Taraxasterane- and ursane-type triterpenes from Nerium oleander and their biological activities

J Nat Prod. 2006 Aug;69(8):1164-7. doi: 10.1021/np0680073.

Abstract

Two new taraxasterane-type triterpenes, 20beta,28-epoxy-28alpha-methoxytaraxasteran-3beta-ol (1) and 20beta,28-epoxytaraxaster-21-en-3beta-ol (2), were isolated from an ethyl acetate extract of the leaves of Nerium oleander, together with ursane-type triterpenes, 28-nor-urs-12-ene-3beta,17beta-diol (3) and 3beta-hydroxyurs-12-en-28-aldehyde (4). The structures of 1 and 2 were established on the basis of their spectroscopic data. Anti-inflammatory activity of 1-4 was examined on the basis of inhibitory activity against the induction of intercellular adhesion molecule-1 (ICAM-1). Cytotoxic activity of 1-4 was evaluated against four human cell lines, A-549, WI-38, VA-13, and HepG2 cells.

MeSH terms

  • Anti-Inflammatory Agents, Non-Steroidal* / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal* / classification
  • Anti-Inflammatory Agents, Non-Steroidal* / isolation & purification
  • Anti-Inflammatory Agents, Non-Steroidal* / pharmacology
  • Antineoplastic Agents, Phytogenic* / chemistry
  • Antineoplastic Agents, Phytogenic* / classification
  • Antineoplastic Agents, Phytogenic* / isolation & purification
  • Antineoplastic Agents, Phytogenic* / pharmacology
  • Drug Screening Assays, Antitumor
  • Humans
  • Intercellular Adhesion Molecule-1 / drug effects
  • Japan
  • Molecular Structure
  • Nerium / chemistry*
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry
  • Plants, Medicinal / chemistry*
  • Triterpenes* / chemistry
  • Triterpenes* / classification
  • Triterpenes* / isolation & purification
  • Triterpenes* / pharmacology
  • Tumor Cells, Cultured

Substances

  • 20beta,28-epoxy-28alpha-methoxytaraxasteran-3beta-ol
  • 20beta,28-epoxytaraxaster-21-en-3beta-ol
  • Anti-Inflammatory Agents, Non-Steroidal
  • Antineoplastic Agents, Phytogenic
  • Triterpenes
  • Intercellular Adhesion Molecule-1