Further brominated bis- and tris-indole alkaloids from the deep-water New Caledonian marine sponge Orina Sp

J Nat Prod. 1995 Aug;58(8):1254-60. doi: 10.1021/np50122a017.

Abstract

Two tris-indole alkaloids, (+/-) gelliusines A and B [1], have been isolated for the first time from a marine source, the New Caledonian sponge, Orina sp. (or Gellius sp.), along with five further indole constituents [2-6]. Compound 6 has been identified as 2,2-bis-(6'-bromo-3'-indolyl(-ethylamine, previously isolated from the tunicate Didemnum candidum, but the remaining four indoles [2-5] are novel compounds. These showed anti-serotonin activity and a strong affinity for somatostatin and neuropeptide Y receptors in receptor-binding assays.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Animals
  • Calcitonin Gene-Related Peptide / metabolism
  • Cell Line
  • Galanin / metabolism
  • Guinea Pigs
  • Humans
  • Indoles / isolation & purification*
  • Indoles / pharmacology
  • Magnetic Resonance Spectroscopy
  • Male
  • New Caledonia
  • Porifera / chemistry*
  • Rats
  • Receptors, AMPA / antagonists & inhibitors
  • Receptors, N-Methyl-D-Aspartate / drug effects
  • Receptors, Neurotensin / drug effects
  • Receptors, Vasoactive Intestinal Peptide / drug effects
  • Serotonin Antagonists / isolation & purification
  • Serotonin Antagonists / pharmacology

Substances

  • Alkaloids
  • Indoles
  • Receptors, AMPA
  • Receptors, N-Methyl-D-Aspartate
  • Receptors, Neurotensin
  • Receptors, Vasoactive Intestinal Peptide
  • Serotonin Antagonists
  • gelliusine A
  • Galanin
  • Calcitonin Gene-Related Peptide