A.viic'AXcKit Schiff Basks Method B. Inhibition of Chemically Induced Lysis of a Preformed Plasma Clot.-The clots were prepared from human plasma containing 125I-labeled human fibrinogen by the addition of CaCl2 and bovine thrombin. After thorough washing to remove loosely bound radioactivity, fibrinolysis was initiated by the addition of o-thymotic acid (6-methyl-3-isopropylsalicylic acid) to the suspending medium and was measured by the release of radioactivity into the medium. Lysis was prevented if an antifibi'inolytic compound was present in the ambient solution. Inhibition of the release of radioactivity from the plasma clot into the ambient solution is directly proportional to inhibition of lysis. From these data, the relative potency of the antifibrinolytic compound was calculated.
ACTIVE PRINCIPLES OF Schoenocaulon oficinale 5519seconds. After filtration and drying the yellow solid was leached with 60 ml. of hot acetone. This extract was concentrated to dryness and the residue was then leached with 20 ml. of acetone at 25". The residue from evaporation of this extract was recrystallized twice from 6 ml. of ethanol to give 0.15 g. of yellow prisms, m.p. 241-247' (cloudy). This fraction (VII) was soluble in sodium bicarbonate and contained 17.47% N. Calcd. for CleHgN~0(N0~)3: N, 18.27. C.-To 0.5 g. of the hydroxypyrazine in 20 ml. of sulfuric acid a t 0" was added over ten minutes 0.09 ml. of nitric acid (d. 1.5)in 10ml. ofsulfuricacid. After15minutesatO'the solution was poured into 200 ml. of water and the yellow solid was filtered off. This was boiled a few minutes in 300 ml. of 1% aqueous sodium bicarbonate and after cooling to 25' the mixture was atered. Acidification of the yellow filtrate precipitated a small amount of solid which was leached with 8 ml. of methanol a t 25'. The residue from evaporation of the methanol was recrystallized from 4 ml. of benzene and then from 1.5 ml. of acetone to yield 6 mg. of large yellow granules, m.p. 237-240'.Presumably this is 2-hydroxy-5-nitro3,B-diphenylpyrazine (VIII).On the basis of analogies drawn from the behavior of zygadenine and its esters upon treatment with alkali, the existence of an isomeric, carbonyl-free cevagenine precursor was postulated. In a search for such a precursor, the amorphous fraction of commercial veratrine after removal of cevadine and veratridine was investigated. Fractionation using chromatographic procedures led to isolation of a new alkamine, protocevine, C Z~H~~O~N , isomeric with cevagenine and cevine and a new ester alkaloid, cevacine, C2gH&bOQN, a monoacetate ester of protocevine. Cevacine yields protocevine upon methanolysis, and protocevine is isomerized to cevagenine by mild alkaline treatment. Acetylation of protocevine with acetic anhydride and pyridine yields protocevine triacetate and similar acetylation of cevacine affords the same triester . Acetylation of protocevine with acetic anhydride and perchloric acid yields anhydroprotocevine tetraacetate, and cevadine has been shown to give an analogous tetraester (anhydrocevadine triacetate) under the same conditions. Protocevine can be obtained from cevadine by methanolysis or by alkaline hydrolysis under very mild conditions. Very mild alkaline hydrolysis of veratridine also yields protocevine. It is proposed that protocevine, and not cevagenine, is the parent alkamine of cevacine, cevadine and veratridine.
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