Phenolic compounds obtained from stems of Couepia ulei with the potential to induce quinone reductase.
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.
Jang
Dae Sik
DS
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.
Park
Eun Jung
EJ
Kang
Young-Hwa
YH
Vigo
Jose Schunke
JS
Graham
James G
JG
Cabieses
Fernando
F
Fong
Harry H S
HH
Pezzuto
John M
JM
Kinghorn
A Douglas
AD
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
D010636:Phenols; D010936:Plant Extracts; D016660:NAD(P)H Dehydrogenase (Quinone)