Two new naphthoquinone derivatives from the stem bark of Callicarpa maingayi

Nat Prod Commun. 2012 Oct;7(10):1333-6.

Abstract

Two new naphthoquinones designated as 3alpha-hydroxy-2-(2-hydroxypropan-2-yI)-9alpha-methoxy-2,3,3alpha,9alpha-tetra-hydronaphtho[2,3-b]furan-4,9-dione (callicarpa-quinone A, 1) and 5-hydroxy-2-(2-hydroxypropan-2-yl)naphtho[2,3-b]furan-4,9-dione (callicarpaquinone B, 2) were isolated from the chloroform fraction of Callicarpa maingayi. Three other known compounds, identified as avicequinone-C (3), wodeshiol (4) and paulownin (5), were reported for the first time from this species. The structure elucidation of compounds was established by comprehensive 1D and 2D NMR spectroscopic analyses as well as EIMS, UV and IR spectral data. Compounds 1 and 2 were tested in vitro for their cytotoxic activity against human breast cancer MCF-7cells. Compound 2 exhibited strong cytotoxic activity with an IC50 value of 1.9 +/- 0.2 microM, while 1 showed moderate activity with an IC50 value of 25.0 +/- 4.3 microM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Callicarpa / chemistry*
  • Chloroform
  • Drug Screening Assays, Antitumor
  • Magnetic Resonance Spectroscopy
  • Naphthoquinones / chemistry*
  • Naphthoquinones / isolation & purification
  • Naphthoquinones / pharmacology
  • Plant Bark / chemistry
  • Plant Extracts / chemistry
  • Plant Stems / chemistry
  • Solvents
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Tetrazolium Salts
  • Thiazoles

Substances

  • Antineoplastic Agents, Phytogenic
  • Naphthoquinones
  • Plant Extracts
  • Solvents
  • Tetrazolium Salts
  • Thiazoles
  • callicarpaquinone A
  • callicarpaquinone B
  • Chloroform
  • thiazolyl blue