title: Potential cancer chemopreventive constituents of the seeds of Dipteryx odorata (tonka bean).
abstract: A new cassane diterpene, dipteryxic acid (1), and a new isoflavonolignan, 5-methoxyxanthocercin A (2), as well as four known active compounds, isoliquiritigenin (3), 6,4'-dihydroxy-3'-methoxyaurone (4), sulfuretin (5), and (+/-)-balanophonin (6), and five known inactive compounds, butin, eriodictyol, 7-hydroxychromone, 7,3'-dihydroxy-8,4'-dimethoxyisoflavone, and (-)-lariciresinol, were isolated from an ethyl acetate-soluble extract of the seeds of Dipteryx odorata, using a bioassay based on the induction of quinone reductase (QR) in cultured Hepa 1c1c7 mouse hepatoma cells to monitor chromatographic fractionation. The structures of compounds 1 and 2 were elucidated by spectroscopic data interpretation. Single-crystal X-ray diffraction analysis was used to confirm the relative stereochemistry of compound 1. Selected compounds (3-5) were evaluated in a mouse mammary organ culture assay, with isoliquiritigenin (3) found to exhibit 76% inhibition at a dose of 10 microg/mL.
authors.affiliation: Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 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; D016588:Anticarcinogenic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004195:Disease Models, Animal; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D004790:Enzyme Induction; D007887:Fabaceae / Q000737:chemistry*; D020128:Inhibitory Concentration 50; D007529:Isoflavones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D017705:Lignans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008321:Mammary Glands, Animal / Q000187:drug effects; D051379:Mice; D008968:Molecular Conformation; D015394:Molecular Structure; D016660:NAD(P)H Dehydrogenase (Quinone) / Q000096:biosynthesis; D019906:Nuclear Magnetic Resonance, Biomolecular; D009924:Organ Culture Techniques; D010568:Peru; D012639:Seeds / Q000737:chemistry; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured / Q000187:drug effects
chemical_list: C477992:5-methoxyxanthocercin A; D016588:Anticarcinogenic Agents; D004224:Diterpenes; D007529:Isoflavones; D017705:Lignans; C477991:dipteryxic acid; D016660:NAD(P)H Dehydrogenase (Quinone)