Activity-guided isolation of novel norwithanolides from depreasubtriflora with potential cancer chemopreventive activity.
Activity-monitored fractionation of a CHCl(3)-soluble extract of Deprea subtriflora using a quinone reductase induction assay led to the purification of subtrifloralactones A-J (1-10), 10 novel C-18 norwithanolides based on a new C(27) skeleton. These compounds were characterized by spectroscopic and chemical studies, and single-crystal X-ray diffraction analysis was used to confirm the structures of 1 and 4. Compounds 1-10 were evaluated for their cancer chemopreventive activity in terms of their ability to induce quinone reductase activity with cultured murine hepatoma cells, and compounds 1 and 6 were found to be highly effective.
Su
Bao-Ning
BN
Program for Collaborative Research in the Pharmaceutical Sciences, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, Illinois 60612, USA.
Park
Eun Jung
EJ
Nikolic
Dejan
D
Santarsiero
Bernard D
BD
Mesecar
Andrew D
AD
Vigo
Jose Schunke
JS
Graham
James G
JG
Cabieses
Fernando
F
van Breemen
Richard B
RB
Fong
Harry H S
HH
Farnsworth
Norman R
NR
Pezzuto
John M
JM
Kinghorn
A Douglas
AD
D000818:Animals; D016588:Anticarcinogenic Agents; D006528:Carcinoma, Hepatocellular; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D051379:Mice; D008968:Molecular Conformation; D015394:Molecular Structure; D016660:NAD(P)H Dehydrogenase (Quinone) / Q000378:metabolism; D019906:Nuclear Magnetic Resonance, Biomolecular; D010568:Peru; D010946:Plants, Medicinal / Q000737:chemistry*; D019657:Solanaceae / Q000737:chemistry*; D014407:Tumor Cells, Cultured / Q000187:drug effects
D016588:Anticarcinogenic Agents; D007783:Lactones; D016660:NAD(P)H Dehydrogenase (Quinone)