Hydroxymethylanthraquinones from the wastes from the production of rhamnil

HYDROXYMETHYLANTHRAQUINONES FROM THE A . V. PRODUCTION Gotsiridze OF and FROM THE WASTES RHAMNIL t~. P . UDC 547.615.4:51/582.736 Kemertelidze The r h a m n i l p r e p a r a t i o n suggested by the Institute of P h a r m a c o c h e m i s t r y of the Academy of Sciences of the Georgian SSR, which is isolated f r o m the b a r k of the alder buckthorn, is widely used in medicine as a gentle laxative [1-3], Rhamnil contains about 65% of hydroxymethylanthraquinones (HMA), consisting of frangulin (45%), frangula emodin (12%), and chrysophanol (6%) [4]. The w a s t e s f r o m the production of r h a m n i l in the f o r m of the ground raw m a t e r i a l and the aqueous m o t h e r liquors still contain a c o n s i d e r a b l e amount of active HMA. The ground m a t e r i a l contains about 3.5% of HMA (50% of their initial content of this m a t e r i a l ) , and the aqueous m o t h e r liquor about 0.2%. In o r d e r to obtain the HMA, the ground m a t e r i a l was treated with an aqueous solution of sodium hydroxide (pH 8.5-9). The e x t r a c t was acidified with hydrochloric acid to pH 3-4. The p r e c i p i t a t e was d r i e d and e x t r a c t e d with ethanol - c h l o r o f o r m (1 : 3)° The e t h a n o l i c - c h l o r o f o r m e x t r a c t deposited a yelloworange c r y s t a l l i n e powder of combined HMAs having the s a m e composition as the r h a m n i l p r e p a r a t i o n Yield 1%. The HMAs w e r e e x t r a c t e d f r o m the aqueous m o t h e r liquor with ethyl acetate, giving 0.18% of this m a t e r i a l . It was s e p a r a t e d on a column of silica gel. Elution was p e r f o r m e d with c h l o r o f o r m and c h l o r o f o r m - e t h a n o l . The ground m a t e r i a l yielded four, and the m o t h e r liquor two, individual compounds, which w e r e identified with authentic s a m p l e s by their melting points, mixed melting points, e l e m e n t a r y c o m p o s i tions, UV and IR s p e c t r a , and R f values on p a p e r and t h i n - l a y e r c h r o m a t o g r a m s . The s u b s t a n c e s isolated f r o m the ground r a w m a t e r i a l f o r r h a m n i l w e r e c h a r a c t e r i z e d as frangulin with m p 226-230 ° C, f r a n g u l a emodin with mp 260-262 ° C, physcion with mp 206-208 ° C, and chrysophanol with m p 201-203 ° C, and the s u b s t a n c e s f r o m the aqueous m o t h e r liquor w e r e frangulin with mp 196-198 ° C, and frangula emodin with m p 256-258 ° C. The method for isolating the total HMAs has been introduced into the production of r h a m n i l in o r d e r to obtain an additional amount of this m a t e r i a l . LITERATURE 1° 2. 3. 4. ]~. P. K e m e r t e l i d z e and V. New Medicinal Substances A. V. G o t s i r i d z e and t~. P. A. V. G o t s i r i d z e and ]~. P. Georgian Medicinal Plants CITED Yu. Vachnadze, Tr. TNIKhFI, 9, 5 (1960). [in Russian], Moscow (1963), p. 110. K e m e r t e l i d z e , Soobshch. Akad. Nauk GruzSSR, 55.._, 2,317 (1969). K e m e r t e l i d z e , The C h e m i s t r y and Biologically Active Substances of [in Russian], Series 1, No. II (1969), pp. 255-260. I. G. Kutateladze Institute of P h a r m a c o c h e m i s t r y , Academy of Sciences of the Georgian SSR. T r a n s lated f r o m K h i m i y a Pr[rodnykh Soedinenii, No. 4, pp. 519-520, July-August, 1971. Original a r t i c l e s u b mitred F e b r u a r y 26, 1971. © 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 [or any purpose whatsoever without permission of the publisher. A copy of this article is available from the publisher for $15.00. 494  (...truncated)