Carriebowlinol, an antimicrobial tetrahydroquinolinol from an assemblage of marine cyanobacteria containing a novel taxon

J Nat Prod. 2015 Mar 27;78(3):534-8. doi: 10.1021/np500598x. Epub 2014 Dec 23.

Abstract

A combined biodiversity- and bioassay-guided natural products discovery approach was used to explore new groups of marine cyanobacteria for novel secondary metabolites with ecologically relevant bioactivities. Phylogenetic analysis of cyanobacterial collections from Belize revealed a new taxon not previously well explored for natural products. The new alkaloid 5-hydroxy-4-(chloromethyl)-5,6,7,8-tetrahydroquinoline (1), named carriebowlinol, and the known compound lyngbic acid (2) were isolated from a nonpolar extract and identified by NMR and MS techniques. Compounds 1 and 2 inhibited the growth of pathogenic and saprophytic marine fungi, and 1 inhibited the growth of marine bacteria, suggesting an antimicrobial ecological function.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkaloids / metabolism
  • Anti-Infective Agents* / chemistry
  • Anti-Infective Agents* / isolation & purification
  • Anti-Infective Agents* / pharmacology
  • Belize
  • Biodiversity
  • Biological Products* / chemistry
  • Biological Products* / isolation & purification
  • Biological Products* / pharmacology
  • Cyanobacteria / chemistry*
  • Marine Biology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Phylogeny
  • Quinolines* / chemistry
  • Quinolines* / isolation & purification
  • Quinolines* / pharmacology
  • Quinones

Substances

  • Alkaloids
  • Anti-Infective Agents
  • Biological Products
  • Quinolines
  • Quinones
  • carriebowlinol
  • 5,6,7,8-tetrahydroquinoline