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 | Acceso al texto completo restringido a Biblioteca INIA Tacuarembó. Por información adicional contacte bibliotb@tb.inia.org.uy. |
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Registro completo
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Biblioteca (s) : |
INIA Tacuarembó. |
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Fecha : |
21/02/2014 |
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Actualizado : |
02/06/2020 |
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Tipo de producción científica : |
Artículos en Revistas Indexadas Internacionales |
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Autor : |
REINA, L.; BOTTINI, G.; BENNADJI, Z.; VINCIGUERRA, V.; FERREIRA CHIESA, F.A.; MENÉNDEZ, P.; MOYNA, G. |
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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. |
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Título : |
Aggregation Behavior of 6-Isocassine and N-Methyl-6-Isocassine: Insights into the Biological Mode of Action of Lipid Alkaloids. |
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Fecha de publicación : |
2016 |
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Fuente / Imprenta : |
Natural Product Communications, 2016, Volume 11, Issue 11, Pages 1641-1644. DOI. https://doi.org/10.1177/1934578X1601101104 |
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DOI : |
10.1177/1934578X1601101104 |
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Idioma : |
Inglés |
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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. |
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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. |
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Palabras claves : |
AGGREGATION; DIFFUSION; HYDROGEN BONDING; NOE ENHANCEMENTS; PIPERIDINE ALKALOIDS. |
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Asunto categoría : |
K10 Producción forestal |
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Marc : |
LEADER 02269naa a2200277 a 4500
001 1016936
005 2020-06-02
008 2016 bl uuuu u00u1 u #d
024 7 $a10.1177/1934578X1601101104$2DOI
100 1 $aREINA, L.
245 $aAggregation Behavior of 6-Isocassine and N-Methyl-6-Isocassine$bInsights into the Biological Mode of Action of Lipid Alkaloids.$h[electronic resource]
260 $c2016
500 $aArticle 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.
520 $aThe 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.
653 $aAGGREGATION
653 $aDIFFUSION
653 $aHYDROGEN BONDING
653 $aNOE ENHANCEMENTS
653 $aPIPERIDINE ALKALOIDS
700 1 $aBOTTINI, G.
700 1 $aBENNADJI, Z.
700 1 $aVINCIGUERRA, V.
700 1 $aFERREIRA CHIESA, F.A.
700 1 $aMENÉNDEZ, P.
700 1 $aMOYNA, G.
773 $tNatural Product Communications, 2016, Volume 11, Issue 11, Pages 1641-1644. DOI. https://doi.org/10.1177/1934578X1601101104
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