Rearranged Diterpenes and Norditerpenes from Three Australian Goniobranchus Mollusks

J Nat Prod. 2016 Mar 25;79(3):477-83. doi: 10.1021/acs.jnatprod.5b00866. Epub 2015 Dec 23.

Abstract

Three new norditerpenes (1, 6, and 7) and four diterpenes (2-5) with extensively rearranged carbon skeletons have been characterized from Australian nudibranchs. The relative configuration of the cyclopropyl-containing verrielactone (1) from Goniobranchus verrieri was suggested by spectroscopic analysis at 500 MHz informed by a combination of molecular modeling and DFT calculations. The nudibranchs G. splendidus and G. cf. splendidus provided 2-7, for which the structures and stereochemistry were deduced by 2D NMR studies at either 500 or 700 MHz. Each of the seven terpenoids exhibited a carbon skeleton modified from one of the tetrahydroaplysulphurin, spongionellin, or gracilane series of terpenes. A biosynthetic pathway to terpenes 1-7 from spongialactone is proposed.

MeSH terms

  • Animals
  • Australia
  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification*
  • Gastropoda / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Terpenes / chemistry

Substances

  • Diterpenes
  • Terpenes