Cardenolides and flavonoids of Syrenia sessiliflora

CARDENOLIDES Syrenia AND FLAVONOIDS OF sessiliflora N. F . Komissarenko and O. U. Lushpa UDC 547.92+547.972 In ethanolic extracts from the epigeal p a r t of Syrenia s e s s i l i f l o r a LdIs., collected in the flowering period, we have detected cardenolides and flavonoids by qualitative reactions. F o r t h e i r isolation, an ethanolic ext r a c t was evaporated to eliminate the solvent, the residue was mixed with water, and the precipitate of c h l o r o phyll and other lypophilic substances that deposited w a s filtered off. The cardenolides were extracted f r o m the aqueous filtrate with c h l o r o f o r m containing 15% of ethanol. Under these conditions, the flavonoids r e mained in the aqueous l a y e r . After evaporation of the c h l o r o f o r m - e t h a n o l extract, the residue was separated on a column of neutral alumina (activity g r a d e HI). The column was washed with w a t e r and with mixtures of c h l o r o f o r m and ethanol with the concentration of the l a t t e r being gradually i n c r e a s e d to 7%. The qualitative compositions of the fractions collected were determined by p a p e r c h r o m a t o g r a p h y in the c h l o r o f o r m - f o r m a mide and c h l o r o f o r m - t e t r a h y d r o f u r a n (1 : 1 ) - f o r m a m i d e s y s t e m s . As a r e s u l t we obtained and identified strophanthidin (C23H3206, mp 138-143°C/224-226°C, [~]2~ +44 ° in ethanol), e r y s i m o t o x i n (C29H4209, mp 175177°C, [~]2i~+23° in ethanol), and c o r c h o r o s i d e A (C29H4209, mp 160-164°C, [~]2~)+14° in ethanol). The flavonoid glycosides p r e s e n t in the aqueous residue after the extraction of the cardenolides were separated on a column of polyamide sorbent [2]. The column was washed with water and with mixtures of w a t e r and ethanol. A diglycoside (C28I-]32016, mp 220-222°C, [~]2i~-105° in ethanol) was isolated which, on acid h y d r o l y s i s , split into isorhamnetin (C16H120~, mp 305-307°C), D-glucose, and L - r h a m n o s e . Cleavage of the glycoside with the enzymes of the g r a p e snail o r r h a m n o d i a s t a s e led to the formation of isorhamnetin 7 - ~ L - r h a m n o p y r a n o s i d e (C22H22011, mp 119-120°C, [~]z~ _ 121 ° in ethanol) and D-glucose. Alkaline h y d r o l y s i s [3] gave i s o r h a m n e t i n 3-fl-glucopyranoside (C22H22012, mp 166-169°C, [~]2~ _60 ° in ethanol) and L - r h a m n o s e . Thus, the s t r u c t u r e of the flavonoid glycoside isolated can be r e p r e s e n t e d as isorhamnetin 3-fl-D-gluc o p y r a n o s i d o - 7 - ~ - L - r h a m n o p y r a n o s i d e . We isolated a s i m i l a r substance previously f r o m the leaves of sea buckthorn [4]. LITERATURE 1. 2. 3. 4. CITED A . A . Ponomarenko, N. F. Komissarenko, and K. L. Stukkei, Khim. P r i r o d n . Soedin., 848 (1971). N . F . Komissarenko, V. T. Chernobai, and D. G. Kolesnikov, Med. Prom.. SSSR, No. 1, 25 (1965). V. L Litvinenko and V. A. Makarov, Khim. Prorodn. Soedin., 366 (1969). D . B . Rasputina, N. F. Komissarenko, D. Ts. Tsybikova, and A. Sh. Papanova, Khim. P r i r o d n . Soedin., 96 (1975). Khar'kov Scientific-Research Institute of Pharmaceutical Chemistry. Institute of Botany, Academy of Sciences of the Kazakh SSR, Alma-Ata. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 671-672, September-October, 1976. Original article submitted February 8, 1976. This material is protected by copyright registered in the name o f Plenum Publishing Corporation, 227 West 17th Street, New York, N. Y. 10011. No part o f 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 f the publisher. A copy o f this article is available from the publisher for $ 7.50. I 606  (...truncated)