Antimicrobial and cytotoxic juglones from the immature exocarps of Juglans mandshurica

Nat Prod Res. 2019 Nov;33(22):3203-3209. doi: 10.1080/14786419.2018.1468326. Epub 2018 May 4.

Abstract

Juglonols A-C (1-3), three new juglone derivatives possessing a hydroxyethyl side chain, were isolated from an organic extract of the immature exocarps of Juglans mandshurica together with five known tetralones (4-8). Their structures were elucidated by extensive spectroscopic analyses and comparison with literature data. The new juglone derivatives exhibited inhibitory activities towards a panel of bacteria and fungi, as well as cancer cell lines. In contrast, the known tetralone homologues (4-8) appeared to be much less efficacy.

Keywords: juglone; juglonols A−C; tetralone.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Anti-Infective Agents / isolation & purification*
  • Anti-Infective Agents / pharmacology
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology
  • Cell Line
  • Humans
  • Juglans / chemistry*
  • Molecular Structure
  • Naphthoquinones / isolation & purification
  • Naphthoquinones / pharmacology*
  • Naphthoquinones / toxicity
  • Plant Extracts / chemistry*
  • Plant Extracts / pharmacology
  • Spectrum Analysis / methods
  • Tetralones / isolation & purification
  • Tetralones / pharmacology

Substances

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antifungal Agents
  • Antineoplastic Agents
  • Naphthoquinones
  • Plant Extracts
  • Tetralones
  • juglone