Separation of Alkaloids by Paper Chromatography

Carless, J. E.; Woodhead, H. B.

doi:10.1038/168203a0

Cited by 27 publications

(4 citation statements)

References 5 publications

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“…The resulting highly overdetermined system of linear simultaneous equations was solved by a least squares method employing a multiple regression computer program which will be described elsewhere (3). Typical analyses accounted for 97 to 103% of the polymer present.…”

Section: Debska (4) Usedmentioning

confidence: 99%

Paper Partition Chromatographic Determination of Per Cent Solute Extracted into Organic Phase.

Kabasakalian¹

1964

Anal. Chem.

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Section: Debska (4) Usedmentioning

confidence: 99%

Paper Partition Chromatographic Determination of Per Cent Solute Extracted into Organic Phase.

Kabasakalian¹

1964

Anal. Chem.

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“…The 2,4-dinitrophenyl derivatives of amino acids were also separable (32,181). 309), alkaloids (56), antibiotics (321,858), ascorbic acid (282,372), glucosides (811), nicotinic acid (186), histamine (230), peptides (215), polyphenols (295), porphyrins (259), purines (285), pteridines (3), steroids (51,141,192,193), thyroxine (352), tryptophan metabolites (235), uric acid (347), nucleic acids (28, 232, 824, 365), and other phosphorylated bases (25,361). Organic substances examined were amines (39), azo dyes (76), alcohols (165), pyridine derivatives (153), phenols (152, 292), pH indicators (210), 2,4-dinitrophenvlhydrazones (290), sulfonamides (299), and water in alcohol (841).…”

Section: Ion Exchangementioning

confidence: 99%

Chromatography and Analogous Differential Migration Methods

Strain¹,

Murphy²

1952

Anal. Chem.

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“…This has been confirmed ancl no tl-ace of S-methyltyramine or tyramine was detected either. I t seems highly likellthat the source of tyramine in the roots is tyrosine since it is \\re11 establishecl that this amino acid is converted by avariety of bacteria (4,7,8,15,18,21) and in the kidney tissue of animals (10, 11, 22, 27) to tyramine. However \Verle and Boclen (26) were unable to detect an amino acid decarboxylase in yeast extracts.…”

mentioning

confidence: 99%

“…The best separation on untreated filter paper was achieved with n-butanol containing ammonia a s the developing solvent. The pH of the solvelit was found to influence the R F values of the amines, and since filter paper buffered t o a fixed p1-I had been useful in the separation of the solanaceo~~s and ergot alkaloids (4), this technicl~~e was in\-estigated. On carrying out a series of chromatograms 011 paper buffered a t cliffel-ent pH values, varying degrees of separation were obtained.…”

mentioning

confidence: 99%

The Biogenesis of Alkaloids: Vi. The Formation of Hordenine and N-Methyltyramine From Tyramine in Barley

Leete¹,

Kirkwood²,

Marion³

1952

Can. J. Chem.

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'I'yramine-a-C", synthesized from C'(-barium carbonate, was ad~uirlistered to sprouting barley and radioactive hordenine and N-methyltyramine isolated from the roots. Separation of these alkaloids by chromatography followed by degradation showed that all the activity was located in the a-carbon atom:The specihc activity of the N-methyltyramine was about 10 times t h a t of hordenine. From the results it is concluded t h a t t y r a~n i~i e undergoes methylation in the barley root to N-methyltyramine and thence to hordenine. I t has been shown (13) that formate is utilized in barley roots for the production of the N-methyl groups of the alkaloid hordenine (N-dimethyltyramiile). Preliininary experimerits (13) have also indicated that although formate is also responsible for the formation of the methyl groups of choline, the latter is not involved in the methylation of hordenine. Quite recently Brown and Byerrum (3) have studied the synthesis of nicotine in Nicotiana rustica Id., and their results seein to indicate that the role of formate consists in the production of the labile met11g.l group of methionine which subsequently undergoes transrnethylation with nornicotine.The isolation of N-methyltyramine from certain species of barley (12) provided evidence in favor of the assunlption that the final step in the synthesis of hordenine by the plant was the N-methylation of tyramine. This assumption could be confirmed by feeding tyramine labelled with C1"o the plant and, after a suitable time, isolating the hordenine and determining whether it was labelled on the same carbon atom as in the administered tyramine.Since tyramine and hordenine are chemically so similar it was essential to devise a inethod that would separate them completely in order to be sure that an>-activity found in the isolated hordenine was not due to a trace of the administered active tyramine. Paper chro~ilatography was found to be an excellent method of distinguishing between these anlines. Munier and Macheboeuf (19) have described the paper chromatography of various alkaloids, including hordenine. However chro~natograms run with the solvents described by these aiit1101-s failed to afford discrete separation of tyramine, hordenine, and Nmethyltyramine. The last base was included in this test since it was found to occur with the hordenine in the roots of Charlottetown No. 80 barley which nras the species under investigation. The best separation on untreated filter paper was achieved with n-butanol containing ammonia a s the developing solvent. The pH of the solvelit was found to influence the R F values of the amines, and since filter paper buffered t o a fixed p1-I had been useful in the

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Separation of Alkaloids by Paper Chromatography

Cited by 27 publications

References 5 publications

Paper Partition Chromatographic Determination of Per Cent Solute Extracted into Organic Phase.

Paper Partition Chromatographic Determination of Per Cent Solute Extracted into Organic Phase.

Chromatography and Analogous Differential Migration Methods

The Biogenesis of Alkaloids: Vi. The Formation of Hordenine and N-Methyltyramine From Tyramine in Barley

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