Merenderine — A new base from Merendera raddeana

ME R E N D E R I N E - A NEW BASE FROM Merendera raddeana A. A. T r o z y a n , A . S. S a d y k o v M. K . Y u s u p o v , and UDC 547.944.6 One of the g e n e r a of the f a m i l y L i l i a c e a e that contain the g r e a t e s t amount of alkaloids is M e r e n d e r a Ram. ( m e r e n d e r a ) which is r e p r e s e n t e d in the USSR by eight s p e c i e s [1 ]. The m a j o r i t y of them have not been investigated f o r their content of alkaloids o r h a v e been studied insufficiently. We have investigated M e r e n d e r a r a d d e a n a Rgl. collected in the flowering p e r i o d on the slopes of Mr. A r a g a t s (Armenian SSR). It was knov~n that this plant contains colchicine [2, 3]. The epigeal p a r t of the p l a n t (780 g) was e x t r a c t e d with methanol. N e u t r a l (I) and b a s i c (II) f r a c t i o n s of the alkaloids w e r e obtained by the p r o c e d u r e d e s c r i b e d p r e v i o u s l y [4]. Then f r a c t i o n s (I) and (II) w e r e s e p a r a t e d into phenolic and nonphenolic p a r t s . F r a c t i o n (I) yielded 0.13% of nonphenolic, 0.07% of phenolic, and 0.11% of phenolic acid substances, and (II) 0.02% of nonphenolic b a s e s and 0.17% of phenolic b a s e s . C h r o m a t o g r a p h y in a thin l a y e r of alumina [ c h l o r o f o r m - m e t h a n o l (24 : 1)] s y s t e m of the phenolic and nonphenolic compounds in f r a c t i o n (I) showed the p r e s e n c e of fi-lumicolehlcine, colehicine, 2 - d e s m e t h y l colchlcine, N - f o r m y l d e s a c e t y l c o l c h i c i n e , 3-desmethyl-/~-lumicolchicine, 3 - d e s m e t h y l - ~ - l u m i c o l c h i c i n e , and 2 - d e s m e t h y l - f i - l u m i c o l c h i c i n e [5, 6]. The f i r s t three alkaloids w e r e also isolated by s e p a r a t i n g the m i x t u r e s of alkaloids in a column of alumina and w e r e identified b y t h e i r p h y s i c o c h e m i c a l constants in c o m p a r i s o n with authentic s a m p l e s . It was shown by p a p e r c h r o m a t o g r a p h y [ b n t a n - l - o l - 1 2 % aqueous a m monia (2 : 1) s y s t e m ] that the phenolic acid f r a c t i o n contained colchiceine and 2 - d e s m e t h y l c o l e h i c e [ n e . The s u b s t a n c e s f r o m fraction (II) could not be s e p a r a t e d by c h r o m a t o g r a p h y on p a p e r and in a thin l a y e r of alumina. The c h r o m a t o g r a p h y of the phenolic b a s e s on a column of alumina yielded an unknown alkaloid with the composit[onC2~H25-27 O~N, mp 219-230°C (from acetone), [ ~ ] ~ 105 ° (c 0.57; c h l o r o f o r m ) , tool. wt. 374 ( m a s s s p e c t r o m e t r i c a l l y ) . UV s p e c t r u m in methanol: ~'max 260 nm (log e 4.11). The alkaloid does not h a v e a tropolone ring and its p h y s i c o c h e m i c a l constants differ f r o m those of known compounds. It has been called m e r e n d e r i n e . Colchicine and m e r e n d e r i n e a r e the main alkaloids of the plant. LITERATURE 1. 2. 3. 4. 5o 6° CITED F l o r a of the USSR [in Russian], Moscow and Leningrad, Vol. 4 (1935). G. Klein, Handbuch d e r P f l a n s e n a n a l y s e , Vienna, Vol. VI (1933). A. A. Trozyan, Dokl. Akad. Nauk ArmSSR, 46, 34 (1968). M. A. Yusupov and A. S. Sadykov, Nauchn. T r . TashGU ira. V. I. Lenina, Khimiya Rastit. Veshchestv, II, No. 286, 56 (1966). F. Santavy, P h a r m . Zentralhalle, 96, 307 (1957). B. Chommadov, M. K. Yusupov, and A. S. Sadykov, Khim. P r i r o d n . Soedin., 6, 82, 275, (1970). V. I. Lenin T a s h k e n t State University. T r a n s l a t e d f r o m Khimiya P r i r o d n y k h Soedinenii, No. 4, pp. 541-542, July-August, 1972. Original a r t i c l e submitted M a r c h 25, 1971. © 1973 Consultants Bureau, a division of Plenum Publishing Corporation, 227 West ]7th 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. 529  (...truncated)