Ochracenoids A and B, guaiazulene-based analogues from gorgonian Anthogorgia ochracea collected from the South China Sea

Mar Drugs. 2014 Mar 14;12(3):1569-79. doi: 10.3390/md12031569.

Abstract

Two new guaiazulene-based analogues, ochracenoids A (1) and B (2), along with four known analogues (3-6), were isolated from the gorgonian Anthogorgia ochracea collected from the South China Sea. The planar structures of the new compounds were elucidated by comprehensive spectroscopic data. The absolute configuration of 1 was determined as 3R by the comparison of TDDFT calculated electronic circular dichroism with its experimental spectrum. Compound 1 is a rare guaiazulene-based analogue possessing a unique C₁₆ skeleton. The possible generation process of 1 through an intermolecular one-carbon-transfer reaction was also discussed. Compound 2 was previously described as a presumed intermediate involved in the biogenesis of anthogorgienes A and I. Compound 3 exhibited antiproliferative effects on the embryo development of zebrafish Danio rerio.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthozoa / chemistry*
  • Azulenes / chemistry*
  • Azulenes / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Circular Dichroism
  • Drug Screening Assays, Antitumor
  • Embryo, Nonmammalian
  • High-Throughput Screening Assays
  • Humans
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Models, Molecular
  • Molecular Conformation
  • Pacific Ocean
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / pharmacology
  • Sesquiterpenes, Guaiane
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Zebrafish

Substances

  • Azulenes
  • Sesquiterpenes
  • Sesquiterpenes, Guaiane
  • guaiazulene