title: Phenolic compounds obtained from stems of Couepia ulei with the potential to induce quinone reductase.
abstract: Activity-guided fractionation of the EtOAc-soluble extract of the stems of Couepia ulei, using a bioassay based on the induction of quinone reductase (QR) in cultured Hepa 1c1c7 mouse hepatoma cells led to the isolation of two active compounds, a new natural product, erythro-2,3-bis(4-hydroxy-3-methoxyphenyl)-3-ethoxypropan-1-ol (1), and a known compound, evofolin-B (2), along with five inactive compounds all of known structure, viz., betulinic acid, oleanolic acid, pomolic acid, (+/-)-syringaresinol, and ursolic acid. These isolates were identified by analysis of physical and spectral data. Compounds 1 and 2 exhibited QR inducing activity, with observed CD (concentration required to double induction) values of 16.7 and 16.4 microM, respectively.
authors.affiliation: Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, USA.
authors.forename: Dae Sik
authors.initials: DS
authors.lastname: Jang
authors.forename: Eun Jung
authors.initials: EJ
authors.lastname: Park
authors.forename: Young-Hwa
authors.initials: YH
authors.lastname: Kang
authors.forename: Jose Schunke
authors.initials: JS
authors.lastname: Vigo
authors.forename: James G
authors.initials: JG
authors.lastname: Graham
authors.forename: Fernando
authors.initials: F
authors.lastname: Cabieses
authors.forename: Harry H S
authors.initials: HH
authors.lastname: Fong
authors.forename: John M
authors.initials: JM
authors.lastname: Pezzuto
authors.forename: A Douglas
authors.initials: AD
authors.lastname: Kinghorn
mesh_terms: D000818:Animals; D006528:Carcinoma, Hepatocellular / Q000188:drug therapy; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002855:Chromatography, Thin Layer; D004790:Enzyme Induction / Q000187:drug effects; D051379:Mice; D016660:NAD(P)H Dehydrogenase (Quinone) / Q000096:biosynthesis*; D010636:Phenols / Q000302:isolation & purification* / Q000494:pharmacology*; D010936:Plant Extracts / Q000494:pharmacology; D018547:Plant Stems / Q000737:chemistry; D027824:Rosaceae / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D010636:Phenols; D010936:Plant Extracts; D016660:NAD(P)H Dehydrogenase (Quinone)