Semisynthesis and Biological Evaluation of Abietane-Type Diterpenes. Revision of the Structure of Rosmaquinone
| Autor: | Liliana Araujo, Nayely P. Montaño, Javier G. Luis, Laila Moujir, Lucía S. Andrés, Joaquín G. Marrero |
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| Rok vydání: | 2009 |
| Předmět: |
Stereochemistry
Pharmaceutical Science Microbial Sensitivity Tests Biology Gram-Positive Bacteria Chemical synthesis Carnosol Analytical Chemistry Structure-Activity Relationship chemistry.chemical_compound Chlorocebus aethiops Gram-Negative Bacteria Drug Discovery Animals Humans Organic chemistry Salvia Nuclear Magnetic Resonance Biomolecular Vero Cells Abietane Pharmacology chemistry.chemical_classification Plants Medicinal Molecular Structure Organic Chemistry Quinones Antineoplastic Agents Phytogenic Semisynthesis Terpenoid Quinone Complementary and alternative medicine chemistry Abietanes Molecular Medicine Diterpenes Drug Screening Assays Antitumor Diterpene Lactone HeLa Cells |
| Zdroj: | Journal of Natural Products. 72:1385-1389 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/np900047p |
| Popis: | The new aromatic diterpenes 7beta-O-benzylrosmanol (3), 7beta-O-benzyl-11,12-di-O-methylrosmanol (4), and 7alpha-thiophenylcarnosic acid (5) have been obtained by partial synthesis from carnosol (1), an abundant natural diterpene present in Salvia species. The structures of these compounds were established from their physical and spectroscopic data. The known diterpenes sagequinone methide A (6), 7beta-O-methylrosmanol (7), 7-O-methylrosmanol (8), and rosmaquinone B (9) were obtained from rosmanol (2). The spectroscopic data of these semisynthetic diterpenes were identical to data reported in the literature. In addition, the new semisynthetic isorosmaquinone (10) was obtained from isorosmanol (12). The proton resonances of rosmaquinone (11) are reassigned based on 2D NMR spectroscopy. These compounds, as well as eight known analogues, were evaluated for cytotoxic and antimicrobial activities. |
| Databáze: | OpenAIRE |
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