Aggregation Behavior of 6-Isocassine andN-Methyl-6-Isocassine: Insights into the Biological Mode of Action of Lipid Alkaloids
| Autor: | Zohra Bennadji, Pilar Menéndez, Vittorio Vinciguerra, Fernando Ferreira, Guillermo Moyna, Gualberto Bottini, Luis Reina |
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| Rok vydání: | 2016 |
| Předmět: |
Pharmacology
Chloroform 010405 organic chemistry Hydrogen bond Diffusion Alkaloid Plant Science General Medicine 01 natural sciences 0104 chemical sciences Solvent 010404 medicinal & biomolecular chemistry chemistry.chemical_compound Complementary and alternative medicine chemistry Computational chemistry Drug Discovery Molecule Methanol Mode of action |
| Zdroj: | Natural Product Communications. 11:1934578X1601101 |
| ISSN: | 1555-9475 1934-578X |
| DOI: | 10.1177/1934578x1601101104 |
| Popis: | The aggregation behavior of 6-isocassine and N-methyl-6-isocassine, two piperidin-3-ol alkaloids isolated respectively from the barks of Prosopis nigra and P. affinis, was investigated using a combination of NOE experiments and diffusion measurements in solvents of varying polarity and hydrogen bonding capacity. While the NOE enhancements for N-methyl-6-isocassine are positive, regardless of the solvent, those for 6-isocassine shift from negative to positive when going from chloroform- d to methanol- d4solution. In addition, despite the self-diffusion coefficients of both compounds being virtually identical in methanol- d4, N-methyl-6-isocassine diffuses nearly twice as fast as the non-methylated alkaloid in chloroform- d. The changes in rotational and translational dynamics observed between solvents for 6-isocassine suggest that the molecule forms dimeric head-to-head aggregates in non-polar aprotic environments, a behavior that could help explain the biological mode of action that has been proposed for this type of alkaloids. |
| Databáze: | OpenAIRE |
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