Structures and Absolute Configurations of Sulfate-Conjugated Triterpenoids Including an Antifungal Chemical Defense of the Green Macroalga Tydemania expeditionis
| Autor: | Mark E. Hay, Lauren Mylacraine, Amy L. Lane, Ren-Wang Jiang, William G.L. Aalbersberg, Julia Kubanek, Kenneth I. Hardcastle, Craig R. Fairchild |
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| Rok vydání: | 2008 |
| Předmět: |
Antifungal Agents
Stereochemistry medicine.medical_treatment Molecular Conformation Pharmaceutical Science Microbial Sensitivity Tests Sulfuric Acid Esters Biology Crystallography X-Ray Article Analytical Chemistry Steroid Terpene chemistry.chemical_compound Sulfation Ascomycota Triterpene Chlorophyta Drug Discovery medicine Fiji Humans Sulfate Nuclear Magnetic Resonance Biomolecular Pharmacology chemistry.chemical_classification Natural product Molecular Structure Organic Chemistry Absolute configuration Triterpenes Terpenoid Complementary and alternative medicine chemistry Molecular Medicine Drug Screening Assays Antitumor |
| Zdroj: | Journal of Natural Products. 71:1616-1619 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/np800307h |
| Popis: | Cytotoxicity-guided fractionation of the green macroalga Tydemania expeditionis led to isolation of four sulfate-conjugated triterpenoids including one new lanostane-type triterpenoid disulfate, lanosta-8-en-3,29-diol-23-oxo-3,29-disodium sulfate (1), and three known cycloartane-type triterpenoid disulfates, cycloartan-3,29-diol-23-one 3,29-disodium sulfate (2), cycloart-24-en-3,29-diol-23-one 3,29-disodium sulfate (3), and cycloartan-3,23,29-triol 3,29-disodium sulfate (4). Extensive 1D and 2D NMR analyses in combination with X-ray crystallography established the structure and absolute configuration of 1 and allowed determination of the absolute configurations of 2–4 with a revision of previously assigned configuration at C-5. Each natural product was moderately cytotoxic in tumor cell and invertebrate toxicity assays. Of the natural products, only 4 exhibited significant antifungal activity at whole-tissue natural concentrations against the marine pathogen Lindra thalassiae. Comparison of the biological activities of natural products with their desulfated derivatives indicated that sulfation does not appear to confer cytotoxicity or antifungal activity. |
| Databáze: | OpenAIRE |
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