Potential Cancer Chemopreventive Constituents of the Seeds ofDipteryxodorata(Tonka Bean)

Journal of Natural Products
2003.0

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.

Knowledge Graph

Similar Paper

Potential Cancer Chemopreventive Constituents of the Seeds of<i>Dipteryx</i><i>o</i><i>dorata</i>(Tonka Bean)
Journal of Natural Products 2003.0
Potential Cancer Chemopreventive Flavonoids from the Stems of <i>Tephrosia toxicaria</i>
Journal of Natural Products 2003.0
Isolation and Characterization of Miscellaneous Secondary Metabolites of <i>Deprea </i><i>s</i><i>ubtriflora</i>
Journal of Natural Products 2003.0
Cytotoxic 3,20-Epoxy-<i>e</i><i>nt</i>-Kaurane Diterpenoids from <i>Isodon </i><i>e</i><i>riocalyx</i> var. <i>l</i><i>axiflora</i>
Journal of Natural Products 2002.0
Compounds from the Fruits of the Popular European Medicinal PlantVitex agnus-castusin Chemoprevention via NADP(H):Quinone Oxidoreductase Type 1 Induction
Evidence-Based Complementary and Alternative Medicine 2013.0
Caesalpins A–H, Bioactive Cassane-Type Diterpenes from the Seeds of <i>Caesalpinia minax</i>
Journal of Natural Products 2013.0
Structure and Cytotoxicity of Diterpenoids from <i>Isodon eriocalyx</i>
Journal of Natural Products 2010.0
Quinone Reductase Induction as a Biomarker for Cancer Chemoprevention
Journal of Natural Products 2006.0
Sesquiterpenoids from<i>Tithonia diversifolia</i>with Potential Cancer Chemopreventive Activity
Journal of Natural Products 2002.0
Compounds obtained fromSida acuta with the potential to induce quinone reductase and to inhibit 7,12-dimethylbenz-[a]anthracene-induced preneoplastic lesions in a mouse mammary organ culture model
Archives of Pharmacal Research 2003.0