosine-derived metabolite from the Great Barrier Reef sponge Pseudoceratina sp

Nat Prod Res. 2008;22(14):1257-63. doi: 10.1080/14786410701763411.

Abstract

The new compound ianthesine E (1) was isolated from the Great Barrier Reef marine sponge Pseudoceratina sp. along with the known metabolites 11-hydroxyaerothionin (2), aerothionin (3) and 11,19-dideoxyfistularin 3 (4). Structures were determined on the basis of their spectroscopic data. The compounds were tested for inhibition of [(3)H] DPCPX binding to adenosine A(1) receptors in a whole cell binding assay. At 100 microM, aerothionin was the most potent, inhibiting 67% of binding, followed by ianthesine E and 11-hydroxyaerothionin which inhibited 61% of binding, and 11,19-dideoxyfistularin which initiated 51% of binding Ianthesine E (EC(50) 60 microM), aerothionin (EC(50) 42 microM) and 11,19-dideoxyfistularin-3 (EC(50) 2.6 microM) exhibited moderate cytotoxicity against the HeLa cell line.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • CHO Cells
  • Chromatography, High Pressure Liquid
  • Cricetinae
  • Cricetulus
  • Humans
  • Magnetic Resonance Spectroscopy
  • Porifera / chemistry*
  • Porifera / metabolism
  • Receptor, Adenosine A1 / metabolism
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Ultraviolet
  • Tyrosine / analogs & derivatives*
  • Tyrosine / metabolism

Substances

  • Receptor, Adenosine A1
  • bromotyrosine
  • Tyrosine