Pyrrolidine, Piperidine, and Pyridine Alkaloids

Robinson, Trevor

doi:10.1007/978-3-642-61830-7_4

Molecular Biology Biochemistry and Biophysics

1981

DOI: 10.1007/978-3-642-61830-7_4

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Pyrrolidine, Piperidine, and Pyridine Alkaloids

Trevor Robinson¹

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Cited by 2 publications

(2 citation statements)

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“…The piperidine alkaloids are a vast class of compounds derived biosynthetically from lysine [1], which include piperine, lobeline, and carpaine [2]. The last is one of the most relevant members of the "lipid alkaloids," a family that also comprises prosopine, juliprosopine, cassine, and carnavaline [3][4][5][6][7].…”

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confidence: 99%

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Aggregation Behavior of 6-Isocassine andN-Methyl-6-Isocassine: Insights into the Biological Mode of Action of Lipid Alkaloids

Reina¹,

Bottini²,

Bennadji

et al. 2016

Natural Product Communications

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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-d 4 solution. In addition, despite the self-diffusion coefficients of both compounds being virtually identical in methanol-d 4 , 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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confidence: 99%

“…1 H (500 MHz) and13 C (100 MHz) NMR data for N-methyl-6-isocassine (2) in CDCl 3 and CD 3 OD ( in ppm, J in Hz).…”

mentioning

confidence: 99%

Aggregation Behavior of 6-Isocassine andN-Methyl-6-Isocassine: Insights into the Biological Mode of Action of Lipid Alkaloids

Reina¹,

Bottini²,

Bennadji

et al. 2016

Natural Product Communications

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Hydrogen-bonding aggregation of N-methylpyrrolidine betaine with p-hydroxybenzoic acid

Dega‐Szafran

Roszak

Safari

et al. 2020

Journal of Molecular Structure

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Pyrrolidine, Piperidine, and Pyridine Alkaloids

Cited by 2 publications

References 177 publications

Aggregation Behavior of 6-Isocassine andN-Methyl-6-Isocassine: Insights into the Biological Mode of Action of Lipid Alkaloids

Aggregation Behavior of 6-Isocassine andN-Methyl-6-Isocassine: Insights into the Biological Mode of Action of Lipid Alkaloids

Hydrogen-bonding aggregation of N-methylpyrrolidine betaine with p-hydroxybenzoic acid

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