Anti-inflammatory triterpenoids from the stems of Microtropis fokienensis

Molecules. 2014 Apr 14;19(4):4608-23. doi: 10.3390/molecules19044608.

Abstract

Three new ursane- and four new oleanane- type triterpenoids 1-7 were isolated, along with six known compounds 8-13, from the methanolic extract of Microtropis fokienensis. All structures were elucidated by mass and NMR spectroscopic methods. The isolates 4-10 and known compounds 14-17 that were previously isolated from this material were evaluated for anti-inflammatory activity based on effects against superoxide anion generation and elastase release by neutrophils in response to fMLP/CB. 11α,30-Dihydroxy-2,3-seco-olean-12-en-2,3-dioic anhydride (7) was the first triterpene anhydride from the genus of Microtropis to have the ring A expanded to a seven-membered ring; it showed significant anti-inflammatory activity against superoxide anion generation and elastase release. Unexpectedly, 30-hydroxy-2,3-seco-lup-20(29)-ene-2,3-dioic acid (17) showed the best effect against superoxide anion generation and elastase release with IC50 values of 0.06±0.01 and 1.03±0.35 µg/mL, respectively. Compound 17 had a dioic acid function, and compound 7 had an anhydride function modification in ring A; both showed promising activity in the target assays.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adult
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification*
  • Anti-Inflammatory Agents / pharmacology
  • Celastraceae / chemistry*
  • Humans
  • Methanol
  • Molecular Structure
  • Neutrophils / drug effects
  • Neutrophils / enzymology
  • Oleanolic Acid / analogs & derivatives
  • Oleanolic Acid / chemistry
  • Oleanolic Acid / isolation & purification
  • Oleanolic Acid / pharmacology
  • Pancreatic Elastase / antagonists & inhibitors
  • Pancreatic Elastase / metabolism
  • Plant Extracts / chemistry
  • Plant Stems / chemistry*
  • Solvents
  • Structure-Activity Relationship
  • Superoxides / antagonists & inhibitors
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification*
  • Triterpenes / pharmacology

Substances

  • Anti-Inflammatory Agents
  • Plant Extracts
  • Solvents
  • Triterpenes
  • oleanane
  • ursane
  • Superoxides
  • Oleanolic Acid
  • Pancreatic Elastase
  • Methanol