Identification of Two New Phenanthrenes from Dendrobii Herba and Their Cytotoxicity towards Human Hypopharynx Squamous Carcinoma Cell (FaDu)

Molecules. 2019 Jun 25;24(12):2339. doi: 10.3390/molecules24122339.

Abstract

Two new phenanthrenes, (1R,2R)-1,7-hydroxy-2,8-methoxy-2,3-dihydrophenanthrene-4(1H)-one (1) and 2,7-dihydroxy-phenanthrene-1,4-dione (2), were isolated from the ethyl acetate-soluble fraction of Dendrobii Herba, together with seven known phenanthrenes (3-9), two bibenzyls (10-12), and a lignan (13). Structures of 1 and 2 were elucidated by analyzing one-dimensional (1D) and two-dimensional (2D)-NMR and High-resolution electrospray ionization mass spectra (HR-ESI-MS) data. The absolute configuration of compound 1 was confirmed by the circular dichroism (CD) spectroscopic method. In cytotoxicity assay using FaDu human hypopharynx squamous carcinoma cell line, compounds 3-6, 8, 10, and 12 showed activities, with IC50 values that ranged from 2.55 to 17.70 μM.

Keywords: (1R,2R)-1,7-hydroxy-2,8-methoxy-2,3-dihydrophenanthrene-4(1H)-one; 2,7-dihydroxy-phenanthrene-1,4-dione; Dendrobii Herba; FaDu human hypopharynx squamous carcinoma cell; cytotoxicity.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Carcinoma, Squamous Cell
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Humans
  • Hypopharyngeal Neoplasms
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Orchidaceae / chemistry*
  • Phenanthrenes / chemistry
  • Phenanthrenes / pharmacology*
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents, Phytogenic
  • Phenanthrenes
  • Plant Extracts
  • phenanthrene