Phenanthrene derivatives from Cymbidium Great Flower Marie Laurencin and their biological activities

J Nat Prod. 2012 Apr 27;75(4):605-9. doi: 10.1021/np200788u. Epub 2012 Mar 9.

Abstract

A new phenanthrendione, ephemeranthoquinone B (1), two phenanthrenes, marylaurencinols A (2) and B (3), and a phenanthrene glucoside, marylaurencinoside A (4), were isolated from the roots of Cymbidium Great Flower Marie Laurencin, along with six known phenanthrenes, 5-10. The structures of these compounds were established by a combination of extensive NMR spectroscopy and/or X-ray crystallographic analysis and chemical degradation. The compounds were tested for antibacterial activities against Bacillus subtilis and Klebsiella pneumoniae and for cytotoxic activity against the human promyelocytic leukemia (HL-60) cell line. Compounds 1, 3, and 6 showed antibacterial activities with minimum inhibitory concentration (MIC) values in the range of 4.88 to 65.10 μM. Notably, ephemeranthoquinone B (1) had a strong antibacterial effect on B. subtilis. Furthermore, 1 exhibited moderate cytotoxic activity (IC(50) 2.8 μM) against HL-60 cells. Compounds 4-9 also showed weak cytotoxic activity against the HL-60 cell line with IC(50) values of 19.3-52.4 μM.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • HL-60 Cells
  • Humans
  • Inhibitory Concentration 50
  • Japan
  • Molecular Conformation
  • Molecular Structure
  • Orchidaceae / chemistry*
  • Phenanthrenes / chemistry
  • Phenanthrenes / isolation & purification*
  • Phenanthrenes / pharmacology*
  • Plant Roots / chemistry

Substances

  • Antineoplastic Agents, Phytogenic
  • Phenanthrenes
  • ephemeranthoquinone B