02269naa a2200277 a 450000100080000000500110000800800410001902400360006010000140009624501550011026000090026550003360027452010450061065300160165565300140167165300210168565300210170665300250172770000160175270000170176870000200178570000260180570000180183170000140184977301280186310169362020-06-02       2016    bl uuuu     u00u1 u    #d7 a10.1177/1934578X16011011042DOI1 aREINA, L.  aAggregation Behavior of 6-Isocassine and N-Methyl-6-IsocassinebInsights into the Biological Mode of Action of Lipid Alkaloids.h[electronic resource]  c2016  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.  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.  aAGGREGATION  aDIFFUSION  aHYDROGEN BONDING  aNOE ENHANCEMENTS  aPIPERIDINE ALKALOIDS1 aBOTTINI, G.1 aBENNADJI, Z.1 aVINCIGUERRA, V.1 aFERREIRA CHIESA, F.A.1 aMENÉNDEZ, P.1 aMOYNA, G.  tNatural Product Communications, 2016, Volume 11, Issue 11, Pages 1641-1644. DOI. https://doi.org/10.1177/1934578X1601101104