Chemistry of the chippiine/dippinine/tronocarpine class of indole alkaloids

Alkaloids Chem Biol. 2021:85:177-222. doi: 10.1016/bs.alkal.2020.07.001. Epub 2020 Sep 2.

Abstract

The chippiines/dippinines/tronocarpine are a family of biologically and structurally interesting polycyclic tryptamine-derived indole alkaloids isolated from the leaf and bark extracts of plants belonging to the Tabernaemontana genus. To date, 14 members of this family have been isolated and characterized. This review discusses the isolation, structure determination, biological activity, and proposed biosynthesis of these metabolites. In addition, synthetic studies on the alkaloids are described including approaches to tronocarpine and dippinine B core intermediates and total syntheses of (+)-dippinine B and (+)-tronocarpine.

Keywords: Anticarcinogenic activity; Biogenesis; Enantioselective synthesis; Indole alkaloids; Isolation; Total synthesis.

Publication types

  • Review

MeSH terms

  • Alkaloids
  • Azepines / chemistry*
  • Cell Line, Tumor
  • Humans
  • Indole Alkaloids / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Neoplasms / drug therapy
  • Plant Bark / metabolism
  • Plant Extracts / pharmacology
  • Plant Leaves / metabolism
  • Plants
  • Tabernaemontana / metabolism*

Substances

  • Alkaloids
  • Azepines
  • Indole Alkaloids
  • Plant Extracts
  • tronocarpine