Identification of amphilectosins as key intermediates in pseudopterosin biosynthesis

J Org Chem. 2005 Aug 5;70(16):6152-7. doi: 10.1021/jo050282r.

Abstract

Amphilectosins A and B have been identified from the organic extract of Pseudopterogorgia elisabethae collected in the Florida Keys, along with seco-pseudopterosins and pseudopterosins. The structures of the amphilectosins, "C-12-C-13 dehydro seco-pseudopterosins", suggested that these metabolites provide the biosynthetic link between the seco-pseudopterosins (serrulatane diterpenes) and pseudopterosins (amphilectane diterpenes). This biosynthetic relationship was confirmed through various radiolabeling experiments. Incubation studies with the amphilectosins revealed the selective transformation of amphilectosin A to pseudopterosin Y and the transformation of amphilectosin B to pseudopterosin F, which suggests that the alpha/beta stereochemistry for the isobutenyl group in the pseudopterosins arises from the selective ring closure of the cis- and trans-amphilectosins.

Publication types

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

MeSH terms

  • Animals
  • Anthozoa / chemistry
  • Anthozoa / metabolism
  • Diterpenes / blood
  • Diterpenes / chemistry*
  • Diterpenes / metabolism*
  • Glycosides / biosynthesis*
  • Glycosides / blood
  • Glycosides / chemistry*
  • Glycosides / metabolism*
  • Molecular Structure

Substances

  • Diterpenes
  • Glycosides
  • amphilectosin A
  • amphilectosin B
  • pseudopterosins