Pteleatinium salt

A full report has appeared of the isolation and characterization of the antimicrobial quaternary derivative pteleatinium salt (32). Dehydration of the chloride with concentrated sulphuric acid and recovery of the product from a basic solution gave a yellow compound, CigHigNOa, formulated as the 8-hydroxy-derivative (34), but by analogy with the compound obtained from ribalinium salt (33) the dehydration product of pteleatinium salt is more likely to be the zwitterion... 

C16H17NO3 the u.v. spectrum and analytical data are consistent with this structure. The presence of a tetrasubstituted double bond in compound (35) is of some interest, since dehydration of hydroxyisopropyldihydrofuroquinolines usually furnishes isoprqpylfuroquinolines. Pteleatinium salt is the principal alkaloid of the... 

Pteleatinium salt Methylplatydesminium salt. Methylhydroxyluninium salt Ptelea Cholsya Cholsya ... 

As a result of the reported antimicrobial action of extracts of the hop tree, Ptelea trifoliata, Mitscher et al. (54) investigated the aboveground constituents and found that the sole active agent was a new phenolic quinolinium derivative pteleatinium salt. The alkaloid was isolated as the chloride, C16H20NO4CI, and was shown to be the 8-hydroxy-Af-methyl-platydesminium salt (38) on the basis of IR, UV, NMR, and mass spectrometry and of correlation with known quinoline alkaloids. Thus, pyridine effected demethylation to the 4-quinolone 39 which, with diazomethane, was converted into (+)-balfourodine (12), while methylation of pteleatinium chloride with methyl iodide and sodium carbonate gave O-methyl-... 

Another apparent anomaly arises from the assignment of an (5) configuration (54) to (—)-0-methylhydroxyluninium salt (120) by comparison of the circular dichroism spectrum with (+)-(/ )-pteleatinium salt (102) these alkaloids cooccur in Ptelea trifoliata, and the stereochemical result implies that they are derived biosynthetically from epoxides of opposite configuration. 

N-methyIplatydesminium salt, R=H, 67 pteleatinium salt,R=OH,68 O-methylbalfourodinium salt, R=OMe,69... 

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