Antimicrobial and Cytotoxic Angucyclic Quinones from Actinomadura miaoliensis

J Nat Prod. 2021 Nov 26;84(11):2775-2785. doi: 10.1021/acs.jnatprod.1c00232. Epub 2021 Nov 8.

Abstract

Eight new angucyclic quinones, miaosporones A to H (1-8), along with the previously described metabolites 8-hydroxy-3-methylbenz[a]anthraquinone (9), tetrangulol (10), 5,6-dihydro-1,8-dihydroxy-3-methybenz[a]anthracene-7,12-quinone (11), and SF2315A (12), were isolated from the terrestrial actinomycete Actinomadura miaoliensis TBRC 5172 obtained from sediment collected from the Huai Yang reservoir, Prachuap Khiri Khan Province, Thailand. The relative and absolute configurations of the new compounds were determined from analysis of NMR spectroscopic and X-ray crystallographic data. Miaosporone A exhibited antimalarial activity against Plasmodium falciparum K1 and antibacterial activity against Mycobacterium tuberculosis with respective IC50 values of 2.5 and 2.4 μM and displayed cytotoxic activities against both cancerous (MCF-7 and NCI-H187) and nonmalignant (Vero) cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Actinomadura / metabolism*
  • Anti-Infective Agents / isolation & purification*
  • Anti-Infective Agents / pharmacology
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Humans
  • Magnetic Resonance Spectroscopy
  • Mycobacterium tuberculosis / drug effects
  • Plasmodium falciparum / drug effects
  • Quinolones / chemistry
  • Quinolones / isolation & purification*
  • Quinolones / pharmacology

Substances

  • Anti-Infective Agents
  • Antineoplastic Agents
  • Quinolones

Supplementary concepts

  • Actinomadura miaoliensis