New isoquinolinequinone alkaloids from the South China Sea nudibranch Jorunna funebris and its possible sponge-prey Xestospongia sp

Fitoterapia. 2014 Jul:96:109-14. doi: 10.1016/j.fitote.2014.04.011. Epub 2014 Apr 24.

Abstract

Two new renieramycin-type bistetrahydroisoquinolinequinone alkaloids, fennebricins A (1) and B (5), and one new isoquinolinequinone alkaloid, N-formyl-1,2-dihydrorenierol (7), were isolated from the skin of the South China Sea nudibranch Jorunna funebris and its possible sponge-prey Xestospongia sp., together with eight known metabolites, including three bistetrahydroisoquinolinequinones (2-4) and five isoquinolinequinones (8-12). Their structures were elucidated by analysis of spectroscopic data including 1D and 2D NMR and high-resolution electrospray ionization mass spectrometry (HRESIMS) and by comparison with data for related known compounds. All the metabolites except for 7 occurred simultaneously in the two animals, supporting recent ecological studies that the nudibranch J. funebris preys on the sponge of the genus Xestospongia.

Keywords: Isoquinolinequinones; Jorunna funebris; Renieramycin-type alkaloids; Xestospongia sp..

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Animals
  • Gastropoda / chemistry*
  • Isoquinolines / chemistry
  • Isoquinolines / isolation & purification*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Quinolones / chemistry
  • Quinolones / isolation & purification
  • Quinones / chemistry
  • Quinones / isolation & purification*
  • Tetrahydroisoquinolines / chemistry
  • Tetrahydroisoquinolines / isolation & purification*
  • Xestospongia / chemistry*

Substances

  • Alkaloids
  • Isoquinolines
  • N-formyl-1,2-dihydrorenierol
  • Quinolones
  • Quinones
  • Tetrahydroisoquinolines
  • fennebricin A
  • fennebricin B