Activity-guided isolation of constituents of Renealmia nicolaioides with the potential to induce the phase II enzyme quinone reductase.
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.
Gu
Jian-Qiao
JQ
Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, Chicago, Illinois 60612, USA.
Park
Eun Jung
EJ
Vigo
Jose Schunke
JS
Graham
James G
JG
Fong
Harry H S
HH
Pezzuto
John M
JM
Kinghorn
A Douglas
AD
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006528:Carcinoma, Hepatocellular; D002599:Chalcone / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D047188:Chalcones; D002851:Chromatography, High Pressure Liquid; D004354:Drug Screening Assays, Antitumor; D020128:Inhibitory Concentration 50; D051379:Mice; D008968:Molecular Conformation; D015394:Molecular Structure; D016660:NAD(P)H Dehydrogenase (Quinone) / Q000378:metabolism; D010568:Peru; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured / Q000187:drug effects; D030521:Zingiberaceae / Q000737:chemistry*
D000972:Antineoplastic Agents, Phytogenic; D047188:Chalcones; C471529:nicolaioidesin A; C471530:nicolaioidesin B; C471531:nicolaioidesin C; D002599:Chalcone; D016660:NAD(P)H Dehydrogenase (Quinone)