Tulongicin, an Antibacterial Tri-Indole Alkaloid from a Deep-Water Topsentia sp. Sponge

J Nat Prod. 2017 Sep 22;80(9):2556-2560. doi: 10.1021/acs.jnatprod.7b00452. Epub 2017 Aug 24.

Abstract

Antibacterial-guided fractionation of an extract of a deep-water Topsentia sp. marine sponge led to the isolation of two new indole alkaloids, tulongicin A (1) and dihydrospongotine C (2), along with two known analogues, spongotine C (3) and dibromodeoxytopsentin (4). Their planar structures were determined by NMR spectroscopy. Their absolute configurations were determined through a combination of experimental and computational analyses. Tulongicin (1) is the first natural product to contain a di(6-Br-1H-indol-3-yl)methyl group linked to an imidazole core. The coexistence of tri-indole 1 and bis-indole alcohol 2 suggests a possible route to 1. All of the compounds showed strong antimicrobial activity against Staphylococcus aureus.

Publication types

  • Research Support, N.I.H., Intramural

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology*
  • Imidazoles / chemistry*
  • Indole Alkaloids / chemistry
  • Indole Alkaloids / isolation & purification*
  • Indole Alkaloids / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Porifera
  • Staphylococcus aureus / chemistry*
  • Staphylococcus aureus / drug effects*
  • Water

Substances

  • Anti-Bacterial Agents
  • Imidazoles
  • Indole Alkaloids
  • dihydrospongotine C
  • tulongicin
  • Water
  • imidazole