Nitrogen-containing phorbol esters from Croton ciliatoglandulifer and their effects on cyclooxygenases-1 and -2

J Nat Prod. 2006 Jun;69(6):887-90. doi: 10.1021/np0504311.

Abstract

Four new phorbol derivatives, 12-O-[(2R)-N,N-dimethyl-3-methylbutanoyl]-4-deoxyphorbol 13-acetate (1), 12-O-[(2S)-N,N-dimethyl-3-methylbutanoyl]-4-deoxyphorbol 13-acetate (2), 12-O-[3-methyl-2-butenoyl]-4-deoxyphorbol 13-acetate (3), and 12-O-[(2R)-N,N-dimethyl-3-methylbutanoyl]phorbol 13-acetate (4), along with six known compounds, were isolated from the aerial parts of Croton ciliatoglandulifer. An anti-inflammatory activity of a hexane extract of this plant was demonstrated against ear edema in mice produced by 12-O-tetradecanoylphorbol 13-acetate, and compounds 1, 4, and 3beta-O-acetyloleanolic acid (5) were active when evaluated against cyclooxygenases-1 and -2.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / isolation & purification*
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Croton / chemistry*
  • Cyclooxygenase 1 / drug effects
  • Cyclooxygenase 2 / drug effects
  • Cyclooxygenase 2 Inhibitors / chemistry
  • Cyclooxygenase 2 Inhibitors / isolation & purification*
  • Cyclooxygenase 2 Inhibitors / pharmacology
  • Disease Models, Animal
  • Ear
  • Edema / chemically induced
  • Edema / drug therapy
  • Mexico
  • Mice
  • Nitrogen / chemistry*
  • Phorbol Esters / chemistry
  • Phorbol Esters / isolation & purification*
  • Phorbol Esters / pharmacology
  • Plants, Medicinal / chemistry*
  • Tetradecanoylphorbol Acetate / pharmacology

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Cyclooxygenase 2 Inhibitors
  • Phorbol Esters
  • Cyclooxygenase 1
  • Cyclooxygenase 2
  • Nitrogen
  • Tetradecanoylphorbol Acetate