ALKALOIDS OF ELAEAGNUS ANGUSTIFOLIA A. G. Nikolaeva, I. V. Terent'eva, P. E. Krivenchuk, and A. P. Prokopenko Khimiya Prirodnykh Soedinenii, Vol. 6, No. 4, p. 493, 1970 UDC 547.944/945 From the bark of the stems and the bark of the roots of Elaeagnus angustifolia L., collected in the period of sap movement in the environs of the town of Zaporozh'e (Khortitsa island) we have isolated the combined alkaloids by chloroform extraction with yields of 1 and 0.02%, respectively. The separation of the combined bases from the bark into phenolic and nonphenolic fractions with subsequent chromatography on active alumina (with benzene as eluent) gave two individual substances shown by qualitative reactions to be indole derivatives. Alkaloid I. C12HIoN 2, mp 234-235 ° C (after sublimation in vacuum and recrystallization from benzene), optically inactive, Rf 0.43 (TLC in a 3% methanol in chloroform system), 0+65 [paper chromatography in a butan-l-ol-aeetie acid-water (10 : 1 : 5) system]. The base gave a hydrochloride with mp 275 ° C (decomp) and a picrate with mp 250-255 ° C (decomp). UV spectrum of alkaloid I, ~max, n~: 235, 249, 288, and 336 (log e 4.58, 4.37, 4.22, and 3.68). The IR spectrum contained bands at (cm-1) 1630, 1570, 1510, and 1450 (indole ring) and 760 (four adjacent hydrogens of an aromatic ring). Alkaloid II. C12Ht4N 2, mp 176-177 ° C (after sublimation and recrystallization from benzene), optically inactive; its chloride and dipicrate melted at 261-263 ° C and 221.5-222.5 ° C, respectively. UV spectrum, ~max, ir~: 224 and 280 (log e 4.52 and 3.92). Base I was identified as harman from the absence of a depression of the melting point with a synthetic sample [6] and by its UV and IR spectra and chromatographic behavior (paper and thin-layer chromatography). Base II proved to be identical with tetrahydroharman [1, 3]. Harman is fairly widely distributed in the plant world [2, 4, 5, 7], but this is the first time that it has been isolated from Elaeagnus angustifolia L. REFERENCES 1. B. A. Abdusalamov and A. S. Sadykov, Uzb. khim. zh., no. 6, 47, 1961. 2. B. A. Abdusalamov and A. S. Sadykov, Uzb. khim. zh., no. 4, 79, 1962. 3, G. P. Men'shikov, E. A. Gurevich, and G. A. Samsonova, ZhOKh, 20, 1927, 1950. 4, I. V. Terent'eva and A. V. Borovkov, collection: Alkaloid-Bearing plants of Moldavia [in Russian], ,Kishinev, 41, 1960. 5. T. A. Henry, The Plant Alkaloids, London, 1939. 6. W. O. Kermack, and W. H. Perkin, R. Robinson, J. Chem. Soc., London, 119, 1617, 1921. 7. R. Neu. Arzneimittel-Forsch., 6, 94, 1956. 15 January 1970 Zaporozh'e State Medical Institute Institute of Chemistry, AS Moldavian SSR Khar'kov Scientific-Research Chemical and Pharmaceutical Institute 517

Alkaloids of Elaeagnus angustifolia

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ALKALOIDS OF ELAEAGNUS ANGUSTIFOLIA

A. G. Nikolaeva, I. V. Teren t ' eva , P. E. Krivenchuk, and A. P. Prokopenko

Khimiya Pr i rodnykh Soedinenii, Vol. 6, No. 4, p. 493, 1970

UDC 547.944/945

F r o m the bark of the s tems and the bark of the roots of Elaeagnus angustifolia L. , collected in the period of sap movement in the environs of the town of Zaporozh 'e (Khortitsa island) we have isolated the combined alkaloids by chloroform extract ion with yields of 1 and 0.02%, respect ively.

The separat ion of the combined bases f rom the bark into phenolic and nonphenolic fract ions with subsequent chromatography on active a lumina (with benzene as eluent) gave two individual substances shown by quali tat ive reac t ions to be indole der ivat ives .

Alkaloid I. C12HIoN 2, mp 234-235 ° C (after subl imat ion in vacuum and recrys ta l l i za t ion f rom 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 ac id -wa te r (10 : 1 : 5) system]. The base gave a hydrochloride with mp 275 ° C (decomp) and a p icra te with mp 250-255 ° C (decomp).

UV spec t rum of alkaloid I, ~max, n ~ : 235, 249, 288, and 336 (log e 4.58, 4.37, 4.22, and 3.68). The IR spec t rum contained bands at (cm-1) 1630, 1570, 1510, and 1450 (indole ring) and 760 (four adjacent hydrogens of an a romat ic ring).

Alkaloid II. C12Ht4N 2, mp 176-177 ° C (after subl imat ion and rec rys ta l l i za t ion f rom benzene), optically inactive; its chloride and dipicrate melted at 261-263 ° C and 221.5-222.5 ° C, respect ively. UV spectrum, ~max, ir~: 224 and 280 (log e 4.52 and 3.92).

Base I was identified as ha rman f rom the absence of a depress ion of the melt ing point with a synthetic sample [6] and by its UV and IR spec t ra and chromatographic behavior (paper and th in- layer chromatography).

Base II proved to be identical with te t rahydroharman [1, 3]. Harman is fair ly widely dis t r ibuted in the plant world [2, 4, 5, 7], but this is the f i r s t t ime that it has been isolated f rom Elaeagnus angustifolia L.

R E F E R E N C E S

1. B. A. Abdusalamov and A. S. Sadykov, Uzb. khim. zh. , no. 6, 47, 1961. 2. B. A. Abdusalamov and A. S. Sadykov, Uzb. khim. zh. , no. 4, 79, 1962. 3, G. P. Men'shikov, E. A. Gurevich, and G. A. Samsonova, ZhOKh, 20, 1927, 1950. 4, I. V. Te ren t ' eva and A. V. Borovkov, collection: Alkaloid-Bear ing plants of Moldavia [in Russian],

,Kishinev, 41, 1960. 5. T. A. Henry, The Plant Alkaloids, London, 1939. 6. W. O. Kermack, and W. H. Perkin , R. Robinson, J. Chem. Soc., London, 119, 1617, 1921. 7. R. Neu. A r z n e i m i t t e l - F o r s c h . , 6, 94, 1956.

15 January 1970

Zaporozh 'e State Medical Insti tute

Insti tute of Chemis t ry , AS Moldavian SSR

Khar 'kov Scient i f ic -Research Chemical and Pharmaceut ica l Insti tute

517