Bistellettazines A-C and bistellettazole A: new terpenyl-pyrrolizidine and terpenyl-imidazole alkaloids from a southern Australian marine sponge, Stelletta sp

Org Lett. 2008 Oct 2;10(19):4247-50. doi: 10.1021/ol8016512. Epub 2008 Sep 10.

Abstract

Four new alkaloids have been isolated during chemical investigations into a southern Australian marine sponge, Stelletta sp. Detailed spectroscopic analysis, supported by chemical degradation and partial synthesis, permitted structure elucidation of bistellettazines A-C ( 1- 3), the first reported examples of terpenyl-pyrrolizidine conjugates, and bistellettazole A ( 4), a unique cyclic terpenyl-imidazole conjugate. The alkaloids 1- 4 feature unprecedented carbon skeletons that are proposed to share a common convergent biosynthetic origin, arising via the biogenic equivalent of a Diels-Alder addition between two hypothetical polyenyl norsesquiterpene precursors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis
  • Amides / chemistry*
  • Amides / metabolism
  • Animals
  • Australia
  • Imidazoles / chemical synthesis
  • Imidazoles / chemistry*
  • Imidazoles / metabolism
  • Magnetic Resonance Spectroscopy
  • Porifera / chemistry*
  • Porifera / metabolism
  • Pyrrolizidine Alkaloids / chemical synthesis
  • Pyrrolizidine Alkaloids / chemistry*
  • Pyrrolizidine Alkaloids / metabolism

Substances

  • Amides
  • Imidazoles
  • Pyrrolizidine Alkaloids
  • bistellettazine A
  • bistellettazine B
  • bistellettazine C
  • bistellettazole A
  • imidazole