Calophyline A, a new rearranged monoterpenoid indole alkaloid from Winchia calophylla

Org Lett. 2012 Jul 6;14(13):3450-3. doi: 10.1021/ol301400e. Epub 2012 Jun 8.

Abstract

Calophyline A (1), a novel unprecedented rearranged monoterpenoid indole alkaloid, along with a new natural product N-methyl aspidodasycarpine (2) and six known analogues, was isolated from the trunk barks of Winchia calophylla. The structure of compound 1 was elucidated on the basis of spectroscopic data and then confirmed by a single-crystal X-ray crystallographic analysis. A hypothetical biogenetic pathway for compound 1 was proposed. All isolated compounds were evaluated for their in vitro cytotoxicity against a small panel of human cancer cell lines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Apocynaceae / chemistry*
  • Cell Line, Tumor
  • Crystallography, X-Ray
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • Models, Molecular
  • Molecular Conformation
  • Plant Bark / chemistry
  • Plant Extracts / chemistry
  • Secologanin Tryptamine Alkaloids / chemistry
  • Secologanin Tryptamine Alkaloids / isolation & purification
  • Secologanin Tryptamine Alkaloids / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents, Phytogenic
  • Plant Extracts
  • Secologanin Tryptamine Alkaloids
  • calophyline A