Potential Cancer Chemopreventive Constituents of the Seeds of Dipteryx odorata (Tonka Bean)
| Autor: | James G. Graham, Jose Schunke Vigo, A. Douglas Kinghorn, Harry H. S. Fong, Andrew D. Mesecar, Rajendra G. Mehta, Michael E. Hawthorne, John M. Pezzuto, Dae Sik Jang, Eun Jung Park, Bernard D. Santarsiero, Fernando Cabieses |
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| Rok vydání: | 2003 |
| Předmět: |
Molecular Conformation
Pharmaceutical Science Pharmacognosy Crystallography X-Ray Lignans Analytical Chemistry Inhibitory Concentration 50 Mice chemistry.chemical_compound Mammary Glands Animal Organ Culture Techniques Peru Drug Discovery NAD(P)H Dehydrogenase (Quinone) Tumor Cells Cultured Animals Anticarcinogenic Agents Nuclear Magnetic Resonance Biomolecular Pharmacology Lignan Molecular Structure Traditional medicine biology Organic Chemistry Fabaceae Stereoisomerism Eriodictyol biology.organism_classification Isoflavones Terpenoid Quinone Disease Models Animal Dipteryx Complementary and alternative medicine chemistry Biochemistry Enzyme Induction Seeds Molecular Medicine Diterpenes Drug Screening Assays Antitumor Diterpene Isoliquiritigenin |
| Zdroj: | Journal of Natural Products. 66:583-587 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/np020522n |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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