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: Dae Sik Jang, Eun Jung Park, Michael E Hawthorne, Jose Schunke Vigo, James G Graham, Fernando Cabieses, Bernard D Santarsiero, Andrew D Mesecar, Harry H S Fong, Rajendra G Mehta, John M Pezzuto, A Douglas Kinghorn
• Journal: Journal of natural products (J Nat Prod) Vol. 66 Issue 5 Pg. 583-7 (May 2003) ISSN: 0163-3864 [Print] United States
• PMID: 12762787 (Publication Type: Journal Article, Research Support, U.S. Gov't, P.H.S.)

Chemical References

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

Topics

• Animals
• Anticarcinogenic Agents (chemistry, isolation & purification, pharmacology)
• Crystallography, X-Ray
• Disease Models, Animal
• Diterpenes (chemistry, isolation & purification, pharmacology)
• Drug Screening Assays, Antitumor
• Enzyme Induction
• Fabaceae (chemistry)
• Inhibitory Concentration 50
• Isoflavones (chemistry, isolation & purification, pharmacology)
• Lignans (chemistry, isolation & purification, 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)