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Indole alkaloids.
All the members of this group of alkaloids contain an indole nucleus in their chemical structure; however, they are derived from many different natural sources. Indole alkaloids are the principal alkaloids isolated from ergot, Strychnos nux vomica, and rauwolfia. Each of these groups will be treated separately.
Ergot alkaloids. Ergot is the dried sclerotium of the parasitic fungus Claviceps purpurea prepared and developed on plants of rye. Ergot yields not less than 0.15% of the total alkaloids of ergot calculated as ergotoxine, and water soluble alkaloids equivalent to not less than 0.01% of ergonovine. Six diastereoisomeric pairs of alkaloids have been isolated from ergot. The most physiologically active alkaloids are of the levo form. All these alkaloids can be considered to be derivatives of lysergic acid or its stereoisomer, isolysergic acid. The principal alkaloids of ergot are lysergic acid (11), ergometrine, or ergonovine (12), and ergotamine (13).
Analysis of indole alkaloids.
Ergot alkaloids. Alexander and Banes have developed a procedure for the analysis of ergot in which the total alkaloids are extracted with ammonium hydroxide methanol chloroform and the water soluble alkaloids are seperated by column chomatography. In this procedure the total alkaloid and water soluble ergot alkaloid contents are determined colorimetrically. The chromogenic reagent, p-dimethylaminobenzaldehyde, first proposed by Smith is used in this procedure. Certain amines condense with p-dimethylaminobenzaldehyde to give products which are oxidizable under strongly acidic conditions to produce a color. In the case of the ergot alkaloids, it is the indole portion of the lysergic acid nucleus which condenses with the color reagent. The detailed procedure of Alexander and Banes follows:
Reagents: The extracting solvent is a solution of 10 ml of concentrated ammonium hydroxide in 90 ml of methanol mixed with 900 ml of chloroform. Prepare the color developing reagent as follows: dissolve 125 mg of p-dimethylamino-benzaldehyde in a cooled mixture of 65 ml of concentrated sulfuric acid and 35 ml of water, and add .05 ml of 10% ferric chloride solution; use within 7 days. To prepare the diatomaceous silica support, boil 150 g of celite 545 with 1000 ml of concentrated hydrochloric acid for 10 min, cool, then wash with water to remove the acid and dry in an oven at 100°C; the washed product should give no acid test when moistened. Also prepare a standard solution containing 20µg of ergonovine/ml as follows: Dissolve 6.78 mg of ergonovine maleate reference standard in 1% tartaric acid solution.
Extraction. Weigh 5 g of ergot and place in a 125-ml sep funnel. Add 50 ml of extracting solvent and shake vigorously for 5 min. Add 50 ml of chloroform and 2 ml of water, shake gently, and allow to settle. Draw off the lower phase as completly as possible, and filter through a glass wool plug into a 200-ml volumetric flask. Add another 20 ml of extracting solvent to the ergot residues in the sep funnel, mix, add 20 ml of chloroform, and shake. Filter the lower phase through the glass wool plug into the volumetric flask. Repeat this procedure once more with an additional 20 ml of extracting solvent and 20 ml of chloroform. Dilute to volume with chloroform.
