A triterpene glycoside from Dianthus inacotinus

A TRITERI~ENE V. Y a . GLYCOSIDE Chirva and P. FROM Dianthus inacotinus K. Kintya UDC 547.913+547.918 In spite of the intensive investigation of the t r i t e r p e n e glycosides of the family C a r y o p h y l l a c e a e [13], many r e p r e s e n t a t i v e s of it have still r e m a i n e d unstudied. Thus, for example, t h e r e is no information whatever in the l i t e r a t u r e on the saponins of Dianthus inacotinus. A methanolic e x t r a c t f r o m the roots of this plant contained one glycoside, which we isolated by c h r o m a t o g r a p h y on a column of silica gel in the b u t a n - l - o l - e t h a n o l - w a t e r (10 : 2 : 5) s y s t e m in p r e p a r a t i v e amount. In its melting point (I36 ° C), specific rotation ([~]~ + 35 ° (c 1.3; methanol)), and c h r o m a t o g r a p h i c mobility the compound obtained was identical with saponaside A, which we have isolated p r e v i o u s l y f r o m Saponaria officinalis L. [4]. The s u b s t a n c e was additionally identified by its methylation and the t e t r a h y d r o a l u m i n a t e cleavage of its p e r m e t h y l a t e . The reduced glycoside was found by t h i n - l a y e r c h r o m a t o g r a p h y in b e n z e n e - a c e t o n e (2 : 1) to contain 2 , 3 , 4 - t r i - O - m e t h y l - D - g l u e o p y r a n u r o n i c acid, and among the m e t h a n o l y s i s p r o d u c t s of the o l i g o s a c c h a r i d e we identified, in the p r e s e n c e of s u g a r s of known s t r u c t u r e , 2 , 4 - d i - O - m e t h y l - D - s o r b i t o l and 2 , 3 , 4 , 6 - t e t r a - O - m e t h y l - D - g l u e o p y r a n o s e . In the p e r i o d a t e oxidation of the saponin, the glucose was not affected. On this b a s i s , we concluded that Saponaria offieinalis L. (bouncing bet) and Dianthus inacotinus contain one and the s a m e saponin. LTTERATURE 1. 2. 3. 4. CITED V. Ya. C h i r v a and P. K. Kintya, Khim. Prirodn. Soedin., 6_ 214 (1970). N. K. Kochetkov, A. Ya. Khorlin, and Yu. S. Ovodov, Zh. Obshch. Khim., 32, 782 (1962). Zh. M. Putieva, L. G. M z h e l ' s k a y a , E. S. Kondratenko, and N. K. Abubakirov, Khim. P r i r o d n . Soedin., 6_, 486 (1970). V. Ya. C h i r v a and P. K. Kintya, Khim. Prirodn. Soedin., 5_ 188 (1969). Institute of C h e m i s t r y , A c a d e m y of Sciences of the Moldavian SSR. T r a n s l a t e d f r o m K h i m i y a P r i r o dnykh Soedinenii, No. 4, p. 532, July-August, 1971. Original a r t i c l e submitted M a r c h 4, 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 for any purpose whatsoever without permission of the publisher. A copy of this article is available from the publisher for $15.00. 515  (...truncated)