Alkaloids ofElaeagnus angustifolia

ALKALOIDS OF ELAEAGNUS ANGUSTIFOLIA A. G. Nikolaeva, I. V. T e r e n t ' e v a , P. E. Krivenchuk, and A. P. Prokopenko Khimiya P r i r o d n y k h Soedinenii, Vol. 6, No. 4, p. 493, 1970 UDC 547.944/945 F r o m the b a r k of the s t e m s and the b a r k of the roots of Elaeagnus angustifolia L . , collected in the period of sap m o v e m e n t in the e n v i r o n s of the town of Z a p o r o z h ' e (Khortitsa island) we have isolated the combined alkaloids by c h l o r o f o r m extraction with yields of 1 and 0.02%, respectively. The s e p a r a t i o n of the combined b a s e s f r o m the b a r k into phenolic and nonphenolic fractions with subsequent chromatography on active a l u m i n a (with benzene as eluent) gave two individual s u b s t a n c e s shown by qualitative r e a c t i o n s to be indole d e r i v a t i v e s . Alkaloid I. C12HIoN2, mp 234-235 ° C (after s u b l i m a t i o n in vacuum and r e c r y s t a l l i z a t i o n f r o m benzene), optically inactive, Rf 0.43 (TLC in a 3% methanol in chloroform system), 0+65 [paper chromatography in a b u t a n - l - o l - a e e t i e a c i d - w a t e r (10 : 1 : 5) system]. The b a s e gave a hydrochloride with mp 275 ° C (decomp) and a p i c r a t e with mp 250-255 ° C (decomp). UV s p e c t r u m of alkaloid I, ~max, n ~ : 235, 249, 288, and 336 (log e 4.58, 4.37, 4.22, and 3.68). The IR s p e c t r u m contained bands at (cm-1) 1630, 1570, 1510, and 1450 (indole ring) and 760 (four adjacent hydrogens of an a r o m a t i c ring). Alkaloid II. C12Ht4N2, mp 176-177 ° C (after s u b l i m a t i o n and r e c r y s t a l l i z a t i o n f r o m benzene), optically inactive; its chloride and dipicrate melted at 261-263 ° C and 221.5-222.5 ° C, respectively. UV s p e c t r u m , ~max, ir~: 224 and 280 (log e 4.52 and 3.92). Base I was identified as h a r m a n f r o m the absence of a d e p r e s s i o n of the melting point with a synthetic s a m p l e [6] and by its UV and IR s p e c t r a and chromatographic behavior (paper and t h i n - l a y e r chromatography). Base II proved to be identical with t e t r a h y d r o h a r m a n [1, 3]. H a r m a n is fairly widely distributed in the plant world [2, 4, 5, 7], but this is the f i r s t time that it has been isolated f r o m Elaeagnus angustifolia L. REFERENCES 1. 2. 3, 4, ,Kishinev, 5. 6. 7. B. A. Abdusalamov and A. S. Sadykov, Uzb. khim. zh., no. 6, 47, 1961. B. A. Abdusalamov and A. S. Sadykov, Uzb. khim. zh., no. 4, 79, 1962. G. P. Men'shikov, E. A. Gurevich, and G. A. Samsonova, ZhOKh, 20, 1927, 1950. I. V. T e r e n t ' e v a and A. V. Borovkov, collection: A l k a l o i d - B e a r i n g plants of Moldavia [in Russian], 41, 1960. T. A. Henry, The P l a n t Alkaloids, London, 1939. W. O. Kermack, and W. H. P e r k i n , R. Robinson, J. Chem. Soc., London, 119, 1617, 1921. R. Neu. A r z n e i m i t t e l - F o r s c h . , 6, 94, 1956. 15 J a n u a r y 1970 Z a p o r o z h ' e State Medical Institute Institute of C h e m i s t r y , AS Moldavian SSR Khar'kov S c i e n t i f i c - R e s e a r c h Chemical and P h a r m a c e u t i c a l Institute 517  (...truncated)