Relative Configurational Assignment of 4-Hydroxyprorocentrolide and Prorocentrolide C Isolated from a Benthic Dinoflagellate ( Prorocentrum lima)
| Autor: | Yeong Du Yoo, Eun Ju Jeong, A Reum Yang, Jung-Rae Rho, Sangbum Lee |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
Magnetic Resonance Spectroscopy
Double bond Stereochemistry Pharmaceutical Science Ether Ring (chemistry) 01 natural sciences Analytical Chemistry Stereocenter chemistry.chemical_compound Structure-Activity Relationship Drug Discovery Prorocentrum lima Pharmacology chemistry.chemical_classification biology 010405 organic chemistry Chemistry Organic Chemistry Dinoflagellate Nuclear magnetic resonance spectroscopy biology.organism_classification 0104 chemical sciences 010404 medicinal & biomolecular chemistry Complementary and alternative medicine Benthic zone Dinoflagellida Molecular Medicine Marine Toxins |
| Zdroj: | Journal of natural products. 82(4) |
| ISSN: | 1520-6025 |
| Popis: | Herein, we clarify the structure and relative configurations of two prorocentrolide analogues (1 and 2) isolated from the benthic marine dinoflagellate Prorocentrum lima. The results of NMR spectroscopy show that 1 is prorocentrolide substituted by a hydroxy group at C-4, while the newly isolated compound 2 can be thought of as 1 lacking one ether ring and having one extra double bond. The relative configurations of all stereogenic centers and the configurations of the double bonds in 1 and 2 were determined utilizing ROESY correlations and J-based configuration analysis. Furthermore, 2 was shown to exhibit cytotoxicity against HCT-116 and Neuro-2a cells (IC50 2.2 and 5.2 μM, respectively. |
| Databáze: | OpenAIRE |
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