Cytotoxic Flavone Analogues of Vitexicarpin, a Constituent of the Leaves of Vitex negundo
| Autor: | Daniel Chávez, Hee Byung Chai, Qiuwen Mi, John M. Pezzuto, Soedarsono Riswan, Dongho Lee, Geoffrey A. Cordell, Fredyc Diaz, Leonardus B.S. Kardono, A. Douglas Kinghorn, Ghee Teng Tan, Craig R. Fairchild, Norman R. Farnsworth, Robert A. Wild |
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| Rok vydání: | 2003 |
| Předmět: |
Male
Lung Neoplasms Vitex negundo Stereochemistry Acylation Flavonoid Pharmaceutical Science Pharmacology Pharmacognosy Methylation Analytical Chemistry Vitex Inhibitory Concentration 50 Mice chemistry.chemical_compound In vivo Drug Discovery LNCaP Tumor Cells Cultured Animals Humans Phenols Cytotoxicity Nuclear Magnetic Resonance Biomolecular Flavonoids chemistry.chemical_classification Plants Medicinal Molecular Structure biology Leukemia P388 Chemistry Organic Chemistry Prostatic Neoplasms biology.organism_classification Antineoplastic Agents Phytogenic Plant Leaves Disease Models Animal Complementary and alternative medicine Indonesia Colonic Neoplasms Molecular Medicine Drug Screening Assays Antitumor |
| Zdroj: | Journal of Natural Products. 66:865-867 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/np0300784 |
| Popis: | Bioassay-guided fractionation of the chloroform-soluble extract of the leaves of Vitex negundo led to the isolation of the known flavone vitexicarpin (1), which exhibited broad cytotoxicity in a human cancer cell line panel. In an attempt to increase the cytotoxic potency of 1, a series of acylation reactions was performed on this compound to obtain its methylated (2), acetylated (3), and six new acylated (4-9) derivatives. Compound 9, the previously unreported 5,3'-dihexanoyloxy-3,6,7,4'-tetramethoxyflavone, showed comparative cytotoxic potency to compound 1 and was selected for further evaluation. However, this compound was found to be inactive when evaluated in the in vivo hollow fiber assay with Lu1, KB, and LNCaP cells at the highest dose (40 mg/kg/body weight) tested, and in the in vivo P-388 leukemia model (135 mg/kg), using the ip administration route. |
| Databáze: | OpenAIRE |
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