Bromopyrrole alkaloids from a marine sponge Agelas sp

Chem Pharm Bull (Tokyo). 2014;62(5):499-503. doi: 10.1248/cpb.c14-00077.

Abstract

Five new bromopyrrole alkaloids, 2-bromokeramadine (1), 2-bromo-9,10-dihydrokeramadine (2), tauroacidins C (3) and D (4), and mukanadin G (5), were isolated from an Okinawan marine sponge Agelas sp. The structures of 1-5 were elucidated on the basis of spectroscopic data and conformational analysis. Mukanadin G (5) has a tricyclic skeleton consisting of a fused tetrahydrobenzaminoimidazole and 2,5-dioxopyrrolidine moieties. Antimicrobial activities of 1-3, and 5 as well as three related known bromopyrrole alkaloids, keramadine (6), tauroacidin A (7), and taurodispacamide A (8) were evaluated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology*
  • Bacteria / drug effects
  • Dose-Response Relationship, Drug
  • Fungi / drug effects
  • Hydrocarbons, Brominated / chemistry
  • Hydrocarbons, Brominated / isolation & purification
  • Hydrocarbons, Brominated / pharmacology*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Porifera / chemistry*
  • Pyrroles / chemistry
  • Pyrroles / isolation & purification
  • Pyrroles / pharmacology*
  • Structure-Activity Relationship

Substances

  • Alkaloids
  • Anti-Bacterial Agents
  • Antifungal Agents
  • Hydrocarbons, Brominated
  • Pyrroles