Calothrixamides A and B from the Cultured Cyanobacterium Calothrix sp. UIC 10520
| Autor: | Diana Kao, Nicholas H. Oberlies, James R. Fuchs, Joanna E. Burdette, Daniel S. May, Tyler A. Wilson, Aleksej Krunic, Jimmy Orjala, Camila M. Crnkovic |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
Cyanobacteria
Magnetic Resonance Spectroscopy Pharmaceutical Science Mass spectrometry 01 natural sciences Article Analytical Chemistry chemistry.chemical_compound Cell Line Tumor Drug Discovery Humans Derivatization Chemical decomposition Pharmacology chemistry.chemical_classification Chromatography Natural product biology 010405 organic chemistry Chemistry Fatty Acids Organic Chemistry Fatty acid Nuclear magnetic resonance spectroscopy biology.organism_classification Amides 0104 chemical sciences 010404 medicinal & biomolecular chemistry Complementary and alternative medicine Molecular Medicine Water Microbiology Two-dimensional nuclear magnetic resonance spectroscopy |
| Zdroj: | Journal of Natural Products. 81:2083-2090 |
| ISSN: | 1520-6025 0163-3864 |
| Popis: | Cyanobacteria are a source of chemically diverse metabolites with potential medicinal and biotechnological applications. Rapid identification of compounds is central to expedite the natural product discovery process. Mass spectrometry has been shown to be an important tool for dereplication of complex natural product samples. In addition, chromatographic separation and complementary spectroscopic analysis (e.g., UV) can enhance the confidence of the dereplication process. Here, we applied a droplet-liquid microjunction-surface sampling probe (droplet probe) coupled with UPLC-PDA-HRMS-MS/ MS to identify two new natural products in situ from the freshwater strain Calothrix sp. UIC 10520. This allowed us to prioritize this strain for chemical investigation based on the presence of new metabolites very early in our discovery process, saving both time and resources. Subsequently, calothrixamides A (1) and B (2) were isolated from large-scale cultures, and the structures were elucidated by 1D and 2D NMR spectroscopy and mass spectrometry. The absolute configurations were determined by a combination of chemical degradation reactions, derivatization methods (Mosher’s, Marfey’s, and phenylglycine methyl ester), and J-based configurational analysis. Calothrixamides showed no cytotoxic activity against the MDA-MB-435, MDA-MB-231, and OVCAR3 cancer cell lines. They represent the first functionalized long-chain fatty acid amides reported from the Calothrix genus and from a freshwater cyanobacterium. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|