Potential cancer chemopreventive constituents of the seeds of Dipteryx odorata (tonka bean).
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.
Jang
Dae Sik
DS
Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, 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; 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
C477992:5-methoxyxanthocercin A; D016588:Anticarcinogenic Agents; D004224:Diterpenes; D007529:Isoflavones; D017705:Lignans; C477991:dipteryxic acid; D016660:NAD(P)H Dehydrogenase (Quinone)