title: Constituents of Musa x paradisiaca cultivar with the potential to induce the phase II enzyme, quinone reductase.
abstract: A new bicyclic diarylheptanoid, rel-(3S,4aR,10bR)-8-hydroxy-3-(4-hydroxyphenyl)-9-methoxy-4a,5,6,10b-tetrahydro-3H-naphtho[2,1-b]pyran (1), as well as four known compounds, 1,2-dihydro-1,2,3-trihydroxy-9-(4-methoxyphenyl)phenalene (2), hydroxyanigorufone (3), 2-(4-hydroxyphenyl)naphthalic anhydride (4), and 1,7-bis(4-hydroxyphenyl)hepta-4(E),6(E)-dien-3-one (5), were isolated from an ethyl acetate-soluble fraction of the methanol extract of the fruits of Musa x paradisiaca cultivar, using a bioassay based on the induction of quinone reductase (QR) in cultured Hepa1c1c7 mouse hepatoma cells to monitor chromatographic fractionation. The structure and relative stereochemistry of compound 1 were elucidated unambiguously by one- and two-dimensional NMR experiments ((1)H NMR, (13)C NMR, DEPT, COSY, HMQC, HMBC, and NOESY) and single-crystal X-ray diffraction analysis. Isolates 1-5 were evaluated for their potential cancer chemopreventive properties utilizing an in vitro assay to determine quinone reductase induction and a mouse mammary organ culture assay.
authors.affiliation: Program for Collaborative Research in the Pharmaceutical Sciences, Department of Medicinal Chemistry and Pharmacognosy, and Center for Pharmaceutical Biotechnology, College of Pharmacy, Chicago, Illinois 60612, USA.
authors.forename: Dae Sik
authors.initials: DS
authors.lastname: Jang
authors.forename: Eun Jung
authors.initials: EJ
authors.lastname: Park
authors.forename: Michael E
authors.initials: ME
authors.lastname: Hawthorne
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: Bernard D
authors.initials: BD
authors.lastname: Santarsiero
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Mesecar
authors.forename: Harry H S
authors.initials: HH
authors.lastname: Fong
authors.forename: Rajendra G
authors.initials: RG
authors.lastname: Mehta
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 / Q000201:enzymology; D004790:Enzyme Induction; D005260:Female; D008114:Liver Neoplasms, Experimental / Q000201:enzymology; D008325:Mammary Neoplasms, Experimental / Q000201:enzymology*; D051379:Mice; D008807:Mice, Inbred BALB C; D028521:Musa / Q000737:chemistry*; D016660:NAD(P)H Dehydrogenase (Quinone) / Q000096:biosynthesis*; D010936:Plant Extracts / Q000494:pharmacology*; D014407:Tumor Cells, Cultured
chemical_list: D010936:Plant Extracts; D016660:NAD(P)H Dehydrogenase (Quinone)