(±)-Gelliusines A and B, Two Diastereomeric Brominated Tris-indole Alkaloids from a Deep Water New Caledonian Marine Sponge (Gellius or Orina sp.)

Abstract

Two new diastereomeric brominated tris-indole alkaloids occurring as enantiomeric pairs, (+/-)-gelliusines A [1] and B [2], have been isolated from a deep water New Caledonian sponge (Gellius or Orina sp.), whose crude extract exhibited cytotoxicity against KB cells. Their structures were elucidated by spectroscopic methods including one- and two-dimensional nmr spectroscopy. The major compound, (+/-) gelliusine A [1], which showed very weak cytotoxicity, proved to be active at the serotonin receptor.

Marine Indole Alkaloids: Potential New Drug Leads for the Control of Depression and Anxiety

“…Several compounds carrying an indole moiety have been reported to possess affinity towards different serotonin receptors: barettin, 8,9-dihydrobarettin,13 tris-indole alkaloids gelliusine A and B,14 and σ-conotoxin 15. Methylaplysinopsin ( 1 ) (Fig.…”

Marine Bi-, Bis-, and Trisindole Alkaloids

“…(or Gellius sp.) and were the first reported examples of trisindoles from the marine environment 127 (Figure 1.20). While gelliusine A exhibited weak cytotoxicity, it was shown to act as a partial agonist of serotonin receptors.…”

Bis and Tris Indole Alkaloids from Marine Organisms: New Leads for Drug Discovery

“…Gelliusines A and B showed cytotoxicity with an IC 50 value of between 10 and 20 µg/ml against KB, P-388, P-388/dox, HT-29 and NSCLCN-6 cell lines [81]. The percentage inhibition of gelliusines A 66 for the receptor sites Somatostatin, Neuropeptide Y, Human B2 bradykinin are 100, 90 and 100% respectively, while that of gelliusines B 67 are 100, 62 and 93%.…”