Activity-guided isolation of constituents of Renealmia nicolaioides with the potential to induce the phase II enzyme quinone reductase

J Nat Prod. 2002 Nov;65(11):1616-20. doi: 10.1021/np020249p.

Abstract

Three new prenylated dihydrochalcones, (+/-)-nicolaioidesins A, B, and C (1-3), as well as a new natural product, 5-styrylfuran-2-carboxylic acid methyl ester (4), along with four known compounds, 2'-hydroxy-4',6'-dimethoxychalcone (5), (+/-)-5-hydroxy-7-methoxyflavanone (6), (+/-)-5-hydroxy-7,4'-dimethoxyflavanone, and panduratin A, were isolated from the roots of Renealmia nicolaioides, using a bioassay to determine the induction of quinone reductase (QR) activity with cultured Hepa lclc7 mouse hepatoma cells. Among these isolates, 5 and 6 induced QR activity, with observed concentrations to double activity (CD) values of 1.7 and 0.9 microg/mL, respectively, while the other constituents were not regarded as being active (CD >10 microg/mL). The chemical structures of 1-4 were elucidated by spectroscopic methods. A biogenetic pathway for the formation of (+/-)-nicolaioidins A-C (1-3) is proposed.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Carcinoma, Hepatocellular
  • Chalcone / analogs & derivatives
  • Chalcone / chemistry
  • Chalcone / isolation & purification*
  • Chalcone / pharmacology
  • Chalcones
  • Chromatography, High Pressure Liquid
  • Drug Screening Assays, Antitumor
  • Inhibitory Concentration 50
  • Mice
  • Molecular Conformation
  • Molecular Structure
  • NAD(P)H Dehydrogenase (Quinone) / metabolism
  • Peru
  • Plant Roots / chemistry
  • Plants, Medicinal / chemistry*
  • Structure-Activity Relationship
  • Tumor Cells, Cultured / drug effects
  • Zingiberaceae / chemistry*

Substances

  • Antineoplastic Agents, Phytogenic
  • Chalcones
  • nicolaioidesin A
  • nicolaioidesin B
  • nicolaioidesin C
  • Chalcone
  • NAD(P)H Dehydrogenase (Quinone)