Constituents of Musa x paradisiaca cultivar with the potential to induce the phase II enzyme, quinone reductase.
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.
Jang
Dae Sik
DS
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.
Park
Eun Jung
EJ
Hawthorne
Michael E
ME
Vigo
Jose Schunke
JS
Graham
James G
JG
Cabieses
Fernando
F
Santarsiero
Bernard D
BD
Mesecar
Andrew D
AD
Fong
Harry H S
HH
Mehta
Rajendra G
RG
Pezzuto
John M
JM
Kinghorn
A Douglas
AD
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
D010936:Plant Extracts; D016660:NAD(P)H Dehydrogenase (Quinone)