Isoquinoline alkaloids salsolinol

Microchip electrophoresis with label-free detection using deep UV fluorescence detection with excitation at 266 nm was applied by Ohla et al. (2011) for the determination of biologically active compounds (dopamine, serotonin, tryptophan, tyrosine, and the isoquinoline alkaloid salsolinol) in bananas, in less than 1 min. For comparison purposes, microchip electrophoresis was also coupled with MS detection using microfluidic... 

Mammalian isoquinoline alkaloids include simple tetrahydroisoquinolines, catecholic congeners such as salsolinol and its methyl ether analogs,... 

Fig. 6.2. Separation of some dopamine derived isoquinoline alkaloids Column Vydac TP 401 SCX 10 pm (250x3.2 nrn ID), mobile phase 0.2 M NH.H.P0., flow rate 0.5 ml/min, column temperature 51°C, detection UV 280 nm. Peaks 1, dopamine-, 2, salsolinol 3, tetrahydropapaveroline 4, 2,3,10,11-tetrahydroxyberbine 5, 3 -0-methyltetrahydropapaveroline 6, 2,3,9,10-tetrahydroxyberbine 7, 7-0-methyltetrahydropapaveroline 8, 4 -0-methyl-tetrahydropapaveroline 9, 6-0-methyltetrahydropapaveroline 10, 2-0-methyltetrahydroxyberbine 11, 11-0-methyltetrahydroxyberbine 12, 10-0-methyltetrahydroxyberbine 13, 3-0-methyl-tetrahydroxyberbine. (Fig. 6.1 and 6.2 were reproduced with permission from ref. 26, by courtesy of Marcel Dekker, Inc.).

Nicotine boldine and other aporphine alkaloids C-toxiferine coniine and other piperidine alkaloids cytisine and other quinohzidine alkaloids epibatidine tubocurarine Berbamine, berberine, and other isoquinoline alkaloids cinchonidine and other quinoline alkaloids corynanthine, yohimbine, and other indole alkaloids emetine ephedrine ergometiine and related ergot alkaloids Ergocornine and related ergot alkaloids bulbocapnine and related aporphine alkaloids anisocycline, stylopine, and related protoberberine alkaloids salsolinol and related isoquinohnes BicuculUne, cryptopine, hydrastine, and related isoquinoline alkaloids securinine harmaline and related beta-carboline alkaloids Corymine, strychnine, and related indole alkaloids Histrionicotoxin and related piperidines ibogaine and related indole alkaloids nuciferine and related aporphine alkaloids... 

The) simple isoquinoline salsolinol (152), a relative of the alkaloid salsoline (153), is mono-O-methylated by an enzyme preparation from rat liver,... 

Ephedrrne and related phenylalkyl amines (AA) reserprne, ihogaine, and related indole alkaloids (AA) cocaine (AA) armonaine and related aporphine alkaloids (AA) arecaidine (AA) norharman and related (J-carholine alkaloids (AA) salsolinol and related isoquinolines (AA)... 

Several syntheses of racemic salsolinol (64) by Pictet-Spenglercycliza-tion of dopamine with acetaldehyde have been reported 10a,150). The synthesis of the optically active (5) enantiomer TIQ 64a from the methyl ether analogs TIQs 62a and 68a by acid hydrolysis correlates the chemistry of mammalian alkaloids with that of plant isoquinolines (146-148). 

MAO inhibitors can be classified as simple indole alkaloids (e.g., 13-carbolines, N,N-dimethyltryptamine N-methyltryptamine), simple isoquinolines (carnegine, salsolidine, salsolinol), quinoline alkaloids (e.g., quinine) and even complex indole alkaloids (e.g., vinblastine and vincristine). A structural similarity can be seen between the MAO blocker and endogenous substrates between the indole alkaloids and serotonin between the simple isoquinoline and dopamine, noradrenaline and adrenaline, which implies that these compounds bind to the active site of the enzyme. 

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