Ylangene-type and nardosinane-type sesquiterpenoids from the soft corals Lemnalia flava and Paralemnalia thyrsoides

Chem Pharm Bull (Tokyo). 2010 Mar;58(3):381-5. doi: 10.1248/cpb.58.381.

Abstract

Chemical investigations of the Formosan soft coral Lemnalia flava have obtained a new ylangene-type sesquiterpenoid, (1S,2S,4R,6S,7R,8S)-4alpha-formyloxy-beta-ylangene (1), along with two known sesquiterpenoids, lemnalol (2) and isolemnalol (3). Three new nardosinane-type sesquiterpenoids, designated as paralemnolins J-L (4-6), and five known sesquiterpenoids (7-11), were isolated from the other soft coral Paralemnalia thyrsoides. The structures of metabolites 1 and 4-6 were elucidated through extensive spectroscopic analysis and chemical methods. Moreover, the anti-inflammatory activity of metabolites 1-7 and 11 was evaluated in vitro.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthozoa / chemistry*
  • Anthozoa / metabolism
  • Anti-Inflammatory Agents / chemistry*
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology
  • Cyclooxygenase 2 / metabolism
  • Gene Expression Regulation, Enzymologic / drug effects
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Macrophages / enzymology
  • Mice
  • Models, Molecular
  • Molecular Conformation
  • Nitric Oxide Synthase Type II / antagonists & inhibitors
  • Nitric Oxide Synthase Type II / metabolism
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology
  • Species Specificity
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • (1S,2S,4R,6S,7R,8S)-4alpha-formyloxy-beta-ylangene
  • Anti-Inflammatory Agents
  • Lipopolysaccharides
  • Sesquiterpenes
  • Nitric Oxide Synthase Type II
  • Cyclooxygenase 2