Pegaharmols A-B, Axially Chiral β-Carboline-quinazoline Dimers from the Roots of Peganum harmala

Org Lett. 2020 Oct 2;22(19):7522-7525. doi: 10.1021/acs.orglett.0c02709. Epub 2020 Sep 16.

Abstract

Two nonbiaryl axially chiral β-carboline-quinazoline dimers, pegaharmols A (1) and B (2), were isolated from the roots of Peganum harmala. Their planar structures were elucidated by the spectroscopic methods of high-resolution mass spectrometry and 1D and 2D nuclear magnetic resonance (NMR). The stereochemistry was established by a comparison between the experimental data of NMR and electronic circular dichroism and the computed data by quantum mechanical calculations. It is discovered for the first time that the β-carboline at the C-8 position is bonded to the vasicine at the C-9 position. 1 exhibited moderate cytotoxic activity against HL-60 and A549 cell lines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Carbolines / chemistry
  • Carbolines / isolation & purification
  • Carbolines / pharmacology*
  • Drug Screening Assays, Antitumor
  • HL-60 Cells
  • Humans
  • Molecular Structure
  • Peganum / chemistry*
  • Plant Extracts / chemistry
  • Plant Roots / chemistry*
  • Quinazolines / chemistry*

Substances

  • Alkaloids
  • Antineoplastic Agents, Phytogenic
  • Carbolines
  • Plant Extracts
  • Quinazolines
  • vasicine
  • norharman