Cytotoxic Constituents of Aspergillus terreus from the Rhizosphere of Opuntia versicolor of the Sonoran Desert
| Autor: | Zhongge Zhang, Louise M. Canfield, Thomas J. Turbyville, Luke Whitesell, A. A. Leslie Gunatilaka, Hans D. VanEtten, Leland S. Pierson, D. M. Bigelow, E. M. Kithsiri Wijeratne |
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| Rok vydání: | 2003 |
| Předmět: |
Indoles
Carboxylic acid Nervous System Neoplasms Pharmaceutical Science Antineoplastic Agents Cyclopentanes Pharmacognosy Analytical Chemistry Cell Line Tumor Drug Discovery Botany Humans Cytotoxic T cell Aspergillus terreus Nuclear Magnetic Resonance Biomolecular Pharmacology chemistry.chemical_classification Rhizosphere Molecular Structure biology Cell Cycle Organic Chemistry Arizona Opuntia Stereoisomerism Biological activity Fungi imperfecti biology.organism_classification Asterredione Aspergillus Complementary and alternative medicine chemistry Molecular Medicine Desert Climate Drug Screening Assays Antitumor |
| Zdroj: | Journal of Natural Products. 66:1567-1573 |
| ISSN: | 1520-6025 0163-3864 |
| Popis: | A novel cyclopentenedione, asterredione (1), two new terrecyclic acid A derivatives, (+)-5(6)-dihydro-6-methoxyterrecyclic acid A (2) and (+)-5(6)-dihydro-6-hydroxyterrecyclic acid A (3), and five known compounds, (+)-terrecyclic acid A (4), (-)-quadrone (5), betulinan A (6), asterriquinone D (7), and asterriquinone C-1 (8), were isolated from Aspergillus terreus occurring in the rhizosphere of Opuntia versicolor, using bioassay-guided fractionation. Acid-catalyzed reaction of 2 under mild conditions afforded 4, whereas under harsh conditions 2 yielded 5 and (-)-isoquadrone (9). Catalytic hydrogenation and methylation of 4 afforded 5(6)-dihydro-terrecyclic acid A (10) and (+)-terrecyclic acid A methyl ester (11), respectively. The structures of 1-11 were elucidated by spectroscopic methods. All compounds were evaluated for cytotoxicity in a panel of three sentinel cancer cell lines, NCI-H460 (non-small cell lung cancer), MCF-7 (breast cancer), and SF-268 (CNS glioma), and were found to be moderately active. Cell cycle analysis of 2, 4, and 5 using the NCI-H460 cell line indicated that 4 is capable of disrupting the cell cycle through an apparent arrest to progression at the G(1) and G(2)/M phases in this p53 competent cell line. A pathway for the biosynthetic origin of asterredione (1) from asterriquinone D (7) is proposed. |
| Databáze: | OpenAIRE |
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