ALKALOIDS OF Elaeagnus angustifolia A. G. Nikolaeva UDC 547.944/945 The isolation of harman and of tetrahydroharman from Elaeagnus angustifolia L. has been reported previously [1]. By chromatography on alumina we have obtained another two alkaloids consisting of indole derivatives. Substance III, C12HI2N2, is optically inactive. The following bands are characteristic of the UV spec- H+ trum of the alkaloid III: A" EtOHmax 233, 315 nm (log e 4.19, 4.18); ~max 246, 350 nm (log e 4.02; 4.35). Rf 0.30 (TLC, 3% methanol in chloroform system), 0.59 [paper chromatography, butan-l-ol-acetic acid- water (10 : 1 : 5)] system. The base gives a picrate with mp 234°C. Alkaloid IV, Ct2H14N2, mp 216-217°C (methanol), is optically inactive; its hydrochloride and picrate H+ melt at 245-246°C and 195-196°C. UV spectrum: ~EtOH 228,284 nm (log e 4.28, 3.90); )~max 220,270 nm max (log ~ 4.32, 3.98). The IR spectrum has bands at (cm-') : 1630, 1450 (indole ring), 3420 (Nil), 750 (four ad- jacent ring hydrogens), 1465 (methyl group). Base III was identified with the dihydroharman isolated preparatively by TLC in the synthesis of harman from tryptophan [2]. On the basis of the results given and literature information, alkaloid IV was identified as 2-methyl-l,2,3,4-tetrahydro-fl-carboline [3]. We are the first to have isolated dihydroharman from raw plant material and the first to have isolated 2-methyl-l,2,3,4-tetrahydro-fi-carboline from Elaeagnus angustifolia L. 1. 2. 3. LITERATURE CITED A. G. Nikolaeva, I. V. Terent'eva, P. E. Krivenchuk, and A. P. Prokopenko, KhPS [Chemistry of Natural Compounds], 493 (1970). W. O. Kermack, W. H. Perkin, and R. Robinson, J. Chem. Soc., 119, 1617 (1921). T. F. Platonova, A. D. Kuzovkov, and P. S. Massagetov, ZhOKh, 3128 (1958). Zaporozh'e Medical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 5, p. 638, September-October, 1970. Original article submitted April 30, 1970. © 1973 Consultants Bureau, a division of Plenum Publishing Corporation, 227 West 17th Street, New York, N. Y. 10011. All rights reserved. This article cannot be reproduced for any purpose whatsoever without permission of the publisher. A copy of this article is available from the publisher for $15.00. 659

Alkaloids of Elaeagnus angustifolia

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A L K A L O I D S OF E l a e a g n u s a n g u s t i f o l i a

A. G. N i k o l a e v a UDC 547.944/945

The isolation of harman and of tetrahydroharman from Elaeagnus angustifolia L. has been reported previously [1]. By chromatography on alumina we have obtained another two alkaloids consisting of indole derivatives.

Substance III, C12HI2N2, is optically inactive. The following bands are character is t ic of the UV spec- H + trum of the alkaloid III: A" EtOHmax 233, 315 nm (log e 4.19, 4.18); ~max 246, 350 nm (log e 4.02; 4.35). R f

0.30 (TLC, 3% methanol in chloroform system), 0.59 [paper chromatography, bu tan - l -o l - ace t i c ac id - water (10 : 1 : 5)] system. The base gives a picrate with mp 234°C.

Alkaloid IV, Ct2H14N2, mp 216-217°C (methanol), is optically inactive; its hydrochloride and picrate H + melt at 245-246°C and 195-196°C. UV spectrum: ~EtOH 228,284 nm (log e 4.28, 3.90); )~max 220,270 nm max

(log ~ 4.32, 3.98). The IR spectrum has bands at (cm-') : 1630, 1450 (indole ring), 3420 (Nil), 750 (four ad- jacent ring hydrogens), 1465 (methyl group).

Base III was identified with the dihydroharman isolated preparatively by TLC in the synthesis of harman from tryptophan [2]. On the basis of the results given and l i terature information, alkaloid IV was identified as 2-methyl- l ,2 ,3 ,4- te t rahydro-f l -carbol ine [3].

We are the first to have isolated dihydroharman from raw plant material and the first to have isolated 2-methyl- l ,2 ,3 ,4- te t rahydro-f i -carbol ine from Elaeagnus angustifolia L.

2. 3.

L I T E R A T U R E C I T E D

A. G. Nikolaeva, I. V. Terent 'eva, P. E. Krivenchuk, and A. P. Prokopenko, KhPS [Chemistry of Natural Compounds], 493 (1970). W. O. Kermack, W. H. Perkin, and R. Robinson, J. Chem. Soc., 119, 1617 (1921). T. F. Platonova, A. D. Kuzovkov, and P. S. Massagetov, ZhOKh, 3128 (1958).

Zaporozh'e Medical Institute. Translated from Khimiya Prirodnykh Soedinenii, No. 5, p. 638, September-October, 1970. Original art icle submitted April 30, 1970.

© 1973 Consultants Bureau, a division of Plenum Publishing Corporation, 227 West 17th Street, New York, N. Y. 10011. All rights reserved. This article cannot be reproduced for any purpose whatsoever without permission of the publisher. A copy of this article is available from the publisher for $15.00.

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