Eleucanainones A and B: Two Dimeric Structures from the Bulbs of Eleutherine americana with Anti-MRSA Activity

Org Lett. 2020 May 1;22(9):3449-3453. doi: 10.1021/acs.orglett.0c00903. Epub 2020 Apr 15.

Abstract

Two naphthoquinone-derived heterodimers with unprecedented carbon skeletons, eleucanainones A (1) and B (2), were isolated from the bulbs of Eleutherine americana. Their structures were elucidated by comprehensive spectroscopic methods. The structures of 1 and 2 were determined to be the first examples of dibenzofuran- and naphthalenone-containing naphthoquinone dimers. Compound 1 exhibited significant anti-MRSA activity in vitro with minimum inhibitory concentration (MIC) values of 0.78 μg/mL by downregulation of basal expression of agrA, cidA, icaA and sarA in methicillin-resistant S. aureus (MRSA).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Diketopiperazines / chemistry*
  • Diketopiperazines / isolation & purification
  • Diketopiperazines / pharmacology*
  • Gene Expression / drug effects
  • Iridaceae / chemistry*
  • Methicillin-Resistant Staphylococcus aureus / drug effects*
  • Methicillin-Resistant Staphylococcus aureus / genetics
  • Methicillin-Resistant Staphylococcus aureus / metabolism
  • Microbial Sensitivity Tests
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology
  • Spectrophotometry, Ultraviolet

Substances

  • Anti-Bacterial Agents
  • Diketopiperazines
  • Plant Extracts
  • eleutherazine A
  • eleutherazine B