ZYGADENUS ALKALOIDS. II. THE OCCURRENCE OF HYPOTENSIVE GERMINE ESTERS IN ZYGADENUS VENENOSUS

Journal of the American Chemical Society
1952.0

Abstract

A recent study of the alkaloidal constituents of Zygadenus venenosus revealed the occurrence of veratroylzygadenine, vanilloylzygadenine, zygadenine and germine. We report the isolation from the plant collected in June 1951 of the germine esters neogermitrine, germidine, protoveratridine, and a new diester neogermidine (isomeric with germidine). Fractionation was performed by countercurrent distribution and chromatography, and the compounds were characterized by melting point, optical rotation, elemental analysis, hydrolysis (yielding germine, acetic acid and α-methylbutyric acid for neogermidine) and acetylation (neogermidine and protoveratridine yielding acetylneogermitrine). Pharmacological experiments showed neogermidine has circulatory action in cats and veratrinic effect on frog muscle similar to germidine. In studies on enzymatic synthesis of dextran from sucrose by Leuconostoc mesenteroides, 37% of sucrose was diverted to a new disaccharide under certain conditions. The disaccharide is a D-glucosyl-D-fructose (glucosyl likely in pyranose form) with properties including crystallization as bars from methanol-ethyl acetate (m.p. 161-163°C), [α]²⁵D -8.8° (3 min) to -6.8° (24 h, c=4, H₂O), molecular formula C₁₂H₂₂O₁₁, 46% reducing power of fructose (Somogyi method), 9% reaction with hypoiodite, positive Seliwanoff test for fructose, hydrolysis to glucose and fructose (paper chromatography), phenylosazone (m.p. 186-188°C, C₁₈H₂₄N₄O₆) and phenylosotriazole (hydrolyzing to D-glucose and D-glucose phenylosotriazole).

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