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

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.

• Authors: Jian-Qiao Gu, Eun Jung Park, Jose Schunke Vigo, James G Graham, Harry H S Fong, John M Pezzuto, A Douglas Kinghorn
• Journal: Journal of natural products (J Nat Prod) Vol. 65 Issue 11 Pg. 1616-20 (Nov 2002) ISSN: 0163-3864 [Print] United States
• PMID: 12444686 (Publication Type: Journal Article, Research Support, U.S. Gov't, P.H.S.)

Chemical References

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

Topics

• Animals
• Antineoplastic Agents, Phytogenic (chemistry, isolation & purification, pharmacology)
• Carcinoma, Hepatocellular
• Chalcone (analogs & derivatives, chemistry, isolation & purification, 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)