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  • Title: Potential cancer chemopreventive constituents of the seeds of Dipteryx odorata (tonka bean).
    Author: Jang DS, Park EJ, Hawthorne ME, Vigo JS, Graham JG, Cabieses F, Santarsiero BD, Mesecar AD, Fong HH, Mehta RG, Pezzuto JM, Kinghorn AD.
    Journal: J Nat Prod; 2003 May; 66(5):583-7. PubMed ID: 12762787.
    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.
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