Employing dereplication and gradient 1D NMR methods to rapidly characterize sponge-derived sesterterpenes

J Nat Prod. 2002 Aug;65(8):1183-6. doi: 10.1021/np010218e.

Abstract

The sesterterpene constituents of two Indo-Pacific sponges were investigated and rapidly characterized using aggressive dereplication methods along with gradient 1D NMR techniques. Lendenfeldia frondosa yielded three sesterterpenes: 12beta,16beta,22-trihydroxy-24alpha-methylscalar-25beta,24alpha-olide (1), the 24 epimer of a known compound; 12beta,22-dihydroxy-24-methylscalar-17-en-24,25-olide (2), a known compound; and 22-hydroxy-24-methylsedn-16-en-24-one-12beta,25beta-olide (3), a new compound. A Hyrtios sp. sponge yielded known 12alpha-acetoxy-16beta-hydroxyscalarolbutenolide (5).

Publication types

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

MeSH terms

  • Animals
  • Chromatography, High Pressure Liquid
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular / methods*
  • Papua New Guinea
  • Porifera / chemistry*
  • Stereoisomerism
  • Terpenes / chemistry*
  • Terpenes / isolation & purification

Substances

  • 12alpha-acetoxy-16beta-hydroxyscalarolbutenolide
  • 12beta,16beta,22-trihydroxy-24alpha-methylscalar-25beta,24alpha-olide
  • 12beta,22-dihydroxy-24-methylscalar-17-en-24,25-olide
  • 22-hydroxy-24-methylsedn-16-en-24-one-12beta,25beta-olide
  • Terpenes