Bulbinelonesides A-E, phenylanthraquinone glycosides from the roots of Bulbinella floribunda

J Nat Prod. 2003 Jun;66(6):894-7. doi: 10.1021/np030061l.

Abstract

The roots of Bulbinella floribunda have been analyzed for the phenolic constituents, resulting in the isolation of five new phenylanthraquinone glycosides, named bulbinelonesides A-E (1-5), along with two known phenylanthraquinones, (+)-M-knipholone (6) and (+)-M-isoknipholone (7). The structures of the new compounds were determined on the basis of extensive spectroscopic analysis, including 2D NMR, and the results of enzymatic hydrolysis. Although the new compounds 3-5, whose absolute stereochemistry of the unsymmetric biaryl moiety was determined to be P by the CD spectrum, did not show apparent cytotoxicity against cultured HSC-2 tumor cells and HPC normal cells, the new compounds 1 and 2, as well as the known compounds 6 and 7, whose biaryl bond was assigned as M, exhibited a tumor-specific cytotoxicity against HSC-2 cells comparable to or slightly weaker than etoposide, used as a positive control.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthraquinones / chemistry
  • Anthraquinones / isolation & purification*
  • Anthraquinones / pharmacology
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Carcinoma, Squamous Cell
  • Cells, Cultured / drug effects
  • Circular Dichroism
  • Drug Screening Assays, Antitumor
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology
  • Humans
  • Inhibitory Concentration 50
  • Japan
  • Liliaceae / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Roots / chemistry
  • Plants, Medicinal / chemistry*
  • Stereoisomerism
  • Tumor Cells, Cultured / drug effects

Substances

  • Anthraquinones
  • Antineoplastic Agents, Phytogenic
  • Glycosides