Triterpene acids from the wastes from the production of thyme extract

TRITERPENE FROM THE ACIDS FROM PRODUCTION THE OF A. V. Simonyan, ]~. T . a n d R . A. A z a r y a n WASTES THYME EXTRACT Oganesyan, UDC 547.913 An e x t r a c t of the h e r b T h y m u s s e r p y l l u m L. (thyme) is included in the p r e p a r a t i o n " p e r t u s s i n . " In the p r e p a r a t i o n of the thyme e x t r a c t , the raw m a t e r i a l is t r e a t e d with 30% ethanol, but t r i t e r p e n e c o m pounds d i s s o l v e sparingly in dilute ethanol, and t h e r e f o r e we have studied the waste m a t e r i a l after the p r e p a r a t i o n of the thyme e x t r a c t for its t r i t e r p e n o i d content [1]. We have r e p o r t e d p r e v i o u s l y that this m a t e r i a l contains 1.62% of neutral t r i t e r p e n o i d s and 2.96% of t r i t e r p e n e acids [2]. To isolate the t r i t e r p e n e acids, a f t e r exhaustive extraction with p e t r o l e u m e t h e r the m a t e r i a l was t r e a t e d with c h l o r o f o r m . When the c h l o r o f o r m e x t r a c t was concentrated, a dirty-yellow p r e c i p i t a t e d e posited which was s e p a r a t e d off and dissolved in 95% ethanol. The ethanolic solution was r e p e a t e d l y p u r i fied by s u c c e s s i v e boiling with 2 N hydrochloric acid and with a 5% solution of caustic potash. The p u r i fied ethanolic solution was concentrated, whereupon thin c o l o r l e s s needles (substance I) began to deposit. A c h l o r o f o r m e x t r a c t a f t e r the s e p a r a t i o n of the f i r s t p r e c i p i t a t e was c o n c e n t r a t e d and dissolved in 95% ethanol and was purified as d e s c r i b e d above. The purified ethanelic solution was p a s s e d through a column containing activated carbon. Elution was p e r f o r m e d with ethanol until the reaction for t r i t e r p e n o i d s was negative. The eluates w e r e concentrated, giving a white c r y s t a l l i n e compound (ID [3]. Both products gave positive chlorosulfonic acid, L i e b e r m a n n - B u r c h a r d , and Sal'kovskii reactions. On the b a s i s of a p h y s i c o c h e m i c a l investigation and chemical a n a l y s i s , and also the analysis of a s e r i e s of d e r i v a t i v e s of the compounds isolated, compound (I) was identified as ursolic acid and (II) as oleanolic acid [4]. LITERATURE 1. 2. 3. 4. C. A. A. V. H. V. V. D. CITED B r i e s k o r n , Planta Medica, No. 3, 83 (1955). Simonyan, A. L. Shinkarenko, andl~. T. Oganesyan, Khim. P r i r o d n . Soedin., 293 (1972). Simonyan and A. L. Shinkarenko, Khim. P r i r o d n . Soedin., 632 (1970). P o n o m a r e v , 1~. T. Oganesyan, and V. F. Semenchenko, Khim. P r i r o d n . Soedin., 147 (1971). P y a t i g o r s k P h a r m a c e u t i c a l 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. 1, p. 123, J a n u a r y - F e b r u a r y , 1973. Original a r t i c l e submitted July 4, 1972. ©1975 Consultants Bureau, a division of Plenum Publishing Corporation, 227 West 17th Street, New York, N. Y. 10011. No part o[ this publication may be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, microfilming, recording or otherwise, without written permission o[ the publisher. A copy o[ this article is available [rom the publisher for $15.00. 122  (...truncated)