Bioactive dihydronaphthoquinone derivatives from Fusarium solani

J Nat Prod. 2014 Sep 26;77(9):1992-6. doi: 10.1021/np500175j. Epub 2014 Aug 28.

Abstract

New dihydronaphthoquinone derivatives, karuquinone A (1), karuquinone B (2), and karuquinone C (3), were isolated from a fungal culture broth of Fusarium solani. The structures were determined by interpretation of spectroscopic data (1D/2D NMR, MS, and IR). Three known compounds, javanicin (4), 2,3-dihydro-5-hydroxy-8-methoxy-2,4-dimethylnaphtho[1,2-b]furan-6,9-dione (5), and 5-hydroxydihydrofusarubin C (6), were also isolated. The six isolated compounds were tested for cytotoxicity against three human cancer cell lines and a human umbilical vein endothelial cell (HUVEC) line. Of these, karuquinone A exhibited the strongest cytotoxic activity. Karuquinone B did not affect the proliferation of the cancer cell lines but did inhibit the proliferation of HUVEC. Additionally, we demonstrated that karuquinone A induces apoptosis in cancer cells through the generation of reactive oxygen species (ROS).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology*
  • Apoptosis / drug effects
  • Drug Screening Assays, Antitumor
  • Fusarium / chemistry*
  • HeLa Cells
  • Humans
  • Molecular Structure
  • Naphthoquinones / chemistry
  • Naphthoquinones / isolation & purification*
  • Naphthoquinones / pharmacology*
  • Reactive Oxygen Species / metabolism

Substances

  • Antineoplastic Agents
  • Naphthoquinones
  • Reactive Oxygen Species
  • karuquinone A
  • karuquinone B
  • karuquinone C
  • hydroxydihydrofusarubin