Quassilactones A and B, structural characterization of a new class of norquassinoids from Brucea javanica

J Nat Med. 2020 Jun;74(3):599-605. doi: 10.1007/s11418-020-01407-8. Epub 2020 Apr 11.

Abstract

Two novel norquassinoids possessing a unique ketal skeleton, designated quassilactones A (1) and B (2), were isolated from the fruits of Brucea javanica (Simaroubaceae). Their structures were established by extensive NMR and HR-ESI-MS spectroscopic analysis. The absolute configuration of 1 was determined through single-crystal X-ray crystallography, and that of 2 was assigned by comparing the calculated electronic and experimental circular dichroism with compound 1. In addition, their cytotoxic activities against three human cancer cell lines and their antimicrobial activities were evaluated.

Keywords: Brucea javanica; Norquassinoid; Quassilactone; X-ray crystallography.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Bacteria / drug effects*
  • Brucea / chemistry*
  • Cell Line
  • Crystallography, X-Ray
  • Fruit / chemistry
  • Humans
  • Molecular Structure
  • Neoplasms / drug therapy
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Quassins / chemistry*
  • Quassins / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Plant Extracts
  • Quassins
  • quassilactone