The Separation of Alkaloids by Partition Paper Chromatography

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

doi:10.1111/j.2042-7158.1951.tb13124.x

Cited by 27 publications

(2 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The alkaloids contained in both phases of these 11 tubes were then isolated in the usual manner. Paper chromatography (19) of the material by the descending technique with Whatman No. 1 paper buffered to pH 2.5, with n-butanol saturated with water as solvent, showed the presence of alltaloids after spraying with Dragendorff's reagent.…”

Section: Isolation Of Lycodinementioning

confidence: 99%

Lycodine, a New Alkaloid of Lycopodium Annotinum

Anet¹,

Eves²

1958

Can. J. Chem.

View full text Add to dashboard Cite

LYCODINE, A NEW ALKALOID O F LYCOPODIUM ANNOTINUM1r \ new allcaloid, lycocline, CliHYINd, m.p. llSO, has been isolated fro111 Lycopodizr?rt a n -?~o t i n z~n l .Lycodine is a tetracyclic diaciclic base containi~lg a secontlary nitrogen atom, a 2,3-disubstit~ited pyridine ring, and a C-methyl group. T h e 2,3-dis~ibstit~1tion is in the form of a saturatecl sis-niemberecl ring.The all;aloids of Lycopodiu7n nnnokinz~m L. have been sti~died by several groups of worlters in Canada and in Europe (1, 2, 3, 4, 5 ) . The structure of annotinine, C1SH2103N, which is the main alkaloid of this species, is now known (6, 7) and is of a quite novel type. I t therefore becomes of interest to study the chemical structure of the minor alkaloids of this plant.During the process of developing suitable methods for the separation of the many minor alkaloids which have been reported to occur in this Lycopodium species, we noticed that certain fractions possessed ultraviolet absorption characteristic of a pyridine chromophore, inore or less submerged behind general absorption. This paper describes the isolation, characterization, and partial cletermination of the structure of a new alkaloid, lycodine, which was responsible for this characteristic Absorption.Lycodine was concentrated by countercurrent distribution of the allcaloid mother liquors from the crystallization of annotinine. Two successive countercurrent distributions were carried out, first in six large separatory funnels \vith the system chloroform-buffer of pH 6 and then in a 60-tube Craig machine with the system chloroforn~-buffer of pH 5.2.From these countercurrent distributions an all;aloid fraction was obtained which hacl the correct ultraviolet absorption. By chron~atography of this fraction on activatecl alumina pure crystalline lycodine was obtained.Lycodine, m.p. l l S O , [a],, -lo0, had the fornlula C17H2.LN? and gave a characteristic dipicrate, m.p. 229'-233' (decomp.), which was sparingly soluble in methanol. Titration of the base in 50% methanol showed that the pK,'s of the base were 3.97 and 8.08. One C-methyl group was found to be present by the Kuhn-Roth method. The ultraviolet spectra of the base in neutral and in acid solutions are shown in Fig. I , and correspond to an unconjugated pyridine chromophore in the base and salt forms respectively. A fuller discussion of these spectra will be left till after consideration of other results (see below).The infrared spectrum of the base (in Nujol) is shown in Fig. 2 ; the sharp band a t 3270 cm.-I must be due to a N-H group (8). As often happens (8) this band is of very low intensity in the spectrum (Fig. 2) of the carbon tetrachloride solution of the compound. The presence of a pyridine ring is confirmed by the band (9) a t 1580 cm.-I (in Nujol) and that of a C-methyl group by a band (10) a t 1382 cm.-I (in CC14). Acetylation of lycodine with acetic anhydride gave a N-acetyl clerivative, isolated as the monopicrate. Titration of the picrate showed that the acetylated base hacl only one basic center (pK, 4.95). H...

show abstract

Section: Isolation Of Lycodinementioning

confidence: 99%

Lycodine, a New Alkaloid of Lycopodium Annotinum

Anet¹,

Eves²

1958

Can. J. Chem.

View full text Add to dashboard Cite

show abstract

“…Brindle, et al (2), using buffered filter paper for the separation of the alkaloids and Munier's method for the developmentof thechromatogram, were able to detect five micrograms of atropine. 122 equivalent to Whatman No.…”

mentioning

confidence: 99%