Amitorines A and B, Nitrogenous Diterpene Metabolites of Theonella swinhoei: Isolation, Structure Elucidation, and Asymmetric Synthesis

J Nat Prod. 2016 Apr 22;79(4):996-1004. doi: 10.1021/acs.jnatprod.5b01069. Epub 2016 Mar 23.

Abstract

Two new nitrogenous prenylbisabolanes never before found in Lithistid sponges have been isolated from Theonella swinhoei. These new diterpenes, named amitorine A (1) and amitorine B (2), containing a prenylbisabolane skeleton have been characterized by spectroscopic analyses, and the relative and absolute configurations of 1 and 2 were determined by asymmetric synthesis of both diastereomers via the common bicyclic lactone 6 intermediate.

MeSH terms

  • Animals
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Japan
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Theonella / chemistry*

Substances

  • Diterpenes
  • amitorine A
  • amitorine B
  • prenylbisabolane