Sedum alkaloids

3. 4. 5. 6. B. Wortmaun, W. Wortmann, and J. C. Touchstone, J. C h r o m a t o g r ~ 70__, 199 (1972). H. H. Ion, J. K. Ho, W. 1L Lipscomb, T. M. Cho, and C. Selewski, J. Chromatogr., 68___,289 (1972). H. P. R~mnen, J. C h r o m a t o g r . , 53, 600 (1967). J. T. Huang, K, T. Wang, J. C h r o m a t o g r . , 31_, 587 (1967). Sedum ALKALOIDS E. A. ~rasnov, L. V. P e t r o v a, and E. F. Bekker UDC 547/945 The alkaloids of Sedum a c r e (goldmoss stonecrop) have been c o n s i d e r e d in various publications [1-5]. We have investigated the alkaloid c o m p o s i t i o n s of the epigeal p a r t s of four Siberian species of Sedum: S. aizoon L. (aizoon stonecrop), S. p u r p u r e u m (L.) Shult. (purple stonecrop), S. hydridum L. ( e v e r g r e e n stonecrop), and S. e w e r s i i Ledeb. ( E w e r s stoneerop), collected in the T o m s k oblast (village of Urtarn) and in the Gorno-Altai Autonomous Region (villages of Maima and Kebezen') in the flowering phase. The combined b a s e s w e r e isolated by F r a n c k ' s method [4]. TLC on plates coated with A1203 in the b e n z e n e - m e t h a n o l (85 : 15) ( s y s t e m 1) and ethyl a c e t a t e - c h l o r o f o r m - m e t h a n o l ( 2 . 5 : 2 . 0 : 0.5) ( s y s t e m 2) s y s t e m s showed that the f i r s t t h r e e species have the safne qualitative composition (each containing t h r e e bases), while the c h l o r o f o r m e x t r a c t f r o m S. e w e r s i i revealed the p r e s e n c e of only one alkaloid (III). The alkaloids w e r e separated on c o m u m n of alunina (activity grade II, neutral) being eluted successively with benzene and m i x t u r e s of benzene with 5-25% of methanol. B a s e (I) was isolated in the form of a c o l o r l e s s oily residue with Rf 0.89 ( s y s t e m 1) and 0.86 ( s y s t e m 2) and gave a p i c r a t e with mp 156-158°C. IR spectrum, c m - l : 2950 (CH3), 1690 (C-----O). On the b a s i s of these r e s u l t s , the substance was identified as (:~)-methlyisopelletierine [6]. Base (II), mp 119-121°C, Rf 0.28 ( s y s t e m 1) and 0.75 ( s y s t e m 2) d e c o l o r i z e d a solution of potassium p e r manganate and b r o m i n e water. Its IR s p e c t r u m showed absorption bands at (cm -1) 3385 (OH), 2935 (CH3), 1630 (v-bond), 1590 ( a r o m a t i c ring), and 760, 745 (monosubstituted benzene nucleus). It f o r m e d a hydrochloride with mp 169-170°C, [a]~-140°C (c 0.04; CH3OH). The base was identified as ( - ) - s e d i n i n e [7]. B a s e (liD, mp 89-90°C, Rf 0.22 (system 1) and 0.61 (system 2). IR s p e c t r u m , c m - l : 3280 (OH), 2955 (CI-I3), 1570, 1485 (benzene ring). The-substance f o r m e d a h y d r o c h l o r i d e with mp 186-188°C. The r e s u l t s obtained p e r m i t t e d the conclusion that b a s e (III) was (i) -sedamine [4, 8]° A d i r e c t c o m p a r i s o n with ( ± ) - s e d a m i n e c o n f i r m e d t h e i r identity. LITERATURE CITED D. G. Kolesnikov and A. G. Shvartsman, Zh. Obshch. Khim., 9_, 2156 (1939). A. Nordal, A P h a r m a c o g n o s t i c a l Study of Sedum a c r e L., Oslo (1946). L. Marion, R. Lavigne, and Lo Lemay, Canad. J. Chem. 29__,347 (1951). B. Franck, Chem. Ber., 91__,2803 (1958). B. F r a n c k and W. Hartmann, Abhandl. Deut. Akad. Wiss., 4_) 111 (1963). L. Marion and M. Chaput, Canad. J. R e s e a r c h , 27B, 213 (1949). B. Franck, Chem. B e r . , 92_, 1001 (1959). L. Marion, Canad. J. Research, 23B, 165 (1945). 1. 2. 3. 4. 5. 6. 7. 8. T o m s k Medical Institute. 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, p, 585, July-August, 1977. Original a r t i c l e submitted M a r c h 3, 1977. This material is protected by copyright registered in the name of Plenum Publishing Corporation, 227 West 17th Street, New York, N.Y. 10011. No part [ of this publication may be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, [ I microfilming, recording or otherwise, without written permission of the publisher. A copy of this article is available from the publisher for $ Z 50. ] 492  (...truncated)