Phenanthrenes, 9,10-dihydrophenanthrenes, bibenzyls with their derivatives, and malate or tartrate benzyl ester glucosides from tubers of Cremastra appendiculata

Phytochemistry. 2013 Oct:94:268-76. doi: 10.1016/j.phytochem.2013.06.001. Epub 2013 Jun 29.

Abstract

Eleven previously unknown compounds and 23 known compounds, including 20 phenanthrene or 9,10-dihydrophenanthrene derivatives, five bibenzyls, seven malate or tartrate benzyl ester glucosides, adenosine and gastrodin were isolated from tubers of Cremastra appendiculata. Among the obtained compounds, two are the first isolated dimers with one phenanthrene or bibenzyl unit connected to C-3 of 2,3,4,5-tetrahydro-phenanthro[2,1-b]furan moiety. In addition, 33 of these compounds were evaluated in vitro for their cytotoxic activity against two cancer cell lines. Among the compounds examined, one compound showed moderate cytotoxic activity, while five showed weak cytotoxic activity against the A549 cell line.

Keywords: 2,3,4,5-Tetrahydro-phenanthro[2,1-b]furan; 9,10-Dihydrophenanthrene; Bibenzyl; Cremastra appendiculata; Malate benzyl ester glucoside; Orchidaceae; Phenanthrene; Tartrate benzyl ester glucoside.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Benzene / chemistry
  • Bibenzyls / chemistry*
  • Bibenzyls / isolation & purification
  • Bibenzyls / pharmacology
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Esters / chemistry
  • Glucosides / chemistry*
  • Glucosides / isolation & purification
  • Glucosides / pharmacology
  • Humans
  • Magnetic Resonance Spectroscopy
  • Malates / chemistry
  • Orchidaceae / chemistry*
  • Phenanthrenes / chemistry*
  • Phenanthrenes / isolation & purification
  • Phenanthrenes / pharmacology
  • Plant Tubers / chemistry*
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Infrared
  • Tartrates / chemistry

Substances

  • Antineoplastic Agents, Phytogenic
  • Bibenzyls
  • Esters
  • Glucosides
  • Malates
  • Phenanthrenes
  • Tartrates
  • phenanthrene
  • malic acid
  • Benzene
  • tartaric acid