On Waldivin and Cedrin.
BY CH. TANRET.
Translated from "Bull. general de Thérapeutique" (Tome xcix, 1880, pp. 504 to 506), by FRED. B. POWER.
The Simaba waldivia (Simarubaceae) grows in Columbia, where it is sometimes, but wrongly, confounded with a tree of the same family, the Simaba cedron. Its fruit, which possesses an extreme bitterness, shares with that of the latter the reputation of the remarkable properties which have been attributed to the cedron in the republics of the equator, and of which several travelers have already spoken to the academy. At the request of Mr. Dujardin-Beaumetz, who was desirous of studying the physiological and therapeutical action of it, the author has isolated the two active principles of the two fruits, which were obligingly furnished him by Mr. Bestrepo. Only that of the waldivia was obtained crystalline, and this is now called waldivin.
Preparation.—The finely-powdered waldivia is extracted with alcohol of 70 per cent., and then distilled. The residue while still warm is agitated with a large quantity of chloroform, which takes up the waldivin, and the carefully separated chloroformic liquid is then distilled to dryness, the latter residue, when taken up again with boiling water, separates, on cooling, the waldivin in crystals. The yield is very variable, according to the fruits; thus from 1 part to 1000, of badly preserved fruits, it may amount to as much as 8 from recent and dry waldivias.
Composition.—The crystals of waldivin contain water of crystallization, and their composition may be represented by the formula C36H24O20.5H2O. When heated to 110°C. they lose 10 per cent., and the formula requires 9.8 per cent.; on the other hand, the analysis of the anhydrous body has given the following results:
|Found.||Calculated for C36H24O20|
Physical Properties.—The waldivin crystallizes in hexagonal prisms, terminated by a double hexagonal pyramid; it has the specific gravity 1.46, and when heated loses its water of crystallization, then melted at about 230 °C. it becomes colored, but is not volatile, and possesses no rotatory power. It is very sparingly soluble in cold water (600 parts at 15°C.), but dissolves in 30 parts of boiling water, acids and salts increasing its solubility considerably, and its aqueous solutions froth strongly upon agitation; it dissolves in 60 parts of 70 per cent. alcohol at 15°C., but requires 190 parts of absolute alcohol. Chloroform dissolves it abundantly, but it is insoluble in ether. It possesses an extreme bitterness.
Chemical Properties.—The waldivin is neutral, its aqueous solutions are precipitated by tannin, and by ammoniacal acetate of lead; the neutral and basic acetates of lead do not precipitate it. In the cold, sulphuric and nitric acids dissolve it without appearing to produce any sensible alteration, the solutions not being precipitated on the addition of water; but if the solutions be neutralized by means of an alkaline bicarbonate, and if the salt formed is not in sufficiently large quantity to hold it in solution, the waldivin is partially deposited.
The most remarkable property of the waldivin is the facility with which it is decomposed by alkalies; with caustic alkalies the loss of its bitterness is almost instantaneous; with ammonia and the alkaline carbonates the decomposition is less rapid, particularly in the cold, and still less rapid with the bicarbonates.
At the same time that the bitterness of the waldivin disappears the liquid becomes colored deeply yellow, and is again decolorized when acidified. The solution, which contains the products of the decomposition of the waldivin reduces Fehling's solution, and deviates the plane of polarization to the right, but, not being able to produce fermentation, the formation of glucose cannot be affirmed.
In 1851, Lewy extracted from cedron a bitter crystallizable principle, which he called cedrin, and of which he described very summarily the preparation, and indicated some of its properties. Since that time, Cloez has taken up the study ("Ann. des Sciences Naturelles"), but could not obtain the cedrin, the author also having not been able to obtain the bitter principle in a crystallized state, which he has extracted from the fruits of Simaba cedron. As there can be no doubt that Lewy was in possession of the true cedron, the author admits, in explanation of these contradictory results, that the fruits that the former had treated could have been mixed with those of the waldivia, and that it was thus the latter which had furnished the crystals which he had obtained. (Lewy cites indeed in the text the Simaba cedron. At the end of his note, Dumas has added that a traveler, Saillard of Besancon, had just brought a certain quantity of cedrons, which could serve for chemical and therapeutical experiments. Now, the last cotyledon of the fruits which remained from those brought from America by his father has been confided to him by Dr. Saillard, and this is a true cedron, not a waldivia.—Comptes Rendus, 1851.)
Cedrin.—The cedron contains more than one-tenth of its weight of fatty matter, which is quite soluble in alcohol, and from which it follows that the process given for the extraction of waldivin must be slightly modified. The powdered cedron is treated with water at 50°C., then heated to boiling to coagulate the albumin, filtered and agitated with chloroform. The latter is distilled to dryness, and the residue again taken up with water, when, on evaporation of the aqueous solution, the cedrin is obtained in the form of a yellow varnish, without the least trace of crystallization.
The cedrin is very soluble in water, in which it softens before dissolving; its distinctive character is its superb greenish-yellow fluorescence, which is shown even in very dilute solutions. Like the waldivin it is exceedingly bitter; but this is not completely destroyed by alkalies; it is neutral to litmus, but tannin and the reagents for alkaloids form precipitates in its aqueous solution.
In concluding, the author expresses the opinion that this cedrin does not appear to be a body of which the purity may be guaranteed, and that new researches are necessary on the subject.
The American Journal of Pharmacy, Vol. 53, 1881, was edited by John M. Maisch.