Search

Ergots col lected f rom production crops of the exper imenta l base of VILR JAil-Union Sc ien t i f i c -Research Insti tute for Medicinal Plants] (Moscow region) were used. The alkaloids were ext rac ted f rom the comminuted ergots with dichloroethane, f rom which they were exhaust ively extracted with t a r t a r i c acid solution. The ta r ta r ic ex t rac t s were made alkaline with ammonia and the bases were extracted with chloroform. The ext rac ts were dr ied over sodium sulfate and the solvent was evaporated off to small volume. On standing in the cold, white c rys ta l s deposited with mp 159-160 ° C (from methyl ethyl ketone and ethyl acetate) with the composi t ion C19H2302N3, [o~]~ +41 ° (e 1.8, ethanol). The base is readi ly soluble in methanol, ethanol, and acetone, and modera te ly soluble in benzene and water; it forms a hydrochlor ide with mp 175 ° C (decomp.), a hydrobromide with mp 239-240 ° C (decomp), and an oxalate with mp 189-190 ° C (decomp). F rom its composit ion, its melt ing point, and that of its sal ts , a mixed mel t ing point with an authentic sample, and its IR spec t rum [2] it was identified as e rgomet r ine . The mother l iquor, after the isolat ion of the e rgomet r ine , yielded a second base with the composi t ion ClsH2302N3, mp 193-194 ° C (decomp), [~]~ +412 ° (c 0.5, chloroform), readi ly soluble in ethanol, methanol, and acetone, and spar ingly soluble in ch loroform and water , giving a hydrochlor ide with mp 175-180 ° C (decomp). F r o m its composit ion, mel t ing point, and those of its sal ts , and a mixed melt ing point with an authentic sample it was identified as e rgometr in ine .

F r o m the f lowers of Ci r s ium arvense (Canada thistle) previous ly t reated with ch loroform we have obtained an ethanolie extract . By separat ing this on a polyamide sorbent we have isolated four individual flavonoid substances. Substance I, C15H1005. Mp 349-351 ° C (from ethanol), kmax 270 and 336 m#. For the acetate mp 183-185 ° C, Rf 0.86 [benzene-e thy l a c e t a t e a c e t i c acid (formamide) (24.5 : 73.5 : 2)]. The constants of I correspond to those of apigenin [1]. Substance II, C15H1006. Mp above 300 ° C, kmax 268 and 352 m#. For the acetate mp 224-226 ° C, Rf 0.63 [benzene-e thyl a c e t a t e a c e t i c acid (formamide) (24.5 : 73.5 : 2)]. This substance is identical with luteolin. Substance III, C2IH20010. Mp 222-225 ° C, ~-max 268 and 333 mtz, [a]D -62"2° (dimethylformamide) , Rf 0.77 [ b u t a n l o l a c e t i c a c i d w a t e r (4 : 1 : 5)]. The hydrolysis of III with 10% H2SO 4 gave an aglyeone Cl~H1005 with mp 349-351 ° C, identical with substance I. In the mother l iquor after hydrolys is , D-glucose was detected by paper chromatography. On the basis of the hydrolys is products, and UV and IR spect ra , substance III was cha rac te r i zed as apigenin 7-glucoside [2]. Substance IV, C27H30014. Mp 250-260 ° C, hmax 268 and 333 m#, Rf 0.55 [ b u t a n l o l a c e t i c a c i d w a t e r (4 : 1 : 5)]. The hydrolys is of IV with 10% H2SO 4 gave an aglycone with mp 349-350 ° C identified as an apigenin (UV and IR spec t ra , Rf , rap). D-Glucose and Lrhamnose were identified by paper chromatography. The constants of substance IV correspond to roifol in (apigen 7-rhamnoglucoside) . R E F E R E N C E S 1. Ya. K. Yatsyuk and S. S. Lyashehenko, KhPS [Chemis t ry of Natural Compounds], 5, 54, 1969. 2. T. A. Geissman, The Chemis t ry of Flavonoid Compounds, Pe rgamon P r e s s , New York, 227, 1962. 12 January 1970 Vitebsk Medical Insti tute