Fecha/hora: 07/06/2024 22:50:03

Biblioteca(s): | INIA Tacuarembó.
Fecha corriente: | 21/02/2014
Fecha de la última actualización: | 02/06/2020
Autoria: | REINA, L.; BOTTINI, G.; BENNADJI, Z.; VINCIGUERRA, V.; FERREIRA CHIESA, F.A.; MENÉNDEZ, P.; MOYNA, G.
Afiliación: | LUIS REINA, Universidad de la República (UdelaR)/ Facultad de Química.; GUALBERTO BOTTINI, cDepartamento de Química del Litoral, CENUR Litoral Norte, UdelaR, Paysandú, Uruguay.; ZOHRA BENNADJI SOUALHIA, INIA (Instituto Nacional de Investigación Agropecuaria), Uruguay; VITTORIO VINCIGUERRA, Dipartimento per la Innovazione nei Sistemi Biologici, Agroalimentari e Forestali, Università della Tuscia, Largo dell’Università, Italy; FERNANDO AMAURY FERREIRA CHIESA, Universidad de la República (UdelaR)/ Facultad de Química.; PILAR MENÉNDEZ, Universidad de la República (UdelaR)/ Facultad de Química.; GUILLERMO MOYNA, c Departamento de Química del Litoral, CENUR Litoral Norte, UdelaR, Paysandú, Uruguay.
Título: | Aggregation Behavior of 6-Isocassine and N-Methyl-6-Isocassine: Insights into the Biological Mode of Action of Lipid Alkaloids.
Año de publicación: | 2016
Fuente/Imprenta: | Natural Product Communications, 2016, Volume 11, Issue 11, Pages 1641-1644. DOI. https://doi.org/10.1177/1934578X1601101104
DOI: | 10.1177/1934578X1601101104
Idioma: | Inglés
Notas: | Article history: Received: February 1st, 2016// Accepted: May 25th, 2016. Dedicated to the memory of our esteemed colleague and friend Eduardo Alonso Paz. Acknowledgments - Funding from the INIA (award L4-FO-21-0-00), the ANII (award POS_NAC_2014_1_102226), the DGRC-UdelaR (Programa 720), and the PEDECIBA is greatly acknowledged.

Contenido:

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-d4 solution. 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.

Palabras-Clave: | AGGREGATION; DIFFUSION; HYDROGEN BONDING; NOE ENHANCEMENTS; PIPERIDINE ALKALOIDS.
Categoría del tema: | K10 Producción forestal
Registro original: | INIA Tacuarembó (TBO)
Ejemplares: | TBO - (16936-1) - PXI - AP - DD -  -  -  - DIS