Scopariusic acid, a new meroditerpenoid with a unique cyclobutane ring isolated from Isodon scoparius

Org Lett. 2013 Sep 6;15(17):4446-9. doi: 10.1021/ol401991u. Epub 2013 Aug 14.

Abstract

Scopariusic acid (1), a new ent-clerodane-based meroditerpenoid with a unique cyclobutane ring and an unusual 1-octen-3-ol substituent, together with its biosynthetic related compound 2, were isolated from the aerial parts of Isodon scoparius. The structures of 1 and 2, including their absolute configurations, were determined by spectroscopic methods, single-crystal X-ray diffraction analysis, and chemical methods. Compound 1 showed weak cytotoxicity and moderate immunosuppressive activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Crystallography, X-Ray
  • Diterpenes, Kaurane / chemistry*
  • Diterpenes, Kaurane / isolation & purification*
  • Diterpenes, Kaurane / pharmacology
  • Drug Screening Assays, Antitumor
  • Female
  • HL-60 Cells
  • Humans
  • Immunosuppressive Agents / chemistry*
  • Immunosuppressive Agents / isolation & purification*
  • Immunosuppressive Agents / pharmacology
  • Isodon / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular

Substances

  • Antineoplastic Agents, Phytogenic
  • Diterpenes, Kaurane
  • Immunosuppressive Agents
  • scopariusic acid