Potential cancer chemopreventive constituents of the seeds of Dipteryx odorata (tonka bean)

J Nat Prod. 2003 May;66(5):583-7. doi: 10.1021/np020522n.

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.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Anticarcinogenic Agents / chemistry
  • Anticarcinogenic Agents / isolation & purification*
  • Anticarcinogenic Agents / pharmacology
  • Crystallography, X-Ray
  • Disease Models, Animal
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Drug Screening Assays, Antitumor
  • Enzyme Induction
  • Fabaceae / chemistry*
  • Inhibitory Concentration 50
  • Isoflavones / chemistry
  • Isoflavones / isolation & purification*
  • Isoflavones / pharmacology
  • Lignans / chemistry
  • Lignans / isolation & purification*
  • Lignans / pharmacology
  • Mammary Glands, Animal / drug effects
  • Mice
  • Molecular Conformation
  • Molecular Structure
  • NAD(P)H Dehydrogenase (Quinone) / biosynthesis
  • Nuclear Magnetic Resonance, Biomolecular
  • Organ Culture Techniques
  • Peru
  • Seeds / chemistry
  • Stereoisomerism
  • Tumor Cells, Cultured / drug effects

Substances

  • 5-methoxyxanthocercin A
  • Anticarcinogenic Agents
  • Diterpenes
  • Isoflavones
  • Lignans
  • dipteryxic acid
  • NAD(P)H Dehydrogenase (Quinone)