The constituents of the bark of Prunus serotina : [isolation of 1-mandelonitrile glucoside] / by Frederick B. Power and Charles W. Moore.

  • Frederick Belding Power
Date:
[1909]
Catalogue details

Licence: Attribution 4.0 International (CC BY 4.0)

Credit: The constituents of the bark of Prunus serotina : [isolation of 1-mandelonitrile glucoside] / by Frederick B. Power and Charles W. Moore. Source: Wellcome Collection.

Provider: This material has been provided by The Royal College of Surgeons of England. The original may be consulted at The Royal College of Surgeons of England.

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    bark by an enzyme, which may be obtained by adding to a cold aqueous infusion of the bark'a large volume of strong alcohol. The precipitate thus produced is a light-coloured, amorphous powder, readily soluble in cold water. It contains a large proportion of inorganic material, but readily hydrolyses /3-glucosides. Summary. The results of this investigation may be summarised as follows : The material employed, consisting of the air-dried bark of Prunus serotina, Ehrhart, yielded on maceration with water an amount of hydrogen cyanide corresponding to about 0'075 per cent, of its weight. It contains a relatively small amount of a cyanogenetic glucoside, which has been shown to be £-mandelonitrile glucoside, C14Hl706N (m. p. 145—147°; [a]D — 29,6°), and the latter has also been obtained in the form of its tetra-acetyl derivative (m. p. 136—137°; [a]D - 24'0°). An enzyme which hydrolyses /3-gluoosides is also present in the bark. An alcoholic extract of the bark, when distilled with steam, yielded small amounts of benzoic acid and an essential oil, but no hydrogen cyanide. The essential oil distilled between 100° and 120°/15 mm., and possessed an odour quite distinct from that of benzaldehyde. The non-volatile constituents of the bark, as obtained after treating the alcoholic extract with steam, consisted of a green resin, insoluble in either hot or cold water; a brown resin, readily soluble in the hot aqueous liquid, but which was slowly deposited on standing; and material which remained dissolved in the cold aqueous liquid. The green resin, amounting to about 1 percent, of the weight of the bark, yielded a phytosterol, C27H460 (m. p. 135—136°; [a]D — 34,0°) ; palmitic, stearic, oleic, and linolic acids, with apparently a very little isolinolenic acid ; a small amount of ipuranol, C23H3802(0H)2, melting at 285—290°; and, after acid hydrolysis, oleic acid, dextrose, and /3-methylcesculetin, C10H8O4 (m. p. 204°). The brown resin, likewise amounting to about 1 per cent, of the weight of the bark, yielded, after acid hydrolysis, a trace of a phytosterol, small amounts of oleic acid, /3-methylaesculetin, and dextrose, together with insoluble, red, resinous material, which, on fusion with potassium hydroxide, gave formic, acetic, butyric, and protocatechuic acids. The portion of the alcoholic extract of the bark which was soluble in cold water, and from which the above-described resins had been removed, contained ^-mandelonitrile glucoside, together with a quantity of sugar and tannin. It yielded, furthermore, benzoic, trimethylgallic, and p-coumaric acids, traces of a substance melting at 240—241°, and, after heating with dilute sulphuric acid, ^-mandelic acid and /3-methylsesculetin were obtained. The two latter compounds were evidently formed