Hirsutalins A-H, eunicellin-based diterpenoids from the soft coral Cladiella hirsuta

J Nat Prod. 2010 Nov 29;73(11):1785-91. doi: 10.1021/np100401f. Epub 2010 Oct 27.

Abstract

Eight new eunicellin-base diterpenoids, hirsutalins A-H (1-8), were isolated from the soft coral Cladiella hirsuta. Their structures were elucidated by spectroscopic methods, particularly in 1D and 2D NMR experiments. The absolute configuration of 1 was determined by Mosher's method. Compounds 1, 5, and 6 have been shown to exhibit cytotoxicity toward several cancer cell lines. Compounds 2-4 and 8 were found to display significant in vitro anti-inflammatory activity in LPS-stimulated RAW264.7 macrophage cells by inhibiting the expression of the iNOS protein, with compound 2 also effectively reducing the level of COX-2 protein.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthozoa / chemistry*
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / isolation & purification*
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Cyclooxygenase 2 Inhibitors / chemistry
  • Cyclooxygenase 2 Inhibitors / isolation & purification*
  • Cyclooxygenase 2 Inhibitors / pharmacology
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Drug Screening Assays, Antitumor
  • Humans
  • Lipopolysaccharides / pharmacology*
  • Macrophages / drug effects*
  • Mice
  • Molecular Structure
  • Nitric Oxide Synthase Type II / antagonists & inhibitors
  • Nuclear Magnetic Resonance, Biomolecular

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Antineoplastic Agents
  • Cyclooxygenase 2 Inhibitors
  • Diterpenes
  • Lipopolysaccharides
  • eunicellin
  • Nitric Oxide Synthase Type II