Isolation of a new butenolide from the South China Sea gorgonian coral Subergorgia suberosa

Nat Prod Res. 2014;28(3):150-5. doi: 10.1080/14786419.2013.857668. Epub 2013 Nov 18.

Abstract

Chemical investigation on the South China Sea gorgonian coral Subergorgia suberosa has led to the isolation of one new butenolide (5R)-5-(1-ethoxypropyl)-5-hydroxy-3,4-dimethylfuran-2(5H)-one (1) as a pair of inseparable epimers, along with two known butenolides (S)-5-hydroxy-3,4-dimethyl-5-propylfuran-2(5H)-one (2) and (S)-5-hydroxy-3,4-dimethyl-5-pentylfuran-2(5H)-one (3). Their structures including absolute configurations were determined unambiguously by detailed analyses of spectroscopic data and by comparison with the available literature. Compounds 1-3 exhibited moderate antifouling activities against the settlement of Balanus amphitrite larvae, whereas compound 4, the acetyl derivative of 3, showed no antifouling activity at the concentrations up to 25 μg/mL.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemistry
  • 4-Butyrolactone / isolation & purification
  • 4-Butyrolactone / pharmacology
  • Animals
  • Anthozoa / chemistry*
  • Dose-Response Relationship, Drug
  • Larva / drug effects
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Oceans and Seas
  • Thoracica / drug effects
  • Water Pollutants, Chemical / antagonists & inhibitors

Substances

  • (5R)-5-(1-ethoxypropyl)-5-hydroxy-3,4-dimethylfuran-2(5H)-one
  • Water Pollutants, Chemical
  • butenolide
  • 4-Butyrolactone